Additional analysis of chemical diversity of the red algal genus Laurencia (Rhodomelaceae) from Japan

Masuda, Michio; Kawaguchi, Shigeo; Abe, Tsuyoshi; Kawamoto, Tomotake; Suzuki, Minoru

doi:10.1111/j.1440-1835.2002.tb00144.x

Cited by 24 publications

(10 citation statements)

References 41 publications

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“…Both the 1 H and 13 C NMR spectroscopic data were identical to those previously reported [13]. Allolaurinterol (3) has also been isolated from other algae including L. subopposita [36], L. majuscula [37] and L. obtusa [38], and the sea hare Aplysia dactylomela [39], as well as having been synthesized [40].…”

Section: 'supporting

confidence: 67%

Laurencia Filiformis: Phytochemical Profiling by Conventional and HPLC-NMR Approaches

Dias

White

Urban

2009

Natural Product Communications

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Chemical investigation of the southern Australian marine alga Laurencia filiformis forma heteroclada resulted in the isolation of two new compounds, cycloisoallolaurinterol (16) and isoallolaurinterol (23), along with the previously reported sesquiterpenes filiformin (1), filiforminol (2), allolaurinterol (3) and bromolaurenisol (10). All structures were secured by detailed spectroscopic analysis since no previous 2D NMR studies had been described for compounds 1, 2 and 10. As a result of this study, the first single X-ray diffraction study for 1 was secured. The investigation of the chemical conversion of allolaurinterol (3) to filiformin (1) was monitored by on-flow HPLC-NMR, which also resulted in the identification of 23. We propose that both compounds 16 and 23 are formed as artefacts from allolaurinterol (3). HPLC-NMR was used to profile the crude extract of a marine organism, as well as for monitoring on-line compound chemical conversions. Both on-flow and stop-flow HPLC-NMR were successfully applied in the chemical profiling and compound chemical conversion studies of L. filiformis forma heteroclada. Compounds 2 and 3 displayed antimicrobial activities.

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Section: 'supporting

confidence: 67%

Laurencia Filiformis: Phytochemical Profiling by Conventional and HPLC-NMR Approaches

Dias

White

Urban

2009

Natural Product Communications

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“…Compounds 1 (laurinterol) and 2 (isolaurinterol) were isolated from L. okamurae Yamada collected at Oshoro Bay, Hokkaido, Japan [13]. Compounds 3 (allolaurinterol; 10-bromo-7-hydroxylaurene) and 4 (cupalaurenol) were isolated from L. majuscula (Harvey) Lucas and L. venusta Yamada, respectively, collected at Tanegashima Island, Kagoshima Prefecture, Japan [18]. Two halochamigrene derivatives, compounds 5 (elatol) and 6 (iso-obtusol) were isolated from L. majuscula (Harvey) Lucas collected at several locations in Malaysia, e. g., Pulau Bankawan, Sandakan, Sabah, Malaysia [10].…”

Section: Methodsmentioning

confidence: 99%

Potent Antibacterial Activity of Halogenated Compounds against Antibiotic-Resistant Bacteria

et al. 2004

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Common Gram-positive clinical pathogens are showing an increasing trend for resistance to conventional antimicrobial agents. New drugs with potent antibacterial activities are urgently needed to remediate this problem. Halogenated compounds isolated from several species of the red algae genus Laurencia were examined for their antibacterial activity against 22 strains of human pathogenic bacteria, 7 strains of which were antibiotic-resistant bacteria. Four phenolic sesquiterpenes and a polybrominated indole showed wide spectra of antibacterial activity against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), penicillin-resistant Streptococcus pneumoniae, and vancomycin-resistant Enterococcus faecalis and E. faecium (VRE). In addition, laurinterol and allolaurinterol displayed potent bactericidal activity against three strains of MRSA at 3.13 microg mL(-1), and three strains of vancomycin-susceptible Enterococcus, at 3.13 microg mL(-1) and 6.25 microg mL(-1), respectively.

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“…Experimental crosses between representative individuals of the chemical types showed that such chemically distinct populations are not reproductively isolated. Thus, the diverse chemical types can be referred to as races (chemical races) [69].…”

Section: Chemical Variation In Laurenciamentioning

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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Additional analysis of chemical diversity of the red algal genus Laurencia (Rhodomelaceae) from Japan

Cited by 24 publications

References 41 publications

Laurencia Filiformis: Phytochemical Profiling by Conventional and HPLC-NMR Approaches

Laurencia Filiformis: Phytochemical Profiling by Conventional and HPLC-NMR Approaches

Potent Antibacterial Activity of Halogenated Compounds against Antibiotic-Resistant Bacteria

The Laurencia Paradox: An Endless Source of Chemodiversity

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