Brine shrimp lethality test active constituents and new highly oxygenated seco-prezizaane-type sesquiterpenes from Illicium merrillianum.
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.
Huang
Jian-Mei
JM
Institute of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Nakade
Kousuke
K
Kondo
Mamiko
M
Yang
Chun-Shu
CS
Fukuyama
Yoshiyasu
Y
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
D010936:Plant Extracts; D012717:Sesquiterpenes; D010100:Oxygen