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Taxonomic group: plant / Streptophyta (Phylum: Streptophyta)

The structure was elucidated in this paper
Publication DOI: 10.1002/cjoc.19980160510
Journal NLM ID: 101312673
Publisher: Beijing, China: Science Press
Institutions: Shanghai Institute of Materia Medico, Chinese Academy of Sciences, Shanghai 200031, China

Three new 27-nor-triterpenoid saponins named rubenorside A (1), rubenorside B (2) and rubenorside C (3) were isolated from the roots of Adina rubella. Their structures were characterized as pyrocincholic acid 3 beta-O-alpha-L-rhamnopyranosyl(28-->1)-beta-D-glucopyranosyl ester (1), pyrocincholic acid 3 beta-O-beta-D-glucopyranosyl(1-->2)-beta-D-fucopyranosyl(28-->1)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl ester (2) and pyrocincholic acid 3 beta-O-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl (28-->1)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl ester (3) by spectral methods, especially 2D NMR experiments.

saponins, Rubiaceae, Adina rubella

Structure type: oligomer ; 773 [M+Na]+
C₄₁H₆₆O₁₂
Location inside paper: p. 443, compound 1, table 1, table 2
Compound class: saponin glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, FAB-MS, extraction, optical rotation measurement, peracetylation, melting point determination, HMQC, DEPT, NOESY, acid hydrolisis

Related record ID(s): 61462, 61463, 61464
NCBI Taxonomy refs (TaxIDs): 170036
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	aLRhap	104.3	72.4	72.8	74.0	69.8	18.4
28	bDGlcp	95.6	74.1	79.1	71.2	78.7	62.3
	Subst	38.3	26.0	88.8	39.2	55.4	18.8	39.5	38.	56.4	37.1	18.0	32.0	130.3	136.9	20.9	24.0	45.7	39.4	41.5	30.5	34.3	31.2	28.1	16.5	16.4	20.8	?	176.8	32.4	24.9


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	aLRhap	5.35	?	?	?	?	?
28	bDGlcp	6.30	?	?	?	?	?
	Subst	?	?	3.19	-	?	?	?	-	?	-	?	?	-	-	?	?	-	?	?	-	?	?	1.13	0.78	0.91	0.90	?	-	0.89	0.78


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	aLRhap	104.3/5.35	72.4/?	72.8/?	74.0/?	69.8/?	18.4/?
28	bDGlcp	95.6/6.30	74.1/?	79.1/?	71.2/?	78.7/?	62.3/?
	Subst	38.3/?	26.0/?	88.8/3.19		55.4/?	18.8/?	39.5/?		56.4/?		18.0/?	32.0/?			20.9/?	24.0/?		39.4/?	41.5/?		34.3/?	31.2/?	28.1/1.13	16.5/0.78	16.4/0.91	20.8/0.90	?/?		32.4/0.89	24.9/0.78

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	aLRhap	5.35	?	?	?	?	?
28	bDGlcp	6.30	?	?	?	?	?
	Subst	?	?	3.19		?	?	?	?	?	?	?	?	?	?	?	?	1.13	0.78	0.91	0.90	?	0.89	0.78

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	aLRhap	104.3	72.4	72.8	74.0	69.8	18.4
28	bDGlcp	95.6	74.1	79.1	71.2	78.7	62.3
	Subst	38.3	26.0	88.8	39.2	55.4	18.8	39.5	38.	56.4	37.1	18.0	32.0	130.3	136.9	20.9	24.0	45.7	39.4	41.5	30.5	34.3	31.2	28.1	16.5	16.4	20.8	?	176.8	32.4	24.9

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

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@H]2CC[C@@]3(C)[C@@H](CC[C@@]4(C)C5=C(CC[C@@H]43)[C@@H]3CC(C)(C)CC[C@]3(C(=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC5)C2(C)C)[C@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

saponins, Rubiaceae, Adina rubella

Structure type: oligomer ; 1097 [M+Na]+
Location inside paper: p. 443, compound 2, table 1
Compound class: saponin glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_142489,IEDB_146664,IEDB_149135,IEDB_241101,IEDB_983931,SB_192,SB_86

Methods: 13C NMR, 1H NMR, IR, FAB-MS, extraction, optical rotation measurement, peracetylation, melting point determination, HMQC, DEPT, NOESY, acid hydrolisis

