Hyperacmosin R, a New Decarbonyl Prenylphloroglucinol with Unusual Spiroketal Subunit from Hypericum acmosepalum

Two previously undescribed polycyclic polyprenylated acylphloroglucinols, hyperacmosins R-S (1–2), were obtained from the aerial parts of Hypericum acmosepalum. Their structures were elucidated by extensive spectroscopic analysis and electronic circular dichroism calculation (ECD). Compound 1 featur...

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Autores principales: Ma, Yonghui, Liu, Xiaoyu, Liu, Bo, Li, Pingping, Suo, Xinyue, Zhu, Tingting, Ji, Tengfei, Li, Jin, Li, Xiaoxiu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9501122/
https://www.ncbi.nlm.nih.gov/pubmed/36144668
http://dx.doi.org/10.3390/molecules27185932
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author Ma, Yonghui
Liu, Xiaoyu
Liu, Bo
Li, Pingping
Suo, Xinyue
Zhu, Tingting
Ji, Tengfei
Li, Jin
Li, Xiaoxiu
author_facet Ma, Yonghui
Liu, Xiaoyu
Liu, Bo
Li, Pingping
Suo, Xinyue
Zhu, Tingting
Ji, Tengfei
Li, Jin
Li, Xiaoxiu
author_sort Ma, Yonghui
collection PubMed
description Two previously undescribed polycyclic polyprenylated acylphloroglucinols, hyperacmosins R-S (1–2), were obtained from the aerial parts of Hypericum acmosepalum. Their structures were elucidated by extensive spectroscopic analysis and electronic circular dichroism calculation (ECD). Compound 1 featured an unprecedented 5,8-spiroketal subunit as well as the loss of C-2′ carbonyl in the phloroglucinol ring. In addition, compounds 1 and 4 showed weak hepatoprotective activity against paracetamol-induced HepG2 cell damage at 10 μm. The plausible biosynthetic pathway of 1 was proposed via a retro-Clasisen reaction and decarboxylation.
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spelling pubmed-95011222022-09-24 Hyperacmosin R, a New Decarbonyl Prenylphloroglucinol with Unusual Spiroketal Subunit from Hypericum acmosepalum Ma, Yonghui Liu, Xiaoyu Liu, Bo Li, Pingping Suo, Xinyue Zhu, Tingting Ji, Tengfei Li, Jin Li, Xiaoxiu Molecules Article Two previously undescribed polycyclic polyprenylated acylphloroglucinols, hyperacmosins R-S (1–2), were obtained from the aerial parts of Hypericum acmosepalum. Their structures were elucidated by extensive spectroscopic analysis and electronic circular dichroism calculation (ECD). Compound 1 featured an unprecedented 5,8-spiroketal subunit as well as the loss of C-2′ carbonyl in the phloroglucinol ring. In addition, compounds 1 and 4 showed weak hepatoprotective activity against paracetamol-induced HepG2 cell damage at 10 μm. The plausible biosynthetic pathway of 1 was proposed via a retro-Clasisen reaction and decarboxylation. MDPI 2022-09-13 /pmc/articles/PMC9501122/ /pubmed/36144668 http://dx.doi.org/10.3390/molecules27185932 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Ma, Yonghui
Liu, Xiaoyu
Liu, Bo
Li, Pingping
Suo, Xinyue
Zhu, Tingting
Ji, Tengfei
Li, Jin
Li, Xiaoxiu
Hyperacmosin R, a New Decarbonyl Prenylphloroglucinol with Unusual Spiroketal Subunit from Hypericum acmosepalum
title Hyperacmosin R, a New Decarbonyl Prenylphloroglucinol with Unusual Spiroketal Subunit from Hypericum acmosepalum
title_full Hyperacmosin R, a New Decarbonyl Prenylphloroglucinol with Unusual Spiroketal Subunit from Hypericum acmosepalum
title_fullStr Hyperacmosin R, a New Decarbonyl Prenylphloroglucinol with Unusual Spiroketal Subunit from Hypericum acmosepalum
title_full_unstemmed Hyperacmosin R, a New Decarbonyl Prenylphloroglucinol with Unusual Spiroketal Subunit from Hypericum acmosepalum
title_short Hyperacmosin R, a New Decarbonyl Prenylphloroglucinol with Unusual Spiroketal Subunit from Hypericum acmosepalum
title_sort hyperacmosin r, a new decarbonyl prenylphloroglucinol with unusual spiroketal subunit from hypericum acmosepalum
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9501122/
https://www.ncbi.nlm.nih.gov/pubmed/36144668
http://dx.doi.org/10.3390/molecules27185932
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