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Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer
The first chemical synthesis of the natural triterpenoid saponin Patrinia-glycoside B-II, namely oleanolic acid 3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-gluco-pyranosyl-(1→3)]-α-l-arabinopyranoside, has been accomplished in a linear 11-step sequence 11 with 9.4% overall yield. The abnormal (1)C(4) conform...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270016/ https://www.ncbi.nlm.nih.gov/pubmed/24335573 http://dx.doi.org/10.3390/molecules181215193 |
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author | Ren, Li Liu, Yong-Xiang Lv, Dan Yan, Mao-Cai Nie, Han Liu, Yang Cheng, Mao-Sheng |
author_facet | Ren, Li Liu, Yong-Xiang Lv, Dan Yan, Mao-Cai Nie, Han Liu, Yang Cheng, Mao-Sheng |
author_sort | Ren, Li |
collection | PubMed |
description | The first chemical synthesis of the natural triterpenoid saponin Patrinia-glycoside B-II, namely oleanolic acid 3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-gluco-pyranosyl-(1→3)]-α-l-arabinopyranoside, has been accomplished in a linear 11-step sequence 11 with 9.4% overall yield. The abnormal (1)C(4) conformation of the arabinose residue was found to occur via conformational fluctuation during preparation of the intermediates. Molecular mechanism and quantum chemistry calculations showed that Patrinia-glycoside B-II and its conformer 1 cannot interconvert under normal conditions. Preliminary structure-activity relationships studies indicated that the (4)C(1) chair conformation of the arabinose residue in the unique α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl disaccharide moiety is one of the chief positive factors responsible for its cytotoxic activity against tumors. |
format | Online Article Text |
id | pubmed-6270016 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62700162018-12-20 Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer Ren, Li Liu, Yong-Xiang Lv, Dan Yan, Mao-Cai Nie, Han Liu, Yang Cheng, Mao-Sheng Molecules Article The first chemical synthesis of the natural triterpenoid saponin Patrinia-glycoside B-II, namely oleanolic acid 3-O-α-l-rhamnopyranosyl-(1→2)-[β-d-gluco-pyranosyl-(1→3)]-α-l-arabinopyranoside, has been accomplished in a linear 11-step sequence 11 with 9.4% overall yield. The abnormal (1)C(4) conformation of the arabinose residue was found to occur via conformational fluctuation during preparation of the intermediates. Molecular mechanism and quantum chemistry calculations showed that Patrinia-glycoside B-II and its conformer 1 cannot interconvert under normal conditions. Preliminary structure-activity relationships studies indicated that the (4)C(1) chair conformation of the arabinose residue in the unique α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl disaccharide moiety is one of the chief positive factors responsible for its cytotoxic activity against tumors. MDPI 2013-12-10 /pmc/articles/PMC6270016/ /pubmed/24335573 http://dx.doi.org/10.3390/molecules181215193 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Ren, Li Liu, Yong-Xiang Lv, Dan Yan, Mao-Cai Nie, Han Liu, Yang Cheng, Mao-Sheng Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer |
title | Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer |
title_full | Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer |
title_fullStr | Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer |
title_full_unstemmed | Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer |
title_short | Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer |
title_sort | facile synthesis of the naturally cytotoxic triterpenoid saponin patrinia-glycoside b-ii and its conformer |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270016/ https://www.ncbi.nlm.nih.gov/pubmed/24335573 http://dx.doi.org/10.3390/molecules181215193 |
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