Antibacterial effect of the red sea soft coral Sarcophyton trocheliophorum

The marine soft corals Sarcophyton trocheliophorum crude extracts possessed antimicrobial activity towards pathogenic bacterial strains, i.e. Bacillus cereus, Salmonella typhi, Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa. Bioassay-guided fractionation indicated that the antimicrobial effect was due to the presence of terpenoid bioactive derivatives. Further biological assays of the n-hexane fractions were carried out using turbidity assay, inhibition zone assay and minimum inhibitory concentration for investigating the growth-inhibition effect towards the Gram-positive and Gram-negative bacteria. The fractions were screened and the structure of the isolated compound was justified by interpretation of the spectroscopic data, mainly mass spectrometry (GC-MS). The structure was assigned as (5S)-3-[(3E,5S)-5-hydroxy-3-hepten-6-yn-1-yl]-5-methyl-2(5H)-furanone and was effective at concentrations as low as 0.20 mg/mL. The above findings, in the course of our ongoing research on marine products, may implicate that the profound anti-microbial activity of the S. trocheliophorum soft corals, inhabiting the red sea reefs, is attributed to the presence of growth-inhibiting secondary metabolites mainly terpenoids.     

Yalongenes A and B,Two New Cembranoids with Cytoprotective Effects from the Hainan Soft Coral Sarcophyton trocheliophorum Marenzeller

Two new cembranoids, yalongenes A ( 1 ) and B ( 2 ), were isolated from the South China Sea soft coral Sarcophyton trocheliophorum Marenzeller . Their structures were elucidated by detailed spectroscopic analysis (IR, MS, and NMR) and by comparison with a related model compound. Yalongenes 1 and 2 were evaluated for their cytoprotective effects on SH‐SY5Y cell injury induced by H₂O₂ in vitro, and the result showed that only compound 1 had a significant cytoprotective activity at the concentration of 1 μM .     

Studies on the Formosan Soft Corals I-Cytotoxic Cembrane Diterpenes from Sarcophyton Trocheliophorum

Two cytotoxic cembranoid diterpenes, (+)-isosarcophytoxide (1) and ( + )-isosarcophine (2), were isolated from the soft coral Sarcophyton trocheliophorum by cytotoxicity-guided fractionation. These two compounds demonstrated potent cytotoxicity against P-388 and HL-60 cells.     

Sarcoconvolutums F and G: Polyoxygenated Cembrane-Type Diterpenoids from Sarcophyton convolutum,a Red Sea Soft Coral

Natural products and chemical analogues are widely used in drug discovery, notably in cancer and infectious disease pharmacotherapy. Sarcophyton convolutum (Alcyoniidae) a Red Sea–derived soft coral has been shown to be a rich source of macrocyclic diterpenes and cyclized derivatives. Two previously undescribed polyoxygenated cembrane-type diterpenoids, sarcoconvolutums F (1) and G (2), as well as four identified analogues (3–6) together with a furan derivate (7) were isolated from a solvent extract. Compounds were identified by spectroscopic techniques, including NMR, HREIMS, and CD, together with close spectral comparisons of previously published data. Sarcoconvolutum F (1) contains a rare 1-peroxid-15-hydroxy-10-ene functionality. Isolated metabolites (1–7) were screened against lung adenocarcinoma (A549), cervical cancer (HeLa) and oral cavity carcinoma (HSC-2) lines. Compound 4 exhibited an IC₅₀ 56 µM and 55 µM against A549 and HSC-2 cells, respectively.     

Crystal structure and configuration revision of 9-hydroxy-7,8-dehydro-sarcotrocheliol and sarcotrocheliol

Herein, we report the isolation and stereo-structure of rare pyrane-based cembranoid diterpenes, 9-hydroxy-7,8-dehydro-sarcotrocheliol (1) and sarcotrocheliol (2), from Sarcophyton trocheliophorum collected from Red Sea. Absolute configurations of both compounds were revised based on single crystal X-ray analyses.     

A review of steroids from Sarcophyton species

This review reports the structural diversity of steroids from Sarcophyton species based on literature from the beginning of marine steroid research until now. There are 65 compounds studied from eight species. Most of them are polyhydroxy-type steroids of C-27–C-31 carbon skeleton. Their biological activities are highly diverse ranging from cytotoxic, antibacterial, antifungal, antiviral, anti-inflammatory, antidiabetic to antiosteoporosis properties.     

