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

The structure was elucidated in this paper
Publication DOI: 10.1016/j.bse.2004.04.014
Journal NLM ID: 0430442
Publisher: Pergamon Press
Correspondence: malacd

u-bourgogne.fr
Institutions: Laboratoire de Pharmacognosie, Unite de Molecules d'Interet Biologique (UMIB EA 3660), Faculte de Pharmacie, Universite de Bourgogne, 7 Bd Jeanne

No abstract

glycolipid, sesquiterpene, Homalomena occulta, Araceae, Hederagenin saponin, Diacylphosphatidylcholine, N-(p-coumaroyl)-serotonine

Structure type: oligomer
Location inside paper: compound 1
Compound class: glycolipid, saponin
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_423153,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, MPLC

Related record ID(s): 14462
NCBI Taxonomy refs (TaxIDs): 714477
Show glycosyltransferases

NMR conditions: in C5D5N [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4	bDGlcp	105.0	75.0	78.8	69.5	78.4	62.2
3	bDGlcpA	106.4	74.5	78.4	82.4	72.4	173.6
28	bDGlcp	95.4	74.1	78.8	71.3	78.9	62.8
	xXHederagenin

¹H NMR data: present in publication

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4	bDGlcp	105.0	75.0	78.8	69.5	78.4	62.2
3	bDGlcpA	106.4	74.5	78.4	82.4	72.4	173.6
28	bDGlcp	95.4	74.1	78.8	71.3	78.9	62.8
	xXHederagenin

There is only one chemically distinct structure:

CC1(C)CC[C@]2(C(=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](C(=O)O)[C@@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]2C1

SVG MW SMILES 3D mol Ionize

Taxonomic group: plant / Streptophyta (Phylum: Streptophyta)
Organ / tissue: fruit, aerial part

The structure was elucidated in this paper
NCBI PubMed ID: 9118449
Publication DOI: 10.1248/cpb.45.349
Journal NLM ID: 0377775
Publisher: Pharmaceutical Society Of Japan
Institutions: Centro de Investigaciones en Productos Naturales, Universidad de Costa Rica, San Jose, Costa Rica

Six bisdesmosidic bayogenin saponins, named tacacosides A1, A2, B1, B2, B3 and C, were isolated from the fruit and aerial parts of Sechium pittieri (COGN.) C. Jeffrey and S. talamancense (WUNDERLIN) C. Jeffrey, Costa Rican cucurbitaceae plants. Their structures were elucidated on spectral and chemical evidence as follows. Tacacoside A1: 3-O[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl]bayogenin 28-O-(α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-β-D-apiofuranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl) ester, tacacoside A2: 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl]bayogenin 28-O-(α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl) ester, tacacoside B1: 3-O-[β-D-glucopyranosyl]bayogenin 28-O-(α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[β-D-apiofuranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl) ester, tacacoside B2: 3-O-[β-D-glucopyranosyl]bayogenin 28-O-(α-L-rhamnopyranosyl-(1→3)-β-D-xylpyranosyl-(1→4)-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl) ester, tacacoside B3: 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl] bayogenin 28-O-[α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl] ester, and tacacoside C: 3-O-[β-D-glucopyranosyl]bayogenin 28-O-[α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl] ester. These saponins showed moderate antiproliferative activity (ED50:10-74 micrograms/ml) against MK-1, HeLa and B16F10 cells.

Antiproliferative activity, Cucurbitaceae, Sechium, tacacoside, bayogenin glycoside

Structure type: oligomer ; 1523 [M+Na]+
C₆₉H₁₁₂O₃₅
Location inside paper: abstract, p.354, tacacoside A1 (1)
Trivial name: tacacoside A1
Compound class: saponin
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_153543,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, FAB-MS, sugar analysis, TLC, enzymatic hydrolysis, mild acid hydrolysis, GC, chemical methods, biological assays, methanolysis, HPLC, extraction
Biological activity: antiproliferative activity of isolated saponins against some tumor cells
Comments, role: NMR data for aglycon are present in publication.

Related record ID(s): 60568, 60569, 60570, 60571, 60572, 60573, 60574, 60575, 60576, 60577, 60578, 60579, 60580, 60581, 60582
NCBI Taxonomy refs (TaxIDs): 517551, 1132096
Show glycosyltransferases

¹H NMR data: present in publication

¹³C NMR data: present in publication

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@H]2[C@H](OC(=O)[C@]34CCC(C)(C)C[C@H]3C3=CC[C@@H]5[C@@]6(C)C[C@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O)[C@@](C)(CO)[C@@H]6CC[C@@]5(C)[C@]3(C)CC4)OC[C@H](O)[C@@H]2O)[C@H](O)[C@H](O[C@@H]2OC[C@](O)(CO)[C@H]2O)[C@H]1O[C@@H]1OC[C@@H](O)[C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H]1O

SVG MW SMILES 3D mol Ionize