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Star anise ( Illicium verum ): Chemical compounds, antiviral properties, and clinical relevance

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Medicinal herbs are one of the imperative sources of drugs all over the world. Star anise (Illicium verum), an evergreen, medium‐sized tree with star‐shaped fruit, is an important herb with wide distribution throughout southwestern parts of the Asian continent. Besides its use as spice in culinary, star anise is one of the vital ingredients of the Chinese medicinal herbs and is widely known for its antiviral effects. It is also the source of the precursor molecule, shikimic acid, which is used in the manufacture of oseltamivir (Tamiflu®), an antiviral medication for influenza A and influenza B. Besides, several other molecules with numerous biological benefits including the antiviral effects have been reported from the same plant. Except the antiviral potential, star anise possesses a number of other potentials such as antioxidant, antimicrobial, antifungal, anthelmintic, insecticidal, secretolytic, antinociceptive, anti‐inflammatory, gastroprotective, sedative properties, expectorant and spasmolytic, and estrogenic effects. This review aimed to integrate the information on the customary attributes of the plant star anise with a specific prominence on its antiviral properties and the phytochemical constituents along with its clinical aptness.
Star anise (Illicium verum): Chemical compounds, antiviral
properties, and clinical relevance
Jayanta Kumar Patra
| Gitishree Das
| Sankhadip Bose
Sabyasachi Banerjee
| Chethala N. Vishnuprasad
Maria del Pilar Rodriguez-Torres
| Han-Seung Shin
Research Institute of Biotechnology &
Medical Converged Science, Dongguk
University-Seoul, Goyang-si 10326, Republic
of Korea
Department of Pharmacognosy, Bengal
School of Technology, Sugandha, Hooghly
712102, West Bengal, India
Department of Phytochemistry, Gupta
College of Technological Sciences, Asansol,
West Bengal, India
Centre for Ayurveda Biology and Holistic
Nutrition, The University of Trans-Disciplinary
Health Sciences and Technology (TDU),
Bengaluru, Karnataka, India
Laboratorio de Ondas de Choque (LOCH),
Centro de Física Aplicada y Tecnología
Avanzada (CFATA), Universidad Nacional
Autónoma de México Campus UNAM Juriquilla
Boulevard Juriquilla no. 3001 Santiago de
Querétaro, Qro., C.P. 76230, Mexico
Department of Food Science &
Biotechnology, Dongguk University-Seoul,
Goyang-si 10326, Republic of Korea
Dr. Jayanta Kumar Patra, Research Institute of
Biotechnology & Medical Converged Science,
Dongguk University-Seoul, Goyang-si 10326,
Republic of Korea.
Medicinal herbs are one of the imperative sources of drugs all over the world. Star
anise (Illicium verum), an evergreen, medium-sized tree with star-shaped fruit, is an
important herb with wide distribution throughout southwestern parts of the Asian
continent. Besides its use as spice in culinary, star anise is one of the vital ingredients
of the Chinese medicinal herbs and is widely known for its antiviral effects. It is also
the source of the precursor molecule, shikimic acid, which is used in the manufacture
of oseltamivir (Tamiflu
), an antiviral medication for influenza A and influenza
B. Besides, several other molecules with numerous biological benefits including the
antiviral effects have been reported from the same plant. Except the antiviral
potential, star anise possesses a number of other potentials such as antioxidant, anti-
microbial, antifungal, anthelmintic, insecticidal, secretolytic, antinociceptive, anti-
inflammatory, gastroprotective, sedative properties, expectorant and spasmolytic,
and estrogenic effects. This review aimed to integrate the information on the cus-
tomary attributes of the plant star anise with a specific prominence on its antiviral
properties and the phytochemical constituents along with its clinical aptness.
antiviral, Illicium verum, oseltamivir, shikimic acid, star anise, Tamiflu
Plants are a vital part of the ancient system of medicine for treating
numerous infectious and non-infectious diseases across the globe.
The rich repository of bioactive compounds such as phenols, terpe-
noids, alkaloids, and so forth make them an important source of drug
(Sasidharan, Chen, Saravanan, Sundram, & Latha, 2011). Generally,
the use of herbal remedies for treating various disease conditions is
more common in rural places where the accessibility to the foods
and also medical services is limited (Bukar, Dayom, & Uguru, 2016).
People usually consume plants in different forms, namely, infusions,
spices, and medicinal smoke. Also, some of the plants are used as
seasoning substances to add flavor to the foods provide health bene-
fits (Bagchi & Srivastava, 2003).
Star anise (SA: Illicium verum Hook. f.), better known as Chinese
SA, belongs to the Magnoliaceae family and is an aromatic plant. It
has a star shape, and its fruit is a very important element as a spice in
the Oriental cuisine. It is a highly regarded medicinal plant with a num-
ber of medicinal properties in the countries like China and Vietnam
(Figure 1), and it is a commonly used spice. Several biologically impor-
tant phytochemicals have been reported from SA. It also possesses
antimicrobial, antiviral, and antioxidant properties (George, 2012).
Jayanta Kumar Patra and Gitishree Das are combined first author.
Received: 14 October 2019 Revised: 25 December 2019 Accepted: 1 January 2020
DOI: 10.1002/ptr.6614
Phytotherapy Research. 2020;120. © 2020 John Wiley & Sons, Ltd. 1
Apart from the Chinese uses, the fruits are also referred in ayurveda,
traditional Indian system of medicine, as useful in dyspepsia, flatu-
lence, spasmodic colonalgia, dysentery, cough, asthma, rheumarthritis,
facial paralysis, and so forth. Additionally, the essential oils from SA
are composed of prenylated C
compounds, lignans, sesquiter-
penes, and flavonoids, each with different types of compounds which
are also important with respect to its vast medicinal properties.
Among all of them, the anethole compounds are responsible for its
characteristic taste. Besides, compounds like α-pinene, β-pinene,
myrcene, α-phellandrene limonene, γ-terpineol, linalool, α-terpineol,
estragole, trans-anethole, α-cubebene carryophyllene oxide, and
α-humulene present in the essential oil of SA are also reported to
have contained a number of biological activities (Aly, Sabry,
Shaheen, & Hathout, 2016; Luís et al., 2019; Wang, Hu, Huang, & Qin,
2011). In addition, a number of procedures have been established for
the extraction of the bioactive compounds from this plant species,
and, among which, the hydro-distillation, steam distillation, solvent
extraction, supercritical fluid CO
extraction, hydro-distillation-
headspace solvent microextraction, and microwave-assisted extrac-
tion process are the most common ones (Rocha & Candido Tietbohl,
2016). SA has attracted the scientific community due to the presence
of a specific compound called the shikimic acid that acts as a chemical
precursor in the manufactor of oseltamivir (Tamiflu
), an avian flu
drug (Ohira, Torii, Aida, Watanabe, & Smith Jr, 2009; Xu et al., 2017).
The aim of this review is to present the general characteristics, chemi-
cal properties, and antiviral properties of I.verum (SA) along with a
future perspective on its usage.
SA is the ripe, dried fruit of I.verum. Its whorl is formed by six to eight,
one-seeded, boat-shaped, woody, wrinkled, ridged, reddish-brown fol-
licles whose inner structure is characterized by a smooth, lustrous,
and light-brown texture (Zhang, Ji, & Yu, 2018). Its seed is light brown
and ovoid in shape. SA has been used for long in Chinese cuisine as a
spice, but it is not only limited to China but also to Vietnam and India
for the preparation of broths and meat. SA is part of the popular five-
spice powder mix. It contains SA, cassia, clove, fennel, and Sichuan
pepper in equal parts. Besides, it has been a part of the alcoholic bev-
erages such as pastis and absinthes, together with its uses in teas, fruit
compotes, and jams in the Western countries. The inclusion of anise
as a part of a healthy diet could have benefits as in the prevention of
disease in combination with other food types, for example, other
plants, fruits, and vegetables.