A Novel Sarsolenane Diterpene as a PTP1B Inhibitor from Hainan Soft Coral Sarcophyton trocheliophorum Marenzeller

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.     

Structural,stereochemical, and bioactive studies of cembranoids from Chinese soft coral Sarcophyton trocheliophorum

A series of highly oxidative new cembranoids with diverse structural features such as a dienoate moiety (sarcophytonolides S – U, 1–3) or an α,β-unsaturated ε-lactone (sartrolides H – J, 4–6) were obtained from Hainan soft coral Sarcophyton trocheliophorum, along with known related analogues 7–13. It is an extremely challenging work to determine the absolute configurations of these metabolites. For compounds 1, 3 and 4, solution TDDFT calculation of ECD and specific rotation were applied in combination with conformational analysis and NMR data to determine their relative and absolute configurations, leading to the revision of relative configuration of 14. The absolute configurations of compounds 8–10 were determined by the solid-state TDDFT-ECD approach, and that of 8 was further confirmed by single-crystal X-ray diffraction experiment with Cu Kα radiation. In the bioassays, compound 8 exhibited not only moderate protein tyrosine phosphatase 1B (PTP1B) inhibitory activity (IC₅₀?=?15.4?μM) but also moderate antibacterial activity against Staphylococcus aureus Newman strain (MIC₅₀?=?250?μM).     

New derivatives of (?)-neocembrene from the soft coral Sarcophyton trocheliophorum

A hexane extract of the soft coralSarcophyton trocheliophorum has yielded two new diterpenoids for which the structures of 13S-hydroxy-(–)-neocembrene and 13S-hydroxy-11,12-epoxy-(–)-neocembrene have been established.Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR. Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Branch, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 535–540, July–August, 1988.     

New cembranoid diterpenes from the Vietnamese soft coral Sarcophyton mililatensis stimulate osteoblastic differentiation in MC3T3-E1 cells

Chemical investigation of the Vietnamese soft coral Sarcophyton mililatensis resulted in the isolation of four new cembranoid diterpenes, namely (-)-7beta-hydroxy-8alpha-methoxydeepoxysarcophytoxide (1), (+)-7beta,8beta-dihydroxydeepoxysarcophytoxide (2), (-)-17-hydroxysarcophytonin A (3) and sarcophytol V (4), along with two known compounds, (+)-sarcophine (5) and sarcophytoxide (6). The NMR spectral data of the new compounds were completely assigned by using a combination of 2D NMR experiments including (1)H-(1)H COSY, HSQC, HMBC, and ROESY. To investigate the bioactivities of compounds, which act on bone metabolism, we studied the effects of compounds on the function of osteoblastic MC3T3-E1 cells. Compound 1 caused a significant elevation of alkaline phosphatase activity, collagen content, and nodules mineralization compared to those of the control (p<0.05). These results suggest that newly isolated compound 1 has a direct stimulatory effect on bone formation in vitro and may contribute to the prevention for osteoporosis.     

Sardisterol,A New Polyhydroxylated Sterol from the Soft Coral Sarcophyton digitatum Moser

A new polyhydroxylated sterol, named sardisterol, was isolated from the soft coral Sarcophyton digitatum Moser. Its structure was determined as (22R, 24ξ)‐methylcholest‐5‐en‐3β, 22, 25, 28‐tetraol‐3‐acetate on the basis of spectroscopic methods.     

Further New Cembrane Diterpenes from the Hainan Soft Coral Sarcophyton latum

Two new cembranoid diterpenes, diepoxysarcophytonene ( 1 ) and sarconphytonol ( 2 ), were isolated from the Hainan soft coral Sarcophyton latum. Their structures including relative stereochemistry were established by 1D and 2D NMR spectroscopic techniques. Compound 1 showed weak inhibitory activity against COX‐2 in vitro at the concentration of 10^?5 µmol·L^?1 with the inhibitory rate of 55%.     

