RESUMEN
The chemical screening of a cultured soft coral, Briareum violaceum, led to the isolation of eight natural, briarane-related diterpenoids, including three unreported metabolites, briavioids E-G (1-3), and five known briaranes, briacavatolides B (4) and C (5), briaexcavatin L (6), briaexcavatolide U (7) and briarenol K (8). The structures of briaranes 1-8 were established using spectroscopic methods. The absolute configuration of briavioid A (9), obtained in a previous study, was reported for the first time in this study by a single-crystal X-ray diffraction analysis using a copper radiation source. The anti-inflammatory activity of briaranes 1 and 2 and briaranes 4-8 was evaluated by screening their inhibitory ability against the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins in lipopolysaccharide (LPS)-induced RAW 264.7 macrophage cells.
Asunto(s)
Antozoos , Diterpenos , Animales , Ratones , Antiinflamatorios/farmacología , Células RAW 264.7 , Macrófagos/metabolismo , Diterpenos/farmacología , Antozoos/química , Óxido Nítrico Sintasa de Tipo II/metabolismo , Ciclooxigenasa 2/metabolismoRESUMEN
Two cembranoids, including a new compound, lobocrassin I (1), as well as a known analogue, lobohedleolide (2), were obtained by solvent extraction from octocoral Lobophytum crassum. This study employed a spectroscopic approach to establish the structures of these two cembranoids, and utilized single-crystal X-ray diffraction analysis to determine their absolute configurations. The results of biological activity assays demonstrated that cembranoid 2 exhibited bioactivity against the protein expressions of inducible nitric oxide synthase (iNOS) lipopolysaccharide (LPS)-treated RAW 264.7 mouse macrophage cells.
Asunto(s)
Antozoos/química , Antiinflamatorios/aislamiento & purificación , Diterpenos/aislamiento & purificación , Animales , Antiinflamatorios/química , Antiinflamatorios/farmacología , Diterpenos/química , Diterpenos/farmacología , Lipopolisacáridos , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Ratones , Óxido Nítrico Sintasa de Tipo II/genética , Células RAW 264.7 , Difracción de Rayos XRESUMEN
In this review, 170 natural substances, including steroid, diterpenoid, sesquiterpenoid, peptide, prostaglandin, base, chlorolipid, bicyclolactone, amide, piperazine, polyketide, glycerol, benzoic acid, glycyrrhetyl amino acid, hexitol, pentanoic acid, aminoethyl ester, octadecanone, alkaloid, and a 53-kD allergenic component from octocorals belonging to genus Dendronephthya, were listed. Some of these compounds displayed potential bioactivities.
Asunto(s)
Antozoos/metabolismo , Productos Biológicos/química , Alérgenos/química , Alérgenos/metabolismo , Aminoácidos/química , Aminoácidos/metabolismo , Animales , Productos Biológicos/metabolismo , Prostaglandinas/química , Prostaglandinas/metabolismo , Esteroides/química , Esteroides/metabolismo , Terpenos/química , Terpenos/metabolismoRESUMEN
Two previously undescribed caryophyllane-related sesquiterpenoids, antipacids A (1) and B (2), with a novel bicyclo[5.2.0] core skeleton, and known compound clovane-2ß,9α-diol (3), along with rumphellolide L (4), an esterified product of 1 and 3, were isolated from the organic extract of octocoral Rumphella antipathes. Their structures, including the absolute configurations were elucidated by spectroscopic and chemical experiments. In vivo anti-inflammatory activity analysis indicated that antipacid B (2) inhibited the generation of superoxide anions and the release of elastase by human neutrophils, with IC50 values of 11.22 and 23.53 µM, respectively, while rumphellolide L (4) suppressed the release of elastase with an IC50 value of 7.63 µM.