The I.verum, which belongs to the division Magnoliophyta, class Mag-
noliopsida, order Austrobaileyales, and family Illiciaceae, is a modest
semblance herb of around 8 to 15 m in height and 30 cm thick with
flat-out, felicitous trunks and emphatic, bald-headed branchlets
(Chouksey, Sharma, & Pawar, 2010). The normal existence of the herb
is 80100 years. The bark is white to bright gray. Its 612 cm tall
leaves are simple, leathery, alternate, plenary, bright, bald-headed,
generally packed in groups toward the finish of the branches
(Chouksey et al., 2010). The flowers bloom huge and are androgynous,
11.5 cm in diameter, white-pink to red or greenish-yellow, axillary,
and single (Chouksey et al., 2010). The fruit looks like capsule, but the
entirety is star formed, radiating 5 to 10-pointed pontoon-molded
segments about eight on average. Every arm of the fruit looks like a
seed pod. The fruits have thick skin and are rust shaded with their
dimension up to 3 cm long (Chouksey et al., 2010). The fruits were
picked since it gets ripen when the essential oil is at its maximum. The
seeds are sparkling brown or ruddy with high oil content (Chouksey
et al., 2010; Fritz, Ölzant, & Länger, 2008; Prajapati, Purohit,
Sharma, & T, K., 2006). In the ayurvedic system of medicine, it is com-
monly used in the rasa: katu, Guna: Lakhu, Teekshna, Virya: Ushra,
Vipaka: Katu (Chouksey et al., 2010).
Fruits comprise a greater number of alkaloids, essential oil, and tannins
(9% to 10%), containing both cis- and trans-anethole (85% to 90%),
limone, α-pinene, safrol, β-phellandrene, α-terpineol, and farnesol
(Chouksey et al., 2010; Dzamic et al., 2009; Tuan & Ilangantileket,
1997). Some little number of nitrogenous components and 14 hydrocar-
bon components along with 22 oxygenated hydrocarbon derivatives are
there like ρ-allylanisole, anisylacetone, anisaldehyde, ρ-cumicaldehyde,
ρ-allylpen, palmitic acid, linoleic acid (14 methoxyphenyl)-prop-2-one
FIGURE 1 Medicinal potential of star anise
TABLE 1 Chemical constituents of star anise
Chemical constituents Structure Applications References
Cis-anethole Antimicrobial, antifungal, anthelmintic,
antioxidant, antinociceptive, gastroprotective,
anti-inflammatory, sedative activity and
insecticidal activities, spasmolytic effect on
contracted smooth muscles, secretolytic and
expectorant effects, estrogenic effects, and
reproductive toxicity
(Chouksey et al., 2010; Marinov & Valcheva-
Kuzmanova, 2015)
α-Pinene Gastroprotective effect, selective anti-
inflammatory and anticatabolic effects,
antinociceptive, antimicrobial activities
(Chouksey et al., 2010; de Almeida Pinheiro et al.,
2015; Him, Ozbek, Turel, & Oner, 2008; Rufino
et al., 2014; Silva et al., 2012)
α-Phellandrene Antimicrobial activity, anti-inflammatory action,
mast cell stabilization, antinociceptive effect,
antifungal activities
(Chouksey et al., 2010; _
Is¸can et al., 2012; Lima
et al., 2012; Siqueira et al., 2016; J.-h. Zhang,
Sun, Chen, Zeng, & Wang, 2017)
Limonene Botanical insecticide, spasmolytic, antitumor,
anticancer, and anti-inflammatory activities.
(Andrade & de Sousa, 2013; Chouksey et al.,
2010; de Sousa, Mesquita, de Araújo Ribeiro, &
de Lima, 2015)
ρ-Cymene Anxiolytic, antioxidant, anticancer,
antinociceptive, anti-inflammatory, and
antimicrobial effects
(Chouksey et al., 2010; Marchese et al., 2017)
Linalool Local anesthetic activity, antimicrobial activity,
anti-inflammatory, antinociceptive,
antihyperalgesic activities
(Chouksey et al., 2010; Peana, Moretti,
Watson, & Preedy, 2008)
TABLE 1 (Continued)
Chemical constituents Structure Applications References
Terpinen-4-ol Antimicrobial effect, anti-inflammatory, and
antioxidant acitivities
(Chouksey et al., 2010; Mondello, De Bernardis,
Girolamo, Cassone, & Salvatore, 2006)
α-Terpineol Antioxidant, antiulcer, anticancer,
antihypertensive, antinociceptive.;
anticonvulsant activities
(Chouksey et al., 2010; Khaleel, Tabanca, &
Buchbauer, 2018)
Shikimic acid Antioxidant, anticoagulant, antithrombotic,
antibacterial, anti-inflammatory and analgesic
(Chouksey et al., 2010; Estevez, & A., & J Estevez,
R., 2012)
Estragole/methyl chavicol/ρ-allylanisole CNS depressant, antioxidant activity,
antimicrobial, anesthetic, and modulation of
the immune responses.
(Chouksey et al., 2010; Wiirzler, Silva-Filho,
Aguiar, Cavalcante, & Cuman, 2016)
Anisyl acetone Antioxidant and antibacterial activities. (Chouksey et al., 2010; Yang et al., 2012)
ρ-Anisaldehyde Antifungal effect, antibacterial, anti-HIV,
anticancer, antineoplastic, anti-inflammatory,
tuberclostatic, antimalarial activities
(Chouksey et al., 2010; Mbah et al., 2017)
β-Caryophyllene Anticancer, anti-inflammatory, anticarcinogenic,
antimicrobial, antioxidative and analgesic
(Chouksey et al., 2010; Fidyt, Fiedorowicz,
Strządała, & Szumny, 2016)
Foeniculin Insecticides (Chouksey et al., 2010; Garneau et al., 2000)
TABLE 1 (Continued)
Chemical constituents Structure Applications References
Linoleic acid Antibacterial activity, anti-inflammatory, acne
reductive, skin-lightening and moisture
retentive property, cardiovascular-protective,
anticancer, neuro-protective, anti-osteoporotic,
and antioxidative effects
(Chouksey et al., 2010; Dilika, Bremner, & Meyer,
2000; Kim, Nam, Kim, Hayes, & Lee, 2014)
Palmitic acid Anti-inflammatory activity, antioxidant,
hypocholesterolemic, nematicide, pesticide,
antiandrogenic flavor, haemolytic, 5-alpha
reductase inhibitor
(Aparna et al., 2012; Chouksey et al., 2010;
Kumar, Kumaravel, & Lalitha, 2010)
Hexadecanoic acid methyl ester Antioxidant, hypocholesterolemic, nematicide,
pesticide, antiandrogenic, haemolytic activities.
