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Taxonomic group: plant / Streptophyta (Phylum: Streptophyta)
Organ / tissue: root

The structure was elucidated in this paper
Publication DOI: 10.1021/np960256b
Journal NLM ID: 7906882
Publisher: American Society of Pharmacognosy
Institutions: National Research Institute of Chinese Medicine, Taipei, Taiwan, Republic of China

β-Sitosterol, β-amyrin, 4-hydroxyacetophenone, 3,4-dihydroxyacetophenone, sitosteryl 3-O-β-D-glucopyranoside, cynandione A, and cynanonesides A (3) and B (4) were isolated from the roots of Cynanchum taiwanianum. The latter two compounds are new acetophenone glucosides, and their structures were elucidated on the basis of spectral and chemical evidence. Meanwhile, the structure of cynandione A, previously designated as 3',4-diacetyl-2,2',3,6'-tetrahydroxybiphenyl, has been revised as 2,3'-diacetyl-2',3,6,6'-tetrahydroxybiphenyl (9).

Structure type: monomer ; 313 [M-H]-
C₁₄H₁₈O₈
Location inside paper: p.369, 3
Trivial name: cynanoneside A
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, FAB-MS, chemical methods, HPLC, UV, extraction, acetylation, acidic hydrolysis, acidic hydrolysids, metylation, acetylatione, xtraction
Comments, role: The known sitosteryl 3-O-β-D-glucopyranoside was isolated from the roots Cynanchum taiwanianum; atom numbering as in publication; NMR data for aglycon are present in publication..

Related record ID(s): 60379
NCBI Taxonomy refs (TaxIDs): 126747
Show glycosyltransferases

NMR conditions: in DMSO-d6 [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
4	bDGlcp	101.7	73.3	76.7	69.7	77.0	60.7
	Subst


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
4	bDGlcp	4.81	?	?	?	?	3.44-3.69
	Subst


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
4	bDGlcp	101.7/4.81	73.3/?	76.7/?	69.7/?	77.0/?	60.7/3.44-3.69
	Subst

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
4	bDGlcp	4.81	?	?	?	?	3.44 3.69
	Subst

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
4	bDGlcp	101.7	73.3	76.7	69.7	77.0	60.7
	Subst

There is only one chemically distinct structure:

CC(=O)c1ccc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(O)c1

SVG MW SMILES 3D mol Ionize

Structure type: monomer ; 313 [M-H]-
C₁₄H₁₈O₈
Location inside paper: p.369, 4
Trivial name: cynanoneside B
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, FAB-MS, chemical methods, HPLC, UV, extraction, acetylation, acidic hydrolysis, acidic hydrolysids, metylation, acetylatione, xtraction
Comments, role: Cynanoneside B was an isomer of cynanoneside A. The known sitosteryl 3-O-β-D-glucopyranoside was isolated from the roots Cynanchum taiwanianum. Atom numbering as in publication; NMR data for aglycon are present in publication.

Related record ID(s): 60378
NCBI Taxonomy refs (TaxIDs): 126747
Show glycosyltransferases

NMR conditions: in DMSO-d6 [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2	bDGlcp	101.6	73.2	76.7	69.4	77.1	60.5
	Subst


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2	bDGlcp	4.91	?	?	?	?	3.51-3.70
	Subst


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2	bDGlcp	101.6/4.91	73.2/?	76.7/?	69.4/?	77.1/?	60.5/3.51-3.70
	Subst

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2	bDGlcp	4.91	?	?	?	?	3.51 3.70
	Subst

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2	bDGlcp	101.6	73.2	76.7	69.4	77.1	60.5
	Subst

There is only one chemically distinct structure:

CC(=O)c1ccc(O)cc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize