Chemistry Biodiversity - 2015 - Rios - Chemistry and Biology of The Genus Flourensia Asteraceae

CHEMISTRY & BIODIVERSITY – Vol.
12 (2015) 1595
REVIEW
Chemistry and Biology of the Genus Flourensia (Asteraceae)

by Mara Yolanda Rios
Centro de Investigaciones Qumicas, IICBA, Universidad Autýnoma del Estado de Morelos, Avenida
Universidad 1001, Col. Chamilpa, 62209 Cuernavaca, Morelos, M¦xico
(phone: þ 52-777-3297000 ext. 6024; fax: þ 52-777-3297997; e-mail: myolanda@uaem.mx)
In honor of Dr. Alfonso Romo de Vivar Romo who has been a great inspiration to me
Flourensia species are dominant plants that are adapted to semidesertic and desertic regions. It is
believed that they are successful plants because they employ several protection mechanisms, including
the formation of a waxy film on their aerial parts to protect them from dehydration. This waxy film
contains chemical compounds that are capable of inhibiting the growth of other plants and of acting as
allelopathic and herbicidal agents and as germination inhibitors. These plants also limit herbivory, and
they exhibit insecticidal, insect antifeedant, antibacterial, antifungal, antialgal, and antitermite activities.
Sesquiterpenes, flavonoids, benzofurans, chromenes, coumarins, lupan triterpenes, aliphatic lactones, and
aromatic and acetilenic compounds have all been isolated from the organic extracts of Flourensia species.
Monoterpenes, sesquiterpenes, and aliphatic hydrocarbons are the main constituents found in their
essential oils. This review is an overview of the chemical constituents and of the biological activities of
Flourensia species.
Contents
1. Introduction
2. Chemical Composition of Flourensia Species
2.1. Sesquiterpenes
2.2. Flavonoids
2.3. Benzofurans, Chromenes, and Coumarins
2.4. Miscellaneous Compounds
2.5. Essential Oils
3. Ecological Aspects
3.1. Flourensia campestris Griseb.
3.2. F. cernua DC.
3.3. F. oolepis S. F. Blake
3.4. F. thurifera DC.
3.5. F. microphylla S. F. Blake, F. cernua, and F. retinophylla S. F. Blake
3.6. F. riparia Griseb., F. fiebrigii S. F. Blake, and F. tortuosa Griseb.
4. Ethnopharmacology
5. Conclusions
Õ 2015 Verlag Helvetica Chimica Acta AG, Zîrich

1596 CHEMISTRY & BIODIVERSITY – Vol. 12 (2015)
1. Introduction. – Asteraceae is one of the largest families in the order Asterales

(Angiospermas) [1]. It comprises three subfamilies, 17 tribes, ca. 1,300 genera, and
23,000 species. This family predominantly includes herbs and shrubs, although some of
its members are vines and small trees. Plants belonging to Asteraceae are found
throughout the entire world [2].
The genus Flourensia belongs to the Ecliptinae subtribe, Heliantheae tribe, and
Asteroideae subfamily, which is the most diverse subfamily of Asteraceae [3] [4]. This
genus consists of 42 species [5] of aromatic and resinous subshrubs, shrubs, and small
trees (Fig. 1) that are characterized by their abundant yellow flowers (Fig. 1). Plants of
Flourensia grow exclusively on the American continent in the southern United States,
M¦xico, Perffl, Bolivia, Chile, and Argentina [6], and are perfectly adapted to semiarid,
arid, and desertic regions that are characterized by stress, poor soils, droughts, high
temperatures, and elevated UV-B radiation [7 – 9]. The success of these plants to adapt
and colonize these areas suggests that they possess several mechanisms to ensure their
survival and supremacy over other cohabiting plants. Some of these demonstrated
mechanisms include architectural, morphological, and anatomical factors, which are
summarized as follows: i) the orientation of their leaves and stems (Fig. 1) allows the
interception of water running along the plant and directs it to the shrub base to ensure
maximum absorption by the plant [10]; ii) Flourensia species possess secretor ducts in
their leaves and stems. It is believed that these structures are responsible for the
production and secretion of resins, which is most likely an important adaptation for the
development of an oily film on their aerial parts to protect from dehydration; iii) these
plants also possess abundant stomas to promote an efficient gas exchange; iv)
Flourensia plants possess a large, spongy parenchyma, which promotes a high
photosynthetic activity [11]; and v) their metabolic products consist of a wide variety
of compounds that possess interesting protective properties, including allelochemicals
and herbicides [12], inhibitors of the germination and growth of other plants [9] [13],
compounds that discourage herbivory [14], insecticides [15], insect antifeedants
[7] [13], and antibacterial [16], antialgal and antitermite [17], and antifungal [17] [18]
compounds, among others. All these characteristics of the Flourensia species ensure
that these plants can grow and replace the typical desert vegetation, changing its
composition and balance [14] [19] [20]. Certain Flourensia plants are used in some
Fig. 1. Anatomical aspects of Flourensia plants

CHEMISTRY & BIODIVERSITY – Vol. 12 (2015) 1597
countries for various purposes, such as in the alleviation of gastrointestinal ailments,

stomachaches, indigestion, diarrhea, dysentery [17] [21], digestive disorders, rheuma-
tism, venereal diseases, sores, bronchitis, chicken pox, and the common cold [22]. Their
resins have also been used as incense, and as flavoring agents and natural dyes [11].
Due to all these characteristics, the plants of the genus Flourensia possess considerable
ecological, medicinal, and chemical value. To the best of my knowledge, there has been
no previous effort to provide a compilation from the available information on the genus
Flourensia. This review compiles information that has been reported in the literature up
to December 2013, providing a comprehensive survey about the ecological and
ethnopharmacological roles of the Flourensia species and correlating them with the
chemical composition of this genus.
2. Chemical Composition of Flourensia Species. – To date, 13 species of Flourensia

have been analyzed. Chemical analyses have been performed on eleven of the species,
and nine species have demonstrated biological activities. Table 1 summarizes their
identity, origin, parts of plants analyzed, extraction method, analysis performed, and
biological activities.
Many investigations have been conducted to establish the chemical profiles and
molecular data of species from the genus Flourensia. Since 1970 until today, research
groups from Argentina, Chile, Germany, M¦xico, and the Unites States (Table 1) have
analyzed at least eleven species of this genus. The pioneer studies on the chemistry of
Flourensia plants were conducted by Rao [27], Kingston [28] [29], Dillon [23] [31],
Bohlmann [32] [54], Guerreiro [56], and Rodrguez-Hahn [59], all of whom established
the bases of the compositions of this genus. The chemical structures of more than 330
compounds have been established (Table 2). The most distinctive chemical constitu-
ents from Flourensia species are the eudesmane and eudesmanolide sesquiterpenes, in
addition to flavones, flavanones, flavonols, and benzofurans, chromenes, and coumar-
ins. The constituents that have been isolated less frequently or that are present as minor
components from these plants include the p-hydroxyacetophenones, p-hydroxycin-
namic acid derivatives, and aromatic compounds, although lupane triterpenes, aliphatic
lactones, acetilenes, and miscellaneous compounds have also been found. Essential oils
from Flourensia species are rich in active mono- and sesquiterpenes. The chemical
profiles of these species are very important to characterize the genus Flourensia.
2.1. Sesquiterpenes. Despite the large number of sesquiterpenoid carbon skeletons
identified in nature, the eudesmanes are the only distinctive sesquiterpenes that have
been characterized in the Flourensia species analyzed chemically until today.
Thirty-six compounds belonging to this chemical category have been isolated in
eight Flourensia plants. Most of them are oxidized as the carboxylic acids at C(13) (1 –
23), and less frequently, this carbon appears as ester (24), primary alcohol (25 and 26)
or Me groups (27 and 28). Commonly, C(1) is a CH2 group (1 – 17 and 24 – 28); however,
a C(1)¼C(10) bond (18), alcohol (19 – 21), ester (22), or ketone (23) groups can be
found. Commonly, C(9) is a CH2 group (1 – 11, 16, and 20 – 28), although alcohol (12 –
14 and 19) and ketone (15, 17, and 18) groups have been found also at this position. An
alcohol group can also be present at C(3), but it is frequently esterified as an
senecioyloxy, angeloyloxy, tiglinoyloxy, isobutyryloxy, isovaleroyloxy, (2-methylbuta-
noyl)oxy, or cinnamoyloxy group (2 – 11). C(4) can include a ¼CH2 (1 – 15, 19 – 23, 26,
1598
Table 1. Chemically and Biologically Analyzed Species of the Genus Flourensia
Species Origin Plant material Extract Analysis Biological activity Ref.

F. campestris Griseb. Argentina Aerial parts H2O Chemical composition, Phytotoxic [9]
Dry leaf volatiles
– Leaves CHCl3 Chemical composition – [23]
Cýrdoba, Argentina Aerial parts MeOH Chemical composition – [24]
Cýrdoba, Argentina Aerial parts EtOH – Herbicidal [25]
activity
Cýrdoba, Argentina Aerial parts MeOH – Tyrosinase [26]
inhibition
F. cernua DC. New Mexico, USA 95% EtOH, MeOH, – – Acceptability [14]
ether, acetone to sheep
sprayed branches
New Mexico, USA Leaves Hexane, Et2O, Volatile compounds Antifungal, cyano- [17]
EtOH bactericide, anti-
algal, antitermite
New Mexico, USA Leaves – – Effect of the [19]
chronic ingestion
New M¦xico, USA Leaves EtOH Volatile compounds – [20]
San Luis Potos, M¦xico Aerial parts CH2Cl2/MeOH Chemical composition Phytotoxicity [21]
(1 : 1)
Chihuahua, Mexico Leaves – Gallic and ellagic acids Fungal biodegra- [22]
production dation of tannins
Texas, USA Whole plant heads EtOH Flavonoids – [27]
CHEMISTRY & BIODIVERSITY – Vol. 12 (2015)
Texas, USA Flowering heads EtOH Chemical composition – [28]

Texas, USA whole plant heads Petrol oil Chemical composition Toxicity against [29]
goldfish
Texas, USA Plant – Flourensadiol – [30]
Texas, USA Leaves CHCl3 Chemical composition – [31]
– Aerial parts Ether/petrol Chemical composition – [32]
ether (1 : 2)
USA Leaves CHCl3 Volatile compounds – [33]
Table 1 (cont.)

New Mexico, USA Leaves Ether extract Dry matter, ash, gross – [34]
energy, phosphorus, total
phenolics, and nitrogen
New Mexico, USA Leaves EtOH, Volatile compounds – [35]
essential oil
New Mexico, USA Leaves CHCl3 Volatile compounds Livestock herbivory [36]
New Mexico, USA Whole plant – Movement of secondary – [37]
compounds, from the leaf
surface to surrounding soil
surfaces via precipitation
– Whole plant CHCl3/MeOH – Antibiotic and [38]
(1 : 1) cytotoxic activities
New Mexico, USA Leaves – Loss of phenolic, – [39]
from leaf
Nuevo Leýn, M¦xico Aerial parts Hexane, acetone, – Against M. tuber- [40]
MeOH, H2O culosis
Coahuila, M¦xico Leaves EtOH – Antifungal [41]
Nuevo Leýn and Laeves, stem, MeOH – Antioxidant [42]
Coahuila, M¦xico root, flowers
Coahuila, M¦xico Leaves MeOH/6m HCl Ellagic acid – [43]
4.95 – 0.5
Coahuila, M¦xico Leaves 70% Acetone Gallic and ellagic acids Fungal biodegra- [44]
production dation of tannins

Coahuila, M¦xico Leaves Lanolin and Hydrolysable and Antifungal [45]
cocoa butter condensed tannins
– Leaves 60% EtOH – Acute toxicity [46]
Nuevo Leýn, M¦xico Whole plant H2O, EtOH – Bactericidal [47]
activity against
M. tuberculosis
1599
Table 1 (cont.)
1600

M¦xico Leaves 70% EtOH Presence of ellagic, gallic, – [48]
cinnamic, and 2-hydroxy-
cinnamic acids, quercetin,
methyl gallate
Coahuila, M¦xico Leaves Water, 70% Assays for detection of Antibacterial [49]
EtOH, lanolin, terpenes, saponins, and
and cocoa butter tannins
Coahuila, M¦xico Fermented leaves H2O – Antioxidants, [50]
antifungal
New Mexico, USA Leaves EtOH Volatile compounds – [51]
F. fiebrigii S. F. Blake Salta, Argentina Aerial parts EtOH/H2O (98 : 2) Chemical composition – [52]
Salta, Argentina Aerial parts EtOH/H2O (98 : 2) Chemical composition in vitro inhibition [53]
of Paenibacillus
larvae
F. heterolepis S. F. Blake Bolivia Aerial parts Ether/petrol ether Chemical composition – [54]
(1 : 2)
F. ilicifolia S. F. Blake – Leaves CHCl3 Chemical composition – [23]
F. macrophylla S. F. Blake Peru Aerial parts Et2O/petrol ether Chemical composition – [55]
(1 : 2)
F. microphylla S. F. Blake Coahuila, M¦xico Leaves EtOH – Antifungal [41]
F. oolepis S. F. Blake Cýrdoba, Argentina Aerial parts EtOH Bio-guided fractionation Germination-inhibi- [12]
tory, seedling growth,
mitosis inhibition
Cýrdoba, Argentina Aerial parts EtOH Chemical composition Insect antifeedant [13]
San Luis, Argentina Aerial parts Essential oil Volatile compounds Insecticidal [15]
San Luis, Argentina Aerial parts Petrol, AcOEt Chemical composition – [56]
Cýrdoba, Argentina Aerial parts Essential oil Volatile compounds – [57]
Cýrdoba, Argentina Aerial parts EtOH – Antifeedant, [58]
germination
inhibition and
antibacterial
activities
Table 1 (cont.)

