In our continuing search of discovering bioactive substances from marine organisms, a sample of soft coral Sarcophyton crassocaule Mosre collected off the Sanya bay, China, was investigated. Two polyhydroxylated stero...In our continuing search of discovering bioactive substances from marine organisms, a sample of soft coral Sarcophyton crassocaule Mosre collected off the Sanya bay, China, was investigated. Two polyhydroxylated sterols 1 and 2 were isolated from the 95% ethanol extract of the sample by chromatography over silica gel. Compound 1, named sarcrasterol, was a new compound, its structure was established as(22R*,24ξ)-methyl-cholest-5-en-3β,22α,25,28-tetraol by spectroscopic methods. Compound 2, a known compound, was first obtained by Kobayashi, however, the relative configuration of C24 has not been determined yet. This paper reports the stereochemistry of compound 2 established as (24S*)-methyl cholest-3β,5β,6α,25-tetraol by means of X-ray single crystal diffraction analysis. Bioassay results show that compound 2 has a moderate activity against human tumor cell lines MGC-803 with an IC50 value of 23.0 μg/mL.展开更多
To investigate the cembranoid diterpenes from the soft coral Sarcophyton sp. collected in the South China Sea. Repeatedly column chromatography was performed for the isolation and purification. The structures were elu...To investigate the cembranoid diterpenes from the soft coral Sarcophyton sp. collected in the South China Sea. Repeatedly column chromatography was performed for the isolation and purification. The structures were elucidated on the basis of extensive spectral data （IR, MS, 1 D- and 2D-NMR） analysis by comparing with literature data. A new cembranoid diterpene namely sarcophyolide A （1）, together with 7a, 8β-dihydroxydeepoxysarcophine （2） were isolated from this species. The cembranoid diterpenes with 7-1actone could be chemotaxonomic markers of Sarcophyton sp.展开更多
Many cembranes, 14 membered ring diterpenoids, were reported to have antitumor and antimicrobial activities. Soft corals are rich sources of cembrenoid diterpenes. We reported cembrenoids lactones, such as sarcophinon...Many cembranes, 14 membered ring diterpenoids, were reported to have antitumor and antimicrobial activities. Soft corals are rich sources of cembrenoid diterpenes. We reported cembrenoids lactones, such as sarcophinone, iso sarcophinone, sarcophine, sartrochine from the species of Sarcophyton in our earlier papers,. In continuation of our studies on the soft coral Sarcophyton , we obtained a new cembranoid lactone, named sarcophydiol(1) from a specimen of Sarcophyton sp . collected around the bay of Sanya, Hainan Island. On the basis of spectroscopic methods, its structure was determined as ( 10S *,11S *) 3,7,11α ,15 tetramethyl 10 β,11β dihydroxy cembr 2 E,6E,14(15)Z trien 16,1 olide(1). The bioactivities of compound 1 were under investigating.展开更多
Three new highly oxidative cembranoids,sarcophytrols D-F(1-3),were obtained from the South China Sea soft coral Sarcophyton trocheliophorum,along with two known related ones(4 and 5).Their structures were elucidated b...Three new highly oxidative cembranoids,sarcophytrols D-F(1-3),were obtained from the South China Sea soft coral Sarcophyton trocheliophorum,along with two known related ones(4 and 5).Their structures were elucidated by extensive spectroscopic analyses and by comparison with literature data.The discovery of these new secondary metabolites enriched the family of cembranoids deduced from the title animal.展开更多
Eighteen specimens of the soft coral Sarcophyton glaucum have been collected and tagged to determine the growth rate using the weight variations technique and to investigate the reproductive season histologically. Six...Eighteen specimens of the soft coral Sarcophyton glaucum have been collected and tagged to determine the growth rate using the weight variations technique and to investigate the reproductive season histologically. Six colonies were totally weighed and 12 fragments (produced from three colonies) were marked and weighed. Some samples showed sever shrinkage that lead to death. The maximum semiannual growth rate was recorded in summer (30.05 gm/6 m). The average monthly growth reached 3.95 gm/month. Many factors affect the growth rate such as water currents, turbidity, sedimentation, temperature and reproduction process. The studied species is a dioecious species (unisex), where the Autozooid polyps are the reproductive organs while siphonozooids are sterile. Female gonads were observed to develop at late July before male gonads which began at late September. Larvae releasing started at late January and the gonads are completely spawned in February. Fertilization occurs internally to form planulae larvae which librated completely in February. The oogenesis exhibited prolonged about 23 months, which gave rise to oocytes of different developmental stages in female colonies at any given time, and a spermatogenic cycle of only 10 - 12 months.展开更多
