6-Deoxy- and 11-Hydroxytolypodiols: Meroterpenoids from the Cyanobacterium HT-58-2

  • J Nat Prod. 2020 May 22;83(5):1691-1695. doi: 10.1021/acs.jnatprod.9b00844.
Joshua R Gurr  1 ,  Timothy J O'Donnell  1 ,  Yuheng Luo  1 ,  Wesley Y Yoshida  1 ,  Mary L Hall  2 ,  Alejandro M S Mayer  2 ,  Rui Sun  1 ,  Philip G Williams  1
Affiliations
  • 1. Department of Chemistry, University of Hawaii at Manoa, 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States.
  • 2. Department of Pharmacology, College of Graduate Studies Medicine, Midwestern University, 555 31st Street, Downers Grove, Illinois 60515, United States.
PMID: 32282204 DOI: 10.1021/acs.jnatprod.9b00844
Abstract

Chemical investigation of cyanobacterial strain HT-58-2, which most closely aligns with the genus Brasilomena, has led to the isolation of two compounds related to tolypodiol. The structures and absolute configuration of 6-deoxytolypodiol (1) and 11-hydroxytolypodiol (2) were elucidated by spectroscopic and spectrometric analysis. While tolypodiol previously showed anti-inflammatory activity in a mouse ear edema assay, only 2 reduced in vitro thromboxane B2 and superoxide anion (O2-) generation from Escherichia coli lipopolysaccharide-activated rat neonatal microglia to any appreciable degree.