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The genus Machaerium (Fabaceae):

taxonomy, phytochemistry, traditional
uses and biological activities
a a a
Yhiya M. Amen , Amani M. Marzouk , Mona G. Zaghloul &
a
Mohamed S. Afifi
a
Pharmacognosy Department, Faculty of Pharmacy, Mansoura
University, Mansoura35516, Egypt
Published online: 20 Jan 2015.
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To cite this article: Yhiya M. Amen, Amani M. Marzouk, Mona G. Zaghloul & Mohamed S.
Afifi (2015): The genus Machaerium (Fabaceae): taxonomy, phytochemistry, traditional uses
and biological activities, Natural Product Research: Formerly Natural Product Letters, DOI:
10.1080/14786419.2014.1003062
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Natural Product Research, 2015
http://dx.doi.org/10.1080/14786419.2014.1003062
REVIEW
The genus Machaerium (Fabaceae): taxonomy, phytochemistry, traditional
uses and biological activities
Yhiya M. Amen*, Amani M. Marzouk, Mona G. Zaghloul and Mohamed S. Afifi
Pharmacognosy Department, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt

(Received 26 September 2014; final version received 21 December 2014)
HO
O
H
H
COOH
N
Machaerium
H
CH3
Taxonomy Historical consideration Phytochemistry Traditional uses Biological activities
OCH3
OH OCH3
OCH3 H3CO OH O
H3CO
HO O O
HO HO
O OH O
H HO HO
O
OH
O OCH3 O
H
Machaerium, in the family Fabaceae, predominantly is a genus of a Neotropical

distribution of trees, shrubs, and lianas occurring from southern Mexico to Brazil and
northern Argentina and as far as South America. Several Machaerium species are
widely used in traditional medicine and are considered to have multiple medicinal
properties. This review aims to provide up-to-date and comprehensive information on
the taxonomy, phytochemistry, traditional uses and biological activities of plants in the
genus Machaerium.
Keywords: Machaerium; Fabaceae; phytochemistry; uses; biological activities
1. Introduction
Family Leguminosae (Fabaceae) is the third largest family of flowering plants, exceeded by
Compositae (Asteraceae) and Orchidaceae (Harborne et al. 1971). It is commonly known as the
legume, pea or bean family. The name Fabaceae comes from genus Faba, now included into
Vicia. Leguminosae is the older name of this family that refers to the typical fruit, which is called
legume. The family includes 727 genera with nearly 19,325 species (Lewis et al. 2005).
Fabaceae has traditionally been divided into three subfamilies: Mimosoideae, Caesalpinioideae
and Papilionoideae.
These plants are indigenous to all climatic places ranging from equatorial rainforests to the
verges of dry and cold deserts (Polhill et al. 1981). Subfamily Papilionoideae is the largest group
of legumes, consisting of about 478 genera and 13,800 species in 28 tribes (Lewis et al. 2005;
Veitch 2007). The name of the group probably originated because of the flower’s resemblance to
a butterfly (Latin: papilio). One acceptable alternative name for this subfamily is Faboideae
*Corresponding author. Email: yhiyaamen@gmail.com
q 2015 Taylor & Francis

2 Y. M. Amen et al.
(Harborne et al. 1971). The subfamily has a worldwide distribution but with most of the woody
representatives (trees and climbers) in the tropics and the southern hemisphere and the
herbaceous and shrubby members in temperate zones, with a special concentration in the
Mediterranean region (Harborne et al. 1971).
2. Taxonomy
Machaerium is a well-established genus belonging to Dalbergieae, a tribe in Papilionoideae,
mostly accepted to consist of 19 genera and about 300 species by Polhill et al. (1981). However,
recent molecular phylogenetic studies (Lavin et al. 2001) have led to a re-circumscribed
Dalbergieae, and the tribe comprises 49 genera and ca. 1200 species (Klitgaard & Lavin 2005).
Machaerium is the third largest Dalbergioid genus with approximately 130 species (Cardoso
et al. 2013; Filardi & de Lima 2014) while the Plant List (www.theplantlist.org, accessed 26
September 2014) includes 262 scientific plant names of species rank for the genus Machaerium;
of these, 155 are accepted species names. Machaerium is a genus of scandent to upright shrubs or
lianas and small to medium sized, rarely large trees occurring from sea level to 500 –900 m. The
genus is known from southern Mexico to Brazil and northern Argentina and as far as South
America. M. isadelphum is distributed to Trinidad and Tobago, and another species (M.
lunatum) to the west coast of Africa (Bernardi 1984; Klitgaard & Lavin 2005; Lozano &
Klitgaard 2006). The name Machaerium probably has its own origin in a word that means
‘machete’ in Greek, which means in English, a large cleaver-like cutting tool, referring to its
fruit shape (referenced in Lozano & Klitgaard 2006). Machaerium is diagnosed in part by the
unique morphology of its samara fruits, which includes a basally positioned indehiscent seed
chamber that bears (and is often seemingly jointed to) a terminally positioned wing (Lima 1990).
3. Historical consideration
Persoon (1807) introduced the genus Machaerium Pers. as a section of Nissolia Jacq.
He established the genus after separating three species from Nissolia Jacq.; M. ferrugineum
(Willd.) Pers., M. punctatum (Poir.) Pers., and M. reticulatum (Poir.) Pers. He retained two
species in Nissolia; N. fructicosa Jacq. and N. arborea Jacq., which were later transferred to
Machaerium by Vogel (Rudd 1987). The most comprehensive treatments of Machaerium have
been by Bentham (1860); all the species known to date were assessed. After reducing some
names to synonymy and transferring some to other genera, a total of 56 species remained. Using
leaflet shape, venation and stipule texture, he divided the genus into five series (Lineata,
Oblonga, Acutifolia, Reticulata and Penninervia) and included them in the tribe Dalbergieae
(Bentham 1860; Lozano & Klitgaard 2006). Taubert (1894) later raised Bentham’s series to the
sectional rank. Hoehne (1941) published a more complete revision of Machaerium, with a total
of 121 species (Lozano & Klitgaard 2006).
4. Phytochemistry
Genus Machaerium is reported to contain flavonoids, alkaloids, triterpenoids, steroids, fatty acid
derivatives, cimmamylphenols and other miscellaneous compounds. Of the 262 species known,
only few species were phytochemically studied. The details of the isolated compounds are
summarised as follows and listed in Table 1.
4.1. Flavonoids and related compounds