(Balamurugan, Evanjaline, Parthipan, & Mohan,
2017; Chouksey et al., 2010)
δ-3-Carene Anti-inflammatory, antihistamine, antifungal
activity, antibacterial, sedative and expectorant
(Ocete, Risco, Zarzuelo, & Jimenez, 1989; Singh,
Maurya, DeLampasona, & Catalan, 2006)
α-Terpinene Antioxidant (Rudbäck et al., 2012; Singh et al., 2006)
1,8-cineole / eucalyptol Antinociceptive property, vasodilator,
bronchodilator, anti-inflammatory activity,
hepatoprotective, gastroprotective,
antibacterial, antimycotic and antitumorogenic
(Bhowal & Gopal, 2015; Singh et al., 2006)
γ-Terpinene Antimicrobial, cytotoxic, anti-inflammatory
(Singh et al., 2006; Soukoulis & Hirsch, 2004)
Trans-linalool oxide Antioxidant and antimicrobial activity (Luís, Duarte, Pereira, & Domingues, 2017; Singh
et al., 2006)
Terpinolene Anticancer, antibacterial, antioxidant,
antifungal and sedative properties
(Aydin, Türkez, & Tas¸demir, 2013; Eftekhar,
Yousefzadi, Azizian, Sonboli, & Salehi, 2005;
Grassmann, Hippeli, Spitzenberger, & Elstner,
2005; Ito & Ito, 2011; Singh et al., 2006)
TABLE 1 (Continued)
Chemical constituents Structure Applications References
Terpinen-1-ol Antibacterial, antifungal, antitumor, cytotoxic,
anticancer activities
(Shapira, Pleban, Kazanov, Tirosh, & Arber, 2016;
Singh et al., 2006)
Borneol Analgesic, anesthetic, sedative, anxiolytic
(Granger, Campbell, & Johnston, 2005; Singh
et al., 2006)
α-Copaene Antimicrobial activity, anti-proliferative,
antioxidant, anti-genotoxic and cytotoxic
(Martins et al., 2015; Singh et al., 2006; Turkez,
Togar, Tatar, Geyıkoglu, & Hacımuftuoglu,
Trans-α-Bergamotene Cytotoxic activity (Monajemi, Oryan, Haeri-Roohani, Ghannadi, &
Jafarian, 2010; Singh et al., 2006)
Δ-Cadinene Anticancer activity (Hui, Zhao, & Zhao, 2015; Singh et al., 2006)
1,4-cineole Fumigant insecticide and CNS depressant (Singh et al., 2006)
γ-Terpineol Flavoring ingredient
β-Terpineol Flavoring ingredient
TABLE 1 (Continued)
Chemical constituents Structure Applications References
Acetaldehyde In the production of sedatives and tranquilizers,
flavoring agents
Methyl p-anisate Flavoring agent
Trans-β-Farnesene Scent preparation.
4-Methoxypropiophenone Fragrance agent
m-Methoxy mandelic acid Not reported
t-Muurolol Antifungal activity
Margaric acid Antiproliferative activity
Phenol Oral analgesic, antiviral, antifungal activities (Wei et al., 2014)
Benzoic acid Antifungal activity
4-Ethyl benzaldehyde Flavoring ingredient
TABLE 1 (Continued)
Chemical constituents Structure Applications References
Benzyl alcohol Local anesthetic, antimicrobial, insect repellent,
flavoring agents.
4-Methoxy benzoic acid / p-anisic acid Antimicrobial activity
4-Methoxy benzaldehyde oxime Not reported
O-Nitrobenzoic acid Not reported
β-Copaene Antimicrobial activity (Sinha, 2019; Wei et al., 2014)
Longifolene Antifungal, anti-termite activities, flavoring agent,
natural autoxidation
(Mukai, Takahashi, & Ashitani, 2017, Mukai,
Takahashi, & Ashitani, 2018, Wei et al., 2014)
Bisabolene Anticonvulsant activity, flavoring agent (Orellana-Paucar et al., 2012; Wei et al., 2014)
ρ-Hydroxybenzoic acid Antiestrogenic, antimutagenic, antimicrobial,
antialgal, anti-platelet aggregating, antioxidant.
Nematicidal, hypoglycemic, anti-inflammatory,
antiviral activities
(Manuja, Sachdeva, Jain, & Chaudhary, 2013; Wei
et al., 2014)
β-Humulene Anti-inflammatory, antibiotic, antioxidant,
anticarcinogenic and local anesthetic activities
(Legault & Pichette, 2007; Wei et al., 2014)
TABLE 1 (Continued)
Chemical constituents Structure Applications References
3-Hydroxybenzoic acid Anti-stress, anxiolytic and antidepressant,
antimicrobial agents
(Khan, Chatterjee, & Kumar, 2015; Kumar et al.,
2010; Wei et al., 2014)
3,6-Dimethyl-4H-furo[3,2-C]pyran-4-one Not reported (Wei et al., 2014)
3-Hydroxy-1,2-benzisoxazole Not reported
4-Methoxy cinnamaldehyde Flavoring agent
4-Ethyl-α-methyl benzyl alcohol Not reported
Cis-3,5-dimethoxy-β-methyl-β-nitrostyrene Not reported
Hydrazine carboxylic acid,2-methyl-
3,7-dimethyl-2,6-octadienal ester
Not reported (Yan et al., 2002)
9-Methyl-9H-fluorene Organometallic reagent (Bowen, Aavula, & Mash, 2002;
Wei et al., 2014)
Not reported (Huang et al., 2013)
TABLE 1 (Continued)
Chemical constituents Structure Applications References
2,2-Diisobutyl-1,3-benzodioxole Not reported (Wei et al., 2014)
Bendazol Hypotensive, vasodilator, antispasmodic action,
anti-parasitic activities
Trans-2-Ethoxy-β-methyl- β-nitrostyrene Not reported
N-(4-hydroxyphenyl)-2-methylbenzamide Not reported
9,12-Octadecadienoic acid (Z,Z)-, methyl ester
/ methyl linoleate
Flavoring ingredient
Phenol-3-[2-(2-phenylethyl)amino]ethyl Not reported (Huang et al., 2013; Wei et al., 2014)
Spiro[4.5]dec-1-ene Not reported (Yan et al., 2002)
TABLE 1 (Continued)
Chemical constituents Structure Applications References
α-Farnesene Flavoring ingredient
2-Methyl-3-phenylpropanal Not reported
Phenyl ethanolamine Cardiovascular activity
Surfynol 102 Surfactant
Acetic acid geranyl ester Flavoring ingredient
p-Allylphenol/Chavicol Odorant
Hexyloleate Not reported
2-(2-Aminopropoxy)-3-methyl benzeneethanol Not reported
Bicyclo 2.2.1 heptane-2,3-dione,6-(acetyloxy)-
1,5,5-trimethyl, endo
Not reported
TABLE 1 (Continued)
Chemical constituents Structure Applications References
Acethydrazide Antibiotic, cytotoxic activities
Not reported (Huang et al., 2013)
Not reported
Nopol Flavoring ingredient
γ-Elemene Antitumor (S. Wang et al., 2012; Yan et al., 2002)
3-Undecene Not reported
Germacrene D Antibacterial property, cytotoxicity, olfactory
receptor neuron activator.
(Essien et al., 2016; Yan et al., 2002)
Trans-Nerolidol Flavoring agent, antineoplastic, leishmanicidal,
anti- parasitic, and antifungal activities
(Arruda, D'Alexandri, Katzin, & Uliana, 2005; S.-J.
Lee et al., 2007; Yan et al., 2002)
TABLE 1 (Continued)
Chemical constituents Structure Applications References
Geranyl isobutyrate Flavoring agent
Veranisatin A Analgesic activity (Nakamura, Okuyama, & Yamazaki, 1996)
Veranisatin B Analgesic activity
ρ-Cumic aldehyde Not reported
and foeniculin (Wang, Jiang, & Wen, 2007; Yamada, Takada,
Nakamura, & Hirata, 1965; Yan, J.-h., Xiao, X.-x., & Huang, K.-l., 2002).
The new phenylpropanoid glucosides, such as seco-cycloartane; alkyl
glucosides, 3,4-seco(242)-cycloartane-4(28),24(diene)3,26-dioic acid, and
phenylpropanoid 26- methyl ester of nigranoic acid, were also recog-
nized from dichloromethane leaves extract of I. verum (Lee, Li, Lee,
Song, & Son, 2003; Sy & Brown, 1998).
Another study of phytochemical assessment claims that the
I. verum fruit contains β-pinene, β-sitosterol, a-phellandrene, p-
cymene, β-myrcene, limonene, car-3-ene, cineol, 4(10)-thujene, linal-
ool, and 4-terpineol (Asolkar, Kakkar, & Chakre, 1992; Rashid &
Zuberi, 2016; Rastogi & Mehrotra, 1993). The presence of safrole, as
well as hydroquinone ethyl ether, was also detected. The fatty acid
mix contains myristic, stearic, and linoleic acids (Asolkar et al., 1992;
Rastogi & Mehrotra, 1993). It also contains copaene, anisketone,
sesquicitronellene, caryophyllene, farnesene, methyl-3-methoxy-ben-
zoate, methyl isoeugenol, p-hydroxy benzoic acid, nerolidol, and m-
methoxy-a-benzyl benzene acetic acid (Asolkar et al., 1992; Rashid &
Zuberi, 2016; Rastogi & Mehrotra, 1993). A number of bioactive com-
pounds found in the I.verum are listed in Table 1, many of which are
reported by Chouksey et al. (2010).