F. resinosa S. F. Blake – Aerial parts Ether/petrol ether Chemical composition – [32]
(1 : 2)
Hidalgo, M¦xico Aerial parts EtOH/benzene Chemical composition – [59]
Hidalgo, M¦xico Leaves Acetone Chemical composition – [60]
Hidalgo, M¦xico Aerial parts Acetone Chemical composition – [61]
F. retinophylla S. F. Blake – Leaves CHCl3 Chemical composition – [23]
Coahuila, M¦xico Leaves EtOH – Antifungal [41]
Coahuila, M¦xico Aerial parts CHCl3 Chemical composition – [62]
F. riparia Griseb Salta, Argentina Aerial parts MeOH Chemical composition – [24]
Salta, Argentina Aerial parts MeOH, EtOH Chemical composition in vitro inhibition [53]
of Paenibacillus
larvae
Salta, Argentina Aerial parts CHCl3 Chemical composition – [63]
F. tortuosa Griseb Salta, Argentina Aerial parts EtOH – in vitro inhibition [53]
of Paenibacillus
larvae
F. thurifera DC. Cuesta Barriga, Chile Stems and leaves CH2Cl2 Chemical composition Insect antifeedant, [7]
Toxicity [64]
V Region, Chile Fresh flower heads CH2Cl2 Volatile compounds – [8]
1601
Table 2. Chemical Constituents Isolated from the Genus Flourensia
1602
No. InChI Key Name Source Ref.

Sesquiterpenes
1 QXRKIZKJLNNMNC-VYHDIPPYSA-N 11,13-Dihydrocostic acid F. heterolepis [54]
2 GQDFYCPPHMEHJL-OSFYFWSMSA-N 3b-Hydroxycostic acid F. thurifera [64]
3 MZGZBKOVOQIZTD-YAKHIFCKSA-N 11,13-Dihydro-3b-hydroxycostic acid F. heterolepis [54]
4 DALHBHBVKMUAGC-BQFHOOILSA-N 11,13-Dihydro-3b-(senecioyloxy)costic acid F. heterolepis [54]
5 ICZYXHWGOOKQGA-YYIJFMORSA-N 3b-( Angeloyloxy)-11,13-dihydrocostic acid F. heterolepis [54]
6 ICZYXHWGOOKQGA-MAJXZTAFSA-N 11,13-Dihydro-3b-(tiglinoyloxy)costic acid F. heterolepis [54]
7 QXCPZBACALUQKU-HOVDBYTOSA-N 11,13-Dihydro-3b-(isobutyryloxy)costic acid F. heterolepis [54]
8 QRGVSAHKJSORLR-BQFHOOILSA-N 11,13-Dihydro-3b-(isovaleroyloxy)costic acid F. heterolepis [54]
9 RORFCSNULOZWPL-GWDNHDFBSA-N 3b-(Cinnamoyloxy)-11,13-dihydrocostic acid F. heterolepis [54]
10 NBJINZDEPOZGHW-IXTZJTIZSA-N 3b-( Angeloyloxy)costic acid F. thurifera [64]
11 OXNNPTNEJORZKS-FYBRHSHWSA-N 3b-[(2-methylbutanoyl)oxy]costic acid F. thurifera [64]
12 IBJRJSQUSVUUDO-XPCVCDNBSA-N 9a-Hydroxycostic acid F. macrophylla [55]
13 IBJRJSQUSVUUDO-ABHRYQDASA-N 9b-Hydroxycostic acid F. macrophylla [55]
14 KHZYQMCNLHYXTR-MCZMQQNQSA-N 8b,9b-Dihydroxycostic acid F. macrophylla [55]
15 KFBQIRUEUFUXRO-HUBLWGQQSA-N 9-Oxocostic acid F. macrophylla [55]
16 FXKCXGBBUBCRPU-QHSBEEBCSA-N Ilicic acid F. oolepis, F. resinosa [56] [61]
17 JCJJVXVYFHWGRJ-AYIJCJCZSA-N Flourensic acid F. cernua [28] [29]
18 CPDBOUQRDMUUIN-ZVWUFJHRSA-N Dehydroflourensic acid F. cernua [21]
19 SZCYKIWOPBWRQI-DKBOKBLXSA-N 1b,9b-Dihydroxycostic acid F. macrophylla [55]
20 XNAJSXARJATVJQ-PJAMKBAFSA-N 11,13-Dihydro-1a-hydroxycostic acid F. heterolepis [54]
21 GQPJZGWMHPSVIQ-UKTARXLSSA-N 1a-Hydroxycostic acid F. heterolepis [54]
22 YYBIQPSNXWPNKH-WJUQNRLRSA-N 1a-( Angeloyloxy)costic acid F. heterolepis [54]
23 NSWYDQDLHIJCPK-TYNCELHUSA-N 1-Oxocostic acid F. heterolepis [54]

F. macrophylla [55]
24 OWZSHJKGKHTKDS-CZUORRHYSA-N Isocostic acid methyl ester F. resinosa [59]
25 RMARCXQAHOJNRB-KBUPBQIOSA-N 4aH-Eudesm-11(13)-ene-4,12-diol (ilicol) F. oolepis [12] [56]
26 FUUSVPZQXDAJBK-PEUVFPKISA-N 11,13-Dihydro-11-hydroxycostol F. heterolepis [54]
27 LKKDASYGWYYFIK-QHSBEEBCSA-N Cryptomeridiol F. resinosa [59] [61]
28 BOPIMTNSYWYZOC-ILWWEHDPSA-N b-Eudesmol F. resinosa [61]
29 CJJVWDBBCWOEJB-NWJSVONSSA-N 1-Oxoisoalantolactone F. macrophylla [55]
30 ZALRIXVWAYTYQJ-MUGBGTHKSA-N 4b-Hydroxy-4,10a-dimethyl-7aH,8aH-eudesm- F. riparia [24]
11-ene-12,8-olide
Table 2 (cont.)

31 ZALRIXVWAYTYQJ-URFZWBKFSA-N Septuplinolide F. riparia [24]
32 WICFVILDTXFJOU-KDBYPZKRSA-N 9a-Hydroxyisoalantolactone F. macrophylla [55]
33 WICFVILDTXFJOU-MCZMQQNQSA-N 9b-Hydroxyisoalantolactone F. macrophylla [55]
34 FQQMEEUJSSWHAI-YXMPFFBPSA-N 9-Oxoisoalantolactone F. macrophylla [55]
35 CVUANYCQTOGILD-QVHKTLOISA-N Isoalantolactone F. riparia [24] [53]
36 PXOYOCNNSUAQNS-AGNJHWRGSA-N Alantolactone F. macrophylla [55]
37 NGIVKZGKEPRIGG-AWEZNQCLSA-N g-Curcumene F. macrophylla [55]
38 VMYXUZSZMNBRCN-AWEZNQCLSA-N a-Curcumene F. macrophylla [55]
39 FDUZTAGLNCBNSN-UHFFFAOYSA-N (¢)-Hamanasic acid A F. campestris [9]
40 AGIQIKMGJVLKMA-GZVHEFRTSA-N Carabrone F. riparia [24] [ 53]
41 PEYLVIRXSYMEHY-CCCRVJQASA-N Flourensadiol F. cernua, F. resinosa [21] [29] [30] [61]
42 KEAQXGKBWOHMKS-QFEQQRJNSA-N Spathulenol F. resinosa [61]
Flavonoids
43 RTIXKCRFFJGDFG-UHFFFAOYSA-N Chrysin F. resinosa [59] [60] [61]
44 IRZVHDLBAYNPCT-UHFFFAOYSA-N 7-O-Methylchrysin (tectochrysin) F. resinosa [60] [61]
45 KZNIFHPLKGYRTM-UHFFFAOYSA-N Apigenin F. resinosa [60]
46 JPMYFOBNRRGFNO-UHFFFAOYSA-N 7-O-Methylapigenin F. resinosa [60]
47 DANYIYRPLHHOCZ-UHFFFAOYSA-N 4’-O-Methylapigenin F. resinosa [60]
48 LZERJKGWTQYMBB-UHFFFAOYSA-N 4’,7-O-Dimethylapigenin F. resinosa [60]
49 IHFBPDAQLQOCBX-UHFFFAOYSA-N 4’,5,7-Trihydroxy-6-methoxyflavone (hispidulin) F. cernua [27]
50 ZIIAJIWLQUVGHB-UHFFFAOYSA-N 4’,5-Dihydroxy-6,7-dimethoxyflavone (cirsimaritin) F. cernua [31]
51 FIAAVMJLAGNUKW-VQVVXJKKSA-N 6,8-Di-C-b-d-glucosylapigenin (vicenin-2) F. cernua [31]
52 OVMFOVNOXASTPA-MCIQUCDDSA-N 8-C-b-d-Glucosyl-6-C-b-d-xylosylapigenin F. cernua [31]

(vicenin-1)
53 OVMFOVNOXASTPA-VYUBKLCTSA-N 6-C-a-l-Arabinosyl-8-C-b-d-glucosylapigenin F. cernua [31]
(isoschaftoside)
54 MMDUKUSNQNWVET-VYUBKLCTSA-N 8-C-a-l-Arabinosyl-6-C-b-d-glucosylapigenin F. cernua [31]
(schaftoside)
55 MMDUKUSNQNWVET-LQYCTPBQSA-N 8-C-b-l-Arabinosyl-6-C-b-d-glucosylapigenin F. cernua [31]
(neoschaftoside)
56 VCCRNZQBSJXYJD-UHFFFAOYSA-N Galangin F. resinosa [60]
1603
Table 2 (cont.)
1604

