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

The structure was elucidated in this paper
Publication DOI: 10.1248/cpb.46.163
Journal NLM ID: 0377775
Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Kumanoto University, Kumamoto, Japan, College of Pharmacy, Kyung-Hee University, Seul, Korea

Two new lupane-triterpene glycosides, acankoreoside A (1) and B (2), were isolated from the leaves of Acanthopanax koreanum NAKAI (Araliaceae). Based on spectroscopic data, the chemical structures of 1 and 2 were determined as 3 alpha-hydroxy-lup-20(29)-en-23,28-dioic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester and 3 alpha,11 alpha,23-trihydroxy-lup-20(29)-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, respectively.

leaf, araliaceae, Acanthopanax koreanum, lupane-triterpene glycoside, acankoreoside A and B

Structure type: oligomer ; 979.4878 [M+Na]+
C₄₈H₇₆O₁₉
Location inside paper: p. 165, Scheme, compound 1, table 1, table 2
Trivial name: acankoreoside A
Compound class: triterpene glycoside
Contained glycoepitopes: IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, GLC, extraction, optical rotation measurement, EI-MS, melting point determination, HMBC, HR-FAB-MS, TLS, aid hydrolysis

Related record ID(s): 120834
NCBI Taxonomy refs (TaxIDs): 96667
Reference(s) to other database(s): CCSD:8972, CBank-STR:21885
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
28,6,4	aLRhap	102.7	72.5	72.7	73.9	70.3	18.5
28,6	bDGlcp	105.1	75.3	76.4	78.2	77.1	61.3
28	bDGlcp	95.2	74.0	78.7	70.8	77.9	69.4
	Subst	32.9	46.2	73.0	52.0	44.9	21.8	34.5	41.8	51.0	37.4	20.9	26.0	38.3	42.9	30.1	31.9	57.0	49.7	47.4	150.8	30.8	36.9	179.0	18.0	16.8	16.7	14.8	174.9	110.0	19.4


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
28,6,4	aLRhap	5.84	4.66	4.54	4.34	4.96	1.69
28,6	bDGlcp	4.95	3.93	4.13	4.39	3.65	4.07-4.19
28	bDGlcp	6.34	4.08	4.21	4.30	4.09	4.28-4.67
	Subst	?	?	4.28	-	?	?	?	-	1.66	-	1.23-1.47	?	2.67	-	?	?	-	?	3.38	-	?	?	-	1.46	0.95	1.20	0.87	-	4.72-4.85	1.70


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
28,6,4	aLRhap	102.7/5.84	72.5/4.66	72.7/4.54	73.9/4.34	70.3/4.96	18.5/1.69
28,6	bDGlcp	105.1/4.95	75.3/3.93	76.4/4.13	78.2/4.39	77.1/3.65	61.3/4.07-4.19
28	bDGlcp	95.2/6.34	74.0/4.08	78.7/4.21	70.8/4.30	77.9/4.09	69.4/4.28-4.67
	Subst	32.9/?	46.2/?	73.0/4.28		44.9/?	21.8/?	34.5/?		51.0/1.66		20.9/1.23-1.47	26.0/?	38.3/2.67		30.1/?	31.9/?		49.7/?	47.4/3.38		30.8/?	36.9/?		18.0/1.46	16.8/0.95	16.7/1.20	14.8/0.87		110.0/4.72-4.85	19.4/1.70

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H9	H11	H12	H13	H15	H16	H18	H19	H21	H22	H24	H25	H26	H27	H29	H30
28,6,4	aLRhap	5.84	4.66	4.54	4.34	4.96	1.69
28,6	bDGlcp	4.95	3.93	4.13	4.39	3.65	4.07 4.19
28	bDGlcp	6.34	4.08	4.21	4.30	4.09	4.28 4.67
	Subst	?	?	4.28		?	?	?	1.66	1.23 1.47	?	2.67	?	?	?	3.38	?	?	1.46	0.95	1.20	0.87	4.72 4.85	1.70

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
28,6,4	aLRhap	102.7	72.5	72.7	73.9	70.3	18.5
28,6	bDGlcp	105.1	75.3	76.4	78.2	77.1	61.3
28	bDGlcp	95.2	74.0	78.7	70.8	77.9	69.4
	Subst	32.9	46.2	73.0	52.0	44.9	21.8	34.5	41.8	51.0	37.4	20.9	26.0	38.3	42.9	30.1	31.9	57.0	49.7	47.4	150.8	30.8	36.9	179.0	18.0	16.8	16.7	14.8	174.9	110.0	19.4