4.1 |Isolation of volatile oils
The volatile oils isolated from I.verum by hydro-distillation process
are α-pinene, sabinene, limonene, δ-3-carene, α-phellandrcene,
1,8-cineole, γ-terpinene, p-cymene, linalool, β-caryophyllene,
estragole, α-terpineol, cis-anethole, trans-anethole, anisaldehyde
(Bernard, Perineau, Delmas, & Gaset, 1989), terpinen-4-ol,
α-terpinene (Rudbäck, Bergström, Börje, Nilsson, & Karlberg, 2012),
terpinolene (Amanzadeh, Ashrafi, & Mohammadi, 2006), terpinen-
1-ol, borneol (Chen et al., 2014), α-copaene (Martins et al., 2015),
δ-cadinene (Pérez-López, Cirio, Rivas-Galindo, Aranda, & de Torres,
2011), 4-methoxypropiophenone, β-copaene, bisabolene (Aslam,
Ahmad, & Raja, 2017), O-nitrobenzoic acid, α-farnesene, germacrene
D (Özek et al., 2018), trans-nerolidol (Sriti Eljazi et al., 2018), geranyl
isobutyrate (Wangchuk, Keller, Pyne, Taweechotipatr, &
Kamchonwongpaisan, 2013), chavicol (Charles & Simon, 1990), and
ρ-cumic aldehyde.
4.2 |Isolation of shikimic acid
From ethanolic extract of SA, the solvent was removed by the help of
a rotary flash evaporator under reduced pressure. The residue was
again dissolved in water and heated up to 80C. Five drops of
3740% formaldehyde solution was mixed to the warm solution and
cooled. A glass filter funnel was used to remove the precipitate which
contains a layer of celite to obtain a clear orange solution. Again it is
passed through an anion exchanger (Amberlite IRA-400) to collect the
yellow eluent and acetic acid. Then, the acetic acid was eliminated by
high vacuum rotary evaporator that afforded an orange-colored solid.
It was then dispersed in methanol and heated. To afford a solid mass,
filtration and subsequent elimination of the methanol was continued.
In the next step, the solid mass was recrystallized to get a bright white
crystalline solid called shikimic acid (Payne & Edmonds, 2005).
4.3 |Isolation of anisyl acetone
Isolation of anisyl acetone was performed by GC/MS analysis using
helium (He) as carrier gas (Meier, Kohlenberg, & Braun, 2003).
4.4 |Isolation of foeniculin
The isolation of foeniculin is done by using high-performance
counter-current chromatography (HPCCC), notably, high-speed
counter-current chromatography is considered, from essential oils of
SA, whose presence was confirmed by GCMS analysis (Skalicka-
Woźniak, Walasek, Ludwiczuk, & Głowniak, 2013).
4.5 |Isolation of linoleic acid
The isolation of linoleic acid is done by treating the extract of the mixed
acids with sufficient urea to reduce the content of saturated and oleic
acids in the initial liquids to about 5%; then go for low-temperature crys-
tallization from acetone at 75C then gives a precipitate enriched in
linoleic acid (Gunstone, McLaughlan, Scrimgeour, & Watson, 1976).
4.6 |Isolation of palmitic acid
Directly, n-hexane is mixed to the crude methanolic extract with vig-
orous stirring; it was then filtered and while the residue was permitted
to dry and the same technique was repeated with ethyl acetate, n-
butanol, and lastly the residue acquired is methanol fraction. Ethyl
acetate, methanol, n-hexane, and n-butanol fractions acquired were
concentrated in hot air sterilizing chamber. Column chromatography
was then performed using petroleum benzene as mobile phase
followed by 9:1 ratio of petroleum benzene and ethyl acetate as elut-
ing solvent. The eluents were reviewed by TLC using methanol and
chloroform at 1:9 ratio. The isolated colorless powder was then ana-
lyzed with UVVis, IR,
H NMR and
C NMR spectroscopies for
appropriate characterization of palmitic acid (Bulama, Dangoggo,
Halilu, Tsaf, & Hassan, 2014).
4.7 |Isolation of hexadecanoic acid methyl ester
Methanolic extract was fractionated using flash column chromatography
using mixtures of hexane and ethyl acetate. Oil was acquired with hexane
inethylacetate.GCMS and spectroscopic analyses confirm the hex-
adecanoic acid methyl ester presence (Ajoku, Okwute, & Okogun, 2015).
4.8 |Isolation of methyl linoleate
It was extracted with n-hexane, then quantified by HPTLC and applied
directly to flash chromatography using hexane:acetone (40:60) in
order to isolate methyl linoleate as pale-yellow viscous oil (Jubie,
Dhanabal, & Chaitanya, 2015).
SA is rich in flavonoids, alkaloids, tri-terpenoids, saponins, tannins, and
anthraquinones along with a repository of reducing sugars, amino
acids, and proteins. Several biologically important phytochemicals
reported from SA have shown to have antiviral effects and were stud-
ied against several viral pathogens. Shikimic acid (3,4,5-trihydroxy-
1-cyclohexene-1-carboxylic acid), a natural organic compound and an
important intermediate in the biosynthesis of various phytochemicals,
is one of the most widely studied molecules from SA in the context of
its antiviral effects. It is the key intermediate of the shikimic acid path-
way and has gained relevance as a substrate for the chemical synthe-
sis of the drug oseltamivir phosphate (OSP), known commercially as
Tamiflu (Candeias, Assoah, & Simeonov, 2018). This drug is an
efficient inhibitor of the surface protein neuraminidase (NA) enzyme
of the seasonal influenza virus types A and B, avian influenza virus
H5N1, and human influenza virus H1N1 (Bradley, 2005). Although SA
pods were one of the main sources of shikimic acid, the yield was only
up to 17% (dry basis content) and was not sufficient to meet the high
demand for the OSP drug to manage the major influenza outbreaks.
As an alternate, advancements in biotechnology had helped in design-
ing innovative strategies of synthesizing shikimic acid using genetically
modified Escherichia coli (Bilal et al., 2018; Martínez, Bolívar, &
Escalante, 2015).
