RESUMO
Two new steroid derivatives, (22E,24R)-3alpha-ureido-ergosta-4,6,8(14),22-tetraene (1) and (22E,24R)-5alpha,8alpha-epidioxyergosta-6,9,22-triene-3beta-ol 3-O-beta-D-glucopyranoside (2) were isolated from the fruit bodies of Chlorophyllum molybdites (Agaricaceae). The structures were established by spectroscopic and chemical methods. These compounds exhibited cytotoxicity against Kato III cells.
Assuntos
Agaricales/química , Agaricales/crescimento & desenvolvimento , Esteroides/química , Agaricales/citologia , Humanos , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Esteroides/isolamento & purificação , Esteroides/toxicidade , Células Tumorais Cultivadas/citologia , Células Tumorais Cultivadas/efeitos dos fármacosRESUMO
Four cycloartane triterpenes, cyclopassifloic acids A (1), B (2), C (3), and D (4), and six related saponins, cyclopassiflosides I (5), II (6), III (7), IV (8), V (9), and VI (10), were isolated from the leaves and stems of Passiflora edulis, and their structures were elucidated on the base of extensive NMR experiments and chemical methods. Cyclopassifloic acids A-D were assigned as 22(R), 24(S)-1alpha,3beta,22,24,31-pentahydroxy-24-methylcycloartan -28-oic acid; 24(S)-1alpha,3beta,24, 31-tetrahydroxy-24-methylcycloartan-28-oic acid; 20(S),24(S)-1alpha, 3beta,21,24,31-pentahydroxy-24-methylcycloartan-28-oic acid; and 22(R)-1alpha,3beta,22-trihydroxy-24-oxocycloartan-28-oic acid, respectively. Cyclopassiflosides I-VI, in turn, were established as the 28-O-beta-D-glucopyranosides of cyclopassifloic acids A-D. Finally, cyclopassiflosides III and V were demonstrated as the 28, 31-bis-O-beta-D-glucopyranosides of cyclopassifloic acids B and C, respectively. Also obtained in this investigation were the known compounds passiflorin (11) and passifloric acid (12).
Assuntos
Plantas Medicinais/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Estrutura Molecular , Rosales/química , Saponinas/química , Análise Espectral , Triterpenos/químicaRESUMO
The stem of Stephanotis floribunda afforded a new cyclic pentapeptide stephanotic acid (1), possessing a novel 6-(leucin-3'-yl) tryptophan skeleton. The structure of 1 was assigned on the basis of extensive NMR experiments and a chemical reaction and shown to be closely related to the bicyclic octapeptide moroidin (3), a toxin from Laportea moroides.
Assuntos
Peptídeos Cíclicos/química , Plantas Medicinais/química , Madagáscar , Espectroscopia de Ressonância Magnética , Malásia , Caules de Planta/química , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
The structural elucidation of eleven new related polyoxypregnane glycosides, gymnepregosides G (1), H (2), I (3), J (4), K (5), L (6), M (7), N (8), O (9), P (10) and Q (11), from the roots of Gymnema alternifolium (Asclepiadaceae) was achieved by a detailed study of 1H- and 13C-NMR spectral data and chemical means. The results obtained for new compounds, 1-11, show that they are (20S)-pregn-6-ene-3 beta,5 alpha,8 beta,12 beta,14 beta,17 beta,20-heptaol 3-O-glycosides, and all the sugars at C-3 are beta(i-->4)-linked. Some of them possess benzoyl, (E)- and (Z)-cin-namoyl, and tigloyl residues as the ester linkages located at C-12 and/or C-20 of the aglycone.
Assuntos
Glicosídeos/química , Plantas Medicinais/química , Pregnanos/química , Sequência de Carboidratos , Glicosídeos/isolamento & purificação , Hidrólise , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Raízes de Plantas/química , Pregnanos/isolamento & purificação , Espectrometria de Massas de Bombardeamento Rápido de ÁtomosRESUMO
The structural elucidation of six new related polyoxypregnane glycosides, gymnepregosides A (1), B (2), C (3), D (4), E (5) and F (6), together with two known compounds, from the roots of Gymnema alternifolium (Asclepiadaceae) was achieved through on a detailed study of 1H- and 13C-NMR spectral data and chemical means. The results obtained for new compounds, 1-6, show that they are (20S)-pregn-6-ene-3 beta,5 alpha,8 beta,12 beta,14 beta,17 beta,20-heptaol or sarcostin 3-O-glycosides, and all the sugars at C-3 are beta(1-->4)-linked. Some of them possessed benzoyl, cinnamoyl and tigloyl residues as the ester linkages located at C-12 and/or C-20 of the aglycon.
