Halogenated metabolites from Japanese Laurencia spp.

Suzuki, Minoru; Kawamoto, Tomotake; Vairappan, Charles Santhanaraju; Ishii, Takahiro; Abe, Tsuyoshi; Masuda, Michio

doi:10.1016/j.phytochem.2005.08.008

Cited by 28 publications

(18 citation statements)

References 16 publications

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“…Evaluation of the related sesquiterpenes allolaurinterol (151) [166,248,259,260,855,877], allolaurinterol acetate (152) [152,260], debromoallolaurinterol (149) [248], debromoallolaurinterol acetate (150) [152], isolaurinterol (161) [62,201,267,279,877], laurinterol (231) [62,105,137,309,877], debromolaurinterol (226) [309,855,878], and isodebromolaurinterol (229) [201,267,279] has been performed in several, albeit fragmented, studies, which do not allow direct comparison of the structural features with the reported antimicrobial activities.…”

Section: Antibacterial and Antifungal Activitymentioning

confidence: 99%

“…The antibacterial and/or antifungal activities of the acetogenins laurenmariallene (741) [74], chinzallene (749) [105], (12E)-lembyne A (759) [62], lembyne A (763) [165], (3Z)-laurenyne (798) [513], (Z)-chondriol (803) [878], ent-854 [152], desepilaurallene (862) [152], and (3Z )-chlorofucin (875) [238] have also been evaluated in a number of studies.…”

Section: Antibacterial and Antifungal Activitymentioning

confidence: 99%

“…A number of semisynthetic derivatives of pacifenol (105) were also assayed in a similar manner [852].…”

Section: Brine Shrimp Toxicitymentioning

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: Antibacterial and Antifungal Activitymentioning

confidence: 99%

Section: Antibacterial and Antifungal Activitymentioning

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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“…Since, red algae of the genus Laurencia are known to synthesize and store a wide array of halogenated secondary metabolites in their corps en cerise at the surface cortex cells (Masuda et al 1997a;Vairappan et al 2004;Suzuki et al 2005), detailed investigation by bioassay-guided isolation and identification of defense chemicals against bacteria isolated from "ice-ice" disease infected seaweed was carried out. Here, we report the isolation, identification and antibacterial activity of the secondary metabolites from two populations of L. majuscula found growing in two major seaweed cultivation districts in Sabah.…”

Section: Introductionmentioning

confidence: 99%

Role of secondary metabolites as defense chemicals against ice-ice disease bacteria in biofouler at carrageenophyte farms

et al. 2009

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Carrageenophyte farming is an expanding economical activity in North Borneo Island, Malaysia. During routine monitoring of "ice-ice" disease and epiphyte outbreak at commercial farms, it was apparent that culture lines were heavily (60-80%) infested with biofoulers, particularly Acanthophora spp. and Laurencia majuscula. However, only L. majuscula showed dominance and flourished even during "ice-ice" disease outbreak. Presence of chemical defense against seaweed pathogens was investigated in two populations of L. majuscula collected from three major carrageenophyte farms in two districts; (A) Lohok Butun, Selakan Island, and Bum-Bum Island, in Semporna district, and (B) Telutuh, Carrington Reef, and Balambangan Island, in Kudat district. The first population contained elatol (1), and iso-obtusol (2), and, second population contained (Z)-10,15-dibromo-9-hydroxy-chamigra-1,3(15),7(14)-triene (3) and (E)-10-15-dibromo-9-hydroxy-chamigra-1,3(15),7(14)-triene (4), as their antibacterial metabolites. All four metabolites showed highly selective inhibition against "ice-ice" disease bacteria compared to human pathogens at 30µg disk −1 . In addition, seasonal variation of these compounds at two representative farms (Selakan Island [P-1] and Balambangan Island [P-2]) revealed a 120-170% increase in concentration during "ice-ice" disease outbreak. Microscopy of fresh specimens showed the presence of corps en cerise, which is the synthesis and storage site of halogenated metabolites at superficial cortical cells, branch tips, and trichoblasts. This suggests the importance of these metabolites as defense chemicals against "ice-ice" disease bacteria in L. majuscula that grows on seaweed culture lines.

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“…However, today they are found in the genus Laurencia in great abundance [100]. Despite already having several isolated molecules, their biological activities have been little explored.…”

Section: Red Seaweeds As a Source Of New Bioactive Prototypesmentioning

confidence: 99%

Seaweeds as Source of New Bioactive Prototypes

Nogueira¹,

Teixeira²

2016

Algae - Organisms for Imminent Biotechnology

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Living organisms endowed with natural benefits have been used for millions of years in the medical practice. Seaweeds have been widely used around the world for the production of agar and food; however, the pharmaceutical industry has drawn attention to the activities of these natural products. In this chapter, we present some bioactive metabolites of the three phyla of seaweed (green, brown, and red algae) along with their potential for drug development.

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Halogenated metabolites from Japanese Laurencia spp.

Cited by 28 publications

References 16 publications

The Laurencia Paradox: An Endless Source of Chemodiversity

The Laurencia Paradox: An Endless Source of Chemodiversity

Role of secondary metabolites as defense chemicals against ice-ice disease bacteria in biofouler at carrageenophyte farms

Seaweeds as Source of New Bioactive Prototypes

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