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

The structure was elucidated in this paper
NCBI PubMed ID: 9433817
Publication DOI: 10.1016/S0031-9422(97)00574-8
Journal NLM ID: 0151434
Publisher: Elsevier
Institutions: Institute of Organic Chemistry, Siberian Branch of Russsian Academy of Sciences, Irkutsk, Russian Federation, Department of Chemistry and Biochemistry, Brigham Young University, Provo, US

A new triterpenoid saponin, thalicoside F was isolated from the above- ground part of Thalictrum minus L. (Ranunculaceae family) collected in Eastern Siberia (Russia). The structure of thalicoside F was elucidated by a combination of 1D- and 2D-NMR spectroscopy and mass spectroscopy, and was determined to be C47H74O17{3-β-O-[α-L-rhamnopyranosyl-(1 → 2)-β- D-glucopyranosyl-(1 → 4)-α-L-arabinopyranosyl]-11α, 12α-epoxyoleanane- 28,13β-olide}.

Ranunculaceae, triterpenoid saponins, NMR spectra, oleanane, thalicoside F, Thalictrum minus L.

Structure type: oligomer ; 933.4822 [M+Na]+
C₄₇H₇₄O₁₇
Location inside paper: Fig. 3, table 1, table 2
Trivial name: thalicoside F
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

Methods: extraction, ROESY, TOCSY, melting point determination, COSY, HR-FAB-MS, HETCOR, NMBC

NCBI Taxonomy refs (TaxIDs): 476039
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
3,4,2	aLRhap	101.97	72.09	72.37	74.58	70.02	18.65
3,4	bDGlcp	105.10	78.26	78.89	71.76	78.31	62.68
3	aLArap	107.16	72.85	73.77	78.77	65.34
	Subst	38.42	26.08	88.71	39.54	55.0	17.73	31.36	40.89	51.13	36.42	52.74	57.26	87.60	41.63	27.05	21.64	44.09	49.76	38.02	31.50	34.42	27.65	27.83	16.33	17.26	18.38	20.37	178.92	33.08	23.48


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
3,4,2	aLRhap	6.27	4.75	4.76	4.22	4.96	1.68
3,4	bDGlcp	5.17	4.17	4.20	4.17	3.87	4.33-4.46
3	aLArap	4.74	4.44	4.25	4.38	3.82-4.67
	Subst	1.05-1.76	1.83-2.02	3.24	-	0.71	0.88	1.03-1.18	-	1.64	-	3.07	3.24	-	-	1.00-1.34	1.28-2.16	-	2.52	1.72-1.94	-	1.19-1.33	1.64-1.78	1.20	0.93	0.90	1.22	1.12	-	0.89	0.81


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
3,4,2	aLRhap	101.97/6.27	72.09/4.75	72.37/4.76	74.58/4.22	70.02/4.96	18.65/1.68
3,4	bDGlcp	105.10/5.17	78.26/4.17	78.89/4.20	71.76/4.17	78.31/3.87	62.68/4.33-4.46
3	aLArap	107.16/4.74	72.85/4.44	73.77/4.25	78.77/4.38	65.34/3.82-4.67
	Subst	38.42/1.05-1.76	26.08/1.83-2.02	88.71/3.24		55.0/0.71	17.73/0.88	31.36/1.03-1.18		51.13/1.64		52.74/3.07	57.26/3.24			27.05/1.00-1.34	21.64/1.28-2.16		49.76/2.52	38.02/1.72-1.94		34.42/1.19-1.33	27.65/1.64-1.78	27.83/1.20	16.33/0.93	17.26/0.90	18.38/1.22	20.37/1.12		33.08/0.89	23.48/0.81

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H9	H11	H12	H15	H16	H18	H19	H21	H22	H23	H24	H25	H26	H27	H29	H30
3,4,2	aLRhap	6.27	4.75	4.76	4.22	4.96	1.68
3,4	bDGlcp	5.17	4.17	4.20	4.17	3.87	4.33 4.46
3	aLArap	4.74	4.44	4.25	4.38	3.82 4.67
	Subst	1.05 1.76	1.83 2.02	3.24		0.71	0.88	1.03 1.18	1.64	3.07	3.24	1.00 1.34	1.28 2.16	2.52	1.72 1.94	1.19 1.33	1.64 1.78	1.20	0.93	0.90	1.22	1.12	0.89	0.81

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
3,4,2	aLRhap	101.97	72.09	72.37	74.58	70.02	18.65
3,4	bDGlcp	105.10	78.26	78.89	71.76	78.31	62.68
3	aLArap	107.16	72.85	73.77	78.77	65.34
	Subst	38.42	26.08	88.71	39.54	55.0	17.73	31.36	40.89	51.13	36.42	52.74	57.26	87.60	41.63	27.05	21.64	44.09	49.76	38.02	31.50	34.42	27.65	27.83	16.33	17.26	18.38	20.37	178.92	33.08	23.48

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@H]3CO[C@@H](O[C@H]4CC[C@@]5(C)C(CC[C@]6(C)C5[C@@H]5O[C@@H]5[C@]57OC(=O)C8(CCC(C)(C)CC85)CC[C@]76C)C4(C)C)[C@H](O)[C@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize