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1. (Article ID: 11829)
Miyakoshi M, Shirasuna K, Hirai Y, Shingu K, Isoda S, Shoji J, Ida Y, Shimizu T
Triterpenoid saponins of Acanthopanax nipponicus leaves
Journal of Natural Products 62(3) (1999)
445-448
Five new triterpenoid saponins, nipponosides A−E (1, 3−6), were isolated from Acanthopanax nipponicus leaves, along with a known saponin, kalopanaxsaponin G (2). Nipponosides A−E were characterized as the 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester of 3-oxohederagenin, oleanolic acid 3-O-β-D-glucopyranoside, gypsogenin 3-O-β-D-glucopyranoside, 3β,23,29-trihydroxyolean-12-en-28-oic acid, and 3β,20α,23-trihydroxy-30-nor-olean-12-en-28-oic acid, respectively. The structures of these new compounds were based on chemical and spectral methods.
triterpenoid saponin, Acanthopanax nipponicus, nipponosides A-E, kalopanaxsaponin G
NCBI PubMed ID: 10096855Publication DOI: 10.1021/np9804334Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: Ida Y
pharm.showa-u.ac.jp>
Institutions: School of Pharmaceutical Sciences, Showa University, Hatanodai 1-5-8, Shinagawa-ku, Tokyo 142-8555, Japan, okyo Metropolitan Medicinal Plant Garden, Nakajima-cho 21-1, Kodaira, Tokyo 187-0033, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, GLC, optical rotation measurement, reduction with NaBH4, HMBC, HMQC, COSY, HCl hydrolysis, trimethylsilylation
The publication contains the following compound(s):
- Compound ID: 30591
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = 3-oxohederagenin = SMILES CC5(C)CC[C@]4({28}C(=O)O)CC[C@]3(C)/C(=C\C[C@@H]2[C@@]1(C)CCC(=O)[C@@](C)({23}CO)[C@@H]1CC[C@]23C)C4C5 |
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Structure type: oligomer
; 939 [M-H]-
C48H76O18
Trivial name: nipponoside A
Compound class: saponin glycoside
- Compound ID: 30592
Structure type: oligomer
; 941 [M-H]-
Trivial name: kalopanaxsaponin G
Compound class: saponin glycoside
- Compound ID: 30593
|
b-D-Glcp-(1-3)-+
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Oleanolic |
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Structure type: oligomer
; 1087 [M-H]-
C54H88O22
Trivial name: nipponoside B
Compound class: saponin glycoside
- Compound ID: 30594
Structure type: oligomer
; 617 [M-H]-
Compound class: saponin glycoside
- Compound ID: 30595
|
b-D-Glcp-(1-3)-+
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = gypsogenin = SMILES C[C@@]1(C=O){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@@]5([H])CC(C)(C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CCC12 |
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Structure type: oligomer
; 1101 [M-H]-
C54H86O23
Trivial name: nipponoside C
Compound class: saponin glycoside
- Compound ID: 30596
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = 3α,23,29-trihydroxyolean-12-en-28-oic acid = SMILES C[C@]1({29}CO)CC[C@]2({28}C(=O)O)CC[C@]3(C)C(=CCC4[C@@]5(C)CC{3}[C@H](O)[C@@](C)({23}CO)C5CC[C@]43C)C2C1 |
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Structure type: oligomer
; 957 [M-H]-
C48H77O19
Trivial name: nipponoside D
Compound class: saponin glycoside
- Compound ID: 30597
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = 3β,20α,23-trihydroxy-30-nor-olean-12-en-28-oic acid = SMILES C{20}[C@]1(O)CC[C@]2({28}C(=O)O)CC[C@]3(C)C(=CCC4[C@@]5(C)CC{3}[C@H](O)[C@@](C)({23}CO)C5CC[C@]43C)C2C1 |
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Structure type: oligomer
; 943 [M-H]-
C47H76O19
Trivial name: nipponoside E
Compound class: saponin glycoside
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