ABSTRACT
Chemical constituents in soft coral Sarcophyton glaucum were separated and purified by various chromatographic methods. Based on the spectral data, physicochemical properties, and comparison with the data reported in the literature, nine cembranoids, including a new cembranoid named sefsarcophinolide(1) together with eight known cembranoids, namely(+)-isosarcophine(2), sarcomilitatin D(3), sarcophytonolide J(4),(1S,3E,7E,13S)-11,12-epoxycembra-3,7,15-triene-13-ol(5), sarcophytonin B(6),(-)-eunicenone(7), lobophytin B(8), and arbolide C(9), were identified. As revealed by biological activity experiment results, compounds 2-6 had weak acetylcholinesterase inhibitory activity, and compound 5 displayed weak cytotoxicity against K562 tumor cell line.
Subject(s)
Animals , Anthozoa , Acetylcholinesterase , Cell Line, TumorABSTRACT
The crude Et2O extract of soft coral Sarcophyton glaucum, collected off the Xisha, the South China Sea, were investigated. A new cembrane-type diterpenoid, namely 15-dehydroxy-sarcophytrol D (1), together with twenty-five known compounds, namely ximaoglaucumin C (2), (11S,12S,1E,3E,7E)-11,12-epoxycembra-1,3,7-triene (3), sarcophytol W (4), cembrene (5), sarcophytol B (6), sarcophytol K (7), sarcophytol J (8), pentaene-cembrene (9), sarcophytol E (10), (+)-marasol (11), (2S)-sarcophytoninsarcophytoxide (12), (-)-17-hydroxydeepoxysarcophytoxide (13), (+)-sarcophytoxide (14), 13-acetoxysarcophytoxide (15), bophynin B (16), 16-oxosarcophytoxide E (17), sarcophinone (18), 7α-8β-dihydroxydeepoxysarcophine (19), (+)-sarcophine (20), 14-dehydroxy-sarcophytol L (21), sarcophytol L (22), 13α-hydroxy-sarcophytol L (23), trocheliophol C (24), trocheliophol E (25) and trocheliophol L (26), were isolated and purified by comprehensive chromatography methods of silica gel column, Sephadex LH-20 gel column, TLC, and semi-preparative high-performance liquid chromatography (HPLC). In anti-inflammatory bioassay, compound 4 exhibited inhibitory effects on lipopolysaccharide (LPS)-induced inflammatory responses in BV-2 microglial cells.
ABSTRACT
Lobane-type diterpenoids are not frequently discovered from marine soft corals. In this paper, three new lobane type diterpenes, 13-methoxyloba-8,10,15(16),17(18)-tetraene (1), 8,10,13(15)Z,16E-lobatetraene (2) and 19-hydroxy-lobatetraene (3), and a new natural compound, 17,18-epoxyloba-16-acetoxy-8,10,13(15)-trien (4), co-occurring with a known related diterpenoid, 18-methoxyloba-8,10,13(15),16(17)-tetraene (5), were isolated from the South China Sea soft coral Sinularia polydactyla. The structures of new compounds were determined by extensive spectroscopic analysis and by comparison with those reported in the literature. In bioassay, all the isolates were inactive on antibacterial, PTP1B inhibitory, and immunological activities. This study increased the chemical diversity of marine diterpenoids.
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Globally, peptide-based anticancer therapies have drawn much attention. Marine organisms are a reservoir of anticancer peptides that await discovery. In this study, we aimed to identify cytotoxic oligopeptides from Sarcophyton glaucum. Peptides were purified from among the S. glaucum hydrolysates produced by alcalase, chymotrypsin, papain, and trypsin, guided by a methylthiazolyldiphenyl-tetrazolium bromide (MTT) assay on the human cervical cancer (HeLa) cell line for cytotoxicity evaluation. Purification techniques adopted were membrane ultrafiltration, gel filtration chromatography, solid phase extraction (SPE), and reversed-phase high-performance liquid chromatography (RP-HPLC). Purified peptides were identified by de novo peptide sequencing. From papain hydrolysate, three peptide sequences were identified: AGAPGG, AERQ, and RDTQ (428.45, 502.53, and 518.53 Da, respectively). Peptides synthesized from these sequences exhibited cytotoxicity on HeLa cells with median effect concentration (EC50) values of 8.6, 4.9, and 5.6 mmol/L, respectively, up to 5.8-fold stronger than the anticancer drug 5-fluorouracil. When tested at their respective EC50, AGAPGG, AERQ, and RDTQ showed only 16%, 25%, and 11% cytotoxicity to non-cancerous Hek293 cells, respectively. In conclusion, AERQ, AGAPGG, and RDTQ are promising candidates for future development as peptide-based anticancer drugs.
