Alkaloids from the Chinese Vine Gnetum montanum

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Martin, Frederic
Grkovic, Tanja
Sykes, Melissa L
Shelper, Todd
Avery, Vicky M
Camp, David
Quinn, Ronald J
Davis, Rohan A
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2011
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Abstract

During a high-throughput screening campaign of a prefractionated natural product library, fractions from the Chinese vine Gnetum montanum showed in vitro activity against Pseudomonas aeruginosa wild-type strain, PAO1. UV-directed isolation of the organic extract from the vine leaves resulted in the purification of the new natural products N-methyllaudanosolinium trifluoroacetate (1), 3′-hydroxy-N,N-dimethylcoclaurinium trifluoroacetate (2), 1,9,10-trihydroxy-2-methoxy-6-methylaporphinium trifluoroacetate (3), and 6a,7-didehydro-1,9,10-trihydroxy-2-methoxy-6-methylaporphinium trifluoroacetate (4). Compound 4 is described here for the first time, and this is the first report of compounds 1–3 as natural products. Compounds 1–3 were found to racemize over time. Starting from commercially available (+)-boldine, through a series of semisynthetic reactions, a mechanism for the racemization of the isolated compounds is proposed. The known natural products (−)-latifolian A (5) and magnocurarine (6) were also isolated during these studies. The antibacterial activity was explained by the presence of 5, which displayed an IC50 value of 9.8 μM (MIC = 35 μM).

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Journal of Natural Products

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74

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11

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This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Natural Products, copyright 2011 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/np200700f

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Chemical sciences

Medicinal and biomolecular chemistry not elsewhere classified

Biological sciences

Biomedical and clinical sciences

Traditional, complementary and integrative medicine

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