Sesquiterpenes from the Brazilian Red Alga Laurencia dendroidea J. Agardh

Machado, Fernanda Lacerda da Silva; Ventura, Thatiana Lopes Biá; Gestinari, Lísia Mônica de Souza; Cassano, Valéria; Resende, Jackson A. L. C.; Kaiser, Carlos R.; Lassounskaia, Elena; Muzitano, Michelle Frazão; Soares, Angélica Ribeiro

doi:10.3390/molecules19033181

Cited by 28 publications

(30 citation statements)

References 33 publications

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“…Furthermore, a significant number of Laurencia sesquiterpenes including (-)-(10R)-bromo-α-chamigrene (1) [81], laurecomin C (2) [84], 7 [84], laurokamin C (12) [79], 10-bromo-9-hydroxy-α-chamigrene (14) [81], dendroidiol (34) [146], laurecomin B (37) [84], 10-bromo-β-chamigren-8-ol (41) [152,275], 44 [62,155] 10-hydroxy-kahukuene B (633) [74], aplysiadiol (638) [187], and (E)-phytol (641) [342] have been evaluated for their antibacterial and antifungal properties.…”

Section: Antibacterial and Antifungal Activitymentioning

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: Antibacterial and Antifungal Activitymentioning

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 only secochamigrane (82) and norchamigrane (83) sesquiterpenes were identified from Japanese L. nipponica and L. majuscula, respectively, which were also possibly derived from the oxidation of their brominated congeners (Kurata et al 1983;Suzuki et al 1987b). Two triquinane isomers (84 and 85) from Australian L. majuscula were typical representatives of rarely occurring frameworks without any halogenated derivatives, and 84 exhibited the leishmanicidal activity (Coll and Wright 1989;da Silva Machado et al 2011;Wright and Coll 1990). Three aromatic sesquiterpenes were characterized from Australian L. majuscula (86) and Chinese L. tristicha (87) and L. karlae (88), which featured unprecedented 7,12-cyclized bisabolane, rearranged cyclolaurane, and benkarlane skeletons, respectively (Sun et al 2005b(Sun et al , 2008de Nys et al 1992;Zeng et al 1996).…”

Section: Miscellaneous Sesquiterpenesmentioning

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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“…L. luzonensis from Okinawan waters yielded (3Z,6E)-1-bromo-2-hydroxy-3,7,11-trimethyldodeca-3,6,10-triene (200), isopalisol (201), luzonensol (202) and luzonensol acetate (203) [95], while, the norsesquiterpene derivative, 2-bromo-β-ionone (204) was isolated from L. saitoi (Hainan coastline, China) [97]. A triquinane derivative (205) was identified from L. dendroidea, in the Brazilian coast, and was found to be moderately active against Leishmania amazonensis (IC 50 43.8µg/mL) [109] (Table 2 and Figure 10). …”

Section: Other Skeletons Sesquiterpenesmentioning

confidence: 99%

“…A Chinese sample of L. similis (Hainan Is., China) yielded aristolane (53), formerly known as a synthetic compound [54], from a natural source for the first time. In addition, aristolan-10-ol-9-one (54), aristolan-8-en-1-one (55), aristol-1(10)-en-9-one (56), 9 β -aristol-1(10)-en-9-ol (57), aristol-1(10),8-diene (58) and aristol-1,9-diene (59) were also isolated and identified [55].…”

Section: Aristolane Skeleton Sesquiterpenesmentioning

confidence: 99%