Cogent Biology

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Anise (Pimpinella anisum L.), a dominant spice

and traditional medicinal herb for both food and
medicinal purposes

Wenli Sun, Mohamad Hesam Shahrajabian & Qi Cheng |

To cite this article: Wenli Sun, Mohamad Hesam Shahrajabian & Qi Cheng | (2019) Anise
(Pimpinella anisum L.), a dominant spice and traditional medicinal herb for both food and
medicinal purposes, Cogent Biology, 5:1, 1673688, DOI: 10.1080/23312025.2019.1673688

To link to this article: https://doi.org/10.1080/23312025.2019.1673688

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Sun et al., Cogent Biology (2019), 5: 1673688
https://doi.org/10.1080/23312025.2019.1673688

PLANT SCIENCES | REVIEW ARTICLE

Received: 08 May 2019
Accepted: 16 September 2019
First Published: 30 September 2019
*Corresponding author: Wenli Sun,
Biotechnology Research Institute,
Chinese Academy of Agricultural
Sciences, Beijing 100081, China.
E-mail: sunwenli@caas.cn, cheng-
qi@caas.cn (All authors contributed
qually to this research)
Reviewing editor::
Sabrina Sabatini, Sapienza University
of Rome, Italy ** All authors con-
tributed equally to this work.
Additional information is available at
the end of the article
Anise (Pimpinella anisum L.), a dominant spice
and traditional medicinal herb for both food and
medicinal purposes
Wenli Sun1,2* ** , Mohamad Hesam Shahrajabian1,2 ** and Qi Cheng1,2 **
Abstract: Aromatic plants such as anise seed have a long traditional use in both
folk and conventional medicine and of course in the pharmaceutical industry.
Important compounds found in anise seed include estragol, p-anisaldehyde, anise
alcohol, acetophenone, pinene, and limonene, but the most important volatile oil
that gives the characteristic sweet, aromatic flavor to seeds is anethole. The recent
studies have shown that anise seeds and essential oil have antioxidant, antibac-
terial, antifungal, anticonvulsant, anti-inflammatory, analgesic, gastro-protective,
antidiabetic, and antiviral activities. Other important benefits of anise seeds are
stimulant, carminative, expectorant, insecticide, vermifuge, digestive, antispasmo-
dic, antirheumatic, antiseptic, antiepileptic, antihysteric, culinary significance, keeps
the heart strong by its importance role to control the blood pressure, one of the best
gas-releasing agent, eases many hormonal problems in females, hair benefits, skin
benefits, and it may reduce symptoms of depression. Anise seed and its extract also
use in savory dishes, baked goods, and different drinks in both ancient and modern
time. Anise seeds are good source of many essential B-complex vitamins such as
pyridoxine, niacin, riboflavin, and thiamin. The seeds are also important source of

ABOUT THE AUTHORS PUBLIC INTEREST STATEMENT

Dr. Wenli Sun is an assistant researcher working
on related topics of allelopathic characteristics
of medicinal plants, especially traditional Asian
herbs, fruits and crops. She is also working on
topics related to sustainable agriculture and
farming. Her full profile is available in http://
orcide.org/0000-0002-1705-2996
Dr. Mohamad Hesam Shahrajabian is a senior
researcher of Agronomy and Biotechnology. His
full profile is available in https://orcide.org/0000-
0002-8638-1312
Prof. Dr. Qi Cheng, is a professor of biotech-
nology and his researches have connected with
agrobiotechnology and agrotechnology. His full
profile is available in http://orcide.org.0000-
0003-1269-6386. All these scholars are
researchers in Biotechnology Research Institute,
Chinese Academy of Agricultural Sciences, and
Nitrogen Fixation Laboratory, Qi Institute,
Building C4, No. 555 Chuangye Road, Jiaxing
314000, Zhejiang, China (Corresponding
author).
Pimpinella asnisum L. is an aromatic, annual
grassy herb with 30–50 cm height, white flowers
and small green to yellow seeds with secondary
feather like leaflets of bright green, twice pinnate.
Keeping the traditional knowledge of Chinese
medicine and other Asian medicine is vital
requirement for not only saving traditional
Chinese medicine are not only important cultural
resources, but also can be used as organic pro-
ducts to have sustainable life. Anise seed oil con-
tains anethol, estragole, eugenol,
pseudisoeugenol, methyl chavicol and anisalde-
hyde, coumarins, scopoleting, umbelliferon,
estrols, terpene hydrocarbons, and polyacety-
lenes as the major compounds. The plant oil has
both pharmacological and clinical effects. The
pharmacological effects consist of antimicrobial,
hepatopreotective, anticonvulsant, anti-inflam-
matory, antispasmodic, bronchodilator, estro-
genic, expectorant, and insecticidal effects, and
clinical effects such as nausea, constipation,
menopausal period, virus, diabetes, obesity, and
sedative action.

© 2019 The Author(s). This open access article is distributed under a Creative Commons
Attribution (CC-BY) 4.0 license.

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minerals like calcium, copper, potassium, iron, manganese, magnesium, and zinc.
Antioxidant vitamins such as vitamin C and A can also be found in the spice. More
clinical studies are necessary to uncover the numerous substances and their effects
in ginseng that contribute to public health.

Subjects: Botany; Conservation - Environment Studies; Biodiversity & Conservation

Keywords: Health benefits; traditional Chinese medicine; traditional Asian medicine;

