Minor Diterpenoids from Cascarilla (<i>Croton eluteria</i>Bennet) and Evaluation of the Cascarilla Extract and Cascarillin Effects on Gastric Acid Secretion

Appendino, Giovanni; Borrelli, Francesca; Capasso, Raffaele; Campagnuolo, Claudio; Fattorusso, Ernesto; Petrucci, Francesca; Taglialatela‐Scafati, Orazio

doi:10.1021/jf034780h

Cited by 13 publications

(10 citation statements)

References 9 publications

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“…8, Table S2 †). Compounds of this type have been isolated from plants of the families Euphorbiaceae, 44,78,105,107,109,[111][112][113][114][136][137][138][139][140][141][142][143][144][145][146][147][148][149][150][151] Compositae, 45 Annonaceae, 122 Lamiaceae, 91 Jungermanniaceae, 152,153 Asteraceae, 76 and Meliaceae, 154 and in sponges of genus Agelas. 79,135 Among them, chettaphanin II (102) 111 is found.…”

Section: Halim-5(10)-enes Groupmentioning

confidence: 99%

Halimane diterpenoids: sources, structures, nomenclature and biological activities

et al. 2018

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Covering: 1970 to 2017 Diterpenes with a halimane skeleton constitute a small group of natural products that can be biogenetically considered as being between labdane and clerodane diterpenoids. Some of these compounds show biological activities, such as antitumour, mosquito repellency, germination inhibition and antimicrobial, as well as being biomarkers for tuberculosis. To the best of our knowledge, there are no reviews on these compounds. In this review, halimane skeleton diterpenoids are classified according to their biogenetic origin, characterization and/or the enzymes involved in their biosynthesis. Herein, a review of their synthesis or synthetic approaches is communicated.

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Section: Halim-5(10)-enes Groupmentioning

confidence: 99%

Halimane diterpenoids: sources, structures, nomenclature and biological activities

et al. 2018

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“…141 The "sangre de grado" of C. lechleri has shown wound-healing activity 142 in cutaneous disorders and, orally, in a dilute form to facilitate the healing of gastric ulcers, reducing ulcer size and bacterial content of the ulcer. 143 The volatile oil from the bark of C. cajucara has been shown to exert gastric ulcer healing activity, as well as protection of the gastric mucosa.…”

Section: Wound Healing Gastric Effects and Protectionmentioning

confidence: 99%

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

Salatino¹,

Salatino²,

Negri³

2007

J. Braz. Chem. Soc.

396

320

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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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“…1 H-(500 MHz) and 13 C-NMR (125 MHz) spectra were measured on a Bruker AMX-500 spectrometer; chemical shifts are referenced to the residual solvent signal (CDCl 3 : d H = 7.26, d C = 77.0). The multiplicities of 13 C-NMR resonances were determined by DEPT experiments. One bond heteronuclear 1 H-13 C connectivities were determined with the HMQC experiment.…”

Section: General Experimental Proceduresmentioning

confidence: 99%

“…As a part of an ongoing research program aimed at the isolation, structural characterization, and pharmacological evaluation of bioactive plant secondary metabolites [11], [12], [13], [14], we have undertaken a phytochemical analysis of B. diffusa. Taking into account the use in folk medicine of B. diffusa for the treatment of intestinal disorders and the lack of experimental studies Isolation of New Rotenoids from Boerhaavia diffusa and Evaluation of their Effect on Intestinal Motility on this topic, we evaluated the effect of B. diffusa extracts on the contractions induced by exogenous acetylcholine in the isolated guinea-pig ileum.…”

Section: Introductionmentioning

confidence: 99%

Isolation of New Rotenoids fromBoerhaavia diffusaand Evaluation of their Effect on Intestinal Motility

et al. 2005

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A bioassay-guided separation of a methanolic extract obtained from the roots of Boerhaavia diffusa L. (Nyctaginaceae) allowed us to isolate five compounds belonging to the class of rotenoids: the known boeravinone D ( 1), boeravinone E ( 2), compound 5 and two novel compounds that we have named boeravinone G ( 3) and boeravinone H ( 4). The structures of the new molecules have been determined on the basis of their HR-EI-MS, (1)H- and (13)C-NMR and 2D-NMR (HMQC, HMBC) data. All the isolated rotenoids have been evaluated for their effect on intestinal motility in vitro. Three of them (boeravinone G, boeravinone E and compound 5) exhibited spasmolytic activity. Preliminary structure-activity relationships have been established highlighting the effect of substitutions on rings B and D.

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Minor Diterpenoids from Cascarilla (Croton eluteriaBennet) and Evaluation of the Cascarilla Extract and Cascarillin Effects on Gastric Acid Secretion

Cited by 13 publications

References 9 publications

Halimane diterpenoids: sources, structures, nomenclature and biological activities

Halimane diterpenoids: sources, structures, nomenclature and biological activities

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

Isolation of New Rotenoids fromBoerhaavia diffusaand Evaluation of their Effect on Intestinal Motility

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