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

The structure was elucidated in this paper
NCBI PubMed ID: 9548865
Publication DOI: 10.1021/np970449e
Journal NLM ID: 7906882
Publisher: American Society of Pharmacognosy
Correspondence: Kang SS <sskang

plaza.snu.ac.kr>
Institutions: Natural Products Research Institute, Seoul National University, Seoul, South Korea, College of Pharmacy, Chungnam National University, Taejeon, South Korea

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.

extraction, plant, azukisaponin, Lathyrus japonicus

Structure type: oligomer
Location inside paper: p. 299, compound 1
Trivial name: Azukisaponin II, azukisaponin II
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_423153,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, extraction, column chromatography, melting point determination, HMBC, HMQC, DEPT, 1H NMR COSY, optical rotation measuremnt

Related record ID(s): 61466, 61467
NCBI Taxonomy refs (TaxIDs): 154493
Reference(s) to other database(s): CCSD:9280, CBank-STR:22157
Show glycosyltransferases

There is only one chemically distinct structure:

CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@](C)(CO)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C)[C@H](O)C1

SVG MW SMILES 3D mol Ionize

plaza.snu.ac.kr>
Institutions: Natural Products Research Institute, Seoul National University, Seoul, South Korea, College of Pharmacy, Chungnam National University, Taejeon, South Korea

extraction, plant, azukisaponin, Lathyrus japonicus

Structure type: oligomer
Location inside paper: p. 299, compound 2
Trivial name: azukisaponin V, dehydrosoyasaponin I, azukisaponin, kaikasaponin
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, extraction, column chromatography, melting point determination, HMBC, HMQC, DEPT, 1H NMR COSY, optical rotation measuremnt

Related record ID(s): 61465, 61467
NCBI Taxonomy refs (TaxIDs): 154493
Reference(s) to other database(s): CCSD:9282, CBank-STR:22158
Show glycosyltransferases

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@@H]3[C@@H](O)[C@H](O)[C@@H](C(=O)O)O[C@H]3O[C@H]3CC[C@@]4(C)[C@@H](CC[C@]5(C)[C@@H]4CC=C4[C@@H]6CC(C)(C)C[C@@H](O)[C@]6(C)CC[C@]45C)[C@@]3(C)CO)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

plaza.snu.ac.kr>
Institutions: Natural Products Research Institute, Seoul National University, Seoul, South Korea, College of Pharmacy, Chungnam National University, Taejeon, South Korea

extraction, plant, azukisaponin, Lathyrus japonicus

Structure type: oligomer ; 973 [M+H]+
Location inside paper: p. 299, compound 3
Trivial name: lanthyrus saponin
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_140628,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_423153,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, extraction, column chromatography, melting point determination, HMBC, HMQC, DEPT, 1H NMR COSY, optical rotation measuremnt

Related record ID(s): 61465, 61466
NCBI Taxonomy refs (TaxIDs): 154493
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
3,2,2	bDGlcp	106.8	77.0	77.6	69.4	78.1	61.2
3,2	bDGlcp	103.5	85.9	77.6	71.5	79.5	62.8
3	bDGlcpA	104.7	82.2	77.2	72.1	77.2	170.3
	xXSoyasapogenolB	?	?	90.7	?	?	?	?	?	?	?	?	122.4	144.9	?	?	?	?	?	?	?	?	75.6	?	63.4	?	?	?	?	?	?


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	bDGlcp	5.22	?	?	?	3.65	?
3,2	bDGlcp	5.58	?	?	?	3.97	?
3	bDGlcpA	5.05	?	4.67	?	4.57	-
	xXSoyasapogenolB	?	?	3.43	-	?	?	?	-	?	-	?	5.30	-	-	?	?	-	2.39	?	-	?	3.74	?	3.37	?	?	?	?	?	?


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	bDGlcp	106.8/5.22	77.0/?	77.6/?	69.4/?	78.1/3.65	61.2/?
3,2	bDGlcp	103.5/5.58	85.9/?	77.6/?	71.5/?	79.5/3.97	62.8/?
3	bDGlcpA	104.7/5.05	82.2/?	77.2/4.67	72.1/?	77.2/4.57	
	xXSoyasapogenolB	?/?	?/?	90.7/3.43		?/?	?/?	?/?		?/?		?/?	122.4/5.30			?/?	?/?		?/2.39	?/?		?/?	75.6/3.74	?/?	63.4/3.37	?/?	?/?	?/?	?/?	?/?	?/?

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	H28	H29	H30
3,2,2	bDGlcp	5.22	?	?	?	3.65	?
3,2	bDGlcp	5.58	?	?	?	3.97	?
3	bDGlcpA	5.05	?	4.67	?	4.57
	xXSoyasapogenolB	?	?	3.43		?	?	?	?	?	5.30	?	?	2.39	?	?	3.74	?	3.37	?	?	?	?	?	?

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	bDGlcp	106.8	77.0	77.6	69.4	78.1	61.2
3,2	bDGlcp	103.5	85.9	77.6	71.5	79.5	62.8
3	bDGlcpA	104.7	82.2	77.2	72.1	77.2	170.3
	xXSoyasapogenolB	?	?	90.7	?	?	?	?	?	?	?	?	122.4	144.9	?	?	?	?	?	?	?	?	75.6	?	63.4	?	?	?	?	?	?

The spectrum also has 25 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]6O[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)[C@](C)(CO)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C)[C@H](O)C1

SVG MW SMILES 3D mol Ionize