RESUMO
Six new secoiridoid constituents, named isoligustrosidic acid (1), 6'-O-trans-cinnamoyl 8-epikingisidic acid (2), 6'-O-cis-cinnamoyl 8-epikingisidic acid (3), oleopolynuzhenide A (4), nuzhenals A (5) and B (6) were isolated from the dried fruits of Ligustrum lucidum AIT. Their structures were established on the basis of spectral and chemical data.
Assuntos
Frutas/química , Iridoides/química , Ligustrum/química , Dessecação , Iridoides/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Hydrolysis of isoligustroside (1) and isooleuropein (2), secoiridoid glucosides, in the presence of ß-glucosidase provided 2-(4-hydroxyphenyl)methyl (2R,3S,4S)-3-formyl-3,4-dihydro-4-(2-methoxy-2-oxoethyl)-2-methyl-2H-pyran-5-carboxylate (3) and 2-(3,4-dihydroxyphenyl)methyl (2R,3S,4S)-3-formyl-3,4-dihydro-4-(2-methoxy-2-oxoethyl)-2-methyl-2H-pyran-5-carboxylate (4), respectively. The structures of 3 and 4 were elucidated on the basis of extensive spectral analyses, including 2D-NMR experiments. Compounds 3 and 4 were found to be new rearrangement products of the aglycones of 1 and 2. The cytotoxic activities of 3 and 4 were evaluated using a disease-oriented panel of 39 human cancer cell lines and showed moderate cytotoxic activity for 4, while 3 exhibited weaker activity compared to that of 4.
Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Glucosídeos Iridoides/química , Glucosídeos Iridoides/farmacologia , Neoplasias/tratamento farmacológico , Syringa/química , Antineoplásicos Fitogênicos/metabolismo , Proliferação de Células/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Hidrólise , Glucosídeos Iridoides/metabolismo , Folhas de Planta/química , beta-Glucosidase/metabolismoRESUMO
Influenza A virus (IAV) infection is perennially one of the leading causes of death worldwide. Effective therapy and vaccination are needed to control viral expansion. However, current anti-IAV drugs risk inducing drug-resistant virus emergence. Although intranasal administration of whole inactivated virus vaccine can induce efficient protective immunity, formalin and ß-propiolactone are the currently used and harmful inactivating agents. Here, we analyzed the antiviral activity of hibiscus (Hibiscus sabdariffa L.) tea extract against human IAV and evaluated its potential as a novel anti-IAV drug and a safe inactivating agent for whole inactivated vaccine. The in vitro study revealed that the pH of hibiscus tea extract is acidic, and its rapid and potent antiviral activity relied largely on the acidic pH. Furthermore, the mouse study showed that the acidic extract was not effective for either therapeutic or vaccination purposes. However, hibiscus tea extract and protocatechuic acid, one of the major components of the extract, showed not only potent acid-dependent antiviral activity but also weak low-pH-independent activity. The low-pH-independent activity did not affect the conformation of immunodominant hemagglutinin protein. Although this low-pH-independent activity is very limited, it may be suitable for the application to medication and vaccination because this activity is not affected by the neutral blood environment and does not lose antigenicity of hemagglutinin. Further study of the low-pH-independent antiviral mechanism and attempts to enhance the antiviral activity may establish a novel anti-IAV therapy and vaccination strategy.
Assuntos
Antivirais/administração & dosagem , Antivirais/química , Hibiscus/química , Vírus da Influenza A/efeitos dos fármacos , Influenza Humana/tratamento farmacológico , Extratos Vegetais/administração & dosagem , Extratos Vegetais/química , Animais , Feminino , Humanos , Concentração de Íons de Hidrogênio , Vírus da Influenza A/crescimento & desenvolvimento , Influenza Humana/virologia , Camundongos , Camundongos Endogâmicos BALB CRESUMO
Careful reexamination of the published ¹H- and ¹³C-NMR spectral data of (22E)-24-methylcholesta-8(14),22-diene-3ß,5α,6ß,7α-tetraol (1), isolated from the marine-derived fungus Penicillium sp., indicates that, in reality, the compound is 5α,6α-epoxy-(22E,24R)-24-methylcholesta-8(14),22-diene-3ß,7α-diol (5).