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Eight cembrane-type diterpenoids, namely, (+)-(6)-6-hydroxyisosarcophytoxide (), (+)-(6)-6-acetoxyisosarcophytoxide (), (+)-17-hydroxyisosarcophytoxide (), sarcomililatins A-D (-), and sarcomililatol (), were isolated from the soft coral collected from Weizhou Island, Guangxi Autonomous Region, together with 2 known related analogues, (+)-isosarcophytoxide () and (+)-isosarcophine (). The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. The absolute configuration of compound was established by the modified Mosher׳s method, while the absolute configurations of compounds and were assigned by electronic circular dichroism (ECD) spectroscopy and that of compound was established by time-dependent density functional theory electronic circular dichroism (TD-DFT ECD) calculation. In bioassays, compound displayed significant cytotoxicity against the human cancer cell lines human promyelocytic leukemia cells (HL-60) and human lung adenocarcinoma cells (A-549) with IC values of 0.78±0.21 and 1.26±0.80 μmol/L, respectively. Compounds and also showed moderate inhibitory effects on the TNF-induced Nuclear factor kappa B (NF-B, a therapeutical target in cancer) activation, showing IC values of 35.23±12.42 and 22.52±4.44 μmol/L, respectively.
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Objective: To investigate the chemical constituents of South China Sea soft coral Sinularia sp. Methods: Compounds were isolated and purified by column chromatography on silica gel and Sephadex LH-20. Their structures were identified on the basis of mass (MS) and nuclear magnetic resonance (NMR) spectral data. Results: Eleven compounds were isolated and identified as cholesterol (1), 3β-hydroxycholest-5-en-7-one (2), 3β-hydroxyergosta-5,24(28)-dien-7-one (3), campesterol (4), 24-methylene- cholesterol (5), ergosterol peroxide (6), axinysterol (7), ergosterol (8), (3β,4α,5α,8β)-4-methylergost-24 (28)-ene-3,8-diol (9), arachidonic acid (10), and methyl arachidonate (11). Conclusion: Compounds 1-9 belong to sterols with three different types, while compounds 10 and 11 are unsaturated lipids. Moreover, compounds 7 and 11 are obtained from the soft corals of genus Sinularia sp. for the first time.
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In the present study, two new trinor-guaiane sesquiterpenes, named clavuridins B (1), and A (2), along with three known sesquiterpenes (3-5), were isolated from the Xisha soft coral Clavularia viridis. Their structures and absolute configurations were determined on the basis of spectroscopic analysis, X-ray diffraction analysis with Cu Kα radiation and by comparison with related model compounds. Compounds 1 and 3-5 were evaluated for their cytotoxic activity.
Subject(s)
Animals , Anthozoa , Chemistry , Biological Products , Chemistry , Pharmacology , Magnetic Resonance Spectroscopy , Molecular Structure , Sesquiterpenes, Guaiane , Chemistry , PharmacologyABSTRACT
The flux of carbon within the coralline ecosystem has been a subject of great interest in the recent decades. So far several studies had been conducted to understand actual process of carbon transfer within this system and it is an elusive factor on science because of the complex process. An attempt had been made to delineate the source and sink of carbon within the coral ecosystem by establishing small experimental set up in the present study. For these study, four experimental tanks, each consisted of a different community of coral ecosystem was set up in Pondicherry University, Port Blair, Andaman Islands, India. The Tank A was set up with a most prevalent sponge species Stylissa massa, in this part of the study area, Tank B consisted of sponge Lamellodysidea spp., Tank C consisted of macroalgae community i.e. of Padina spp. of an area of 620 cm2 and Tank D had a soft coral Sarcophyton spp. All these species were collected from Burmanallha, a region characterized by rich species diversity. The results indicated that the algal and sponge community provided carbon to support the growth of coral reefs. Coral utilized this carbon for their growth. It was also observed that fluctuation of environmental and physical parameters induced biological stress within the life forms resulted in the release of excess inorganic carbon to the surrounding water. Whenever, the opportunity were available this carbon was utilized by the system itself and managed full extent without any excess carbon.
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Objective: To investigate the chemical constituents in soft coral Lobophytum sp. collected from the Xisha islands of China. Methods: Compounds were isolated and purified by column chromatographies on silica gel, reversed-phase silica gel (ODS), Sephadex LH-20, and high performance liquid chromatography (HPLC). Their structures were identified on the basis of physicochemical properties and spectroscopic methods. Results: Five compounds were isolated and identified as 11,12-epoxy-sarcophytonin E (1), cholest-5,22-dien-3β-ol (2), honulactone A (3), sarcophytonone (4), and 3-dehydroxyl-20-acetylpresinularolide B (5). Conclusion: Compound 1 is a new compound named as chiloboterpene A. Compounds 2-4 are obtained from the soft coral Lobophytum sp. for the first time.