Asunto(s)
Antozoos/metabolismo , Antiinflamatorios/farmacología , Neutrófilos/efectos de los fármacos , Sesquiterpenos Policíclicos/farmacología , Animales , Antiinflamatorios/aislamiento & purificación , Humanos , Elastasa de Leucocito/metabolismo , Estructura Molecular , Neutrófilos/metabolismo , Sesquiterpenos Policíclicos/aislamiento & purificación , Relación Estructura-Actividad , Superóxidos/metabolismoRESUMEN
Five 8,17-epoxybriaranes, including three new compounds-briarenols I-K (1-3), along with two known analogues, briaexcavatolide P (4) and briaexcavatin P (5), were isolated from the octocoral Briareum excavatum. The structures of briaranes 1-3 were elucidated by spectroscopic methods, including 1D and 2D NMR studies and (+)-HRESIMS. Briarane 4 exerted inhibition effects on inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7.
Asunto(s)
Antozoos/química , Antiinflamatorios/farmacología , Ciclooxigenasa 2/metabolismo , Diterpenos/farmacología , Óxido Nítrico Sintasa de Tipo II/metabolismo , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Diterpenos/química , Diterpenos/aislamiento & purificación , Regulación hacia Abajo , Regulación Enzimológica de la Expresión Génica/efectos de los fármacos , Ratones , Estructura Molecular , Células RAW 264.7RESUMEN
BACKGROUND: The freshwater species on Taiwan Island have been documented to have originated from mainland China and the Japanese islands from multiple events and by multiple colonization routes. Moreover, the sequences from the mitochondrial DNA cytochrome c oxidase subunit I (COI) have been used for DNA barcoding to identify the species. This study used the COI sequences to identify Neocaridina species in Taiwan and to examine their geographical and temporal origins. RESULTS: In total, 479 specimens were collected from 35 localities, which covered almost all rivers in Taiwan. In addition, some sequences were downloaded from GenBank. The maximum likelihood (ML) tree displayed that all sequences were sorted into 13 taxa (clades), and all sequences in Taiwan were sorted into four clades. The Bayesian skyline plots revealed that these four Neocaridina species have declined recently in Taiwan. CONCLUSIONS: All results support that (1) there are four Neocaridina species in Taiwan, which are N. davidi, N. saccam, N. ketagalan and an undescribed Neocaridina species (N. sp.); (2) these four species colonized Taiwan Island in four colonization events; (3) N. sp. colonized Taiwan first; (4) after the island reached its shape, N. ketagalan and N. saccam colonized Taiwan from the Japanese islands and mainland China, respectively; (5) N. davidi colonized northern Taiwan last; and (6) the cyclic glacial and landform changes in East Asia shaped the colonization events and population structures of the Neocaridina species.
Asunto(s)
Código de Barras del ADN Taxonómico/veterinaria , Decápodos/clasificación , Complejo IV de Transporte de Electrones/genética , Animales , Proteínas de Artrópodos/genética , China , Decápodos/genética , Japón , Funciones de Verosimilitud , Filogenia , Filogeografía , Análisis de Secuencia de ADN/veterinaria , TaiwánRESUMEN
Three new 8-hydroxybriaranes-fragilides R-T (1-3) were obtained from a sea whip gorgonian coral Junceella fragilis. The structures of briaranes 1-3 were elucidated by using spectroscopic methods, including 1D (1H and 13C NMR), 2D (COSY, HSQC, HMBC, and NOESY experiments) NMR studies, and (+)-HRESIMS. Fragilides S and T (2 and 3) are the only briaranes known to possess 8α-hydroxy and 17ß-methyl groups, respectively. Briarane 2 exerted an inhibition effect on iNOS release from RAW264.7; a macrophage cell line that originated from a mouse monocyte macrophage, stimulated with lipopolysaccharides.
Asunto(s)
Antozoos/química , Antiinflamatorios/farmacología , Diterpenos/farmacología , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Diterpenos/química , Diterpenos/aislamiento & purificación , Ratones , Estructura Molecular , Óxido Nítrico Sintasa de Tipo II/antagonistas & inhibidores , Óxido Nítrico Sintasa de Tipo II/metabolismo , Espectroscopía de Protones por Resonancia Magnética , Células RAW 264.7 , Relación Estructura-ActividadRESUMEN
Three new furanocembranoids-briaviodiol F (1) and briaviotriols A (2) and B (3)-along with a known analogue, briaviodiol A (4), were obtained from a cultured-type octocoral Briareum violaceum. The structures of cembranoids 1â»3 were elucidated by using spectroscopic methods. In vitro study demonstrated that compounds 2 and 4 exerted inhibition effects on inducible nitric oxide synthase (iNOS) release from RAW 264.7, a macrophage cell line that originated from a mouse monocyte macrophage, stimulated with lipopolysaccharides.
