Objective: To study the antihyperlipidemia effective constituent of Polygala fallax Hemsl.
Method: Column chromatographic techniques were employed for isolation and purification of chemical constituents of the plant and the structures were elucidated by IR, NMR and MS spectroscopy.
Result: Four triterpenoid saponins were isolated and determined as 3-O-beta-D-glucopyranosyl-( 1--> 2) -beta-D-glucopyranosyl presenegenin 28-O-beta-D-xylopyranosyl-(1-->4 ) -alpha-L-rhamnopyranosyl-(1-->2 ) -beta-D-fucopyranosyl ester (I), 3-O-beta-D-glucopyranosyl-(1-->2) -beta-D-glucopyranosyl presenegenin 28-O-beta-D-xylopyranosyl-(1-->4) -alpha-L-rhamnopyranosyl-(1-->2) -(3-O-acetyl)-beta-D-fucopyranosyl ester (II), 3-O-beta-D-glucopyranosyl-(1-->2) -beta-D-glucopyranosyl presenegenin 28-O-beta-D-xylopyranosyl-(1-->4) -alpha-L-rhamnopyranosyl-(1-->2) -(4-O-acetyl) -beta-D-fucopyranosyl ester (II) and 3-O-beta-D-glucopyranosyl-(1--2) -beta-D-glucopyranosyl presenegenin 28-O-beta-D-xylopyranosyl-(1-->4 ) -alpha-L-rhamnopyranosyl-(1-->2 ) - (3,4-diacetyl) -beta-D-fucopyranosyl ester (IV).
Conclusions: The effective constituents of Polygala fallax Hemsl. reduced blood lipid especially plasma TG markedly. The authors have studied the chemical constituents of effective constituent systematically for the first time.
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Zhongguo Zhong Yao Za Zhi
July 2015
Seven acylated triterpene saponins were isolated from the roots of Securidaca inappendiculata by means of various chromatographic techniques such as silica gel, MPLC, preparative HPLC, and semi-preparative HPLC. Their chemical structures were identified as securioside A(1), securioside B(2), 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1-->4)-α-L-rhamnopyranosyl-(1-->2)-[β-D-glucopyranosyl-(1-->3)]-4-O-[(E)-3,4-dimethoxycinnamoyl]-β-D-fucopyranosyl ester(3), 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1-->4)-α-L-rhamnopyranosyl-(1-->2)-[β-D-glucopyranosyl-(1-->3) ] -4-O-[(E/Z)-3, 4-dimethoxycinnamoyl]-β-D-fucopyranosyl ester(3/4), 3-O-β-D-glucopyranosyl presenegenin 28-O-α-L-arabinopyranosyl-(1-->3)-β-D-xylopyranosyl-(1-->4)-α-L-rhamnopyranosyl-(1-->2)-4-O-[(E)-3,4-dimethoxycinnamoyl]-β-D-fucopyranosyl ester(5), polygalasa- ponin XLV(6), and polygalasaponin XLVI (7) on the basis of spectroscopic data analysis and physicochemical properties. Among them, compounds 5-7 were isolated from the plants in genus Securidaca for the first time and compounds 3, 3/4 were isolated from the species for the first time.
View Article and Find Full Text PDFJ Asian Nat Prod Res
November 2008
Department of Traditional Chinese Medicine Chemistry, School of Traditional Chinese Medicine, Beijing University of Chinese Medicine, Beijing, China.
A new triterpenoid saponin, tenuifoside A, was isolated together with three known triterpenoid saponins 2, 3, and 4 from the roots of Polygala tenuifolia Willd. With the help of chemical and spectral analyses (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new saponin was elucidated as 3-O-beta-d-glucopyranosyl presenegenin 28-O-beta-d-xylopyranosyl-(1 --> 3)-beta-d-xylopyranosyl-(1 --> 4)-[beta-D-apiofuranosyl-(1 --> 3)]-alpha-L-rhamnopyranosyl-(1 --> 2)-[4-O-p-methoxycinnamoyl]-[alpha-l-rhamnopyranosyl-(1 --> 3)]-beta-d-fucopyranosyl ester (1). Three known triterpenoid saponins (2-4) were identified on the basis of spectroscopic data.
