The structure of pacifigorgiol, an ichthyotoxic sesquiterpenoid from the pacific gorgonian coral

Izac, Richard R.; Poet, Steven E.; Fenical, William; Engen, D. Van; Clardy, Jon

doi:10.1016/s0040-4039(00)87695-9

Cited by 34 publications

(14 citation statements)

References 4 publications

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“…In this mechanism C1 forms a bond with C11 of the originating FPP molecule in the formation of a caryophyllenyl carbocation followed by opening of the cyclobutyl ring to yield the desired isobutenyl side chain. Important to note, the two methylene carbons of the isobutenyl side are predicted to arise from C1 and C11 of the originating FPP and hence should become labeled when [1][2][3][4][5][6][7][8][9][10][11][12][13] C]acetate is incorporated into FPP by the mevalonate biosynthetic pathway operating in yeast (32). This labeling pattern is indeed observed and consistent with the proposed caryophyllene reaction mechanism for valerena-1,10-diene synthase.…”

Section: Discussionsupporting

confidence: 59%

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Functional Identification of Valerena-1,10-diene Synthase, a Terpene Synthase Catalyzing a Unique Chemical Cascade in the Biosynthesis of Biologically Active Sesquiterpenes in Valeriana officinalis

Yeo

Nybo

Chittiboyina

et al. 2013

Journal of Biological Chemistry

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Background: Therapeutic values of Valeriana officinalis have been associated with sesquiterpenes whose biosynthetic origins have remained enigmatic. Results: A cyclobutenyl intermediate in the catalytic cascade of valerena-1,10-diene synthase is reported. Conclusion: A new class of sesquiterpene synthases for the biosynthesis of sesquiterpenes harboring isobutenyl functional groups is proposed. Significance: Similar catalytic mechanisms from evolutionarily diverse organisms are proposed and portend sources for sesquiterpene diversity.

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Section: Discussionsupporting

confidence: 59%

“…1). However, valerenadiene has been of particular interest to others studying related biologically active sesquiterpene compounds like tamariscol (10), tamariscene (11), and pacifigorgiol (12) (Fig. 1) because the biogenic origin of the isobutenyl substituent group common to these molecules has remained enigmatic.…”

mentioning

confidence: 99%

Functional Identification of Valerena-1,10-diene Synthase, a Terpene Synthase Catalyzing a Unique Chemical Cascade in the Biosynthesis of Biologically Active Sesquiterpenes in Valeriana officinalis

Yeo

Nybo

Chittiboyina

et al. 2013

Journal of Biological Chemistry

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“…Pacifigorgiol (485), a highly rearranged sesquiterpene, exhibited toxicity towards the reef-dwelling fish Eupomacentrus leucostictus [900].…”

Section: Antifeedant Activity and Toxicity To Marine Organismsmentioning

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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“…14,15 The furanosesquiterpene furanotriene, which represents one of the most abundant volatile metabolites in the three gorgonian species, was originally reported from the coral Pseudopterogorgia americana. 16 A few years later, the isolation of isofuranotriene was published from the same organism. 17 The compound trans, transGermacrone was identified in the Indian and African medicinal plant Fagara chalybea.…”

Section: Resultsmentioning

confidence: 99%

Antibacterial activity of volatile secondary metabolites from Caribbean soft corals of the genus Gorgonia

Roussis

Chinou

Tsitsimpikou

et al. 2001

Flavour & Fragrance J

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The volatile secondary metabolites of Caribbean corals from three species of the genus Gorgonia were studied. The main constituents of the gorgonian species G. ventalina, G. flabelum and G. mariae were identified and 12 metabolites were isolated and identified. The in vitro antibacterial activity of the volatile constituents was also studied against six Gram-positive or -negative bacteria exhibiting a wide spectrum of antibacterial activities. Furanotriene, dihydro-˛-santalen-12-one and E-nerolidol showed the most interesting antibacterial action.

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The structure of pacifigorgiol, an ichthyotoxic sesquiterpenoid from the pacific gorgonian coral

Cited by 34 publications

References 4 publications

Functional Identification of Valerena-1,10-diene Synthase, a Terpene Synthase Catalyzing a Unique Chemical Cascade in the Biosynthesis of Biologically Active Sesquiterpenes in Valeriana officinalis

Functional Identification of Valerena-1,10-diene Synthase, a Terpene Synthase Catalyzing a Unique Chemical Cascade in the Biosynthesis of Biologically Active Sesquiterpenes in Valeriana officinalis

The Laurencia Paradox: An Endless Source of Chemodiversity

Antibacterial activity of volatile secondary metabolites from Caribbean soft corals of the genus Gorgonia

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