clinical aspect; anethole

1. Introduction

1.1. Anise occurrence and cultivation

Traditional medicinal herbs have been used for both food and medicinal purposes, which have
obvious role in maintaining human health and improving human life quality for thousands of years
(Ogbaji, Li, Xue, Shahrajabian, & Egrinya, 2018; Shahrajabian, Sun, & Qi, 2018, 2019a, 2019b, 2019c;
Soleymai & Shahrajabian, 2018; Soleymani & Shahrajabian, 2012a, 2012b; Soleymani,
Shahrajabian, & Naranjani, 2013). China has important potential to produce aromatic and medical
plants and herbs due to its various biological diversity and different climatic conditions (Chen et al.,
2013; Ogbaji, Shahrajabian, & Xue, 2013; Shahrajabian, Soleymani, Ogbaji, & Xue, 2017; Yong et al.,
2017). Aromatic plants such as anise seed have a long traditional use in both folk and conventional
medicine and of course in the pharmaceutical industry (Abouzid & Mohamed, 2011; Ibrahim,
Mattar, Abdel-Khalek, & Azzam, 2017; Sevindik, Murathan, Yamaner, & Ayvaz, 2016;
Shahrajabian, Khoshkharam, Zandi, Sun, & Qi, 2019e, Shahrajabian, Sun, & Cheng, 2019f,
Shahrajabian, Sun, & Qi, 2019d). Anise (Pimpinella anisum) is a herbaceous annual plant, native
to Mediterranean region and primarily grown for both fruits and seeds (Zand, Darzi, & Haj Seyed
Hadi, 2012). It has been reported, it is also indigenous to Iran, India, and Turkey (Kucukkurt et al.,
2009). Its fruits, known also as aniseed, were used as traditional medicine in China as early as in
the 5th century. Fruits of this plant contain fatty oil, proteins, carbohydrates, and cellulose fibers. In
European countries, consumption of anise fruits is more than its production so the amount of
imported anise fruits reached about 2,000 t in 2004 (Ullah, Mahmmod, & Honermeier, 2014).
Among other countries Germany remains the largest spice importer of anise (Rapisarda, 2004).
Sirisha and Sujathamma (2018) noticed that anise usually grows on dry rocky places, rocky
crevices, fields, meadows, mountains pastures, and grasslands, and its seed germination in nature
is very poor.

1.2. Anise classification and variation species

The Pimpinella anisum has common names in different countries such as: Anis vert (France); Anise
seed (Japan); Anise and Star anise (the USA); Annesella (Italy); Anisa, Badian, Kuppi, Muhuri, Saunf
and Sop (Iran and India); Boucage anis, Petit anise (North Africa), and anise (England) (Khare,
2007; Ross, 2001). Information on scientific names, common names, uses, origins, cultivation
potential toxic compounds, and toxicity is shown in Table 1.

1.3. Anise nutritional composition and chemical constituents

Anethole which is used in pharmaceutical, food, perfumery, and flavoring industry, is the most
important constituent of anise (Ozkan & Chalchat, 2006; Tuncturk & Yildirim, 2006). The yield and
anethole content of aniseed are affected by the genotype, the ecological conditions, and especially
by agricultural practices such as the irrigation, plant population, fertilizer, and planting date
(Acimovic et al., 2014; Asadi-kavan, Ghorbanli, Pessaraki, & Sateei, 2009; Ozel, 2009). Apart from
anethole, anise is well known for essential oil, which gives it the characteristics odor and aroma.
Although, the major component of anise oil is trans-anethole (75–90%), other constituents include
coumarins (umbelliferone, umbelliprenine, bergapten, and scopoletin), lipids (fatty acids, beta-
armyrin, stigmasterol, and its salts), flavonoids (flavonol, flavone, glycosides, rutin, isoorientin,

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 Sun et al., Cogent Biology (2019), 5: 1673688

Table 1. Plant spices known as anise

Scientific names and Common names Uses Origin/Introduction Cultivation Potentially toxic Toxicity
https://doi.org/10.1080/23312025.2019.1673688

synonyms to Europe compounds

Pimpinella anisum Linne Anise, anis vert, aniseed Carminative, Middle East/introduced Mediterranean Anethole Relatively safe
(Umbeliferae family) antispasmodic, by the Moors
expectorant, insecticide,
bactericide, aromatic;
manufacture of
preserves, liquirs, and
confectionery
Illicium verum Hooker Star anise, Chinese star Antioxidant, Asia/17th century Southeast Asia Anethole, estragole, Toxic at high doses
filius; Illicium anisatum anise, badiane antimicrobial, veranisatin A, B, and C
Lour (Magnoliaceae expectorant, analgesic,
family) and sedative
Illicium anisatum Linne, Japanese star anise, No clear medicinal Asia Sotheast Asia Anethole Anisatins Highly toxic (not
Illicium japonicum, shikimmi, skimmi effects authorized use)
Illicium religiosum

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Table 2. Mean values or components of anise essential oil analyzed by GC-MS (Ullah, Mahmood, &
Honermeier, 2013)
No. Components Kovats retention %
index
1 Estragol 1,197 0.33
2 Cis-Anethole 1,252 0.14
3 Trans-Anethole 1,287 82.1
4 δ-Elemene 1,333 0.45
5 β-Elemene 1,388 0.08
6 α-Himachalene 1,449 0.71
7 γ-Himachalene 1,478 7.0
8 α-Amorphane 1,482 0.15
9 (E)-Methylisoeugenol 1,489 0.14
10 α-Zingiberene 1,493 0.77
11 β-Himachalene 1,499 0.44
12 α-Muurolene 1,502 0.15
13 β-Bisabolene 1,506 0.38
14 β-Sesquipehllandrene 1,522 0.05
15 Spathulenol 1,580 0.04
16 Unknown 1,629 0.05
17 α-Cadinol 1,651 0.08
18 Unkown 1,831 5.95
19 Unknown 1,886 0.92
No. of identified compounds.

and isovitexin), protein, and carbohydrate (Picon et al., 2010; Yamini, Bahramifar, Sefidkon,
Saharkhiz, & Salamifar, 2008). It has been reported that apiaceae seed are used in food industry
such as bread, biscuits, and cookies as ingredients, and in meat industry, Apiaceae are favorable
spices. (Acimovic, Kostadinovic, Popovic, & Dojcinovic, 2015). Components of anise essential oil
analyzed by GC-MS are shown in Tables 2 and 3. Anise methanolic extract and molecular formula is
shown in Table 4. Chemical composition (%) of oleoresins of anise is shown in Table 5.

The oil content and fatty acid composition of anise is shown in Table 6. Composition of
Pimpinella anisum essential oil (%) of various origins has been shown in Table 7. Properties of
aniseed oil Are shown in Table 8. Total phenols, carotenoids, and tannins in ethanolic extract of
anise are shown in Table 9. HPLC-analysis of polyphenolic compounds in ethanolic extracts of anise
is shown in Table 10. Oil yield and fatty acid composition of Tunisian and Egyptian anise seeds
(Table 11).

