title: Brine shrimp lethality test active constituents and new highly oxygenated seco-prezizaane-type sesquiterpenes from Illicium merrillianum.
abstract: In the study of bioactive substances in Illicium plants, the methanol extract of I. merrillianum showed brine shrimp lethality test (BST) activity at 200 microg/ml. Bioassay-guided fractionation of the BST active fractions resulted in the isolation of 4-O-methyleudesm-11-en-4alpha-ol, eudesmol-11-en-4alpha-ol and (-)-hinokinin as potent BST active compounds. On the other hand, four new highly oxygenated seco-prezizaane-type sesquiterpenes, merrilliortholactone (1), 2alpha-hydroxycycloparvifloralone (2), 2alpha-hydroxycycloparviflorolide (3), and 2alpha-hydroxyanisatin (4) were isolated from the BST-inactive polar fractions. The structures of new compounds were elucidated by extensive analyses of spectral data. Furthermore, the absolute configuration of 3 was established by the modified Mosher's method. Compounds 1--4 showed neither BST activity at 100 microg/ml nor neurite outgrowth-promoting activity.
authors.affiliation: Institute of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
authors.forename: Jian-Mei
authors.initials: JM
authors.lastname: Huang
authors.forename: Kousuke
authors.initials: K
authors.lastname: Nakade
authors.forename: Mamiko
authors.initials: M
authors.lastname: Kondo
authors.forename: Chun-Shu
authors.initials: CS
authors.lastname: Yang
authors.forename: Yoshiyasu
authors.initials: Y
authors.lastname: Fukuyama
mesh_terms: D000818:Animals; D001156:Artemia / Q000187:drug effects*; D002850:Chromatography, Gel; D005638:Fruit / Q000737:chemistry; D029523:Illicium / Q000737:chemistry*; D007928:Lethal Dose 50; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010100:Oxygen / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D010936:Plant Extracts; D012717:Sesquiterpenes; D010100:Oxygen