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1.
Molecules ; 25(6)2020 Mar 19.
Artigo em Inglês | MEDLINE | ID: mdl-32204524

RESUMO

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.

2.
BMC Genet ; 20(1): 86, 2019 11 21.
Artigo em Inglês | MEDLINE | ID: mdl-31752677

RESUMO

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.

3.
Mar Drugs ; 17(9)2019 Sep 14.
Artigo em Inglês | MEDLINE | ID: mdl-31540107

RESUMO

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.


Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Óxido Nítrico Sintase Tipo II/metabolismo , Espectroscopia de Prótons por Ressonância Magnética , Células RAW 264.7 , Relação Estrutura-Atividade
4.
Mar Drugs ; 17(4)2019 Apr 05.
Artigo em Inglês | MEDLINE | ID: mdl-30959843

RESUMO

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 1⁻3 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.


Assuntos
Antozoários/química , Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Diterpenos/química , Diterpenos/isolamento & purificação , Camundongos , Modelos Moleculares , Estrutura Molecular , Células RAW 264.7
5.
Mar Drugs ; 16(9)2018 Sep 17.
Artigo em Inglês | MEDLINE | ID: mdl-30227646

RESUMO

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.


Assuntos
Antozoários/metabolismo , Antibacterianos/química , Anti-Inflamatórios/química , Antifúngicos/química , Produtos Biológicos/química , Animais , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/metabolismo , Estrutura Molecular , Oceano Pacífico
6.
Mitochondrial DNA A DNA Mapp Seq Anal ; 29(5): 687-694, 2018 07.
Artigo em Inglês | MEDLINE | ID: mdl-28712317

RESUMO

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.


Assuntos
/genética , Complexo IV da Cadeia de Transporte de Elétrons/genética , Animais , DNA Mitocondrial/genética , Água Doce , Variação Genética , Genética Populacional/métodos , Genoma Mitocondrial/genética , Mitocôndrias/genética , Filogenia , Rios , Análise de Sequência de DNA/métodos , Frutos do Mar , Taiwan
7.
Bioorg Med Chem Lett ; 26(20): 4966-4969, 2016 10 15.
Artigo em Inglês | MEDLINE | ID: mdl-27623548

RESUMO

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.


Assuntos
Antozoários/metabolismo , Noresteroides/química , Noresteroides/farmacologia , Esteróis/química , Esteróis/farmacologia , Animais , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Espectroscopia de Prótons por Ressonância Magnética , Relação Estrutura-Atividade , Taiwan
8.
Nat Prod Commun ; 11(6): 707-8, 2016 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-27534096

RESUMO

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.


Assuntos
Antozoários/química , Terpenos/química , Animais , Antozoários/metabolismo , Humanos , Estrutura Molecular , Neutrófilos/efeitos dos fármacos , Neutrófilos/enzimologia , Elastase Pancreática/análise , Elastase Pancreática/metabolismo , Metabolismo Secundário , Terpenos/metabolismo , Terpenos/farmacologia
9.
Steroids ; 115: 123-129, 2016 11.
Artigo em Inglês | MEDLINE | ID: mdl-27553726

RESUMO

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.


Assuntos
Antozoários/química , Antozoários/microbiologia , Esteróis/química , Animais , Espectroscopia de Ressonância Magnética , Estrutura Molecular
10.
Environ Pollut ; 216: 924-934, 2016 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-27400905

RESUMO

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.


Assuntos
Dibenzofuranos Policlorados/análise , Monitoramento Ambiental/métodos , Poluentes Ambientais/análise , Éteres Difenil Halogenados/análise , Bifenilos Policlorados/análise , Dibenzodioxinas Policloradas/análise , Spheniscidae/metabolismo , Animais , Regiões Antárticas , Dibenzofuranos Policlorados/farmacocinética , Poluentes Ambientais/farmacocinética , Éteres Difenil Halogenados/farmacocinética , Humanos , Bifenilos Policlorados/farmacocinética , Dibenzodioxinas Policloradas/farmacocinética , Solo/química
11.
Int J Mol Sci ; 17(1)2016 Jan 09.
Artigo em Inglês | MEDLINE | ID: mdl-26761004

RESUMO

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.


Assuntos
Antozoários/química , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Diterpenos/química , Diterpenos/farmacologia , Macrófagos/efeitos dos fármacos , Animais , Anti-Inflamatórios/isolamento & purificação , Linhagem Celular , Diterpenos/isolamento & purificação , Lipopolissacarídeos/imunologia , Macrófagos/imunologia , Camundongos , Modelos Moleculares , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Óxido Nítrico Sintase Tipo II/imunologia
12.
Mar Drugs ; 14(1): 12, 2016 Jan 07.
Artigo em Inglês | MEDLINE | ID: mdl-26751457

RESUMO

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).


Assuntos
Antozoários/química , Esteróis/química , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular Tumoral/efeitos dos fármacos , Humanos , Neutrófilos/efeitos dos fármacos , Neutrófilos/metabolismo , Elastase Pancreática/antagonistas & inibidores , Água do Mar , Esteróis/farmacologia , Relação Estrutura-Atividade , Taiwan
13.
Nat Prod Commun ; 11(12): 1783-1784, 2016 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-30508332

RESUMO

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.


