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Sesquiterpenes with new carbon skeletons from the basidiomycete Phlebia tremellosa

Three new sesquiterpenes, phlebidiol, phlebioic acid, and phlebiolide, as well as the known compound tremetriol, were isolated from cultures of the basidiomycete Phlebia tremellosa. The structures of all isolated compounds were established by extensive spectroscopic analyses, including those involvi...

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Autores principales: Nakashima, Ken-ichi, Tomida, Junko, Hirai, Takao, Kawamura, Yoshiaki, Inoue, Makoto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Singapore 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7188727/
https://www.ncbi.nlm.nih.gov/pubmed/30784001
http://dx.doi.org/10.1007/s11418-019-01286-8
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author Nakashima, Ken-ichi
Tomida, Junko
Hirai, Takao
Kawamura, Yoshiaki
Inoue, Makoto
author_facet Nakashima, Ken-ichi
Tomida, Junko
Hirai, Takao
Kawamura, Yoshiaki
Inoue, Makoto
author_sort Nakashima, Ken-ichi
collection PubMed
description Three new sesquiterpenes, phlebidiol, phlebioic acid, and phlebiolide, as well as the known compound tremetriol, were isolated from cultures of the basidiomycete Phlebia tremellosa. The structures of all isolated compounds were established by extensive spectroscopic analyses, including those involving extensive two-dimensional nuclear magnetic resonance. The absolute configurations of phlebidiol, phlebioic acid, and phlebiolide were determined by comparisons of experimental and calculated electronic circular dichroism spectra. Phlebidiol and phlebioic acid have previously unreported carbon skeletons, for which we propose the skeletal names “seco-sterpurane” and “phlebiane,” respectively. Phlebiolide is also the second published example of a merulane sesquiterpene. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s11418-019-01286-8) contains supplementary material, which is available to authorized users.
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spelling pubmed-71887272020-05-04 Sesquiterpenes with new carbon skeletons from the basidiomycete Phlebia tremellosa Nakashima, Ken-ichi Tomida, Junko Hirai, Takao Kawamura, Yoshiaki Inoue, Makoto J Nat Med Original Paper Three new sesquiterpenes, phlebidiol, phlebioic acid, and phlebiolide, as well as the known compound tremetriol, were isolated from cultures of the basidiomycete Phlebia tremellosa. The structures of all isolated compounds were established by extensive spectroscopic analyses, including those involving extensive two-dimensional nuclear magnetic resonance. The absolute configurations of phlebidiol, phlebioic acid, and phlebiolide were determined by comparisons of experimental and calculated electronic circular dichroism spectra. Phlebidiol and phlebioic acid have previously unreported carbon skeletons, for which we propose the skeletal names “seco-sterpurane” and “phlebiane,” respectively. Phlebiolide is also the second published example of a merulane sesquiterpene. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s11418-019-01286-8) contains supplementary material, which is available to authorized users. Springer Singapore 2019-02-19 2019 /pmc/articles/PMC7188727/ /pubmed/30784001 http://dx.doi.org/10.1007/s11418-019-01286-8 Text en © The Author(s) 2019, corrected publication 2020 Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Original Paper
Nakashima, Ken-ichi
Tomida, Junko
Hirai, Takao
Kawamura, Yoshiaki
Inoue, Makoto
Sesquiterpenes with new carbon skeletons from the basidiomycete Phlebia tremellosa
title Sesquiterpenes with new carbon skeletons from the basidiomycete Phlebia tremellosa
title_full Sesquiterpenes with new carbon skeletons from the basidiomycete Phlebia tremellosa
title_fullStr Sesquiterpenes with new carbon skeletons from the basidiomycete Phlebia tremellosa
title_full_unstemmed Sesquiterpenes with new carbon skeletons from the basidiomycete Phlebia tremellosa
title_short Sesquiterpenes with new carbon skeletons from the basidiomycete Phlebia tremellosa
title_sort sesquiterpenes with new carbon skeletons from the basidiomycete phlebia tremellosa
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7188727/
https://www.ncbi.nlm.nih.gov/pubmed/30784001
http://dx.doi.org/10.1007/s11418-019-01286-8
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