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Review on Chemical Constituents and Biological Activities of Genus Anthemis Pharmacogn J. 2019; 11(5):1155-1166. A Multifaceted Journal in the field of Natural Products and Pharmacognosy Review Article www.phcogj.com Review on Chemical Constituents and Biological Activities of Genus Anthemis Rima Boukhary*, Maha Aboul-ElA, Abdalla El-Lakany ABSTRACT Genus Anthemis of Family Asteraceae contains mainly flavonoids, sesquiterpene lactones belonging to germacranolides, eudesmanolides, guaianolides, sterols and essential oils. The Plants of genus Anthemis have been known to have anti-inflammatory, hepatoprotective Rima Boukhary*, Maha Aboul- and antioxidant activities due to their rich contents of important physiological and biological ElA, Abdalla El-Lakany compounds. They are referred to as nature’s biological response modifier’s and are involved in energy transfer, photosensitization and morphogenesis. Several clinical studies have Department of Pharmaceutical Sciences, Faculty of Pharmacy, Beirut Arab University, shown that people who take diets rich in flavonoids and sesquiterpenes have reduced risk 115020 Beirut, LEBANON. of developing cancer and cardiovascular diseases. This article covers most of constituents of plants of genus Anthemis reported from 2002 up to 2018. Furthermore, the biological activities Correspondence of plants of genus Anthemis will be presented. Rima Boukhary Key words: Anthemis, Flavonoids, Sesquiterpenes, Anti-oxidant, Anti-inflammatory. Department of Pharmaceutical Sciences, Faculty of Pharmacy, Beirut Arab University, 115020 Beirut, LEBANON. INTRODUCTION antispasmodic and for the treatment of inflammatory E-mail: [email protected] diseases in Europe.12,13 In June 2014, Yusufoglu et al. History Genus Anthemis comprises approximately 210 evaluated the antiinflammatory and hepatoprotective • Submission Date: 05-05-2019; species 51 of which belong to Turkish flora. properties of Anthemis scrobicularis in rats against • Review completed: 17-05-2019; Anthemis is a genus of aromatic flowering plants carrageenan induced inflammation and carbon • Accepted Date: 24-05-2019. closely related to Chamaemelum which is known tetrachloride (CCl ) induced hepatic injury.14 They as chamomile. Some species are also called dog- 4 DOI : 10.5530/pj.2019.11.180 found that this plant plays an important role in fennel or mayweed. They are endogenous to the increasing the curative capacity of kidney and liver. Article Available online Mediterranean region and southwest Asia east In 2014 Bardaweel et al. reported that, Anthemis http://www.phcogj.com/v11/i5 to Iran. A number of species have also become palestina exhibited antioxidant and anticancer Copyright naturalized in the United Kingdom and other activities due to the presence of flavonoids.15 1,2 © 2019 Phcogj.Com. This is an open- parts of the world. The Anthemidinae consist of Moreover, it was reported to be active against MCF- access article distributed under the terms the genus Anthemis with conditional addition of 7, MDA-MB-468 and UACC-257 cancer cell lines.16 of the Creative Commons Attribution 4.0 the monotypic genus Nananthea DC.3 All have a International license. tiny, chaffy scale between each two florets, which Researchers are still working on determining is very small and is considered as a main feature the biological activities of flavonoids playing an of the genus Anthemis. The diameter of capitula important role in curing and preventing several is 8-20 mm; the receptacle is solid and its base is health ailments such as cardiovascular diseases, surrounded by an involucres comprising 2-3 rows diabetes and cancer.17,18 Antioxidants are compounds of compact and imbricated bracts with scarious that protect cells against the damaging effects of margins. All florets are ligulate, but a few pale yellow reactive oxygen species due to reactions with DNA, tubular florets occur in the central region. Ligulate proteins and lipids. Flavonoids have been found to florets are white, dull, lanceolate and reflexed with have an additive effect to endogenous scavenging a dark brown, inferior ovary, a filiform style and compounds and because of their potential a bifid stigma; tubular florets have a five-toothed therapeutic significance, the number of identified corolla tube, 5 syngenesious, epipetalous stamens flavonoids is increasing rapidly and extensive and a gynoecium similar to that of the ligulate screening of their actions is being carried out in many florets.2,3 laboratories.19,20 This article deals with the previously separated sesquiterpenes and flavonoids isolated The genus Anthemis is characterized mainly by from a variety of Anthemis plants and published in the presence of sesquiterpene lactones, belonging periodicals, monographs and other related sources to germacranolides, eudesmanolides, guaianolides