RESUMO
An examination of the endophytic fungus Trichoderma asperellum A-YMD-9-2 obtained from the marine red alga Gracilaria verrucosa led to the isolation of seven new chromanoid norbisabolane derivatives, trichobisabolins I-L (1-4) and trichaspsides C-E (5-7). Their structures and relative configurations were established on the basis of spectroscopic techniques, mainly including 1D/2D NMR and MS, and the absolute configuration of 1 was assigned by X-ray crystallographic analysis using Cu Kα radiation. All of these isolates feature a 1,9-epoxy ring system, and 5-7 represent the second occurrence of norbisabolane aminoglycosides. Compounds 1-7 exhibited potent inhibition of several marine phytoplankton species.
Assuntos
Aminoglicosídeos/farmacologia , Cromanos/farmacologia , Gracilaria/microbiologia , Trichoderma/química , Aminoglicosídeos/química , Aminoglicosídeos/isolamento & purificação , Cromanos/isolamento & purificação , Cristalografia por Raios X , Endófitos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Trichoderma/fisiologiaRESUMO
Eight new bisabolane derivatives, trichobisabolins A-H, along with two known ones, (3R,6R,7R)-1,10-bisaboladien-3-ol (9) and (3R,6R,7S)-1,10-bisaboladien-3,6-diol (10) were isolated from the culture of Trichoderma asperellum Y6-2, obtained from the surface of the marine red alga Chondrus ocellatus. Their structures and relative configurations were identified by interpretation of 1D/2D NMR and MS data. Compounds 1-8 were assayed for inhibiting the growth of some marine-derived organisms, including four marine phytoplankton species, one marine zooplankton species, and five pathogenic bacteria. All of them exhibited inhibition against the marine phytoplanktons with IC50 values ranging from 2.1-78⯵g/mL, compounds 4 and 8 showed weak lethality to the marine zooplankton, and none of them had inhibition against the five pathogenic bacteria.
Assuntos
Bactérias/efeitos dos fármacos , Chondrus/microbiologia , Cicloexanos/farmacologia , Fitoplâncton/efeitos dos fármacos , Trichoderma/química , China , Cicloexanos/isolamento & purificação , Estrutura Molecular , Relação Estrutura-AtividadeRESUMO
A new sesquiterpene, albican-1,14-diol (1), and seven known compounds, including sterigmatocystin (2), 3-hydroxy-5-(hydroxymethyl)-4-(4'-hydroxyphenoxy) pyrrolidin-2-one (3), (1H-indol-3-yl) oxoacetamide (4), indole-3-carboxylic acid (5), indole-3-acetic acid (6), indole-3-carboxaldehyde (7), and volemolide (8), were isolated from the cultures of Aspergillus versicolor, an endophytic fungus isolated from the marine green alga Codium fragile. The structure of 1 was elucidated by 1D, 2D NMR and mass spectroscopic techniques. The bioassay results showed that 1 possessed potent activity against brine shrimp, Escherichia coli, and Staphyloccocus aureus.
Assuntos
Aspergillus/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Animais , Artemia/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Staphylococcus aureus/efeitos dos fármacosRESUMO
Four new chamigrane derivatives, laurecomin A (1), laurecomin B (2), laurecomin C (3), and laurecomin D (4), one new naturally occurring sesquiterpene, 2,10-dibromo-3-chloro-7-chamigren-9-ol acetate (5), and three known halogenated structures, deoxyprepacifenol (6), 1-bromoselin-4(14),11-diene (7), and 9-bromoselin-4(14),11-diene (8), were isolated from the marine red alga Laurencia composita collected from Pingtan Island, China. The structures of these compounds were unambiguously established by 1D, 2D NMR and mass spectroscopic techniques. The bioassay results showed that 2 was active against both brine shrimp and fungus Colletotrichum lagenarium.
Assuntos
Laurencia/química , Extratos Vegetais/farmacologia , Sesquiterpenos/isolamento & purificação , Animais , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Artemia/efeitos dos fármacos , China , Colletotrichum/efeitos dos fármacos , Extratos Vegetais/química , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
Three new halogenated chamigrane sesquiterpenes, laurokamin A (1), laurokamin B (2), and laurokamin C (3), and four known halogenated chamigrane sesquiterpenes, 10-bromo-α-chamigrene (4), 10-bromo-ß-chamigrene (5), 2,10-dibromo-3-chloro-ß-chamigrene (6), and obtusane (7), were isolated from the marine red alga Laurencia okamurae collected from the coast of Rongcheng, China. The structures of these compounds were unambiguously identified by one- and two-dimensional NMR and mass spectroscopic methods. The antimicrobial activity of compounds 1-3 was evaluated.
