Solving the supply of Resveratrol Tetramers from Papua New Guinean rainforest Anisoptera species (Dipterocarpaceae) that inhibit bacterial type III secretion systems

Article

Davis, Rohan A., Beattie, Karren D., Xu, Min, Yang, Xinzhou, Yin, Sheng, Holla, Harish, Healy, Peter C., Sykes, Melissa, Shelper, Todd, Avery, Vicky M., Elofsson, Mikael, Sundin, Charlotta and Quinn, Ronald. 2014. "Solving the supply of Resveratrol Tetramers from Papua New Guinean rainforest Anisoptera species (Dipterocarpaceae) that inhibit bacterial type III secretion systems." Journal of Natural Products. 77 (12), pp. 2633-2640. https://doi.org/10.1021/np500433z
Article Title

Solving the supply of Resveratrol Tetramers from Papua New Guinean rainforest Anisoptera species (Dipterocarpaceae) that inhibit bacterial type III secretion systems

ERA Journal ID40471
Article CategoryArticle
AuthorsDavis, Rohan A. (Author), Beattie, Karren D. (Author), Xu, Min (Author), Yang, Xinzhou (Author), Yin, Sheng (Author), Holla, Harish (Author), Healy, Peter C. (Author), Sykes, Melissa (Author), Shelper, Todd (Author), Avery, Vicky M. (Author), Elofsson, Mikael (Author), Sundin, Charlotta (Author) and Quinn, Ronald (Author)
Journal TitleJournal of Natural Products
Journal Citation77 (12), pp. 2633-2640
Number of Pages8
Year2014
Place of PublicationWashington, DC. United States
ISSN0163-3864
1520-6025
Digital Object Identifier (DOI)https://doi.org/10.1021/np500433z
Abstract

The supply of (–)-hopeaphenol was achieved via enzymatic biotransformation in order to provide material for pre-clinical investigation. High-throughput screening of a pre-fractionated natural product library aimed to identify compounds that inhibit the bacterial virulence type III secretion system (T3SS) identified several fractions derived from two Papua New Guinean Anisoptera species, showing activity against Yersinia pseudotuberculosis outer proteins E and H (YopE and YopH). Bioassay-directed isolation from the leaves of A. thurifera, and similarly A. polyandra, resulted in three known resveratrol tetramers, (–)-hopeaphenol (1), vatalbinoside A (2) and vaticanol B (3). Compounds 1–3 displayed IC50 values of 8.8, 12.5 and 9.9 M in the reporter-gene assay, and IC50 values of 2.9, 4.5 and 3.3 M in the YopH assay, respectively, which suggested that they could potentially act against the T3SS in Yersinia. The structures of 1-3 were confirmed through a combination of spectrometric, chemical methods and single crystal X-ray structure determinations of the natural product 1 and the permethyl ether analogue of 3. The enzymatic hydrolysis of the β-glycoside 2 to the aglycone 1 was achieved through biotransformation using the endogenous leaf enzymes, this significantly enhanced the yield of the desired bioactive natural product from 0.08% to 1.3% and facilitates ADMET studies of (–)-hopeaphenol (1).

Keywordsresveratrol; Anisoptera; hopeaphenol; enzymatic hydrolysis; T3SS inhibitors; anti-infectives
ANZSRC Field of Research 2020321402. Clinical pharmacology and therapeutics
340401. Biologically active molecules
340502. Natural products and bioactive compounds
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Byline AffiliationsGriffith University
Umea University, Sweden
Institution of OriginUniversity of Southern Queensland
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