RESUMO
Most liverworts elaborate characteristic odiferous, pungent and bitter tasting compounds many of which show antimicrobial, antifungal, antiviral, allergenic contact dermatitis, cytotoxic, insecticidal, anti-HIV, superoxide anion radical release, plant growth regulatory, neurotrophic, NO production inhibitory, muscle relaxant, antiobesity, piscicidal and nematocidal activities. Several inedible mushrooms produce female spider pheromones, strong antioxidant, and cytotoxic compounds. The present paper is concerned with the extraction and isolation of terpenoids from some bryophytes and inedible fungi and their pungent and bitter taste, and cytotoxic and antiviral activity.
Assuntos
Antineoplásicos/química , Antivirais/química , Briófitas/química , Fungos/química , Terpenos/química , Estrutura MolecularRESUMO
Cytotoxic bibenzyls, and germacrane- and pinguisane-type sesquiterpenoids have been isolated from unidentified Indonesian and Tahitian Frullania sp. and Japanese Porella perrottetiana by using a combination of chromatographic methods. The structure activity relationship (SAR) study showed that the presence of a phthalide group in bibenzyls, an alpha-methylene-gamma-lactone in germacrane-type sesquiterpenoids, and beta-hydroxycarbonyl in pinguisane-type sesquiterpenoids play an important role in providing cytotoxic activity against both human promyelocytic leukemia (HL-60) and human pharyngeal squamous carcinoma (KB) cell lines. The structure of each isolated compound was elucidated by using spectroscopic methods and the cytotoxicity was determined by using the WST-8 colorimetric assay.
Assuntos
Antineoplásicos Fitogênicos/química , Compostos de Benzil/química , Hepatófitas/química , Sesquiterpenos de Germacrano/química , Animais , Antineoplásicos Fitogênicos/farmacologia , Compostos de Benzil/farmacologia , Linhagem Celular Tumoral , Células HL-60 , Humanos , Indicadores e Reagentes , Indonésia , Japão , Células KB , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Extratos Vegetais , Polinésia , Sesquiterpenos de Germacrano/farmacologia , Relação Estrutura-AtividadeRESUMO
The Sumatran forest plants Lerchea cf. bracteata and L. parviflora were found to contain alkaloids and their extract showed siginificant activity toward some testing pathogenic microbes. Isolation work on L.cf bracteata yielded known quaternary alkaloid N(b)-methylantirhine (2) while L. parviflora gave 5,6-dihydroflavopereirine (3).
Assuntos
Alcaloides Indólicos/química , Rubiaceae/química , Antibacterianos/farmacologia , Cromatografia em Camada Fina , Cristalografia por Raios X , Alcaloides Indólicos/farmacologia , Indonésia , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Modelos Moleculares , Extratos Vegetais/química , Especificidade da EspécieRESUMO
Two known coloring constituents, methyl 4,4'-dimethoxyvulpinate (1) and 4,4'-dimethoxyvulpinic acid (2) have been isolated from the fruit body of fungus Scleroderma sinnamariense Mont. The methanolic extract, its fractions and compound (2) showed moderate activity to inhibit the growth of some pathogenic testing microbes used.
Assuntos
Basidiomycota/química , Antibacterianos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Basidiomycota/ultraestrutura , Compostos de Bifenilo/química , Cromatografia em Camada Fina , Cor , Carpóforos/química , Indonésia , Espectroscopia de Ressonância Magnética , Metanol , Testes de Sensibilidade Microbiana , Picratos/química , Solventes , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
Crude extracts of the Tahitian liverworts Mastigophora diclados and Frullania sp., the Indonesian Frullania sp., Dumortiera hirsuta and Marchantia sp., and the Japanese Porella perrottetiana were investigated chemically by using gas chromatography-mass spectrometry (GC-MS). All extracts contained various volatile sesqui- and diterpenoids and a few aromatic compounds. The Tahitian M. diclados and Frullania sp., and the Indonesian Frullania sp. exhibited cytotoxic activity against HL-60 and KB cell lines. The extracts of the Tahitian M. diclados and the Indonesian Marchantia sp. showed radical scavenging activity, whereas the crude extracts of the Tahitian M. diclados and Frullania sp., and the Indonesian Frullania and Marchantia sp. showed antimicrobial activity against Staphylococcus aureus and Bacillus subtilis.