Assuntos
Colestadienóis/química , Penicillium/química , Colestadienóis/isolamento & purificação , Estrutura MolecularRESUMO
Careful reexamination of the published ¹H and ¹³C NMR spectral data of (22E)-ergosta-7,22-diene-3ß,5α,6ß,9α,14α-pentol (1), isolated from the spores of the medicinal mushroom Ganoderma lucidum, indicates that, in reality, the compound is (22E)-ergosta-7,22-diene-3ß,5α,6ß,9α,14ß-pentol (5).
Assuntos
Ergosterol/análogos & derivados , Reishi/química , Esporos Fúngicos/química , Ergosterol/química , Estrutura MolecularRESUMO
Careful reexamination of the published 1H- and 13C-NMR spectral data of (24S)-24-ethylcholest-8-ene-3ß,5α,6ß,7α-tetraol (1) and (24S)-24-ethylcholest-8(14)-ene-3ß,5α,6ß,7α-tetraol (2), isolated from the marine sponge Neofibularia nolitangere, indicates that, in reality, compounds 1 and 2 are (24S)-5α,6α- epoxy-24-ethylcholest-8-ene-3ß,7α-diol (9) and (24S)-5α,6α-epoxy-24-ethylcholest-(14)-ene-3ß,7α-dio (10), respectively.
Assuntos
Poríferos/química , Esteróis/química , Animais , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Five triterpenoids, (20S)-dammara-13(17),24-dien-3-one, (20R)-dammara-13(17),24-dien-3-one, chirat-16-en-3-one, chirat-17(22)-en-3-one and 17beta,21beta-epoxyhopan-3-one, were isolated from the rhizomes and roots of Gentiana scabra together with five known ones, chiratenol, hop-17(21)-en-3-one, hop-17(21)-en-3beta-ol, lupeol and alpha-amyrin. The structures of new compounds were elucidated on the basis of spectroscopic studies.
Assuntos
Gentianaceae/química , Rizoma/química , Triterpenos/isolamento & purificação , Raízes de Plantas/química , Análise Espectral , Triterpenos/químicaRESUMO
Over the past twenty years, our research group has been studying the chemical constituents of mushrooms. From nineteen species, namely, Amanita virgineoides Bas (Amanitaceae), Daedaleopsis tricolor (Bull.: Fr.) Bond. et Sing. (Polyporaceae), Grifolafrondosa (Fr.) S. F. Gray (Polyporaceae), Hericium erinaceum (Bull.: Fr.) Pers. (Hericiaceae), Hypsizigus marmoreus (Peck) Bigelow (Tricholomataceae), Lactarius piperatus (Scop.: Fr.) S. F. Gray (Russulaceae), Lentinula edodes (Berk.) Sing. (Pleurotaceae), Lyophyllyum connatum (Schum.: Fr.) Sing. (Tricholomataceae), Naematoloma sublateritium (Fr.) Karst. (Strophariaceae), Ompharia lapidescens Schroeter (Polyporaceae), Panellus serotinus (Pers.: Fr.) Kuhn. (Tricholomataceae), Pholiota nameko (T. Ito) S. Ito et Imai in Imai (Strophariaceae), Pleurotus eringii (DC.: Fr.) Quel. (Pleurotaceae), Polyporus umbellatus Fries (Polyporaceae), Russula delica Fr. (Russulaceae), Russula sanguinea (Bull.) Fr. (Russulaceae), Sarcodon aspratus (Berk.) S. Ito (Thelephoraceae), Tricholoma matsutake (S. Ito et Imai) Sing. (Tricholomataceae), and Tricholomaportentosum (Fr.) Quel. (Tricholomataceae), we isolated eight new sesquiterpenoids, six new meroterpenoids, three new triterpenoids, and twenty eight new sterols. In this review, structural features of these new compounds are discussed.
Assuntos
Agaricales/química , Esteróis/química , Terpenos/química , Japão , Estrutura MolecularRESUMO
Over the past twenty years, our research group has been involved in the phytochemical study of terpenoids from Compositae plants. From seven species, namely, Erigeron annuus (L.) PERS., Erigeron philadelphicus L., Erigeron sumatrensis RETZ., Ligularia dentata HARA, Ligularia stenocephala MATSUM. et KOIDZ., Petasites japonicus MAXIM., and Tussilago farfara L., we isolated 83 new compounds. In this review, structural features of 19 eremophilane-type sesquiterpenoids from rhizomes of P. japonicus and 9 bisabolane-type sesquiterpenoids from roots of L. dentata are discussed.