57 PVJNLMXWZXXHSZ-UHFFFAOYSA-N 7-O-Methylgalangin F. resinosa [60]
58 OGQSUSFDBWGFFJ-UHFFFAOYSA-N 6-Methylgaletin F. ilicifolia [23]
59 REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin F. cernua [48]
60 JGUZGNYPMHHYRK-UHFFFAOYSA-N 7-O-Methylquercetin F. thurifera [7]
61 LYISDADPVOHJBJ-UHFFFAOYSA-N 3-O-Methylgalangin F. resinosa [60]
62 DDNPCXHBFYJXBJ-UHFFFAOYSA-N 3,6-O-Dimethylgaletin F. campestris, F. ilicifolia [23]
63 WEPBGSIAWZTEJR-UHFFFAOYSA-N 3-O-Methylquercetin F. cernua [31]
64 FMEHGPQTMOPUGM-UHFFFAOYSA-N 3,3’-O-Dimethylquercetin F. resinosa [60]
65 VJJZJBUCDWKPLC-UHFFFAOYSA-N 3-O-Methylkaempferol F. ilicifolia, F. resinosa [23] [60]
66 BJBUTJQYZDYRMJ-UHFFFAOYSA-N 3,7-O-Dimethylkaempferol (kumatakenin) F. retinophylla, F. cernua, [23] [31] [60]
F. resinosa
67 RJCJVIFSIXKSAH-UHFFFAOYSA-N 3,4’-O-Dimethylkaempferol (ermanin) F. resinosa, F. cernua [21] [60]
68 XUWTZJRCCPNNJR-UHFFFAOYSA-N 3,3’,6-O-Trimethylquercetagetin (jaceidin) F. ilicifolia [23]
69 KIGVXRGRNLQNNI-UHFFFAOYSA-N 3,6-O-Dimethylquercetagetin F. ilicifolia [23]
70 SWAJPHCXKPCPQZ-AWEZNQCLSA-N (2S)-2,3-Dihydro-7-hydroxy-2-phenyl-4H- F. heterolepis, F. oolepis [54] [56]
1-benzopyran-4-one (7-hydroxyflavanone)
71 VYESEQLQFXUROZ-HNNXBMFYSA-N (2S )-2,3-Dihydro-7-methoxy-2-phenyl-4H- F. heterolepis [54]
1-benzopyran-4-one (7-methoxyflavanone)
72 URFCJEUYXNAHFI-ZDUSSCGKSA-N 5,7-Dihydroxyflavanone (pinocembrine) F. oolepis, F. ilicifolia, [12] [13] [23]
F. retinophylla
73 NJWJQMLMBXIOJW-ZDUSSCGKSA-N 3’,5,7-Trihydroxyflavanone F. retinophylla [62]
74 RRBWQNNVMSQYDT-AWEZNQCLSA-N 5,7-Dihydroxy-3’-methoxyflavanone F. retinophylla [62]
75 SUYJZKRQHBQNCA-LSDHHAIUSA-N (2R,3R)-2,3-Dihydro-3,5,7-trihydroxy-2-phenyl- F. riparia, F. resinosa [24] [60]
4H-1-benzopyran-4-one (pinobankasin)
76 ZMADGMGPOXUDTA-MSOLQXFVSA-N 3’,5,7-Trihydroxy-3-isobutyroylflavanonol F. retinophylla [62]
77 DAWSYIQAGQMLFS-SFHVURJKSA-N Glabranin F. riparia [24]
78 LPEPZZAVFJPLNZ-SFHVURJKSA-N 8-Prenylnaringenin F. riparia [24] [53]
79 ADFZZQAJJGHYDR-IBGZPJMESA-N (2S )-3’,4’,7-Trihydroxy-8-(3-methylbut- F. fiebrigii [52] [53]
2-en-1-yl)flavanone
80 XJUDJFVOICLOMY-SFHVURJKSA-N 8-Prenyleriodictyol F. campestris, F. fiebrigii [24] [52] [53]
81 UZIHIZDYDJGCPV-RITBQAEESA-N (2S )-3’,4’,7-Trihydroxy-8-(4-hydroxy- F. fiebrigii [52]
3-methylbut-2-en-1-yl)flavanone
Table 2 (cont.)

82 QTHZKQQTHZVUHQ-SFHVURJKSA-N 3’,5-Dihydroxy-7-O-methylisobavachin F. heterolepis, F. macro- [24] [52] [53]
phylla, F. campestris, [54] [55]
F. riparia, F. fiebrigii
83 SNPYBALVJUBBHC-PXQOOZMRSA-N (2S )-3’,4’,5-Trihydroxy-8-(4-hydroxy-3- F. fiebrigii [52]
methylbut-2-en-1-yl)-7-methoxyflavanone
84 NSGZYFCJQNNTFB-SFHVURJKSA-N Exiguaflavanone K F. riparia [24] [53]
85 ATJOIGKHVRPLSM-RBUKOAKNSA-N Glepidotin B F. riparia [24] [53]
86 LGBAIPUTDBEARD-VQTJNVASSA-N 8-Prenyldihydroisorhamnetin F. campestris, F. riparia [24] [53]
87 PZXSKZHBJCBTDD-LEWJYISDSA-N Scariosin F. riparia [24] [53]
88 JKAJKGLNEHIVQM-QPEQYQDCSA-N 2-(3,4-Dimethoxyphenyl)-5-hydroxy-6,7- F. macrophylla [55]
dimethoxy-8-[(2Z )-2-methylbut-2-en-1-yl]-
4H-1-benzopyran-4-one
89 PFTAWBLQPZVEMU-DZGCQCFKSA-N Catechin F. cernua [48]
90 JUMSUVHHUVPSOY-RMKNXTFCSA-N (2E )-1-(2,4-Dihydroxyphenyl)-3-phenylprop- F. heterolepis, F. oolepis [54] [56]
2-en-1-one (2’,4’-dihydroxychalcone)
Benzofurans, chromenes, and coumarins
91 SYBFAZVPJPGCDJ-LLVKDONJSA-N 1-[(2R )-2,3-Dihydro-4-methoxy-2-(prop-1-en- F. cernua [32]
2-yl)-1-benzofuran-5-yl]ethanone
92 UVYUUQGGBNKRFU-CYBMUJFWSA-N Tremetone F. fiebrigii [52]
93 FHJSLVLVJPGFRY-GFCCVEGCSA-N 1-[(2R )-2,3-Dihydro-6-hydroxy-2-(1-methyl- F. cernua, F. heterolepis [32] [54]
ethenyl)-5-benzofuranyl]ethanone (dihydroeuparin)
94 IYMJMWNDRCWQPW-GFCCVEGCSA-N 6-Methoxytremetone F. riparia, F. fiebrigii [24] [52] [53]
95 LQUPQVIPBLTZNW-HZIYNJIRSA-N (2Z )-1-[(2R,3S )-5-Acetyl-2,3-dihydro-2-(1-methyl- F. fiebrigii [52]

ethenyl)benzofuran-3-yl]-2-methylbut-2-en-1-one
96 DECAFQNQVVPXBG-YIGKEOEDSA-N (2Z )-1-[(2R,3S )-5-Acetyl-2,3-dihydro-6-hydroxy-2- F. heterolepis, [54] [55]
(1-methylethenyl)benzofuran-3-yl]-2-methylbut- F. macrophylla
2-en-1-one (3a-(angeloyloxy)-6-hydroxytremetone)
97 GIHOQEXRAZGPDD-UZORRUGTSA-N (2Z )-1-[(2R,3S)-5-Acetyl-2,3-dihydro-6-methoxy- F. heterolepis, [54] [55]
2-(1-methylethenyl)benzofuran-3-yl]-2-methylbut- F. macrophylla
2-en-1-one (3a-(angeloyloxy)-6-methoxytremetone)
1605
Table 2 (cont.)
1606

98 KMRYVFPSZZNLIH-JTQKBSHLSA-N Cernuanon angelicate F. cernua [32]
99 HDKIXHWFCJFFGZ-HKUYNNGSSA-N Cernuanon senecioate F. cernua [32]
100 KMRYVFPSZZNLIH-QPXZKVABSA-N Cernuanon trans-2-methyl-2-pentanoate F. cernua [32]
(cernuanon tiglate)
101 YXRSEJIHJWTWJI-FACVGWQGSA-N Cernuanon cinnamate F. cernua [32]
102 SHYHWQIISKJNHX-PZORYLMUSA-N 2,3-Dihydro-11,12-dihydroxyeuparin F. riparia [63]
103 FODXYKLQGZFBND-PZORYLMUSA-N 1-[(2R )-2-(2-Chloro-1-hydroxy-1-methylethyl)- F. riparia [63]
2,3-dihydro-benzofuran-5-yl]ethanone
104 FOXRXAILTBHLQA-UHFFFAOYSA-N Euparone F. riparia [24]
105 QJIYGTAEIRBFIS-UHFFFAOYSA-N 1,1’-(6-Methoxy-1-benzofuran-2,5-diyl)diethanone F. riparia, F. campestris [24]
(6-methyleuparone)
106 OPUFDNZTKHPZHM-UHFFFAOYSA-N 1-[6-Hydroxy-2-(1-methylethenyl)benzofuran- F. thurifera, F. cernua, [7] [32] [54]
5-yl]-ethanone (euparin) F. heterolepis, F. acro- [55] [56]
phylla, F. oolepis
107 XFSSPJGVPRWHLS-UHFFFAOYSA-N 1-[6-Methoxy-2-(1-methylethenyl)benzofuran- F. heterolepis, [54] [55]
5-yl]-ethanone (euparin methyl ether) F. macrophylla
108 PWNKMOTZMPCIOS-GHXNOFRVSA-N Flourensianol angelicate F. cernua, F. resinosa [32]
109 IFCUKUZRARUXJK-UHFFFAOYSA-N Flourensianol senecioate F. resinosa [32]
110 PWNKMOTZMPCIOS-KPKJPENVSA-N Flourensianol tiglate F. resinosa [32]
111 WXVLCNREBFDEKS-UHFFFAOYSA-N Encecalin F. thurifera, F. riparia [7] [24]
112 ZAJTXVHECZCXLH-UHFFFAOYSA-N 6-Acetyl-2,2-dimethyl-2H-1-benzopyran F. thurifera, F. cernua, [7] [32] [54]
(demethylencecalin) F. heterolepis
113 WFXJDXJXOHZQRD-UHFFFAOYSA-N 1-[2,2-Dimethyl-8-(3-methylbut-2-en-1-yl)- F. cernua, F. heterolepis, [32] [54] [55]
2H-1-benzopyran-6-yl]ethanone (deoxodehydro- F. macrophylla

cyclopiloselloidone)
114 SVUVYHFYZBCYRF-UHFFFAOYSA-N 1-(7-Hydroxy-2,2-dimethyl-2H-1-benzopyran- F. cernua, F. heterolepis [32] [54]
6-yl)ethanone
(desmethylencecalin; eupatoriochromene)
115 ZMQPULSGBXIVGC-SECBINFHSA-N (1R )-1-(7-Methoxy-2,2-dimethyl-2H-chromen- F. cernua, F. heterolepis [32] [54]
6-yl)ethanol (encecalinol)
Table 2 (cont.)

116 LMQFQBUKMWFFNL-FFXRNRBCSA-N (1R )-1-(7-Methoxy-2,2-dimethyl-2H-chromen- F. cernua [32]
6-yl)ethyl (2Z )-2-methylbut-2-enoate
(encecalinol angelate)
117 VUQDDBFLZLQVBH-UHFFFAOYSA-N 1-(5-Hydroxy-8-methoxy-2,2-dimethyl-2H- F. cernua [32]
chromen-6-yl)ethanone
118 RRUFTPKJXNXMAE-UHFFFAOYSA-N 6-Ethenyl-7-methoxy-2,2-dimethyl-2H-chromene F. cernua [32]
(anhydroencecalinol)
119 AWEFUQDNSBBNCR-UHFFFAOYSA-N Prenyletin F. thurifera [7]
120 ZLPLFUBVEZVYDX-UHFFFAOYSA-N Prenyletin-6-methyl ether (scopoletin-(3-methyl- F. thurifera, [7] [55]
but-2-en-1-yl) ether) F. macrophylla
121 QJZRVRVZRIXGMR-UHFFFAOYSA-N Capensin F. thurifera [7]
122 RODXRVNMMDRFIK-UHFFFAOYSA-N Scopoletin F. riparia, [53] [55]
F. macrophylla
123 GUAFOGOEJLSQBT-UHFFFAOYSA-N Scoparone F. macrophylla [55]
Aromatic derivatives
124 XVTRUNNIGJWXKK-UHFFFAOYSA-N 1-[4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)- F. cernua, F. hetero- [32] [54] [55]
phenyl]ethanone lepis, F. macrophylla
125 BXENSVBWXKDKHS-IUXPMGMMSA-N 4-Acetyl-2,6-bis(3-methylbut-2-en-1-yl)phenyl F. heterolepis [54]
(2Z )-2-methylbut-2-enoate
126 TXFPEBPIARQUIG-UHFFFAOYSA-N 1-(4-Hydroxyphenyl)ethanone (p-acetophenol) F. riparia, F. hetero- [24] [54] [55] [61]
lepis, F. macrophylla,
F. resinosa
127 QJAPFSSVKIZTMR-UHFFFAOYSA-N 1-[3-(3-Methylbut-2-en-1-yl)phenyl]ethanone F. cernua [32]