Isoflavonoids are phytochemically highly characteristic of the Fabaceae and with limited
distribution in non-leguminous plant families. They are found predominantly in subfamily
Natural Product Research 3
Table 1. Compounds isolated from the genus Machaerium.

No. Compounds Species References
Flavonoids and related compounds
Isoflavones
1 Formononetin M. kuhlmannii Hoehne Ollis, Redman, Roberts et al. (1978)
M. nictitans (Vell.) Benth. Ollis, Redman, Roberts et al. (1978)
M. vestitum Vog. Kurosawa, Ollis, Redman, Sutherland,
and Gottlieb (1978)
M. aristulatum (Spruce ex El-Sohly et al. (1999) and Seo et al.
Benth.) Ducke (2001)
2 Isoformononetin M. villosum Vog. Kurosawa et al. (1978b)
3 Calycosin M. villosum Vog. Kurosawa et al. (1978b)
M. mucronulatum (Mart.)
Benth.
M. aristulatum (Spruce ex El-Sohly et al. (1999)
Benth.) Ducke
4 Daidzein M. villosum Vog. Kurosawa et al. (1978b)
5 30 -Hydroxydaidzein M. villosum Vog. Kurosawa et al. (1978b)
Isoflavans
6 Machaerol B M. pedicellatum Vog. Ogiyama and Yasue (1973)
7 Machaerol C M. pedicellatum Vog. Ogiyama and Yasue (1973)
8 ( – ) Mucronulatol M acutifolium Vog. Kurosawa, Ollis, Redman, Sutherland,
Alves et al. (1978)
Alves et al. (1978)
M. mucronulatum (Mart.) Kurosawa et al. (1978b)
Benth
M. villousm Vog.
M. opacum Vog. Ollis, Sutherland et al. (1978)
9 (^ ) Mucronulatol M. mucronulatum (Mart.) Kurosawa et al. (1978b)
Benth
10 (þ ) Vestitol M. vestitum Vog. Kurosawa, Ollis, Redman, Sutherland,
and Gottlieb (1978)
11 ( – ) Duartin M acutifolium Vog. Kurosawa, Ollis, Redman, Sutherland,
Alves et al. (1978)
M. mucronulatum (Mart.) Kurosawa et al. (1978b)
Benth.
M. villosum Vog.
Alves et al. (1978)
12 ( – ) Mucroquinone M. mucronulatum (Mart.) Kurosawa et al. (1978b)
Benth.
Neoflavonoids and related compounds
13 Dalbergin M. scleroxylon Tul. Eyton et al. (1965)
M. pedicellatum Vog. Ogiyama and Yasue (1973)
M. kuhlmannii Hoehne Ollis, Redman, Roberts et al. (1978)
14 O-methyldalbergin M. scleroxylon Tul. Eyton et al. (1965)
15 Kuhlmannin M. pedicellatum Vog. Ogiyama and Yasue (1973)
M. nictitans (Vell.) Benth.
16 Kuhlmannene M. pedicellatum Vog. Ogiyama and Yasue 1973
17 Scleroin M. scleroxylon Tul. Eyton et al. (1965)
18 (R)-3,4- M. scleroxylon Tul. Eyton et al. (1965)
dimethoxydalbergione
(Continued)
4 Y. M. Amen et al.
Table 1. (Continued)
No. Compounds Species References
19 (R)-3,4- M. scleroxylon Tul. Eyton et al. (1965)
dimethoxydalber-
giquinol
20 (R)-40 -hydroxy-3,4- M. nictitans (Vell.) Benth. Ollis, Redman, Roberts et al. (1978)
dimethoxydalbergione
21 Kuhlmanniquinol M. kuhlmannii Hoehne Ollis, Redman, Roberts et al. (1978)
Flavanols
22 Procyanidin M. floribundum Waage et al. (1984)

