Cytotoxic labdane diterpenoids from Croton oblongifolius

Roengsumran, Sophon; Petsom, Amorn; Kuptiyanuwat, Narupat; Vilaivan, Tirayut; Ngamrojnavanich, Nattaya; Chaichantipyuth, Chaiyo; Phuthong, Songchan

doi:10.1016/s0031-9422(00)00358-7

Cited by 44 publications

(27 citation statements)

References 7 publications

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“…39 The labdanes from C. oblongifolius 2,3-dihydroxy-labda-8(17),12(E),14-triene showed non-specific, moderate, cytotoxicities against all the cell lines BT474, CHAGO, HEP-G2, KATO3 and SW620, whereas 2-acetoxy-3-hydroxy-labda-8(17),12(E),14-triene and 3-acetoxy-2-hydroxy-labda-8(17),12(E),14-triene were less active, because their ability to form hydrogen bond with certain receptors in tumor cells made them more selective but less active. 71 Also halimane and cembranoid diterpenes from C. oblongifolius showed antitumoral activity, but 12-benzoyloxycrotohalimaneic acid was inactive. 73 Neocrotocembranal (6) inhibited platelet aggregation induced by thrombin and exhibited cytotoxicity against P-338 cells in vitro.…”

Section: Anticancer T-dctnmentioning

confidence: 97%

“…From leaves of this species ent-7β-hydroxy-15-oxokaur-16-en-18-yl acetate 63 and ent-1α-acetoxy-7β,14α-dihydroxy-kaur-16-en-15-one 64 45 although it may be found also in the leaf chloroplasts of C. stellatopilosus Ohba. 67 C. oblongifolius has been a prolific source of diterpenoids, including: (i) the clerodane 11-dehydro (-) hardwickiic acid; 68 (ii) the labdanes labda-7,12(E),14-triene, labda-7,12(E),14-triene-17-al, labda-7,12(E),14-triene-17-ol, labda-7,12(E),14-triene-17-oic acid; 69 (iii) the cembranoid diterpenes crotocembranoic acid and neocrotocembranal 70 (6); (iv) the cytotoxic labdane diterpenoids 2-acetoxy-3-hydroxy-labda-8(17),12(E)-14-triene, 3-acetoxy-2-hydroxy-labda-8(17),12(E)-14-triene, and 2,3-dihydroxy-labda-8(17),12(E),14-triene were also isolated from the stem bark of C. oblongifolius; 71 (v) the labdane nidorellol, the furoclerodane croblongifolin and the clerodane crovatin; 72 (vi) the kaurane (-)ent-kaur-16-en-19-oic acid; 40 (vii) the halimanes crotohalimaneic acid (7), crotohalimoneic acid and 12-benzoyloxycrotohalimaneic acid; 73 (viii) new labdane-type diterpenoids 3-oxygenated ent-manoyl oxide derivatives with a 8,13-epoxytricyclic ring system and hydroxylabdandienes. 74 (-)-Hardwickiic acid (8) was isolated from C. californicus, 75 C. draco 33 and C. aromaticus L., a species with red latex native in Sri Lanka.…”

Section: Diterpenesmentioning

confidence: 99%

See 1 more Smart Citation

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

Salatino¹,

Salatino²,

Negri³

2007

J. Braz. Chem. Soc.

399

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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Section: Anticancer T-dctnmentioning

confidence: 97%

Section: Diterpenesmentioning

confidence: 99%

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

Salatino¹,

Salatino²,

Negri³

2007

J. Braz. Chem. Soc.

399

320

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“…Diterpenoids are important compounds that are known to demonstrate various bioactivities (Obatomi and Bach, 1998;Roengsumran et al, 2001). Recently, several natural diterpenoids have been studied and used in clinical therapy, such as paclitaxel, triptolide, and rographolide (Johnson, 1997;Tengchaisri et al, 1998).…”

Section: Introductionmentioning

confidence: 99%

The effects of oridonin on cell growth, cell cycle, cell migration and differentiation in melanoma cells

Ren

Wang

Xie

et al. 2006

Journal of Ethnopharmacology

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“…Compound 4 was inactive against all cell lines while compound 1 showed weak activity against gastric and colon adenocarcinoma and compound 2 showed weak activity against gastric and breast ductal carcinoma [139,140].…”

Section: Cytotoxic Activitiesmentioning

confidence: 99%

Labdanes of Natural Origin-Biological Activities (1981-2004)

Chinou

2005

CMC

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Terpenoids is a class of natural compounds found in higher plants, mosses, liverworts, algae and lichens, as well as in insects, microbes or marine organisms. Through centuries many of these compounds have been used as ingredients of perfumes, drugs, narcotics or pigments. Labdanes, belonging to the bicyclic diterpenoids group, have been found as secondary metabolites in tissues of fungi, insects, marine organisms, and in essential oils, resins and tissues of higher plants. The diterpenes of labdane type, have been reported to have broad spectrum of biological activities. In this study, the reported bioactivities and/or uses of them, the last two decades (1981-2004), are selected as an attempt to underline their role in nature.

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Cytotoxic labdane diterpenoids from Croton oblongifolius

Cited by 44 publications

References 7 publications

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

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

The effects of oridonin on cell growth, cell cycle, cell migration and differentiation in melanoma cells

Labdanes of Natural Origin-Biological Activities (1981-2004)

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