Bioactive Triterpenoid Saponins From the Seeds of Aesculus chinensis Bge. var. chekiangensis

Phytochemical investigation of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang obtained 33 triterpenoid saponins, including 14 new ones, aesculiside C–P (1–14). The structure elucidations were performed through comprehensive MS, 1D and 2D-NMR analysis, and their absolute configuration w...

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Main Authors: Nan Zhang, Shuxiang Wei, Shijie Cao, Qiang Zhang, Ning Kang, Liqin Ding, Feng Qiu
Format: Article
Language:English
Published: Frontiers Media S.A. 2020-01-01
Series:Frontiers in Chemistry
Subjects:
Online Access:https://www.frontiersin.org/article/10.3389/fchem.2019.00908/full
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spelling doaj-bfcbbb58600f419aa96d3671fd50feed2020-11-25T02:19:42ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462020-01-01710.3389/fchem.2019.00908507054Bioactive Triterpenoid Saponins From the Seeds of Aesculus chinensis Bge. var. chekiangensisNan Zhang0Nan Zhang1Shuxiang Wei2Shuxiang Wei3Shijie Cao4Shijie Cao5Qiang Zhang6Qiang Zhang7Ning Kang8Ning Kang9Liqin Ding10Feng Qiu11Feng Qiu12School of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaTianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaSchool of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaTianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaSchool of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaTianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaSchool of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaTianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaSchool of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaTianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaTianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaSchool of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaTianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin, ChinaPhytochemical investigation of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang obtained 33 triterpenoid saponins, including 14 new ones, aesculiside C–P (1–14). The structure elucidations were performed through comprehensive MS, 1D and 2D-NMR analysis, and their absolute configuration was unambiguously determined by X-ray diffraction analysis as well as Mo2(OAc)4-induced ECD method for the first time. All the substances were examined for their cytotoxic activities against three tumor cell lines, Hep G2, HCT-116, and MGC-803. Of these, compounds 8, 9, 14–16, 18, and 22 exhibited potent cytotoxicities against all cell lines with IC50 of 2–21 μM, while compounds 3, 6, 7, 17–19, 20, 24, and 28 depicted moderate activity (IC50 13 to >40 μM). On these bases, the preliminary structure-activity correlations were also discussed. Meanwhile the neuroprotective properties of triterpenoid saponins from Aesculus genus were evaluated for the first time. Among them, compounds 1, 4, 12, 20, 22, 25, 29, and 31 exhibited moderate activities against COCl2-induced PC12 cell injury.https://www.frontiersin.org/article/10.3389/fchem.2019.00908/fullAesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fangphytochemistrytriterpenoid saponinscytotoxic activitiesneuroprotective activities
collection DOAJ
language English
format Article
sources DOAJ
author Nan Zhang
Nan Zhang
Shuxiang Wei
Shuxiang Wei
Shijie Cao
Shijie Cao
Qiang Zhang
Qiang Zhang
Ning Kang
Ning Kang
Liqin Ding
Feng Qiu
Feng Qiu
spellingShingle Nan Zhang
Nan Zhang
Shuxiang Wei
Shuxiang Wei
Shijie Cao
Shijie Cao
Qiang Zhang
Qiang Zhang
Ning Kang
Ning Kang
Liqin Ding
Feng Qiu
Feng Qiu
Bioactive Triterpenoid Saponins From the Seeds of Aesculus chinensis Bge. var. chekiangensis
Frontiers in Chemistry
Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang
phytochemistry
triterpenoid saponins
cytotoxic activities
neuroprotective activities
author_facet Nan Zhang
Nan Zhang
Shuxiang Wei
Shuxiang Wei
Shijie Cao
Shijie Cao
Qiang Zhang
Qiang Zhang
Ning Kang
Ning Kang
Liqin Ding
Feng Qiu
Feng Qiu
author_sort Nan Zhang
title Bioactive Triterpenoid Saponins From the Seeds of Aesculus chinensis Bge. var. chekiangensis
title_short Bioactive Triterpenoid Saponins From the Seeds of Aesculus chinensis Bge. var. chekiangensis
title_full Bioactive Triterpenoid Saponins From the Seeds of Aesculus chinensis Bge. var. chekiangensis
title_fullStr Bioactive Triterpenoid Saponins From the Seeds of Aesculus chinensis Bge. var. chekiangensis
title_full_unstemmed Bioactive Triterpenoid Saponins From the Seeds of Aesculus chinensis Bge. var. chekiangensis
title_sort bioactive triterpenoid saponins from the seeds of aesculus chinensis bge. var. chekiangensis
publisher Frontiers Media S.A.
series Frontiers in Chemistry
issn 2296-2646
publishDate 2020-01-01
description Phytochemical investigation of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang obtained 33 triterpenoid saponins, including 14 new ones, aesculiside C–P (1–14). The structure elucidations were performed through comprehensive MS, 1D and 2D-NMR analysis, and their absolute configuration was unambiguously determined by X-ray diffraction analysis as well as Mo2(OAc)4-induced ECD method for the first time. All the substances were examined for their cytotoxic activities against three tumor cell lines, Hep G2, HCT-116, and MGC-803. Of these, compounds 8, 9, 14–16, 18, and 22 exhibited potent cytotoxicities against all cell lines with IC50 of 2–21 μM, while compounds 3, 6, 7, 17–19, 20, 24, and 28 depicted moderate activity (IC50 13 to >40 μM). On these bases, the preliminary structure-activity correlations were also discussed. Meanwhile the neuroprotective properties of triterpenoid saponins from Aesculus genus were evaluated for the first time. Among them, compounds 1, 4, 12, 20, 22, 25, 29, and 31 exhibited moderate activities against COCl2-induced PC12 cell injury.
topic Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang
phytochemistry
triterpenoid saponins
cytotoxic activities
neuroprotective activities
url https://www.frontiersin.org/article/10.3389/fchem.2019.00908/full
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