Chem. Pharm. Bull., 56(8),1201-1204, August 2008

Notes

Two New Sesquiterpenoids and Two New Prenylated Phenylpropanoids from Illicium fargesii, and Neuroprotective Activity of Macranthol

Miyako MORIYAMA,^a Jian-Mei HUANG,^b Chun-Shu YANG,^b Miwa KUBO,^a Kenichi HARADA,^a Hideaki HIOKI,^a and Yoshiyasu FUKUYAMA^*,a

^a Faculty of Pharmaceutical Sciences, Tokushima Bunri University; 180 Yamashiro-cho, Tokushima 770-8514, Japan: and ^b Faculty of Pharmaceutical Sciences, Beijing University of Chinese Medicine; Beijing 100029, P. R. China. * To whom correspondence should be addressed. e-mail: fukuyama@ph.bunri-u.ac.jp

Two new seco-prezizaane-type sesquiterpenoids 1, 2 and two new prenylated phenylpropanoids 4, 5 were isolated along with 15 known compounds from Illicium fargesii. The structures of 1, 2 were elucidated as 10-O-(E)- and 10-O-(Z)-cinnamoyl-2-oxo-6-deoxyneoanisatin by analysis of spectroscopic data and by comparison of their NMR data with those of previously reported 2-oxo-6-deoxyneoanisatin (3), respectively, whereas the structures of 4, 5 were identified as 4-allyl-2-(3-methylbut-2-en-1-yl)phenol and 4-allyl-2-(2-methylbut-3-en-2-yl)phenol, respectively, on the basis of spectroscopic data. Among the isolated compounds, macranthol (7) was found to have neuroprotective activity at 5-10 μM in rat cortical neurons cultured in DMEM/N₂ medium.

Key words Illicium fargesii; seco-prezizaane-type sesquiterpenoid; prenylated phenylpropanoid; neuroprotective activity