Diterpenoids from Cascarilla (<i>Croton eluteria</i>Bennet)

Fattorusso, Ernesto; Taglialatela‐Scafati, Orazio; Campagnuolo, Claudio; Santelia, Federico Umberto; Appendino, Giovanni; Spagliardi, Paola

doi:10.1021/jf0203693

Cited by 17 publications

(22 citation statements)

References 13 publications

(39 reference statements)

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“…Homoserine lactones were acquired from Darren Furniss (University of Nottingham, United Kingdom). Noncommercial bitter terpenoids were obtained by isolation from their plant sources (107)(108)(109)(110)(111)(112). All other substances were available from previous studies (32,37).…”

Section: Methodsmentioning

confidence: 99%

Comprehensive Analysis of Mouse Bitter Taste Receptors Reveals Different Molecular Receptive Ranges for Orthologous Receptors in Mice and Humans

Lossow

Hübner

Roudnitzky

et al. 2016

Journal of Biological Chemistry

178

273

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One key to animal survival is the detection and avoidance of potentially harmful compounds by their bitter taste. Variable numbers of taste 2 receptor genes expressed in the gustatory end organs enable bony vertebrates (Euteleostomi) to recognize numerous bitter chemicals. It is believed that the receptive ranges of bitter taste receptor repertoires match the profiles of bitter chemicals that the species encounter in their diets. Human and mouse genomes contain pairs of orthologous bitter receptor genes that have been conserved throughout evolution. Moreover, expansions in both lineages generated species-specific sets of bitter taste receptor genes. It is assumed that the orthologous bitter taste receptor genes mediate the recognition of bitter toxins relevant for both species, whereas the lineagespecific receptors enable the detection of substances differently encountered by mice and humans. By challenging 34 mouse bitter taste receptors with 128 prototypical bitter substances in a heterologous expression system, we identified cognate compounds for 21 receptors, 19 of which were previously orphan receptors. We have demonstrated that mouse taste 2 receptors, like their human counterparts, vary greatly in their breadth of tuning, ranging from very broadly to extremely narrowly tuned receptors. However, when compared with humans, mice possess fewer broadly tuned receptors and an elevated number of narrowly tuned receptors, supporting the idea that a large receptor repertoire is the basis for the evolution of specialized receptors. Moreover, we have demonstrated that sequence-orthologous bitter taste receptors have distinct agonist profiles. Species-specific gene expansions have enabled further diversification of bitter substance recognition spectra.The plethora of natural compounds that taste bitter for humans comprises numerous chemicals with pharmacological activities that can make them powerful toxins, such as the alkaloids strychnine and colchicine or the sesquiterpene lactone picrotoxinin (1). However, compounds believed to exert health-beneficial effects such as the antioxidative phytoestrogen genistein from soy (2), the analgesic drug acetaminophen (3), or various polyphenols also taste bitter (4). To avoid ingestion of bitter substances that would pose a threat to organisms, efficient recognition and rejection mechanisms have developed throughout the animal kingdom. In bony vertebrates (Euteleostomi), the avoidance of bitter compounds is centered on taste receptors that detect potentially harmful substances with high accuracy and adequate sensitivity (5). Vertebrate bitter taste receptors, called taste 2 receptors (TAS2R (human) or Tas2r (murine)), 2 are G protein-coupled receptors only remotely related to other classes of this large and enormously versatile receptor family (6 -10). During evolution the first Tas2r genes appeared in the genomes of bony fish (11). In higher vertebrates frequent independent expansions and pseudogenization events resulted in differently sized Tas2r gene repertoires (12). Cons...

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Section: Methodsmentioning

confidence: 99%

Comprehensive Analysis of Mouse Bitter Taste Receptors Reveals Different Molecular Receptive Ranges for Orthologous Receptors in Mice and Humans

Lossow

Hübner

Roudnitzky

et al. 2016

Journal of Biological Chemistry

178

273

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“…The former yielded cascallin, cascarillone, cascarillins A-D, 13 cascarillins E-I, cascarilladione, eluterin K and pseudoeluterin B. 52 Fattorusso et al 53 isolated ten new clerodanes (eluterins A-J) from C.eluteria. The stem bark of C. urucurana yielded sonderianin, 27 15,16-epoxy-3,13(16)-clerodatriene-2-one and 12-epi-methyl-barbascoate.…”

Section: Diterpenesmentioning

confidence: 99%

Traditional uses, chemistry and pharmacology of Croton species (Euphorbiaceae)