1.4. Potential health benefits, medicinal uses of anise in modern medicine industry
Seeds of anise are used as analgesic in migraine and also as carminative, aromatic, disinfectant
and diuretic in traditional medicine (Amin, 2005). In some traditional texts, anise is mentioned for
melancholy, nightmare, and also in treatment of epilepsy and seizure (Mirheydar, 2001). Shobha,
Rajeshwari, and Andallu (2013) noticed that aniseed is a potent antiperoxidative and antidiabetic
agent and thereby, possess a vast spectrum of applications and exploitations in the food and drug
industry. Cifti, Guler, Dalkilic, and Nihat Ertas (2005) showed that anise oil has anethole as active
ingredients and also eugenol, methylchavicol, anisaldehyde, and estragole. Rebey et al. (2017)
revealed that aniseeds might constitute a novel source of natural antioxidants and could be used
as food additive. Acimovic et al. (2014) found that drought cause a significant decrease in
thousand seed weight, germination energy, and total germination as well as essential oil content

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Table 3. Chemical composition of Pimpinella anisum essential oil analyzed by GC/MS (Singh,
Kappor, Singh, de Heluani, & Caralan, 2008)
Compound %MS RI# Identification Φ
α-pinene 0.1 927 MS,RI,co-GC
Sabinene t 964 MS,RI,co-GC
Myrcene t 983 MS,RI,co-GC
Αα-phellandrene t 998 MS,RI,co-GC
p-cymene 0.1 1018 MS,RI,co-GC
Limonene 0.8 1023 MS,RI,co-GC
1,8-cineole 0.1 1026 MS,RI,co-GC
Cis-β-ocimene t 1029 MS,RI,co-GC
Fenchone 5.0 1083 MS,RI,co-GC
Camphor 0.2 1138 MS,RI,co-GC
Methyl chavicol 2.3 1192 MS,RI
Endo-fenchyl acetate 0.1 1224 MS,RI,co-GC
Cis-anethole 0.5 1247 MS,RI
p-anisaldehyde 0.5 1253 MS,RI
Trans-anethole 90.1 1294 MS,RI
Total 99.9%
Trace ˂0.05; # the retention index (RI) was calculated using a homologous series of n-alkanes C8-C18;Φco-GC:
coinjection with an authentic sample. Percentages are the mean of three runs and were obtained from electronic
integration measurements using selective mass detector.

Table 4. Anise methanolic extract and molecular formula

No. Compound name Molecular formula
1 Anethole C10H12O
2 Varidiflorene C15H24
3 Eicosane C20H42
4 Docosane C22H46
5 Nonadecane C19H40
6 Pentadecane C15H32
7 Butanoic acid C15H20O3
8 Heneicosane C21H44
9 Octacosane C28H58
10 Hexadecane C20H42
11 Cyclohexane C26H50

in anise. Contrary to this finding, the content of trans-anethole was significantly higher in the dry
year. Ibrahim (2008) reported that according to the traditional thinking, drinking anise by boys
maybe harmful to their reproductive system. Kreyidyyeh, Usta, Knio, Markossian, and Dagher
(2003) found that extracts of the aniseeds are used as medicine for their diuretic and laxative
effect, expectorant and antispasmodic action, and their ability to ease gastric pain and flatulence.
Ibrahim et al. (2017) reported that waste residues of anise and star anise are promising new
sources of phenolic antimicrobial compounds, which offer new commercial opportunities to phar-
maceutical industry. They have suggested that combination of anise waste extracts with some
antibiotics leads to new choice for treatment of infectious diseases and waste extracts may act as
activity modifying agent for antibiotics. Islam, Khan, Rakhshanda, Mahdi, and Chowdhury (2016)

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 Table 5. Chemical composition (%) of oleoresins (in various solvents) of Pimpinella anisum analyzed by GC/MS (Singh et al., 2008)
Sun et al., Cogent Biology (2019), 5: 1673688

Compounds PS2 PS3 PS4 PS5 RI# Identification Φ

https://doi.org/10.1080/23312025.2019.1673688

p-cymene — — t — 1028 MS,RI,co-GC

Limonene t — 0.5 t 1031 MS,RI,co-GC
1,8-cineole — — t — 1034 MS,RI,co-GC
Cis-β-ocimene — — t — 1039 MS,RI,co-GC
Fenchone 1.2 0.3 0.9 0.4 1093 MS,RI,co-GC
Undecane t — — 0.3 1100 MS,RI,co-GC
Camphor t t t — 1149 MS,RI,co-GC
Methyl chavicol t — 0.5 t 1201 MS,RI
Endo-fenchyl acetate t t t t 1226 MS,RI
p-anisaldehyde t — t t 1258 MS,RI
Trans-anethole 14.1 5.7 19.7 6.4 1295 MS,RI
Palmitic acid, methyl t 0.3 t t 1914 MS,RI
ester
Plamitic acid 8.5 7.9 5.3 5.7 1968 MS,RI,co-GC
Palmitic acid, ethyl ester 1.2 — — — 1981 MS,RI,co-GC
Linoleic acid, methyl t 0.7 0.1 t 2080 MS,RI,co-GC
ester
Oleic acid methyl ester t 2.8 0.4 0.5 2086 MS,RI,co-GC
Oleic acid 57.9 75.5 57.5 63.5 2130 MS,RI,co-GC
Oleic acid, ethyl ester 11.0 — — — 2146 MS,RI,co-GC
Stearic acid 1.9 — — — 2157 MS,RI,co-GC
2-oleoylglycerol 2.3 2.8 2.1 3.6 — MS
Squalene — t 0.2 t — MS
Octacosanal t t 0.4 0.6 — MS
Stigmasterol t t 0.4 0.5 — MS
PS2: ethanol extract; PS3: methanol extract; PS4: -hexane extract; PS5: petroleum benzene extract. Trace: ˂0.05; # the retention index (RI) was calculated using a homologous series of n-alkanes C6-C22;
Φ coinjection with an authentic sample. Percentages are the mean of three runs and were obtained from electronic integration measurements using a selective mass detector.

