Antifungal bromopyrrole alkaloids from the South China Sea sponge Agelas sp.

Yan Zhu, Yan Wang, Bin-Bin Gu, Fan Yang, Wei-Hua Jiao, Gan-Hai Hu, Hao-Bing Yu, Bing-Nan Han, Wei Zhang, Yang Shen, Hou-Wen Lin

    Research output: Contribution to journalArticlepeer-review

    18 Citations (Scopus)

    Abstract

    Six new bromopyrrole alkaloids, longamides D-F (1-3), 3-oxethyl-4-[1-(4,5-dibromopyrrole-2-yl)-formamido]-butanoic acid methyl ester (4), 2-oxethyl-3-[1-(4,5-dibromopyrrole-2-yl)-formamido]-methyl propionate (5), and 9-oxethyl-mukanadin F (6), along with two known metabolites, hanishin (7) and longamide B methyl ester (8), were isolated from the South China Sea sponge Agelas sp. The racemic mixtures 1-5, 7 and 8 were resolved into seven pairs of enantiomers 1a/1b-5a/5b, 7a/7b, and 8a/8b through HPLC using a Chiralcel OJ-RH column. The structures were elucidated on the basis of spectroscopic data. The absolute configurations of each enantiomer of (±)-1 and (±)-2 were established through the quantum mechanical calculations of the corresponding electronic circular dichroism (ECD) spectra and using the CD exciton chirality method, respectively, whereas the absolute configurations of 3a and 3b were confirmed by comparing the experimental CD spectra with that of (-)-S-longamide B methyl ester. Individual enantiomers (+)-(9S, 10R)-1a, (-)-S-2b, (+)-R-3a, (+)-R-7a, and (+)-R-8a exhibited effective antifungal activity against Candida albicans in a Caenorhabditis elegans candidiasis model.

    Original languageEnglish
    Pages (from-to)2964-2971
    Number of pages8
    JournalTetrahedron
    Volume72
    Issue number22
    DOIs
    Publication statusPublished - 2 Jun 2016

    Keywords

    • Antifungal
    • Bromopyrrole alkaloids
    • Enantiomers
    • Marine sponges
    • Nematodes

    Fingerprint Dive into the research topics of 'Antifungal bromopyrrole alkaloids from the South China Sea sponge Agelas sp.'. Together they form a unique fingerprint.

    Cite this