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ABDOLHOSSEIN RUSTAIYAN(11091)Set.Pmd ORIENTAL JOURNAL OF CHEMISTRY ISSN: 0970-020 X CODEN: OJCHEG An International Open Free Access, Peer Reviewed Research Journal 2017, Vol. 33, No.(5): Pg. 2188-2197 www.orientjchem.org Sesquiterpene Lactones of Iranian Compositae Family (Astraceae); Their Chemical Constituents and Anti-plasmodial Properties of Tehranolide (A.Review) ABDOLHOSSEIN RUSTAIYAN1*, AFSANEH FARIDCHEHR2 and MAHDI BAKHTIYARI3 1,2Department of Chemistry, Faculty of Basic Sciences. Science and Research Branch Islamic Azad University, Tehran, Iran 3Shahdara Caspian, Pharmaceutical and Cosmetic Company, Tehran, Iran. *Corresponding author E-mail: [email protected] http://dx.doi.org/10.13005/ojc/330506 (Received: May 06, 2017; Accepted: June 30, 2017) ABSTRACT Sesquiterpene lactones constitute a large and diverse group of biologically active plant chemical that have been identified in the several plant families.The pharmacological properties of interest involving the sesquiterpene lactones are their antibacterial, antifungal and anti-plusmodial activities.Indeed, assessing the biological activities of the sesquiterpene lactones found in plants and their essential oil is of great medicinal importance because they could potentially be utilized as therapeutic agents for the treatment of such infections. Keywords: Iranian Compositae Family (Asteraceae), Germacranolides, Eudesmanolides, Guaianolides, Elemanolides, Constituents and Biological Activities. INTRODUCTION cells in most of the Asteraceae, but can also be found within the vacuoles of other cell types in the Sesquiterpene lactones are one of the plant, specifically when produced in response to most prevalent and biologically significant classes biotic stresses. They are one of the main of secondary metabolite present, and as such have constituents of latex in latex producing plants, and subject to a number of studies. they are frequently potent antimicrobial agents as well as antifeedants to chewing insects and birds. Sesquiterpene lactones are a group of They also have a range of other effects such as secondary metabolites found across the plant allelopathy, stimulation of germination in the kingdom comprising a large group of over 5500 parasitic plant Orobanche2. known compounds1being most prevalent in the family Asteracea. Sesquiterpenoids are typically In fact, The Iranian compositae (Astracea) located in laticifers, which are specialized secretary family has yielded a considerable amount of new, interesting sesquiterpene lactones. RUSTAIYAN et al., Orient. J. Chem., Vol. 33(5), 2188-2197 (2017) 2189 Chemical constituents related guaianolides13 and 15.The structures Onopordon leptolepis DC. followed from the H1-NMR data, especially if Onopordon leptolepis DC. Growing in Iran compared with those of 10-12.Acetylation of 13 has not been investigated before. The aerial parts gave the diacetate14; its H1-NMR data showed that also contain Onopordopicrin 1, and two new the stereochemistry at C-5, through C-8 was the germacranolides (2 and 3), closely related to 23. same as that of 9-12, which the presence of a C-4 methylene group was indicated by two broadened O OH OR' signals at δ 5.68 and 5.43 ppm in the spectra 11 O of 13 . O O 14 14 RO HO Cl 1 O O H O H O 2 R=H,R'=COC(Me)=CH2 2 10 9 9 R= Cl 2 1 1 3 R = H, R'= COCH(Me)2 HO HO 3 8 OR OH O OH O O 4 5 7 HO 6 O 10 R= H O O 11 H OR' 13 15 15 Cl O 12 O O 11 R= OH 12 O O R O O HO 4 R= CH2OH 5 R= CHO 14 14 RO R' = H R'= H H O H O 10 2 9 1 2 RO HO 1 Fig. 1. Chemical structures of Sesquiterpene lactones 3 8 O 3 8 O 5 4 HO 7 from Onopordon leptolepis DC.1-5. 7 6 H H H 15 11 O 15 O 13 The investigation of the polar fractions of 13 R= H 12 the aerial parts of Onopordon leptolepis afforded O 14 R= Ac 15 O Fig. 3.Chemical structures of Sesquiterpene lactones two new elemanolides, their structures being from Acroptilon repens DC.9-15 elucidated by spectroscopic methods and by partial synthesis starting with Onopordopicrin4. Guaianolides from Centaurea behen L. Centaurea behen L. native in Iran had not A Guaianolide from Jurinea carduiformis Boiss. been investigated chemically. The aerial parts of The aerial parts of J. carduiformis. afforded, this plant afforded several sesquiterpene lactones, in addition to Repin(6)5 and Janerin(7)7, small the guaianolides cynaropicrin (16)12, arguerin B amounts of a further lactone 8, the structure of which (18)13, desacylcynaropicrin (19)14, grosshemin was deduced from the H1-NMR data especially by (21)15 and minor amounts of the ketone 23, which comparison with the spectra of 6 and 77. is closely related to solstitialin A, the absolute configuration of