Thyrsiferol: a squalene-derived metabolite of

Blunt, John W.; Hartshorn, MP; McLennan, Tamara J.; Munro, Murray H. G.; Robinson, Ward T.; Yorke, Selwyn C.

doi:10.1016/s0040-4039(01)88986-3

Cited by 100 publications

(54 citation statements)

References 4 publications

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“…The triterpene thyrsiferol (646) and its 23-acetate (647), when tested, did not show any antimicrobial activity [545]. Aplysqualenol A (675) did not exhibit any inhibitory activity against M. tuberculosis [567].…”

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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“…Detailed NMR and mass spectroscopic analyses established that 1 -3 were highly oxidized squalene derivatives, of which 1 and 2 were new compounds, and 3 was thyrsiferol. Thyrsiferol (3) has previously been isolated several times from the marine algal species L. thyrsifera [12] and L. obtusa [14], and it has been synthesized by González and Forsyth [13]. However, only 1 H-NMR data were reported.…”

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confidence: 99%

Highly Oxygenated Triterpenoids from the Marine Red Alga Laurencia mariannensis (Rhodomelaceae)

Xie

et al. 2008

Helvetica Chimica Acta

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Two new and one known squalenoid-derived triterpenoids, namely, laurenmariannol (1) and (21a)-21-hydroxythyrsiferol (2), and the known thyrsiferol (3) were isolated and identified from the marine red alga Laurencia mariannensis, which was collected off the coast of Hainan and Weizhou Islands of China. The structures of these compounds were established by means of spectroscopic analyses, as well as by comparison with literature data. Compounds 1 and 2 displayed significant cytotoxic activity against P-388 tumor cells with IC 50 values of 0.6 and 6.6 mg/ml, respectively.Introduction. -Marine red algal species of the genus Laurencia, i.e., L. viridis, L. obtusa, L. thyrsifera, L. pinnatifida, and L. venusta were found to be a prolific source of triterpenoids, which are characterized by a high degree of oxygenation and fused cyclicether systems. These triterpenoids exhibited potent cytotoxic effects against some tumor cell lines [1].In our investigations towards the discovery of structurally new and biologically active compounds from Chinese marine red algal species of Rhodomelaceae [2 -11], we examined the chemical constituents of L. mariannensis, which was collected off the coast of Hainan and Weizhou Islands of China. As a result, two new and one known triterpenoids, namely, laurenmariannol (1) and (21a)-21-hydroxythyrsiferol 1 ) (2), and the known thyrsiferol (3) [12 -14], were isolated and characterized. This paper reports the isolation and structure identification of these compounds and the cytotoxic activity of compounds 1 and 2.

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“…Since aplysqualenol A displayed signals for only one unsaturated bond [ δ C 144.4 (C) and 113.8 (CH 2 ); δ H 4.87 (1H, br s) and 4.93 (1H, br s)], 1 was assumed to comprise four oxacyclic units. The detailed analysis of the 1 H– 1 H COSY, HMQC, and HMBC spectra of 1 showed the presence of the same partial structural units in the molecule (rings A–B–C) as those in thyrsiferol ( 5 ) and venustatriol ( 6 ), isolated from red algae of the genus Laurencia , [5,6] and aplysiol A ( 7 ) and B ( 8 ), isolated recently from South China Sea specimens of A. dactylomela . [7] Furthermore, the 1 H– 1 H COSY and HMBC data, summarized in Table 1, allowed the foregoing partial structures (C1 through C15 and C25 through C28) and the remaining ring system D (C16 through C24 and C29 through C31) to be connected, establishing the connectivities of all the carbon atoms in 1 as shown.…”

Section: Resultsmentioning

confidence: 99%

Aplysqualenols A and B: Squalene‐Derived Polyethers with Antitumoral and Antiviral Activity from the Caribbean Sea Slug Aplysia dactylomela

Vera¹,

Rodrı́guez²,

Avilés³

et al. 2009

Eur J Org Chem

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The novel bromotriterpene polyethers aplysqualenol A (1) and aplysqualenol B (2) have been isolated from the Caribbean sea slug Aplysia dactylomela collected in Puerto Rico, and their structures and relative configurational assignments established from spectroscopic data aided by quantum mechanical calculations of NMR chemical shifts. Although both these compounds may be conceived as polyoxycyclic derivatives of the C30 squalene skeleton, remarkably 1 and 2 possess an unprecedented C15 to C24 flexible chain of 14S* spatial disposition that contains a unique ether bridge between C16 and C19. Biological activity screening tests revealed that, although aplysqualenol A (1) does not have significant anti-infective properties, it possesses potent antitumoral and antiviral activities.

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Thyrsiferol: a squalene-derived metabolite of

Cited by 100 publications

References 4 publications

The Laurencia Paradox: An Endless Source of Chemodiversity

The Laurencia Paradox: An Endless Source of Chemodiversity

Highly Oxygenated Triterpenoids from the Marine Red Alga Laurencia mariannensis (Rhodomelaceae)

Aplysqualenols A and B: Squalene‐Derived Polyethers with Antitumoral and Antiviral Activity from the Caribbean Sea Slug Aplysia dactylomela

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