Assuntos
Asteraceae/química , Petasites/química , Rizoma/química , Terpenos/química , Estrutura Molecular , Raízes de Plantas/química , Terpenos/isolamento & purificaçãoRESUMO
This review will summarize the authors' studies on the structures of terpenoids and related compounds from plants of the family Compositae (Asteraceae). Eighty three new compounds have been obtained and characterized from seven species of the plants, namely, Erigeron annuus (L.) Pers., Erigeron philadelphicus L., Erigeron sumatrensis Retz, Ligularia dentata Hara, Ligularia stenocephala Matsum. et Koidz., Petasites japonicus Maxim. and Tussilago farfara L.
Assuntos
Asteraceae/química , Terpenos/química , Flores/química , Estrutura Molecular , Rizoma/química , Terpenos/isolamento & purificaçãoRESUMO
The family Russulaceae is one of the largest in the subdivision Basidiomycotina in Whittaker's Kingdom of Fungi [1] and comprises hundreds of species, worldwide distributed, belonging to the genera Lactarius and Russula. While secondary metabolites occurring in the fruiting bodies of Lactarius species have been well investigated [2], the Russula mushrooms have received less attention, notwithstanding the larger number of existing species [3]. In a previous paper, we reported the isolation and structural elucidation of sterols from the fruiting bodies of Russula sanguinea (Bull.) Fr. [4]. In the course of further studies on the constituents of the above mushroom, three new lactarane sesquiterpenoids, sangusulactones A-C (1-3), along with two known compounds have been isolated (Figure 1). This paper deals with the structural elucidation of the new compounds. The known compounds 4 and 5 were identified as blennin A (4) [5] and 15-hydroxyblennin A (5) [6], respectively, by comparison of their spectral data with those reported in the literature.
Assuntos
Agaricales/química , Sesquiterpenos/química , Espectroscopia de Ressonância Magnética , Sesquiterpenos/isolamento & purificaçãoRESUMO
A new geranylated aromatic compound, 5-[(2'E)-3',7'-dimethyl-2',6'-octadienyl]-4-hydroxy-6-methoxy-1-isoindolinone (1), was isolated from the fruiting bodies of the mushroom Hericium erinaceum (Bull.: Fr.) Pers. (Hericiaceae) together with three known sterols, 5alpha,6alpha-epoxy-(22E)-ergosta-8(14),22-diene-3beta,7alpha-diol (2), (22E)-ergosta-7,9(11),22-triene-3beta,5alpha,6beta-triol (3) and (22E)-ergosta-7,22-diene-3beta,5alpha,6alpha,9alpha-tetrol (4). The structure of the new compound was elucidated on the basis of spectral data.
Assuntos
Basidiomycota/química , Isoindóis/isolamento & purificação , Carpóforos/química , Isoindóis/química , Estrutura MolecularRESUMO
Two new glycosides, named plicatumoside A (1) and (+)-neomedioresinol 4,4'-di-O-ß-D: -glucopyranoside (2), together with 13 known compounds, were isolated from the leaves of Viburnum plicatum Thunb. ex Murray var. plicatum f. plicatum. Their structures were established on the basis of NMR, MS, and chemical data.
Assuntos
Glicosídeos/química , Folhas de Planta/química , Viburnum/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura MolecularRESUMO
Two new glycosides, named dideoxyplicatumoside A (1) and erythro-syringylglycerol-beta-O-4'-(+)-isoeucommin A 4'''-O-beta-D-glucopyranoside (2), together with seven known compounds, were isolated from the leaves of Viburnum plicatum Thunb. ex Murray var. plicatum f. plicatum. Their structures were established on the basis of NMR, MS and chemical data.
Assuntos
Glicosídeos/isolamento & purificação , Fenóis/isolamento & purificação , Glicosídeos/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Fenóis/química , Folhas de Planta/química , Viburnum/químicaRESUMO
Three new glycosides, 7-deoxyloganic acid beta-D-glucopyranosyl ester (1), (3R)-hydrangenol 8,4'-di-O-beta-D-glucopyranoside (2), and (6R,7E,9R)-megastigma-4,7-dien-3-one 9,13-di-O-beta-D-glucopyranoside (3), have been isolated from the leaves of Hydrangea macrophylla subsp. serrata (THUNB.) MAKINO (Saxifragaceae). The structures of 1-3 were elucidated on the basis of spectral data and chemical evidence.