Backgroundand Originality Content,Cembranoids are a structurally diverse class of diterpenoids commonly occurring in marine and terrestrial organisms.(+)-Cembrene was the first reported cembranoid diterpenoid discover...Backgroundand Originality Content,Cembranoids are a structurally diverse class of diterpenoids commonly occurring in marine and terrestrial organisms.(+)-Cembrene was the first reported cembranoid diterpenoid discovered in 1962,l and more than 1400 cembranoid diterpenoids have been identified in the last six decades,[2]Cembranoids are characterized by a 14-membered carbocyclic ring,an isopropyl group and three methyl groups,which form their core carbon skeleton.Enzymatic processes such as oxidation,oxidative rearrangements and transannular cyclizations occur in organisms,leading to the formation of distinctive specialized metabolites such as epoxide,lactone,ester,furan,pyrane and other ringbased cembranoids.[2-3]展开更多
Eight cembrane-type diterpenoids, namely,(t)-(6 R)-6-hydroxyisosarcophytoxide(1),(t)-(6 R)-6-acetoxyisosarcophytoxide(2),(t)-17-hydroxyisosarcophytoxide(3), sarcomililatins A–D(4–7), and sarcomililatol(8), were isol...Eight cembrane-type diterpenoids, namely,(t)-(6 R)-6-hydroxyisosarcophytoxide(1),(t)-(6 R)-6-acetoxyisosarcophytoxide(2),(t)-17-hydroxyisosarcophytoxide(3), sarcomililatins A–D(4–7), and sarcomililatol(8), were isolated from the soft coral Sarcophyton mililatensis collected from Weizhou Island, Guangxi Autonomous Region, together with 2 known related analogues,(t)-isosarcophytoxide(9) and(t)-isosarcophine(10). 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 1 was established by the modified Mosher's method, while the absolute configurations of compounds 4 and 5 were assigned by electronic circular dichroism(ECD)spectroscopy and that of compound 8 was established by time-dependent density functional theory electronic circular dichroism(TD-DFT ECD) calculation. In in vitro bioassays, compound 9 displayed significant cytotoxicity against the human cancer cell lines human promyelocytic leukemia cells(HL-60)and human lung adenocarcinoma cells(A-549) with IC_(50) values of 0.7870.21 and 1.2670.80 μmol/L,respectively. Compounds 4 and 9 also showed moderate inhibitory effects on the TNFα-induced Nuclear factor kappa B(NF-κB, a therapeutical target in cancer) activation, showing IC_(50) values of 35.23712.42 and 22.5274.44 μmol/L, respectively.展开更多
Ten new cembrane-type diterpenoids,namely xishaglaucumins A—J(1—10),along with ten known related ones(11—20),have been isolated from the soft coral Sarcophyton glaucum collected off the Xisha Island in the South Ch...Ten new cembrane-type diterpenoids,namely xishaglaucumins A—J(1—10),along with ten known related ones(11—20),have been isolated from the soft coral Sarcophyton glaucum collected off the Xisha Island in the South China Sea.Their structures were elucidated by extensive spectroscopic analysis,quantum mechanical nuclear magnetic resonance(QM-NMR)methods,X-ray diffraction analysis,chemical methods and comparison with the reported data in the literature.The absolute configuration of new compounds 1,5 and known compounds 11,12,16 and 20 were determined either by chemical methods or by X-ray diffraction analysis using Cu Kα(λ=1.5417A).In in vitro bioassay,compound 4 exhibited inhibitory effects on lipopolysaccharide(LPS)-induced inflammatory responses in BV-2 microglial cells.展开更多
A novel hydroperoxide cembrane-type diterpenoid was isolated from the soft coral Sarcophyton crassocaule collected from the Xisha Islands in the South China Sea. The structure of 3 was established by spectroscopy and ...A novel hydroperoxide cembrane-type diterpenoid was isolated from the soft coral Sarcophyton crassocaule collected from the Xisha Islands in the South China Sea. The structure of 3 was established by spectroscopy and X-ray diffraction analysis,named as sarcophyocrassolide A. It exhibited strong cytotoxicity against the P-388 cell line with IC_ 50 value of 0.1 μg/mL.展开更多
