Germacranes and m-menthane from Illicium lanceolatum.

Abstract

Three new germacrane sesquiterpenes and a new m-menthane monoterpene were isolated together with four known compounds from the pericarp of Illicium lanceolatum, an adulterant to star anise (Illicium verum). All compounds were isolated from Illicium plants for the first time. The absolute stereochemistry of all germacranes and m-menthane was established by a combination of NMR and the modified Mosher's ester method. The biological activity was evaluated on SH-SY5Y neuroblastoma cell line. (1S,5R,7R)-1,5-Dihydroxygermacra-4(15),10(14),11(12)-triene (at 62.5 µM) and (1R,5R,7R)-1,5-dihydroxygermacra-4(15),10(14),11(12)-triene (at 15.6 µM) promoted the proliferation of SH-SY5Y by 36.2% and 45.8%, respectively, after 48 h incubation, indicating potential neurotrophic activity.

• Authors: Ming Zhao, Xianming Zhang, Yan Wang, Min Huang, Jin-Ao Duan, Tanja Gödecke, Karina M Szymulanska-Ramamurthy, Zhiqi Yin, Chun-Tao Che
• Journal: Molecules (Basel, Switzerland) (Molecules) Vol. 19 Issue 4 Pg. 4326-37 (Apr 04 2014) ISSN: 1420-3049 [Electronic] Switzerland
• PMID: 24714194 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Monoterpenes
• Neuroprotective Agents
• Plant Extracts
• Sesquiterpenes, Germacrane

Topics

• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Fruit (chemistry)
• Humans
• Illicium (chemistry)
• Monoterpenes (chemistry, isolation & purification, pharmacology)
• Neurons (cytology, drug effects)
• Neuroprotective Agents (chemistry, isolation & purification, pharmacology)
• Plant Extracts (chemistry)
• Sesquiterpenes, Germacrane (chemistry, isolation & purification, pharmacology)