Holophyllane A: A Triterpenoid Possessing an Unprecedented B-nor-3,4-seco-17,14-friedo-lanostane Architecture from Abies holophylla

A novel triterpenoid, holophyllane A (1), featuring a B-nor-3,4-seco-17,14-friedo-lanostane, along with its putative precursor, compound 2 were isolated from the methanol extract of the trunks of Abies holophylla. The 2D structure and relative configuration of 1 were initially determined via analysi...

Descripción completa

Detalles Bibliográficos
Autores principales: Kim, Chung Sub, Oh, Joonseok, Subedi, Lalita, Kim, Sun Yeou, Choi, Sang Un, Lee, Kang Ro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5333622/
https://www.ncbi.nlm.nih.gov/pubmed/28252664
http://dx.doi.org/10.1038/srep43646
_version_ 1782511743944097792
author Kim, Chung Sub
Oh, Joonseok
Subedi, Lalita
Kim, Sun Yeou
Choi, Sang Un
Lee, Kang Ro
author_facet Kim, Chung Sub
Oh, Joonseok
Subedi, Lalita
Kim, Sun Yeou
Choi, Sang Un
Lee, Kang Ro
author_sort Kim, Chung Sub
collection PubMed
description A novel triterpenoid, holophyllane A (1), featuring a B-nor-3,4-seco-17,14-friedo-lanostane, along with its putative precursor, compound 2 were isolated from the methanol extract of the trunks of Abies holophylla. The 2D structure and relative configuration of 1 were initially determined via analysis of 1D and 2D NMR spectroscopic data and the assignment was confirmed by quantum mechanics-based NMR chemical shift calculations. The absolute configuration was established by comparison of the experimental and simulated ECD data generated at different theory levels. Compounds 1 and 2 exhibited moderate to weak cytotoxicity and significant inhibitory activity against nitric oxide (NO) production.
format Online
Article
Text
id pubmed-5333622
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher Nature Publishing Group
record_format MEDLINE/PubMed
spelling pubmed-53336222017-03-06 Holophyllane A: A Triterpenoid Possessing an Unprecedented B-nor-3,4-seco-17,14-friedo-lanostane Architecture from Abies holophylla Kim, Chung Sub Oh, Joonseok Subedi, Lalita Kim, Sun Yeou Choi, Sang Un Lee, Kang Ro Sci Rep Article A novel triterpenoid, holophyllane A (1), featuring a B-nor-3,4-seco-17,14-friedo-lanostane, along with its putative precursor, compound 2 were isolated from the methanol extract of the trunks of Abies holophylla. The 2D structure and relative configuration of 1 were initially determined via analysis of 1D and 2D NMR spectroscopic data and the assignment was confirmed by quantum mechanics-based NMR chemical shift calculations. The absolute configuration was established by comparison of the experimental and simulated ECD data generated at different theory levels. Compounds 1 and 2 exhibited moderate to weak cytotoxicity and significant inhibitory activity against nitric oxide (NO) production. Nature Publishing Group 2017-03-02 /pmc/articles/PMC5333622/ /pubmed/28252664 http://dx.doi.org/10.1038/srep43646 Text en Copyright © 2017, The Author(s) http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Kim, Chung Sub
Oh, Joonseok
Subedi, Lalita
Kim, Sun Yeou
Choi, Sang Un
Lee, Kang Ro
Holophyllane A: A Triterpenoid Possessing an Unprecedented B-nor-3,4-seco-17,14-friedo-lanostane Architecture from Abies holophylla
title Holophyllane A: A Triterpenoid Possessing an Unprecedented B-nor-3,4-seco-17,14-friedo-lanostane Architecture from Abies holophylla
title_full Holophyllane A: A Triterpenoid Possessing an Unprecedented B-nor-3,4-seco-17,14-friedo-lanostane Architecture from Abies holophylla
title_fullStr Holophyllane A: A Triterpenoid Possessing an Unprecedented B-nor-3,4-seco-17,14-friedo-lanostane Architecture from Abies holophylla
title_full_unstemmed Holophyllane A: A Triterpenoid Possessing an Unprecedented B-nor-3,4-seco-17,14-friedo-lanostane Architecture from Abies holophylla
title_short Holophyllane A: A Triterpenoid Possessing an Unprecedented B-nor-3,4-seco-17,14-friedo-lanostane Architecture from Abies holophylla
title_sort holophyllane a: a triterpenoid possessing an unprecedented b-nor-3,4-seco-17,14-friedo-lanostane architecture from abies holophylla
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5333622/
https://www.ncbi.nlm.nih.gov/pubmed/28252664
http://dx.doi.org/10.1038/srep43646
work_keys_str_mv AT kimchungsub holophyllaneaatriterpenoidpossessinganunprecedentedbnor34seco1714friedolanostanearchitecturefromabiesholophylla
AT ohjoonseok holophyllaneaatriterpenoidpossessinganunprecedentedbnor34seco1714friedolanostanearchitecturefromabiesholophylla
AT subedilalita holophyllaneaatriterpenoidpossessinganunprecedentedbnor34seco1714friedolanostanearchitecturefromabiesholophylla
AT kimsunyeou holophyllaneaatriterpenoidpossessinganunprecedentedbnor34seco1714friedolanostanearchitecturefromabiesholophylla
AT choisangun holophyllaneaatriterpenoidpossessinganunprecedentedbnor34seco1714friedolanostanearchitecturefromabiesholophylla
AT leekangro holophyllaneaatriterpenoidpossessinganunprecedentedbnor34seco1714friedolanostanearchitecturefromabiesholophylla

Ejemplares similares