Asunto(s)
Antozoos/química , Antiinflamatorios/farmacología , Diterpenos/farmacología , Óxido Nítrico Sintasa de Tipo II/antagonistas & inhibidores , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Diterpenos/química , Diterpenos/aislamiento & purificación , Ratones , Modelos Moleculares , Estructura Molecular , Células RAW 264.7RESUMEN
The structures, names, bioactivities, and references of 82 natural products, including 48 new metabolites, purified from the gorgonian corals belonging to the genus Junceella are described in this review. All compounds mentioned in this review were obtained from Junceella fragilis, Junceella gemmacea, Junceella juncea, and Junceella sp., collected from tropical Indo-Pacific Ocean. Some of these compounds exhibited potential biomedical activities.
Asunto(s)
Antozoos/metabolismo , Antibacterianos/química , Antiinflamatorios/química , Antifúngicos/química , Productos Biológicos/química , Animales , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Antifúngicos/aislamiento & purificación , Antifúngicos/farmacología , Productos Biológicos/aislamiento & purificación , Productos Biológicos/metabolismo , Estructura Molecular , Océano PacíficoRESUMEN
Caridina pseudodenticulata is a land-locked freshwater shrimp, which is endemic to North and West Taiwan. It is listed as Vulnerable under criteria A1ce in the IUCN Red List. Our study used mitochondrial DNA fragment sequences of the cytochrome oxidase subunit I (COI) gene to examine its genetic structure. In total, 204 sequences were analyzed from 22 populations, and all 39 haplotypes were identified. Our study (1) found that the genetic diversity within population of this species was similar to that of other land-locked freshwater prawn in Taiwan; (2) displayed that during glaciation, the Taiwan Strait was largely above water, an event which created opportunities for colonization Taiwan and dispersal widely; (3) showed that although the phylogenetic analysis showed the lack of a population genetic structure, the AMOVA and haplotypes distribution pattern revealed geographically divided; (4) indicated that C. pseudodenticulata could across to neighbor rivers through the mouths of rivers, which confluent with each other during floods.
Asunto(s)
Decápodos/genética , Complejo IV de Transporte de Electrones/genética , Animales , ADN Mitocondrial/genética , Agua Dulce , Variación Genética , Genética de Población/métodos , Genoma Mitocondrial/genética , Mitocondrias/genética , Filogenia , Ríos , Análisis de Secuencia de ADN/métodos , Mariscos , TaiwánRESUMEN
Columnaristerol A (1), a rare natural 19-norsterol possessing a 10ß-hydroxy group was isolated from the Formosan octocoral Nephthea columnaris, and its structure was elucidated by spectroscopic methods. Sterol 1 was found to be a cytotoxic agent that exhibited in vitro moderate cytotoxic activity against MOLT-4 and SUP-T1 human leukemia-lymphoma cell lines.
Asunto(s)
Antozoos/metabolismo , Noresteroides/química , Noresteroides/farmacología , Esteroles/química , Esteroles/farmacología , Animales , Espectroscopía de Resonancia Magnética con Carbono-13 , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Espectroscopía de Protones por Resonancia Magnética , Relación Estructura-Actividad , TaiwánRESUMEN
Four new marine sterols, (22E,24R)-ergosta-5,22-diene-3ß,11α-diol (1), (24S)-ergosta-5-ene-3ß,11α-diol (2), 5α,6α-epoxy-23-demethylgorgost-8-ene-3ß,7α-diol (3), and 5α,6α-epoxy-23-demethylgorgost-8(14)-ene-3ß,7α-diol (4), along with a known metabolite, 23-demethylgorgost-7-ene-3ß,5α,6ß-triol (5), were isolated from an algal-bearing gorgonian coral Pinnigorgia sp., collected off the waters of Taiwan. The structures of these sterols were elucidated on the basis of spectroscopic methods. Sterols 1-5 were tested for in vitro cytotoxicity in hepatic stellate cells (HSCs). Proliferation of HSCs plays a key role in the pathogenesis of liver fibrosis.