which had been established16. O H Structure 23 could only be isolated as its diacetate 2 10 6 R= 24, which still was mixed with the acetate of 21. The 9 O 1 latter, however, could be separated from 24 after 3 8 OR HO 4 5 OH transformation to the corresponding pyrazoline 7 7 R= 6 derivative. The structures of 16, the corresponding O H O 13 O 8 R= H H 2 10 9 16 17 18 19 20 1 R'O 3 8 OR OH OAc 4 5 R H Ac O 7 6 O O O H R' HAc H H Ac 15 Fig. 2.Chemical structures of Sesquiterpene lactones 13 O from Jurinea carduiformis Boiss.6-8 O Guaianolides from Acroptilon repens DC. H H O The aerial part of A. repens (Centaurea picris) O DC. has been investigated several times8. Two OR 21 R= H 23 R= H 24 R= Ac H 22 R= Ac H 8 guaianolides were isolated, chlorohyssopifolin C (9) O O and Repin (10) 9.A reinvestigation afforded, in addition OR OR O O to these lactones, Janerin (11)7, chlorohyssopifolin A Fig. 4.Chemical structures of Sesquiterpene lactones (12)10 and two other lactones, which are the closely from Centaurea behen L.16-24 2190 RUSTAIYAN et al., Orient. J. Chem., Vol. 33(5), 2188-2197 (2017) diacetate 17, 18, 19 and 21 were elucidated by group could be deduced from the spectrum which their H1-NMR data17. was in part close to that zaluzanin C acetate 21. 20 H R' 1 32 33 34 35 36 O OH 9 2 10 16 17 18 AcO R' H H OH OAc OAc 8 OR" R" HAc H H Ac O 5 7 3 19 H 4 6 OH 11 13 O 12 15 O HO O 25 O Fig. 5.Chemical structure of Sesquiterpene lactone Fig. 7. Chemical structure of Sesquiterpene lactone from from Centaurea brugueriana DC. 25. Centaurea kandavanensis Wagenitz. 32-36. The more polar lactone 34, Molecular α Chemical Constituents of Centaurea brugueriana formula C17H20O6, obviously was the 9 -hydroxy DC. derivative of 32. This investigation shows again that Cinicin a germacranolide has been guaianolide derived from zaluzanin C may be isolated from chloroform extract of the aerial parts characteristic for large parts of the genus Centaurea 22. 18 14 of Centaurea brugueriana DC. (Compositae) . O H 14 10 H H 2 9 1 2 10 26 R= H O 38O 1 9 5 3 27 R= OAc R"O 4 7 OH 8 4 5 OR H 6 6 7 R"O H OR 11 15 H H 15 13 OR O 11 Cl 12 O R' O 12 13 37 O O O CH3 Fig. 8. Chemical structure of Sesquiterpene lactone 29 30 31 28 R= HC C CH2 Cl CH3 O OH from Aegopordon berarioides Boiss. 37. R'= Cl R"= H O C OH A New Guaianolide from Aegopordon berarioides H Cl OH Ac Boiss. H H Ac The aerial parts of A. berarioides afforded, Fig. 6. Chemical structure of Sesquiterpene lactone from in addition to lupeol, taraxasterol, sitosterol-3-O- Centaurea imperialis Hausskn.ex Bornm. 26-31. glucoside and cynaropicrin and a new guaianolide, Centaurea imperialis the structure of which was deduced by high-field The aerial parts of Centaurea imperialis H1-NMR spectroscopy. The plant materials were afforded three new guaianolides, 3-desoxysolstitialin A collected in west of Kerman, Iran 23. and two derivatives of centaurepensin19. Sesquiterpene Lactones and Eudesmane Guaianolides from Centaurea kandavanensis Derivatives from Onopordon carmanicum (Bornm.) Wagenitz. Bornm. From the large genus Centaurea The aerial parts of Onopordon carmanicum (Compositea) numerous different types of (Bornm.) Bornm afforded in addition to Onopordopicrin constituents, especially guaianolides, have been and two related esters the epoxide of reported 20. We now have investigated a species Onopordopicrin, a new elemane derivative, two which grows on the mountains near Kandavan. eudesmanolides and two eudesmane derivatives which most likely are the precursors of the latter The polar fraction afforded two crystalline lactones. The structures were elucidated by compounds, the guaianolides 32 and 34. The highfield NMR spectroscopy 24. molecular formula of 32 was C17H20O5 as followed from the mass spectrum. The H1-NMR spectrum The genus Onopordon (Compositae, tribe showed the typical signals of methylene lactones. Cynareae) is placed together with the large genera Furthermore the presence of two additional Cousinia, Saussurea and Jurinea in the subtribe exomethylene groups, acetate and a hydroxyl Carduinae. Taxonomically this genus is closely RUSTAIYAN et al., Orient. J. Chem., Vol. 33(5), 2188-2197 (2017) 2191 related to Cousinia, while the position of Jurinea Sesquiterpene Lactones from Achillea micrantha and Saussurea is uncertain25. So far from the genus M.B. Onopordon in addition to widespread compounds The aerial parts of Achillea micrantha 26 several C17-acetylenes and the germacranolide afforded the eudesmanolides santamain, reynosin, Onopordopicrin27, 28, 4, 3 as well as closely related dihydrosantamarin, dihydroerynosin and the lactones4,3 have been reported.
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