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Objective: To study the chemical constituents of a kind of soft coral Lobophytum sp. collected from Xisha islands of China. Methods: Isolation and purification of the chemical constituents were performed by silica gel and ODS gel column chromatographies as well as HPLC. Their structures were determined on the basis of physicochemical properties and spectroscopic methods. Results: Six diterpenoids were obtained in 95% ethanol extract from Lobophytum sp., including chilobolide B (1), (1S*,3S*,4S*,7E,11E)-3,4-epoxy-13-oxo-7,11,15-cembratriene (2), (2E,4E,7R,8S,12Z)-1-isopropylcyclotetradeca-4,8-dimethyl-7-hydroxy-1,3,11-triene-8,12-carbolactone (3), (2E,4E,8S,12Z)-1-isopropyl-4,8-dimethyl-7-oxocyclotetradeca-l,3,11-triene-8,12-carbolactone (4), sarcrassin D (5), and laevigatol B (6). Conclusion: Compound 1 is a new compound named chilobolide B. Compounds 2-4 are obtained from Lobophytum sp. for the first time.
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Cembranoid type diterpenes are important natural products which have novel structures and remarkable bioactivities. Cembranoid type diterpenes obtained now included isopropyl type, five, six, seven, eight membered lactone ring, open ring, reducing carbon types, etc, with cytotoxicity and antitumor activity. This paper reviews the structures and bioactivities of 193 cembranoid diterpenes which have been discovered since 2007, providing the scientific evidence for reasonable exploitation and application of cembranoid diterpenes.
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AIM@#To study the minor diterpenes from the soft coral Sinularia depressa@*METHOD@#The chemical constituents were isolated and purified by various chromatographic techniques, and the chemical structures, including absolute configuration, were established on the basis of detailed analysis of spectroscopic data and by literature comparison with the data of related known compounds.@*RESULTS@#A new casbane-type diterpene, 2-epi-10-hydroxydepressin (1), was isolated and identified.@*CONCLUSION@#Compound 1 is a new casbane-type diterpene.
Subject(s)
Animals , Anthozoa , Chemistry , Diterpenes , Heterocyclic Compounds, 3-Ring , Hexamethonium , Spectrum AnalysisABSTRACT
This review reported the structural diversity and novelty of the secondary metabolites derived from eight marine corals in the south China sea. The structural patterns from eight coral species were summarized, in which 130 new compounds of a total of 155 derivatives were uncovered. Some of the secondary metabolites showed potent anti-fouling and anti-cancer activities. These findings ndicated that marine organisms can provide structurally unique compounds for further pharmacological evaluation.
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Objective To find new compound from soft corals.Methods The chloroform portion of the soft coral Sinularia sp.was subjected to silica gel to give ceramide(Ⅰ).Results Structure of compound(Ⅰ) was identified as 2S,3S,4R-N-octadecanoyl-phytosphingosine on the bases of spectroscopic(IR,MS,NMR) and chemical analyses.Conclusion Compound(Ⅰ) was a new natural ceramide and its IR, NMR data were reported here for the first time.
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Seven crystalline compounds have been isolated from the soft coral Nephthea Bayer collected from the South China Sea, four of them have been identified to be 24-methyl-cholesta-5,24 (28 )-diene-3B, 7B,19-triol (1) , 24-methylcholesta-5, 24 (28)-diene-3B,19-diol (2), 24-methylcholesta-5,24(28)-diol-3B-ol (3) and l-octadecyl-2,3-dihydroxypropyl ether (4), respectively based on their data of IR, MS, 1HNMR and 13CNMR.
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The chemical constituents of the soft coral Nephthea brassica collected from the South China Sea have been studied. Two ceramides 1 and 2 were isolated. The ceramide 1 is a white powder with a formula C37H75NO4, mp 113-114C, and 2 is a white powder with a formula C34H67NO3, mp 89-90C. The structures of 1 and 2 were, respectively, designated as N-2-(1 , 3, 5-tri-hydroxy octadecyl)-nonadecamide and (E)-N-2-(1, 3-dihydroxy octadecan-4-en)-hexadecamide by spectroscopic analysis and elemental analysis. The ceramide 1 was discovered in the nature for the first time.
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Objective Secondary metabolites of the soft coral were studied to find out the lead compound of the drugs. Methods Compounds from the soft coral Sinularia papillosa were obtained by column chromatography and modern isolation methods and their structures were identified by spectrum of UV,IR,NMR,MS,et al. Results Two white amorphous compounds were obtained from the EtOAc (ethyl acetate) fraction,and their structures were identified as pregn-5,20 -dien-3?-ol-3-O-?-L-fucopyranoside (1) and 1-(17Z-tetracose-nyloxy)-1,2 -propanediol (2) by spectral analysis. Conclusion Two compounds are first isolated from the soft coral genus Sinularia,which will be beneficial for the taxonomy of the soft coral and for biogenesis of steroids.