Salatino¹,

Salatino²,

Negri³

2007

J. Braz. Chem. Soc.

377

317

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Croton é um gênero de Euphorbiaceae com cerca de 1300 espécies, amplamente distribuídas em regiões tropicais do Novo e Velho Mundos. Várias espécies há muito tempo desempenham papel importante nos usos tradicionais de plantas medicinais na África, Ásia e América do Sul. Tais usos incluem tratamento de câncer, constipação intestinal, diarréia e outros problemas digestivos, diabetes, feridas externas, febre, hipercolesterolemia, hipertensão, inflamação, vermes intestinais, malária, dor, úlceras e obesidade. Várias espécies de Croton têm um látex vermelho que contém, em algumas espécies, pró-antocianidinas e/ou alcalóides. Os alcalóides de Croton são a taspina ou substâncias relacionadas a benzilisoquinolinas. Os diterpenos são muito comuns em Croton, correspondendo a clerodanos, cembranóides, halimanos, cauranos, labdanos, ésteres do forbol, traquilobanos e sarcopetalanos. Algumas espécies são aromáticas, devido à presença de óleos voláteis. Representantes de novas classes de substâncias (fenilbutanóides, alcalóides glutarimidínicos e diterpenos sarcopetalanos) têm sido isoladas de espécies de Croton. Enquanto laticíferos têm sido descritos em espécies de Croton, até o momento não há estudos anatômicos sobre estruturas secretoras de óleos voláteis. Parece haver afinidades químicas no gênero relacionadas à geografia, agrupando espécies com (i) cauranos e/ou labdanos, (ii) traquilobanos e (iii) alcalóides. Os ensaios farmacológicos freqüentemente vêm corroborando os usos tradicionais de espécies de Croton. Grande parte dos ensaios farmacológicos trata do clerodano trans-desidrocrotonina, envolvendo uma grande diversidade de efeitos, incluindo hipolipidêmico, hipoglicêmico, antiestrogênico e anticâncer. Efeitos citotóxicos também vêm sendo observados em ensaios com alcalóides (taspina) e com diterpenóides secocaurenos, labdanos e cembranóides. Vários outros efeitos de substâncias de Croton têm sido relatados, incluindo anti-hipertensivos, antiinflamatórios, antimaláricos, antimicrobianos, antiespasmódicos, antiulcerogênicos, antivirais e mio-relaxantes.Croton is a genus of Euphorbiaceae comprising around 1,300 species, widespread in tropical regions of the Old and New Worlds. Several species have a long role in the traditional use of medicinal plants in Africa, Asia and South America. Popular uses include treatment of cancer, constipation, diabetes, digestive problems, dysentery, external wounds, fever, hypercholesterolemia, hypertension, inflammation, intestinal worms, malaria, pain, ulcers and weight-loss. Several species of Croton have a red sap, in some species containing proanthocyanidins and/or alkaloids. The latter may be taspine or some of several benzylisoquinoline-like compounds. Diterpenes are very common in Croton, corresponding to clerodanes, cembranoid, halimanes, kauranes, labdanes, phorbol esters, trachylobanes and sarcopetalanes. Some species are aromatic due to the possession of volatile oils. Representatives of new classes of compounds (phenylbutanoids, glutarimide alkaloids, sarcopetalane diterpen...

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“…O látex de Synandenium grantii, conhecido na Índia e no continente africano como "african milkbush", possui atividades antiinflamatória, analgésica e antitumoral (Duarte et al, 2010). Os diterpenos do tipo clerodano são os mais comuns em Croton, como por exemplo, a cascarilina e os furoclerodanos de C. eluteria, que conferem atividade analgésica, antiespasmódica e antitérmica, podendo ser utilizados como substituto de várias espéceis de Chinchona no tratamento da febre-terça decorrente da malária (Fattorusso et al, 2002). Os esteróides também são bastante relatados em euforbiáceas.…”

Section: As Euphorbiaceaeunclassified

“…Compostos considerados bioativos apresentam atividade insetífuga, antimicrobiana, antiviral, antiúlcera, gastroprotetora e antitumoral (Maciel et al, 1998;Fattorusso et al, 2002;Campos et al, 2010). Relatos sobre ocorrência de clerodanos em Croton (principalmente furano-clerodanos) são bastante comuns tendo registro em C. cajucara (Maciel et al, 1998;Grynberg et al, 1999;Souza et al, 2006;Campos et al, 2010), C. draco (Murillo et al, 2001;Deepika-Gupta et al, 2008), C. eluteria (Fattorusso et al, 2002), C lechleri (De Marino et al, 2008), C. membranaceous (Bayor et al, 2009), C. oblongifolius (Youngsa et al, 2007, C. palanostigma (Socorro et al, 2004;Brasil et al, 2009) e C. polyandrus (Araújo-Junior et al, 2005. Nos trabalhos realizados com C. cajucara, um dos diterpenos mais característico é a trans-crotonina, um furano-clerodano bioativo com atividades fungicida (Souza et al, 2006), anti-úlcera (Campos et al, 2010), antitumoral e anti-inflamatória (Grynberg et al, 1999).…”

Section: Fórmula MMunclassified

“…Em Croton são descritos para um grande número de espécies, como C. zambesicus (Mohamed et al, 2009), C. tiglium (Mendes et al, 2004), C. betulaster (Barbosa et al, 2003), C. eluteria (Fattorusso et al, 2002) e C. pulley (Abreu et al, 2001). Nas espécies analisadas foram detectadas em altas concentrações nos extratos metanólicos de folha de C. ericoides (13,5% do total de compostos identificados), C. dusenii (13,6%) e C. pallidulus var.…”

Section: Triterpenos E Esteróidesunclassified

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Análise de terpenóides de espécies de Croton sect. Lamprocroton (Mull. Arg.) Pax (Euphorbiaceae)

Feliu¹

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Diterpenoids from Cascarilla (Croton eluteriaBennet)

Cited by 17 publications

References 13 publications

Comprehensive Analysis of Mouse Bitter Taste Receptors Reveals Different Molecular Receptive Ranges for Orthologous Receptors in Mice and Humans

Comprehensive Analysis of Mouse Bitter Taste Receptors Reveals Different Molecular Receptive Ranges for Orthologous Receptors in Mice and Humans

Traditional uses, chemistry and pharmacology of Croton species (Euphorbiaceae)

Análise de terpenóides de espécies de Croton sect. Lamprocroton (Mull. Arg.) Pax (Euphorbiaceae)

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