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1. (Article ID: 11317)
Takasaki M, Yamauchi I, Haruna M, Konoshima T
New glycosides from Ajuga decumbens
Journal of Natural Products 61(9) (1998)
1105-1109
A new phenethyl alcohol glycoside, galactosylmartynoside (1), and a new abietatriene-type diterpene glycoside, ajugaside A (2), were isolated from the whole plants of Ajuga decumbens, together with known phenethyl alcohol glycosides (3 and 4) and iridoid glycosides (5-7). Chemical structures were elucidated on the basis of spectral data. Of these compounds, 8-acetylharpagide (6) exhibited the strongest inhibitory effect on Epstein-Barr virus activation induced by 12-O-tetradecanoylphorbol-13-acetate.
diterpenes, phenylpropanoid glycosides, tumor-promoting activities
NCBI PubMed ID: 9748375Publication DOI: 10.1021/np980148kJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Institutions: Faculty of Pharmacy, Meijo University, Nagoya, Japan, Kyoto Pharmaceutical University, Kyoto, Japan
Methods: 13C NMR, 1H NMR, NOE, IR, acid hydrolysis, HPLC, UV, extraction, optical rotation measurement, CC, melting point determination, HMBC, antitumor activity assay, DEPT, COSY, HOHAHA, HSQC, HR-FAB-MS
The publication contains the following compound(s):
- Compound ID: 28597
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Caf3Me-(9-4)-+
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b-D-Galp-(1-2)-a-L-Rhap-(1-3)-b-D-Glcp-(1-8)-3,4,8HOPhet-(4-1)-Me |
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Structure type: oligomer
; 815.2973
C37H50O20
Trivial name: galactosylmartynoside
Compound class: glycoside
- Compound ID: 28598
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Caf3Me-(9-4)-+
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a-L-Rhap-(1-3)-b-D-Glcp-(1-8)-3,4,8HOPhet-(4-1)-Me |
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Structure type: oligomer
Trivial name: martynoside
Compound class: glycoside, phenylpropanoid glycoside
- Compound ID: 28599
Structure type: oligomer
Trivial name: darendoside B
Compound class: glycoside
- Compound ID: 28600
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b-D-Glcp-(1-19)-+
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b-D-Glcp-(1-14)-Subst
Subst = 1,2,14,19-tetrahydroxyabietatriene = SMILES CC(C1={2}C(O){1}C(O)=C2[C@@]3(C)CCC{14}[C@](C)(O)C3CCC2=C1){19}CO |
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Structure type: oligomer
; 659.3287
C32H50O14
Trivial name: ajugaside A
Compound class: glycoside
- Compound ID: 28601
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b-D-Glcp-(1-14)-Subst
Subst = 1,2,14,19-tetrahydroxyabietatriene = SMILES CC(C1={2}C(O){1}C(O)=C2[C@@]3(C)CCC{14}[C@](C)(O)C3CCC2=C1){19}CO |
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Structure type: monomer
; 519.2570 [M+Na]+
C26H40O9
Compound class: glycoside
- Compound ID: 28602
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b-D-Glcp-(1-1)-Subst
Subst = reptoside aglycon = SMILES CC1C{8}[C@](C)(O)C2{1}[C@H](O)O/C=C\{5}[C@@]12O |
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Structure type: monomer
C26H40O9
Trivial name: reptoside
Compound class: glycoside, iridoid glycoside
- Compound ID: 28603
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b-D-Glcp-(1-1)-Subst8Ac
Subst = harpagide aglycon = SMILES O{1}[C@H]1[C@@]2([H]){5}[C@@]({6}[C@H](O)C{8}[C@]2(C)O)(O)C=CO1 |
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Structure type: monomer
C26H40O9
Trivial name: 8-acetylharpagide, 8-acetylharpgide, harpagide, 8-O-acetylharpagid, 8-O-acetylharpagide
Compound class: glycoside, iridoid glycoside
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2. (Article ID: 12313)
Konoshima T, Takasaki M, Tokuda H, Nishino H
Cancer chemopreventive activity of an iridoid glycoside, 8-acetylharpagide, from Ajuga decumbens
Cancer Letters 157(1) (2000)
87-92
In the course of our continuing search for novel cancer chemopreventive agents from natural sources, several kinds of Labiatae plants were screened. Consequently, the iridoid glycoside derivative, 8-acetylharpagide (8-AcHarp), was obtained from the flowering whole plant of Ajuga decumbens as an active constituent. This glycoside exhibited the remarkable inhibitory effect on two-stage carcinogenesis test of mouse skin tumors induced by nitric oxide (NO) donor, (+/-)-(E)-methyl-2-[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexen eamide (NOR 1) as an initiator and 12-O-tetradecanoylphorbol-13-acetate (TPA) as a promoter. Further, 8-AcHarp exhibited potent anti-tumor-promoting activity on two-stage carcinogenesis test of mouse hepatic tumor using N-nitrosodiethylamine (DEN) as an initiator and phenobarbital (PB) as a promoter.
cancer chemopreventive activity, 8-acetylharpagide, Ajuga decumbens, nitric oxide donor, (±)-(E)-Methyl-2-[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexeneamide, hepatic tumor inhibitor
NCBI PubMed ID: 10893446Publication DOI: 10.1016/s0304-3835(00)00479-1Journal NLM ID: 7600053Publisher: Limerick: Elsevier Science Ireland
Correspondence: konosima
mb.kyoto-phu.ac.jp
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan, Kyoto Prefectural University of Medicine, Kyoto, Japan
The publication contains the following compound(s):
- Compound ID: 28602
|
b-D-Glcp-(1-1)-Subst
Subst = reptoside aglycon = SMILES CC1C{8}[C@](C)(O)C2{1}[C@H](O)O/C=C\{5}[C@@]12O |
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Structure type: monomer
C26H40O9
Trivial name: reptoside
Compound class: glycoside, iridoid glycoside
- Compound ID: 28603
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b-D-Glcp-(1-1)-Subst8Ac
Subst = harpagide aglycon = SMILES O{1}[C@H]1[C@@]2([H]){5}[C@@]({6}[C@H](O)C{8}[C@]2(C)O)(O)C=CO1 |
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Structure type: monomer
C26H40O9
Trivial name: 8-acetylharpagide, 8-acetylharpgide, harpagide, 8-O-acetylharpagid, 8-O-acetylharpagide
Compound class: glycoside, iridoid glycoside
- Compound ID: 30017
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b-D-Glcp-(1-1)-Subst
Subst = harpagide aglycon = SMILES O{1}[C@H]1[C@@]2([H]){5}[C@@]({6}[C@H](O)C{8}[C@]2(C)O)(O)C=CO1 |
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Structure type: monomer
Trivial name: harpagide
Compound class: glycoside, iridoid glycoside
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