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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...

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Autores principales: Ren, Li, Liu, Yong-Xiang, Lv, Dan, Yan, Mao-Cai, Nie, Han, Liu, Yang, Cheng, Mao-Sheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
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.
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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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