Cytotoxic, Anti-inflammatory, and Antibacterial Sulfur-Containing Polybromoindoles from the Formosan Red Alga <i>Laurencia brongniartii</i>

Fang, Hui; Chiou, Shu Fen; Uvarani, Chokkalingam; Wen, Z.H.; Hsu, Chi Hsin; Wu, Yang Chang; Wang, Wei Lung; Liaw, Chih Chuang; Sheu, Jyh‐Horng

doi:10.1246/bcsj.20140165

Cited by 17 publications

(11 citation statements)

References 20 publications

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“…A collection of Formosan Laurencia brongniarii afforded the new polybrominated indole, 4,5,6-tribromo-2-methylsulfinylindole ( 118 ) in addition to 11 known brominated indoles ( Figure 21 ) [ 62 ]. Although 118 is inactive, of the known indoles, 119 – 121 show significant antibacterial activity against Enterobacter aerogenes (ATCC 13048), Salmonella enteritidis (ATCC 13076), and Serratia marcescens (ATCC 25419).…”

Section: Antibacterial Activitymentioning

confidence: 99%

Biological Activity of Recently Discovered Halogenated Marine Natural Products

2015

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Section: Antibacterial Activitymentioning

confidence: 99%

Biological Activity of Recently Discovered Halogenated Marine Natural Products

2015

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“…When the indoles 955-958, 960-963, 965, and 975-977 were evaluated against the HT-29 and P-388 cancer cell lines, compound 976 exhibited cytotoxicity against both cancer cell lines, while 977 was active only against the P-388 cell line [799]. The cytotoxic activity of 4,5,6-tribromo-2-methylsulfinylindole (964), along with other known related compounds was evaluated [801].…”

Section: Cytotoxic Activitymentioning

confidence: 99%

“…The antimicrobial activity of a Laurencia complanata extract containing the bromoindoles 952, 969, and 971 and the aristolane debilone (456) could be, at least to some extent, attributed to the presence of compound 952 [433]. The antibacterial activity of 4,5,6-tribromo-2-methylsulfinylindole (964), along with a series of other previously reported related compounds has been examined [801].…”

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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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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“…Many of these compounds possess various interesting biological properties that includes antidiabetic [ 16 ], cytotoxic [ 17 ], antifungal [ 18 ], anti-HIV [ 19 ], antibacterial [ 20 ], antitumor [ 21 ] and potent antioxidant (vitamin E) [ 22 , 23 ] activities. Recently, we also reported cytotoxic, anti-inflammatory, and antibacterial properties of sulfur-containing polybromoindoles from the Formosan red alga Laurencia brongniartii [ 24 ]. Consequently, the study has been undertaken to assess the cytotoxic, antibacterial, and anti-inflammatory activities of isolated compounds 1 – 6 .…”

Section: Introductionmentioning

confidence: 99%

Bioactive Chemical Constituents from the Brown Alga Homoeostrichus formosana

Fang

Uvarani

Chiou

et al. 2014

IJMS

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A new chromene derivative, 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-hydroxy-2,6-dimethyl-2H-chromene (1) together with four known natural products, methylfarnesylquinone (2), isololiolide (3), pheophytin a (4), and β-carotene (5) were isolated from the brown alga Homoeostrichus formosana. The structure of 1 was determined by extensive 1D and 2D spectroscopic analyses. Acetylation of 1 yielded the monoacetylated derivative 2-(4',8'-dimethylnona-3'E,7'-dienyl)-8-acetyl-2,6-dimethyl-2H-chromene (6). Compounds 1–6 exhibited various levels of cytotoxic, antibacterial, and anti-inflammatory activities. Compound 2 was found to display potent in vitro anti-inflammatory activity by inhibiting the generation of superoxide anion (IC50 0.22 ± 0.03 μg/mL) and elastase release (IC50 0.48 ± 0.11 μg/mL) in FMLP/CB-induced human neutrophils.

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Cytotoxic, Anti-inflammatory, and Antibacterial Sulfur-Containing Polybromoindoles from the Formosan Red Alga Laurencia brongniartii

Cited by 17 publications

References 20 publications

Biological Activity of Recently Discovered Halogenated Marine Natural Products

Biological Activity of Recently Discovered Halogenated Marine Natural Products

The Laurencia Paradox: An Endless Source of Chemodiversity

Bioactive Chemical Constituents from the Brown Alga Homoeostrichus formosana

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