Integrasone Derivatives Isolated from Lepteutypa sp. KT4162 and Their Anti-HIV‑1 Integrase Activity

Five integrasone derivatives, integrasone C (1), isointegrasone C (2), integrasone D1 (3), integrasone D2 (4), and integrasone E (5), were isolated from the culture broth of Lepteutypa sp. KT4162. Neither conventional NMR analyses nor DFT (density functional theory)-based computationally assisted ch...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2023-04, Vol.86 (4), p.1019-1024
Main Authors: Miura, Satomi, Ishida, Kotaro, Tanaka, Kazuaki, Morita, Eiji, Hashimoto, Masaru
Format: Article
Language:English
Subjects:
Bridged Bicyclo Compounds, Heterocyclic - pharmacology
Circular Dichroism
Furans - pharmacology
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism
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Summary:Five integrasone derivatives, integrasone C (1), isointegrasone C (2), integrasone D1 (3), integrasone D2 (4), and integrasone E (5), were isolated from the culture broth of Lepteutypa sp. KT4162. Neither conventional NMR analyses nor DFT (density functional theory)-based computationally assisted chemical shift discussions were sufficient to elucidate the relative configuration of the 1,4-epoxydiol moiety. A combined analysis using the calculated n J CH values and HMBC spectra was helpful to establish the relative configuration. The absolute configurations of 1–5 were determined using DFT-based ECD (electronic circular dichroism) spectral analysis. Biological assays of these compounds revealed that 2 potently inhibits HIV-1 integrase without cytotoxicity.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.3c00065