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
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
Soft corals are well-known as excellent sources of marine-derived natural products.Among them,members of the genera Sar-cophyton,Sinularia,and Lobophytum are especially attractive targets for marine natural product re...Soft corals are well-known as excellent sources of marine-derived natural products.Among them,members of the genera Sar-cophyton,Sinularia,and Lobophytum are especially attractive targets for marine natural product research.In this review,we reported the marine-derived natural products called cembranoids isolated from soft corals,including the genera Sarcophyton,Sinularia,and Lobophytum.Here,we reviewed 72 reports published between 2016 and 2020,comprising 360 compounds,of which 260 are new compounds and 100 are previously known compounds with newly recognized activities.The novelty of the organic molecules and their relevant biological activities,delivered by the year of publication,are presented.Among the genera presented in this report,Sarcophyton spp.produce the most cembranoid diterpenes;thus,they are considered as the most important soft corals for marine natural product research.Cembranoids display diverse biological activities,includ-ing anti-cancer,anti-bacterial,and anti-inflammatory.As cembranoids have been credited with a broad range of biological activities,they present a huge potential for the development of various drugs with potential health and ecological benefits.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
Two new cembranoids, namely, sinumerolides A and B （1 and 2）, one new steroid, 7fl-hydroxygorgosterol （7）, along with four known cembranoid derivatives （3-6）, four known steroids （8-11）, and four known african...Two new cembranoids, namely, sinumerolides A and B （1 and 2）, one new steroid, 7fl-hydroxygorgosterol （7）, along with four known cembranoid derivatives （3-6）, four known steroids （8-11）, and four known africane ses- quiterpenoids （12-15）, were isolated and identified from the marine soil coral Sinularia numerosa that was col- lected from South China Sea waters. The structures of these metabolites were elucidated on the basis of extensive spectroscopic analysis and by comparison of their spectral data with those of literature reports. The isolated com- pounds were evaluated for the antimicrobial and cytotoxic activity.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
Main observation and conclusion Four new cembranoids,6-oxo-cembrene-A(1),lobocrassins G-H(2-3),and 14-epi-lobophytolide B(4),along with eight known re-lated compounds(5-12),were isolated from the South China Sea soft ...Main observation and conclusion Four new cembranoids,6-oxo-cembrene-A(1),lobocrassins G-H(2-3),and 14-epi-lobophytolide B(4),along with eight known re-lated compounds(5-12),were isolated from the South China Sea soft coral Lobophytum crassum.Their structures were established by extensive spectroscopic analysis and by comparison of the spectral data with those reported in the literatures.The absolute stere-ochemistry of 14-epi-lobophytolide B(4)was established by time-dependent density functional theory electronic circular dichroism(TDDFT-ECD)calculations,whereas that of three known metabolites(6,11 and 12)was also determined,for the first time,by using modified Mosher's method and/or X-ray diffraction analyses.In bioassay,the cembranoids 6,7 and 12 showed significant an-ti-tumoral activity against A549,HT-29,SNU-398 and Capan-1 tumor cell lines with IC_(50) values ranging from 1.5 to 7.4μmol/L.A pre-liminary structure-activity relationship was also discussed.展开更多
p-Tolylsulfenyl chloride adds regioselectively at the C(11)=C(12) bond of cembrene 1 to give 11-(R)-p-tolylthio-1-(S)-cembra-2E, 4Z, 7E, 12(20)-tetraene 2 following a rapid HCl elimination. Two new cembranoids, 1-(S)-...p-Tolylsulfenyl chloride adds regioselectively at the C(11)=C(12) bond of cembrene 1 to give 11-(R)-p-tolylthio-1-(S)-cembra-2E, 4Z, 7E, 12(20)-tetraene 2 following a rapid HCl elimination. Two new cembranoids, 1-(S)-cembra-2E, 4Z, 7E, 12(20)-tetraene 3 and 1-(S)-cembra-2E, 4Z, 7E, 11Z- tetraen-20-o1 4 are prepared from 2.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
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.
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.
基金This research was funded by the Indonesian Institute of Sciences(LIPI)through the DIPA 2021 Research Fund B-10405/IPH/HK.01.03/XI/2020。
文摘Soft corals are well-known as excellent sources of marine-derived natural products.Among them,members of the genera Sar-cophyton,Sinularia,and Lobophytum are especially attractive targets for marine natural product research.In this review,we reported the marine-derived natural products called cembranoids isolated from soft corals,including the genera Sarcophyton,Sinularia,and Lobophytum.Here,we reviewed 72 reports published between 2016 and 2020,comprising 360 compounds,of which 260 are new compounds and 100 are previously known compounds with newly recognized activities.The novelty of the organic molecules and their relevant biological activities,delivered by the year of publication,are presented.Among the genera presented in this report,Sarcophyton spp.produce the most cembranoid diterpenes;thus,they are considered as the most important soft corals for marine natural product research.Cembranoids display diverse biological activities,includ-ing anti-cancer,anti-bacterial,and anti-inflammatory.As cembranoids have been credited with a broad range of biological activities,they present a huge potential for the development of various drugs with potential health and ecological benefits.
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]
文摘Two new cembranoids, namely, sinumerolides A and B （1 and 2）, one new steroid, 7fl-hydroxygorgosterol （7）, along with four known cembranoid derivatives （3-6）, four known steroids （8-11）, and four known africane ses- quiterpenoids （12-15）, were isolated and identified from the marine soil coral Sinularia numerosa that was col- lected from South China Sea waters. The structures of these metabolites were elucidated on the basis of extensive spectroscopic analysis and by comparison of their spectral data with those of literature reports. The isolated com- pounds were evaluated for the antimicrobial and cytotoxic activity.
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the National Natural Science Foundation of China(Nos.81991521,81520108028,21672230)the National Key Research and Development Program of China(No.2018YFC0310903)+3 种基金the Drug Innovation Major Pro-ject(No.2018ZX09711-001-001-009)the SKLDR/SIMM Project(No.SIMM1903ZZ-04)the National 111 Project(No.D17012)X.-W.Li is also thankful for the Shanghai Rising-Star Program(No.20QA1411100)and SA-SIBS Scholarship Program.
文摘Main observation and conclusion Four new cembranoids,6-oxo-cembrene-A(1),lobocrassins G-H(2-3),and 14-epi-lobophytolide B(4),along with eight known re-lated compounds(5-12),were isolated from the South China Sea soft coral Lobophytum crassum.Their structures were established by extensive spectroscopic analysis and by comparison of the spectral data with those reported in the literatures.The absolute stere-ochemistry of 14-epi-lobophytolide B(4)was established by time-dependent density functional theory electronic circular dichroism(TDDFT-ECD)calculations,whereas that of three known metabolites(6,11 and 12)was also determined,for the first time,by using modified Mosher's method and/or X-ray diffraction analyses.In bioassay,the cembranoids 6,7 and 12 showed significant an-ti-tumoral activity against A549,HT-29,SNU-398 and Capan-1 tumor cell lines with IC_(50) values ranging from 1.5 to 7.4μmol/L.A pre-liminary structure-activity relationship was also discussed.
文摘p-Tolylsulfenyl chloride adds regioselectively at the C(11)=C(12) bond of cembrene 1 to give 11-(R)-p-tolylthio-1-(S)-cembra-2E, 4Z, 7E, 12(20)-tetraene 2 following a rapid HCl elimination. Two new cembranoids, 1-(S)-cembra-2E, 4Z, 7E, 12(20)-tetraene 3 and 1-(S)-cembra-2E, 4Z, 7E, 11Z- tetraen-20-o1 4 are prepared from 2.
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.
