New Isocyano and Isothiocyanato Terpene Metabolites from the Tropical Marine Sponge Acanthella cavernosa

Clark, Richard J.; Stapleton, Bronwin; Garson, Mary J.

doi:10.1016/s0040-4020(00)00226-x

Cited by 32 publications

(38 citation statements)

References 12 publications

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“…4-Isocyanatoeudesm-11-ene ( Eu19 ) and 4-formamidoeudesm-11-ene ( Eu21 ) have been isolated from the Caribbean sponge Axinyssa ambrosia [ 26 ]. The appropriate 4-isothiocyanatoeudesm-11-ene ( Eu20 ) was found in the sponge Acanthella klethra [ 30 ] and later also in an unidentified sponge of the genus Acanthella , the nudibranch Ca dlina luteomarginata [ 23 ], the sponge Acanthella cavernosa [ 31 , 32 ] and the sponge Axinyssa Isabela [ 33 ]. Similar to isothiocyanate Eu17 , 4-isothiocyanatoeudesm-11-ene ( Eu20 ) displayed a moderate antimalarial activity against Plasmodium falciparum (chloroquine-sensitive strain D6: IC 50 = 4000 ng/mL, chloroquine-resistant strain W2: IC 50 = 550 ng/mL) and no cytotoxic activity against KB-3 cells (IC 50 > 20 µg/mL) [ 29 ].…”

Section: Marine Isonitriles and Related Compoundsmentioning

confidence: 99%

“…This isonitrile also displayed potent antifouling activity against larvae of the acorn barnacle Balanus amphitrite (IC 50 = 0.14 µg/mL) [ 42 ]. Four years later, the corresponding 10-isothiocyanato-4-cadinene ( Ca14 ) was isolated from the tropical marine sponge Acanthella cavernosa [ 31 ]. Its absolute configuration was elucidated by enantioselective synthesis of both optical antipodes [ 48 ].…”

Section: Marine Isonitriles and Related Compoundsmentioning

confidence: 99%

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Marine Isonitriles and Their Related Compounds

2016

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Marine isonitriles represent the largest group of natural products carrying the remarkable isocyanide moiety. Together with marine isothiocyanates and formamides, which originate from the same biosynthetic pathways, they offer diverse biological activities and in spite of their exotic nature they may constitute potential lead structures for pharmaceutical development. Among other biological activities, several marine isonitriles show antimalarial, antitubercular, antifouling and antiplasmodial effects. In contrast to terrestrial isonitriles, which are mostly derived from α-amino acids, the vast majority of marine representatives are of terpenoid origin. An overview of all known marine isonitriles and their congeners will be given and their biological and chemical aspects will be discussed.

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Section: Marine Isonitriles and Related Compoundsmentioning

confidence: 99%

Section: Marine Isonitriles and Related Compoundsmentioning

confidence: 99%

Marine Isonitriles and Their Related Compounds

2016

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“…The kalihinanes ( 3 – 6 are representative) are a subgroup of these isocyanoterpenes isolated primarily from sponges of the genus Acanthella and characterized by cis - or trans -decalin cores bearing pendant tetrahydropyrans or tetrahydrofurans and a variable set of isonitrile, isocyanate, isothiocyanate, formamide, hydroxyl, and chloride substituents. 2 …”

mentioning

confidence: 99%

“…There is a wealth of structural diversity in the kalihinane group, 2 and a synthesis that could address multiple naturally occurring kalihinanes as well as synthetic analogues would permit a thorough evaluation of structure–activity relationships. The relative scarcity of material from natural sources 2 and the length of the reported chemical approaches to the kalihinanes ( 3 in ca. 37 steps longest linear sequence (LLS); 5a and 6 in ca.…”

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confidence: 99%

Synthesis and Potent Antimalarial Activity of Kalihinol B

et al. 2015

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Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kalihinanes with a 12-step enantioselective synthesis of kalihinol B, the tetrahydrofuran isomer of kalihinol A (a tetrahydropyran). Kalihinol B shows similarly high potency against chloroquine-resistant Plasmodium falciparum.

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“…[29][30][31][32][33][34][35][36][37][38] Haplosclerida) collected at Indented Head Reef (Port Phillip Bay). 73 D and E. 121 A new purine derivative, microxine (142), was isolated from marine sponge Microxina sp.…”

Section: Sesquiterpenesmentioning

confidence: 99%

Marine biodiversity: exploring bioactive chemical space

Prasad¹

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This thesis is focused on exploration of Australian and Antarctica marine plants and invertebrates for the discovery of new and unusual natural products. A marine extract library (Capon) of over 2500 Australian and Antarctica marine plants and invertebrates was the platform for this research.High-throughput chemical profiling was executed by UHPLC-DAD to rapidly de-replicate, prioritise and fast track the chemical analysis of 2626 marine extracts. The acquired data was compiled as a chromatography-based library, establishing one central platform equipped with chromatography knowledge of the entire marine collection. Concurrently, assessing the biological potentials of the extract library was carried out in order to rapidly prioritise extracts. Employed biological assays included Bacillus Calmette-Guerin (BCG) screening and α 5 β 3 γ 2 -GABA A modulatory screening. Bioassay-guided fractionation was employed to guide the discovery of bioactive natural products. The prioritised hits were subjected to extraction, isolation and purification employing various techniques such as trituration, solvent-solvent partitioning, SPE fractionation, size exclusion chromatography, and analytical/semi-preparative and preparative HPLCs. Spectroscopic methods (UV-Vis, [α]

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New Isocyano and Isothiocyanato Terpene Metabolites from the Tropical Marine Sponge Acanthella cavernosa

Cited by 32 publications

References 12 publications

Marine Isonitriles and Their Related Compounds

Marine Isonitriles and Their Related Compounds

Synthesis and Potent Antimalarial Activity of Kalihinol B

Marine biodiversity: exploring bioactive chemical space

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