Phorbasin B and C:  Novel Diterpenes from a Southern Australian Marine Sponge, <i>Phorbas</i> Species

McNally, Michelle; Capon, Robert J.

doi:10.1021/np0005614

Cited by 44 publications

(36 citation statements)

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“…An aliquot (1.73 g) of the fraction eluted with 10% MeOH(aq) was dried and separated by reversed-phase HPLC (YMC-ODS-A column, 20% MeOH(aq)) to afford, in the order of elution, compounds 13, 11,6,3,8,5,4,15,9,7,12,14,2, and 1 as white solids. An aliquot (1.75 g) of the fraction eluted with 100% MeOH was dried and separated by reversed-phase HPLC (YMC-ODS-A column, 15% MeOH(aq)) to afford, in the order of elution, compounds 4, 12, 2, 1, 16, 10, and 17 as white solids.…”

Section: Methodsmentioning

confidence: 99%

“…Ten new polyoxygenated diterpenes (7)(8)(9)(10)(11)(12)(13)(14)(15)(16) along with six known gagunin compounds (1)(2)(3)(4)(5)(6) were isolated from the sponge Phorbas sp. collected in the Korean Sea.…”

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confidence: 99%

“…[3][4][5][6] Other chemical species isolated from Phorbas include the phorbasins, which are essentially diterpenoids with skeletal rearrangements, the phorbasides, which are 14-membered lactone metabolites, and the phorbasterones and amaranzole A, which are steroids bearing unique functional groups. [7][8][9][10][11] Sponges of the genus Phorbas are common in the waters off the southwestern coast of Korea. Our previous studies of these animals yielded gagunins, cytotoxic diterpenoids with highly oxygenated functionalities on a 10,13-epi-homoverrucosane skeleton.…”

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Polyoxygenated Diterpenes from the Sponge Phorbas sp.

et al. 2008

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Ten new polyoxygenated diterpenes (7-16) along with six known gagunin compounds (1-6) were isolated from the sponge Phorbas sp. collected in the Korean Sea. On the basis of a combination of NMR and mass spectroscopic analyses, the molecular structures of these diterpenes, designated as gagunins H-Q, were determined to be penta- or hexa-oxygenated diterpenes of the 10,13-bis-epi-homoverrucosane class. A new diterpene acid (17) of a bisabolane-related skeletal class was also isolated and structurally defined by the spectroscopic analyses. These compounds exhibited moderate to significant cytotoxicity against the K-562 cell line as well as weak inhibitory activity against isocitrate lyase (ICL).

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Section: Methodsmentioning

confidence: 99%

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Polyoxygenated Diterpenes from the Sponge Phorbas sp.

et al. 2008

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“…A great variety of original bioactive metabolites had been already reported from species of the genus Phorbas including alkaloids (Rudi et al . ), macrolides (Searle and Molinski ), terpenoids (McNally and Capon ; Rho et al . ; Jang et al .…”

Section: Introductionmentioning

confidence: 99%

Diversity and biological activities of the bacterial community associated with the marine sponge Phorbas tenacior (Porifera, Demospongiae)

