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

• Published in: Chemical & Pharmaceutical Bulletin Vol. 56; no. 8; pp. 1201 - 1204
• Main Authors: Moriyama, Miyako, Huang, Jian-Mei, Yang, Chun-Shu, Kubo, Miwa, Harada, Kenichi, Hioki, Hideaki, Fukuyama, Yoshiyasu
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.08.2008; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: Alkenes - isolation & purification; Alkenes - pharmacology; Animals; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Illicium; Illicium - chemistry; Illicium fargesii; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Molecular Structure; neuroprotective activity; Neuroprotective Agents - chemistry; Neuroprotective Agents - isolation & purification; Neuroprotective Agents - pharmacology; Pharmacology & Pharmacy; Phenols - isolation & purification; Phenols - pharmacology; Physical Sciences; prenylated phenylpropanoid; Propanols - chemistry; Propanols - isolation & purification; Propanols - pharmacology; Rats; Science & Technology; seco-prezizaane-type sesquiterpenoid; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; ANISATUM L; prenylated phenylpropanoid; BARK; COMPONENTS; DUNNIANUM; NEOANISATIN; NEOLIGNANS; seco-prezizaane-type sesquiterpenoid; NEUROTROPHIC ACTIVITY; PERICARPS; Illicium fargesii; DERIVATIVES; neuroprotective activity; CONSTITUENTS
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.56.1201

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.