Flavanones
23 Butin M. villosum Vog. Kurosawa et al. (1978b)
Flavones
24 Swertisin Machaerium hirtum Vell. Ignoato et al. (2013)
25 Isovitexin Machaerium hirtum Vell. Ignoato et al. (2013)
Chalcones
26 Isoliquiritigenin M. villosum Vog. Kurosawa et al. (1978b)
Benth.
27 Butein M. villosum Vog. Kurosawa et al. (1978b)
Benth.
Pterocarpans
28 (þ ) Medicarpin M. acutifolium Vog. Ollis, Redman, Sutherland et al. (1978)
M. nictitans (Vell.) Benth
and Gottlieb (1978)
M. aristulatum (Spruce ex Seo et al. (2001)
Benth.) Ducke.
29 (þ ) Homopterocarpin M. villosum Vog. Kurosawa et al. (1978b)
and Gottlieb (1978)
30 (þ ) Vesticarpan M. vestitum Vog. Kurosawa, Ollis, Redman, Sutherland,
and Gottlieb (1978)
31 Mucronucarpan M. mucronulatum (Mart.) Kurosawa et al. (1978b)
Benth.
M. villosum Vog.
32 (þ ) Maackiain M. aristulatum (Spruce ex Seo et al. (2001)
Benth.) Ducke
Alkaloids
33 4-Hydroxy-N- Machaerium hirtum Vell. Ignoato et al. (2013)
methylproline
Triterpenoids and steroids

34 b-amyrin acetate M. incorruptibile Fr. Magalhaes et al. (1966)
Allem
M. secundiflorum Mart. Formiga et al. (1975)
M. villosum Vog. Kurosawa et al. (1978b)
35 Erythrodiol 3-acetate M. incorruptibile Fr. Magalhaes et al. (1966)
Allem
36 O-acetyl-oleanolic M. incorruptibile Fr. Magalhaes et al. (1966)
aldehyde Allem
M. scleroxylon Tul. Eyton et al. (1965)

and Gottlieb (1978)
37 O-acetyl-oleanolic acid M. incorruptibile Fr. Magalhaes et al. (1966)
Allem
M. secundiflorum Mart Formiga et al. (1975)
38 Friedelin Machaerium hirtum Vell. Ignoato et al. (2013)
39 Lupeol Machaerium hirtum Vell. Ignoato et al. (2013)
40 b-sitosterol M. scleroxylon Tul. Eyton et al. (1965)
Fatty acids and derivatives