View Article and Find Full Text PDFPhytochemistry
May 2008
Institute of Materia Medica, Chinese Academy of Medical Sciences and Key Laboratory of Bioactive Substances and Resources Utilization of Chinese, Herbal Medicine (Peking Union Medical College), Ministry of Education, Beijing, China.
An oligosaccharide polyester, 1-O-(E)-p-coumaroyl-(3-O-benzoyl)-beta-D-fructofuranosyl-(2-->1)-[6-O-(E)-feruloyl-beta-D-glucopyranosyl-(1-->2)]-[6-O-acetyl-beta-D-glucopyranosyl-(1-->3)-(4-O-acetyl)-beta-D-glucopyranosyl-(1-->3)]-4-O-[4-O-alpha-L-rhamnopyranosyl-(E)-p-coumaroyl]-alpha-D-glucopyranoside (polygalajaponicose I), and four triterpenoid saponins, 3beta, 23, 27-trihydroxy-29-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-olean-12-en-28-oic acid (polygalasaponin XLVII), 3-O-beta-D-glucopyranosyl presenegenin 28-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranosyl ester (polygalasaponin XLVIII), 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-galactopyranosyl-(1-->5)-beta-D-apiofuranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester (polygalasaponin XLIX) and 2beta, 27-dihydroxy-3-O-beta-D-glucopyranosyl 11-oxo-olean-12-en-23, 28-dioic acid 28-O-beta-D-galactopyranosyl-(1-->5)-beta-D-apiofuranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranosyl ester (polygalasaponin L), in addition to five known compounds have been isolated from the roots of Polygala japonica.
View Article and Find Full Text PDFJ Asian Nat Prod Res
September 2006
Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100083, China.
Two new acylated presenegenin glycosides E-onjisaponin H (5) and Z-onjisaponin (6) together with seven known saponins were isolated from the roots of Polygala tenuifolia Willd. Compounds 5 and 6 were obtained as a pair of isomers due to trans and cis-p-methoxycinnamoyl. Their structures were elucidated mainly by 2D-NMR techniques including 1H-1HCOSY, TOCSY, HSQC, HMBC as 3-O-(beta-D-glucopyranosyl) presenegenin 28-[O-beta-D-apiofuranosyl-(1 --> 3)-O-[beta-D-xylopyranosyl-(1 --> 4)]-O-alpha-L-rhamnopyranosyl-(1 --> 2)-O-[alpha-L-rhamnopyranosyl-(1 --> 3)]-4-O-[(E)-p-methoxycinnamoyl]-beta-D-fucopyranosyl] ester (5) and its (Z)-isomer (6).
View Article and Find Full Text PDFZhong Yao Cai
January 2006
Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Central South University, Changsha 410013, China.
Objective: To study the antihyperlipidemia effective constituent of Polygala fallax Hemsl.
Method: Column chromatographic techniques were employed for isolation and purification of chemical constituents of the plant and the structures were elucidated by IR, NMR and MS spectroscopy.
Result: Four triterpenoid saponins were isolated and determined as 3-O-beta-D-glucopyranosyl-( 1--> 2) -beta-D-glucopyranosyl presenegenin 28-O-beta-D-xylopyranosyl-(1-->4 ) -alpha-L-rhamnopyranosyl-(1-->2 ) -beta-D-fucopyranosyl ester (I), 3-O-beta-D-glucopyranosyl-(1-->2) -beta-D-glucopyranosyl presenegenin 28-O-beta-D-xylopyranosyl-(1-->4) -alpha-L-rhamnopyranosyl-(1-->2) -(3-O-acetyl)-beta-D-fucopyranosyl ester (II), 3-O-beta-D-glucopyranosyl-(1-->2) -beta-D-glucopyranosyl presenegenin 28-O-beta-D-xylopyranosyl-(1-->4) -alpha-L-rhamnopyranosyl-(1-->2) -(4-O-acetyl) -beta-D-fucopyranosyl ester (II) and 3-O-beta-D-glucopyranosyl-(1--2) -beta-D-glucopyranosyl presenegenin 28-O-beta-D-xylopyranosyl-(1-->4 ) -alpha-L-rhamnopyranosyl-(1-->2 ) - (3,4-diacetyl) -beta-D-fucopyranosyl ester (IV).
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