While shikimic acid is the most important bioactive from SA, stud-
ies have reported several other molecules as well with prominent ant-
iviral effects. In a study wherein two new compounds, illiverin A and
tashironin A, reported from the roots of I.verum along with seven
other known compounds, namely, 4-allyl-2-(3-methylbut-2-enyl)-1,-
6-methylenedioxybenzene-3-ol; illicinole, 3-hydroxy-4,5-methylenedi-
oxyallyl-benzene; ()-illicinone-A; 4-allyl-4-(3-methylbut-2-enyl)-
1,2-methylenedioxycyclohexa-2,6-dien-5-one; 3,4-seco-(24 Z)-cycloart-4
(28),24-diene-3,26-dioic acid; and 26-methyl ester and tashironin, showed
that compounds ()-illicinone-A and 26-methyl ester possessed moderate
anti-HIV activity with EC50 values of 16.0 and 5.1 μM, respectively (Song
et al., 2007). Similarly, studies carried out with essential oils from SA also
showed interesting results with respect to its antiviral effects. Studies
TABLE 2 Various compounds reported from other species from the genus Illicium with antiviral effects
number Species Compound Activity against References
Hepatitis B (J. Liu et al., 2016)
2 2S-hydroxyl-jiadifenolide, jiadifenlactone acid,
Jiadifenolide, 2-oxo-3,4-dehydroxyneomajucin,
2-oxoneomajucin, neomajucin, majucin, (2S)-
hydroxyneomajucin, (2R)-2-hydroxyneomajucin
and (1R,2S)-1,2-epoxyneomajucin
Expression of HBeAg
and HBsAg
(J.-F. Liu et al.,
spirooliganone B
Coxsackie virus B3 (CVB3)
Coxsackie virus B3 and influenza virus
A (H3N2)
(Lü et al., 2015;
Ma et al., 2013)
4Illicium henryi 10-Benzoyl-cycloparvifloralone HBV surface antigen
(HBsAg) secretion and
HBVe antigen (HBeAg) secretion
(Ji-Feng et al.,
5 Sesquiterpene lactones, henrylactones AE(15),
together with ten known compounds:
Cycloparvifloralone (6), tashironin (7), tashironin
A (8), neoanisatin (9), anisatin (10), anislactone B
(11), 7-O-acetylanislactone B (12), merrillianolide
(13), cyclomerrillianolide (14) and pseudomajucin
Anti-hepatitis B virus (HBV) (J.-F. Liu et al.,
6()-Dihydrodehydrodiconiferyl alcohol tashironin Both HBsAg and HBeAg
HBV surface antigen
(HBsAg) secretion
(J.-F. Liu et al.,
J. F. Liu et al.,
7Illicium majus Majusanic acids E
Majusanic acids F
4-Epi-dehydroabietic acid
Majusanic acids B
Majusanic acid D
Coxsackie B3 virus (Y.-D. Wang et al.,
carried out with the anise oil along with two other essential oils (dwarf-pine
oil and chamomile oil) against different types of thymidine-kinase such as
thymidine-kinase-positive (aciclovir-sensitive) and thymidine-kinase-
negative (aciclovir-resistant) herpes simplex virus Type 1 (HSV-1) showed
that all these essential oils have antiviral activity against the aciclovir-
sensitive HSV strain KOS and aciclovir-resistant clinical HSV isolates as
well as aciclovir-resistant strain Angelotti, through interrupting the adsorp-
tion of herpes viruses. This is different from the mode of action of aciclovir,
which is effective after attachment inside the infected cells. The report
indicated that these oils are capable of exerting a direct effect on HSV and
might be useful in the treatment of drug-resistant viruses (Christine Koch
et al., 2008). Astani, Reichling, and Schnitzler (2011) evaluated the antiviral
activity of SA essential oil against HSV-1 under in vitro condition. Likewise,
another study of anise essential oils on herpes simplex virus Type 2 (HSV-
2), carried out on RC-37 cells using a plaque reduction assay, showed an
inhibition with IC
value of 0.016% (Koch, Reichling, Schneele, &
Schnitzler, 2008). Compounds like anethole, 4-methoxy-benzaldehyde,
2-hydroxy-2-(4-methoxy-phenyl)-n-methyl-acetamide, cyclohexyl-ben-
zene, 1-(1-methylethenyl)-3-(1-methylethyl)-benzene, eucalyptol, γ-sitos-
terol, and so forth were also reported from SA with various bioactivities
(Peng et al., 2016). Similarly, there are various other compounds which
have been reported from other species from the genus Illicium which have
potential antiviral effect (Table 2). Ma et al. (2013) have reported isolation
of two novel antiviral compounds spirooliganones A and B, from the roots
of Illicium oligandrum. And among the two, the spirooliganone B was
highly effective against the coxsackie virus B3 and influenza virus A
(H3N2) with IC
values of 3.705.05 μM than the spirooliganone A com-
pound by a biosynthetic pathway which includes a hetero-DielsAlder
reaction process of the epimers (Ma et al., 2013). Similarly Lü et al. (2015)
has also isolated the oligandrin and oligandric acid from the roots of
I. oligandrum and tested its promising antiviral activity against the
coxsackie virus B3 (CVB3), influenza virus A/Hanfang/359/95 (H3N2),
and influenza virus A/FM/1/47 (H1N1) (Lü et al., 2015). Liu et al. (2010)
have isolated five new sesquiterpene lactones, henrylactones AE
along with 10 other known compounds from the stems and roots of
Illicium henryi and tested them for their antihepatitis B virus (HBV)
activities. Among them, tashironin compound exhibited significantly
high activity inhibiting the HBV surface antigen (HBsAg) secretion
and HBV e antigen (HBeAg) secretion using HBV transfected Hep
G2.2.15 cell line (J.-F. Liu et al., 2010). Liu et al. (2016), isolated two
compounds from the fruits of Illicium jiadifengpi,namely,
3,4-dehydroneomajucin and 1,2,3,4-tetradehydroneomajucin, with
potent antihepatitis B virus activities on the Hep G2.2.15 cell line.
Wang et al. (2013) have isolated around 13 compounds from the
roots of Illicium majus and have tested their antiviral potential against
the Coxsackie B3 virus.
A number of pre-clinical and clinical studies have been undertaken
to develop the antiviral drug using the shikimic acid isolated from
the Illicium anisatum, or SA (Bradley, 2005). These drugs have been
approved and commercialized in the name of Tamiflu (Bradley,
2005). The mixture of shikimic acid and quercetin has been reported
to be tested against the bird flu in China and Taiwan (Boota,
Rehman, Mushtaq, & Kazerooni, 2018). Besides, there are reports
that the essential oil from the SA and its isolated compounds
exhibited promising antiviral activity against the HSV-1 in the viral
suspension tests (Astani et al., 2011). There are more studies which
have been devoted to the development of drugs against herpes
(7401H HSV1; Allahverdiyev et al., 2013), along with products such
as vaginal gels to fight Candida species, although more significant
studies need to be achieved in order to step into the clinical trial
phases (Gafit¸{t\hskip-0.7ex\char "B8}anu et al., 2016) for these
pharmaceutical formulations. Apart from these, a number of com-
pounds have been isolated from different species of the genus
Illicium and have been tested against different types of viruses
which is summarized in Table 2.
SA (I.verum) is one of the important plant species which is a reposi-
tory of various types of bioactive molecules. Besides using it as a culi-
nary ingredient, various traditional medicines have reported about the
diverse applications of this plant in managing numerous disease condi-
tions. Nevertheless, the plant is most often commended for its ant-
iviral effects because of the oseltamivir (Tamiflu), which has been
commercially available as a treatment for flu. Besides, it would also be
more impactful to study the immunomodulatory and other virus resis-
tance mechanism that the body exerts against a number of viruses.
Such studies are important because the resistance to viral infections
need not be always through a direct inhibition of virus, but it can also
be through enhancing the body's resistance to the infections. In the
future research work, it is necessary to identify more active com-
pounds and their derivatives from this plant species for their potential
clinical trials for the evaluation of the applicable thwack of I. verum
against numerous human diseases. In this review, the antiviral effects
of SA have been indicated together with the botanical description,
number of phytoconstituents present, and isolation procedure of the
Authors are grateful to their respective institutions for support.
Authors declare no conflict of interest with the manuscript.
Jayanta Kumar Patra
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How to cite this article: Patra JK, Das G, Bose S, et al. Star
anise (Illicium verum): Chemical compounds, antiviral
properties, and clinical relevance. Phytotherapy Research.
... Drug repurposing is a powerful strategy in which the already FDA-approved drugs on the market are repurposed for different clinical indications than prescribed. It is performed by pharmacophore modelling combined with virtual screening to retrieve new molecules from the FDA drug database [24][25][26][27][28][29][30]. This approach can also help pharmaceutical companies reduce the time and resources required to develop new chemical entities. ...
... No specific antiviral medication has been proven to treat COVID-19, although several trials are ongoing worldwide. Many such drugs have been tested, and a few are currently being used as prophylactic drugs for SARS-CoV-2 (Table 1, Ref. [23][24][25][26][27][28][29]). ...