41 Methyl palmitate M. kuhlmannii Hoehne Ollis, Redman, Roberts et al. (1978)
Cinnamylphenols
42 Petrostyrene M. acutifolium Vog. Ollis, Redman, Sutherland et al. (1978)
43 Kuhlmannistyrene M. kuhlmannii Hoehne Ollis, Redman, Roberts et al. (1978)
44 Mucronustyrene M. villosum Vog. Kurosawa et al. (1978a)
Benth
45 Mucronulastyrene M. villosum Vog. Kurosawa et al. (1978a)
Benth
46 Villostyrene M. villosum Vog. Kurosawa et al. (1978a)
Benth
47 Macharistol M. aristulatum (Spruce ex Seo et al. (2001)
Benth.) Ducke.
Miscellaneous compounds
48 Machaeriol A M. multiflorum Spruce Ilias et al. (2001)
49 Machaeriol C M. multiflorum Spruce Ilias et al. (2003)
50 Machaeriol B M. multiflorum Spruce Ilias et al. (2001)
51 Machaeriol D
52 Machaeridiol A M. multiflorum Spruce Ilias et al. (2003)
53 Machaeridiol B
54 Machaeridiol C M. multiflorum Spruce Ilias et al. (2003)
55 (2 ) Kessane M. multiflorum Spruce Ilias et al. (2001)
56 Pinosylvin monomethyl M. acutifolium Vog. Ollis, Redman, Sutherland et al. (1978)
ether
57 Pinosylvin dimethyl M. opacum Vog. Ollis, Sutherland et al. (1978)
ether
58 2,3-Dimethoxyphenol M. kuhlmannii Hoehne Ollis, Redman, Roberts et al. (1978)
59 2,6-Dimethoxyphenol M. kuhlmannii Hoehne Ollis, Redman, Roberts et al. (1978)
M. mucronulatum (Mart.) Kurosawa et al. (1978a)
Benth
60 2-Hydroxy-3- M. kuhlmannii Hoehne Ollis, Sutherland et al. (1978)
methoxyphenol
61 2,3-Dimethoxybenzal- M. kuhlmannii Hoehne Ollis, Redman, Roberts et al. (1978)
dehyde
62 Methyl 3-(2-hydroxy-4- M. kuhlmannii Hoehne Ollis, Redman, Roberts et al. (1978)
methoxyphenyl)-
propionate
6 Y. M. Amen et al.
Papilionoideae of the Fabaceae (Veitch 2007). Several different nuclei of isoflavonoids have
been reported in the genus Machaerium as follows.
4.1.1. Isoflavones
These compounds have 3-phenyl-4H-1-benzopyran-4-one (3-phenylchromone) as a parent ring
system. Isolation of formononetin (1) was reported from different species including the
trunkwood of M. kuhlmannii Hoehne and M. nictitans (Vell.) Benth. by Ollis, Redman, Roberts
et al. (1978) and the trunkwood of M. vestitum Vog. by Kurosawa, Ollis, Redman, Sutherland,
and Gottlieb (1978). El-Sohly et al. (1999) reported its isolation together with its 30 -hydroxy
derivative (calycosin) (3) from the bark of M. aristulatum (Spruce ex Benth.) Ducke, while Seo
et al. (2001) reported its isolation from M. aristulatum (Spruce ex Benth.) Ducke stems.
Kurosawa et al. (1978b) reported the isolation of isoformononetin (2), daidzein (4) and 30 -
hydroxydaidzein (5) from the heartwood of M. villosum Vog. They also reported the isolation of
calycosin (3) from the wood of M. villosum Vog. and from the trunkwood and roots of M.
macronulatum (Mart.) Benth. and named it 30 -hydroxyformononetin.
R1 O
R3
O
R2
R1 R2 R3
1 OH OCH3 H Formononetin
2 OCH3 OH H Isoformononetin
3 OH OCH3 OH Calycosin
4 OH OH H Daidzein
5 OH OH OH 3'-Hydroxydaidzein
4.1.2. Isoflavans
Ogiyama and Yasue (1973) reported the isolation of three new isoflavans – machaerol A, B (6)
and C (7) – from the heartwood of M. pedicellatum Vog. In addition, Kurosawa, Ollis, Redman,
Sutherland, Alves et al. (1978) reported the isolation of (– ) mucronulatol (8) from the
trunkwood of M. vestitum Vog., the trunkwood and roots of M. mucronulatum (Mart.) Benth. and
from the heartwood of M. villosum Vog. while Ollis, Sutherland et al. (1978) reported its
isolation from the heartwood of M. opacum Vog. Kurosawa et al. (1978b) also reported the
isolation of a racemic mixture of mucronulatol (9) from M. mucronulatum (Mart.) Benth. and
(þ ) vestitol (10) from the trunkwood of M. vestitum Vog. Ollis, Sutherland et al. (1978) also
reported the isolation of duartin (11) from the heartwood of M. opacum Vog. while Kurosawa
et al. (b, c) isolated it from the trunkwood and roots of M. mucronulatum (Mart.) Benth., the
heartwood of M. villosum Vog. and from the heartwood of M. vestitum Vog. (2 ) Mucroquinone
(12) isolation was reported by Kurosawa et al. (1978b) from the trunkwood and roots of M.
mucronulatum (Mart.) Benth.
R1
R2 O
R3
R4 OCH3
R5
R1 R2 R3 R4 R5
6 OCH3 OCH3 OH OH OCH3 Machaerol B

7 OH OCH3 OH OH OCH3 Machaerol C
8 H H H OCH3 OH Mucronulatol
10 H H H OH H (+) Vestitol
OCH3
HO O
12 (–) Mucroquinone
O OCH3
4.1.3. Neoflavonoids and related compounds

