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Neopetrothiazide: An Intriguing Pentacyclic Thiazide Alkaloid from the Sponge Neopetrosia sp.

ABSTRACT: Neopetrothiazide (1), a pentacyclic isoquinoline quinone, was isolated from a Neopetrosia sp. sponge. The structure elucidation was facilitated by utilizing long-range heteronuclear single quantum multiple bond correlation (LR-HSQMBC) and heteronuclear multiple bond correlation (HMBC) nuclear magnetic resonance (NMR) pulse sequences optimized to detect four- and five-bond ¹H-¹³C heteronuclear correlations. These NMR experiments can help assign proton-deficient structural motifs like neopetrothiazide (1), which has 14 contiguous nonprotonated centers (C, N, and S). Neopetrothiazide (1), with an unprecedented thiazide-fused structural scaffold, is the first natural product containing a thiazide moiety.

SUBMITTER: Wang D

PROVIDER: S-EPMC9341131 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Neopetrothiazide: An Intriguing Pentacyclic Thiazide Alkaloid from the Sponge Neopetrosia sp.

Wang Dongdong D Jiang Wei W Kim Chang-Kwon CK Bokesch Heidi R HR Woldemichael Girma M GM Gryder Berkley E BE Shern John F JF Khan Javed J O'Keefe Barry R BR Beutler John A JA Gustafson Kirk R KR

Organic letters 20210413 9

Neopetrothiazide (1), a pentacyclic isoquinoline quinone, was isolated from a Neopetrosia sp. sponge. The structure elucidation was facilitated by utilizing long-range heteronuclear single quantum multiple bond correlation (LR-HSQMBC) and heteronuclear multiple bond correlation (HMBC) nuclear magnetic resonance (NMR) pulse sequences optimized to detect four- and five-bond 1H-13C heteronuclear correlations. These NMR experiments can help assign proton-deficient ...[more]

PMID: 33848174

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