Thyrsenols A and B, two unusual polyether squalene derivatives

Norte, Manuel; Fernández, JoséJ.; Souto, Marı́a L.; Gavín, José A.; Garcia‐Gravalos, M. D.

doi:10.1016/s0040-4020(97)00028-8

Cited by 43 publications

(27 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Teurilene (699) did not show any cytotoxicity against P-388 cells [544], but was found to be cytotoxic against KB cells (IC 50 ¼ 7.0 μg/cm 3 ) [865]. The mechanisms of growth inhibition by the cytotoxic compound dehydrothyrsiferol (649) have been studied extensively [548,563,568,569]. In particular, 649 was shown to circumvent multidrug resistance mediated by P-glycoprotein [866] and to cause growth inhibition in KB cancer cells without inducing apoptosis [867], but did not modulate multidrug resistance-associated protein 1 (MRP1) resistance [868].…”

Section: Cytotoxic Activitymentioning

confidence: 99%

The Laurencia Paradox: An Endless Source of Chemodiversity

Harizani

Iοannou

Roussis

2016

Progress in the Chemistry of Organic Natural Products

View full text Add to dashboard Cite

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.

show abstract

Section: Cytotoxic Activitymentioning

confidence: 99%

The Laurencia Paradox: An Endless Source of Chemodiversity

Harizani

Iοannou

Roussis

2016

Progress in the Chemistry of Organic Natural Products

View full text Add to dashboard Cite

show abstract

“…In another search, sesquiterpene derivatives were obtained from the species Laurencia scoparia [10]. In a study on Laurencia pinnatifida, a series of polyether derivatives were obtained [11].…”

mentioning

confidence: 99%

Extracts and Sesquiterpene Derivatives from the Red Alga Laurencia chondrioides with Antibacterial Activity against Fish and Human Pathogenic Bacteria

Bansemir

Just

Michalik

et al. 2004

Chemistry & Biodiversity

View full text Add to dashboard Cite

During screening of seaweeds from different places in Europe for antimicrobial activities against human and fish pathogenic bacteria, Laurencia chondrioides was identified as a promising species. By bioassay-guided isolation, followed by structure elucidation by mass spectrometry and 1H- and 13C-NMR spectrometry, two sesquiterpenoides of the chamigrene-type from the selected red seaweed Laurencia chondrioides were identified. Both compounds inhibit the growth of some fish and human pathogenic bacteria.

show abstract

“…A peculiar situation arose while interpreting the 1 H NMR data of epoxymalabaricol (7). This compound contains two THF rings in the side chain attached to C-13 of the malabaricane ring system (Fig.…”

Section: Discussionmentioning

confidence: 99%

Stereochemistry of 2,2,5‐trisubstituted tetrahydrofuran ring‐containing natural products based on ¹H NMR spectroscopy: some observations

Achanta

Akkinepally

Achanta

2015

Magnetic Reson in Chemistry

View full text Add to dashboard Cite

Thyrsenols A and B, two unusual polyether squalene derivatives

Cited by 43 publications

References 8 publications

The Laurencia Paradox: An Endless Source of Chemodiversity

The Laurencia Paradox: An Endless Source of Chemodiversity

Extracts and Sesquiterpene Derivatives from the Red Alga Laurencia chondrioides with Antibacterial Activity against Fish and Human Pathogenic Bacteria

Stereochemistry of 2,2,5‐trisubstituted tetrahydrofuran ring‐containing natural products based on ¹H NMR spectroscopy: some observations

Contact Info

Product

Resources

About

Thyrsenols A and B, two unusual polyether squalene derivatives

Cited by 43 publications

References 8 publications

The Laurencia Paradox: An Endless Source of Chemodiversity

The Laurencia Paradox: An Endless Source of Chemodiversity

Extracts and Sesquiterpene Derivatives from the Red Alga Laurencia chondrioides with Antibacterial Activity against Fish and Human Pathogenic Bacteria

Stereochemistry of 2,2,5‐trisubstituted tetrahydrofuran ring‐containing natural products based on 1H NMR spectroscopy: some observations

Contact Info

Product

Resources

About

Stereochemistry of 2,2,5‐trisubstituted tetrahydrofuran ring‐containing natural products based on ¹H NMR spectroscopy: some observations