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Hyperacmosins K-M, three new polycyclic polyprenylated acylphloroglucinols from Hypericum acmosepalum.

ABSTRACT: Hyperacmosins K-M (1-3), three new polycyclic polyprenylated acylphloroglucinol (PPAPs) derivatives, were isolated from the air-dried aerial parts of Hypericum asmosepalum. Compounds 1 and 2 both possessed a rare 5,5-spiroketal subunit with the loss of C-2' carbonyl in the phloroglucinal ring, while compound 3 featured an unusual 1,2-seco-bicyclo[3.3.1] PPAP skeleton. Their structures were confirmed by NMR, HRESIMS, and CD spectra. The plausible biogenetic pathways of 1-3 were proposed, which gave an insight for future biomimetic synthesis of the novel compounds.

SUBMITTER: Sun M

PROVIDER: S-EPMC9034054 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Hyperacmosins K-M, three new polycyclic polyprenylated acylphloroglucinols from Hypericum acmosepalum.

Sun Mingxia M Wang Xue X Zhu Tingting T Suo Xinyue X Wang Jiajia J Ji Tengfei T Liu Bo B

RSC advances 20210614 34

Hyperacmosins K-M (1-3), three new polycyclic polyprenylated acylphloroglucinol (PPAPs) derivatives, were isolated from the air-dried aerial parts of Hypericum asmosepalum. Compounds 1 and 2 both possessed a rare 5,5-spiroketal subunit with the loss of C-2' carbonyl in the phloroglucinal ring, while compound 3 featured an unusual 1,2-seco-bicyclo[3.3.1] PPAP skeleton. Their structures were confirmed by NMR, HRESIMS, and CD spectra. The plausible biogenetic pathways of 1-3 were prop ...[more]

PMID: 35479371

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