... Table 2 lists the various phytocompounds that have been studied against COVID-19. In-vitro studies using SARS-CoV2 infected Vero cells has approved the usage of western medicines such as hydroxychloroquine obtained from cinchona bark at a concentration of EC 50 = 0.72 µM [25] and oseltamivir containing shikimic acid derived from the spice star anise [29] to treat COVID-19. Two alkaloid derivatives namely Emetine and homoharringtonine at a concentration (EC 50 ) of 2.55 µM and 0.46 µM showed significant viral replication inhibition activity in Vero E6 cells. ...
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COVID-19, caused by the severe acquired respiratory syndrome coronavirus-2 (SARS-CoV-2), is a highly contagious disease that has emerged as a pandemic. Researchers and the medical fraternity are working towards the identification of anti-viral drug candidates. Meanwhile, several alternative treatment approaches are being explored to manage the disease effectively. Various phyto-drugs and essential oils have been reported to have antiviral activity, but this has not been well studied in the context of SARS-CoV-2. The main focus of this review is on the biology of infection and the different therapeutic strategies involved, including drug repurposing and phytopharmaceuticals. The role of phytochemicals in treating COVID-19 and various other diseases has also been emphasized.
... Spices and herbs are edible parts of the plants that are very aromatic and flavorful. Although spices and herbs are primarily used as food seasonings, increasing evidence shows their potentials in prevention and treatments of many diseases, especially cancer and the devastating SARS-Cov-2 (COVID-19) infection (Bhagat & Chaturvedi, 2016;Patra et al., 2020;Singh, Kumar, & Jyoti, & Kumar, N., 2021). While extraction can be achieved quite simply for herbs (e.g., leaves, flowers) because of their softness, spice seeds and dry fruits are extremely challenging due to their naturally hard structures. ...
... Despite various difficulties in the extraction of SA which have extremely hard-to-crush and woody structure, bioactive compounds from SA have been shown to be invaluable for pharmaceutical applications, especially antiviral and anticancer medicines (Patra et al., 2020). Hence, there is an urgent need for an effective extraction method that can easily and quickly tackle the hard structure of SA. ...
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Extraction of plant materials is an essential practice in various fields using natural compounds. Nevertheless, it is challenging to perform complicated extraction efficiently and consistently on materials with hard-to-crush structures. This work presents a new method called simultaneous stone-milling and extraction (SME) to achieve one-step extraction of hard materials. SME under its optimal conditions was confirmed to produce high quality extracts from whole spice seeds (anise seeds, dill seeds, fennel seeds) and coarse-cut star anise. Compared to other extraction methods like maceration, heat-assisted extraction and ultrasound-assisted extraction, SME extracts contained comparable or higher concentrations of general (polyphenols, flavonoids, antioxidants) and specific (enzyme inhibitors) bioactive groups. Hence, SME with its one-step operation is expected to simplify the task of plant extraction and contribute to the advances in studies using plant-derived phytochemicals.
... In the pharmaceutical field, the essential oils are generally regarded as safe and have been approved by the FDA for their use in the management of flatulence, muscle spasm, and colic, however common adulterants like Japanese star anise fruits (Illicium anisatum) are not edible due to reported neurotoxicity 3 . Star anise has likewise been reported to display strong antiviral activity 4 . It is also an industrial source of shikimic acid, the precursor of the antiavian flu (H5N1 strain) medication oseltamivir (Tamiflu V R ) 4 . ...
... Star anise has likewise been reported to display strong antiviral activity 4 . It is also an industrial source of shikimic acid, the precursor of the antiavian flu (H5N1 strain) medication oseltamivir (Tamiflu V R ) 4 . For that reason, metabolite profiling of star anise can be of great importance in its identification and quality control analysis. ...
... Spirooliganone, uncinoside, baicalein and curcumin are natural products with antiviral effects 38 . Specifically, Tamiflu, a treatment for influenza A and B, is based on a natural product derived from the Chinese spice, star anise (Illicium verum) 39 . Thus, the use of natural products as a starting point for new drug discovery will be a viable strategy for the successful development of therapeutics that can effectively control COVID- 19. ...
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The pandemic caused by severe acute respiratory Coronavirus-2 (SARS-CoV-2) has been ongoing for over two years, and treatment for COVID-19, other than monoclonal antibodies, is urgently required. Accordingly, we have investigated the inhibitors of SARS-CoV-2 protein targets by high-throughput virtual screening using a marine natural products database. Considering the calculated molecular properties and availability of the compounds, (+)-usnic acid was selected as a suitable hit. In the in vitro antiviral assay of (+)-usnic acid by the immunofluorescence method, IC50 was 7.99 μM, which is similar to that of remdesivir used as a positive control. The generalized Born and surface area continuum solvation (MM/GBSA) method was performed to find the potent target of (+)-usnic acid, and the Mpro protein showed the most prominent value, −52.05 kcal/mol, among other SARS-CoV-2 protein targets. Thereafter, RMSD and protein–ligand interactions were profiled using molecular dynamics (MD) simulations. Sodium usnate (NaU) improved in vitro assay results with an IC50 of 5.33 μM and a selectivity index (SI) of 9.38. Additionally, when (+)-usnic acid was assayed against SARS-CoV-2 variants, it showed enhanced efficacy toward beta variants with an IC50 of 2.92 μM and SI of 11.1. We report the in vitro anti-SARS-CoV-2 efficacy of (+)-usnic acid in this study and propose that it has the potential to be developed as a COVID-19 treatment if its in vivo efficacy has been confirmed.
... Additional bioactive compounds which are found in ASF essential oils are myrcene, limone, linalool, luteolin, estragole, caryophyllene, c-terpineol, and α-humulene [72]. Moreover, recent studies have reported the presence of other compounds such as β-sitosterol, α-phellandrene, β-myrcene, mairin, honokiol, cineol, and safrole [73][74][75]. ...
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Anisi stellati fructus (ASF) is the fruit of Illicium verum Hook F. (Chinese star anise), which is native to many countries, and is a significant Chinese medicinal herb. Gastric cancer (GC) is one of the major fatal types of cancers with multiple stages and a poor prognosis. The present review aims to discuss the bioactive properties of ASF and its phytocompounds against GC, with a particular insight into the molecular mechanisms and signaling pathways involved in its anti-GC mechanism. Furthermore, it highlights the potential mechanism of action of major phytocompounds of ASF against GC. Clinical studies (in vitro and in vivo) regarding the action of ASF and its major bioactive compounds such as quercetin, luteolin, kaempferol, d-limonene, and honokiol against GC were reviewed. For this review, search of literature was performed in Science, PubMed, Google Scholar, Web of Science, and Scopus related to ASF and its phytocompounds, from which only relevant studies were chosen. Major bioactive compounds of ASF and their extracts have proven to be effective against GC due to the mechanistic action of these compounds involving signaling pathways that target cancer cell apoptosis, proliferation, and tumor metastasis in GC cells. Existing reports of these compounds and their combinatory effects with other modern anticancer agents have also been reviewed. From its traditional use to its role as an anticancer agent, ASF and its bioactive phytocompounds have been observed to be effective in modern research, specifically against GC. However, further studies are required for the identification of molecular targets and pharmacokinetic potential and for the formulation of anti-GC drugs.
... Star anise (Illicium verum Hook.f.) is an aromatic evergreen tree native to western China, Vietnam, Cambodia, Myanmar, Indonesia, the Philippines and other subtropical regions. Its fruits are not only an important Chinese medicine, treating vomiting, stomachache, insomnia, skin inflammation and rheumatism [3,4], but also a common spice in cooking [5], being introduced into Europe in the 17th century. Its unique licorice flavors are the result of a compound called anisole [4,6]. ...