Related record ID(s): 61461, 61463, 61464
NCBI Taxonomy refs (TaxIDs): 170036
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	105.9	76.8	77.8	71.3	77.9	62.5
3	bDFucp	105.0	81.6	73.8	72.3	70.7	17.2
28,6	bDGlcp	105.1	75.0	78.2	71.5	78.2	62.5
28	bDGlcp	95.5	75.2	78.5	70.8	77.8	69.3
	Subst	38.4	26.7	88.9	39.5	55.7	18.6	39.5	37.9	56.4	37.0	17.9	31.9	130.1	136.8	20.8	34.1	45.5	39.3	41.3	30.4	34.2	31.0	28.0	16.6	16.4	20.7	?	176.6	32.2	24.9


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	5.19	?	?	?	?	?
3	bDFucp	4.73	?	?	?	?	?
28,6	bDGlcp	4.97	?	?	?	?	?
28	bDGlcp	6.19	?	?	?	?	?
	Subst	?	?	3.28	-	?	?	?	-	?	-	?	?	-	-	?	?	-	?	?	-	?	?	1.28	0.79	1.04	1.10	?	-	0.89	0.85


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	105.9/5.19	76.8/?	77.8/?	71.3/?	77.9/?	62.5/?
3	bDFucp	105.0/4.73	81.6/?	73.8/?	72.3/?	70.7/?	17.2/?
28,6	bDGlcp	105.1/4.97	75.0/?	78.2/?	71.5/?	78.2/?	62.5/?
28	bDGlcp	95.5/6.19	75.2/?	78.5/?	70.8/?	77.8/?	69.3/?
	Subst	38.4/?	26.7/?	88.9/3.28		55.7/?	18.6/?	39.5/?		56.4/?		17.9/?	31.9/?			20.8/?	34.1/?		39.3/?	41.3/?		34.2/?	31.0/?	28.0/1.28	16.6/0.79	16.4/1.04	20.7/1.10	?/?		32.2/0.89	24.9/0.85

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
3,2	bDGlcp	5.19	?	?	?	?	?
3	bDFucp	4.73	?	?	?	?	?
28,6	bDGlcp	4.97	?	?	?	?	?
28	bDGlcp	6.19	?	?	?	?	?
	Subst	?	?	3.28		?	?	?	?	?	?	?	?	?	?	?	?	1.28	0.79	1.04	1.10	?	0.89	0.85

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	105.9	76.8	77.8	71.3	77.9	62.5
3	bDFucp	105.0	81.6	73.8	72.3	70.7	17.2
28,6	bDGlcp	105.1	75.0	78.2	71.5	78.2	62.5
28	bDGlcp	95.5	75.2	78.5	70.8	77.8	69.3
	Subst	38.4	26.7	88.9	39.5	55.7	18.6	39.5	37.9	56.4	37.0	17.9	31.9	130.1	136.8	20.8	34.1	45.5	39.3	41.3	30.4	34.2	31.0	28.0	16.6	16.4	20.7	?	176.6	32.2	24.9

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

There is only one chemically distinct structure:

C[C@H]1O[C@@H](O[C@H]2CC[C@@]3(C)[C@@H](CC[C@@]4(C)C5=C(CC[C@@H]43)[C@@H]3CC(C)(C)CC[C@]3(C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)CC5)C2(C)C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

saponins, Rubiaceae, Adina rubella

Structure type: oligomer ; 1113 [M+Na]+
Location inside paper: p. 443, compound 3
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_140628,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_241101,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, FAB-MS, extraction, optical rotation measurement, peracetylation, melting point determination, HMQC, DEPT, NOESY, acid hydrolisis

Related record ID(s): 61461, 61462, 61464
NCBI Taxonomy refs (TaxIDs): 170036
Show glycosyltransferases

There is only one chemically distinct structure:

CC1(C)CC[C@]2(C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)CCC3=C(CC[C@H]4[C@@]3(C)CC[C@H]3C(C)(C)[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)CC[C@@]34C)[C@@H]2C1

SVG MW SMILES 3D mol Ionize

saponins, Rubiaceae, Adina rubella

Structure type: oligomer
Location inside paper: p. 443, compound 3a, table 1
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_142489,IEDB_146664,IEDB_149135,IEDB_241101,IEDB_983931,SB_192,SB_61,SB_86

Methods: 13C NMR, 1H NMR, IR, FAB-MS, extraction, optical rotation measurement, peracetylation, melting point determination, HMQC, DEPT, NOESY, acid hydrolisis
Comments, role: product of preacetylation of ID: 61463

Related record ID(s): 61461, 61462, 61463
NCBI Taxonomy refs (TaxIDs): 170036
Show glycosyltransferases