There is only one chemically distinct structure:

C=C(C)[C@@H]1CC[C@]2(C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](O)[C@@](C)(C(=O)O)[C@@H]5CC[C@]43C)[C@@H]12

SVG MW SMILES 3D mol Ionize

leaf, araliaceae, Acanthopanax koreanum, lupane-triterpene glycoside, acankoreoside A and B

Structure type: oligomer ; 957 [M-H]-
C₄₈H₇₈O₁₉
Location inside paper: p. 165, Scheme, compound 2, table 1, table 2
Trivial name: acankoreoside B
Compound class: triterpene glycoside
Contained glycoepitopes: IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, GLC, extraction, optical rotation measurement, EI-MS, melting point determination, HMBC, HR-FAB-MS, TLS, aid hydrolysis

Related record ID(s): 120833
NCBI Taxonomy refs (TaxIDs): 96667
Reference(s) to other database(s): CCSD:8999, CBank-STR:21886
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
28,6,4	aLRhap	102.7	72.5	72.7	73.9	70.3	18.5
28,6	bDGlcp	105.0	75.2	76.4	78.2	77.1	61.3
28	bDGlcp	95.3	74.0	78.6	70.8	78.0	69.4
	Subst	35.9	27.1	75.7	41.1	43.8	18.3	35.4	42.7	55.6	39.6	69.8	38.3	37.4	42.9	30.0	32.2	56.9	49.4	47.1	150.4	30.9	36.7	71.9	18.3	17.1	17.7	14.8	175.0	110.0	19.5


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
28,6,4	aLRhap	5.83	4.66	4.53	4.32	4.93	1.70
28,6	bDGlcp	4.94	3.94	4.15	4.39	3.67	4.11-4.19
28	bDGlcp	6.32	4.08	4.21	4.30	4.11	4.28-4.67
	Subst	?	?	3.92	-	?	?	?	-	1.92	-	4.33	?	2.98	-	?	?	-	?	3.38	-	?	?	3.67-3.88	0.83	1.29	1.25	1.00	-	4.61-4.80	1.64


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
28,6,4	aLRhap	102.7/5.83	72.5/4.66	72.7/4.53	73.9/4.32	70.3/4.93	18.5/1.70
28,6	bDGlcp	105.0/4.94	75.2/3.94	76.4/4.15	78.2/4.39	77.1/3.67	61.3/4.11-4.19
28	bDGlcp	95.3/6.32	74.0/4.08	78.6/4.21	70.8/4.30	78.0/4.11	69.4/4.28-4.67
	Subst	35.9/?	27.1/?	75.7/3.92		43.8/?	18.3/?	35.4/?		55.6/1.92		69.8/4.33	38.3/?	37.4/2.98		30.0/?	32.2/?		49.4/?	47.1/3.38		30.9/?	36.7/?	71.9/3.67-3.88	18.3/0.83	17.1/1.29	17.7/1.25	14.8/1.00		110.0/4.61-4.80	19.5/1.64

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H9	H11	H12	H13	H15	H16	H18	H19	H21	H22	H23	H24	H25	H26	H27	H29	H30
28,6,4	aLRhap	5.83	4.66	4.53	4.32	4.93	1.70
28,6	bDGlcp	4.94	3.94	4.15	4.39	3.67	4.11 4.19
28	bDGlcp	6.32	4.08	4.21	4.30	4.11	4.28 4.67
	Subst	?	?	3.92		?	?	?	1.92	4.33	?	2.98	?	?	?	3.38	?	?	3.67 3.88	0.83	1.29	1.25	1.00	4.61 4.80	1.64

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
28,6,4	aLRhap	102.7	72.5	72.7	73.9	70.3	18.5
28,6	bDGlcp	105.0	75.2	76.4	78.2	77.1	61.3
28	bDGlcp	95.3	74.0	78.6	70.8	78.0	69.4
	Subst	35.9	27.1	75.7	41.1	43.8	18.3	35.4	42.7	55.6	39.6	69.8	38.3	37.4	42.9	30.0	32.2	56.9	49.4	47.1	150.4	30.9	36.7	71.9	18.3	17.1	17.7	14.8	175.0	110.0	19.5

There is only one chemically distinct structure:

C=C(C)[C@@H]1CC[C@]2(C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]3(C)[C@H](C[C@@H](O)[C@@H]4[C@@]5(C)CC[C@@H](O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]12

SVG MW SMILES 3D mol Ionize