Neoflavonoids are a further class of polyphenolic compounds, while flavonoids have the 2-
phenylchromen-4-one backbone; neoflavonoids have the 4-phenylchromen backbone with no
hydroxyl group substitution at position 2. These are presumed to be formed by cinnamoylation of a
benzenoid or polyketide precursor to give a 4-substituted series of flavonoids; alternatively, they can
be classified as 4-phenylcoumarins (Eyton et al. 1965). Eyton et al. (1965) reported the isolation of
dalbergin (13) and O-methyldalbergin (14) from the sap and heartwoods of M. scleroxylon Tul.
Previous isolations of these compounds have been restricted to Dalbergia species; D. sissoo and D.
latifolia and their isolation from a Machaerium species emphasises the close botanical relationship
between the Dalbergia and the Macherium genera (Ahluwalia & Seshadri 1957; Rao & Seshadri
1963; Eyton et al. 1965). Both compounds were further isolated by Ogiyama and Yasue (1973) from
the heartwood of M. pedicellatum Vog. Dalbergin (13) was also reported by Ollis, Redman, Roberts
et al. (1978) from the trunkwood of M. kuhlmannii Hoehne. Eyton et al. (1965) reported the isolation
of the benzophenone derivative, scleroin (17), from M. scleroxylon Tul.
Eyton et al. (1965) added that the co-occurrence of the dalbergiones and dalbergins suggests
that they have a common biosynthetic origin in which cinnamyl pyrophosphate (or its equivalent)
is the postulated precursor of the neoflavonoids. It is suggested that the natural dalbergiones,
dalbergins, and benzophenones are inter-related as transformation products of neoflavonoids.
Eyton et al. (1965) also reported the isolation of (R)-3,4-dimethoxydalbergione (18) and (R)-
3,4-dimethoxydalbergiquinol (19) from the sapwood of M. scleroxylon Tul, and then Ogiyama
and Yasue (1973) reported again these two compounds from the heartwood of M. pedicellatum
Vog. which were further isolated by Ollis, Redman, Roberts et al. (1978) from the trunkwood of M.
8 Y. M. Amen et al.
kuhlmannii Hoehne. Ollis, Redman, Roberts et al. (1978) reported a new member (R)-40 -hydroxy-
3,4-dimethoxydalbergione (20) from the trunkwood of M. nictitans (Vell.) Benth. Ogiyama and
Yasue (1973) reported the isolation of kuhlmannin (15) and kuhlmannene (16) from the
heartwood of M. pedicellatum Vog. Both compounds were further isolated from the trunkwood of
M. kuhlmannii Hoehne. and M. nictitans (Vell.) Benth. by Ollis, Redman, Roberts et al. (1978).
Kuhlmannene (16) was optically inactive and its structure was confirmed by its formation when a
chloroformic solution of (R)-3,4-dimethoxydalbergione was passed over a column of neutral
alumina. Ollis, Redman, Roberts et al. (1978) reported another member, kuhlmanniquinol (21),
from the trunkwood of M. kuhlmannii Hoehne and M. nictitans (Vell.) Benth.
R1
H3CO O O
R1 R2
R2 13 H OH Dalbergin
14 H OCH3 O-methyldalbergin
15 OCH3 OH Kuhlmannin
OCH3
OCH3
H3CO O
H3CO OH
HO O
16 Kuhlmannene HO 17 Scleroin
OCH3
H3CO O
18 R= H (R)-3,4-dimethoxydalbergione
O
H 20 R= OH (R)-4'-hydroxy-3,4-dimethoxydalbergione
R
OCH3
H3CO R1 R1 R2
19 OH H (R)-3,4-dimethoxydalbergiquinol
21 OCH3 OH Kuhlmanniquinol
HO
H
R2
4.1.4. Flavanols
A procyanidin (22) was isolated from an alcoholic extract of M. floribundum by Waage et al.
(1984). The procyanidin consists of an average of four units.
OH
OH
HO O
OH
OH
OH
O
HO OH
OH
HO O OH
OH OH
OH
22 Procyanidin unit
4.1.5. Flavanones
Butin (23) was reported by Kurosawa et al. (1978b) from the heartwood of M. villosum Vog.
OH
HO O
OH
23 Butin
4.1.6. Flavones
Ignoato et al. (2013) reported the isolation of swertisin (24) and isovitexin (25) from the leaves
and branches of Machaerium hirtum Vell.
OH
RO O
HO
O
R
HO 24 CH3 Swertisin
OH
HO 25 H Isovitexin
OH O
10 Y. M. Amen et al.
4.1.7. Chalcones
Kurosawa et al. (1978b) reported the isolation of isoliquiritigenin (26) and butein (27) from the
heartwood of M. villosum Vog. and from the trunkwood of M. mucronulatum (Mart.) Benth.
R3
OH
HO R1
R1 R2 R3
26 OH H H Isoliquiritigenin
R2 O 27 H OH OH Butein
4.1.8. Pterocarpans
The pterocarpans are one of the larger subclasses of Fabaceae isoflavonoids. They have been
mainly found in a large number of species belonging to diverse sub-families of Fabaceae.
Pterocarpans can be described as benzo-pyrano-furano-benzenes which can be formed from
isoflavones by internal coupling of the B ring to the 4-ketone position (Pistelli et al. 2003; Veitch
2007, 2013). Pterocarpans constitute the second largest group of natural isoflavonoids (Jimenez
et al. 2008). Isolation of (þ ) medicarpin (28) was reported by Ollis, Redman, Roberts et al. (1978)
and Ollis, Redman, Sutherland et al. (1978) from different species of Machaerium including the
sapwood of M. acutifolium Vog., the trunkwood of M. kuhlmannii Hoehne, M. nictitans (Vell.)
Benth. and the trunkwood of M. vestitum Vog. which was further reported by Seo et al. (2001) from
the stems of M. aristulatum (Spruce ex Benth.) Ducke. (þ ) Homopterocarpin (29) was reported by
Kurosawa, Ollis, Redman, Sutherland, and Gottlieb (1978) and Kurosawa et al. (1978b) from the
heartwood of M. villosum Vog. and from the trunkwood of M. vestitum Vog. They also reported
the isolation of (þ ) vesticarpan (30) from the trunkwood of M. vestitum Vog., besides the isolation
of mucronucarpan (31) from the trunkwood and roots of M. mucronulatum (Mart.) Benth. and
from the heartwood of M. villosum Vog. Seo et al. (2001) reported the isolation of (þ ) maackiain
(32) from the stems of M. aristulatum (Spruce ex Benth.) Ducke.
R1 O
R2
OCH3
R3
R1 R2 R3
28 OH H H (+) Medicarpin
HO O 29 OCH3 H H (+) Homopterocarpin
30 OH H OH (+) Vesticarpan
31 OCH3 OH OH Mucronucarpan
O O 32 (+) Maackiain
O
4.2. Alkaloids
4-Hydroxy-N-methylproline (33) was reported by Ignoato et al. (2013) from the leaves and
branches of Machaerium hirtum Vell. This is the only report for the presence of alkaloids in
genus Machaerium.
HO
COOH
N
33 4-Hydroxy-N-methylproline
CH3
4.3. Triterpenoids and steroids