[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
3,2,2	Ac
3,2,3	Ac
3,2,4	Ac
3,2,6	Ac
3,2	bDGlcp	100.9	71.5	73.5	69.0	71.8	62.2
3,3	Ac
3,4	Ac
3	bDFucp	103.5	77.9	75.3	69.4	72.1	62.5
28,6,2	Ac
28,6,3	Ac
28,6,4	Ac
28,6,6	Ac
28,6	bDGlcp	100.9	71.6	73.3	69.1	72.1	62.4
28,2	Ac
28,3	Ac
28,4	Ac
28	bDGlcp	92.0	70.7	73.3	68.9	74.0	67.6
	Subst	38.0	26.4	90.5	39.4	55.5	18.6	39.3	37.8	56.1	37.0	17.9	31.8	130.6	136.2	20.5	23.5	45.6	38.9	41.2	30.4	34.0	31.0	27.6	16.6	16.1	20.9	?	175.6	32.4	24.5


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
3,2,2	Ac
3,2,3	Ac
3,2,4	Ac
3,2,6	Ac
3,2	bDGlcp	5.23	?	?	?	?	?
3,3	Ac
3,4	Ac
3	bDFucp	4.84	?	?	?	?	?
28,6,2	Ac
28,6,3	Ac
28,6,4	Ac
28,6,6	Ac
28,6	bDGlcp	5.00	?	?	?	?	?
28,2	Ac
28,3	Ac
28,4	Ac
28	bDGlcp	6.28	?	?	?	?	?
	Subst	?	?	3.24	-	?	?	?	-	?	-	?	?	-	-	?	?	-	?	?	-	?	?	1.24	0.93	1.09	1.08	?	-	0.91	0.96


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
3,2,2	Ac
3,2,3	Ac
3,2,4	Ac
3,2,6	Ac
3,2	bDGlcp	100.9/5.23	71.5/?	73.5/?	69.0/?	71.8/?	62.2/?
3,3	Ac
3,4	Ac
3	bDFucp	103.5/4.84	77.9/?	75.3/?	69.4/?	72.1/?	62.5/?
28,6,2	Ac
28,6,3	Ac
28,6,4	Ac
28,6,6	Ac
28,6	bDGlcp	100.9/5.00	71.6/?	73.3/?	69.1/?	72.1/?	62.4/?
28,2	Ac
28,3	Ac
28,4	Ac
28	bDGlcp	92.0/6.28	70.7/?	73.3/?	68.9/?	74.0/?	67.6/?
	Subst	38.0/?	26.4/?	90.5/3.24		55.5/?	18.6/?	39.3/?		56.1/?		17.9/?	31.8/?			20.5/?	23.5/?		38.9/?	41.2/?		34.0/?	31.0/?	27.6/1.24	16.6/0.93	16.1/1.09	20.9/1.08	?/?		32.4/0.91	24.5/0.96

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
3,2,2	Ac
3,2,3	Ac
3,2,4	Ac
3,2,6	Ac
3,2	bDGlcp	5.23	?	?	?	?	?
3,3	Ac
3,4	Ac
3	bDFucp	4.84	?	?	?	?	?
28,6,2	Ac
28,6,3	Ac
28,6,4	Ac
28,6,6	Ac
28,6	bDGlcp	5.00	?	?	?	?	?
28,2	Ac
28,3	Ac
28,4	Ac
28	bDGlcp	6.28	?	?	?	?	?
	Subst	?	?	3.24		?	?	?	?	?	?	?	?	?	?	?	?	1.24	0.93	1.09	1.08	?	0.91	0.96

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
3,2,2	Ac
3,2,3	Ac
3,2,4	Ac
3,2,6	Ac
3,2	bDGlcp	100.9	71.5	73.5	69.0	71.8	62.2
3,3	Ac
3,4	Ac
3	bDFucp	103.5	77.9	75.3	69.4	72.1	62.5
28,6,2	Ac
28,6,3	Ac
28,6,4	Ac
28,6,6	Ac
28,6	bDGlcp	100.9	71.6	73.3	69.1	72.1	62.4
28,2	Ac
28,3	Ac
28,4	Ac
28	bDGlcp	92.0	70.7	73.3	68.9	74.0	67.6
	Subst	38.0	26.4	90.5	39.4	55.5	18.6	39.3	37.8	56.1	37.0	17.9	31.8	130.6	136.2	20.5	23.5	45.6	38.9	41.2	30.4	34.0	31.0	27.6	16.6	16.1	20.9	?	175.6	32.4	24.5

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

There is only one chemically distinct structure:

CC(=O)OC[C@H]1O[C@@H](O[C@@H]2[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](C)O[C@H]2O[C@H]2CC[C@@]3(C)[C@@H](CC[C@@]4(C)C5=C(CC[C@@H]43)[C@@H]3CC(C)(C)CC[C@]3(C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]4OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)CC5)C2(C)C)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

SVG MW SMILES 3D mol Ionize