New Eremophilane Sesquiterpenes from Cacalia ainsliaeflora

Abstract

One known eremophilanolide, 3β-angeloyloxy-8β,10β-dihydroxy-6β-methoxyeremophilenolide (1) and seven new eremophiane sesquiterpenes, 3β-angeloyloxy-6β-ethoxy-8β,10β-dihydroxyeremophilenolide (2), 3β,6β-diangeloyloxy-10α-hydroxy-8α-methoxyeremophilenolide, 6β-angeloyloxy-8β,10β-dihydroxy-3-oxo-eremophilenolide, 6β,8β,10β-trihydroxy-3-oxo-eremophilenolide, 3β-angeloyloxy-6β,10β-dihydroxy-eremophila-7(11),8(9)-dien-8,12-olide (6), 3β-angeloyloxy-10β-hydroxy-6β-methoxy-eremophila-7(11),8(9)-dien-8,12-olide, 3β-angeloyloxy-8-oxo-eremophila-6.9-dien-12-oic acid ethyl ester, were isolated from the roots of Cacalia ainsliaeflora. Their structures were elucidated by spectroscopic methods. Compounds 1, 2 and 6 were assayed against both Gram-positive and Gram-negative bacteria. No positive activities were observed.

Key words

Cacalia ainsliaeflora - Compositae - eremophilane sesquiterpenes

References

• 1 Jiangsu College of New Medicine. A Dictionary of the Traditional Chinese Medicines. Shanghai Science and Technology Press Shanghai; 1997 22
• 2 Mao M J, Jia Z J. Eremophilane sesquiterpenes from Cacalia ainsliaeflora .  Planta Medica. 2002;  68 55-9
• 3 Demetzos C, Stahl B, Anastassaki M. , et al . Chemical analysis and antimicrobial activity of the resin Ladano, of its essential oil and of the isolated compounds.  Planta Medica. 1999;  65 76-8
• 4 Zhang S M, Zhao G L, Li R, Lin G Q. Eremophilane sesquiterpenes from Cacalia roborowskii .  Phytochemistry. 1998;  48 519-24
• 5 Sugama K, Hayashi K, Mitsuhashi H. Eremophilenolides from Petasites japonicus .  Phytochemistry. 1985;  24 1531-5
• 6 Massiot G, Nuzillard J M, Olivier L, Aclinou P, Benkouider A, Khelifa A. Eremophilenolides from Hertia cheirifolia .  Phytochemistry. 1990;  29 2207-10
• 7 Aclinou P, Benkouider A, Massiot G, Olivier L. Eremophilenolides from Hertia cheirifolia .  Phytochemistry. 1991;  30 2083-4
• 8 Naya K, Matsuura T, Makiyama H, Tsumura M. The conversion of furanoeremophilanes to epieremophilenolides.  Heterocycles. 1978;  10 177-84
• 9 Naya K, Kanazawa R, Sawada M. The photosensitized oxygenation of furanoeremophilanes. I. The isomeric hydroperoxides from petasalbin and their transformations to lactones.  Bulletin of the Chemical Society of Japan. 1975;  48 3220-5
• 10 Moriyama Y, Takahashi T. New sesquiterpene lactones of eremophilane-type from Ligularia fauriei (Fr.) Koidz.  Bulletin of the Chemical Society of Japan. 1976;  49 3196-9
• 11 Zhao Y, Jia Z J, Tan R X, Yang L. Eremophilanolides from the roots of Ligularia veitchiana .  Phytochemistry. 1992;  31 2785-7
• 12 Yaoita Y, Kikuchi M. Structure of new eremophilane derivatives from the rhizomes of Petasites japonicus Maxim.  Chem Pharm Bull. 1995;  43 1738-43
• 13 Jia Z J, Zhao Y, Tan R X. New sesquiterpenes from the roots of Ligularia veitchiana .  Journal of Natural Products. 1993;  56 494-9
• 14 Jia Z J, Zhao Y, Peng H R. Eight new eremophilane derivatives from the roots of Ligularia przewalsk II.  Journal of Natural Products. 1995;  58 1358-64
• 15 Zhao Y, Jia Z J, Yang L. Novel sesquiterpenes from Ligularia veitchiana .  Planta Medica. 1994;  60 91-2