RESUMO
Two novel steroids with a cyclopropane ring at C-25 and C-26, 7-oxopetrosterol (1) and 7alpha-hydroxypetrosterol (2), along with two known compounds, petrosterol (3) and 23,24-dihydrocalysterol (4), have been isolated from the Japanese marine sponge Strongylophora corticata. The structures of 1 and 2 were determined as 26, 27-cyclo-24,27-dimethyl-3beta-hydroxycholest-5-en-7-one and 26, 27-cyclo-24,27-dimethylcholest-5-en-3beta,7alpha-diol on the basis of spectroscopic investigations.
Assuntos
Colestanóis/isolamento & purificação , Colestenonas/isolamento & purificação , Poríferos/química , Esteroides/isolamento & purificação , Animais , Clorofórmio , SolventesRESUMO
Two novel steroids, polasterol A (1) and polasterol B sulfate (2), along with two known compounds, 22(E),24-isopropylcholesta-5, 22-dien-3 beta-ol (3) and halistanol sulfate (4), have been isolated from the Japanese marine sponge Epipolasis sp. The structures of 1 and 2 were determined as 3 beta-hydroxy-24-isopropylcholesta-5, 22(E)-dien-7-one and 24xi-isopropenylcholesta-22(Z), 28(29)-diene-2 beta,3 alpha,6 alpha-triyl trisodium sulfate on the basis of spectroscopic investigations and a chemical conversion.
Assuntos
Colesterol/análogos & derivados , Poríferos/química , Animais , Colesterol/química , Colesterol/isolamento & purificação , Cromatografia em Gel , Cromatografia Gasosa-Espectrometria de Massas , Japão , Espectroscopia de Ressonância Magnética , Rotação Ocular , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta , Esteroides/química , Esteroides/isolamento & purificaçãoRESUMO
A new bromopyrrole alkaloid (1) along with (+/-)-2 and (+/-)-longamide (3) has been isolated from the Japanese marine sponge Homaxinella sp. The structures of the compounds were proposed on the basis of spectroscopic data. The optical resolution of (+/-)-2 by chiral HPLC was successful and afforded the two enantiomers, (+)-2 and (-)-2.
RESUMO
Two novel diterpenes, peroxypolasol (1) and mugipolasol (2), have been isolated from the Japanese marine sponge Epipolasis sp. The structures of 1 and 2 were determined on the basis of spectroscopic data. Compound 1 is a diterpene with a peroxide ring in the side chain, and 2 is an unusual six/five-membered ring diterpene with an ethyl unit at C-2.
RESUMO
Three new diterpenes, polasols A-C (1-3), have been isolated from the Japanese marine sponge Epipolasis sp. The structures of 1-3 were assigned primarily by 2D NMR methods.
Assuntos
Diterpenos/química , Poríferos/química , Animais , Cromatografia Líquida de Alta Pressão , Diterpenos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Conformação Molecular , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
Penasterol and penasterone, constituents of the Okinawan marine sponge Penares incrustans, dose-dependently inhibited anti-IgE-induced histamine release from rat mast cells. The concentrations of penasterol and penasterone required for 50% inhibition of anti-IgE-induced histamine release (IC50) were 0.5 and 1.5 microM, respectively. Both compounds dose-dependently inhibited phospholipase A2 (PLA2) activity. Moreover, they inhibited anti-IgE-induced [3H]arachidonic acid from rat mast cells. These results suggest that the mechanism of inhibition by these compounds of the histamine release induced by anti-IgE was through the inhibition of PLA2.
Assuntos
Liberação de Histamina/efeitos dos fármacos , Imunoglobulina E/fisiologia , Lanosterol/análogos & derivados , Mastócitos/metabolismo , Animais , Ácidos Araquidônicos/metabolismo , Liberação de Histamina/fisiologia , Técnicas In Vitro , Lanosterol/farmacologia , Masculino , Mastócitos/efeitos dos fármacos , Mastócitos/enzimologia , Fosfolipases A/metabolismo , Fosfolipases A2 , Ratos , Ratos WistarRESUMO
From the herb of Anagallis arvensis, we have isolated four novel oleanane glycosides, anagallosaponins VI-IX, and two artifact saponins, apoanagallosaponins III and IV, formed from anagallosaponins III and IV. The structures were elucidated by chemical and spectral methods, 2D NMR techniques being particularly helpful. The structures of anagallosaponins VI and VII were characterized as priverogenin B 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside and 3-O-(beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2)]beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside), respectively. The structures of anagallosaponins VIII and IX were characterized as 23-hydroxypriverogenin B 22-acetate 3-O-(beta-D-xylopyranosyl (1-->2)-O-beta-D-glucopyranosyl (1-->4)[beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside), 3-O-(beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2)]beta-D-glucopyranosyl (1-->4)[beta-D-glucopyranosyl (1-->2)]- alpha-L-arabinopyranoside), respectively. The structures of apoanagallosaponins III and IV were characterized as camelliagenin A 16-acetate 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-alpha-L-arabnopyranoside, 3-O-(beta-D-xylopyranosyl (1-->2)-O-beta-D-glucopyranosyl (1-->4)[beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside), respectively.