128 SXPHHWILAWXFLE-UHFFFAOYSA-N 1-(3-Acetylphenyl)-3-methylbutan-1-one F. cernua [32]
129 YODPVTWQOQASPC-BQYQJAHWSA-N 1-{3-[(1E )-3-Hydroxy-3-methylbut-1-en-1-yl]- F. cernua [32]
4-methoxyphenyl}ethanone
130 HZKNHDLUFBYIQN-VMPITWQZSA-N (2E )-3-[4-Hydroxy-3-(3-methylbut-2-en-1-yl)- F. thurifera, [7] [54]
phenyl]prop-2-enoic acid (drupanin) F. heterolepis
131 KABCFARPAMSXCC-JXMROGBWSA-N (2E )-3-[4-Hydroxy-3,5-bis(3-methylbut-2-en-1-yl)- F. heterolepis [54]
phenyl]prop-2-enoic acid (artepillin C )
1607
Table 2 (cont.)
1608

132 OYJOYSKCSSWMJZ-GQHUZBHDSA-N Methyl (2E)-3-{4-hydroxy-3-[(2E )-4-hydroxy- F. thurifera [7]
3-methylbut-2-en-1-yl]phenyl}prop-2-enoate
133 NCCWCZLEACWJIN-UHFFFAOYSA-N Methyl orsellinate F. cernua [21]
134 AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid F. cernua [43]
135 WBYWAXJHAXSJNI-VOTSOKGWSA-N Cinnamic acid F. cernua [48]
136 FBSFWRHWHYMIOG-UHFFFAOYSA-N Methyl gallate F. cernua [48]
Lupane triterpenes
137 ASFHKKDANFQBBP-MHIFOCCPSA-N 20,29-Epoxy-20,29-dihydrolupenone F. heterolepis, [54] [55]
F. macrophylla
138 VSPYYMPPGGHPKR-VAURRCOBSA-N 20,29-Epoxylupeol F. heterolepis, [54] [55]
F. macrophylla
139 YCUILYGCCUZGPR-LKGNWMIFSA-N 20,29-Epoxy-20,29-dihydro-22a-hydroxylupenone F. heterolepis [54]
140 ZUBZPUNHXGLZSQ-BHMAJAPKSA-N 30-Hydroxylupenone F. heterolepis, [54] [55]
F. macrophylla
141 ZNUAKACHFYTNFX-QGTGJCAVSA-N 30-Hydroxylupeol F. heterolepis [54]
142 GWEFGERHXLEOFD-XKUCDKBTSA-N 3-Oxolupen-12b-ol (resinone) F. resinosa [59]
143 MQYXUWHLBZFQQO-QGTGJCAVSA-N Lupeol F. resinosa [59] [61]
144 BYSDTXPKWFYQDM-ONAXBPCTSA-N 11-Oxo-3-epilupeol F. resinosa [59]
Aliphatic lactones and acetilenes
145 AFZOXJCUHIZZDU-HSZRJFAPSA-N Tetracosan-4-olide F. cernua [21]
146 FLVQHDPEFVLJND-XMMPIXPASA-N Pentacosan-4-olide F. cernua [21]
147 KWOWNYUWWHKUCK-RUZDIDTESA-N Hexacosan-4-olide F. cernua [21]
148 RATVVPKFLMJAST-AREMUKBSSA-N Heptacosan-4-olide F. cernua [21]

149 JBDGMANPHCRIOU-HHHXNRCGSA-N Octacosan-4-olide F. cernua [21]
150 BYWVQXXACNFXHT-MUUNZHRXSA-N Nonacosan-4-olide F. cernua [21]
151 YLLQOTIGQVCOEH-GDLZYMKVSA-N Triacontan-4-olide F. cernua [21]
152 KKBHBCOJHHCOCL-UHFFFAOYSA-N Tridec-1-ene-3,5,7,9,11-pentayne F. cernua, F. heterolepis [32] [54]
153 PXQLZFYDZKYLPY-FNORWQNLSA-N Trideca-1,3-diene-5,7,9,11-tetrayne F. cernua, F. resinosa, [32] [54]
F. heterolepis
154 AJWRNFIZKHPOHC-JEGFTUTRSA-N Trideca-1,3,5-triene-7,9,11-triyne F. heterolepis [54]
155 WWKACWAQDXLZAV-BNFZFUHLSA-N Tetradeca-4,6-diene-8,10,12-triyn-1-ol F. cernua [32]
Table 2 (cont.)

156 ANIAOEHACLPLEY-UHFFFAOYSA-N 2-( But-3-en-1-yn-1-yl)-5-(penta-1,3-diyn-1-yl)- F. cernua [32]
thiophene (thiophene B )
Miscellaneous compounds
157 ITKPHNFJAMQBFT-UHFFFAOYSA-N 1,3-Arachidobehenicin F. cernua [29]
158 KZJWDPNRJALLNS-VJSFXXLFSA-N b-Sitosterol F. resinosa [61]
159 REZQBEBOWJAQKS-UHFFFAOYSA-N Triacontan-1-ol F. resinosa [61]
160 UQXWAKWFOLVCKE-RTNGKITGSA-N Squalene F. resinosa [61]
Essential oils
26 LKKDASYGWYYFIK-QHSBEEBCSA-N Cryptomeridiol F. cernua [20] [61]
28 QXRKIZKJLNNMNC-VYHDIPPYSA-N b-Eudesmol F. campestris, F. cernua, [9] [17] [20] [35]
F. oolepis [57] [61]
37 NGIVKZGKEPRIGG-AWEZNQCLSA-N g-Curcumene F. cernua [17] [35]
41 PEYLVIRXSYMEHY-CCCRVJQASA-N Flourensadiol F. cernua [17] [35] [36]
42 KEAQXGKBWOHMKS-QFEQQRJNSA-N Spathulenol F. thurifera, F. campestris, [8] [9] [15] [20]
F. oolepis, F. cernua, [35] [61]
F. resinosa
161 MBDOYVRWFFCFHM-SNAWJCMRSA-N (2E )-Hex-2-enal F. cernua [35]
162 UHEPJGULSIKKTP-UHFFFAOYSA-N 6-Methylhept-5-en-2-one F. cernua [35]
163 ZCHOPXVYTWUHDS-WAYWQWQTSA-N (3Z )-Hex-3-en-1-yl butanoate F. cernua [35]
164 AUHZEENZYGFFBQ-UHFFFAOYSA-N Mesitylene F. cernua [20]
165 ZQGDEJAPCUGBRH-UHFFFAOYSA-N Santolinetriene F. oolepis, F. cernua [15] [17] [20] [35]
166 ZQGDEJAPCUGBRH-UHFFFAOYSA-N Artemisiatriene F. cernua [35]
167 WPPVSYVQAKQNJK-VIFPVBQESA-N Artemisia alcohol F. cernua [17] [20] [35]

168 OTYVBQZXUNBRTK-UHFFFAOYSA-N Artemisia ketone F. cernua [17] [20] [35]
169 CSMMFGCGBLZIJE-BQYQJAHWSA-N Yomogi alcohol F. cernua [20] [35]
170 XJPBRODHZKDRCB-CSKARUKUSA-N a-Ocimene F. thurifera [8]
171 IHPKGUQCSIINRJ-CSKARUKUSA-N ( E)-b-Ocimene F. cernua [17] [20] [35]
172 IHPKGUQCSIINRJ-NTMALXAHSA-N ( Z)-b-Ocimene F. cernua, F. oolepis [17] [20] [35] [57]
173 GQVMHMFBVWSSPF-DAIHKBMKSA-N Neoalloocimene F. cernua [20]
174 UAHWPYUMFXYFJY-UHFFFAOYSA-N b-Myrcene F. cernua [17] [33] [35] [36]
1609
Table 2 (cont.)
1610

175 CDOSHBSSFJOMGT-JTQLQIEISA-N Linalool F. thurifera, F. cernua, [8] [35] [57]
F. oolepis
176 HIGQPQRQIQDZMP-FLIBITNWSA-N Neryl acetate F. cernua [35]
177 FQTLCLSUCSAZDY-ATGUSINASA-N ( E)-Nerolidol (trans-nerolidol) F. cernua [35] [36]
178 BOTWFXYSPFMFNR-PYDDKJGSSA-N 3,7,11,15-Tetramethylhexadec-2-en-1-ol (phytol) F. thurifera, F. cernua [8] [17]
179 KEVYVLWNCKMXJX-LEAGNCFPSA-N Isophytol F. thurifera [8]
180 YYGNTYWPHWGJRM-AAJYLUCBSA-N Squalene F. oolepis [15]
181 XMLSXPIVAXONDL-PLNGDYQASA-N cis-Jasmone F. cernua [17] [20] [33] [35]
[36]
182 GEWDNTWNSAZUDX-WQMVXFAESA-N Methyl ( Z )-epijasmonate F. cernua [20]
183 GEWDNTWNSAZUDX-NRFYAWERSA-N Methyl ( Z )-jasmonate F. cernua [20] [35]
184 OGCGGWYLHSJRFY-SECBINFHSA-N a-Campholenal F. cernua [20]
185 BRHDDEIRQPDPMG-PSASIEDQSA-N cis-Linalool oxide F. cernua [35]
186 XMGQYMWWDOXHJM-SNVBAGLBSA-N Limonene F. cernua, F. oolepis, [8] [15] [17] [20]
F. thurifera [33] [35] [36] [57]
187 SCWPFSIZUZUCCE-UHFFFAOYSA-N p-Mentha-1(7),3-diene F. thurifera [8]
188 LFJQCDVYDGGFCH-JTQLQIEISA-N b-Phellandrene F. oolepis [57]
189 CIPXOBMYVWRNLL-UHFFFAOYSA-N Isoterpinolene (p-mentha-2,4(8)-diene) F. cernua [17] [35]
190 MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene F. campestris, F. cernua [9] [17] [20] [35]
191 OGLDWXZKYODSOB-SNVBAGLBSA-N a-Phellandrene F. cernua [17] [35]
192 YHQGMYUVUMAZJR-UHFFFAOYSA-N a-Terpinene F. cernua [17] [20] [35]
193 YKFLAYDHMOASIY-UHFFFAOYSA-N g-Terpinene F. cernua [20] [35]
194 XNMPFDIYAMOYRM-UHFFFAOYSA-N p-Mentha-1,3,8-triene F. cernua [35]
195 IZXYHAXVIZHGJV-NXEZZACHSA-N cis-p-Menth-2-en-1-ol F. cernua [20]

196 WRYLYDPHFGVWKC-JTQLQIEISA-N Terpinen-4-ol F. cernua [17] [20] [35]
197 WUOACPNHFRMFPN-SECBINFHSA-N a-Terpineol F. cernua, F. oolepis [15] [20] [35]
198 – m-Terpineol F. oolepis [15]
199 FZXLDENMTYEVAD-ZJUUUORDSA-N trans-Carveol F. cernua [35]
200 WWRCMNKATXZARA-UHFFFAOYSA-N o-Cymene F. oolepis, F. cernua [15] [17]
201 XCYJPXQACVEIOS-UHFFFAOYSA-N m-Cymene F. cernua [36]
202 HFPZCAJZSCWRBC-UHFFFAOYSA-N p-Cymene F. cernua, F. oolepis [17] [20] [35]
[36] [57]
Table 2 (cont.)

