CSDB: Search results

Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Organ / tissue: mycelium

NCBI PubMed ID: 22428587
Publication DOI: 10.1080/10286020.2012.670220
Journal NLM ID: 100888334
Publisher: Harwood Academic Publishers; London: Informa Healthcare
Correspondence: Zhu ZY <zhyuanzhu

tust.edu.cn>
Institutions: Key Laboratory of Food Nutrition and Safety, Ministry of Education, College of Food Science and Biotechnology, Tianjin University of Science and Technology, Tianjin, China, Tianjin Key Laboratory of Pulp & Paper, College of Material Science and Chemical Engineering, Tianjin University of Science and Technology, Tianjin, China, Université Pierre et Marie Curie-Paris 6, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), Paris, France

Ergosterol 3-O-β-D-glucopyranoside (1a) and ergosterol 3-O-β-D-galactopyranoside (1b) were highly efficiently synthesized and evaluated for their inhibitory activities against two tumor cell lines. The structures of these compounds were extensively confirmed by (1)H, (13)C NMR, IR, and HRMS. Compounds 1a and 1b exhibited interesting cytotoxic profiles. The antitumor activity of compound 1a was higher than that of 1b.

glycosylation, ergosterol, Cordyceps sinensis, saponins

Structure type: monomer ; 581.3789 [M+Na]+
C₃₄H₅₄O₆
Location inside paper: Fig.1, structure 1a
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, TLC, MS, optical rotation measurement, CC
Biological activity: Inhibition rate of compound against S180 tumor cells reduced gradually with decreasing concentrations. In 24 h, inhibition rate achieved maximum of 90%. As for H22 cells, inhibition rate has no doseresponse relationship. The inhibition rate of ergosterol galactoside was higher than the inhibition rate of ergosterol glucoside against S180 cells and was lower against H22 cells.
Synthetic data: chemical
Comments, role: NMR temperature was not specified

Related record ID(s): 45986
NCBI Taxonomy refs (TaxIDs): 72228
Show glycosyltransferases

NMR conditions: in DMSO-d6 [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23	C24	C25	C26	C27	C28
3	bDGlcp	101.3	73.9	76.2	70.5	77.2	61.6
	Subst	37.4	30.1	?	38.2	140.8	149.7	116.6	146.8	46.0	28.4	20.3	38.4	42.8	54.3	21.5	27.9	55.5	12.3	16.3	40.1	20.2	136.7	132.0	42.6	32.9	21.4	19.9	17.8


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19	H20	H21	H22	H23	H24	H25	H26	H27
3	bDGlcp	4.26	2.40-2.91	3.03-3.16	3.03-3.16	3.03-3.16	3.43-3.61
	Subst	?	?	3.43-3.45	?	?	5.54	5.17-5.36	?	?	?	?	?	?	?	?	?	0.58	0.62	?	1.02	?	?	?	0.89	?	0.91	0.82


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10	C11/H11	C12/H12	C13/H13	C14/H14	C15/H15	C16/H16	C17/H17	C18/H18	C19/H19	C20/H20	C21/H21	C22/H22	C23/H23	C24/H24	C25/H25	C26/H26	C27/H27
3	bDGlcp	101.3/4.26	73.9/2.40-2.91	76.2/3.03-3.16	70.5/3.03-3.16	77.2/3.03-3.16	61.6/3.43-3.61
	Subst	NMR TSV error 2: unequal length of 13C and 1H datasets

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19	H20	H21	H22	H23	H24	H25	H26	H27
3	bDGlcp	4.26	2.40 2.91	3.03 3.16	3.03 3.16	3.03 3.16	3.43 3.61
	Subst	?	?	3.43 3.45	?	?	5.54	5.17 5.36	?	?	?	?	?	?	?	?	?	0.58	0.62	?	1.02	?	?	?	0.89	?	0.91	0.82

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23	C24	C25	C26	C27	C28
3	bDGlcp	101.3	73.9	76.2	70.5	77.2	61.6
	Subst	37.4	30.1	?	38.2	140.8	149.7	116.6	146.8	46.0	28.4	20.3	38.4	42.8	54.3	21.5	27.9	55.5	12.3	16.3	40.1	20.2	136.7	132.0	42.6	32.9	21.4	19.9	17.8

The spectrum also has 1 signal at unknown position (not plotted).

There is only one chemically distinct structure:

CC(C)[C@@H](C)/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C

SVG MW SMILES 3D mol Ionize