Assuntos
Plantas Medicinais/química , Saponinas/química , Saponinas/isolamento & purificação , Configuração de Carboidratos , Sequência de Carboidratos , Glicosídeos/química , Glicosídeos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Triterpenos/química , Triterpenos/isolamento & purificaçãoRESUMO
From the seeds of Impatiens balsamina have been isolated four rare baccharane glycosides, hosenkosides L-O. The structures of all isolates were secured by the use of 2D NMR techniques (1H-1H COSY, HMQC, HMBC, ROESY) and chemical derivatization. Hosenkosides L and M are hosenkol A 3-O-sambubiosyl-28-O-glucoside and 3-O-sambubiosyl-26-O-glucosyl-28-O-glucoside, respectively. Hosenkoside N is hosenkol C 3-O-glucosyl-28-O-glucoside. Hosenkoside O is hosenkol D 3-O-sophorosyl-28-O-glucoside.
Assuntos
Glicosídeos/química , Glicosídeos/isolamento & purificação , Plantas Medicinais/química , Saponinas/química , Saponinas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Sementes/químicaRESUMO
From the herb of Anagallis arvensis L., we have isolated five novel oleanane glycosides, anagallosaponins I-V and the artifact, methyl anagallosaponin I, besides anagallosides A, B, C, and desglucoanagallosides A and B. The structures of isolates were identified by the use of 2D-NMR techniques (1H-1H correlation spectroscopy (COSY), 1H-detected heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple quantum coherence (HMBC), rotating frame Overhauser enhancement spectroscopy (ROESY), total correlation spectroscopy (TOCSY). The structures of anagallosaponins I and II were characterized as anagallogenin A. 3-O-(beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2)-] beta-D-glucopyranosyl (1-->4)- [beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside) and anagallogein A 22-acetate 3-O-(beta-D-xylopyranosyl (1-->2)-O-beta-D- glucopyranosyl (1-->4)-[beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside), respectively. The structures of anagallosaponins III, IV and V were characterized as priverogenin B 22-acetate 3-O-beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside, 3-O-(beta-D-xylopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-[beta-D-glucopyranosyl (1-->2)]-alpha-L-arabinopyranoside), 3-O-(beta-D-glucopyranosyl (1-->4)-[beta-D-xylopyranosyl (1-->2)]-beta-D-glucopyranosyl (1-->4)-alpha-L-arabinopyranoside), respectively. Methyl anagallosaponin I, the methylacetal of anagallosaponin I might be derived from anagallosaponin I during the isolation procedure.
Assuntos
Extratos Vegetais/química , Plantas Medicinais/química , Saponinas/química , Configuração de Carboidratos , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Dados de Sequência MolecularRESUMO
From the seeds of Impatiens balsamina we have isolated six novel baccharane glycosides, hosenkosides F-K. The structures of all isolates were determined by the use of two dimensional (2D) NMR techniques (1H-1H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC), rotating frame Overhauser enhancement spectroscopy (ROESY), total correlation spectroscopy (TOCSY)) and chemical derivatization. Hosenkosides F, H and I are hosenkol B 3-O-sambubiosido-26-O-glucoside, 3-O-sambubioside and 3,26-O-diglucoside, respectively. Hosenkoside G is hosenkol C 3-O-sambubiosido-28-O-glucoside. Hosenkosides J and K are hosenkol A 3-O-sophoroside and 3-O-sophorosido-26-O-glucosyl-28-O-glucoside, respectively.
Assuntos
Glicosídeos/isolamento & purificação , Plantas/química , Saponinas/isolamento & purificação , Compostos de Espiro/isolamento & purificação , Sequência de Carboidratos , Glicosídeos/química , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Saponinas/farmacologia , Compostos de Espiro/farmacologiaRESUMO
A new polyhydroxylated steroid (24-methylene-1 alpha, 3 beta, 11 alpha-trihydroxycholest-5-ene-18-oic acid-3-acetate, 1) and known related compounds (2-4) from the soft coral Sinularia abrupta have potently inhibited histamine release from rat peritoneal mast cells induced by anti-immunoglobulin E. The inhibitory effect of 1 was approximately 6500 times stronger than that of disodium cromoglycate, a well-known antiallergic drug.