Asunto(s)
Antozoos/química , Antozoos/microbiología , Esteroles/química , Animales , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
The structures of pubinernoid A (1) and apo-9'-fucoxanthinone (2), isolated from a gorgonian coral Pinnigorgia sp., were elucidated on the basis of spectroscopic analysis and by comparison of their spectroscopic data with those of known compounds. This is the first report of 1 and 2 from an animal source. Apo-9'-fucoxanthinone (2) displayed a significant inhibitory effect on the release of elastase by human neutrophils, with an IC50 value of 5.75 µM.
Asunto(s)
Antozoos/química , Terpenos/química , Animales , Antozoos/metabolismo , Humanos , Estructura Molecular , Neutrófilos/efectos de los fármacos , Neutrófilos/enzimología , Elastasa Pancreática/análisis , Elastasa Pancreática/metabolismo , Metabolismo Secundario , Terpenos/metabolismo , Terpenos/farmacologíaRESUMEN
Persistent organic pollutants (POPs), including polychlorinated dibenzo-p-dioxins and dibenzofurans (PCDD/Fs), polychlorinated biphenyls (PCBs), polybrominated dibenzo-p-dioxins and dibenzofurans (PBDD/Fs), polybrominated biphenyls (PBBs), and polybrominated diphenyl ethers (PBDEs), have been identified in penguins, lichens, soils, and ornithogenic soils in the Antarctic coastal environment in this study. To the best of our knowledge, no previous study has reported PBDD/F and PBB data from Antarctica. The POP mass contents in penguins were in the following order: PCBs >> PBDEs >> PCDD/Fs; PCBs were the dominant pollutants (6310-144,000 pg/g-lipid), with World Health Organization toxic equivalency values being 2-14 times higher than those of PCDD/Fs. Long-range atmospheric transport is the most primary route by which POPs travel to Antarctica; however, local sources, such as research activities and penguin colonies, also influence POP distribution in the local Antarctic environment. In penguins, the biomagnification factor (BMF) of PCBs was 61.3-3760, considerably higher than that for other POPs. According to BMF data in Adélie penguins, hydrophobic PBDE congeners were more biomagnified at log Kow > 6, and levels decreased at log Kow > 7.5 because larger molecular sizes inhibited transfer across cell membranes.
Asunto(s)
Dibenzofuranos Policlorados/análisis , Monitoreo del Ambiente/métodos , Contaminantes Ambientales/análisis , Éteres Difenilos Halogenados/análisis , Bifenilos Policlorados/análisis , Dibenzodioxinas Policloradas/análisis , Spheniscidae/metabolismo , Animales , Regiones Antárticas , Dibenzofuranos Policlorados/farmacocinética , Contaminantes Ambientales/farmacocinética , Éteres Difenilos Halogenados/farmacocinética , Humanos , Bifenilos Policlorados/farmacocinética , Dibenzodioxinas Policloradas/farmacocinética , Suelo/químicaRESUMEN
Three new 9,11-secosterols, pinnisterols A-C (1-3), were isolated from a gorgonian coral Pinnigorgia sp., collected off the waters of Taiwan. The structures of these compounds were elucidated on the basis of spectroscopic methods. The new sterols 1 and 3 displayed significant inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils, and sterol 1 was found to show moderate cytotoxicity in hepatic stellate cells (HSCs).
Asunto(s)
Antozoos/química , Esteroles/química , Animales , Antineoplásicos/química , Antineoplásicos/farmacología , Línea Celular Tumoral/efectos de los fármacos , Humanos , Neutrófilos/efectos de los fármacos , Neutrófilos/metabolismo , Elastasa Pancreática/antagonistas & inhibidores , Agua de Mar , Esteroles/farmacología , Relación Estructura-Actividad , TaiwánRESUMEN
Six new 9-hydroxybriarane diterpenoids, briarenolides ZI-ZVI (1-6), were isolated from a gorgonian coral Briareum sp. The structures of briaranes 1-6 were elucidated by spectroscopic methods and by comparison of their spectroscopic data with those of related analogues. Briarenolides ZII (2) and ZVI (6) were found to significantly inhibit the expression of the pro-inflammatory inducible nitric oxide synthase (iNOS) protein of lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells.