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Table 6. Oil content and fatty acid composition of anise (Alfekaiki, 2018)
Element Mineral contents (%)
Carbon 34.5
Oxygen 21.1
Nitrogen ND
Aluminum 20.5
Bromine 14
Iron ND
Copper 3.63
Lanthanum 5.85
Palladium 0.35
Sulfur 0.15
Potassium ND
Magnesium ND

Table 7. Composition of Pimpinella anisum essential oil (%) of various origins (Saibi, Belhadj, &
Benyoussef, 2013)
Components Algeria Reported
compositions
Turkey Turkey Portugal
Linalool 0.3 - 0.8 -
Terpinene 4-ol - - 0.6 -
Methyl chavicol - - 0.8 -
α-terpineol - - 1.0 -
Estragol 1.9 0.6 - 2.2
Anisaldehyde - 0.9 0.5 1.9
Cis-anethole 0.5 0.3 0.1 Tr
Trans-anethole 92.4 95.4 89.5 92.5
Methy eugenol - - 0.6 -
γ-himachalene 1.1 0.8 - -
Zingiberene 0.3 - - -
Anesic acid - 0.5 - -
Anisylacetone 0.3 - 0.2 -
Anisyl alcohol - - 0.1 -
o-isoeugenol 1.9 - 0.2 -
Trans-Pseudoisoeugenyl-2- - - - 0.1
methybutyrate
Butanoic acid, 2-methyl-,4- 0.3 - - -
methody-2(3-methyloxiranyl)
phenyl ester

reported that aniseed extracts showed positive antibacterial effects on only three bacteria, named,
Bacillus cereus, Bacillus subtilis, and Streptococcus pneumonae. They have also found that the
phytochemical analysis of the aqueous extract revealed the presence of alkaloids, flavonoids,
saponins, tannins, terpenoids, phenolic compounds, and cardiac glycosides. Fouda, Elewady,
Shalabi, and Habouba (2014) indicated that the anise extract shows good performance as corro-
sion inhibitor 1 M HCl, and also the anise extract inhibits the corrosion by getting adsorbed on the

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Table 8. Properties of aniseed oil (Yadav, Mahadwad, Kshirsagar, & Gite, 2015)
Sr. no. Parameter Results
1 Color Pale yellow
2 Specific gravity 0.987
3 Saponification value 168.3
4 Acid value 2.55
5 Iodine value 99
6 Refractive index 1.55
7 Odor Sweet like Anethole

Table 9. Total phenols, carotenoids, and tannins in ethanolic extract of anise (Tolba, El-Sherif, &
El-Sherif, 2012)
Total phenols (as mg gallic acid) 64.63
Carotenoids (mg/100g) 23.33
Tannins (mg as tannic acid) 83.31

Table 10. HPLC-analysis of polyphenolic compounds in ethanolic extracts of anise

Compound Anise
Rt Area (%) ppm
Protocatchoi - - -
Catechein 2.467 1.2923 3.310
Pyrogallo 2.494 1.4354 6.391
Chlorogenic 2.785 4.0396 2.875
Caffeic - - -
Vanillic - - -
Syrinic 3.933 1.0083 0.137
Caffeine - - -
P. coumaric 6.090 0.6257 0.060
Ferullic - - -
Salycilic 6.541 2.3829 1.704
Coumarin 6.679 1.3413 0.132
Cinnamic 8.447 0.2376 0.017
Chrisin 11.708 0.2359 1.285
Hypersoid 4.936 3.9599 47.103
Quecettin 7.384 1.2037 17.239
Luteolin 7.756 1.8574 159.300
Kampferol 8.757 0.5232 7.177
Apegnin 8.860 0.3272 6.880
Total area of phenolic 7360.32203
compounds
Total area of flavonoid 7681.33273
compounds

etal surface following Langmuir adsorption isotherm. Positive antimicrobial effects produced by
methanol, ethanol, and aqueous extract of aniseed are shown in Table 12. Antifungal activity of
the essential oils, which expressed through the minimal inhibitory concentrations, is shown in

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Table 11. Oil yield and fatty acid composition (%) of Tunisian and Egyptian anise (Pimpinella
anisum) seeds (means of six replicates ± S.D). Values with different superscripts (a-b) are sig-
nificantly different at p ˂ 0.05 (Rebey et al., 2017)
TAS EAS
Oil yield (%) 11.60 ± 0.03a 9.82 ± 0.02b
Saturated fatty acid (SFA)(%)
Capric acid (C10:0) 0.16 ± 0.03a 0.11 ± 0.01a
a
Lauric acid (C12:0) 0.52 ± 0.01 0.44 ± 0.02a
Myristic acid (C14:0) 0.07 ± 0.01a 0.02 ± 0.00a
b
Palmitic acid (C16:0) 4.90 ± 0.22 13.20 ± 0.09a
a
Stearic acid (C18:0) 0.85 ± 0.04 0.66 ± 0.01a
Arachidic acid (C20:0) 0.07 ± 0.01a 0.07 ± 0.00a
Total 6.57 14.5
Unsaturated fatty acid (UFA)(%)
Petroselinic acid (C18:1 Δ6) 46.60 ± 0.22a 38.40 ± 0.11b
Oleic acid (C18:1 Δ9) 21.05 ± 0.08 a
18.47 ± 0.13b
a
Lioleic acid (C18:2) 22.99 ± 0.44 23.18 ± 0.22a
Linolenic acid (C18:3) 1.07 ± 0.01a 0.58 ± 0.04b
Total 91.71 80.63
Notes: Values with different superscripts (a-b) are significantly different at p ˂ 0.05 (means of six replicates); SFA:
saturated fatty acid; UFA: unsaturated fatty acid.

Table 13. Positive phytochemical assay of aniseed in aqueous extract is shown in Table 14.
Antifungal activity of anise fluid extract and essential oil by the diffusion method is shown in
Table 15. Antifungal activity of anise fluid extract and essential oil by the dilution method is shown
in Table 16.

Qualitative analysis of methanolic extract and various fractions is shown in Table 17.
Phytoceuticals in methanolic extract and various fractions of aniseed is shown in Table 18.
Essential oil composition of Tunisian and Egyptian anise seeds is shown in Table 19.