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Recently, the effects of weed control on crop yield, quality and soil fertility have been increasingly investigated. However, soil microorganism diversity under weed control, especially for aromatic plants, is little studied. Mechanical weeding effects on soil fertility and microbial diversity in star anise plantations remain unknown, limiting improvements in crop quality and yield through weed control. Therefore, mechanical weeding (MW) and no weeding (NW) zones were randomly designed in the same star anise plantation to study the mechanical weeding impacts on soil biological properties and microbial diversity. The phosphatase activity of MW soil was significantly higher than that of NW soil; however, aminopeptidase activity was significantly lower than that under NW. There was no significant difference in β -glucosidase activity between MW and NW. Moreover, soil microbial biomass C and N in MW soil were significantly higher than those of NW, but soil microbial biomass P was significantly lower than that of NW. Proteobacteria, Acidobacteria, Actinobacteria, Chloroflexi, Planctomycetes, WPS-2, Firmicutes and Verrucomicrobia were the predominant bacterial phyla in MW and NW soils. Specifically, Bacteroidetes was enriched in MW soil, being the unique dominant bacteria. Ascomycota, Basidiomycota, unclassified_k_Fungi, Rozellomycota and Mortierellomycota were the predominant fungi in MW and NW soils. The numbers of dominant bacterial genera (> 1%) were 26 and 23 for NW and MW soils, respectively. Among them, norank_f__norank_o__norank_c__Subgroup_ 6, 1921–2 and norank_f__norank_o__B 12 -WMSP 1 went undetected in MW soil. Moreover, the numbers of dominant fungi in soils of star anise plantations were 11 and 9 for NW and MW, respectively. Among them, only unclassified_f__Clavicipitaceae and Mortierella went undetected in MW soils. Thus, soil microbial community structures are not significantly altered by mechanical weeding. The above results suggest that soil fertility can be improved and soil heath can be maintained by mechanical weeding in star anise plantations. Moreover, soil-borne diseases maybe easily occurred under NW treatment in star anise plantation.
... The three major compounds of the Hex fraction were found to be trans-anethole (69.43%), p-anisaldehyde (5.73%), and phenol (2.18%). The trans-anethole was assumed to be the single key component showing strong insect-repelling activity in SA Hex fraction, inconstancy with the previous reports that trans-anethole was the main active compound in the extract or essential oil of SA (Patra et al., 2020;Singh et al., 2006). The differences in the composition of major compounds were potentially due to the differences in extraction methods and associated conditions including solvent type and extraction temperature (Sadeh et al., 2019). ...
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One of the major stored product pests, Indian meal moth causes the loss on the agriculture and food industries. This study was conducted to screen the insecticidal activity of ethanolic extracts and fractions partitioned by four different solvents [(1) n-hexane; (2) ether; (3) ethyl acetate; (4) water] from star anise (Illicium verum Hook. f.) against Plodia interpunctella larvae. Among all solvent-partitioned fractions, the strongest repellency was found for the n-hexane fraction of star anise extract. Solvent-solvent partitioning and chromatographic methods were further used to isolate and identify major anti-insect compounds from star anise extract. The results showed that trans-anethole (94.24%) was the major active compound showing an insect-repelling activity against P. interpunctella. Consequently, trans-anethole can be utilized as a main natural insect-repelling agent for controlling the P. interpunctella infestation. Supplementary information: The online version contains supplementary material available at 10.1007/s10068-022-01053-8.
The treatment of chemical and biological contaminants in water through bio‐fabricated metal nanoparticles is one of the promising sustainable methods. Herein, an efficient synthesis of novel chromium oxide nanorods is introduced by Illicium verum fruit extract as a bio‐reducing, capping, and stabilizing agent. The morphological, optical, catalytic, and bactericidal properties of nanorods are investigated by various techniques. The UV–visible spectra displayed strong absorption peak in the region of 309.8 nm, whereas Fourier transform infrared presented the characteristic vibrations at 605.65 and 651.94 cm−1 attributed to CrO binding mode. Scanning electron microscopy results showed that chromium oxide nanoparticles are well‐dispersed with small rod‐shaped morphology. The average size of nanorods was found to be ~15 to 20 nm in length. Due to their ultra‐large surface area and strong π–π interaction, the plant‐coated nanorods were tested for the catalytic removal of methyl orange (MO), a common water‐soluble textile dye. Adsorption potential of Cr2O3 nanoparticles was monitored by UV–visible spectrophotometer, which showed 90–95% successive decrease in the absorption maxima of aqueous MO (1 μM). The elimination rate of MO was drastically improved from 45 to 30 min, while a combination of Cr2O3 nanorods and sodium borohydride NaBH4 was used. Bactericidal activities of these nanorods were tested against vast number of Gram‐positive and Gram‐negative bacteria. The significant results were obtained with 27 mm zone of inhibition against Klebsiella. oxytoca and Serratia. marcescens. This quick and simple procedure can be scaled up for commercial applications of new, eco‐friendly, and cost‐effective water treatment process. In this work, the novel strategy for using Illicium. verum fruit extract to fabricate Cr2O3 nanorods and examining the nanorod activities in methyl orange degradation and antibacterial application is described. The results reveal that the utilization of Cr2O3 nanorods does enhance both kinds of activities. Overall, this manuscript provides a novel idea to synthesize uniform Cr2O3 nanorods.
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Natural ovicidal and repellent agents against Periplaneta americana L. are urgently needed, and plant essential oils (EOs) can assume this role quite readily. In this study, ovicidal and repellent activities against Periplaneta americana of EOs from Cymbopogon citratus (Stapf.), Cinnamomum verum (J. Presl.), Eucalyptus globulus (Labill.), Illicium verum (Hook.f.), and Zanthoxylum limonella (Alston) in soybean oil and in ethyl alcohol were determined by topical and dual-choice assays, as well as 10% cypermethrin and a combined formulation of 5% C. verum EO + 5% I. verum EO. Cypermethrin at 10% provided the highest toxicity (100% inhibition rate) against the eggs, but only slightly higher than that (99.3%) provided by the combined EO formulation, while the highest repellent activity against the adults was provided by the combined formulation (89.5% repelled cockroaches at 48 h after treatment). In addition, all EO formulations in soybean oil provided higher ovicidal and repellent activities than those in ethyl alcohol. To conclude, the combined EO formulation in soybean oil can replace cypermethrin because their efficacy was nearly equivalent, but the combination should be much safer to use.
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Many essential oils (EOs) of different plant species possess interesting antimicrobial effects on buccal microorganisms and cytotoxic properties. EOs of Kielmeyera coriacea Mart. & Zucc. were analyzed by gas chromatography coupled to mass spectrometry (GCMS). The EO from leaves is rich in sesquiterpenes hydrocarbons and oxygenated sesquiterpenes. The three major compounds identified were germacrene-D (24.2%), (E)-caryophyllene (15.5%), and bicyclogermacrene (11.6%). The inner bark EO is composed mainly of sesquiterpenes hydrocarbons and the major components are alpha-copaene (14.9%) and alpha-(E)-bergamotene (13.0%). The outer bark EO is composed mainly of oxygenated sesquiterpenes and long-chain alkanes, and the major components are alphaeudesmol (4.2%) and nonacosane (5.8%). The wood EO is mainly composed of long-chain alkanes and fatty acids, and the major components are nonacosane (9.7%) and palmitic acid (16.2%).The inner bark EO showed the strongest antimicrobial activity against the anaerobic bacteria Prevotella nigrescens (minimum inhibitory concentration-MIC of 50 𝜇g mL−1). The outer bark and wood EOs showed MICs of 100 𝜇g mL−1 for all aerobic microorganisms tested. The EOs presented low toxicity to Vero cells. These results suggest that K. coriacea, a Brazilian plant, provide initial evidence of a new and alternative source of substances with medicinal interest.
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The Illicium verum (star anise) has long been used in traditional medicine and food industry with the actions of preventing cold, and relieving pain. Sometimes, it gets contaminated with highly poisonous Japanese star anise (Illicium anisatum L.) which contains toxic sesquiterpenes. Traditional uses of Illicium verum are evidenced from south and west Asia, where it has been consumed for a number of disorders. Several bioactive constituents such as sesquiterpenes, phenylpropanoids, lignans, flavonoids and other compounds have been recognized from Illecium verum. The pharmacology studies demonstrated that its active compounds possess broad range of pharmacological uses, especially in cytotoxic, antioxidant, anti-inflammatory, sedative and antimicrobial activities. In addition, it is the chief source of anticancer agent (shikimic acid). Current review highlights the information relating to the botany, conventional uses, phyto-chemistry and pharmacology together with the toxicology of Illicium verum.