Asunto(s)
Antozoos/química , Antiinflamatorios/química , Antiinflamatorios/farmacología , Diterpenos/química , Diterpenos/farmacología , Macrófagos/efectos de los fármacos , Animales , Antiinflamatorios/aislamiento & purificación , Línea Celular , Diterpenos/aislamiento & purificación , Lipopolisacáridos/inmunología , Macrófagos/inmunología , Ratones , Modelos Moleculares , Óxido Nítrico Sintasa de Tipo II/antagonistas & inhibidores , Óxido Nítrico Sintasa de Tipo II/inmunologíaRESUMEN
A natural caulerpenyne-derived sesquiterpene, oxytoxin-2 (1), was isolated from a cultured mollusc Volvatella vigourouxi. The structure of 1 was elucidated on the basis of spectroscopic analysis and this compound was suggested to be a diet-derived metabolite from the green alga Caulerpa sertularioides.-This is the first study on the chemical constituents of V. vigourouxi. Oxytoxin-2 (1) was found to inhibit significantly the expression of the pro-inflammatory inducible nitric oxide synthase (iNOS) protein of lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells.
Asunto(s)
Antiinflamatorios/farmacología , Chlorophyta/química , Gastrópodos , Óxido Nítrico Sintasa de Tipo II/antagonistas & inhibidores , Sesquiterpenos/farmacología , Animales , Antiinflamatorios/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Dieta , Humanos , Lipopolisacáridos/farmacología , Ratones , Células RAW 264.7 , Sesquiterpenos/aislamiento & purificaciónRESUMEN
In this study, the complete mitogenome sequence of cyprinid fish, Holland's spinibarbel Spinibarbus hollandi Oshima (1919) (Cypriniformes, Cyprinidae, Barbinae) has been amplified and sequenced by employing long polymerase chain reaction method. The mitogenome, consisting of 16,523 base pairs (bp), had the typical vertebrate mitochondrial gene arrangement, including 13 protein-coding genes, 22 transfer RNAs, 2 ribosomal RNAs genes, and a non-coding control region (CR). CR of 867 bp length is located between tRNA(Pro) and tRNA(Phe). The overall base composition of S. hollandi is 31.87% for A, 26.56% for C, 25.89% for T, and 15.68% for G, with a slight AT bias of 57.76%. The complete mitogenome may provide rather essential and important DNA molecular data for further phylogenetic analysis for not only congeneric species but also higher different taxa of Cyprinid fishes.
Asunto(s)
Cyprinidae/genética , Genoma Mitocondrial , Animales , Emparejamiento Base/genética , Secuencia de Bases , Genes Mitocondriales , Países Bajos , ARN de Transferencia/genéticaRESUMEN
Two new 24-homoscalarane sesterterpenoids, felixins F (1) and G (2), were isolated from the sponge Ircinia felix. The structures of new homoscalaranes 1 and 2 were elucidated by extensive spectroscopic methods, particularly with one-dimensional (1D) and two-dimensional (2D) NMR, and, by comparison, the spectral data with those of known analogues. The cytotoxicity of 1 and 2 against the proliferation of a limited panel of tumor cell lines was evaluated and 1 was found to show cytotoxicity toward the leukemia K562, MOLT-4, and SUP-T1 cells (IC50 ≤ 5.0 µM).
Asunto(s)
Poríferos/química , Sesterterpenos/química , Sesterterpenos/toxicidad , Animales , Línea Celular , Proliferación Celular/efectos de los fármacos , Humanos , Estructura MolecularRESUMEN
A new hydroperoxycembranoidal diterpene, trocheliolide A (1), was isolated from the octocoral Sarcophyton trocheliophorum. The structure of 1 was elucidated on the basis of spectroscopic and mass spectrometric methods.