Chemical constituents from the stem of <i>Callerya nitida Benth.</i>var<i>.hirsutissima </i>Z.Wei

JIN Chen; HUANG Huilian; HE Yuqin; ZHANG Ling

doi:10.11665/j.issn.1000-5048.20210206

Journal of China Pharmaceutical University > 2021 > 52(2): 177-185. > DOI: 10.11665/j.issn.1000-5048.20210206

JIN Chen, HUANG Huilian, HE Yuqin, ZHANG Ling. Chemical constituents from the stem of Callerya nitida Benth.var.hirsutissima Z.Wei[J]. Journal of China Pharmaceutical University, 2021, 52(2): 177-185. DOI: 10.11665/j.issn.1000-5048.20210206

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Chemical constituents from the stem of Callerya nitida Benth.var.hirsutissima Z.Wei

1.
Jiangxi University of Chinese Medicine, Nanchang 330004
2.
School of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, China

Funds: This study was supported by the National Natural Science Foundation of China (No.81960697,No.81460595) and the Funded Project of First-Class Discipline of Traditional Chinese Pharmacy in Jiangxi Province (No.JXSYLXK-ZHYA0073)

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Received Date: September 24, 2020
Revised Date: April 02, 2021

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Abstract

Abstract

The chemical constituents from 70% ethanol petroleum ether and n-butanol extractions of Callerya nitita Benth.var.hirsutissima.Z.Wei. were separated by preparative high-performance liquid chromatographic techniques, including repeated column chromatography over macroporous adsorption resin, silica gel, ODS, Sephadex LH-20. The structures of the compounds were identified by their physicochemical properties, spectral data, and mass spectrometry data, in comparison with literature. In our research, one triterpenoids, taraxerone (1), and twenty flavonoids, including genistein-4′-O-β-glucoside (2), 5-hydroxy-4′-methoxyisoflavone-7-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (3), biochanin A 7-O-β-D-apiofuranosyl-(1→5)-β-D-apiofuranosyl- (1→6)-β-D-glucopyranoside (4), formononetin-7-O-β-D-galactopyranoside (5), 5,7-dihydroxy-3′,4′-dimethoxyisoflavone (6), biochanin A-7-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside (7), 5, 7-dihydroxyisoflavone-4′-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside (8), formononetin-7-O-D-apio-β-D-furanosyl(l→2)-β-D-glucopyranoside (9), 4′-hydroxy-3′-methoxyisoflavone-7-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (10), prunetin (11), prunetin 4′-O-β-D-glucopyranoside (12), pratensein7-O-β-D-glucoside (13), 8-methoxyisoformononetin (14), genistein (15), 3′-hydroxybiochanin A (16), biochanin A (17), 5,7-dihydroxy-3′,5′-dimethoxyisoflavone (18), ononin (19), isoformononetin (20), 5,7,3′,4′-tetrahydroxyflavone (21) were isolated from the two extract parts.Compounds 1-10, 12-14, 16-18, 20 were obtained from this plant, and it is the first time to investigate the plant for the first time.
- Callerya,
- Callerya nitida Benth.var.hirsutissima Z.Wei.,
- chemical constituents,
- petroleum ether extract,
- n-butanol extract

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References (28)