Five novel biscembranoids,ximaolides H-L(1-5),along with four known related compounds(6-9) were isolated from the Hainan soft coral Sarcophyton tortuosum.The structures of the new compounds were determined by extensiv...Five novel biscembranoids,ximaolides H-L(1-5),along with four known related compounds(6-9) were isolated from the Hainan soft coral Sarcophyton tortuosum.The structures of the new compounds were determined by extensive spectroscopic analysis,quantum chemical calculations,and/or by comparing their CD spectra with those of the known compounds.Compounds 1 and 2 are the first examples of biscembranoids bearing a 1,35-bridged lactone moiety,4 is the first biscembranoid comprising an uncommon oxetane ring,and 5 represents the first 36-peroxyl biscembranoid.Ximaolides Ⅰ(2),K(4) and F(9) exhibited interesting anti-inflammatory activity by the inhibition of LPS-induced TNF-α protein release in RAW264.7 macrophages.展开更多
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 Sa...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.展开更多
A novel sarsolenane diterpene, named secodihydrosarsolenone （1）, as a minor component was obtained from the South China Sea soft coral Sarcophyton trocheliophorum Marenzeller. Its structure was elucidated by detaile...A novel sarsolenane diterpene, named secodihydrosarsolenone （1）, as a minor component was obtained from the South China Sea soft coral Sarcophyton trocheliophorum Marenzeller. Its structure was elucidated by detailed spectroscopic analysis. Compound 1 exhibited moderate inhibitory activity （IC50= 13.7 μmol·L^-1） against protein tyrosine phosphatase 1B （PTP1B）, a key target for the treatment of type 2 diabetes, representing the first report of PTP1B inhibitory activity for sarsolenane diterpenes. This discovery promotes computational prediction of binding mode between the enzyme and the metabolite, suggesting a crucial role of the residues Tyr46, Ser216 and Arg221 in the binding action.展开更多
文摘In our continuing search of discovering bioactive substances from marine organisms, a sample of soft coral Sarcophyton crassocaule Mosre collected off the Sanya bay, China, was investigated. Two polyhydroxylated sterols 1 and 2 were isolated from the 95% ethanol extract of the sample by chromatography over silica gel. Compound 1, named sarcrasterol, was a new compound, its structure was established as(22R*,24ξ)-methyl-cholest-5-en-3β,22α,25,28-tetraol by spectroscopic methods. Compound 2, a known compound, was first obtained by Kobayashi, however, the relative configuration of C24 has not been determined yet. This paper reports the stereochemistry of compound 2 established as (24S*)-methyl cholest-3β,5β,6α,25-tetraol by means of X-ray single crystal diffraction analysis. Bioassay results show that compound 2 has a moderate activity against human tumor cell lines MGC-803 with an IC50 value of 23.0 μg/mL.
基金National Natural Science Foundation of China(Grant No.30672607)the National Hi-Tech Projects(Grant No.2006AA09Z446,2006DFA31100 and 2006AA09Z405)+1 种基金China Uni-PhD Base Project(Grant No.20060001149)International Cooperation Projects of BMBF-MOST.
文摘To investigate the cembranoid diterpenes from the soft coral Sarcophyton sp. collected in the South China Sea. Repeatedly column chromatography was performed for the isolation and purification. The structures were elucidated on the basis of extensive spectral data （IR, MS, 1 D- and 2D-NMR） analysis by comparing with literature data. A new cembranoid diterpene namely sarcophyolide A （1）, together with 7a, 8β-dihydroxydeepoxysarcophine （2） were isolated from this species. The cembranoid diterpenes with 7-1actone could be chemotaxonomic markers of Sarcophyton sp.
文摘Many cembranes, 14 membered ring diterpenoids, were reported to have antitumor and antimicrobial activities. Soft corals are rich sources of cembrenoid diterpenes. We reported cembrenoids lactones, such as sarcophinone, iso sarcophinone, sarcophine, sartrochine from the species of Sarcophyton in our earlier papers,. In continuation of our studies on the soft coral Sarcophyton , we obtained a new cembranoid lactone, named sarcophydiol(1) from a specimen of Sarcophyton sp . collected around the bay of Sanya, Hainan Island. On the basis of spectroscopic methods, its structure was determined as ( 10S *,11S *) 3,7,11α ,15 tetramethyl 10 β,11β dihydroxy cembr 2 E,6E,14(15)Z trien 16,1 olide(1). The bioactivities of compound 1 were under investigating.
