New Sesquiterpenes from Erigeron annus

Abstract

Four new and five known eudesmane-type sesquiterpenes were isolated from the aerial parts of Erigeron annus. The structures of these new compounds were elucidated by spectral means, including 2D-NMR analysis, to be 1β,4β-dihydroxyeudesman-11-ene; 1β,7α-dihydroxyeudesman-4(15)-ene; (1R,5S,6S,7S,10R)-1β, 6α-dihydroxyeudesman-4-one and 1β-D-glucopyranosyloxy-6α-hydroxyeudesman-4(15)-ene. In addition, a chemical transformation of a known compound 1β,6α-dihydroxy-eudesman-4 (15)-ene was carried out and the derivative 1β,6α-dihydroxy-4β(15)-epoxyeudesmane was obtained. Some of the compounds were evaluated for their in vitro antitumor activities.

Erigeron annus - Compositae - eudesmane - sesquiterpenes - antitumor activity

References

• 1 Delectis Florae Reipublicae Popularis Sinicae Agendae Academiae Sinicae E dita. Flora Republicae Popularis Sinicae Institutum Botanicum Academiae Sinicae, Tomus 74. Beijing; Science Press 1985: p 296
• 2 Wu Z Y. Outline of New China Herbals. Shanghai; Shanghai Science and Technology Press 1990: p 417
• 3 Jiangsu College of New M edicine. A Dictionary of the Traditional Chinese Medicines. Beijing; Peoples’ Hygiene Publisher 1977: p 4
• 4 IIjima T, Yaoita Y, Kikuchi M. Five New Sesquiterpenoids and a New Diterpenoid from Erigeron annuus (L.) Pers., Erigeron philadelphicus L. and Erigeron sumatrensis Retz.  Chem Pharm Bull. 2003;  51 545-9
• 5 Li X Q, Gao K, Jia Z J. Eremophilenolides and other constituents from the roots of Ligularia sagitta .  Planta Medica. 2003;  69 357-60
• 6 Yang Z D, Gao K, Jia Z J. Eudesmane derivatives and other constituents from Saussurea parviflora .  Photochemistry. 2003;  62 1195-9
• 7 Wang X K. Natural medicinal chemistry. Beijing; Peoples’ Hygiene Publisher 1986: p 406
• 8 Lee S K, Nam K A, Heo Y H. Cytotoxic activity and G2/M cell cycle arrest mediated by antofine, a phenanthroindolizidine alkaloid isolated from Cynanchum paniculatum .  Planta Medica. 2003;  9 21-5
• 9 Hong X, Wang B G, Zhou J, Hao X J. A new sesquiterrpene from Michelia yunnanensis .  Chin Chem Lett. 1998;  9 939-40
• 10 Nagasampagi B A, Sohoni J S, Bohlmann F, Zdero C. Eudesmanolide and a guaianolide from Cyathocline purpurea .  Phytochemistry. 1981;  20 2034-6
• 11 Stothers J B. Carbon-13 NMR Spectroscopy. New York; Academic Press 1972: pp 134-5
• 12 Adinarayana D, Syamasundar K V. A new sesquiterpene alcohol from Pterocarpus marsupium .  Phytochemistry. 1982;  21 1083-5
• 13 Varma K R, Jain T C, Bhattacharyya S C. Terpenoids - XXXIV. Structure and stereochemistry of zingiberol and juniper camphor.  Tetrahedron. 1962;  18 979-84
• 14 Bohlmann F, Ates N ( Gören), King R M, Robinson H. Two sesquiterpenes from Senecio species.  Phytochemistry. 1983;  22 1675-7
• 15 Moffitt W, Woodward R B, Moscowitz A, Klyne W, Djerassi C. Structure and the optical rotatory dispersion of saturated ketones.  J Am Chem Soc. 1961;  83 4013-8
• 16 Yang M, Jia Z J. Studies on the constituents of Saussurea macrota, Achillea acuminata and Achillea wilsoniana and their bioactivities. Lanzhou University: Doctoral Dissertation 2004: p 78
• 17 García-Granados A, Molina A, Buruaga A SD, Buruaga J MSD. Sesquiterpenes from two subspecies of Sideritis varoi .  Phytochemistry. 1985;  24 97-101
• 18 Xu F M, Morikawa T, Matsuda H, Ninomiya K, Yoshikawa M. Structures of new sesquiterpenes and hepatoprotective constituents from the Egyptian herbal medicine Cyperus longus .  J Nat Prod. 2004;  67 569-76
• 19 Maqua M P, Vines A CG, Caballero E, Grande M C, Medarde M, Bellido I S. Components from Santolina rosmarinifolia, subspecies rosmarinifolia and canescens .  Phytochemistry. 1988;  27 3664-7
• 20 Liao J C, Zhu Q X, Yang X P, Jia Z J. Sesquiterpenes from Ligularia hodgsonii .  J Chin Chem Soc. 2002;  49 129-32
• 21 Hu J F, Bai S P, Zhu Q X, Jia Z J. New sesquiterpene and other constituents from Senecio flammeus .  Indian J Chem. 1998;  37B 607-9
• 22 Park H J, Kwon S H, Yoo K O, Sohn L C, Lee K T, Lee H K. Sesquiterpenes from the leaves of Ligularia fischeri var. spiciformis .  Planta Medica. 2000;  66 783-4
• 23 Canel C, Moraes R M, Dayan F e, Ferreira D. Molecules of interest - podophyllotoxin.  Phytochemistry. 2000;  54 115-20