Table 12. Positive antimicrobial effects (average zone of inhibition) produced by methanol,
ethanol, and aqueous extract of aniseed, and that in positive controls (Islam et al., 2016)
Extraction Day of Zone of
condition extraction inhibition (mm)
Bacillus cereus Bacillus subtilis Streptococcus
pneumonae
Methanol extraction 2nd day 19.03 ± 1.53 18.77 ± 0.55 12.07 ± 1.39
5th day 20.13 ± 0.32 19.27 ± 1.2 14.5 ± 0.65
th
7 day 18.43 ± 1.15 15.63 ± 1.16 14.87 ± 0.96
Positive controls 28.61 ± 0.91 23.44 ± 0.5 31.67 ± .88
Ethanol extraction 2nd day 14.90 ± 0.36 14.01 ± 0.7 12.17 ± 0.12
th
5 day 14.52 ± 0.95 12.19 ± 0.9 13.00 ± 0.7
7th day 14.78 ± 0.94 16.08 ± 1.36 14.44 ± 1.17
Positive controls 28.20 ± 1.3 23.80 ± 1.47 31.39 ± 1.67
nd
Aqueous extraction 2 day 11.05 ± 0.69 10.83 ± 1.18 -
Positive controls 29.56 ± 0.91 24.83 ± 1 -
The results represent the mean ± SD of values obtained from three independent experiments.

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Table 13. Antifungal activity of the essential oils is expressed through the minimal inhibitory
concentrations (mg/ml) (Starovic et al., 2016)
Fungal species Anise
Bipolaris/Drechslera sorociniana 0.325
Fusarium subglutinans 0.0775
Fusarium verticillioides 0.325
Fusarium oxysporum 0.55
Fusarium tricinctum 0.325
F. sporotrichioides 0.055
F. equiseti 5.5
F. incarnatum 7.75
Macrophomina phaseolina 0.325
F. proliferatum 7.75
*Values of MIC, followed by the same letter are not significantly different (p ˂ 0.05) according to Duncan,s multiple
range test.

Table 14. Positive phytochemical assay of aniseed in aqueous extract (Islam et al., 2016)
S1. No Test Interference Results
1 Tannin Bluish-black or brownish-green precipitate Present
2 Saponin Frothing Present
3 Terpenoid Reddish brown precipitate Present
4 Flavonoid Appearance of yellow color Present
5 Cardiac glycoside Appearance greenish and violet ring Present
6 Alkaloids Creamy-white precipitate Present
7 Phenolics Appearance of dark green color Present
8 Steroid Appearance of red colored product Present
Ghazanfarpour, Sadeghi, Abdolahian, and Roudsari (2016) showed that anise can alleviate the side effects of hot
flashes, so they suggest usage of herbal medicine can be seen as an alternative treatment for women experiencing
hot flashes.

Antimicrobial activity of anise EO in disc-diffusion method is shown in Table 20. The major
molecular compounds identified in the essential oils of cumin, clove, cinnamon, anis, and laurel
using gas chromatography mass spectrometry (GC-MS) is shown in Table 21. Minimum inhibitory
concentration (MIC) of anise EO is shown in Table 22. Antioxidant activity of aniseed extracts as
affected by maturity stages is shown in Table 23. GC-MS chromatography of anise oil components
is shown in Table 24.

Values are mean ± SEM of three replicates.

ND = not detected.

Alfa-pinene, estragole, anethole, β-Himachalene, α-Himachaelen, cyclohexene, and 2-Methoxy-

5-(1-propenyl) phenol are shown in Figures 1–7.

Minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) of anise
dried extract on different fungi species is shown in Tables 25 and 26, respectively. Biochemical
reactions leading to phenylpropenes in plant and the reactions catalyzed by known enzymes is
shown in Figure 8.

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Table 15. Antifungal activity of anise fluid extract and essential oil by the diffusion method
(Kosalec, Pepeljnjak, & Kustrak, 2005)
Fungi Inhibition zone
(mm)
Reference Fluid extract Essential oil
substancea
Yeasts Candida albicans 18 12 29
C. tropicalis 23 11 AEc
C. pseudotropicalis 18 10 AEc
C. parapsilosis 18 11 30
C. krusei 17 11 AEc
C. glabrata 18 0 21
Geotrichum spp. 19 GPAb 17
Dermatophytes Trichophyton 21 20 25
rubrum
T. mentagrophytes 24 29 23
Microsporum canis 21 26 27
M. gypseum 21 23 21
a
Nistatin as reference substance (0.5 mg mL−1) for yeasts and ketoconazole for dermatophytes.
b
GPA, growth promotion activity.
C
AE, fungicidal influence of aerosol (0.7 µL cm−3).

Uysal, Kara, Algur, Dumlupinar, and Nuri Aydogan (2007) reported that fruits of anise use for
treatment of infections, angina, bronchitis, gastritis, laryngitis, and migraine. Mohamed,
Abdelgadir, and Almagboul (2015) showed that the petroleum ether, chloroform, ethyl acetate,
and methanol extracts of P. anisum (1:10 and 2:10) were highly active (30–40 mm) against B.
subtilis. The ethyle acetate extract exhibited moderate activity (15 mm) against Escherichia coli
and low activity (13 mm) against Ps. aeruginosa. The methanol extract of P. anisum showed high
activity (16 mm) against E. coli, low activity (13 mm) against Ps. aeruginosa, and the methanol
extract have variable activity against all test organisms.

Yazdani et al. (2009) concluded that anise can be a candidate for further studies due to their
antifungal potencies. Rebey et al. (2019) indicated that the determination of optimal periods and
provenances for antioxidant accumulation can be used to evaluate the quality of aniseeds and could
be important for industries. Khudor, Jasim, Malik, and Zahra (2013) mentioned that Pimpinella
anisum and some antibiotics by disc diffusion methods and minimum inhibitory concentration, the
results showed these bacterial isolates were sensitive to the aqueous extract compared with
methanol, acetone, and petroleum ether and were more sensitive to vancomycin compared with
other antibiotics. Karimzadeh et al. (2012) indicated the anticonvulsant and neuroprotective effects
of anise oil, likely via inhibition of synaptic plasticity. Bagdassarian, Bagdassarian, and Atanassova
(2013) stated that the seeds of anise are rich in phytochemical contents, which possessed high
antioxidant and antimicrobial activities and they can be used for health supplement and pharma-
ceutical benefits. Aydemir, Cifci, Aviyente, and Bosgelmez-Tinaz (2018) observed that trand-anethole
has the potential to inhibit QS (Quorum sensing)-regulated virulence factors in P. aeruginosa by
binding to LasR protein, similar to its natural ligand N-(3-oxododecanoyl)-L-homoserine lactone.
Mahood (2012) concluded that anise oil extract can decrease signs of polycystic ovary syndrome
(PCOS) in the ovarian tissue and altered concentrations of luteinizing hormone. Singh et al. (2008)
stated that the antioxidant potency of anise oil and its methanol and ethanol oleoresins, can be
utilized for protecting fat-containing foods. Diaz et al. (2014) stated that mixture of chamomile and
star anise decrease the completion percentage of the activated carbon, delayed the appearance of
diarrhea and decrease the number of evacuations in comparison with the control treatments. They