203 NARIBLVZTLPQJB-UHFFFAOYSA-N m-Cymen-8-ol F. cernua [20] [35]
204 XLPDVYGDNRIQFV-UHFFFAOYSA-N p-Cymen-8-ol F. cernua [20] [35]
205 RECUKUPTGUEGMW-UHFFFAOYSA-N Carvacrol F. cernua [20]
206 WTWBUQJHJGUZCY-UHFFFAOYSA-N Cuminaldehyde F. cernua [35]
207 NDVASEGYNIMXJL-UWVGGRQHSA-N Sabinene F. cernua, F. oolepis [17] [20] [35] [36]
[57]
208 KQAZVFVOEIRWHN-UWVGGRQHSA-N a-Thujene (3-thujene) F. cernua, F. oolepis, [8] [15] [17] [20]
F. thurifera [35] [57]
209 LBVRQJWOZIMWNY-UWVGGRQHSA-N Thuja-2,4(10)-diene F. cernua [35]
210 KXSDPILWMGFJMM-GUBZILKMSA-N cis-Sabinene hydrate F. cernua [20] [35]
211 KXSDPILWMGFJMM-AEJSXWLSSA-N trans-Sabinene hydrate F. cernua [20] [35]
212 BQOFWKZOCNGFEC-BDAKNGLRSA-N d-3-Carene F. cernua, F. oolepis [15] [17] [20] [33]
[35] [36]
213 GRWFGVWFFZKLTI-UHFFFAOYSA-N a-Pinene F. thurifera, [8] [9] [15] [17]
F. campestris, [20] [35] [36]
F. oolepis, F. cernua
214 WTARULDDTDQWMU-UHFFFAOYSA-N b-Pinene F. thurifera, [8] [9] [15] [17]
F. campestris, [20] [35] [36] [57]
F. cernua, F. oolepis
215 LCYXQUJDODZYIJ-VGMNWLOBSA-N trans-Pinocarveol F. cernua [17] [20] [35]
216 TZDMGBLPGZXHJI-JGVFFNPUSA-N Pinocarvone F. cernua [20]
217 WONIGEXYPVIKFS-DJLDLDEBSA-N trans-Verbenol F. cernua [20] [35]
218 IRZWAJHUWGZMMT-YIZRAAEISA-N cis-Chrysanthenol F. cernua [17] [20]
219 UASZOTVHPVEMQR-AXFHLTTASA-N cis-Chrysanthenyl acetate F. cernua [20]

220 RXBQNMWIQKOSCS-IUCAKERBSA-N Myrtenol F. cernua [20] [35]
221 KMRMUZKLFIEVAO-IUCAKERBSA-N Myrtenal F. cernua [20]
222 MOILFCKRQFQVFS-BGPATTHWSA-N (þ)-2,6,6-Trimethyl-bicyclo[3.1.1]hept-2-ene F. oolepis [15]
223 CRPUJAZIXJMDBK-UHFFFAOYSA-N Camphene F. cernua, F. oolepis [17] [20] [33] [35]
[36] [57]
224 DSSYKIVIOFKYAU-UHFFFAOYSA-N Camphor F. cernua [17] [20] [35] [36]
225 DTGKSKDOIYIVQL-UHFFFAOYSA-N Isoborneol F. cernua [20] [35]
1611
Table 2 (cont.)
1612

226 DTGKSKDOIYIVQL-UHFFFAOYSA-N Borneol F. cernua [17] [20] [33] [35]
[36]
227 KGEKLUUHTZCSIP-UHFFFAOYSA-N Bornyl acetate F. cernua [20]
228 WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-Cineole F. cernua, F. thurifera [8] [17] [20] [33]
[35] [36]
229 RRBYUSWBLVXTQN-UHFFFAOYSA-N Tricyclene F. cernua [17] [20] [35]
230 RGZSQWQPBWRIAQ-CABCVRRESA-N a-Bisabolol F. cernua [20] [35]
231 RGZSQWQPBWRIAQ-GJZGRUSLSA-N epi-a-Bisabolol F. oolepis [57]
232 FKWGCEDRLNNZOZ-GFCCVEGCSA-N Xanthorrizol F. cernua [35]
233 JXZQZARENYGJMK-CQSZACIVSA-N b-Curcumene F. cernua [35]
234 GXEGJTGWYVZSNR-JEKCHIPQSA-N Germacrene B F. thurifera, F. cam- [8] [9] [17] [35]
pestris, F. cernua
235 GAIBLDCXCZKKJE-RXJOXMPGSA-N Germacrene D F. thurifera, F. cernua, [8] [17] [20]
F. oolepis [35] [57]
236 RHCTXHCNRLCYBN-QPDMSNBJSA-N Germacrene D-4-ol F. cernua [20] [35]
237 CAULGCQHVOVVRN-UPAULDTKSA-N Germacrone F. oolepis [57]
238 FAMPSKZZVDUYOS-PGPZXUPKSA-N a-Caryophyllene, a-humulene F. thurifera, [8] [9] [15] [20]
F. campestris, [35] [57]
239 OPFTUNCRGUEPRZ-RRFJBIMHSA-N b-Elemene F. oolepis [57]
240 BQSLMQNYHVFRDT-CABCVRRESA-N g-Elemene F. oolepis [57]
241 JLAMFILROHVNBN-CABCVRRESA-N d-Elemene F. cernua, F. oolepis [17] [35] [57]
242 – t-Elemene F. oolepis [15]
243 GFJIQNADMLPFOW-VNHYZAJKSA-N Elemol F. cernua [20] [35]

244 YMBFCQPIMVLNIU-SOUVJXGZSA-N trans-a-Bergamotene F. cernua [17] [35]
245 JGINTSAQGRHGMG-NLJYZETGSA-N ( Z)-a-trans-Bergamotol F. oolepis [15]
246 RAQGTGHVNNVNBQ-LSDHHAIUSA-N a-Acoradiene F. cernua [35]
247 KBMDEJULGPFFGC-SNPRPXQTSA-N b-Acoradienol F. cernua [20]
248 ICWHTQRTTHCUHW-GZBFAFLISA-N Hinesol F. cernua [35]
249 FITHEODIIYWPLM-UHFFFAOYSA-N 4-Ethenyl-4,8,8-trimethyl-2-methylidenebicyclo- F. oolepis [15]
[5.2.0]nonane
Table 2 (cont.)

250 NPNUFJAVOOONJE-GFUGXAQUSA-N b-Caryophyllene F. thurifera, F. campestris, [8] [9] [17] [20]
F. cernua, F. oolepis [33] [35] [57]
251 NVEQFIOZRFFVFW-RGCMKSIDSA-N Caryophyllene oxide F. campestris, F. oolepis, [9] [15] [17] [20]
F. cernua [33] [35] [36]
252 VPDZRSSKICPUEY-JEPMYXAXSA-N Bicyclogermacrene F. campestris, F. cernua [9] [17] [20] [35]
253 YKWVCZPTAAKDIY-XQLPTFJDSA-N b-Oplopenone F. cernua [20] [35]
254 LKQMMFFQYMYQOJ-COMQUAJESA-N Bicycloelemene F. campestris [9]
255 AVICQHVWKPMCNK-DZGCQCFKSA-N Drima-7,9(11)-diene F. cernua [20] [35]
256 BBAMLNIPVMLTSQ-VNHYZAJKSA-N Himachalol F. cernua [35]
257 JUQGWBAOQUBVFP-UHFFFAOYSA-N 1,2,3,4,4a,7-Hexahydro-1,6-dimethyl- F. oolepis [15]
4-(1-methylethyl)naphthalene
258 QMAYBMKBYCGXDH-ZNMIVQPWSA-N a-Muurolene F. oolepis, F. cernua [15] [20] [35]
259 QMAYBMKBYCGXDH-KFWWJZLASA-N Amorphene F. campestris [9]
260 USDOQCCMRDNVAH-ZNMIVQPWSA-N b-Muurolene F. oolepis [15]
261 WRHGORWNJGOVQY-QLFBSQMISA-N g-Muurolene F. cernua,F. oolepis [17] [20] [35] [36]
[57]
262 WRHGORWNJGOVQY-ZNMIVQPWSA-N t-Muurolene F. oolepis [15]
263 LHYHMMRYTDARSZ-CBBWQLFWSA-N epi-a-Muurolol F. cernua [20] [35]
264 QMAYBMKBYCGXDH-KKUMJFAQSA-N a-Cadinene F. thurifera, F. cernua, [8] [35] [57]
F. oolepis
265 USDOQCCMRDNVAH-KKUMJFAQSA-N b-Cadinene F. cernua [35]
266 WRHGORWNJGOVQY-KKUMJFAQSA-N g-Cadinene F. thurifera, F. cernua, [8] [17] [20] [35]
F. oolepis [57]
267 FUCYIEXQVQJBKY-ZFWWWQNUSA-N d-Cadinene F. campestris, [9] [15] [17] [20]

F. cernua, F. oolepis [35] [57]
268 – t-Cadinene F. oolepis [15]
269 IRTLNNMZFREJRK-CNSWMUILSA-N Cadina-1,4-diene F. cernua [17] [20] [35]
270 LHYHMMRYTDARSZ-XQLPTFJDSA-N t-Cadinol F. oolepis [57]
271 COGPRPSWSKLKTF-CBBWQLFWSA-N Cubenol F. oolepis, F. cernua [15] [35]
272 COGPRPSWSKLKTF-QPSCCSFWSA-N 1-Epicubenol F. cernua [20] [35]
273 LHYHMMRYTDARSZ-BYNSBNAKSA-N a-Cadinol F. campestris, F. oolepis [9] [57]
274 LHYHMMRYTDARSZ-AJNGGQMLSA-N t-Muurolol F. oolepis [57]
1613
Table 2 (cont.)
1614

275 PGTJIOWQJWHTJJ-STQMWFEESA-N cis-Calamenene F. cernua, F. oolepis [20] [35] [57]
276 CUUMXRBKJIDIAY-ZDUSSCGKSA-N a-Calacorene F. cernua, F. oolepis [35] [57]
277 YOVSPTNQHMDJAG-QLFBSQMISA-N b-Selinene F. thurifera, [8] [9] [17] [20]
F. campestris, [35] [57]
278 WMOPMQRJLLIEJV-IUODEOHRSA-N g-Eudesmol F. cernua, F. oolepis [35] [57]
279 KZFZFOJVXABAIJ-GZBFAFLISA-N Eremophilene F. oolepis [15]
280 FCSRUSQUAVXUKK-VNHYZAJKSA-N a-Eudesmol F. cernua [35]
281 FCSRUSQUAVXUKK-KCQAQPDRSA-N 7-Epi-a-eudesmol F. cernua [35]
282 WMOPMQRJLLIEJV-DOMZBBRYSA-N 10-Epi-g-eudesmol F. cernua [35]
283 ZLQADKTVJQXDIG-SNPRPXQTSA-N Agarofuran F. campestris [9]
284 WTOYNNBCKUYIKC-JMSVASOKSA-N Nootkatone F. cernua [20] [35]
285 ITRHZWKEZJYJQO-UHFFFAOYSA-N 2-(1,2,3,4,4a,5,6,7-Octahydro-4a,8-dimethyl- F. oolepis [15]
naphthalen-2-yl)prop-2-en-1-ol
286 DYEQPYSFRWUNNV-LJISPDSOSA-N Selinane F. oolepis [15]
287 VEGYMPQCXPVQJY-OAHLLOKOSA-N d-Selinene F. cernua [35]
288 WNRBYZQFEBIUGD-LSDHHAIUSA-N Selina-3,7(11)-diene F. thurifera [8]
289 DPQYOKVMVCQHMY-KBUPBQIOSA-N Selin-11-en-4a-ol F. cernua [20] [35]
290 GIBQERSGRNPMEH-RYUDHWBXSA-N cis-b-Guaiene F. cernua [17] [35]
291 DUYRYUZIBGFLDD-AAVRWANBSA-N g-Gurjunene F. oolepis [15]
292 ADIDQIZBYUABQK-VYAYZGMFSA-N a-Guaiene or aromadendrene F. campestris, [9] [15] [17] [35]
F. cernua, F. oolepis [57]
293 LGOFSGDSFQNIAT-SCRDCRAPSA-N Bulsenol F. cernua [20] [35]
294 FWKQNCXZGNBPFD-UHFFFAOYSA-N Guajazulene F. oolepis [15]

295 OXBYVYGWWRTWMD-XVIXHAIJSA-N Dehydroaromadendrene F. oolepis [15]
296 ITYNGVSTWVVPIC-DHGKCCLASA-N Alloaromadendrene F. campestris, [8] [9] [15] [20]
F. thurifera, [57]
297 WGTRJVCFDUCKCM-FMKGYKFTSA-N Viridiflorene (ledene) F. cernua [17] [35] [36]
298 AYXPYQRXGNDJFU-IMNVLQEYSA-N Ledol F. cernua [20] [35]
299 SPCXZDDGSGTVAW-XIDUGBJDSA-N a-Gurjunene F. cernua [36]
300 AYXPYQRXGNDJFU-RWXDJMAFSA-N Viridiflorol F. cernua [35]
Table 2 (cont.)

