A Rare Prostaglandin from the Soft Coral <i>Sarcophyton crassocaule</i> of the Indian Ocean

Anjaneyulu, A. S. R.; Murthy, Moturu V. R. Krishna; Gowri, P. Mangala; Venugopal, M.; Laatsch, Hartmut

doi:10.1021/np000148w

Cited by 12 publications

(9 citation statements)

References 7 publications

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“…In addition to the sesqui- and diterpenoids, several tetracyclic C-28 sterols possessing the ergostan ( C45 , C46 , C52 , C99 , and C103 ) and cholestan skeleton ( C103 , C108 , C112 , C115 , C118 ) were identified in coral extracts, all of which contained cyclopropane rings in their side chain backbone, a sterol pattern common in zooxanthellae . Interestingly, gorgostene-diol, a sterol that bears an unusual C-23 methyl group and a cyclopropane ring in its side chain ( C108 ) was identified along with its mono hydroxy ( C113 , Figure S3) and desmethyl derivative ( C118 ) in S. ehrenbergi samples but is likely to be derived from its harbored zooxanthellae. Gorgosterol is known to be produced by zooxanthellae, intracellular photosynthetic dinoflagellate symbionts living inside corals .…”

Section: Resultsmentioning

confidence: 99%

Soft Corals Biodiversity in the Egyptian Red Sea: A Comparative MS and NMR Metabolomics Approach of Wild and Aquarium Grown Species

et al. 2016

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Marine life has developed unique metabolic and physiologic capabilities and advanced symbiotic relationships to survive in the varied and complex marine ecosystems. Herein, metabolite composition of the soft coral genus Sarcophyton was profiled with respect to its species and different habitats along the coastal Egyptian Red Sea via (1)H NMR and ultra performance liquid chromatography-mass spectrometry (UPLC-MS) large-scale metabolomics analyses. The current study extends the application of comparative secondary metabolite profiling from plants to corals revealing for metabolite compositional differences among its species via a comparative MS and NMR approach. This was applied for the first time to investigate the metabolism of 16 Sarcophyton species in the context of their genetic diversity or growth habitat. Under optimized conditions, we were able to simultaneously identify 120 metabolites including 65 diterpenes, 8 sesquiterpenes, 18 sterols, and 15 oxylipids. Principal component analysis (PCA) and orthogonal projection to latent structures-discriminant analysis (OPLS) were used to define both similarities and differences among samples. For a compound based classification of coral species, UPLC-MS was found to be more effective than NMR. The main differentiations emanate from cembranoids and oxylipids. The specific metabolites that contribute to discrimination between soft corals of S. ehrenbergi from the three different growing habitats also belonged to cembrane type diterpenes, with aquarium S. ehrenbergi corals being less enriched in cembranoids compared to sea corals. PCA using either NMR or UPLC-MS data sets was found equally effective in predicting the species origin of unknown Sarcophyton. Cyclopropane containing sterols observed in abundance in corals may act as cellular membrane protectant against the action of coral toxins, that is, cembranoids.

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Section: Resultsmentioning

confidence: 99%

Soft Corals Biodiversity in the Egyptian Red Sea: A Comparative MS and NMR Metabolomics Approach of Wild and Aquarium Grown Species

et al. 2016

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“…374 An unusual 15-ketoprostaglandin 516 was isolated from Sarco-phyton crassocaule from the Indian Ocean. 375 Three additional prostaglandins, (5Z,15S )-15-acetylprostaglandin B 2 methyl ester 517, (5E,15S )-15-acetylprostaglandin B 2 methyl ester 518 and (5Z,13Z )-9-oxoprosta-5,10,13-trienoic acid methyl ester 519, were obtained as minor metabolites of Plexaura nina from the Bahamas. 376 The scleractinian coral Montipora sp.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

2001

Nat. Prod. Rep.

398

128

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This review covers the marine natural products literature for the year 2000 and is organized phylogenetically, with sections on marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, coelenterates, bryozoans, molluscs, tunicates. echinoderms and miscellaneous marine organisms. There is an emphasis on new structures, stressing their biological activities, source organisms and countries of origin, and also syntheses that confirm the structures of known compounds. The review contains 869 structures and 592 references, of which 434 appeared between January and December 2000.

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“…Bladder female transitional cancer (BFTC) cells have been widely used in biomedical and urological studies of bladder tumors [4,19,20]. In previous studies a series of novel secondary metabolites, including cembranes [21,22,23,24,25,26,27,28,29,30,31,32,33], steroids [22,28,30], hippurins [31], prostaglandins [32] and others [33] have been isolated from the Formosan soft coral Sarcophyton crassocaule . Some of these have been found to possess several kinds of biological activities, such as cytotoxic [22,24,25,27,28] and anti-inflammatory activity [27,28].…”

Section: Introductionmentioning

confidence: 99%

An Investigation into the Cytotoxic Effects of 13-Acetoxysarcocrassolide from the Soft Coral Sarcophyton crassocaule on Bladder Cancer Cells

Su¹,

Lin

et al. 2011

Marine Drugs

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Active compounds from natural products have been widely studied. The anti-tumor effects of 13-acetoxysarcocrassolide isolated from Formosan soft coral Sarcophyton crassocaule on bladder cancer cells were examined in this study. An MTT assay showed that 13-acetoxysarcocrassolide was cytotoxic to bladder female transitional cancer (BFTC) cells. We determined that the BFTC cells underwent cell death through apoptosis by flow cytometry. Due to the highly-migratory nature of the BFTC cells, the ability of 13-acetoxysarcocrassolide to stop their migration was assessed by a wound healing assay. To determine which proteins were affected in the BFTC cells upon treatment, a comparative proteomic analysis was performed. By LC-MS/MS analysis, we identified that 19 proteins were up-regulated and eight were down-regulated. Seven of the proteins were confirmed by western blotting analysis. This study reveals clues to the potential mechanism of the cytotoxic effects of 13-acetoxysarcocrassolide on BFTC cells. Moreover, it suggests that PPT1 and hnRNP F could be new biomarkers for bladder cancer. The results of this study are also helpful for the diagnosis, progression monitoring and therapeutic strategies of transitional cell tumors.

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A Rare Prostaglandin from the Soft Coral Sarcophyton crassocaule of the Indian Ocean

Cited by 12 publications

References 7 publications

Soft Corals Biodiversity in the Egyptian Red Sea: A Comparative MS and NMR Metabolomics Approach of Wild and Aquarium Grown Species

Soft Corals Biodiversity in the Egyptian Red Sea: A Comparative MS and NMR Metabolomics Approach of Wild and Aquarium Grown Species

Marine natural products

An Investigation into the Cytotoxic Effects of 13-Acetoxysarcocrassolide from the Soft Coral Sarcophyton crassocaule on Bladder Cancer Cells

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