Assuntos
Anti-Infecciosos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Sequestradores de Radicais Livres/farmacologia , Hepatófitas/química , Extratos Vegetais/farmacologia , Diterpenos/análise , Cromatografia Gasosa-Espectrometria de Massas , Células HL-60 , Humanos , Sesquiterpenos/análiseRESUMO
Cembrane-type diterpenoids, 13,18,20-epi-iso-chandonanthone (1) and (8E)-4alpha-acetoxy-12alpha,13alpha-epoxycembra-1(15),8-diene (2), two fusicoccane-type diterpenoids, fusicoauritone 6alpha-methyl ether (3) and 6beta,10beta-epoxy-5beta-hydroxyfusicocc-2-ene (4) and a zierane sesquiterpene gamma-lactone, chandolide (5) were isolated from the Tahitian liverwort Chandonanthus hirtellus (Web.) Mitt., together with eight known diterpenoids, chandonanthine (6), fusicogigantone A (7), fusicogigantone B (8), fusicogigantepoxide (9), anadensin (10), fusicoauritone (11), ent-verticillol (12) and ent-epi-verticillol (13). Their structures were established by a combination of extensive NMR spectroscopy and/or X-ray crystallographic analyses. Compounds 1, 5 and 10 showed weak cytotoxic activity against HL-60. Compound 3 also indicated weak cytotoxic activity against KB cell lines.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Diterpenos/isolamento & purificação , Hepatófitas/química , Lactonas/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Cristalografia por Raios X , Diterpenos/química , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Células HL-60 , Humanos , Células KB , Lactonas/química , Lactonas/farmacologia , Conformação Molecular , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , EstereoisomerismoRESUMO
A drimane, (+)-drimenol (1), five known herbertanes, (-)-alpha-herbertenol (2), (-)-herbertenediol (3), mastigophorene A (4), (-)-mastigophorene C (5) and (-)-mastigophorene D (6), a pimarane, (-)-ent-pimara-8(14),15-dien-19-oic acid (7), and two eudesmanolides, (-)-diplophyllolide A (8) and (-)-diplophyllin (9) were isolated from the Tahitian Mastigophora diclados (Brid.) Nees. Herbertane sesquiterpenes (2, 3, 5 and 6) showed cytotoxicity against HL-60 and KB cell lines, radical scavenging activity and antimicrobial activity against Bacillus subtilis. (-)-Diplophyllolide A (8) also exhibited cytotoxicity against HL-60 and KB cell lines.
Assuntos
Anti-Infecciosos/isolamento & purificação , Citotoxinas/isolamento & purificação , Sequestradores de Radicais Livres/isolamento & purificação , Hepatófitas , Sesquiterpenos/isolamento & purificação , Anti-Infecciosos/química , Anti-Infecciosos/toxicidade , Citotoxinas/química , Citotoxinas/toxicidade , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/toxicidade , Células HL-60 , Hepatófitas/química , Hepatófitas/toxicidade , Humanos , Células KB , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Polinésia , Sesquiterpenos/química , Sesquiterpenos/toxicidadeRESUMO
Six Tahitian liverworts, Trichocolea pluma, Chandonanthus hirtellus, Mastigophora diclados, Jungermannia sp., Plagiochila sp. and Cyathodium foetidissimum were chemically investigated. All of these liverworts produce their own characteristic compounds. Vanillic acid methyl ester was isolated for the first time from T. pluma. Skatol is responsible for the very intense unpleasant odor of C. foetidissimum. Herbertane-type sesquiterpenoids are peculiar components of M. diclados, and fusicoccane-type diterpenoids were identified in Pagiochila sp. Cembranes and ent-verticillanes were isolated from C. hirtellus and also detected in Jungermannia species. C. hirtellus also biosynthesizes algal components and such results may suggest that some liverworts originate from algae.
Assuntos
Hepatófitas/química , Compostos Orgânicos Voláteis/química , Animais , Estrutura Molecular , PolinésiaRESUMO
Investigation on the leaves of Melicope bonwickii (F.Muell.) T.Hartley (Rutaceae) afforded a new 7-(2'-hydroxy-3'-chloroprenyloxy)-4-methoxyfuroquinoline (1) together with the known 7-(2',3'-epoxyprenyloxy)-4-methoxyfuroquinoline (2), evellerine (3) kokusaginine (4) and an amide aurantiamide acetate (5). Compounds 1 and 2 showed significant activity against cervical cell lines (Hela).