Magalhaes et al. (1966) reported the isolation of pentacyclic triterpenoids of b-amyrin type;
b-amyrin acetate (34), erythrodiol 3-acetate (35), O-acetyl-oleanolic aldehyde (36) and O-acetyl-
oleanolic acid (37) from the benzene extract of the sapwood of M. incorruptibile Fr. Allem. They
stated that the isolation of the previous four compounds from a single plant source belonging to the
Fabaceae may be regarded as illustrating an acceptable biosynthetic sequence in plants. Isolation
of O-acetyl-oleanolic aldehyde (36) was previously reported by Eyton et al. (1965) from the sap
and heartwoods of M. scleroxylon Tul., and this was the first report of this compound as a natural
product. It was further reported by Formiga et al. (1975) from the trunkwood of M. secundiflorum
Mart. and by Kurosawa, Ollis, Redman, Sutherland, and Gottlieb (1978) from the trunkwood of M.
vestitum Vog. Isolation of b-amyrin acetate (34) was further reported by Ogiyama and Yasue
(1973) from the heartwood of M. pedicellatum Vog., by Formiga et al. (1975) from the trunkwood
of M. secundiflorum Mart. and by Kurosawa et al. (1978b) from the sapwood of M. villosum Vog.
together with erythrodiol 3-acetate (35). O-acetyl-oleanolic acid (37) was isolated by Formiga
et al. (1975) from the trunkwood of M. secundiflorum Mart. and by Ollis, Redman, Roberts et al.
(1978) from the trunkwood of M. kuhlmannii Hoehne. Friedelin (38) and lupeol (39) was reported
by Ignoato et al. (2013) from the leaves and branches of Machaerium hirtum Vell. b-sitosterol (40)
was isolated from the sapwood of M. scleroxylon Tul. by Eyton et al. (1965), and then by Formiga
et al. (1975) from the trunkwood of M. secundiflorum Mart., by Ollis, Redman, Roberts et al.
(1978) from the trunkwood of M. kuhlmannii Hoehne and also by Kurosawa et al. (1978b) from the
sap and heartwoods of M. villosum Vog.
H R
34 R=CH3 β-amyrin acetate

H
35 R=CH2OH Erythrodiol 3-acetate
H3COCO 36 R=CHO O-acetyl-oleanolic aldehyde
H
37 R=COOH O-acetyl-oleanolic acid
O
HO
38 Friedelin 39 Lupeol
HO 40 β-sitosterol
4.4. Fatty acids and derivatives

Methyl palmitate (41) was isolated from the trunkwood of M. kuhlmannii Hoehne by Ollis,
Redman, Roberts et al. (1978).
CH3(CH2)14COOCH3 41 Methyl palmitate
4.5. Cinnamylphenols
Various cinnamylphenols were isolated from different species of Machaerium including
petrostyrene (42) from the sapwood of M. acutifolium Vog. (Ollis, Redman, Sutherland et al.
1978), kuhlmannistyrene (43) from the trunkwood of M. kuhlmannii Hoehne (Ollis, Redman,
Roberts et al. 1978), mucronustyrene (44) by Kurosawa et al. (1978a) from the heartwood of M.
villosum Vog. and from the trunkwood and roots of M. mucronulatum (Mart.) Benth.,
muronulastyrene (45) by Kurosawa et al. (1978a) from the heartwood of M. villosum Vog. and
the trunkwood and roots of M. mucronulatum (Mart.) Benth., villostyrene (46) by Kurosawa
et al. (1978a) from the heartwood of M. villosum Vog. and the roots of M. mucronulatum (Mart.)
Benth. and macharistol (47) by Seo et al. (2001) from the stems of M. aristulatum (Spruce ex
Benth.) Ducke. Kuhlmannistyrene (43), Mucronulastyrene (45) and villostyrene (46) showed a
cis-configuration rather than a trans-configuration. The cinnamylphenol, petrostyrene (42), is
the trans-isomer of kuhlmannistyrene (43).
R2
R3 O OCH3 R1
R4
R1 R2 R3 R4
42 OH OCH3 CH3 OH Petrostyrene (E-form)
43 OH OCH3 CH3 OH Kuhlmannistyrene (Z-form)
44 H OCH3 H H Mucronustyrene
45 OH OCH3 H H Mucronulastyrene
46 OCH3 OCH3 H H Villostyrene
47 H OH CH3 OH Macharistol
4.6. Miscellaneous compounds