Assuntos
Glicosídeos/química , Hydrangea/química , Configuração de Carboidratos , Sequência de Carboidratos , Dicroísmo Circular , Glioxal , Hidrólise , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Folhas de Planta/química , Espectrofotometria UltravioletaRESUMO
From dried whole plants of Glechoma hederacea L. (Labiatae), seven known glycosides were isolated and identified: (6R,7E,9R)-megastigma-4,7-dien-3-one 9-O-beta-D-glucopyranoside (1), apigenin 7-O-neohesperidoside (2), chrysoeriol 7-O-neohesperidoside (3), (+)-pinoresinol 4,4'-bis-O-beta-D-glucopyranoside (4), (+)-syringaresinol 4,4'-bis-O-beta-D-glucopyranoside (5), (+)-lariciresinol 4,4'-bis-O-beta-D-glucopyranoside (6), and (7R,8R)-threo-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan 4-O-beta-D-glucopyranoside (7).
Assuntos
Glicosídeos/isolamento & purificação , Lamiaceae/química , Extratos Vegetais/química , Glicosídeos/química , Plantas Medicinais/químicaRESUMO
Two new glycosides, 7S,7'S,8R,8'R-icariol A(2)-9-O-beta-D-glucopyranoside (1) and 4-allyl-2-hydroxyphenyl 1-O-beta-D-apiosyl-(1-->6)-beta-D-glucopyranoside (2), were isolated from the dried whole plants of Glechoma hederacea L. (Labiatae) together with four known compounds, cistanoside E (3), dihydrodehydrodiconiferyl alcohol 4-O-beta-D-glucopyranoside (4), apigenin 7-O-beta-D-glucuronopyranoside (5) and luteolin 7-O-beta-D-glucopyranoside (6). The structures of the new compounds were elucidated on the basis of chemical and spectral analysis.
Assuntos
Glicosídeos/química , Lamiaceae/química , Lignina/análogos & derivados , Extratos Vegetais/química , Plantas Medicinais , Dicroísmo Circular , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Lignina/química , Lignina/isolamento & purificação , Lignina/farmacologia , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
Five new phenylethanoid glycosides, lamiusides A (1), B (2), C (3), D (4) and E (5), were isolated from the whole plants of Lamium purpureum L. (Labiatae) together with seven known compounds (6-12). On the basis of chemical and spectral analyses, the structures of the new compounds were elucidated to be 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(4-O-trans-caffeoyl)-beta-D-glucopyranoside (1), 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(4-O-trans-feruloyl)-beta-D-glucopyranoside (2), 2-(3,4-dihydroxyphenyl)ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(6-O-trans-caffeoyl)-beta-D-glucopyranoside (3), 2-(3,4-dihydroxyphenyl)-R,S-methoxy-ethyl-O-beta-D-galactopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)-(4-O-trans-caffeoyl)-beta-D-glucopyranoside (4) and 2-(3-hydroxy-4-methoxyphenyl)ethyl-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-(4-O-cis-feruloyl)-beta-D-glucopyranoside (5). In addition, the radical-scavenging activities of compounds 1-4 on 1,1-diphenyl-2-picrylhydrazyl radical were examined.
Assuntos
Glicosídeos/química , Lamiaceae/química , Configuração de CarboidratosRESUMO
Three new dimeric benzofuran derivatives, ligulacephalins A (1), B (2) and C (3), were isolated from the roots of Ligularia stenocephala MATSUM. ET KOIDZ. (Compositae) together with three known compounds, 5,6-dimethoxy-2-isopropenylbenzofuran (4), euparin (5) and (R)-(-)-hydroxytremetone (6). The structures of the new compounds were determined by spectroscopic evidence. The chiral HPLC analysis demonstrated that 1-3 occurred as a racemate. The absolute configurations of each enantiomer from 1-3 were elucidated on the basis of circular dichroism (CD) data.
Assuntos
Asteraceae/química , Benzofuranos/química , Benzofuranos/isolamento & purificação , Sequência de Carboidratos , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Conformação Molecular , Dados de Sequência Molecular , Raízes de Plantas/química , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria Ultravioleta , EstereoisomerismoRESUMO
Two new aromatic compounds, erinacerins A (1) and B (2), were isolated from the fruiting bodies of Hericium erinaceum (BULL.: FR.) PERS. (Hericiaceae) together with a known compound, hericenone A (3). The structures of the new compounds were elucidated on the basis of their spectral data. It was found that 1 occurred as a racemate.