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

The structure was elucidated in this paper
Publication DOI: 10.1016/S0031-9422(98)00042-9
Journal NLM ID: 0151434
Publisher: Elsevier
Institutions: Dipartimento di Chimica Organica e Industriale, Università di Milano, Milan, Italy, Pharmacia and Upjohn, Preclinical Research, Biotechnology-Structural Biology, NMR Lab., Nerviano, Italy, Pharmacognosy Department, Faculty of Pharmacy, University of Alexandria, Alexandria, Egypt

Two new cycloartane saponins were isolated from the aerial parts of Astragalus sieberi. The structures were elucidated by 1D- and 2D- gradient-enhanced NMR analyses and enzymatic hydrolysis as 20(S),24(R)-epoxy-9 beta, 19-cyclolanostan-3 beta,6 alpha,16 beta,25-tetrol-3-O-beta-D-glucopyranoside and 20(S),24(R)-epoxy-9 beta,19-cyclolanostan-3 beta,6 alpha,16 beta,25-tetrol-3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside.

structural elucidation, Leguminosae, Astragalus sieberi, 1D- and 2D-gradient enhanced NMR techniques, 20(S), 24(R)-epoxy-9 beta, 19-cyclolanostan-3 beta, 6 alpha, 16 beta, 25-tetrol glycosides, sieberoside I and II

Structure type: monomer ; 651 [M-H]-
C₃₆H₆₀O₁₀
Location inside paper: p. 1404, Scheme, compound 1, table 2, table 3
Trivial name: sieberoside I
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, FAB-MS, optical rotation measurement, ROESY, TOCSY, column chromatography, DQF-COSY, extraciton, GHSQC, GHMBC, 1H NR, E-COSY

Related record ID(s): 61553
NCBI Taxonomy refs (TaxIDs): 1423377
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	bDGlcp	106.7	75.6	78.4	71.5	77.9	62.7
	Subst	32.3	30.5	88.9	42.4	53.8	67.9	38.9	46.6	20.8	29.3	26.4	33.5	46.3	46.6	48.6	72.7	56.2	21.0	30.0	86.5	26.1	37.3	24.1	85.5	70.2	27.8	26.6	28.8	16.5	20.3


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	bDGlcp	4.96	4.05	4.22	4.18	3.94	4.38-4.52
	Subst	1.10	?	3.65	-	?	3.74	?	?	-	-	?	?	-	-	?	4.76	2.22	1.63	0.22-0.54	-	1.30	2.47	?	3.95	-	?	?	2.00	1.35	0.98


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	bDGlcp	106.7/4.96	75.6/4.05	78.4/4.22	71.5/4.18	77.9/3.94	62.7/4.38-4.52
	Subst	32.3/1.10	30.5/?	88.9/3.65		53.8/?	67.9/3.74	38.9/?	46.6/?			26.4/?	33.5/?			48.6/?	72.7/4.76	56.2/2.22	21.0/1.63	30.0/0.22-0.54		26.1/1.30	37.3/2.47	24.1/?	85.5/3.95		27.8/?	26.6/?	28.8/2.00	16.5/1.35	20.3/0.98

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	bDGlcp	4.96	4.05	4.22	4.18	3.94	4.38 4.52
	Subst	1.10	?	3.65		?	3.74	?	?			?	?			?	4.76	2.22	1.63	0.22 0.54		1.30	2.47	?	3.95		?	?	2.00	1.35	0.98

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	bDGlcp	106.7	75.6	78.4	71.5	77.9	62.7
	Subst	32.3	30.5	88.9	42.4	53.8	67.9	38.9	46.6	20.8	29.3	26.4	33.5	46.3	46.6	48.6	72.7	56.2	21.0	30.0	86.5	26.1	37.3	24.1	85.5	70.2	27.8	26.6	28.8	16.5	20.3

There is only one chemically distinct structure:

CC(C)(O)C1CC[C@@](C)(C2[C@@H](O)C[C@@]3(C)C4C[C@H](O)C5C(C)(C)[C@@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)CC[C@@]56C[C@@]46CC[C@]23C)O1

