Germacranes and m-menthane from illicium lanceolatum

Ming Zhao*, Xianming Zhang, Yan Wang, Min Huang, Jin Ao Duan, Tanja Gödecke, Karina M. Szymulanska-Ramamurthy, Zhiqi Yin, Chun Tao Che

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)4326-4337
Number of pages12
JournalMolecules
Volume19
Issue number4
DOIs
StatePublished - Apr 2014

Keywords

  • Absolute stereochemistry
  • Germacrane sesquiterpenes
  • Illiciaceae
  • Illicium lanceolatum
  • M-menthane monoterpene
  • Proliferative promotion
  • SH-SY5Y

ASJC Scopus subject areas

  • Drug Discovery
  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Physical and Theoretical Chemistry
  • Pharmaceutical Science
  • Organic Chemistry

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