301 VQYDOWYUCVQHJM-IWLLMASTSA-N Ledene oxide ( II ) F. oolepis [15]
302 AYXPYQRXGNDJFU-QTPLKFIXSA-N Globulol F. campestris, [9] [33] [57]
F. cernua,
F. oolepis
303 IRAQOCYXUMOFCW-OSFYFWSMSA-N a-Cedrene F. cernua, F. oolepis [17] [35] [57]
304 PPTXKCYXNDLKTQ-FQKPHLNHSA-N Cedr-8-en-13-ol F. oolepis, F. cernua [15] [35]
305 SVURIXNDRWRAFU-OGMFBOKVSA-N Cedrol F. oolepis [57]
306 XUEHVOLRMXNRKQ-KHMAMNHCSA-N a-Cubebene F. thurifera, [8] [15] [17] [20]
F. oolepis, F. cernua [35]
307 FSRZGYRCMPZNJF-KHMAMNHCSA-N b-Cubebene F. thurifera, F. cernua, [8] [20] [35] [57]
F. oolepis
308 KONGRWVLXLWGDV-DEPYFDJDSA-N Epicubebol F. cernua [20] [35]
309 VLXDPFLIRFYIME-QRTUWBSPSA-N a-Ylangene F. cernua [17] [35]
310 VLXDPFLIRFYIME-BTFPBAQTSA-N a-Copaene F. thurifera, [8] [9] [15] [17]
F. campestris, [20] [35] [36] [57]
311 YIRAHEODBQONHI-ZQNQSHIBSA-N b-Bourbonene F. cernua [17] [20] [35]
312 MBIPADCEHSKJDQ-MUYACECFSA-N Aristol-1(10)-ene F. thurifera [8]
313 MBIPADCEHSKJDQ-ADBWKJQBSA-N Calarene F. cernua [36]
314 FOBXOZMHEKILEY-ADBWKJQBSA-N Aristolene F. thurifera [8]
315 UPGLJTCDRBIZKP-ABIUDSBCSA-N b-Maalinene F. campestris [9]
316 HICYDYJTCDBHMZ-COMQUAJESA-N a-Longipinene F. oolepis [15]
317 XBWACJDEQIZTPR-QRMVSZBLSA-N Cyclosativene F. cernua [17] [20] [35]
318 NNBZCPXTIHJBJL-MGCOHNPYSA-N trans-Decahydronaphthalene F. cernua [20]

319 DTUQWGWMVIHBKE-UHFFFAOYSA-N Phenylacetaldehyde F. cernua [35]
320 RRAFCDWBNXTKKO-UHFFFAOYSA-N Eugenol F. cernua [20]
321 ZYEMGPIYFIJGTP-UHFFFAOYSA-N Methyl eugenol F. cernua [20]
322 RFNNKKXNDZWUCP-UHFFFAOYSA-N 1-[6-Hydroxy-2-(1-methylethenyl)- F. oolepis [15]
7-benzofuranyl]ethanone
323 FIGVVZUWCLSUEI-UHFFFAOYSA-N Tricosanoic acid F. thurifera [8]
324 POOSGDOYLQNASK-UHFFFAOYSA-N Tetracosanoic acid F. thurifera [8]
325 YKNWIILGEFFOPE-UHFFFAOYSA-N Pentacosanoic acid F. thurifera [8]
1615
1616
Table 2 (cont.)

326 HMSWAIKSFDFLKN-UHFFFAOYSA-N Hexacosanoic acid F. thurifera [8]
327 BJQWYEJQWHSSCJ-UHFFFAOYSA-N Heptacosanoic acid F. thurifera [8]
328 ZYURHZPYMFLWSH-UHFFFAOYSA-N Octacosanoic acid F. thurifera [8]
329 IGGUPRCHHJZPBS-UHFFFAOYSA-N Nonacosanoic acid F. thurifera [8]
330 JXTPJDDICSTXJX-UHFFFAOYSA-N Triacontanoic acid F. thurifera [8]
331 IUJAMGNYPWYUPM-UHFFFAOYSA-N Hentriacontanoic acid F. thurifera [8]
332 QHMGJGNTMQDRQA-UHFFFAOYSA-N Dotriacontanoic acid F. thurifera [8]
and 28), a tertiary alcohol (16, 25, and 27), or a Me group (17, 18, and 24), while C(11)
includes a CH2 or Me group, or a tertiary alcohol. Costic acids (1 – 15 and 19 – 24),
alantolactone derivatives (29 – 36), and bisabolane sesquiterpenes (37 – 39) are
common, and until now have been exclusively isolated from the South American
species F. heterolepis, F. macrophylla, F. thurifera, and F. riparia, while the flourensic
acid derivatives (17 and 18), cryptomeridiol (27), b-eudesmol (28), flourensiadiol (41),
and spathulenol (42) appear to derive from the North American species F. cernua and
F. resinosa. The isolation of structurally related eudesmane sesquiterpenes 1 – 36 from
F. campestris, F. cernua, F. heterolepis, F. macrophylla, F. oolepis, F. riparia, and F.
thurifera indicate that all these plants possess similar biogenetics, with differentiation
toward lactones in certain South American species. Sesquiterpene lactones are typical
compounds that have constantly been isolated from Asteraceae. These compounds
exhibit specific structural characteristics almost exclusively from this family [65].
Lactones are the second most important group of the eudesmane sesquiterpenes in
Flourensia, which are derived from the cyclization of the HO¢C(9) and the
C(13)OOH. Sesquiterpenes, structurally related to ilicic acid (16) and ilicol (25), have
also been isolated from this species, although much less frequently. South American
species of Flourensia appear to have its biosynthetic machinery preferentially directed
toward sesquiterpene synthesis (Fig. 2).
2.2. Flavonoids. All eleven chemically analyzed Flourensia species until now
contain flavonoids. Forty-eight of these natural products have been isolated from this
genus. The flavonoid profile of these Flourensia plants consists of 13 flavones (43 – 55),
five of them isolated as 6,8-diglycosyl derivatives (51 – 55); 14 flavonols (56 – 69), nine
of them as their methyl ether (61 – 69); 13 flavanones (70 – 74 and 77 – 84), eight of them
Fig. 2. Flavonoid and sesquiterpene distribution in Flourensia species

as 8-prenyl substituted (77 – 84); five flavanonols (75, 76, and 85 – 87), with 85 – 87 being
8-prenylflavanonols; one 8-prenylflavone (88), one favanol (89), and a chalcone (90).
The 8-prenylated flavonoids (77 – 88) appear to be restricted to the South American
species F. campestris, F. fiebrigii, F. heterolepis, F. macrophylla, and F. riparia.
Flavanones (70 – 74) and flavanonols (75 and 76) are common to both North and
South American species, while flavones and flavonols (43 – 69) appear to be more
frequently isolated in the North American species F. resinosa, F. cernua, and F. retino-
phylla. The 6,8-diglycosyl flavonols 51 – 55 have been isolated only from F. cernua. The
oxidation pattern most frequently reported for these compounds appears at C(5), C(7) ,
and C(4’) (characteristic of apigenin derivatives 45 – 48 and 51 – 55), although C(3),
C(5), and C(7) (galangin derivatives 56, 57, and 61), C(3), C(5), C(7), C(3’), and C(4’)
(quercetin derivatives 59, 60, 63, and 64) and C(3), C(5), C(7), and C(4’) (kaempferol
derivatives 65 and 67) are also frequently oxidized. Approximately 39% of the
flavonoids identified in these species contain an O-atom at C(3). The North American
species of Flourensia seem to have its biosynthetic machinery preferentially directed
toward flavonoid synthesis (Fig. 2).
2.3. Benzofurans, Chromenes, and Coumarins. The benzofurans, chromenes, and
coumarins constitute the third most numerous group of metabolites isolated from
Flourensia. This group includes 20 benzofurans (91 – 110), eight chromenes (111 – 118),
and five coumarins (119 – 123). The presence of a 5-Ac group is common to nearly all
benzofurans isolated from Flourensia (91 – 107). A 2-isopropenyl group (91 – 101 and
106 – 110) or a 2-Ac group (104 and 105) is also a common feature in these compounds.
Chromenes from Flourensia also include the characteristic 6-Ac group and a similar
oxidation pattern to that observed in the benzofurans. Coumarins isolated from this
genus have been identified exclusively in South American species, with three of them
existing as prenyletin-6-methyl ether derivatives (119 – 121). Finally, F. riparia is the
only species of Flourensia that includes a chlorinated benzofuran (103) [63].
2.4. Miscellaneous Compounds. Acetophenones (124 – 129), propenoic acid deriv-
atives (130 – 132), methyl orsellinate (133), ellagic and cinnamic acids (134 and 135,
resp.), and methyl gallate (136) are aromatic compounds that have also been isolated
from the plants of Flourensia. Additionally, a few lupane triterpenes (137 – 144), d-
lactones (145 – 151), and the characteristic acetylene compounds from the Asteraeae
family (152 – 156), and some miscellaneous metabolites (157 – 160) have been
characterized as well.
2.5. Essential Oils. The strong odor emitted from the aerial parts of the Flourensia
species is indicative that they are rich in essential oils. Nevertheless, only F. oolepis, F.
thurifera, F. campestris, and F. cernua essential oils have been chemically analyzed. Gas
chromatography coupled to mass spectrometry (GC/MS), headspace (HS) and
headspace solid-phase microextraction (HS-SPME) GC/MS are frequently used
techniques to establish their complex composition. The chemical composition of the
essential oils depends on several factors, such as plant age, the growth stage, the
collection period of the plant material, biotic and abiotic factors, stress and the
phenology of each species [9] [51]. For Flourensia species, a total of 175 volatile
compounds have been characterized, distributed throughout 13 categories: four acyclic
carbonyl and aromatic compounds (161 – 164), twelve acyclic monoterpenes (165 –
176), one acyclic sesquiterpene (177), two acyclic diterpenes (178 and 179), one acyclic
triterpene (180), 25 monocyclic monoterpenes (181 – 206), 23 bi- and tricyclic
monoterpenes (207 – 229), 15 monocyclic sesquiterpenes (37 and 230 – 243), 53 bicyclic
sesquiterpenes (1, 26, and 244 – 294), 22 tricyclic sesquiterpenes (42 and 295 – 315), two
polycyclic sesquiterpenes (316 and 317), five miscellaneous compounds (318 – 322),
and ten hydrocarbons (323 – 332).
As seen in Table 2, mono- and sesquiterpenes are the most common components
found in Flourensia essential oils. The following 23 compounds were the most
consistently identified and are named in decreasing order of frequency in which they
have been found in the essential oils: limonene (186), b-pinene (214), a-copaene (310),
a-pinene (213), b-caryophyllene (250), caryophyllene oxide (251), a-thujene (208), d-
3-carene (212), camphene (223), 1,8-cineole (228), a-caryophyllene (238), d-cadinene
(267), b-selinene (277), b-eudesmol (28), spathulenol (42), sabinene (207), borneol
(226), germacrene D (235), g-muurolene (261), g-cadinene (266), aromadendrene
(292), alloaromadendrene (296), and a-cubebene (306).
The variations in four monoterpenes and 19 sesquiterpenes in the essential oil of dry
aerial parts from F. campestris were analyzed in the spring and summer seasons. Mono-
terpenes were consistently the minor compounds, being present at 0.7% during the spring
and at 13.1% during the summer. Sesquiterpenes were the predominant compounds and
represented 96.0 and 79.9% in the spring and summer, respectively. The principal
components from this essential oil during the spring included bicyclogermacrene (252;
36.7%), globulol (302; 19.6%), b-caryophyllene (250; 15.3%), and bicycloelemene (254;
10.2%); while spathulenol (42; 32.2%), caryophyllene oxide (251; 13.4%), 250 (6.0%),
and bicyclogermacrene (252; 5.6%) represented the major compounds identified during
the summer [9]. Sixty-five mono- and sesquiterpenes were identified as components in
F. oolepis essential oil, with g-gurjunene (291; 20.69%), d-cadinene (267; 10.27%), 4-eth-
enyl-4,8,8-trimethyl-2-methylidenebicyclo[5.2.0]nonane (249; 10.15%), santolinetriene
(165; 6.22%), and t-muurolene (262; 6.14%) present as the major chemical components
[15]. Volatile compounds from a CH2Cl2 extract of fresh flower heads from F. thurifera
were analyzed, and 36 compounds corresponding to 82% of the total composition of this
extract were identified. Similar to the F. oolepis essential oil, mono- and sesquiterpenes
were the principal components of the volatile fraction, although phytol, isophytol, and a
hydrocarbon fraction of n-alkanes from C23 to C31 and C33 were also identified.
Additionally, a-ocimene (170; 10.1%), a-cubebene (306; 19.1%), b-caryophyllene
(250; 7.4%), and germacrene B (234; 3.4%) were its major components [8].
A total of 129 volatile compounds were identified in five analyses performed on F.

cernua leaf essential oils collected from the south central New Mexico area
[17] [20] [33] [35] [36]. The F. cernua essential oil is consistently composed of b-
eudesmol (28), b-myrcene (174), cis-jasmone (181), limonene (186), p-cymene (202),
d-3-carene (212), a-pinene (213), camphene (223), borneol (226), 1,8-cineole (228),
250, caryophyllene oxide (251), g-eudesmol (278), a-eudesmol (280), globulol (302),
and flourensadiol (41). All five of these studies were developed to support the
hypothesis that the chemical composition of the leaf surface is related to its defoliation
and livestock herbivory, and the presence of 181, 202, p-cymen-8-ol (204), sabinene
(207), thuja-2,4(10)-diene (209), isoborneol (225), 250, a-muurolene (258), d-cadinene
(267), 302, and a-copaene (310) were related to these phenomena [20] [36].
Nine chemical classes are considered descriptive of the Heliantheae tribe and the
Asteraceae family: polyacetylenes, monoterpenes, sesquiterpenes, sesquiterpene
lactones, diterpenes, triterpenes, coumarins, benzofurans, and flavonoids [66]. With
the exception of polyacetylenes and diterpenes, the remaining seven classes of
compounds have been isolated from plants of Flourensia, with the addition of
benzopyrans, a chemical class very common for this genus. In light of the chemical
compositions of Flourensia species, the eudesmane sesquiterpenes (including eudes-
mane sesquiterpene lactones), flavonoids, benzofurans, benzopyran, and coumarin
pattern can be used as a footprint to characterize this genus as chemical bookmarks and
as valuable tools with regard to chemosystematic approaches for this genus.
3. Ecological Aspects. – 3.1. Flourensia campestris Griseb. (common name chilca).

