The C-13 configuration of the bromine-containing diterpene isoaplysin-20. Synthesis of debromoisoaplysin-20 and C-13 epimer

Imamura, Paulo M.; Rúveda, Edmundo A.

doi:10.1021/jo01291a028

Cited by 29 publications

(26 citation statements)

References 3 publications

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“…Aplysin-20 (546) and isoaplysin-20 (557) were the first members of this group to be isolated from the sea hare Aplysia kurodai in 1971 by Yamamura and Hirata [485,486] and in 1977 by Yamamura and Terada [496], respectively. The initially proposed structures were revised after the total syntheses of the natural products [488,[497][498][499]. The rearranged labdane 558 was obtained from Laurencia perforata, along with the pimarane derivatives 567 and 568 [495].…”

Section: Labdanes Pimaranes and Related Diterpenesmentioning

confidence: 99%

The Laurencia Paradox: An Endless Source of Chemodiversity

Harizani

Iοannou

Roussis

2016

Progress in the Chemistry of Organic Natural Products

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Nature, the most prolific source of biological and chemical diversity, has provided mankind with treatments for health problems since ancient times and continues to be the most promising reservoir of bioactive chemicals for the development of modern drugs. In addition to the terrestrial organisms that still remain a promising source of new bioactive metabolites, the marine environment, covering approximately 70% of the Earth's surface and containing a largely unexplored biodiversity, offers an enormous resource for the discovery of novel compounds. According to the MarinLit database, more than 27,000 metabolites from marine macro- and microorganisms have been isolated to date providing material and key structures for the development of new products in the pharmaceutical, food, cosmeceutical, chemical, and agrochemical sectors. Algae, which thrive in the euphotic zone, were among the first marine organisms that were investigated as sources of food, nutritional supplements, soil fertilizers, and bioactive metabolites.Red algae of the genus Laurencia are accepted unanimously as one of the richest sources of new secondary metabolites. Their cosmopolitan distribution, along with the chemical variation influenced to a significant degree by environmental and genetic factors, have resulted in an endless parade of metabolites, often featuring multiple halogenation sites.The present contribution, covering the literature until August 2015, offers a comprehensive view of the chemical wealth and the taxonomic problems currently impeding chemical and biological investigations of the genus Laurencia. Since mollusks feeding on Laurencia are, in many cases, bioaccumulating, and utilize algal metabolites as chemical weaponry against natural enemies, metabolites of postulated dietary origin of sea hares that feed on Laurencia species are also included in the present review. Altogether, 1047 secondary metabolites, often featuring new carbocyclic skeletons, have been included.The chapter addresses: (1) the "Laurencia complex", the botanical description and the growth and population dynamics of the genus, as well as its chemical diversity and ecological relations; (2) the secondary metabolites, which are organized according to their chemical structures and are classified into sesquiterpenes, diterpenes, triterpenes, acetogenins, indoles, aromatic compounds, steroids, and miscellaneous compounds, as well as their sources of isolation which are depicted in tabulated form, and (3) the biological activity organized according to the biological target and the ecological functions of Laurencia metabolites.

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Section: Labdanes Pimaranes and Related Diterpenesmentioning

confidence: 99%

The Laurencia Paradox: An Endless Source of Chemodiversity

Harizani

Iοannou

Roussis

2016

Progress in the Chemistry of Organic Natural Products

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“…It was observed that C,, and C , , A,(") and A1' (13) have the same energy, and A13 (14) is the least stable. For the C,1-C,4 homologs, A,(") is more stable than and Al3(l4) is the most stable.…”

Section: Discussionmentioning

confidence: 99%

Mass spectrometric characteristics of two novel series of ring‐C monounsaturated tricyclic terpenes found in Tasmanian tasmanite

1995

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Electron impact and methane chemical ionization mass spectra were measured for two homologous series of monounsaturated tricyclic terpenes, A9'' ') and A13(14). The double bond position was inferred by interpretation of their mass spectra, comparisons with the known saturated and ring-C monoaromatic series, published mass spectrometric data on other terpenoids and MM2 calculations. The distributions of and 6,'' "-monounsaturated tricyclic terpene isomers were shown by theory and from experimental data to be dependent on the chain length at position 14. These two series coexist in the same geological sample. A9(' ')-Monounsaturated tricyclic terpenes can be derived from the compounds by isomerization of the double bond. The A9(' "-monounsaturated tricyclic terpene series extends from C,, to C,, and the A"(14) series from C,, to C.,,. The diastereomers >C2,, for both series could be resolved by gas chromatography.

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“…(1) those belonging to the α-chamigrene series possessing a trisubstituted double bond between C-7 and C-8 (1-26); (2) those belonging to the β-chamigrene series not designated (246) 5,7-cycloeudesmane (446) aristolane (450)(451)(452)(453)(454)(455)(456)(457)(458)(459)(460)(461)(462)(463) triquinane (490)(491)(492) cedrane (494) 3,6-cyclo-precapnellane (493) aromadendrane (496)(497)(498) africanane (495) calenzanane (500)(501) cyclococane (499) not designated (502) rhodolaurane (508)(509)(510)(511) omphalane (503)(504) not designated (512) gomerane (505)(506)(507) 6,8-cycloeudesmane (447) cyclolaurane (225)(226)(227)(228)(229)(230)…”

Section: Chamigranes and Related Sesquiterpenesmentioning

confidence: 99%