Chemical relationship between red algae genus Laurencia and sea hare (Aplysia dactylomela Rang) in the North Borneo Island

Palaniveloo, Kishneth; Vairappan, Charles Santhanaraju

doi:10.1007/s10811-013-0127-z

Cited by 15 publications

(28 citation statements)

References 21 publications

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“…(1) those belonging to the α-chamigrene series possessing a trisubstituted double bond between C-7 and C-8 (1-26); (2) possessing an exomethylene group at C-7 (27-77); (3) those featuring an oxygenation site at C-7 (78-99); and (4) those with either a 5,10-epoxide ring system (100-117) or another epoxide (118)(119)(120)(121)(122)(123)(124) or a lactone ring connecting the two sixmembered rings (125)(126)(127)(128)(129). Most chamigranes possess various halogen and oxygen substitutions, with C-10 being a favored position for a Br substitution.…”

Section: Chamigranes and Related Sesquiterpenesmentioning

confidence: 99%

“…In the 1990s, Guella and co-workers undertook thorough conformational studies of α-and β-chamigrenes using temperaturedependent NMR spectra [164,472,473]. Majusculone (130) and mailione (131) are the only two known nor-chamigranes isolated from a number of different Laurencia species [118,122,128,134,142,143,147]. Compounds 132-146 possess a rearranged chamigrane carbocycle that arises from a methyl migration from C-11 to C-10 of the chamigrane skeleton, whereas kylinone (147), isolated as a constituent of L. pacifica from the Monterey Peninsula, California [211], is the sole representative of another rearranged chamigrane framework, in all probability derived from a methyl migration from C-7 to C-8.…”

Section: Chamigranes and Related Sesquiterpenesmentioning

confidence: 99%

“…The bromoketone 484, isolated from Laurencia mariannensis collected from Geoffrey Bay, Magnetic Island, Australia [198], is the sole representative of this carbocycle containing a bicyclo[4.3.0]nonane core, different, however, from the oplopane skeleton. Pacifigorgiol (485) is a highly rearranged sesquiterpene representing the pacifigorgiane skeleton and has been reported as a constituent of several Laurencia species [118,149,323,335,451]. Laurencial (486), containing a spiro[4.5]decane core, was obtained from Laurencia nipponica collected off the Pacific Coast of Hokkaido [452] and its synthesis was achieved utilizing the stereospecific bromination-cyclization of spirocyclic cyclohexanones [453].…”

Section: Miscellaneous Sesquiterpenesmentioning

confidence: 99%

“…Pacifenol (105), cycloelatanenes A (119) and B (118), and the acetogenin (3Z )-chlorofucin (875) displayed negligible cytotoxic activity when tested [221]. The inhibition of cytokinesis in the embryos of the sea urchin Tetrapygus niger, used as a preliminary test for an indication of antineoplastic activity, revealed that 4,10-dibromo-3-chloro-α-chamigrene (5), prepacifenol (88), deoxyprepacifenol (87), and claviol (124) had no effect on the cytokinesis, while 6 and pacifenol (105) displayed only weak inhibition [87].…”

Section: Cytotoxic 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 102

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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: Chamigranes and Related Sesquiterpenesmentioning

confidence: 99%

Section: Chamigranes and Related Sesquiterpenesmentioning

confidence: 99%

Section: Miscellaneous Sesquiterpenesmentioning

confidence: 99%

Section: Cytotoxic 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 102

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“…MarinLit database was queried against the taxonomic criterion of Laurencia and Aplysia genera, since molluscs of the genus Aplysia preferentially feed on Laurencia species and sequester the algal secondary metabolites in their digestive glands (Kladi et al, 2014;Palaniveloo and Vairappan, 2014;Stallard and Faulkner, 1974). A list of 411 molecular formulas (excluding redundant hits), corresponding to approx.…”

Section: Uhplc-pda-hrms Screening Of Laurencia Crude Extractsmentioning

confidence: 99%

An integrated approach using UHPLC–PDA–HRMS and 2D HSQC NMR for the metabolic profiling of the red alga Laurencia: Dereplication and tracing of natural products

et al. 2014

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New advances in the volatile metabolites of Frullania tamarisci

Pannequin

Tintaru

Desjobert

et al. 2017

Flavour & Fragrance J

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The chemical composition of Frullania tamarisci essential oil from Corsica was investigated using GC‐FID, GC–MS and NMR analyses. The essential oil compositions were further studied analyzing samples prepared from three different Corsican locations and during a seasonal vegetative cycle. 40 components, which accounted for 78.3–89.8% of the total amount of F. tamarisci essential oils were identified. The main components were tamariscol coeluted with pacifigorgiol (30.4–41.5%), germacra‐1(10)E,5E–dien‐11‐ol (3.6–7.1%), γ‐cylocostunolide (1.8–20.1%), γ‐dihydrocyclocostunolide (1.2–8.0%) and frullanolide (1.7–4.9%). Among them, germacra‐1(10)E,5E–dien‐11‐ol was never reported in the Frullania genus and pacifigorgiol, a tamariscol GC‐overlapped compound, was for the first time reported in Bryophytes. Finally using 1D and 2D NMR experiments, we reported γ‐dihydrocyclocostunolide as a new natural compound. Two Corsican F. tamarisci essential oils with different GC profiles were assessed for their phytotoxic behavior against onion seeds and seedling in order to evaluate their capacity to inhibit germination and alter the development of plantlets. According to the essential oil‐compositions, a stimulation of the onion seedling was observed when sesquiterpene lactones amount was higher, whilst the inhibition of roots growth occurs when sesquiterpene alcohols were predominantly.

show abstract

Chemical relationship between red algae genus Laurencia and sea hare (Aplysia dactylomela Rang) in the North Borneo Island

Cited by 15 publications

References 21 publications

The Laurencia Paradox: An Endless Source of Chemodiversity

The Laurencia Paradox: An Endless Source of Chemodiversity

An integrated approach using UHPLC–PDA–HRMS and 2D HSQC NMR for the metabolic profiling of the red alga Laurencia: Dereplication and tracing of natural products

New advances in the volatile metabolites of Frullania tamarisci

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