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

The structure was elucidated in this paper
NCBI PubMed ID: 10395509
Publication DOI: 10.1021/np9803676
Journal NLM ID: 7906882
Publisher: American Society of Pharmacognosy
Correspondence: Tóth G <g-toth

chem.bme.hu>; Soliman HSM <hsmsoliman

hotmail.com>
Institutions: Pharmacognosy Department, Faculty of Pharmacy, Helwan University, Ain-Helwan, Cairo, Egypt, Laboratory of Natural Products, National Research Centre, Dokki-Cairo, Egypt, Technical Analytical Research Group of the Hungarian Academy of Sciences, Institute for General and Analytical Chemistry, Technical University of Budapest, H-1111 Budapest, Hungary, Institute for Drug Research Ltd., Berlini u. 47−49, H-1045 Budapest, Hungary, and Institut für Organische Chemie, Universität Hannover, Hannover, Germany

The structure elucidation of a new saponin from Arenaria filicaulis (Boiss.), Caryophyllaceae, Snatzkein F (1), containing gypsogenin with a tetrasaccharide moiety was accomplished by use of 1D and 2D NMR methods.

structure elucidation, Arenaria filicaulis, gypsogenin saponin

Structure type: oligomer ; 1091 [M+Na]+
Location inside paper: compound 1, table 1, table 2
Trivial name: snatzkein F
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_142489,IEDB_149135,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823,SB_86

Methods: 1H NMR, NOE, FAB-MS, optical rotation measurement, ROESY, TOCSY, HMBC, HMQC, DEPT, COSY, 14C NMR
Comments, role: NMR temperature was not specified

NCBI Taxonomy refs (TaxIDs): 3577
Show glycosyltransferases

NMR conditions: in C5D5N [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	C29	C30
28,2,4	bDXylp	107.5	76.2	78.7	70.9	67.5
28,2	aLRhap	102.1	71.4	72.4	84.7	68.7	18.6
28,3	bLAraf	111.8	83.6	78.1	85.9	62.0
28,4	Ac	170.8	20.8
28	bDFucp	94.4	73.6	80.8	73.9	70.5	16.5
	Subst	38.7	27.1	71.6	56.3	48.0	21.3	32.7	40.3	48.0	36.2	23.8	122.5	144.0	42.4	28.4	23.5	47.2	42.1	46.4	30.7	34.0	32.3	207.3	9.8	15.9	17.5	25.9	176.5	23.7	33.1


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	H28	H29	H30
28,2,4	bDXylp	5.01	4.02	4.02	4.15	3.49-4.23
28,2	aLRhap	6.00	4.73	4.58	4.30	4.39	1.76
28,3	bLAraf	5.71	4.88	4.81	4.70	4.16-4.30
28,4	Ac	-	1.97
28	bDFucp	5.99	4.53	4.25	5.76	3.93	1.16
	Subst	1.03-1.57	1.86	4.03	-	1.45	1.17-1.51	1.63	1.56	1.74	-	1.92	5.43	-	-	1.43-1.98	1.88-2.09	-	3.09	1.20-1.73	-	1.11-1.28	1.71-1.97	9.55	1.31	0.90	1.05	1.23	-	0.84	0.86


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	C28/H28	C29/H29	C30/H30
28,2,4	bDXylp	107.5/5.01	76.2/4.02	78.7/4.02	70.9/4.15	67.5/3.49-4.23
28,2	aLRhap	102.1/6.00	71.4/4.73	72.4/4.58	84.7/4.30	68.7/4.39	18.6/1.76
28,3	bLAraf	111.8/5.71	83.6/4.88	78.1/4.81	85.9/4.70	62.0/4.16-4.30
28,4	Ac		20.8/1.97
28	bDFucp	94.4/5.99	73.6/4.53	80.8/4.25	73.9/5.76	70.5/3.93	16.5/1.16
	Subst	38.7/1.03-1.57	27.1/1.86	71.6/4.03		48.0/1.45	21.3/1.17-1.51	32.7/1.63	40.3/1.56	48.0/1.74		23.8/1.92	122.5/5.43			28.4/1.43-1.98	23.5/1.88-2.09		42.1/3.09	46.4/1.20-1.73		34.0/1.11-1.28	32.3/1.71-1.97	207.3/9.55	9.8/1.31	15.9/0.90	17.5/1.05	25.9/1.23		23.7/0.84	33.1/0.86

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H11	H12	H15	H16	H18	H19	H21	H22	H23	H24	H25	H26	H27	H29	H30
28,2,4	bDXylp	5.01	4.02	4.02	4.15	3.49 4.23
28,2	aLRhap	6.00	4.73	4.58	4.30	4.39	1.76
28,3	bLAraf	5.71	4.88	4.81	4.70	4.16 4.30
28,4	Ac		1.97
28	bDFucp	5.99	4.53	4.25	5.76	3.93	1.16
	Subst	1.03 1.57	1.86	4.03		1.45	1.17 1.51	1.63	1.56	1.74	1.92	5.43	1.43 1.98	1.88 2.09	3.09	1.20 1.73	1.11 1.28	1.71 1.97	9.55	1.31	0.90	1.05	1.23	0.84	0.86

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	C29	C30
28,2,4	bDXylp	107.5	76.2	78.7	70.9	67.5
28,2	aLRhap	102.1	71.4	72.4	84.7	68.7	18.6
28,3	bLAraf	111.8	83.6	78.1	85.9	62.0
28,4	Ac	170.8	20.8
28	bDFucp	94.4	73.6	80.8	73.9	70.5	16.5
	Subst	38.7	27.1	71.6	56.3	48.0	21.3	32.7	40.3	48.0	36.2	23.8	122.5	144.0	42.4	28.4	23.5	47.2	42.1	46.4	30.7	34.0	32.3	207.3	9.8	15.9	17.5	25.9	176.5	23.7	33.1

There is only one chemically distinct structure:

CC(=O)O[C@@H]1[C@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@H]2O)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)[C@H](OC(=O)[C@]23CCC(C)(C)C[C@@H]2C2=CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(C=O)C5CC[C@@]4(C)[C@]2(C)CC3)O[C@@H]1C

SVG MW SMILES 3D mol Ionize