Miscellaneous organic compounds were isolated from different species of Machaerium. Ilias et al.
(2001) stated that bioassay-guided fractionation of the stem bark of M. multiflorum Spruce yielded
the hitherto unreported (þ )trans-hexahydrodibenzopyrans; machaeriol A (48) and machaeriol B
(50) as well as a guaiane sesquiterpene (2 ) kessane (55) (previously isolated from Valeriana
officinalis). This was the first report of the hexahydrodibenzopyrans from a higher plant other than
the genus cannabis. In 2003, they reported the isolation of new (þ )trans-hexahydrodibenzopyr-
ans; machaeriol C (49), machaeriol D (51) and three new 5,6-seco- hexahydrodibenzopyrans;
machaeridiol A (52), machaeridiol B (53) and machaeridiol C (54) from the same plant. Ollis,
Sutherland et al. (1978) and Ollis, Redman, Sutherland et al. (1978) reported the stilbenes;
pinosylvin monomethyl ether (56) and dimethyl ether (57) from the heartwood of M. opacum Vog.
From the sapwood of M. acutifolium Vog., Ollis, Redman, Sutherland et al. (1978) reported the
isolation of pinosylvin monomethylether (56). Ollis, Redman, Roberts et al. (1978) and Ollis,
Sutherland et al. (1978b) reported the isolation of different benzene derivatives from the
trunkwood of M. kuhlmannii Hoehne including 2,3- and 2,6-dimethoxyphenols (58,59), 2-
hydroxy-3-methoxyphenol (60), 2,3-dimethoxybenzaldehyde (61) and methyl 3-(2-hydroxy-4-
methoxyphenyl)-propionate (62). Ollis, Sutherland et al. (1978) reported also the isolation of 2,3-
dimethoxyphenol (58) from the heartwood of M. opacum Vog. 2,6-Dimethoxyphenol (59) was
reported by Kurosawa et al. (1978a) from the trunk wood of M. mucronulatum (Mart.) Benth.
HO
48 R= H Machaeriol A
49 R= OH Machaeriol C
O
H
HO
O
H
50 R= H Machaeriol B
51 R= OH Machaeriol D
O
R
H
R
HO
H
52 R= H Machaeridiol A
53 R= OH Machaeridiol B
OH
HO
O
H
54 Machaeridiol C
OH
O
H
H
55 (–) Kessane
H
R
56 R = OH Pinosylvin monomethyl ether

57 R = OCH3 Pinosylvin dimethyl ether
O
R1
R1 R2 R3
R2 58 OH OCH3 OCH3 2,3-Dimethoxyphenol
59 OCH3 OH OCH3 2,6-Dimethoxyphenol
60 OH OH OCH3 2-Hydroxy-3-methoxyphenol
R3 61 CHO OCH3 OCH3 2,3-Dimethoxybenzaldehyde
O
62 Methyl 3-(2-hydroxy-4-methoxyphenyl)-propionate
O OH
5. Traditional uses
The plants belonging to Machaerium are used as antitussive and the sap is used to cure aphthous
ulcers of the mouth (Joly et al. 1987). Joly et al. reported also that ethereal extract from the wood
of M. villosum is active in vivo cercarial (Schistosoma mansoni) penetration inhibition in mouse
by external application. In South America, the geographical origin of Machaerium, M.
floribundum is used by indigenous population to treat diarrhoea (Heinrich et al. 1992) and its
roots in Costa Rica are used in the form of decoction for menstrual cramps (Ginzbarg 1977).
Neither the mechanism nor the compounds responsible for these uses were revealed up till now.
Economically, the heartwood of Machaerium scleroxylon Tul. is used in Brazil as a commercial
substitute for the true jacaranda wood obtained from Dalbergia nigra (Eyton et al. 1965).
6. Biological activities
6.1. Cytotoxic effect
From the stems of Machaerium aristulatum, Seo et al. (2001) reported the isolation of two
cytotoxic compounds, including a new cinnamylphenol, macharistol (47) along with a known
pterocarpan, (þ ) medicarpin (28). Both compounds showed moderate cytotoxic activity in the
KB (a human oral epidermoid carcinoma) cell line with EC50 values of 1.7 and 2.4 mg/mL,
respectively. Additional studies were performed with macharistol (47) in which the KB, Col-2
(colon), and hTERT-RPE1 (human telomerase reverse transcriptase-retinal pigment epithelial)
cell lines were evaluated with the in vivo murine hollow fibre test. At the highest dose (25 mg/kg
body weight) tested, macharistol (47) showed 23% and 0% inhibition of growth of KB cells
implanted at the intraperitoneal (i.p.) and subcutaneous (s.c.) compartments of mice,
respectively. At this dose, inhibition of growth of Col-2 cells (35%) was also observed both at
the i.p. and s.c. sites. The growth of hTERT-RPE1 was inhibited by 31% and 45% at the i.p. and
s.c. sites, respectively. No significant weight loss was observed in test mice in all cases.
6.2. Antimicrobial and Antiparasitic activities