F. campestris is a native species of Argentina, and it grows as a dominant plant in highly
dense colonies and frequently forms nearly pure populations [9]. A solution (2 ml) of a
10 mg/ml EtOH extract from the aerial parts of this plant was tested for herbicidal
activity, which was measured as the germination inhibitory effect (IG%) on Avena
sativa and Raphanus sativus. The IG values showed moderate activity at 5.8 and 11.63%
for A. sativa and R. sativus, respectively [25]. Aqueous extracts from the dry aerial parts
of this plant exhibited strong inhibitory effects on germination (ECg50 3.9%), root
growth (ECr50 1.5%), and shoot growth (ECs50 2.0%) in Lactuca sativa. The bio-guided
chemical analysis of this extract led to the identification of the phytotoxic,
allelochemical, and herbicidal compound, (¢)-hamanasic acid A (39), an inhibitory
active compound with regard to germination (ECg50 2.9 mm), root growth (ECr50
1.5 mm), and shoot growth (ECs50 2.0 mm) [9]. Currently, 39 is the only sesquiterpene
that has been isolated from this plant (Table 2). It is considered that both the aqueous
and EtOH extracts contain 39. The herbicidal and phytotoxic activities are likely due to
the presence of compound 39 in both cases. However, a MeOH extract from the aerial
parts of F. campestris exhibited 100% inhibition of the monophenolase activity of
mushroom tyrosinase with an IC50 107.91 mg/ml. This enzyme catalyzes the oxidation of
phenolic compounds to quinones, the phenomenon responsible for the darkening of
several foods and plant products [26]. The flavonoids, (2S)-3’,4’,7-trihydroxy-8-(4-
hydroxy-3-methylbut-2-en-1-yl)flavanone (81), exiguaflavanone K (84), and 8-pre-
nyldihydroisorhamnetin (86), as well as the benzofuran 6-methyleuparone (105) have
also been characterized from this extract [24]. These aromatic compounds have
reputations as antioxidant agents, perhaps also acting on mushroom tyrosinase. These
results show that the polar extracts of F. campestris have potential application for the
use as natural herbicides and preservatives in food products.
3.2. Flourensia cernua DC. (common names blackbrush, tarbush, varnish bush,
hojas¦n, hojas¦, ojasen, and hoja ancha). F. cernua is a dominant shrub endemic to the
southwestern United States (Texas, New Mexico, and Arizona), northern and central
M¦xico (Chihuahua, Coahuila, Nuevo Leýn, Durango, Zacatecas, San Luis Potos,
Guanajuato, and Hidalgo), Argentina, and Chile [6] [21]. It has contributed to the
desertification of these regions, to the transition from grasslands to shrublands and to
the deterioration of the Chihuahua desert [20]. This species can be found as both a
high- and a low-population density variety in this region; however, the two varieties do
not exhibit genetic differences [67]. It is possible that the success of this plant with
regard to the domination of the ecosystem in which it lives is due to several factors or to
a combination of all of them, for example, i) F. cernua possesses extensive root systems
that allow the efficient harvest of water and nutrients compared to the grasses
associated with these species [37]; ii) this plant also has a resinous leaf surface that
constitutes a mechanic barrier to dehydration; iii) the resin includes abundant phenolic
compounds and condensed tannins that provide a chemical barrier to prevent insect
and herbivore attacks [37]; iv) chemical components of the resin are transported to the
soil surface during precipitation events [39], which likely inhibits the growth of other
plants; and v) F. cernua secondary metabolites have a direct relationship with diet
selection to establish the type of plant-herbivore interactions [33].
Chemical profiles of the leaf surface have been associated with the degree of
herbivory. The contained compounds are important for defense because they affect the
selection pattern or because they are toxic to certain species of herbivores [36]. For
example, F. cernua flowers, in large amounts, are toxic to livestock [68], and the
abundances of the total phenolics and terpenes (mono- and sesquiterpenes) in this
plant are responsible for its low appeal by livestock [34] [36]. Additionally, the removal
of secondary metabolites from its leaf surface by immersing in acetone or EtOH
increased consumption by lambs, suggesting that the presence of these compounds
reduced its desirability to sheep [14]. The chronic ingestion of F. cernua leaves causes
toxicosis in lambs, which is manifested by apoptotic liver damage, elevated blood serum
levels of g-glutamyl transpeptidase, aspartate aminotransferase, sodium and potassium,
and a markedly elevated lactate dehydrogenase activity [19]. However, an acute
toxicity test using Wistar rats at the maximum recommended concentration (a single
dose of 2000 mg/kg body weight of a 60% EtOH extract) showed only slight signs of
toxicity 30 min after administration in the test group, with no animal deaths and no
pathological changes in organs after 14 days [46]. The petrol-soluble portion of the
crude extract of this plant showed moderate toxicity against goldfish [29] in addition to
antifungal, insecticide, and antitermite activities [18].
A CH2Cl2/MeOH (1 : 1) extract of F. cernua showed phytogrowth inhibitory activity
against Amaranthus hypochondriacus (IC50 300 mg/ml). A bioassay-directed fractio-
nation of this extract led to the isolation of three inhibitors of the radical growth of A.
hypochondriacus and Echinochloa crus-galli, dehydroflourensic acid (18), flourensa-
diol (41), and methyl orsellinate (133). These phytotoxins interacted in vitro with the
regulatory protein calmodulin, which influences a number of important plant growth
events [21].
Hexane, Et2O, and EtOH extracts of F. cernua leaves showed a markedly different
profile of the volatile chemical composition. The hexane extract consisted almost
entirely of monoterpenes, the Et2O extract contained monoterpenes and sesquiter-
penes, and the EtOH extract consisted almost exclusively of sesquiterpenes. Despite
the different chemical compositions, all three crude fractions were active against the
fungi Colletotrichum gloeosporioides, C. fragaria, and C. accutatum, and all three also
showed high degrees of termiticidal activity. The complete inhibition of the
cyanobacteria Oscillatoria perornata was observed for the hexane and Et2O extracts,
while the complete inhibition of O. agardhii occurred only with the hexane extract.
Finally, the complete inhibition of the green algae S. capricornutum was established
only for the hexane extract [17]. Lanolin and cocoa butter extracts of F. cernua leaves
exhibited 76.2 and 100%, respectively, mycelia inhibition in Rhizoctonia solani, one of
the causal disease agents associated with roots and tubers of various crops. Both organic
solvents ensured the extraction of high concentrations of hydrolyzable and condensed
tannins from this plant, resulting in a direct correlation between the tannin
concentration and activity [45]. H2O, EtOH, cacao butter, and lanolin extracts from
this same plant were also assayed for their antibacterial activity [49]. It is possible that
these extracts include other types of compounds that contribute to the high
antimicrobial potential of this plant, making F. cenua an attractive alternative for use
against plant pathogenic microorganisms.
F. cernua is also a source of quercetin (59), catechin (89), ellagic acid (134),
cinnamic acid (135), and methyl gallate (136) [43] [48], and it produces a mild
antioxidant activity, which is attributed to its total phenolics content [42]. Solid-state
fermentation from aqueous phenolic extracts of its leaves with Aspergillus niger spores
causes the biodegradation of hydrolyzable and condensed tannins to produce the
antioxidant compound, gallic and ellagic acids [22] [44]. This fermentation process
enhances both the antioxidant activity of this extract, which is measured as its ability to
capture DPPH (1,1-diphenyl-2-picrylhydrazyl) free radical, and its antifungal activity,
measured by the growth inhibition of Fusarium oxysporum and Penicillium expansum
[50].
3.3. Flourensia oolepis S. F. Blake (common names chilca, chilca melosa, and chilca
gomosa). An EtOH extract of F. oolepis at 200 mg/cm2 exhibited 98.8% antifeedant
activity in Epilachna paenulata larvae, 100% germination inhibition of both Avena
sativa and Raphanus sativum seeds at a concentration of 10 mg/ml, and bactericidal
activities against Escherichia coli with a MIC value of 2 mg/ml. The partition of this
extract between aqueous MeOH and hexane (1 : 9) produced aqueous MeOH and
hexane extracts with nearly identical activity values as these three assays [58]. F. oolepis
essential oil possesses a dose-dependent repellent effect with moderate dose-depend-
ent toxic effects in the adult stage of Coleoptera Tribolium castaneum. Insects exposed
to doses between 0.190 and 0.750 mg/cm2 of its oil suffered tremors, convulsions, and a
lack of mechanical coordination, indicating neurotoxic action. This oil also produces an
83% feeding reduction in Coleoptera Leptinotarsa decemlineata adults at a dose of
100 mg/cm2 and affected the settling behavior of the Homeoptera polyphagous aphide
Myzus persicae, while Rhopalosiphum padi did not respond to this oil [15]. However,
an EtOH extract of the aerial parts of this plant showed strong antifeedant activity
against Epilachna paenulata, Xanthogaleruca luteola, and Spodoptera frugiperda, with
the AI values of 99.1, 98.0, and 92.0%, respectively, at 100 mg/cm2. Using a bio-guided
analysis, pinocembrine (72) was identified as the most active compound from this
extract, with the ED50 values of 7.98, 6.13, and 8.86 mg/cm2, against E. paenulata, X.
luteola, and S. frugiperda, respectively [13]. A separate EtOH extract inhibited R.
sativum and Panicum miliaceum germination, with the GI values of 99.1 and 100% at
10 mg/ml, respectively. A bio-guided assay isolated ilicol (25) and 72 as the most active
compounds from this extract. Both compounds exhibited phytotoxic properties,
inhibiting the germination of P. miliaceum, A. sativa, R. sativum, and Letuca sativa, with
72 being the most active compound. Although less effectively, both 28 and 72 inhibited
the root growth of the four species and also reduced Allium cepa cell division. All these
results suggested that the EtOH extract of F. oolepis and especially compounds 25 and
72 possess significant potential for use as natural herbicides [12].
3.4. Flourensia thurifera DC. (common names flor del incienso, incienso, maravilla,
maravilla del campo, and maravilla del cerro). This plant is a native shrub from the
semiarid environments of central Chile, where it occasionally forms large and nearly
monospecific communities [7] [8]. A CH2Cl2 extract from this plant was shown to
display antifeedant activity against Spodoptera littoralis larvae. This activity may have
been attributed to the high content of the chromene encecalin (111) [7], but it could
also have been due to the presence of 3b-hydroxycostic acid (2), a sesquiterpene with
moderate antifeedant activity against this same moth [64]. A MeOH extract of this
plant consisted of coumarins and chromenes and showed high toxicity towards Artemia
salina due to the presence of 111, demethylencecalin (112), prenyletin (119), and
prenyletin 6-methyl ether (120). These compounds play an important role in the
chemical defense of this species [7].
3.5. F. microphylla S. F. Blake (no common names found), F. cernua (vide supra),
and F. retinophylla S. F. Blake (yerba de la mula). The antifungal activities of
EtOH crude extracts from F. microphylla, F. cernua, and F. retinophylla were assayed at
0, 10, 100, 500, 1000, and 1500 ml/l concentrations for mycelium development in the
pathogens Alternaria sp., Rhizoctonia solani, and Fusarium oxysporum. An inhibitory
effect was observed as low as 10 ml/l in all three Flourensia species. At 100 ml/l, an
inhibition of 49 – 77% and 70 – 88% was observed for all three species in Alternaria sp.
and R. solani, respectively, while an inhibition of 65 – 80% was observed in F.
oxysporum for F. microphylla and F. retinophylla. Finally, the nearly complete
inhibition of all three fungi was observed for all three Flourensia species at the 1000 ml/l
concentration [41].
3.6. F. riparia Griseb. (no common names found), F. fiebrigii S. F. Blake (no
common names found), and F. tortuosa Griseb. (no common names found). The
antimicrobial activities of extracts and some pure compounds from F. riparia, F.
fiebrigii, and F. tortuosa were assayed against four strains of the Gram-positive
bacterium Paenibacillus larvae (P. larvae 35A, P. larvae Azul, P. larvae I, and P. larvae
III), the most widespread and destructive brood diseases of the Apis mellifera (honey
bee). CHCl3 and Et2O extracts of F. riparia showed a MIC value of 250 ppm in both
P. larvae Azul and P. larvae I. Eight pure compounds from the CHCl3 extract of this
plant were assayed, but only exiguaflavanone K (84) and 8-prenyldihydroisorhamnetin
(86) were moderately active against P. larvae Azul and P. larvae 35A, showing
the MIC values of 625 and 500 ppm, respectively. Additionally, an Et2O extract from
F. fiebrigii exhibited a moderate effect in these bacterial strains. (2S)-3’,4’,7-trihydroxy-