References

[1]	.Beijing： Ministry of Health of the People′s Republic of China， 1995： 81.
[2]	Health Department of Jiangxi Province. Standards for Traditional Chinese Medicines in Jiangxi Province［S］.Nanchang： Health Department of Jiangxi Province，2014： 46-48.
[3]	Food and Drug Administration of Hunan Province.Standards for Traditional Chinese Medicines in Hunan Province［S］.Changsha： Food and Drug Administration of Hunan Province，2009： 34-35.
[4]	Xiong Y， Jin C， Cao L， et al.Research progress on the medicinal resources of the genus Millettia in China［J］.J Chin Med Mater（中药材）， 2020， 43（4）： 1015-1022.
[5]	Yu WW， Jin C， Shuang PC， et al.Isoflavones and flavans from Millettia nitida var. hirsutissima［J］.Chin J Chin Mater Med（中国中药杂志）， 2015， 40（12）： 2363-2366.
[6]	He YQ， Jin C， Huang B， et al.Isolation and identification of chemical constituents from Millettla nitida var．hirsutissima［J］.Chin J Exp Tradit Med Formulae（中国实验方剂学杂志）， 2018， 24（2）： 51-56.
[7]	Xu J， Deng ZW， Lin WH， et al.Chemical constituents of mangrove plant Excoecaria agallocha in Hainan Province［J］.Chin Tradit Herb Drugs（中草药）， 2009， 40（11）： 1704-1707.
[8]	Liu XH， Wang CH， Chou GX， et al. Flavonoids of Desmodium micropjyllum［J］.Nat Prod Res Dev（天然产物研究与开发）， 2010， 22（6）： 976-978， 1008.
[9]	Li X， Li JF， Wang D， et al.Isoflavone glycosides from the bark of Maackia amurensis［J］.Acta Pharm Sin（药学学报）， 2009， 44（1）： 63-68.
[10]	Farag SF， Ahmed AS， Terashima K， et al. Isoflavonoid glycosides from Dalbergia sissoo［J］. Phytochemistry， 2001， 57（8）： 1263-1268.
[11]	Drenin AA， Botirov EK， Petrulyak EV.Two new isoflavlnoid monogalactosides from Trifolium pratense roots［J］.Chem Nat Compd， 2008， 44（1）： 24-27.
[12]	Hosny M， Rosazza JPN. Microbial hydroxylation and methylation of genistein by streptomycetes［J］. J Nat Prod， 1999， 62（12）： 1609-1612.
[13]	Djouossi MG， Mabou FD， Foning Tebou PL， et al.Chevalierinoside B and C： two new isoflavonoid glycosides from the stem bark of Antidesma laciniatum Muell. Arg （syn. Antidesma chevalieri Beille）［J］. Phytochem Lett， 2014， 9： 149-152.
[14]	Tang YP， Lou FC， Ma W， et al. Isoflavonoid glycosides from the pericarps of Sophora japonica［J］.J China Pharm Univ（中国药科大学学报）， 2001， 32（3）： 187-189.
[15]	Liu Q， Liu YR. Chemical composition research of Glycyrrhiza eurycarpa P.C.Li［J］.Acta Pharm Sin（药学学报）， 1989， 24（7）： 525-531.
[16]	Shen Y， Feng Z， Jiang J， et al. Dibenzoyl and isoflavonoid glycosides from Sophora flavescens： inhibition of the cytotoxic effect of D-Galactosamine on human hepatocyte HL-7702 ［J］. J Nat Prod， 2013， 76（12）： 2337-2345.
[17]	Liu YM， Jiang BP， Shen SN， et al. Chemical constituents from leaves of Cajanus cajan［J］.Chin Tradit Herb Drugs（中草药）， 2014， 45（4）： 466-470.
[18]	Drenin AA， Botirov EK， Turov YP. Anew isoflavone glycoside from Trifolium pratense L.［J］. Russ J Bioorg Chem， 2011， 37（7）： 862-865.
[19]	Ma XF， Tian XM， Chen YJ， et al.Flavonoid constituents of Astragalus membranaceus var. mongholicus［J］.Chin Tradit Herb Drugs（中草药）， 2005， 36（9）： 1293-1296.
[20]	Fodja Saah EP， Sielinou VT， Kuete V， et al. Antimicrobial and antioxidant isoflavonoid derivatives from the roots of Amphimas pterocarpoides［J］.Z. Naturforsch B， 2013， 68（b）： 931-938.
[21]	Ji WL，Qin MJ，Wang ZT.Studies on the constituents of Belamcanda chinensis（Ⅰ）［J］.J China Pharm Univ（中国药科大学学报）， 2001， 32（3）： 197-199.
[22]	Han LF， Zhao J， Zhang Y， et al. Chemical constituents from dried aerial parts of Eclipta prostrata［J］. Chin Herb Med， 2013， 5（4）： 313-316.
[23]	Chen HQ， Jin ZY.Isolation， purification and structure identification of isoflavones from Trifolium pratense L.［J］.Chin Tradit Herb Drugs（中草药）， 2006（11）： 1629-1631.
[24]	Shen H， Sun J， Zhao PJ， et al. Cytotoxic metabolites from the roots of ranunculus ternatus［J］. Chem Nat Compd， 2014， 50（4）： 621-623.
[25]	Wang Q， Miao WJ， Xiang C， et al. Chemical constituents in flavonoids from root of Glycyrrhiza uralensis［J］.Chin Tradit Herb Drugs（中草药）， 2014， 45（1）： 31-36.
[26]	Liao H， Zhang L， Jin C， et al. Chemical components from Millettia nitita var．hirsutissima［J］.Chin J Exp Tradit Med Formulae（中国实验方剂学杂志）， 2017， 23（16）： 62-67.
[27]	Jiang KW， Pan B， Tian B. Recent taxonomic changes for Fabaceae （Leguminosae） genera in China［J］.Bio Sci（生物多样性）， 2019， 27（6）： 689-697.
[28]	Xia Q， Wang WY， Tu TY， et al. Pollen morphology of Callerya Endl. and Millettia Wight et Arn. （Leguminosae） from China and its systematic implications［J］.J Trop Subtrop Bot（热带亚热带植物学报）， 2018， 26（5）： 529-537.

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