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1. (Article ID: 12460)
Matsuda H, Murakami T, Nishida N, Kageura T, Yoshikawa M
Medicinal foodstuffs. XX. Vasorelaxant active constituents from the roots of Angelica furcijuga Kitagawa: structures of hyuganins A, B, C, and D
Chemical and Pharmaceutical Bulletin 48(10) (2000)
1429-1435
From the methanolic extract with vasorelaxant activity obtained from Angelica furcijuga KITAGAWA, four new khellactone-type coumarins, hyuganins A, B, C, and D, were isolated together with twelve known coumarins, two known acetylenic compounds, and a known lignan. The structures of hyuganins A, B, C, and D were determined on the basis of chemical and physicochemical evidence. Nine principal coumarins (hyuganin A, anomalin, pteryxin, isopteryxin, isoepoxypteryxin, praerosides II and IV, apiosylskimmin, (R)-peucedanol 7-O-β-D-glucopyranoside), two acetylenic compounds [(-)-falcarnol and falcarindiol], and related compounds were examined for inhibitory activities on high concentration of K+ (High K+)- and dl-norepinephrine (NE)-induced contractions. The results indicate that the 3'-and 4'-acyl groups of khellactone-type coumarins are essential for the inhibitory activity on the contractions by High K+. Hyuganin A and anomalin showed inhibitory effects on High K+-induced contraction, but not on NE-induced contraction. Other active coumarins (pteryxin, isopteryxin, isoepoxypteryxin) and an acetylenic compound (falcarindiol) non-selectively inhibited both contractions by High K+ and NE.
hyuganin, vasorelaxant activity, khellactone, Angelica furcijuga, coumarin, structural requirement
NCBI PubMed ID: 11045445Publication DOI: 10.1248/cpb.48.1429Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: Yoshikawa M
mb.kyoto-phu.ac.jp>
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan
The publication contains the following compound(s):
- Compound ID: 22478
|
b-D-Glcp-(1-4')-Subst
Subst = (+)-pinoresinol = SMILES O{54}C1=C(OC)C=C([C@@H]2[C@@]3([H])CO[C@H](C4=CC(OC)={104}C(O)C=C4)[C@@]3([H])CO2)C=C1 |
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Structure type: monomer
C26H32O11
Compound class: glycoside, lignan, lignan glycoside
- Compound ID: 26315
|
b-D-Glcp-(1-7)-Subst
Subst = (R)-peucedanol = SMILES C{53}C({52}[C@H](O)CC1={7}C(O)C=C2C(C=CC(O2)=O)=C1)(O)C |
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Structure type: monomer
Trivial name: (R)-peucedanol 7-O-β-D-glucopyranoside
Compound class: glycoside, coumarin glycoside
Reference(s) to other database(s): CCSD:
39036, CBank-STR:997
- Compound ID: 29373
|
b-D-Glcp-(1-3')-Subst
Subst = (+)-cis-khellactone = SMILES CC3(C)Oc2ccc1ccc(=O)oc1c2{54}[C@@H](O){53}[C@H]3O |
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Structure type: monomer
Trivial name: praeroside II
Compound class: glycoside
- Compound ID: 29374
|
b-D-Glcp-(1-3')-Subst
Subst = jatamansinol = SMILES CC3(C)Oc2ccc1ccc(=O)oc1c2C{53}[C@H]3O |
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Structure type: monomer
Trivial name: praeroside IV
Compound class: glycoside
- Compound ID: 32324
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b-D-Apif-(1-6)-b-D-Glcp-(1-7)-Subst
Subst = 7-hydroxycoumarin = SMILES C1=C{7}C(=CC2=C1C=CC(=O)O2)O |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 32325
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b-D-Apif-(1-6)-b-D-Glcp-(1-7)-Subst6Me
Subst = cichorigenin = SMILES O{7}C(C=C(OC1=O)C(C=C1)=C2)={6}C2O |
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Structure type: monomer
Compound class: glycoside
- Compound ID: 32326
|
b-D-Glcp-(1-4')-Subst
Subst = marmesinine aglycon = SMILES O{54}C(C)(C)[C@@H](C1)CC(C1=C2)=CC3=C2OC(C=C3)=O |
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Structure type: monomer
Trivial name: marmesinin
Compound class: glycoside
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