Antiviral spirooliganones A and B with unprecedented skeletons from the roots of Illicium oligandrum.
Two novel spirooliganones A (1) and (2), a pair of spiro carbon epimers, with a rare dioxaspiro skeleton were isolated from the roots of Illicium oligandrum. The structures were fully determined by spectroscopic analysis and chemical methods, especially modified Mosher's method, and X-ray diffraction analysis. Spirooliganone B was found to exhibit more potent activities against coxsackie virus B3 and influenza virus A (H3N2) (IC50 3.70-5.05 μM) than spirooliganone A. The biosynthetic pathway involving a hetero-Diels-Alder reaction of the epimers was proposed.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
Shuang-Gang
SG
Ma
Rong-Mei
RM
Gao
Yu-Huan
YH
Li
Jian-Dong
JD
Jiang
Ning-Bo
NB
Gong
Li
L
Li
Yang
Y
Lü
Wen-Zhao
WZ
Tang
Yun-Bao
YB
Liu
Jing
J
Qu
Hai-Ning
HN
Lü
Yong
Y
Li
Shi-Shan
SS
Yu
D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D061565:Cycloaddition Reaction; D029822:Enterovirus B, Human / Q000187:drug effects; D029523:Illicium / Q000737:chemistry*; D053122:Influenza A Virus, H3N2 Subtype / Q000187:drug effects; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013237:Stereoisomerism
D000998:Antiviral Agents; D013141:Spiro Compounds; C586354:spirooliganone A