The isolation and structure determination of chilenone A, a putative dimer of 2-methyl-3(2H)-furanone from the marine alga

Martín, Aurelio San; Rovirosa, Juana; Muñoz, Orlando; Chen, Marie H.M.; Guneratne, Ranil D.; Clardy, Jon

doi:10.1016/s0040-4039(00)88262-3

Cited by 30 publications

(12 citation statements)

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“…Chilenones A (1011) and B (1012), a dimer and a trimer of 2-methyl-3(2H )-furanone, and the tetracyclic polyketal 1013 were isolated as naturally occurring racemates from Laurencia chilensis and their structures were elucidated on the basis of X-ray crystallographic analysis [817][818][819]. Spiro-bis-pinnaketal (1014) was isolated as a natural product from Laurencia pinnatifida [821], but was later proven to be an artifact derived from laurencione (1015), which was subsequently obtained as a labile mixture of tautomers from an extract of Laurencia spectabilis [822].…”

Section: Miscellaneous Metabolitesmentioning

confidence: 99%

“…The acetogenins panacene (746) [78], brasilenyne (891), (Z)-dihydrorhodophytin (810) and (Z)-isodihydrorhodophytin (817) [221], as well as the sesquiterpenes brasudol (432) and isobrasudol (433) [419] exhibited variable levels of inhibition of fish feeding activity. Pacifigorgiol (485), a highly rearranged sesquiterpene, exhibited toxicity towards the reef-dwelling fish Eupomacentrus leucostictus [900].…”

Section: Antifeedant Activity and Toxicity To Marine Organismsmentioning

confidence: 99%

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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: Miscellaneous Metabolitesmentioning

confidence: 99%

Section: Antifeedant Activity and Toxicity To Marine Organismsmentioning

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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“…The antimicrobial metabolites of the alga P. cruciferum, from New Zealand, were shown to be the polyhalogenated monoterpene (321) and a bisnormonoterpenoid (322).230723 The structure (321) was determined by X-ray analysis,231 while that of the alcohol (322) was elucidated from spectral data. The Australian alga P. angustum contains two linear monoterpenes (323) and (324).…”

Section: ) Plocumium Oregonum Also Contained Two Known Metabolites Of...mentioning

confidence: 99%

Marine natural products: metabolites of marine algae and herbivorous marine molluscs

Faulkner¹

1984

Nat. Prod. Rep.

359

138

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“…Laurencione existing as a labile mixture of tautomers 166 and 167 was identified from Oregonian L. spectabilis by spectral analysis and chemical synthesis (Bernart et al 1992;de Kimpe et al 1995de Kimpe et al , 1996. Three pairs of enantiomers 168/ 169, 170/171, and 172/173 were identified from Chilean L. chilensis, and their structures were determined with the aid of X-ray crystallographic techniques (San-Martin et al 1983Bittner et al 1987). These miscellaneous nonhalogenated constituents also exhibited high molecular diversity, which accounted for more than one tenth of the Laurencia-derived nonhalogenated organic molecules.…”

Section: Miscellaneous Nonhalogenated Productsmentioning

confidence: 99%

Nonhalogenated organic molecules from Laurencia algae

Wang

2013

Phytochem Rev

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The marine red algae of the genus Laurencia have produced more 700 secondary metabolites and exhibited high molecular diversity and intriguing bioactivity. Since the halogenated structures have been comprehensively reviewed previously, this review, covering up to the end of 2012, mainly focuses on the source, structure elucidation, and bioactivity of nonhalogenated organic molecules from Laurencia spp. as well as the relationship between nonhalogenated and halogenated products. Overall, 173 new or new naturally occurring compounds with 58 skeletons, mainly including sesquiterpenes, diterpenes, triterpenes, and C 15 -acetogenins, are described.

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The isolation and structure determination of chilenone A, a putative dimer of 2-methyl-3(2H)-furanone from the marine alga

Cited by 30 publications

References 4 publications

The Laurencia Paradox: An Endless Source of Chemodiversity

The Laurencia Paradox: An Endless Source of Chemodiversity

Marine natural products: metabolites of marine algae and herbivorous marine molluscs

Nonhalogenated organic molecules from Laurencia algae

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