Identification of Anthelmintic Bishomoscalarane Sesterterpenes from the Australian Marine Sponge Phyllospongia bergquistae and Structure Revision of Phyllolactones A–D

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Hayes, Sasha
Taki, Aya C
Lum, Kah Yean
Byrne, Joseph J
White, Jonathan M
Ekins, Merrick G
Gasser, Robin B
Davis, Rohan A
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2022
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Abstract

High-throughput screening of the NatureBank marine extract library (7616 samples) identified an extract derived from the Australian marine sponge Phyllospongia bergquistae with activity against Hemonchus contortus (barber's pole worm), an economically important parasitic nematode. Bioassay-guided fractionation of the CH2Cl2/MeOH extract from P. bergquistae led to the purification of four known bishomoscalarane sesterterpenes, phyllolactones A-D (1-4). The absolute configurations of phyllolactones B (2) and C (3) were determined by single-crystal X-ray diffraction analysis; literature and data analyses revealed the need for these chemical structures to be revised. Compounds 2-4 induced a lethal, skinny (Ski) phenotype in larvae of H. contortus at concentrations between 5.3 and 10.1 μM. These data indicate that the bishomoscalarane sesterterpene structure class warrants further investigation for nematocidal or nematostatic activity.

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Journal of Natural Products

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85

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7

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This document is the Postprint: Accepted Manuscript version of a Published Work that appeared in final form in Journal of Natural Products, copyright 2022 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://doi.org/10.1021/acs.jnatprod.2c00229

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Analytical chemistry

Biological oceanography

Science & Technology

Life Sciences & Biomedicine

Plant Sciences

Chemistry, Medicinal

Pharmacology & Pharmacy

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Hayes, S; Taki, AC; Lum, KY; Byrne, JJ; White, JM; Ekins, MG; Gasser, RB; Davis, RA,Identification of Anthelmintic Bishomoscalarane Sesterterpenes from the Australian Marine Sponge Phyllospongia bergquistae and Structure Revision of Phyllolactones A–D, Journal of Natural Products, 2022, 85 (7), pp. 1723-1729

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