Assuntos
Glicosídeos/química , Glicosídeos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Pregnanos/química , Pregnanos/isolamento & purificação , Sequência de Carboidratos , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Raízes de Plantas/química , Espectrometria de Massas de Bombardeamento Rápido de ÁtomosRESUMO
Two 2-hydroxy-2-benzylcoumaranone glycosides, 2,4, 6-trihydroxy-2-[(4'-hydroxyphenyl) methyl]-3(2H)-benzofuranone-4-yl-beta-D-glucopyranoside (maesopsin 4-O-glucoside) (1) and 2,4,6-trihydroxy-2-[(4'-hydroxyphenyl) methyl]-3(2H)-benzofuranone-4-yl-beta-D-glucopyranosido-4'-y l-alpha-L -rhamnopyranoside (maesopsin 4-O-glucosido 4'-O-rhamnoside) (2), two neolignan glycosides, 2R-(E)-2, 3-dihydro-2-(4'-hydroxy-3'-methoxylphenyl)-5-(3"-hydroxy-1"-pro pen yl) -7-methoxy-3-benzofuranmethanol-4'-yl-beta-D-glucopyranosyl-(1-->3 )-[ beta-D-glucopyranosyl-(l-->2)]-beta-d-glucopyranoside (3) and (threo) 1-(4'-hydroxy-3'-methoxy)-2-(4"-hydroxymethyl-2", 6"-dimethoxyphenoxy)-propane-1,3-diol-4'-yl-beta-d-glucopynosid e (4), and a phenylpropanoid glycoside, 3-methoxy-5-(2'-propenyl)-1, 2-benzenediol-1-yl-beta-D-apiofuranosyl-(1-->6)-beta-D- glucopyransodie (5) were isolated from the bark of Hovenia trichocarea. Compounds 1-5 were named hovetricosides C-G, respectively, and their structures were established by extensive NMR experiments and chemical methods. Also obtained in this investigation were the known compounds acanthoside B, kelampayoside A, shashenoside I, and 3,4, 5-trimethoxyphenol-1-O-beta-D-xylopyranosyl-(1-->6)-beta-D- glucopyranoside.
Assuntos
Glicosídeos/química , Epiderme Vegetal/química , Plantas Medicinais/química , Sequência de Carboidratos , Cromatografia Líquida de Alta Pressão , Glicosídeos/isolamento & purificação , Hidrólise , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
Four new oleanane-type triterpene glycosides, proceraosides A-D (1-4), were isolated from the seeds of Albizia procera. Their structures were established by extensive NMR experiments and chemical methods. Compounds 1-3 comprised acacic acid as the aglycon and a monoterpenic carboxylic acid linked to a monoterpene quinovoside as the acyl moiety at C-21. The common oligosaccharide moiety linked to C-28 in 1-3 was determined as alpha-l-arabino- furanosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-rhamnopyranosy l- (1-->2)-beta-D-glucopyranosyl ester. These compounds differed in the C-3-linked sugar unit or in the configuration of C-6' of the inner monoterpene moiety in the C-21-linked acyl unit. Compound 4 was established as the 16-deoxy analogue of 1.
Assuntos
Plantas Medicinais/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Dados de Sequência Molecular , Saponinas/farmacologia , Sementes/química , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta , Triterpenos/farmacologiaRESUMO
From the fresh stem of Stephanotis lutchuensis var. japonica, ten new oleanane-type triterpenoid glycosides, named sitakisosides XI-XX (1-10), were isolated. Their structures were determined on the basis of spectroscopic data and chemical evidence. The results show that all have a 3-O-beta-D-xylopyranosyl(1 --> 6)-beta-D-glucopyranosyl(1 --> 6)- beta-D-glucopyranosyl moiety and the aglycones of sitakisosides XI-XV, XVI and XVII, XVIII and XIX, and XX are sitakisogenin, chichipegenin, marsglobiferin and longispinogenin, respectively. Sitakisosides XI-XIII, XVI and XVIII, having an acyl group, showed antisweet activity.