SVG MW SMILES 3D mol Ionize

Structure type: oligomer ; 837 [M+Na]+
C₄₂H₇₀O₁₅
Location inside paper: p. 1404, Scheme, compound 2, table 2, table 3
Trivial name: sieberoside II
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_140628,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, FAB-MS, optical rotation measurement, ROESY, TOCSY, column chromatography, DQF-COSY, extraciton, GHSQC, GHMBC, 1H NR, E-COSY

Related record ID(s): 61552
NCBI Taxonomy refs (TaxIDs): 1423377
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
3,2	bDGlcp	106.2	77.2	78.2	72.0	78.3	63.0
3	bDGlcp	105.1	83.7	78.5	71.7	78.1	63.0
	Subst	32.5	30.4	89.1	42.9	54.2	67.9	38.6	46.9	21.2	29.5	26.6	33.9	46.6	47.0	49.0	73.0	56.6	21.2	30.4	86.8	26.5	37.7	24.5	85.1	70.4	28.3	27.0	29.0	16.7	20.6


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
3,2	bDGlcp	5.38	4.12	4.22	4.29	3.94	4.42-4.48
3	bDGlcp	4.97	4.24	4.26	4.16	3.86	4.35-4.52
	Subst	1.10-1.51	1.94-2.42	3.57	-	1.67	3.74	1.62-1.79	1.97	-	-	1.22-1.90	1.70-1.82	-	-	1.80-2.13	4.81	2.24	1.65	0.21-0.56	-	1.33	1.68-2.49	1.90-2.23	3.94	-	?	?	1.96	1.42	1.00


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
3,2	bDGlcp	106.2/5.38	77.2/4.12	78.2/4.22	72.0/4.29	78.3/3.94	63.0/4.42-4.48
3	bDGlcp	105.1/4.97	83.7/4.24	78.5/4.26	71.7/4.16	78.1/3.86	63.0/4.35-4.52
	Subst	32.5/1.10-1.51	30.4/1.94-2.42	89.1/3.57		54.2/1.67	67.9/3.74	38.6/1.62-1.79	46.9/1.97			26.6/1.22-1.90	33.9/1.70-1.82			49.0/1.80-2.13	73.0/4.81	56.6/2.24	21.2/1.65	30.4/0.21-0.56		26.5/1.33	37.7/1.68-2.49	24.5/1.90-2.23	85.1/3.94		28.3/?	27.0/?	29.0/1.96	16.7/1.42	20.6/1.00

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H11	H12	H15	H16	H17	H18	H19	H21	H22	H23	H24	H26	H27	H28	H29	H30
3,2	bDGlcp	5.38	4.12	4.22	4.29	3.94	4.42 4.48
3	bDGlcp	4.97	4.24	4.26	4.16	3.86	4.35 4.52
	Subst	1.10 1.51	1.94 2.42	3.57		1.67	3.74	1.62 1.79	1.97	1.22 1.90	1.70 1.82	1.80 2.13	4.81	2.24	1.65	0.21 0.56	1.33	1.68 2.49	1.90 2.23	3.94	?	?	1.96	1.42	1.00

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
3,2	bDGlcp	106.2	77.2	78.2	72.0	78.3	63.0
3	bDGlcp	105.1	83.7	78.5	71.7	78.1	63.0
	Subst	32.5	30.4	89.1	42.9	54.2	67.9	38.6	46.9	21.2	29.5	26.6	33.9	46.6	47.0	49.0	73.0	56.6	21.2	30.4	86.8	26.5	37.7	24.5	85.1	70.4	28.3	27.0	29.0	16.7	20.6

There is only one chemically distinct structure:

CC(C)(O)C1CC[C@@](C)(C2[C@@H](O)C[C@@]3(C)C4C[C@H](O)C5C(C)(C)[C@@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)CC[C@@]56C[C@@]46CC[C@]23C)O1

SVG MW SMILES 3D mol Ionize