Clerodane diterpenes of Croton hovarum

Krebs, Hans C.; Ramiarantsoa, Harisolo

doi:10.1016/s0031-9422(96)00815-1

Cited by 19 publications

(23 citation statements)

References 3 publications

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“…158 The 19- nor -clerodane 1063 with a C-5/C-10 double bond could be formed by a retro Diels–Alder reaction. 170 Except for an opened 17,12-γ-lactone ring and C-12 oxidation, compound 1064 from C. euryphyllus is quite structurally similar to 1070 and 1071 , which have a butenolide moiety spanning C-19 to C-6, from Teucrium viscidum . 278,382 Crassifolin H ( 1073 ) from C. crassifolius has a similar structure except for the presence of a C-5/C-10 rather than C-4/C-5 double bond.…”

Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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The clerodane diterpenoids are a widespread class of secondary metabolites and have been found in several hundreds of plant species from various families and in organisms from other taxonomic groups. These substances have attracted interest in recent years due to their notable biological activities, particularly insect antifeedant properties. In addition, the major active clerodanes of Salvia divinorum can be used as novel opioid receptor probes, allowing greater insight into opioid receptor-mediated phenomena, as well as opening additional areas for chemical investigation. This article provides extensive coverage of naturally occurring clerodane diterpenes discovered from 1990 until 2015, and follows up on the 1992 review by Merritt and Ley in this same journal. The distribution, chemotaxonomic significance, chemical structures, and biological activities of clerodane diterpenes are summarized. In the cases where sufficient information is available, structure activity relationship (SAR) correlations and mode of action of active clerodanes have been presented.

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Section: Structure Classifications and Sources Of Clerodane Diterpmentioning

confidence: 99%

Clerodane diterpenes: sources, structures, and biological activities

2016

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“…61 From leaves of plants of the same species, the clerodanes 3,12-dioxo-15,16-epoxy-cleroda-13(16),14-dien-9-al and 3α,4β-dihydroxy-15,16-epoxy-19-nor-12-oxo-cleroda-5(10),13(16),14-triene were isolated. 62 From leaves of C. zambesicus the trachylobane ent-trachyloban-3β-ol was obtained. 37 From the same source ent-18-hydroxy-trachyloban-3-one and the isopimarane-type diterpenoid isopimara-7,15-dien-3β-ol were also obtained.…”

Section: Diterpenesmentioning

confidence: 99%

“…24 From leaves of C. betulaster Müll. Arg., Barbosa et al 106 obtained 5-hydroxy,7,4'-dimethoxyflavone, and from leaves of C. hovarum Leandri, Krebs and Ramiarantsoa 62 isolated the flavone C-glycoside vitexin (21). From leaves and stems of C. brasiliensis, Palmeira et al 59 isolated the 3- 128 Flavonoid data is still too scarce to establish a pattern for Croton.…”

Section: Flavonoids and Other Phenolic Substancesmentioning

confidence: 99%

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

Salatino¹,

Salatino²,

Negri³

2007

J. Braz. Chem. Soc.

401

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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“…Phytochemical studies with Croton species revealed the presence of the flavonoids rutin and vitexin (Krebs and Ramiarantsoa, 1997;Capasso et al, 1998;Zou et al, 2010).…”

Section: Introductionmentioning

confidence: 99%