Assuntos
Aromatizantes/química , Plantas/química , Saponinas/química , Sequência de Carboidratos , Aromatizantes/administração & dosagem , Humanos , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Extratos Vegetais/química , Caules de Planta/química , Saponinas/isolamento & purificação , Sacarose/administração & dosagem , Sacarose/antagonistas & inibidores , Paladar/efeitos dos fármacosRESUMO
Four new oleanane-type triterpene glycosides, pithedulosides H-K (1-4), were isolated from the seeds of Pithecellobium dulce. Their structures were established by extensive NMR experiments and chemical methods. Compounds 1-3 comprised acacic acid as the aglycon and either monoterpene carboxylic acid and its xyloside or monoterpene carboxylic acid as the acyl moiety at C-21. The oligosaccharide moieties linked to C-3 and C-28 were determined as alpha-L-arabinopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1 -->6)- [beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl and alpha-L-arabinofuranosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->3)]-alpha- rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester, respectively. Compound 4 was established as an echinocystic acid 3-O-glycoside having the same sugar sequences as 1-3. Also obtained in this investigation was the known compound 5, which was identified as echinocystic acid 3-O-beta-D-xylopyranosyl- (1-->2)-alpha-L-arabinopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1 -->2)]- beta-D-glucopyranoside.
Assuntos
Plantas Medicinais/química , Saponinas/química , Triterpenos/química , Sequência de Carboidratos , Hidrólise , Índia , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Saponinas/isolamento & purificação , Sementes/química , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Triterpenos/isolamento & purificaçãoRESUMO
The structural elucidation of seven related oxypregnane-oligoglycosides stephanosides K (1), L (2), M (3), N (4), O (5), P (6), and Q (7) from the fresh stem of Stephanotis lutchuensis var. japonica (Asclepiadaceae) was achieved through on a detailed study of their high-field 1H- and 13C-NMR spectra. The results show that all the sugars are beta (1-->4)-linked. The aglycones of stephanosides K, M, and O, and stephanosides L, N, and P were identified as 12-O-cinnamoyl-20-O-(E)-2-methyl-2-butenoyl, and 12-O-cinnamoyl-20-O-nicotinoyl derivatives of (20S)-pregn-6-ene-3 beta,5 alpha,8 beta,12 beta,14 beta,17 beta,20-heptaol, respectively. The aglycone of stephanoside Q was 12-O-cinnamoyldeacetylmetaplexigenin (kidjoranin).
Assuntos
Glicosídeos/química , Extratos Vegetais/química , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Dados de Sequência MolecularRESUMO
Three main saponins named albiziasaponins A, B, and C were isolated from the barks of Albizia lebbeck. Their structures were established through spectral analyses as acacic acid lactone 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- beta-D-glucopyranoside, 3-O-beta-D-glucopyranosyl-(1-->2)-O-[alpha-L-arabinopyranosyl-(1-- >6)]- beta-D-glucopyranoside and 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- O- [beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranoside.
Assuntos
Plantas Medicinais/química , Saponinas/isolamento & purificação , Configuração de Carboidratos , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Saponinas/química , Espectrometria de Massas de Bombardeamento Rápido de ÁtomosRESUMO
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 fresh stem of Stephanotis lutchuensis var. japonica, we have isolated five new oleane glycosides named sitakisosides I-V (1-5). Their structures were determined on the basis of spectroscopic data and chemical evidence. Sitakisoside V showed the strongest antisweet activity among sitakisosides I-V.
Assuntos
Extratos Vegetais/química , Saponinas/química , Sacarose/antagonistas & inibidores , Sequência de Carboidratos , Humanos , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Caules de Planta/química , Saponinas/isolamento & purificação , Saponinas/farmacologiaRESUMO
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 fresh leaves of Hovenia dulsis var. tomentella, two new aroma glycosides named kenposide A and B have been isolated together with the known glycoside, icariside C1. Their structures were determined on the basis of chemical and spectral evidence.
Assuntos
Álcoois Graxos/isolamento & purificação , Glucosídeos/isolamento & purificação , Glicosídeos/isolamento & purificação , Plantas Medicinais/química , Terpenos/isolamento & purificação , Sequência de Carboidratos , Álcoois Graxos/química , Glucosídeos/química , Glicosídeos/química , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Terpenos/químicaRESUMO
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
The structure of bryonoside, which has previously been isolated from the roots of Bryonia dioica, has been revised. In addition, three new cucurbitacin saponins, named brydioside A, B and C have also been obtained. Their structures were established on the basis of spectral and chemical evidence.
Assuntos
Plantas Medicinais/química , Saponinas/química , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Estrutura Molecular , Saponinas/isolamento & purificaçãoRESUMO
Two steroidal alkaloids were isolated from the bulb of Fritillaria pallidiflora Schreb by column chromatographic techniques. One of them was identified as known alkaloid sinpeinine A, another alkaloid was found to be a new compound named yibeinoside A, which is the Sinpeinine-3-O-beta-glucoside. Its structure was confirmed on the basis of chemical and spectral data (IR, MS, 1HNMR, 13CNMR).