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 Table 16. Antifungal activity of anise fluid extract and essential oil by the dilution method (Kosalec et al., 2005)
Sun et al., Cogent Biology (2019), 5: 1673688

Fungi Antifungal
https://doi.org/10.1080/23312025.2019.1673688

activity
Reference Fluid extract Essential oil
substancea (%, V/V) (%, V/V)
(µg mL−1)
MICb MFCc MIC MFC MIC MFC
Yeasts Candida albicans 0.5 1 19 25 1.00d 2.00d
C. parapsilosis 1 2 18 25 0.10d 0.20d
C. tropicalis 1 2 18 25 0.10d 0.20d
d
C. pseudotropicalis 0.5 1 17 20 0.20 0.39d
d
C. krusei 0.5 1 20 25 0.20 0.39d
C. glabrata 2 4 nt nt 0.10d 0.20d
d
Geotrichum spp. 2 4 nt nt 1.56 3.12d
d
Dermatophytes Trichophyton rubrum 0.25 0.5 1.5 3 0.20 0.39d
T. mentagrophytes 0.50 1 9.0 20 0.78d 1.56d
d
Microsporum canis 0.25 0.5 2.5 5 0.10 0.20d
d
M. gypseum 0.25 0.5 7.0 15 0.20 0.39d
a
Nistatin as reference antimycotic against yeasts tested and ketoconazole against dermatophytes tested.
b
MIC, minimum inhibitory concentration.
c
MFC, minimum fungicidal concentration.
d
Significantly different from fluid extract (p˂0.01).
Nt, not tested.

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Table 17. Qualitative analysis of methanolic extract and various fractions (Shobha & Andallu,
2016)
Test Me He Be Ea n-But Aq
Carbohydrates
a. Molisch test + - - + - ++
b. Fehling,s test - - - - - +
c. Barfoed,s test - - - - - -
,
d. Benedict s test - - - - - +
Amino acids
a. Ninhydrin test + - - + - ++
,
b. Hopkin s-Cole test - - - - - -
c. Erhlich,s test - - - - - -
d. Pauly,s test - - - - - -
e. Nitroprusside test - - - - - -
Flavonoids
a. Sodium hydroxide test ++ + + +++ + +
b. Sodium acetate test ++ + + +++ + +
c. Sulfuric acid test ++ + + +++ + +
Polyphenols and tannins
a. Ferric chloride test ++ + + +++ + +
b. Potassium dichromate test ++ + +++ + +
c. Potassium ferricyanide test ++ + +++ + +
Sappnins
a. Foam test + ++ ++ + +
Sterols
a. Leibermann Buchard,s test + +++ + + +
b. Salkowski test + ++ - +
Me, Methanolic extract; He, Hexane; Be, Benzene; Ea, ethyl acetate; n-But, n-Butanol; Aq, Aqueous

have suggested the combination of chamomile and star anise as an alternative antidiarrheal
treatment. Ibrahim (2008) concluded that anise oil administration inhibited GST expression, besides
decreasing testosterone, T3 and T4 hormones and inhibiting sperm counts and sperm motility. Al-
Omari, Qaqish, and Al-Qaoud (2018) concluded that anise possesses immunomodulatory activity
when apply orally in mice and selectively activates cell-mediated immune mechanisms. Cifti et al.
(2005) indicated that anise is an annual herb indigenous to Iran, India, Turkey, and many other
warm regions and it could be considered as a potential natural growth promoter for poultry. Amina,
Nadia, Kahloulakhaled, Nesrine, and Abdelkader (2016) showed that the aqueous extract of P.
anisum L. can have a corrective effect against nephrotoxicity induced by lead, so P. anisum L. has
a beneficial impact on the kidneys intoxicated with lead acetate. Mosaffa-Jahromi et al. (2017)
suggested that anise oil could be a promising choice of treatment for depressed patients with
irritable bowel syndrome. Shahamat, Abbasi-Maleki, and Mohammadi Motamed (2015) concluded
that P. anisum possesses an antidepressant-like activity similar to that of fluoxetine, which has a
potential clinical value for application in the management of depression. Felsociova et al. (2015)
reported that the most hopeful antifungal activity and killing effect against all tested penicillia was
found to be Pimpinella anisum and Origanum vulgare L. Rattan, Satpathy, and Gupta (2014) showed
that a formulation of biscuits with anise extract was prepared for enhancing the healthy beneficial
usage of biscuits and nutraceutical, in conditions like cough or sore throat with a simultaneous
attainment of the other health benefits. Kargozar, Azizi, and Salari (2017) stated that Pimpinella
anisum is effective in the treatments of acute menopausal syndrome with different mechanisms.

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Table 18. Phytoceuticals in methanolic extract and various fractions of aniseed (Shobha &
Andallu, 2016)
Sample extract Total phenolic Total flavonoids Total Flavonols
(mg/100 g) GAE (mg/100 g) RE (mg/100 g) RE
Methanol 0.63 ± 2.3 0.32 ± 0.9 0.47 ± 1.9
Hexane 0.16 ± 2.9 0.20 ± 0.5 0.24 ± 0.5
Benzene 0.23 ± 0.6 0.27 ± 1.4 0.34 ± 0.3
Ethyl acetate 0.77 ± 0.3 0.45 ± 1.6 0.55 ± 0.1
n-butanol 0.42 ± 1.7 0.15 ± 1.1 0.41 ± 0.9
Aqueous 0.15 ± 2.1 0.07 ± 1.7 0.08 ± 1.4
Values are mean ± SEM of three replicates.

Table 19. Essential oil composition of Tunisian and Egyptian anise (Pimpinella anisum) seeds
(means of six replicates ± S.D). Values with different superscripts (a-b) are significantly different at
p ˂ 0.05 (Rebey et al., 2017)
% %
Compunds* RIa RIb TAS EAS
Terpene 0.13 0.04
hydrocarbons
Linalool 1097 1557 0.13 ± 0.01a 0.04 ± 0.04b
Oxygenated 0.06 0.02
monoterpene
α-Terpinene 1018 1249 0.06 ± 0.01a 0.02 ± 0.00a
Phenylpropanoids 95.78 94.99
a
Anisole 918 1720 0.97 ± 0.05 0.52 ± 0.03b
b
Estragole 1197 1430 0.20 ± 0.03 3.74 ± 0.13a
Trans-anethole 1253 1740 94.30 ± 0.01a 90.41 ± 0.22b
a
p-Anisaldehyde 1250 1718 0.17 ± 0.01 0.10 ± 0.07a
a
Cis-isoeugenol 1359 2180 0.14 ± 0.01 0.22 ± 0.02a
Sesquiterpene 3.95 2.48
hydrocarbons
β-Elemene 1388 1465 0.07 ± 0.66a 0.09 ± 2.11a
a
γ-Himachalene 1484 1690 2.32 ± 0.04 1.08 ± 0.01b
Zingiberene 1494 1672 0.30 ± 0.03a 0.25 ± 0.03a
β-Himachalene 1505 1942 0.12 ± 0.02 a
0.11 ± 0.01a
b
β-Bisabolene 1506 1832 0.19 ± 0.02 0.85 ± 0.01a
Isolongifolene 1532 2003 0.04 ± 0.00a 0.02 ± 0.00a
a
Diepi-α-cedrene 1575 2020 0.91 ± 0.02 0.08 ± 0.00b
Total identified 99.74 97.53
Notes: Volatile compounds percentages in the same line with different letters (a-b) are significantly different at p ˂
0.05 (means of six replicates). RIa order of elution in apolar column (HP-5); RIb order of elution in polar column (HO
Innowax), MS: mass spectrum.

Barbalho et al. (2015) suggested that P. anisum has potential to be used to control lipid levels.
Radaelli et al. (2016) suggested that the use of essential oil from anise might serve as an alternative
to the use of chemical preservatives in the control and inactivation of pathogens in commercially
produced food systems. Kucukkurt et al. (2009) demonstrated that aniseed could be used at 30 g/kg
level in quail diets an increased antioxidant activity with glutathione (GSH) and a decreased blood
malondialdehyte (MDA) levels. Abdel-Reheem and Oraby (2015) found that Pimpinella anisum

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Table 20. Antimicrobial activity of P. anisum EO in disc-diffusion method (30 µl/disc) (Abdel-
Reheem & Oraby, 2015)
Microorganism Inhibition zones in
mm
P. anisum oil Corn oil Streptomycin
Staphylococcus aureus 15 0 19
Streptococcus pyogenes 12 0 17
Escherichia coli 15 2 19
Salmonella typhi 17 1 20
Pseudomonas aeruginosa 10 0 15
Enterococcus faecalis 16 0 18
Micrococcus luteus 14 3 20
Candida albicans 10 1 ND
ND= not detected.

essential oil residuals have high inhibitory effect for Salmonella typhi, Enterococcus faecalis,
Staphylococcus aureus, E. coli, and Micrococcus Iuteus. Pavela (2014) stated has the essential oil
from Pimpinella anisum fruits and trans-anethole were toxic for Daphnia magna (62–92% mortality)
and significantly reduced it fertility at high concentrations (35–50 µL mL−1) and long exposure (48 h).
However, no negative effect on Daphnia mortality or fertility was found at shorter exposure times
(6 h) and lower concentrations (20 µL mL−1). Womeni, Djikeng, Tiencheu, and Linder (2013) found
that the powder of Pimpinella anisum has a special potent antioxidants for stabilization of crude
soybean oil. Changizi-Ashtiyani et al. (2017) observed that the simultaneous use of ethanolic extract
of P. anisum during gentamicin (GM) administration is recommended to reduce its nephrotoxicity
effects. Barbalho et al. (2015) reported that P. anisum has potential to be used to control lipid levels.
Kadan, Rayan, and Rayan (2013) noted that anise could be one of the foods that attribute to cancer
prevention and treatment. It could be a natural source of novel anticancer compounds with anti-
proliferative and apoptotic properties. Bekara et al. (2015) observed that aniseed aqueous extract
was effective in reducing the level of some of biochemical parameters and ameliorate behavior of
intoxicated rats by lead. Nahidi, Kariman, Simbar, and Mojab (2012) concluded that P. anisum is
effective on the frequency and severity of hot flashes in postmenopausal women. Hosseinzadeh,
Tafaghodi, Abedzadeh, and Taghiabadi (2014) stated that P. anisum aqueous and ethanolic extracts
can increase milk production in rats. Sharifi, Kiani, Farzaneh, and Ahmadzadeh (2008) reported that
anise is commercially cultivated in Iran and has been used in medicinal applications; moreover, their
oil can be effective for protection of fresh fruits facing fungi and its essential oil can be considered as
a potential, broad spectrum and safe substitute of chemical agents. Ashraffodin Ghoshergir et al.
(2015) showed the effectiveness of anise in relieving the symptoms of postpartum depression.
Shirzadi, Abbasi-Maleki, and Zanbouri (2017) noted that P. anisum ethanolic extract is effective in
suppression of morphine physical dependence and further studies are needed to find out the
responsible constituents and also the exact mechanisms of actions. Niksokhan, Hedarieh,
Najafifard, and Najafifard (2015) observed that 250 and 300 mg/kg of hydroalcoholic extract of P.
anisum seed significantly increased the duration of open arm ledges and decreased the duration of
closed arm ledges in maze; in addition, this treatment resolved anxiety and relieved anxiety in rats.
Nikfarjam, Bahmani, and Heidari-Soureshjani (2016) decribed that Pimpinella anisum is one the most
important native medicinal plants of Iran with antianxiety properties. Amini, Tajabadi, Khani, Labbafi,
and Tavakoli (2018) identified components of the essential oils and obtained results showed that
Pimpinella anisum L. showed the most fumigant toxicity on the storage pests. The pharmacological
effect of anise is shown in Table 27.