Dupont

Carré-Mlouka

Descarrega

et al. 2013

Lett Appl Microbiol

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Significance and Impact of the Study: This study presents the first report on the diversity of the cultivable bacteria associated with the marine sponge Phorbas tenacior, frequently found in the Mediterranean Sea. Evaluation of the antiplasmodial, antimicrobial and antioxidant activities of the isolates has been investigated and allowed to select bacterial strains, confirming the importance of Proteobacteria and Actinobacteria as sources of bioactive compounds.Keywords antimicrobial activity, antioxidant activity, antiplasmodial activity, associated bacteria, Phorbas tenacior, phylogenetic diversity, RAPD, sponge. AbstractThe diversity of the cultivable microbiota of the marine sponge Phorbas tenacior frequently found in the Mediterranean Sea was investigated, and its potential as a source of antimicrobial, antioxidant and antiplasmodial compounds was evaluated. The cultivable bacterial community was studied by isolation, cultivation and 16S rRNA gene sequencing. Twenty-three bacterial strains were isolated and identified in the Proteobacteria (a or c classes) and Actinobacteria phyla. Furthermore, three different bacterial morphotypes localized extracellularly within the sponge tissues were revealed by microscopic observations. Bacterial strains were assigned to seven different genera, namely Vibrio, Photobacterium, Shewanella, Pseudomonas, Ruegeria, Pseudovibrio and Citricoccus. The strains affiliated to the same genus were differentiated according to their genetic dissimilarities using random amplified polymorphic DNA (RAPD) analyses. Eleven bacterial strains were selected for evaluation of their bioactivities. Three isolates Pseudovibrio P1Ma4, Vibrio P1MaNal1 and Citricoccus P1S7 revealed antimicrobial activity; Citricoccus P1S7 and Vibrio P1MaNal1 isolates also exhibited antiplasmodial activity, while two Vibrio isolates P1Ma8 and P1Ma5 displayed antioxidant activity. These data confirmed the importance of Proteobacteria and Actinobacteria associated with marine sponges as a reservoir of bioactive compounds. IntroductionMarine sponges constitute a significant element in benthic communities in the world's oceans, in terms of both biomass and potential to participate in ecological processes. They are also recognized as a rich source of biologically active compounds (Blunt et al. 2012). Currently, five marine natural products or semisynthetic analogues isolated from sponges have been approved as therapeutics.Thirteen molecules are in clinical trials for various applications, mainly as anticancer agents, and one hundred are undergoing preclinical evaluation (Mayer et al. 2010). In the past decade, many studies have focused on the complex ecosystem sponge-microbial communities due to the association of sponges with dense and diverse microbial communities of the three domains of life (Bacteria, Archaea and Eukarya) (Taylor et al. 2007). The spongeassociated micro-organisms have revealed high densities, Letters in Applied Microbiology 58, 42--52

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“…A parallel investigation of another Phorbas sp collected during the same scientific cruise yielded two new monocyclic diterpenes identified as phorbasin B (34) and C (35). [18] Once again, complete relative stereostructures were secured by spectroscopic analysis. Stability issues precluded experimental determinations of absolute stereochemistry for phorbasins AϪC.…”

Section: Diterpenesmentioning

confidence: 97%

Marine Bioprospecting − Trawling for Treasure and Pleasure

Capon

2001

Eur. J. Org. Chem.

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This Microreview seeks to highlight the molecular diversity present in marine organisms, and illustrate by example some of the challenges encountered in exploring this resource. Marine natural products exhibit an impressive array of structural motifs, many of which are derived from biosynthetic pathways that are uniquely marine. Most importantly, some marine metabolites possess noteworthy biological activities, activities that have potential application outside marine ecosystems, such as antibiotics, antiparasitics, anticancer agents etc... The isolation, spectroscopic characterisation and assignment of stereostructures to these unusual metabolites is both challenging and rewarding. Examples featured in this Microreview follow a common theme in that they are all recent accounts of the isolation of natural products from Australian marine sponges, carried out in the laboratories of the author. In addition to presenting brief comments on specific structure elucidation strategies, an effort is made to emphasize techniques for solving stereochemical issues, as well as to speculate on the biosynthetic origins of some of these exotic marine natural products.

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Phorbasin B and C: Novel Diterpenes from a Southern Australian Marine Sponge, Phorbas Species

Abstract: A southern Australian Phorbas sp. has yielded the novel diterpenes phorbasin B (2) and phorbasin C (3). Phorbasins B and C possess a hitherto unknown carbon skeleton, and their structures were assigned on the basis of detailed spectroscopic analyses.

Cited by 44 publications

References 10 publications

Polyoxygenated Diterpenes from the Sponge Phorbas sp.

Polyoxygenated Diterpenes from the Sponge Phorbas sp.

Diversity and biological activities of the bacterial community associated with the marine sponge Phorbas tenacior (Porifera, Demospongiae)

Marine Bioprospecting − Trawling for Treasure and Pleasure

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