基金This research work was financially supported by the National Marine“863”Projects(Nos.2013AA092902 and 2012AA092105)the Natural Science Foundation of China(Nos.81520108028,81273430,41506187,41306130,41476063)+3 种基金NSFC Shangdong Joint Fund for Marine Science Research Centers(Grant No.U1406402)SCTSM Project(No.14431901100 and 15431901000)the SKLDR/SIMM Projects(SIMM1203ZZ-03 and 1501ZZ-03)was partially funded by the EU 7th Framework Programme-IRSES Project(No.246987).
文摘Three new highly oxidative cembranoids,sarcophytrols D-F(1-3),were obtained from the South China Sea soft coral Sarcophyton trocheliophorum,along with two known related ones(4 and 5).Their structures were elucidated by extensive spectroscopic analyses and by comparison with literature data.The discovery of these new secondary metabolites enriched the family of cembranoids deduced from the title animal.
文摘Eighteen specimens of the soft coral Sarcophyton glaucum have been collected and tagged to determine the growth rate using the weight variations technique and to investigate the reproductive season histologically. Six colonies were totally weighed and 12 fragments (produced from three colonies) were marked and weighed. Some samples showed sever shrinkage that lead to death. The maximum semiannual growth rate was recorded in summer (30.05 gm/6 m). The average monthly growth reached 3.95 gm/month. Many factors affect the growth rate such as water currents, turbidity, sedimentation, temperature and reproduction process. The studied species is a dioecious species (unisex), where the Autozooid polyps are the reproductive organs while siphonozooids are sterile. Female gonads were observed to develop at late July before male gonads which began at late September. Larvae releasing started at late January and the gonads are completely spawned in February. Fertilization occurs internally to form planulae larvae which librated completely in February. The oogenesis exhibited prolonged about 23 months, which gave rise to oocytes of different developmental stages in female colonies at any given time, and a spermatogenic cycle of only 10 - 12 months.
基金supported by the National Natural Science Foundation of China(No.U2006204).
文摘Backgroundand Originality Content,Cembranoids are a structurally diverse class of diterpenoids commonly occurring in marine and terrestrial organisms.(+)-Cembrene was the first reported cembranoid diterpenoid discovered in 1962,l and more than 1400 cembranoid diterpenoids have been identified in the last six decades,[2]Cembranoids are characterized by a 14-membered carbocyclic ring,an isopropyl group and three methyl groups,which form their core carbon skeleton.Enzymatic processes such as oxidation,oxidative rearrangements and transannular cyclizations occur in organisms,leading to the formation of distinctive specialized metabolites such as epoxide,lactone,ester,furan,pyrane and other ringbased cembranoids.[2-3]
基金supported by the Natural Science Foundation of China(Nos.41506187,81520108028,21672230 and 81603022)NSFC-Shandong Joint Fund for Marine Science Research Centers(No.U1606403)+1 种基金SCTSM Project(No.15431901000)the SKLDR/SIMM Projects(SIMM 1705ZZ-01)
文摘Eight cembrane-type diterpenoids, namely,(t)-(6 R)-6-hydroxyisosarcophytoxide(1),(t)-(6 R)-6-acetoxyisosarcophytoxide(2),(t)-17-hydroxyisosarcophytoxide(3), sarcomililatins A–D(4–7), and sarcomililatol(8), were isolated from the soft coral Sarcophyton mililatensis collected from Weizhou Island, Guangxi Autonomous Region, together with 2 known related analogues,(t)-isosarcophytoxide(9) and(t)-isosarcophine(10). 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 1 was established by the modified Mosher's method, while the absolute configurations of compounds 4 and 5 were assigned by electronic circular dichroism(ECD)spectroscopy and that of compound 8 was established by time-dependent density functional theory electronic circular dichroism(TD-DFT ECD) calculation. In in vitro bioassays, compound 9 displayed significant cytotoxicity against the human cancer cell lines human promyelocytic leukemia cells(HL-60)and human lung adenocarcinoma cells(A-549) with IC_(50) values of 0.7870.21 and 1.2670.80 μmol/L,respectively. Compounds 4 and 9 also showed moderate inhibitory effects on the TNFα-induced Nuclear factor kappa B(NF-κB, a therapeutical target in cancer) activation, showing IC_(50) values of 35.23712.42 and 22.5274.44 μmol/L, respectively.
