Chemistry of Natural Compounds, Vol. 47, No. 2, May, 2011 [Russian original No. 2, March–April, 2011]
GLUCOMANNANS OF Serissa serissoides STEM
1,2
1
1
Hanmin Zhao, Min Zhou, Meiyan Huang,
UDC 547.917
3
1*
Kuiwu Wang, and Wanxing Wei
One ꢁ-D-glucomannan was isolated from Serissa serissoides (DC.) Druce. The average molecular weight of
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the polysaccharide was established to be 2.9 ꢂ 10 Da. The structure of the polysaccharide from S. serissoides
(SSP) was investigated by using sugar and methylation analysis, infrared spectroscopy, mass spectrometry,
and NMR spectroscopy. The experiments revealed that SSP consisted of ꢁ-D-Glcp and ꢁ-D-Manp units in
the ratio of approximately 1.1:1 with ꢁ-D-(1ꢃ4)-Glcp and ꢁ-D-(1ꢃ2) Manp linkages.
Keywords: Serissa serissoides (DC.) Druce, polysaccharide, ꢁ-D-glucomannan, structural analysis.
Serissa serissoides (DC.) Druce belongs to the Rubiacea family and is widely distributed in China. It has been used
as traditional medicine to remedy hepatitis and hepatocirrhosis in China for a long time. Bioactive investigation showed that
the water extract of S. serissoides effectively inhibited secretion of HBsAg and HBeAg from the HepG 2.2.15 cell line ꢄ1ꢅ and
protected mice liver from injuries from carbon tetrachloride, acetaminophen, and thioacetamide ꢄ2ꢅ. The water extract also
increased the avoirdupois and thymus gland index of the tested mice ꢄ3ꢅ and showed antimicrobial activities ꢄ4ꢅ. Chemical
investigations of S. serissoides led to the isolation of ursolic acid, 10-deacetyl asperulosidic acid, paedemsidic acid, oleanolic
acid, palmitic acid, corosolic acid, urs-12-en-28-ol, 4-hydroxy-3-methoxybenzoic acid, 2,6-dimethoxy-p-benzoquinone,
(–)-syringaresinol, (+)-medioresinol, vitexin, daucosterol, (+)-pinoresinol, (–)-syringaresinol-4-O-ꢁ-D-glucopyranoside,
D-mannitol, ꢁ-sitosterol, and (–)-olivil from S. serissoides ꢄ5–7ꢅ. Investigation of polysaccharides from S. serissoides has not
been reported. We described herein the isolation and structural analysis of the polysaccharide from the water extract of
S. serissoides.
Polysaccharide SSP was isolated by water extraction. Crude polysaccharide was extracted by Sevag reagent to remove
protein. Absence of a peak at 280 nm in the ultraviolet absorption spectrum revealed that the sample did not contain protein.
Column gel permeation chromatography (Sephadex G-25) of the water-soluble sample yielded a pure Serissa serissoides
polysaccharide (SSP). The total sugar content in SSP was estimated by the phenol–sulfuric acid method ꢄ8ꢅ and was found to
be 99%. HPGPC showed only one symmetric peak, from which the weight-average molecular mass was estimated to be
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2.9 ꢂ 10 Da by referencing to authoritative dextrans. Sugar analysis revealed the presence of Glc and Man by referencing to
authoritative monosaccharides.
The results of GLC-MS analysis of partially methylated alditol acetates obtained from SSP identified three products:
1,5-di-O-acetyl-2,3,4,6-tetra-O-methyl-D-glucitol (m/z: 59, 87, 101, 113, 117, 131, 145, 161, 205), 1,2,5-tri-O-acetyl-3, 4,6-
tri-O-methyl-D-mannitol (m/z: 43, 58, 87, 101, 129, 143, 161, 189, 233), and 1,4,5-tri-O-acetyl-2,3,6-tri-O-methyl-D-glucitol
(m/z: 59, 87, 99, 101, 113, 117, 113, 131, 157, 233) in a molar percentage of 19:38.3: 42.7 on the basis of peak areas.
1,5-Di-O-acetyl-2,3,4,6-tetra-O-methyl-D-glucitol was derived from Glcp (1ꢃ) residue as a terminal in the polysaccharide.
1,4,5-Tri-O-acetyl-2,3,6-tri-O-methyl-D-glucitol was derived from (1ꢃ4) Glcp residue, and 1,2,5-tri-O-acetyl-3,4,6-tri-O-
methyl-D-mannitol from (1ꢃ2) Manp residues in SSP. SSP showed absorption bands at 890, 922, 1018, 1084, 1142, 2940,
–1
–1
and 3420 cm in the IR. The bands at 814, 873, and 897 cm were ascribed to the ꢁ-type glycosidic linkage of Manp and
–1
Glcp ꢄ9ꢅ. The bands at 1018, 1084, and 1142 cm were ascribed to the glycosidic linkage (C-O-C) and (C-O-H).
1) Department of Chemistry, Guangxi University, Nanning, Guangxi, 530004, fax: 86 771 3233718, e-mail:
chewxwei@yahoo.com.cn; 2) Department of Chemistry and Bioengineering, Nanning Teachers College, 532400; 3) College
of Food Science and Biotechnology Engineering, Zhejiang Gongshang University, Hangzhou, 310035, Peopleꢀs Republic of
China. Published in Khimiya Prirodnykh Soedinenii, No. 2, pp. 163–165, March–April, 2011. Original article submitted
December 18, 2009.
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0009-3130/11/4702-0176 02011 Springer Science+Business Media, Inc.