8-(3-methylbut-2-en-1-yl)flavanone (79) was the most active pure compound from this
extract, with an MIC value of 500 ppm against the two P. larvae strains, and 8-
prenyleriodictiol (80) exerted a considerable effect in P. larvae Azul (MIC 500 ppm)
and a moderate effect in P. larvae 35A (MIC 1000 ppm). The toxicity of the Et2O
extracts of both F. riparia and F. fiebrigii on A. mellifera was also evaluated, and no bee
mortality was observed after 72 h of treatment, even at the highest extract concen-
trations [53].
4. Ethnopharmacology. – F. cernua DC is the most chemically analyzed species of

this genus, and it is the only species used in folkloric medicine in M¦xico and the United
States [19]. An infusion of leaves, flowers, and flower heads of this plant is used in
traditional medicine as a remedy for indigestion, stomachaches, diarrhea, dysentery,
and other digestive disorders [21] [22] [35], and activities associated with these diseases
have been probed. F. cernua has also been used as an expectorant, for respiratory
infections and tuberculosis [40] [47]. An aqueous decoction and hexane, acetone, and
MeOH extracts from its leaves were assayed against two Mycobacterium tuberculosis
strains, one was resistant (H37Rv) and the other one was sensitive to the antituber-
culosis drugs, streptomycin, isoniazide, rifampin, ethambutol, and pyrazinamide
(CIBIN/UMF:15 : 99). The hexane extract was the most active against both strains,
exhibiting the MIC values of 50 and 25 mg/ml for the resistant and sensitive strain,
respectively, while the acetone extract was moderately active, with the MIC values of
200 and 100 mg/ml, respectively. However, the MeOH extract was only active against
the resistant strain (MIC 200 mg/ml), while the aqueous extract was not active against
both strains [40] [47]. Finally, a CHCl3/MeOH (1 : 1) extract of this plant possessed
antibiotic activity against the Gram-positive bacteria Bacillus cereus and Staph-
ylococcus aureus, against the Gram-negative bacteria Pseudomonas aeruginosa and
Escherichia coli and against the yeast Saccharomyces cereviseae and Candida albicans.
Interestingly, a MeOH sub-extract was exhibited cytotoxic activities against the human
breast cancer cellular lines BT20, SKBR3, MDA-MB231, MDA-MB453, and MDA-
MB468. Column chromatography (Sephadex LH-20, MeOH) of this extract yielded
eight fractions, Frs. 1 – 8, of which Frs. 2 and 4 exhibited the most cytotoxicities, with an
MIC value of 0.007 mg/ml against both BT20 and SKBR3 for Fr. 2, and an MIC value of
0.007 mg/ml against MDA-MB453 for Fr. 4 [38].
5. Conclusions. – Plants of the genus Flourensia are located in semidesertic, desertic,

dry, and arid environments. Nevertheless, they have successfully colonized these
regions, and they favorably compete with other typical species native to these
ecosystems. It is common to find plants belonging to the genus Flourensia forming large
colonies of a single species. These plants gradually displace native vegetation, altering
the conformation and development of these ecosystems. Several theories have tried to
explain this phenomenon. It is believed that the success of these plants is due to the
combination of several factors that favor their adaptation and development in these
environments. The anatomical, morphological, and architectural characteristics of
these plants are important factors that promote water absorption. An abundant waxy
coating on their aerial parts promotes water retention, acting as protective barrier
to intense solar radiation. These plants possess a sophisticated synthetic machinery,

producing a complex exogenous and endogenous mixture of chemicals. A great variety
and quantity of exogenous secondary metabolites are present within the waxy coating.
It is believed that the wealth of its chemical composition is an arsenal that these plants
use to combat fungi, bacteria, viruses, insects, herbivores, and even other plants that it
competes within its ecosystem. From this point of view, Flourensia species are very
important because their extracts and pure compounds can be excellent natural agents
for pest control. The chemical characterizations of the extracts could lead to the
discovery of new allelopathic, antifeedant, insecticidal, antibacterial, antifungal, and
antiviral pure compounds. Extracts and pure compounds of Flourensia can be used to
improbe the quantity and quality of agricultural products, one of the major constraints
of farm production. They also can be used as new alternatives to preserve vegetables,
fruits, and grains that are stored for long periods of time and that could be affected by
microorganisms (bacteria, fungi, and viruses). Several studies on plants of this genus
have proven its effectiveness in this regard: the discovery of phytotoxic, allelochemical,
and herbicidal properties of (¢)-hamanasic acid A, dehydroflourensic acid, flourensa-
diol, methyl orsellinate, pinocembrine, and ilicol, which have been isolated from
various species of Flourensia; the potential application of the MeOH extract of F.
campestris as a natural herbicide and food preserver; the chemical profile of the leaf
surface of F. cernua, which was associated with its poor selection and low consumption
by herbivores; the antifungal, insecticide, and antitermite activities of the nonpolar
extract from F. cernua; the antifeedant activity of pinocembrine isolated from F. oolepis
and of encecalin and 3b-hydroxycostic acid isolated from F. thurifera; the antimicrobial
activity of exiguaflavanone K and 8-prenyldihydroisorhamnetin isolated from F. riparia
and of (2S)-3’,4’,7-trihydroxy-8-(3-methylbut-2-en-1-yl)flavanone and 8-prenyleriodic-
tiol from F. fiebrigii; and finally, the insecticidal activity of the essential oils of several
Flourensia species. All these biological activities are specific examples of the important
ecological roles played by these plants. In accordance with this chemical and biological
review, Flourensia species contain essential oils, extracts, and pure compounds that
exhibit considerable potential for the use as a part of an integrated pest management
strategy of commercial crops.
Costic acid, alantolactone, and bisabolane sesquiterpene derivatives, as well as 8-
prenylated flavanones and flavanonols appear to characterize the South American
species of Flourensia, while flourensic acid derivatives, cryptomeridiol, flourensiadiol,
spathulenol, flavones, and flavonols are major compounds isolated from North
American species.
I am grateful to Biol. Enrique Salazar Leyva for his technical assistance. This research was financially
supported by CONACyT (Grant No. 241044).
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Received June 12, 2014

Chemistry Biodiversity - 2015 - Rios - Chemistry and Biology of The Genus Flourensia Asteraceae

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Chemistry Biodiversity - 2015 - Rios - Chemistry and Biology of The Genus Flourensia Asteraceae

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CHEMISTRY & BIODIVERSITY – Vol.

Chemistry and Biology of the Genus Flourensia (Asteraceae)

Õ 2015 Verlag Helvetica Chimica Acta AG, Zîrich

1. Introduction. – Asteraceae is one of the largest families in the order Asterales

Fig. 1. Anatomical aspects of Flourensia plants

countries for various purposes, such as in the alleviation of gastrointestinal ailments,

2. Chemical Composition of Flourensia Species. – To date, 13 species of Flourensia

Table 1. Chemically and Biologically Analyzed Species of the Genus Flourensia

Species Origin Plant material Extract Analysis Biological activity Ref.

Texas, USA Flowering heads EtOH Chemical composition – [28]

Species Origin Plant material Extract Analysis Biological activity Ref.

production dation of tannins

Species Origin Plant material Extract Analysis Biological activity Ref.

Species Origin Plant material Extract Analysis Biological activity Ref.

No. InChI Key Name Source Ref.

23 NSWYDQDLHIJCPK-TYNCELHUSA-N 1-Oxocostic acid F. heterolepis [54]

No. InChI Key Name Source Ref.

52 OVMFOVNOXASTPA-MCIQUCDDSA-N 8-C-b-d-Glucosyl-6-C-b-d-xylosylapigenin F. cernua [31]

No. InChI Key Name Source Ref.

No. InChI Key Name Source Ref.

95 LQUPQVIPBLTZNW-HZIYNJIRSA-N (2Z )-1-[(2R,3S )-5-Acetyl-2,3-dihydro-2-(1-methyl- F. fiebrigii [52]

No. InChI Key Name Source Ref.

2H-1-benzopyran-6-yl]ethanone (deoxodehydro- F. macrophylla

No. InChI Key Name Source Ref.

127 QJAPFSSVKIZTMR-UHFFFAOYSA-N 1-[3-(3-Methylbut-2-en-1-yl)phenyl]ethanone F. cernua [32]

No. InChI Key Name Source Ref.

148 RATVVPKFLMJAST-AREMUKBSSA-N Heptacosan-4-olide F. cernua [21]

No. InChI Key Name Source Ref.

167 WPPVSYVQAKQNJK-VIFPVBQESA-N Artemisia alcohol F. cernua [17] [20] [35]

No. InChI Key Name Source Ref.

195 IZXYHAXVIZHGJV-NXEZZACHSA-N cis-p-Menth-2-en-1-ol F. cernua [20]

No. InChI Key Name Source Ref.

219 UASZOTVHPVEMQR-AXFHLTTASA-N cis-Chrysanthenyl acetate F. cernua [20]

No. InChI Key Name Source Ref.

243 GFJIQNADMLPFOW-VNHYZAJKSA-N Elemol F. cernua [20] [35]

No. InChI Key Name Source Ref.

267 FUCYIEXQVQJBKY-ZFWWWQNUSA-N d-Cadinene F. campestris, [9] [15] [17] [20]

No. InChI Key Name Source Ref.

294 FWKQNCXZGNBPFD-UHFFFAOYSA-N Guajazulene F. oolepis [15]

No. InChI Key Name Source Ref.

318 NNBZCPXTIHJBJL-MGCOHNPYSA-N trans-Decahydronaphthalene F. cernua [20]

No. InChI Key Name Source Ref.

Fig. 2. Flavonoid and sesquiterpene distribution in Flourensia species

A total of 129 volatile compounds were identified in five analyses performed on F.

3. Ecological Aspects. – 3.1. Flourensia campestris Griseb. (common name chilca).

F. fiebrigii exhibited a moderate effect in these bacterial strains. (2S)-3’,4’,7-trihydroxy-

4. Ethnopharmacology. – F. cernua DC is the most chemically analyzed species of

5. Conclusions. – Plants of the genus Flourensia are located in semidesertic, desertic,

to intense solar radiation. These plants possess a sophisticated synthetic machinery,

[4] M. V. Correia, H. H. Fokoue, M. J. P. Ferreira, L. Scotti, M. T. Scotti, S. A. V. Alvarenga, G. V.

[40] G. M. Molina-Salinas, M. C. Ramos-Guerra, J. Vargas-Villarreal, B. D. Mata-Crdenas, P. Becerril-

Received June 12, 2014

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[40] G. M. Molina-Salinas, M. C. Ramos-Guerra, J. Vargas-Villarreal, B. D. Mata-Crdenas, P. Becerril-