基金financially supported by the National Natural Science Foundation of China(Nos.81991521,41776093)the National Key Research and Development Program of China(No.2018YFC0310903)+2 种基金the Key Research and Development Project of Hainan Province(ZDYF2021SHFZ107)Financial Fund of the Ministry of Agriculture and Rural Affairs,P.R.China(NFZX2021)the SKLDR/SIMM Project(No.SIMM2103ZZ-06).
文摘Ten new cembrane-type diterpenoids,namely xishaglaucumins A—J(1—10),along with ten known related ones(11—20),have been isolated from the soft coral Sarcophyton glaucum collected off the Xisha Island in the South China Sea.Their structures were elucidated by extensive spectroscopic analysis,quantum mechanical nuclear magnetic resonance(QM-NMR)methods,X-ray diffraction analysis,chemical methods and comparison with the reported data in the literature.The absolute configuration of new compounds 1,5 and known compounds 11,12,16 and 20 were determined either by chemical methods or by X-ray diffraction analysis using Cu Kα(λ=1.5417A).In in vitro bioassay,compound 4 exhibited inhibitory effects on lipopolysaccharide(LPS)-induced inflammatory responses in BV-2 microglial cells.
基金ProjectsupportedbytheKeyScienceFoundationofTianjin (No .0 13 80 44 11)
文摘A novel hydroperoxide cembrane-type diterpenoid was isolated from the soft coral Sarcophyton crassocaule collected from the Xisha Islands in the South China Sea. The structure of 3 was established by spectroscopy and X-ray diffraction analysis,named as sarcophyocrassolide A. It exhibited strong cytotoxicity against the P-388 cell line with IC_ 50 value of 0.1 μg/mL.
基金financially supported by the National Natural Science Foundation of China(NSFC,Nos.81991521,8202290170,42076099)the NSFC/CNRS(Centre National de la Recherche Scientifique)Joint Project(No.81811530284)+3 种基金the National Key Research and Development Program of China(No.2018YFC0310903)the SKLDR/SIMM Project(No.SIMM1903ZZ-04)the Shanghai Rising-Star Program(No.20QA1411100)SA-SIBS Scholarship Program。
文摘Five novel biscembranoids,ximaolides H-L(1-5),along with four known related compounds(6-9) were isolated from the Hainan soft coral Sarcophyton tortuosum.The structures of the new compounds were determined by extensive spectroscopic analysis,quantum chemical calculations,and/or by comparing their CD spectra with those of the known compounds.Compounds 1 and 2 are the first examples of biscembranoids bearing a 1,35-bridged lactone moiety,4 is the first biscembranoid comprising an uncommon oxetane ring,and 5 represents the first 36-peroxyl biscembranoid.Ximaolides Ⅰ(2),K(4) and F(9) exhibited interesting anti-inflammatory activity by the inhibition of LPS-induced TNF-α protein release in RAW264.7 macrophages.
基金Project supported by the Fundamental Research Grant Scheme of the Ministry of Higher Education,Malaysia(FRGS/1/2013/ST04/UTAR/02/1)
文摘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.
基金Acknowledgement This research work was financially supported by the National Natural Science Foundation of China （Nos. 41506187, 81520108028, 21672230, 41676073, 81603022）, SCTSM Project （No. 15431901000, 14431901100）, the Hunan Provincial Natural Science Foundation of China （2015JJ3176）, and the SKLDR/SIMM Projects （No. SIMMI501ZZ-03）. Linfu Liang thanks to the financial support of the China Postdoctoral Science Foundation （2016M601677）. The authors are grateful to Mr. Li-Gong Yao of State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, CAS, for his valuable work on collection of the sample.
文摘A novel sarsolenane diterpene, named secodihydrosarsolenone （1）, as a minor component was obtained from the South China Sea soft coral Sarcophyton trocheliophorum Marenzeller. Its structure was elucidated by detailed spectroscopic analysis. Compound 1 exhibited moderate inhibitory activity （IC50= 13.7 μmol·L^-1） against protein tyrosine phosphatase 1B （PTP1B）, a key target for the treatment of type 2 diabetes, representing the first report of PTP1B inhibitory activity for sarsolenane diterpenes. This discovery promotes computational prediction of binding mode between the enzyme and the metabolite, suggesting a crucial role of the residues Tyr46, Ser216 and Arg221 in the binding action.