Waage et al. (1984) stated that a procyanidin (22) isolated from an alcoholic extract of M.
floribundum, inhibited the growth of Pseudomonas maltophilia. In 1999, El-Sohly et al. reported
that an activity was found against Giardia protozoa in an ethanolic extract of M. aristulatum
bark. Bioassay-guided fractionation resulted in the isolation of formononetin (1) and calycosin
(3) responsible for the activity.
Machaerium biovulatum agglutinin (MBA) and M. lunatus agglutinin (MLA) at
0.4 mg mL21 prevented the cytopathic effect of HIV (Animashaun et al. 1993). This is of
course an interesting find and unique among the species of Machaerium.
Ilias et al. (2001) stated that an ethanolic extract of the stem bark of M. multiflorum showed
sufficient antimalarial and antibacterial activities in a bioassay-guided fractionation. Re-
extraction of the active, dried EtOH extract of M. multiflorum with n-hexane, followed by DCM,
resulted in localisation of the antimalarial and antibacterial activities in the n-hexane fraction.
Machaeriol B (50) was proved responsible for the antimalarial activity. Machaeriol B (50)
showed inhibition of the growth of chloroquine-resistant P. falciparum clone (IC50 ¼ 120 ng/
mL). Machaeriol A (48) was found to be weakly active. When tested for antibacterial activity
against Staphylococcus aureus and methicillin-resistant S. aureus using a modified microplate

assay, machaeriol B (50) showed inhibitory activities against both the organisms with IC50
values of 5 and 4.5 mg/mL.
Ilias et al. (2003) reported that machaeriol C (49) demonstrated in vitro antibacterial activity
against Staphylococcus aureus and methicillin-resistant S. aureus (MRSA), while its
corresponding 5,6-seco-analogues machaeridiol A (52) and machaeridiol B (53) showed
antifungal activity against Candida albicans in addition to antibacterial activity against the same
organisms. Machaeridiol B (53) also demonstrated antiparasitic activities against Plasmodium
falciparum D6 (chloroquine-sensitive) and W2 (chloroquine-resistant) clones and against
Leishmania donavani.
6.3. Anti-inflammatory activity

Ignoato et al. (2013) reported that crude extracts of leaves and branches of M. hirtum Vell.
exhibited a significant anti-inflammatory activity. They evaluated the anti-inflammatory activity
using the mouse ear edema model, including myeloperoxidase (MPO) assays.
6.4. Antioxidant activity

The antioxidant activity of Machaerium villosum ethanolic extract was studied by Santos et al.
(2009) on the free radicals DPPH (2,2-diphenyl-1-picrylhydrazyl) and TEMPOL (4-hydroxy-
2,2,6,6-tetramethylpiperidinyloxy-1-oxyl). They used electron paramagnetic resonance (EPR)
for selective detection of free radicals. The extract displayed a remarkable antioxidant activity
against the radicals DPPH and TEMPOL. Furthermore, Diaz et al. (2011) reported that the
ethanolic extract of Machaerium floribundum revealed a significant antioxidant activity using
DPPH test. They confirmed the antioxidant activity of the plant extract by measuring its capacity
to reduce Feþ3 to Feþ2, monitored by the formation of a coloured complex (Fenton type
reaction) and also by measuring the cellular viability of the fibroblasts. They added that the
antioxidants are involved in the repair of cutaneous tissues affected by acne. Their results also
indicated that the ethanolic extract of Machaerium floribundum showed a good antibacterial
activity against the bacteria that are involved in the inflammatory process of acne. As a result,
Diaz et al. (2011) suggested the use of the plant against acne.
7. Conclusion
Reviewing the genus Machaerium helped us to identify certain species that are traditionally used
but still unknown phytochemically. That would be useful for other researchers to identify the
specific compounds present in these species which may explain their traditional uses and also
open the door for new constituents which may have promising biological activities. In addition,
for many species, for example Machaerium villosum which in part was studied phytochemically,
no biological activity is reported up till now. Many other species are still unknown
phytochemically and biologically. Following these species may be of a great importance in
discovering new bio-active compounds.
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Pharmacognosy Department, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt

(Received 26 September 2014; final version received 21 December 2014)

Taxonomy Historical consideration Phytochemistry Traditional uses Biological activities

Machaerium, in the family Fabaceae, predominantly is a genus of a Neotropical

*Corresponding author. Email: yhiyaamen@gmail.com

q 2015 Taylor & Francis

4.1. Flavonoids and related compounds

Table 1. Compounds isolated from the genus Machaerium.

22 Procyanidin M. floribundum Waage et al. (1984)

Triterpenoids and steroids

M. scleroxylon Tul. Eyton et al. (1965)

M. villosum Vog. Kurosawa et al. (1978b)

Fatty acids and derivatives

6 OCH3 OCH3 OH OH OCH3 Machaerol B

4.1.3. Neoflavonoids and related compounds

4.3. Triterpenoids and steroids

34 R=CH3 β-amyrin acetate

4.4. Fatty acids and derivatives

CH3(CH2)14COOCH3 41 Methyl palmitate

4.6. Miscellaneous compounds

56 R = OH Pinosylvin monomethyl ether

6.2. Antimicrobial and Antiparasitic activities

against Staphylococcus aureus and methicillin-resistant S. aureus using a modified microplate

6.3. Anti-inflammatory activity

6.4. Antioxidant activity

Bernardi L. 1984. Contribución a la Dendrologia Paraguaya: I. Boissiera. 35:317.

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