A new acorane sesquiterpene glucoside, 1 R,3S,4R,5R,10R-3,10-dihydroxyacoronene-3-O-β-D-glucoside (1), was isolated from the EtOAc-soluble partition of the ethanol extract of Lysionotus paucflorus, together with six known compounds, namely p-hydroxybenzoic acid (2), vanillic acid (3), caffeic acid (4), β-ydroxypropiosyringone (5), α,β-dihydroxypropiosyringone (6), and lyoniresinol (7). The structure of the new compound was elucidated on the basis of spectroscopic methods, including D and 2D NMR, and high-resolution MS analysis. The absolute configuration of 1 was determined from CD spectra. When evaluated against several bacterial and fungal strains, and human cancer cell lines, compound 1 and its aglycone were inactive.
State Administration of Traditional Chinese Medicine (2004) Zhong Hua Ben Cao. Shanghai Science and Technology Press, Shanghai, 7, 6533–6534.
2.
(a) LiuY., SeligmannO., WagnerH., BauerR. (1995) Paucifloside, a new phenylpropanoid glycoside from Lysionotus pauciflorus. Natural Product Letters, 7, 23–28; (b) Liu Y, Wagner H, Bauer R. (1996) Nevadensin glycosides from Lysionotus pauciflorus. Phytochemistry, 42, 1203–1205; (c) Liu Y, Wagner H, Bauer R. (1998) Phenylpropanoids and flavonoid glycosides from Lysionotus pauciflorus. Phytochemistry, 48, 339–343.
3.
(a) YangF.M., YangX.S., LuoB., ZhuH.Y. (2003) Studies on the chemical constituents of Lysionotus pauciflorus Maxim. Natural Product Research and Development, 15, 508–509; (b) Feng WS, Li Q, Zheng XK, Kuang HX. (2006) Chemical constituents from Lysionotus pauciflorus. Natural Product Research and Development, 18, 617–620; (c) Wen QF, Zhong YJ, Su XH, Li CY, Liu J, Li YF, Liang B. (2013) A new acorane sesquiterpene from Lysionotus pauciflorus. Chinese Journal of Natural Medicines, 11, 185–187.
4.
BurgstahlerA.W., BarkhurstR.C. (1970) π-π* Region Cotton effects of cyclic conjugated dienes and enones. Interpretation in terms of allylic axial chirality contributions. Journal of the American Chemical Society, 92, 7601–7603.
5.
SnatzkeG. (1965) Circulardichroismus IX: Modifizierung der octantenregel für α, β-ungesättigte ketone: transoide enone. Tetrahedron, 21, 421–438.
6.
(a) HuJ., ZhangW.D., LiuR.H., ZhangC., ShenY.H., XuX.K., LiangM.J., LiH.L. (2006) Chemical constituents in root of Zanthoxylum nitidum. China Journal of Chinese Materia Medica, 31, 1689–1691; (b) Chen L, Kang WY. (2009) Chemical constituents from Aeschynanthus longicaullis. China Journal of Chinese Materia Medica, 34, 2758–2760; (c) Nakazawa T, Ohsawa K. (1998) Metabolism of rosmarinic acid in rats. Journal of Natural Products, 61, 993–996; (d) Lee TH, Kuo YC, Wang GJ, Kuo YH, Chang CI, Lu CK, Lee CK. (2002) Five new phenolics from the roots of Ficus beecheyana. Journal of Natural Products, 65, 1497–1500; (e) Li L, Seeram NP. (2010) Maple syrup phytochemicals include lignans, coumarins, a stilbene, and other previously unreported antioxidant phenolic compounds. Journal of Agricultural and Food Chemistry, 58, 11673–11679.