New halogenated diterpenes from the red alga Laurencia perforata

González, Antonio G.; Cicció, José F.; Rivera, A. Patricio; Martı́n, Julio D.

doi:10.1021/jo00208a021

Cited by 23 publications

(14 citation statements)

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“…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]. Paniculatol (559) and the related metabolites 560 and 561 possess a tetrahydropyran ring [106,500], while metabolites 562 and 563, isolated from Laurencia obtusa collected from Mitikas Bay in the Ionian Sea, contain oxepane and oxocane moieties, respectively [501].…”

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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“…Isopimarane diterpenes lacking the CH 3 -10 rarely occur in fungi, and this is the first report of aromatic norisopimarane diterpenes from natural sources. It is interesting that some marine algae can produce isopimaranes, 18 which might be further processed by their endophytic fungi with these cryptic pathways.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

Aspewentins A–C, Norditerpenes from a Cryptic Pathway in an Algicolous Strain of Aspergillus wentii

et al. 2014

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Through addition of suberoylanilide hydroxamic acid, two new aromatic norditerpenes, aspewentins A (1) and B (2), along with an oxygenated derivative, aspewentin C (3), were obtained from the culture of an Aspergillus wentii strain (na-3) isolated from the tissue of the brown alga Sargassum fusiforme. The structures and absolute configurations were unambiguously elucidated by spectroscopic analyses and quantum chemical calculations. Aspewentins A-C were produced before sporulation and exhibited potent bioactivities against some marine-derived organisms.

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“…The two bromine atoms present in the molecular formula were located at C-3 (d 69.6) and C-15 (d 61.8), because the chemical shift of these carbon atoms were about 15 ppm lower than those observed in pimaranes oxygenated at these positions, 9 while are close to those observed in a 3,15-dibromoisopimarane from Laurencia perforata. 13 Finally, the sulfate group was located at the remaining position 16, thus completing the planar structure of compound 1.…”

Section: Isolation and Structural Elucidationmentioning

confidence: 97%