Assuntos
Laurencia/química , Extratos Vegetais/química , Sesquiterpenos/química , Organismos Aquáticos , Colletotrichum/efeitos dos fármacos , Colletotrichum/crescimento & desenvolvimento , Escherichia coli/efeitos dos fármacos , Escherichia coli/crescimento & desenvolvimento , Fusarium/efeitos dos fármacos , Fusarium/crescimento & desenvolvimento , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Staphylococcus aureus/crescimento & desenvolvimentoRESUMO
Three new halogenated sesquiterpenes, 10-bromo-7α,8α-expoxychamigr-1-en-3-ol (1), 10-bromo-ß-chamigren-8-ol (2), and 10-bromo-3-chlorocupar-5-en-2-ol (3), one new C12-acetogenin, desepilaurallene (7), one new naturally occurring sesquiterpene, 7-hydroxylaurene acetate (4), two known sesquiterpenes, allolaurinterol acetate (5) and laurene (6), and one known C15-acetogenin, epilaurallene (8), were isolated from the marine red alga Laurencia okamurai collected from the coast of Rongcheng, China. The structures of these compounds were unambiguously established by 1D, 2D NMR and mass spectroscopic techniques. The bioassay results showed that 4, 5 exhibited potent antibacterial activity, and 1, 4, 5 were toxic to brine shrimp.
Assuntos
Acetogeninas/isolamento & purificação , Antibacterianos/isolamento & purificação , Produtos Biológicos/química , Laurencia/química , Sesquiterpenos/isolamento & purificação , Acetogeninas/química , Acetogeninas/farmacologia , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Artemia/efeitos dos fármacos , Produtos Biológicos/farmacologia , China , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
Two new epoxy steroids, 5α,8α-epidioxy-22ß,23ß-epoxyergosta-6-en-3ß-ol (1) and 5α,8α-epidioxy-22α,23α-epoxyergosta-6-en-3ß-ol (2), and ten known steroids including (24R)-5α,8α-epidioxyergosta-6-en-3ß-ol (3), (22E,24R)-5α,8α-epidioxyergosta-6,22-dien-3ß-ol (4), (22E,24R)-5α,8α-epidioxyergosta-6,9(11),22-trien-3ß-ol (5), ß-sitosterol (6), sitost-5-en-3ß-ol acetate (7), 7α-hydroxysitosterol (8), schleicheol 2 (9), (24R)-24-ethyl-5α-cholestane-3ß,5α,6ß-triol (10), 7α-hydroxystigmasterol (11), and stigmasterol (12) were isolated from Helianthus tuberosus grown in Laizhou salinized land of coastal zone of Bohai Sea, China. The structures of these compounds were unambiguously established by 1D, 2D NMR and mass spectroscopic techniques. The new compounds 1 and 2 exhibited weak antibacterial activity and no antifungal activity.
Assuntos
Anti-Infecciosos/química , Ergosterol/análogos & derivados , Helianthus/química , Extratos Vegetais/química , Esteroides/isolamento & purificação , Animais , Artemia/efeitos dos fármacos , Artemia/microbiologia , China , Colletotrichum/efeitos dos fármacos , Ergosterol/química , Ergosterol/isolamento & purificação , Ergosterol/farmacologia , Escherichia coli/efeitos dos fármacos , Fusarium/efeitos dos fármacos , Espectroscopia de Ressonância Magnética/métodos , Espectrometria de Massas/métodos , Estrutura Molecular , Sitosteroides/química , Staphylococcus aureus/efeitos dos fármacos , Esteroides/química , Esteroides/farmacologia , Estigmasterol/químicaRESUMO
A new pyrrolidine derivative, 3-hydroxy-5-(hydroxymethyl)-4-(4'-hydroxyphenoxy)pyrrolidin-2-one (1), and eight known steroids, (22E,24R)-7beta,8beta-epoxy-3beta,5alpha,9alpha-trihydroxyergosta-22-en-6-one (2, a reassigned structure of (22E,24R)-5alpha,6alpha-epoxy-3beta,8beta,14alpha-trihydroxyergosta-22-en-7-one), (22E,24R)-3beta,5alpha,9alpha-trihydroxyergosta-7,22-dien-6-one (3), (22E,24R)-3beta,5alpha-dihydroxyergosta-7,22-dien-6-one (4), (22E,24R)-ergosta-7,22-dien-3beta/,5alpha,6beta-triol (5), (22E,24R)-ergosta-5,22-dien-3beta-ol (6), (22E,24R)-5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol (7), (22E,24R)-5alpha,8alpha-epidioxyergosta-6,9(11),22-trien-3beta-ol (8), and (22E,24R)-1(10 --> 6)-abeo-ergosta-5,7,9,22-tetraen-3alpha-ol (9), were isolated from the cultures of Gibberella zeae, an endophytic fungus isolated from the marine green alga Codium fragile. Their structures and relative stereochemistry were elucidated by 1D, 2D NMR and mass spectroscopic techniques. Compound 1 showed cytotoxicity against A-549 and BEL-7402 cell lines.