Antiviral Spirotriscoumarins A and B: Two Pairs of Oligomeric Coumarin Enantiomers with a Spirodienone-Sesquiterpene Skeleton from Toddalia asiatica.
Two pairs of oligomeric coumarin enantiomers, spirotriscoumarin A [(+)-1 and (-)-1] and spirotriscoumarin B [(+)-2 and (-)-2], with a spirodienone-sesquiterpene fused skeleton were isolated from Toddalia asiatica. Their structures were unambiguously established using spectroscopic data, X-ray diffraction analysis, and the electronic circular dichroism (ECD) method. The racemic mixtures (±)-1 and (±)-2 exhibit 3-to-6-fold stronger antiviral activity against influenza virus A (H3N2) (IC50: 3.13 and 2.87 μM, respectively) than their corresponding optically pure enantiomers.
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.
Zhong-Hai
ZH
Tang
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.
Yun-Bao
YB
Liu
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
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.
Li
L
Li
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.
Yong
Y
Li
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.
Jian-Dong
JD
Jiang
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.
Jing
J
Qu
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.
Shi-Shan
SS
Yu
D000818:Animals; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D003374:Coumarins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003588:Cytopathogenic Effect, Viral; D004285:Dogs; D053122:Influenza A Virus, H3N2 Subtype / Q000187:drug effects; D061985:Madin Darby Canine Kidney Cells; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D027821:Rutaceae / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism
D000998:Antiviral Agents; D003374:Coumarins; D012717:Sesquiterpenes; D013141:Spiro Compounds