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1. (Article ID: 11399)
Capasso A, Balderrama L, Sivila SC, De Tommasi N, Sorrentino L, Pizza C
Phytochemical and pharmacological studies of Guettarda acreana
Planta Medica 64(4) (1998)
348-352
The present study examines the effects of the extracts [petroleum ether, CHCl3, CHCl3/MeOH (9:1) and MeOH], partially purified fractions and pure compounds from Guettarda acreana on the electrically induced contractions (E.C.I.) of the isolated guinea-pig ileum. The results of the experiments indicate that CHCl3/MeOH (9:1), MeOH extract, and the MeOH soluble part from CHCl3/MeOH extract tested at concentrations of 1.2, 2.5, and 5 micrograms/ml, dose-dependently reduced the guinea-pig ileum contractions. Furthermore, some partially purified fractions I-IV from the MeOH extract, each tested at the same concentrations of the extracts, and some pure compounds (6 x 10(-6), 3 x 10(-6), 1 x 10(-6) M) isolated from the above fractions significantly reduced, in a dose-dependent manner, the electrical contractions of the ileum. The active compounds were identified as the known indole alkaloids strictosidic acid, lyalosidic acid, 5 alpha-carboxystrictosidine, strictosidine, and sickingine, as well as the known quinic acid derivatives 5-caffeoylquinic acid, 4,5-dicaffeoylquinic acid, and shikimic acid by spectral data. Two known quinovic acid glycosides and a new triterpenic glycoside, quinovic acid 3 beta-O-alpha-rhamnopyranosyl-(1-->3)-(beta-glucopyranosyl-(1-->6)-beta- glucopyranoside, were also isolated and their structures established by NMR and M5 data.
Rubiaceae, quinovic acid glycosides, indole alkaloids, Guettarda acreana, qunic acid derivatives, electrical contractions, guinea-pig ileum, antispasmodic
NCBI PubMed ID: 9619119Publication DOI: 10.1055/s-2006-957449Journal NLM ID: 0066751Publisher: George Thieme
Correspondence: Capasso A
ponza.dia.unisa.it>
Institutions: UMSA, Universidad Mayor de San Andres, Campus Universitario, La Paz, Bolivia, Dipartimento Scienze Farmaceutiche, Salerno, Italy, Dipartimento di Farmacologia Sperimentale, Università degli Studi di Napoli ''Federico II'', Napoli, Italy
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, HPLC, extraction, optical rotation measurement, CC, biological assay, DEPT, COSY, HOHAHA, HETCOR, COLOC
The publication contains the following compound(s):
- Compound ID: 28991
|
b-D-Glcp-(1-19)-Subst23(%)Me
Subst = strictosidinic acid aglycon = SMILES C=C[C@@H]1[C@H](C[C@H]2C3=C(C4=CC=CC=C4N3)CCN2)C({23}C(O)=O)=CO{19}[C@H]1O |
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Structure type: monomer
Trivial name: strictosidinic acid, strictosidine
Compound class: glycoside
- Compound ID: 28992
|
b-D-Glcp-(1-19)-Subst
Subst = lyalosidic acid aglycon = SMILES C=C[C@@H]1[C@H](CC2=NC=CC3=C2NC4=CC=CC=C34)C({23}C(O)=O)=CO{19}[C@H]1O |
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Structure type: monomer
Trivial name: lyalosidic acid
Compound class: glycoside
- Compound ID: 28993
|
b-D-Glcp-(1-19)-Subst
Subst = 5α-carboxystrictosidine aglycon = SMILES COC(C1=CO{19}[C@@H](O)C(C=C)C1C[C@H]2C3=C(C4=CC=CC=C4N3)CC({24}C(O)=O)N2)=O |
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Structure type: monomer
Trivial name: 5α-carboxystrictosidine
Compound class: glycoside
- Compound ID: 28994
|
b-D-Glcp-(1-19)-Subst
Subst = sickingine aglycon = SMILES C=C[C@@H]1[C@@H]2C[C@H]3C4=C(C5=CC=CC=C5N4)C[C@@H]({24}C(O)=O)N3CC2=CO{19}[C@H]1O |
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Structure type: monomer
Trivial name: sickingine
Compound class: glycoside
- Compound ID: 28995
|
b-D-Glcp-(1-6)-+
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a-L-Rhap-(1-3)-b-D-Glcp-(1-3)-Subst-(?--/C48H76O19/
Subst = quinovic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@]({27}C(O)=O)4[C@@](C)3CCC2C1(C)C |
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Structure type: oligomer
; 955 [M-H]-
Aglycon: C48H76O19
Compound class: triterpenoid glycoside
- Compound ID: 28996
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b-D-Fucp-(1-3)-+
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?%b-D-Glcp-(1-27)-Subst
Subst = quinovic acid = SMILES O{3}[C@H]1CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@]({27}C(O)=O)4[C@@](C)3CCC2C1(C)C |
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Structure type: oligomer
Compound class: triterpenoid glycoside
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