Four previously undescribed diterpenoids including two crotofolanes, crotodichogamoin A and B, and two halimanes, crothalimene A and B, a new sesquiterpenoid, and fifteen previously reported compounds, including the crotofolane, crotohaumanoxide, the casbane, depressin, a further seven furanohalimane diterpenoids, three patchoulane and two further cadinane sesquiterpenoids and aleuritolic acid were isolated from the root of Croton dichogamus. Crotodichogamoin B is an important biosynthetic intermediate of the crotofolane class and this is the first report of patchoulene sesquiterpenoids from the genus. Compounds were tested at one concentration, 1 × 10 M, in the NCI59 cell one-dose screen but did not show significant activity snd were also evaluated for their cytotoxicity against Caco-2 cell lines using the neutral red assay. 10-epi-Maninsigin D reduced Caco-2 cell viability at 10, 30 and 100 μM, with values of decreased viability of 28%, 48% and 43% respectively. None of the other tested compounds showed significant activity.
The roots of the endangered medicinal plant Croton megalocarpoides collected in Kenya were investigated and twenty-two compounds isolated. Among them were twelve new ent-clerodane (1-12) and a new abietane (13) diterpenoids, alongside the known crotocorylifuran (4 a), two known abietane and four known ent-trachylobane diterpenoids, and the triterpenoids, lupeol and acetyl aleurotolic acid. The structures of the compounds were determined using NMR, HRMS and ECD. The isolated compounds were evaluated against a series of microorganisms (fungal and bacteria) and also against Plasmodium falciparum, however no activity was observed.
Two novel compounds, alienusolin, a 4α-deoxyphorbol ester (1), crotonimide C, a glutarimide alkaloid derivative (2), and ten known compounds, julocrotine (3), crotepoxide (4), monodeacetyl crotepoxide (5), dideacetylcrotepoxide, (6), β-senepoxide (7), α-senepoxide (8), (+)-(2S,3R-diacetoxy-1-benzoyloxymethylenecyclohex-4,6-diene (9), benzyl benzoate (10), acetyl aleuritolic (11), and 24-ethylcholesta-4,22-dien-3-one (12) were isolated from the Kenyan Croton alienus. The structures of the compounds were determined using NMR, GCMS, and HRESIMS studies.
Kenyan Croton sylvaticus Hochst. ex Krauss gave four clerodane diterpenoids, the new ent–3,13 E-clerodadiene-15-formate (1), the known 15-acetoxy- ent-3,13 E-clerodadiene (2), ent-3,13 E-clerodadien-15-ol (3) and hardwickiic acid (4), two known halimane diterpenoids, penduliflaworosin (5) and crotohalimaneic acid (6) and one labdane diterpenoid, labda-13 E-ene-8α,15-diol (7). The compounds, when tested for their anti-microbial activities against Bacillus subtilis, Xanthomonas campestris and Candida albicans, were found to be inactive.
Five previously undescribed compounds, megalocarpoidolide I (1), megalocarpoidolide J (3), 12-epi-crotonzambefuran A (4), megalocarpoidolide K (5), 1-trans-p-hydroxycoumaroylgeranylgerani-1-ol (6) were isolated from the stem bark of Croton megalocarpoides Friis & M. G. Gilbert. The known ent-trachyloban-18-ol, megalocarpoidolide B, megalocarpoidolide C (2), megalocarpoidolide H, crotocorylifuran, 7,8-dehydrocrotocorylifuran, 1,2dehydrocrotocorylifuran-2-one, acetyl aleuritolic acid, lupeol, N-trans-p-coumaroyl-3',4'dihydroxyphenylethylamine, dodecyl trans-ferulate and lignoceryl trans-ferulate were also isolated. The structures of the compounds were determined using NMR and IR spectroscopy and HRMS. The structure of compound 1 was determined using Logic for Structural Determination (LSD). Compounds 1, 2 and 3 were evaluated against the NCI60 panel of human tumour cell lines at 10µM level but found to be inactive.
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