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Cedrus deodara (Roxb. Ex D. Don) G. Don is a conifer that grows in the Himalayan regions of India, Pakistan, and Nepal. The plant is an evergreen tree belonging to the family Pinaceae and forms extensive forest along the Himalayan Mountain. The plant is traditionally used by people for thatching, sheltering, furniture making, fuelwood, and medicinal purposes. The plant is rich in flavonoids and terpenoids such as deodarin, cedrusone A, myricetin, 2R, 3R-dihydromyricetin, quercetin, 2R, 3R-γ-amorphene. Research has been carried out to explore the pharmacological and antimicrobial activities of various parts of the plants with promising outcome. Extensive literature survey was made and the information in relation to C. deodara was pooled from scientific research papers through electronic search tools available in the internet. This review paper is an attempt to highlight the ethnobotanical, pharmacological, and antimicrobial importance of C. deodara along with its wide array of chemical constituent. The plant can be a potent and cheap source of raw materials, leading to drug development for the benefit of the population of India and adjoining countries.
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The purpose of this study was to compare the essential oil composition of Inula viscosa leaves by hydrodistillation (HDE), ultrasonic (UDE) and solvent (SE) extractions followed by hydrodistillation. The total polyphenol and flavonoid contents and their antioxidant effects were studied by different solvent of extraction: ethanol (ET), ethyl acetate (EA), methanol (ME) and aqueous (AE). The principal compounds for HDE were: 2-hexenal (3.70%), caryophyllene oxide (3.11%), γ-selinene (3.09%), 3-hexen-1-ol (2.00%), eugenol (1.70%) and trans-caryophyllene (1.34%), while for UDE were: γ-selinene (5.68%), caryophyllene oxide (4.87%), trans-caryophyllene (1.99%) and nerolidol (1.74%). The oil obtained by SE was shown to contain tridecane (3.89%), dodecane (3.08%), trans-caryophyllene (2.94%), caryophyllene oxide (2.56%) and nerolidol (2.53%). Significant changes on phenolic contents were found between the different solvent of extraction. ME and AE extracts led to the highest total polyphenol (PHL) and flavonoid (FL) amounts. The anti-radical activity and reducing power were maximal in AE and ME extract. HPLC examination established that the ferulic acid as major phenolic acid in ME and AE fractions, whereas luteolin was the main compound of EA and ET fractions.
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Shikimic acid is an important intermediate for the manufacture of the antiviral drug oseltamivir (Tamiflu®) and many other pharmaceutical compounds. Much of its existing supply is obtained from the seeds of Chinese star anise (Illicium verum). Nevertheless, plants cannot supply a stable source of affordable shikimate along with laborious and cost-expensive extraction and purification process. Microbial biosynthesis of shikimate through metabolic engineering and synthetic biology approaches represents a sustainable, cost-efficient, and environmentally friendly route than plant-based methods. Metabolic engineering allows elevated shikimate production titer by inactivating the competing pathways, increasing intracellular level of key precursors, and overexpressing rate-limiting enzymes. The development of synthetic and systems biology-based novel technologies have revealed a new roadmap for the construction of high shikimate-producing strains. This review elaborates the enhanced biosynthesis of shikimate by utilizing an array of traditional metabolic engineering along with novel advanced technologies. The first part of the review is focused on the mechanistic pathway for shikimate production, use of recombinant and engineered strains, improving metabolic flux through the shikimate pathway, chemically inducible chromosomal evolution, and bioprocess engineering strategies. The second part discusses a variety of industrially pertinent compounds derived from shikimate with special reference to aromatic amino acids and phenazine compound, and main engineering strategies for their production in diverse bacterial strains. Towards the end, the work is wrapped up with concluding remarks and future considerations.
This book, which contains 99 chapters, focuses on the growing body of knowledge on the role of various dietary plants in reducing disease. Most of the expert reviews define and support the actions of bioflavonoids, antioxidants and similar materials that are part of dietary vegetables, dietary supplements and nutraceuticals. The book's chapters have various general groupings. Some herbal remedies are being developed based upon historic and cultural uses of certain plants and their constituents in disease prevention and health promotion. Discussions of Japanese, African, Korean and South American plants and their extracts help understanding of their potential roles in health as well as historical evidence for their usefulness. Since the goal of this book is to get experts to explore the ways nutraceutical supplements or foods and herbal medicines prevent disease and cancer or promote health, a major section focuses on many plants and health promotion. These include health concerns such as glucose lowering, bone mineral changes, cramps, cognitive function, osteoarthritis, sleep, skin health, weight reduction, eye protection and many others. The conclusions and recommendations from the various chapters will provide a basis for change as well as application of new extracts and botanicals in preventing cancers and health promotion.
The increased resistance of pathogenic bacteria to multiple antimicrobial agents is becoming a significant public health threat. For many pathogenic bacteria there are already limited or no effective antimicrobials available to treat the infections caused by them. Acinetobacter baumannii is a Gram‐negative, biofilm‐forming, nonmotile coccobacillus and a major human pathogen causing hospital‐acquired infections, such as ventilator‐associated pneumonia, bacteraemia, meningitis, and urinary tract and wound infections. There is therefore a clear need to discover new compounds and strategies to overcome widespread antimicrobial resistance, with a focus on A. baumannii strains. Star anise (Illicium verum Hook. f.) has been widely used as an ingredient in traditional Chinese cooking, as a flavouring agent, and as a medicine for over 3000 years; however, the essential oil (EO) isolated from star anise has not been further characterized in terms of its bioactivities and potential applications. In this work, a screening of the biological properties of star anise EO together with its chemical characterization were performed. Special attention was given to the impact of this EO in the formation of biofilms by A. baumannii. It was demonstrated that star anise EO is able to scavenge free radicals, to inhibit lipid peroxidation, and to inhibit protein denaturation, which is associated with its antioxidant and anti‐inflammatory properties. Moreover, the effects of the EO on the planktonic and biofilm cells of A. baumannii, inhibiting the formation of biofilms, dispersing preformed biofilms, and decreasing the capacity of the bacterial cells to adhere to polystyrene, together with its ability to inhibit quorum sensing, were also demonstrated.
Shikimic acid is a natural product of industrial importance utilized as a precursor of the antiviral Tamiflu. It is nowadays produced in multihundred ton amounts from the extraction of star anise ( Illicium verum) or by fermentation processes. Apart from the production of Tamiflu, shikimic acid has gathered particular notoriety as its useful carbon backbone and inherent chirality provide extensive use as a versatile chiral precursor in organic synthesis. This review provides an overview of the main synthetic and microbial methods for production of shikimic acid and highlights selected methods for isolation from available plant sources. Furthermore, we have attempted to demonstrate the synthetic utility of shikimic acid by covering the most important synthetic modifications and related applications, namely, synthesis of Tamiflu and derivatives, synthetic manipulations of the main functional groups, and its use as biorenewable material and in total synthesis. Given its rich chemistry and availability, shikimic acid is undoubtedly a promising platform molecule for further exploration. Therefore, in the end, we outline some challenges and promising future directions.
The aromatic constituents and their changes of Illicium verum during different heating processes and the practical applications were investigated in this study. Results of gas chromatography-mass spectrometry (GC–MS), gas chromatography olfactometry (GC–O) and corresponding sensory assessment showed that trans-anethole was the most representative and important component of aromatic volatiles in Illicium verum, which would cover up the scents of other ingredients. Furthermore, these results implied that the volatilization of trans-anethole reached the maximum at 100 °C during direct heating process and at 160 °C during frying heating process, which showed high similarity in sensory evaluation. The present study would provide the theory base for maximum utilizing the flavor of Illicium verum in food processing.