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 Table 21. The major molecular compounds identified in the essential oils of cumin, clove, cinnamon, anis, and laurel using gas chromatography mass spectrometry
Sun et al., Cogent Biology (2019), 5: 1673688

(GC-MS) (Sergio, Fabiola, Guadalupe, Blanca, & Leon, 2013)

https://doi.org/10.1080/23312025.2019.1673688

Essential oils
Compound Cumin Clove Cinnamon Anis Laurel
(Cuminum cyminum) (Eugenia cyryophyllata) (Cinnamomum verum) (Pimpinella anisum) (Laurus nobilis)
α-Pinene × ×
Limonene × × ×
γ-Terpinene ×
Cuminaldehyde ×
Alcohol cuminic ×
Eugenol ×
Caryophyllene × ×
Acetate of eugenyle ×
Chavicol ×
Carene × ×
Cinnamaldehyde ×
Geraniol ×
β-Myrcene ×
Germancrene ×
Eucalyptol ×
Ocimene ×
Trans-anethol ×
Cis-anethol ×

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Table 22. Minimum inhibitory concentration (MIC) of Pimpinella anisum EO (Abdel-Reheem &
Oraby, 2015)
Microorganism Inhibition zones in
mm
P. anisum oil Corn oil Streptomycin
Staphylococcus aureus 3.0 N 1.5
Streptococcus pyogenes 4.0 N 1.0
Escherichia coli 2.5 10.0 1.5
Salmonella typhi 2.0 N 1.5
Pseudomonas aeruginosa 3.0 N 1.5
Enterococcus faecalis 2.0 N 1.0
Micrococcus luteus 2.0 9.0 1.5
Candida albicans 4.0 N ND
ND = not detected, N = bacteria not effected at any concentration.

Table 23. Antioxidant activity of aniseed (Pimpinella anisum L.) extracts as affected by maturity
stages (Rebey et al., 2019)
Antioxidant
assays
DPPH Chelating ability Reducing power
(IC50 µg/mL) (IC50 mg/mL) (EC50 µg/mL)
Turkey Immature 103.45 108.8 1234.28
Intermediate 42.97 57.81 947.05
Mature 18.97 12.46 684.73
Serbia Immature 153.18 122.76 982.27
Intermediate 58.04 68.09 687.41
Mature 20.18 10.89 565.11
Egypt Immature 103.02 130.55 1080.39
Intermediate 62.17 68.51 764.22
Mature 16.77 13.17 618.82
Tunisia Immature 96.21 97.34 1154.33
Intermediate 35.27 52.84 755.88
Mature 12.87 9.23 523.47

Table 24. GC-MS chromatography of anise oil components (Obaid, Al Janabi, & Taj-Aldin, 2017)
No. Compound Rt (min) M. Weight Area
1 Alfa-pinene 5.61 136 0.63
2 Estragole 13.81 148 3.7
3 Anethole 15.99 148 18.54
4 β-Himachalene 20.9 204 8.5
5 Αα-Himachalene 21.87 204 6.6
6 cyclohexene 22.84 82 2.01
7 2-Methoxy-5-(1- 31.05 164 2.93
propenyl) phenol

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Figure 1. Alfa-pinene.

Figure 2. Estragole.

Figure 3. Anethole.

Figure 4. β-Himachalene.

2. Conclusion
The followings conclusion could be drawn for the discussions. Pimpinella asnisum L. is an aromatic,
annual grassy herb with 30–50 cm height, white flowers and small green to yellow seeds with
secondary feather like leaflets of bright green, twice pinnate. Due to all positive characteristics,
such as antidiabetic, hypolipidemic, antioxidant activities, anticancer, and antimicrobial properties,
both seeds and essential oils of anise is promising for safe use as super food supplements and raw
constituents in the both pharmaceutical and food industries. Keeping the traditional knowledge of
Chinese medicine and other Asian medicine is vital requirement for not only saving traditional

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Figure 5. α-Himachaelen.

Figure 6. Cyclohexene.

Figure 7. 2-Methoxy-5-(1-pro-
penyl) phenol.

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Table 25. Minimum inhibitory concentration (MIC) of P. anisum dried extract on different fungi
species (Yazdani et al., 2009)
Dried extract
concentration
(mg/ml)
Fungi species 64 32 16 8 Control
Aspergillus niger - - - - -
Candida albicans + + + - -
Microsporum canis + + + - -
Epidermophyton + + + - -
fluccosum
Trichophyton + + + - -
mentagrophytes
+ = Positive inhibition, - = Negative inhibition

Table 26. Minimum fungicidal concentration (MFC) of P. anisum dried extract on different fungi
species (Yazdani et al., 2009)
Dried extract
concentration
(mg/ml)
Fungi species 256 128 64 32 16 8 4 control
Aspergillus niger - - - - - - - -
Candida albicans + - - - - - - -
Microsporum canis + + - - - - - -
Epidermophyton + + + + + + - -
fluccosum
Trichophyton + + + + - - - -
mentagrophytes
+ = Positive inhibition, - = Negative inhibition

Figure 8. Biochemical reactions

leading to phenylpropenes in
plants. The reactions catalyzed
by known enzymes are indi-
cated (Koeduka, Baiga, Noel, &
Pichersky, 2009) .

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Table 27. The pharmacological effects of Pimpinella anisum (Shojaii & Abdollahi Fard, 2012)
System Effect
Organism Antibacterial
Antifungal
Insecticidal
Antiviral
Muscle Muscle relaxant of tracheal chain
Antispasmodic and relaxant of anococygeus smooth muscle
Nervous system Anticonvulsant
Analgesic
Conditioned place aversion in morphine dependence
Gastrointestinal Laxative
Increase glucose absorption from the jejunum
Renal Reduce volume of urine by increase activity of the renal Na+-K+-ATPase
Endocrine Antidiabetic
Hypolipidemic
Immune system Antioxidant
Others Reduction of menopausal hot flashed
Growth promoter of day-old broilers
Reduction of pain in dysmenorrhea

Chinese medicine as the important cultural resources, but also using organic products to have
sustainable life. Anise seed oil contains anethol, estragole, eugenol, pseudisoeugenol, methyl
chavicol and anisaldehyde, coumarins, scopoleting, umbelliferon, estrols, terpene hydrocarbons,
and polyacetylenes as the major compounds. The plant oil has both pharmacological and clinical
effects. The pharmacological effects consist of antimicrobial, hepatopreotective, anticonvulsant,
anti-inflammatory, antispasmodic, bronchodilator, estrogenic, expectorant and insecticidal effects,
and clinical effects such as nausea, constipation, menopausal period, virus, diabetes, obesity, and
sedative action. More clinical studies are necessary to uncover the numerous substances and their
effects in ginseng that contribute to public health.

Funding References
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microbial, cytotoxicity, and necrotic ripostes of
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