Assuntos
Anti-Inflamatórios/farmacologia , Clorófitas/química , Gastrópodes , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Sesquiterpenos/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Dieta , Humanos , Lipopolissacarídeos/farmacologia , Camundongos , Células RAW 264.7 , Sesquiterpenos/isolamento & purificação
14.
Mitochondrial DNA A DNA Mapp Seq Anal ; 27(3): 1721-3, 2016 05.
Artigo em Inglês | MEDLINE | ID: mdl-25242188

RESUMO

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.


Assuntos
Cyprinidae/genética , Genoma Mitocondrial , Animais , Pareamento de Bases/genética , Sequência de Bases , Genes Mitocondriais , Países Baixos , RNA de Transferência/genética
15.
Nat Prod Commun ; 10(7): 1163-5, 2015 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-26411000

RESUMO

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.


Assuntos
Antozoários/química , Diterpenos/isolamento & purificação , Animais , Diterpenos/química , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Células MCF-7 , Estrutura Molecular
16.
Int J Mol Sci ; 16(9): 21950-8, 2015 Sep 11.
Artigo em Inglês | MEDLINE | ID: mdl-26378524

RESUMO

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).


Assuntos
Poríferos/química , Sesterterpenos/química , Sesterterpenos/toxicidade , Animais , Linhagem Celular , Proliferação de Células/efeitos dos fármacos , Humanos , Estrutura Molecular
17.
Int J Mol Sci ; 16(8): 19508-17, 2015 Aug 18.
Artigo em Inglês | MEDLINE | ID: mdl-26295226

RESUMO

Two eudesmane sesquiterpenoids, verticillatol (1) and 5α-acetoxy-4(14)-eudesmene-1ß-ol (2) and two cembrane diterpenoids, (-)-leptodiol acetate (3) and sinulacembranolide A (4) were isolated from the octocoral Sinularia gaweli and compounds 2-4 are new isolates. The structures of new terpenoids 2-4 were elucidated by spectroscopic methods and by comparison the spectral data with those of known analogues. Terpenoid 4 was found to inhibit the accumulation of the pro-inflammatory inducible nitric oxide synthase (iNOS) protein of the lipopolysaccharide (LPS)-stimulated RAW264.7 marcophage cells.


Assuntos
Antozoários/química , Anti-Inflamatórios/análise , Diterpenos/análise , Sesquiterpenos/análise , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Lipopolissacarídeos/imunologia , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Camundongos , Óxido Nítrico Sintase Tipo II/imunologia , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia
18.
Mar Drugs ; 13(7): 4296-309, 2015 Jul 14.
Artigo em Inglês | MEDLINE | ID: mdl-26184237

RESUMO

Five new scalarane sesterterpenoids, felixins A-E (1-5), were isolated from the Formosan sponge Ircinia felix. The structures of scalaranes 1-5 were elucidated on the basis of spectroscopic analysis. Cytotoxicity of scalaranes 1-5 against the proliferation of a limited panel of tumor cell lines was evaluated.


Assuntos
Poríferos/química , Sesterterpenos/isolamento & purificação , Terpenos/isolamento & purificação , Animais , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Sesterterpenos/farmacologia , Taiwan
19.
Mar Drugs ; 13(2): 1037-50, 2015 Feb 13.
Artigo em Inglês | MEDLINE | ID: mdl-25689566

RESUMO

Two new briarane-type diterpenoids, briarenolides K (1) and L (2), were isolated from an octocoral identified as Briareum sp. The structures of new briaranes 1 and 2 were elucidated by spectroscopic methods. In the in vitro anti-inflammatory effects test, briaranes 1 and 2 were found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein of the lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells.


Assuntos
Antozoários/química , Anti-Inflamatórios não Esteroides/farmacologia , Diterpenos/farmacologia , Animais , Anti-Inflamatórios não Esteroides/química , Cromatografia Líquida de Alta Pressão , Diterpenos/química , Inibidores Enzimáticos/farmacologia , Lipopolissacarídeos/antagonistas & inibidores , Espectroscopia de Ressonância Magnética , Camundongos , Modelos Moleculares , Conformação Molecular , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Células RAW 264.7/efeitos dos fármacos , Espectrofotometria Infravermelho
20.
Int J Mol Sci ; 16(2): 3298-306, 2015 Feb 03.
Artigo em Inglês | MEDLINE | ID: mdl-25654226

RESUMO

A known norcembranoidal diterpene, 5-episinuleptolide (1), along with a new analogue, 4α-hydroxy-5-episinuleptolide (2), were isolated from a cultured-type soft coral Sinularia numerosa. The structures of 1 and 2 were elucidated on the basis of spectroscopic methods and by comparison of the data with those of the related metabolites. Cytotoxicity of metabolites 1 and 2 against a panel of tumor cells is also described. Compound 2 exhibited moderate cytotoxicity toward CCRF-CEM cells with an IC50 value 4.21 µg/mL. Preliminary SAR (structure activity relationship) information was obtained from these two compounds.


Assuntos
Antozoários/química , Diterpenos/química , Animais , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular
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