肉芝软珊瑚Sarcophyton crassocaule中新的多羟基甾醇的分离

报道了从三亚海域的一种肉芝软珊瑚Sarcophyton crassocaule Mosre中分离得到2个多羟基甾醇1和2. 通过波谱分析等方法测定了它们的化学结构, 化合物1为新化合物, 命名为Sarcrasterol. 化合物2为已知物[24ξ-methyl-colestane-3β,5β,6α,25-tetrol], 但其C24构型未确定, 通过X射线单晶衍射分析测定了其相对构型为24S.     

New cytotoxic isoprenoid derivatives from the Red Sea soft coral Sarcophyton glaucum

Chemical investigation of the soft coral Sarcophyton glaucum collected from the Red Sea led to isolation of 11 isoprenoidal metabolites (1–11). A new sesquiterpenoid, 6-oxo-germacra-4(15),8,11-triene (1), a new natural cembranoid, sarcophinediol, along with two known sesquiterpenoids (2 and 3) and seven known cembranoids (5–11) was obtained. The structures of the compounds were established based on their NMR, MS, IR and UV spectral data. All compounds were evaluated for their cytotoxicity employing three cancer cell lines (HepG2, MCF-7 and HCT116). Compounds 4 and 6 showed significant cytotoxicity towards HepG2 with IC₅₀ values of 18.8 ± 0.07 and 19.9 ± 0.02 μM; respectively. Compounds 5–7 exhibited potent cytotoxicity against MCF-7 cells with IC₅₀ values of 9.9 ± 0.03, 2.4 ± 0.04 and 3.2 ± 0.02 μM, respectively. Compounds 1, 4 and 5 showed significant activities towards HCT116 cells with IC₅₀ values of 29.4 ± 0.03, 19.4 ± 0.02 and 25.8 ± 0.03 μM, respectively.     

Further New Bis‐cembranoids from the Hainan Soft Coral Sarcophyton tortuosum

Two new bis‐cembranoids, ximaolides F ( 1 ) and G ( 2 ), were isolated from the Hainan soft coral Sarcophyton tortuosum. The structures and relative configurations of the two new compounds were elucidated by the combination of spectroscopic methods, chemical conversion of ximaolide F ( 1 ) into ximaolide G ( 2 ), and comparison with related model compounds.     

Novel Polyhydroxysteroids from the Formosan Soft Coral Sarcophyton Glaucum

Two novel polyhydroxysteroids, (24S)‐24‐methylcholestane‐3β,5α,6β,25ξ;,26‐pentol 26‐n‐decanoate ( 1 ), (24S)‐24‐methylcholestane‐3β,5α,6β,25ξ;,26‐pentol 25,26‐diacetate ( 2 ), and three known sterols ( 3‐5 ), have been isolated from a Formosan soft coral Sarcophyton glaucum. The molecular structures of these compounds were determined by spectral methods. The cytotoxicity of these compounds toward various cancer cell lines has also been determined.     

A Novel Diterpenoid from the Soft Coral Sarcophyton crassocaule

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 IC50 value of 0.1 μg/mL.     

软珊瑚Sarcophyton sp.中一个新的西松烷二萜内酯的分离及结构测定

肉芝软珊瑚 Sarcophyton富含二萜 ,从这类软珊瑚生物体中已经分离出许多含十四元环结构的西Scheme 1　 Sturcture of Sarcophydiol 1松烷二萜内酯 ,例如 Sarcophinone[1] ,iso-Sarcophinone[2 ] ,Sarcophine[3,4 ] ,Sartrochine[5] 和 iso-Sarcophine[6 ,7] .这些西松烷二萜内酯均有较强的细胞毒性 .在对采自南中国海的一种肉芝软珊瑚 Sar-cophyton sp.次生代谢产物的研究过程中 ,我们分离得到一个在生源上与 iso- Sarcophine有密切关系的新西松烷二萜内酯 Sarcophydiol 1 (结构见Scheme 1 ) .本文报道其分离方法及结构测定结果 .1　…     

Further New Cembranoid Diterpenes from the Hainan Soft Coral Sarcophyton latum

Four new cembranoid diterpenes, sarcophytonolides I–L ( 1 – 4 ), were isolated from the Hainan soft coral Sarcophyton latum. Their structures were established by detailed analysis of 1D and 2D NMR spectra and by comparison with related model compounds.