during the period 2003 till 2018 as shown in Tables and flavonoids.4-6 Constituents of Anthemis 1, 2 and 3. Moreover, examples of illustrative photos species were proven to exert anti-inflammatory, of Anthemis species growing in Lebanon are shown hepatoprotective and antioxidant activities.7,8 below in Figures 1 and 2. Anthemis species are commonly used in folk medicine in the treatment of gastrointestinal It has been reported that different parts of Anthemis disorders, hemorrhoid, dysmenorrhoea and plant (leaf, stem, root, seed) contain many stomach ache in Turkish traditional medicine.9-11 constituents including flavonoids, sesquiterpenes, Extracts, tinctures, salves and tisanes from both carboxylic acids and other phytoconstituents aerial and root parts are used as antibacterial, possessing diverse pharmacological properties.19,20 Cite this article: Boukhary R, Aboul-ElA M, El-Lakany A. Review on Chemical Constituents Phcogj.com and Biological Activities of Genus Anthemis. Pharmacog J. 2019;11(5):1155-66. 1155 Pharmacognosy Journal, Vol 11, Issue 5, Sep-Oct, 2019 Boukhary, et al.: Review on Chemical Constituents and Biological Activities of Genus Anthemis Table 1. Previously isolated sesquiterpene lactones from genus Anthemis. Name Chemical structure Natural source(s) Ref. 1 Faurinone Anthemis var. discoidea 16 2 Isofaurinone 3 Deacetyl-β -cyclopyrethrosin 24 A. wiedemannia 4 Tatridin A 24 A. wiedemannia 5 1-epi-tatridin B 6 Antheindurolides A. arvensis L. 25 7 6,7Z-dehydro-5,6-dihydroanthecotuloide A. indurata 8 Anthecotuloid Δ5 E 26 A. cotula 9 6,7E-dehydro5,6-Dihydroanthecotuloide Δ6 E A. arvensis L. 25 5-hydroperoxy-6,13-dehydro-5,6-dihydro- 10 anthecotuloide A. indurata 26 11 5-oxo-6,13-dehydro-5,6-dihydroanthecotuloide A. cotula 12 5-oxo-6,7Z-dehydro-5,6-dihydroanthecotuloide 27 28 A. pseudocotula 13 8-O-dihydroanthecotuloide Pharmacognosy Journal, Vol 11, Issue 5, Sep-Oct, 2019 1156 Boukhary, et al.: Review on Chemical Constituents and Biological Activities of Genus Anthemis Name Chemical structure Natural source(s) Ref. 14 Antheindurolide B 2,10-Dihydroxy-8-angeloxy-9-acetoxyguaia-3,11(13)- 15 diene-6,12-olide A. alpestris 29 A. altissima 16 Sivasinolide 17 Altissin (Desacetyl Bcyclopyrethrosin ) 30 18 Tatridin-A 30 A. altissima 19 1-Epi-tatridin B 20 1R,10B-epoxy-6-hydroxy-1,10H-inunolide 4α, 9α-Diacetoxyguaia-2, 1(10), 11(13)-trien-12, 21 6α-olide. A. rumelica 31 1α, 4B-dihydroxy-11Hα-guaia-2, 10(14)-dien-12, 6 22 α-olide. 23 Nobilin Anthemis nobilis L. 20 1157 Pharmacognosy Journal, Vol 11, Issue 5, Sep-Oct, 2019 Boukhary, et al.: Review on Chemical Constituents and Biological Activities of Genus Anthemis Table 2. Previously isolated flavonoids from genus Anthemis. # Name Chemical structure Natural source(s) Ref. 1 Salvigenin A. Odontosthephana 32 2 Apigenin 3 Naringenin 4 Quercetin 32 A. ruthenica 33 5 Rhamnetin 33 A. altissima 6 Taxifolin 7 A. rumelica 31 Centauridin 8 Santin Pharmacognosy Journal, Vol 11, Issue 5, Sep-Oct, 2019 1158 Boukhary, et al.: Review on Chemical Constituents and Biological Activities of Genus Anthemis 9 Kaempferol A. altissima 33 27 10 Pectolinaringenin A. odontostephana 34 OH HO O OH 11 Patuletin A. tinctoria 35 O OH OH O 12 Tamarixetin A. cupaniana 30 13 Jaceosidin A. stiparum Pomel 26 14 Eupatilin A. cotula A. nobilis. L 34 15 Hispidulin 1159 Pharmacognosy Journal, Vol 11, Issue 5, Sep-Oct, 2019 Boukhary, et al.: Review on Chemical Constituents and Biological Activities of Genus Anthemis Table 3: Previously isolated phenolic acids from genus Anthemis # Name Chemical structure Natural source(s) Biological properties Ref. They have potential anti-inflammato- 30 ry, anti-diabetic, antioxidant proper- 1 Clorogenic acid A. altissima ties and used in asthma treatment. A. montana 2 Caffeic acid 34 A. triumphetti A. tinctoria 3 Rosemarinic acid Anticancer properties of rosmarinic acid against different cancer types. 35 Figure 1. A photograph of Anthemis chia. L. Figure 2. A photograph of Anthemis tinctorial. Pharmacognosy Journal, Vol 11, Issue 5, Sep-Oct, 2019 1160 Boukhary, et al.: Review on Chemical Constituents and Biological Activities of Genus Anthemis Compounds were identified by HPLC, Gas chromatography NMR, rosemarinic and caffeic acids isolated from A. triumfetta, A. altissima MS and UV. The chemical structures of the constituents of the plants and other species.19-21 of Genus Anthemis are presented in Tables 1, 2 and 3. Their different biological activities will be proved in the following paragraphs. Anthecotuloide is an irregular sesquiterpene lactone isolated from A. cotula L. Its expected biosynthetic pathway was via two pathways, Sesquiterpene lactones have a distinctive biological activity connected either a Non-Farnesyl Diphosphate (FPP) Route or by head to head to the presence
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