Assuntos
Cnidários/química , Liberação de Histamina/efeitos dos fármacos , Esteróis/isolamento & purificação , Esteróis/farmacologia , Animais , Anticorpos Anti-Idiotípicos/farmacologia , Colestenos/isolamento & purificação , Colestenos/farmacologia , Antagonistas dos Receptores Histamínicos/isolamento & purificação , Antagonistas dos Receptores Histamínicos/farmacologia , Hidroxilação , Masculino , Mastócitos/efeitos dos fármacos , Mastócitos/metabolismo , Ratos , Ratos WistarRESUMO
Histamine release from rat peritoneal mast cells induced by anti-IgE was essentially complete within 4-5 min. Xestobergsterol A and B, which are constituents of the Okinawan marine sponge Xestospongia bergquistia Fromont, dose-dependently inhibited anti-IgE-induced histamine release from rat mast cells. The IC50 values of xestobergsterol A and B for histamine release in mast cells activated by anti-IgE were 0.07 and 0.11 microM, respectively. Anti-IgE stimulated PI-PLC activity in a mast cell membrane preparation. Xestobergsterol A dose-dependently inhibited the generation of IP3 and membrane-bound PI-PLC activity. Moreover, xestobergsterol A inhibited Ca(2+)-mobilization from intracellular Ca(2+)-stores as well as histamine release in mast cells activated by anti-IgE. On the other hand, xestobergsterol B did not inhibit the membrane-bound and cytosolic PI-PLC activity, IP3 generation or the initial rise in [Ca2+]i in mast cells activated by anti-IgE. These results suggest that the mechanism of inhibition by xestobergsterol A of the initial rise in [Ca2+]i, of the generation of IP3, and of histamine release induced by anti-IgE, was through the inhibition of PI-PLC activity.
Assuntos
Colestanonas/farmacologia , Cnidários/química , Liberação de Histamina/efeitos dos fármacos , Imunoglobulina E/imunologia , Animais , Cálcio/fisiologia , Técnicas In Vitro , Inositol 1,4,5-Trifosfato/metabolismo , Cinética , Masculino , Cavidade Peritoneal/citologia , Ratos , Ratos Wistar , Fosfolipases Tipo C/metabolismoRESUMO
6-Tridecylresorcylic acid (TRA) caused histamine release from rat peritoneal mast cells in a dose-dependent manner. The release of histamine by TRA was also time dependent. On the other hand, high K+ (150 mM) strongly inhibited TRA-induced histamine release from rat mast cells. These results suggest that histamine release from mast cells might be associated with K+ channel activity.
Assuntos
Adenosina Trifosfatases/antagonistas & inibidores , Liberação de Histamina/efeitos dos fármacos , Mastócitos/metabolismo , Canais de Potássio/efeitos dos fármacos , Canais de Sódio/efeitos dos fármacos , Actomiosina/metabolismo , Animais , Hidroxibenzoatos/farmacologia , Técnicas In Vitro , Cinética , Masculino , Mastócitos/efeitos dos fármacos , Músculos/enzimologia , Músculos/metabolismo , Miosinas/metabolismo , Ratos , Ratos Wistar , ATPase Trocadora de Sódio-Potássio/antagonistas & inibidoresRESUMO
Two novel triterpenoids with an unusual 14-carboxyl group, penasterone [1] and acetylpenasterol [2], were isolated from the Okinawan marine sponge Penares incrustans. The structures of 1 and 2 were established mainly on the basis of nmr spectroscopic data. The relative stereochemistry of 1 was confirmed by single-crystal X-ray diffraction analysis. Compounds 1 and 2 potently inhibited histamine release from rat peritoneal mast cells induced by anti-IgE in a dose-dependent manner.
Assuntos
Liberação de Histamina/efeitos dos fármacos , Poríferos/química , Triterpenos/farmacologia , Animais , Cromolina Sódica/farmacologia , Imunoglobulina E/imunologia , Técnicas In Vitro , Mastócitos/efeitos dos fármacos , Mastócitos/metabolismo , RatosRESUMO
In rat peritoneal mast cells induced by anti-immunoglobulin E, ciwujianosides D1 (1) and C1 (2) from Acanthopanax senticosus (ciwujia) strongly inhibited histamine release in a concentration-dependent manner. The inhibitory effect of 1 was approximately 6800 times stronger than that of disodium cromoglycate.
Assuntos
Anticorpos Anti-Idiotípicos/imunologia , Liberação de Histamina/efeitos dos fármacos , Imunoglobulina E/imunologia , Mastócitos/metabolismo , Ácido Oleanólico/análogos & derivados , Plantas Medicinais/química , Saponinas/farmacologia , Animais , Células Cultivadas , Masculino , Mastócitos/efeitos dos fármacos , Cavidade Peritoneal/citologia , Extratos Vegetais/farmacologia , Ratos , Ratos WistarRESUMO
An amide (dehydropipernonaline) that has coronary vasorelaxant activity was isolated from the fruit of Piper longum L. This substance was characterized on the basis of spectroscopic data.
Assuntos
Vasos Coronários/efeitos dos fármacos , Piperidinas/isolamento & purificação , Plantas Medicinais/análise , Vasodilatadores/isolamento & purificação , Animais , Bioensaio , Fenômenos Químicos , Química , Técnicas In Vitro , Espectroscopia de Ressonância Magnética , Piperidinas/análise , Piperidinas/farmacologia , Coelhos , Espectrofotometria Ultravioleta , Vasodilatadores/análiseRESUMO
The crude acetone extract of the fruits of Evodia rutaecarpa Bentham (Rutaceae) exhibited a positive inotropic effect on the guinea pig isolated left atria. The extract was subject to bioassay-directed fractionation to yield the powerful cardiotonic agent evodiamine.