Cembranolides from the stem bark of the southern African medicinal plant, Croton gratissimus (Euphorbiaceae)

Mulholland, Dulcie A.; Langat, Moses K.; Crouch, Neil R.; Coley, Helen M.; Mutambi, Emily M.; Nuzillard, Jean‐Marc

doi:10.1016/j.phytochem.2010.05.014

Cited by 41 publications

(49 citation statements)

References 20 publications

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“…15 Hz) common in the series isolated from the bark and leaves of the same species indicated that H-10 is β in all the compounds isolated. 7 The H-10 resonance showed correlations in the NOESY spectrum with H-11 and the H 3 -19 proton resonances, showing that both are on the β-face of the molecule, as illustrated in Figure 1. The conformation adopted by the molecule results in substituents attached to sp 2 carbons, pointing above or below the general plane of the molecule.…”

Section: Resultsmentioning

confidence: 90%

“…These were obtained together with six known compounds, eudesm-4(15)-ene-1β,6α-diol, 8 α-glutinol, 9 lupeol, 10 (+)-(1R*,4S*,10R*)-4-hydroxycembra-2E,7E,11Z-trien-20,10-olide (4a), and (+)-(1R*,10R*)-cembra-2E,4E,7E,11Z-tetraen-20,10-olide, which have been isolated previously from the bark of this species, 7 and 24-ethylcholesta-4,22-dien-3-one. 11 NMR analysis showed that purified cembranolides are unstable on standing, but appear to be stable in the unpurified form.…”

Section: Resultsmentioning

confidence: 99%

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Cembranolides from the Leaves of Croton gratissimus

et al. 2011

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20,10-olide (4a), have been isolated from the leaves of Croton gratissimus. The acetyl derivatives of 8 and 4a were evaluated against a chloroquine-sensitive strain of Plasmodium falciparum (D10).Croton gratissimus Burch. (C. zambesicus Mull. Arg.; C. microbotryus Pax.) (Euphorbiaceae) grows on stony hillsides as a semideciduous tree species throughout much of the warmer and drier regions from South Africa, northeastwards, to the horn of Africa. The leaves of this plant are ground with goat fat and those of two other Croton species, the resulting paste is heated on coals, and the fumes are inhaled as a cure for insomnia. 1 A tea made from the leaves is taken for coughs in Botswana. 2 Watt and Breyer-Brandwijk 3 documented C. gratissimus as a remedy for fever, for treating bleeding gums and eye disorders, and as an ingredient used to "smoke" rheumatic patients. In South Africa, the leaves are dried and smoked for influenza, colds, and fevers. 4 The traditional use of this species for treating fevers, intermittent or otherwise, indicates its likely application as an antimalarial, since it is employed as such within the malaria endemic region of southern Africa. In Nigeria, bark infusions of the species (as C. zambesicus) are reported to treat malaria. 5 Accordingly, crude dichloromethane extracts of South African leaves of C. gratissimus have previously been investigated for antiplasmodial activity in vitro and shown to have an IC 50 value of 3.5 μg/mL; 6 the constituent(s) responsible were not identified. The stem bark of C. gratissimus has been reported to yield four cembranoids, namely, (+)-(1R*,2S*,7S*,8S*,12R*)-7,8-epoxy-2,12-cyclocembra-3E,10Z-dien-20,10-olide, (+)-(1R*,10R*)c e m b r a -2 E , 4 E , 7 E , 1 1 Z -t e t r a e n -2 0 , 1 0 -o l i d e , (+)-(1R*,4S*,10R*)-4-hydroxycembra-2E,7E,11Z-trien-20,10-olide (4a), and (−)-(1R*,4R*,10R*)-4-hydroxycembra-2E,7E,11Z-trien-20,10-olide, in addition to lupeol, 4(15)eudesmene-1β,6α-diol, and α-glutinol.7

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Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Cembranolides from the Leaves of Croton gratissimus

et al. 2011

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“…33 Estudos prévios sobre a Croton gratissimus focaram-se sobre as folhas. 3,7 Foram identificadas principalmente cembranolidas, 2,3 trachilobanos e isopimaranos, 6,7 e na casca do caule, da qual foram isolados clerodanos e trachilobanos. 2,6 Este é o primeiro estudo sobre a composição química de flores, caules e folhas da Croton gratissimus.…”

Section: Resultsunclassified

“…encontra-se na África subsariana, crescendo em encostas rochosas das regiões quentes e secas do noroeste da África do Sul até ao Corno de África. 2,3 Todas as partes da C. gratissimus são usadas para fins medicinais. As folhas são aromáticas e frequentemente utilizadas como infusões para tratar a tosse e a febre.…”

Section: Introductionunclassified

“…As combinações da raiz e da casca são usadas para tratar distúrbios respiratórios. 2,4 Estudos anteriores sobre a composição química da C. gratissimus revelaram a presença de cembranolidas, lupeol, α-glutinol e 4(15)-eudesmeno-1β,6α-diol na casca do caule, 2 e cembranolidas, lupeol, α-glutinol e 24-etilcolesta-4,22-dien-3-ona, 3 kaempferol--3-O-β-6''(p-coumaroil) glucopiranosídeo (tilirosida), apigenina-6-C--glucosídeo (isovitexina) e kaempferol 5 …”

Section: Introductionunclassified

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Composição química de uma população de Croton gratissimus Burch (Euphorbiaceae)

et al. 2017

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Computer‐aided Dereplication and Structure Elucidation of Natural Products at the University of Reims

Bakiri

Plainchont

Emerenciano

et al. 2017

Molecular Informatics

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Natural product chemistry began in Reims, France, in a pharmacognosy research laboratory whose main emphasis was the isolation and identification of bioactive molecules, following the guidelines of chemotaxonomy. The structure elucidation of new compounds of steadily increasing complexity favored the emergence of methodological work in nuclear magnetic resonance. As a result, our group was the first to report the use of proton-detected heteronuclear chemical shift correlation spectra for the computer-assisted structure elucidation of small organic molecules driven by atom proximity relationships and without relying on databases. The early detection of known compounds appeared as a necessity in order to deal more efficiently with complex plant extracts. This goal was reached by an original combination of mixture fractionation by centrifugal partition chromatography, analysis by C NMR, digital data reduction and alignment, hierarchical data clustering, and computer database search.

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Cembranolides from the stem bark of the southern African medicinal plant, Croton gratissimus (Euphorbiaceae)

Cited by 41 publications

References 20 publications

Cembranolides from the Leaves of Croton gratissimus

Cembranolides from the Leaves of Croton gratissimus

Composição química de uma população de Croton gratissimus Burch (Euphorbiaceae)

Computer‐aided Dereplication and Structure Elucidation of Natural Products at the University of Reims

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