Bioactive diterpenoids from Croton laevigatus

Zhang, Junsheng; Tang, Ya-Qi; Huang, Jia-Luo; Li, Wei; Zou, Yi-Hong; Liu, Bo; Yin, Sheng

doi:10.1016/j.phytochem.2017.09.003

Cited by 20 publications

(32 citation statements)

References 25 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%

“…44 Crolaevinoids A-B (128-129) and crothalimene A (130) were recently isolated from Croton laevigatus and Croton dichogamus, respectively. 105,148 They are the only C17 functionalized derivatives known in this class forming a d-lactone with carbon C12. The absolute conguration of compounds 128 and 129 was determined by electronic circular dichroism (ECD).…”

Section: Halim-5(10)-enes Groupmentioning

confidence: 99%

“…These compounds exhibit pronounced inhibition of nitric oxide (NO) production. 105 3a-Hydroxy-5(10)-didehydrochiliolide (139) was highly active against a human pancreatic adenocarcinoma cell line at micromolar concentrations 45 and 140 shows antitumour activity. 76 Formosin A-C (135-137) isolated from Excoecaria formosana were active as antimicrobials, 147 and, in addition to crassifolius B (138), 150 they are the only compounds that possess a carboxylic acid or methyl ester functionality at C20.…”

Section: Halim-5(10)-enes Groupmentioning

confidence: 99%

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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%

Section: Halim-5(10)-enes Groupmentioning

confidence: 99%

Section: Halim-5(10)-enes Groupmentioning

confidence: 99%

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Halimane diterpenoids: sources, structures, nomenclature and biological activities

et al. 2018

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“…The IR absorption bands revealed the presence of OH (3471 cm −1 ) and carbonyl (1729 cm −1 ) groups. The 1 H and 13 As six of the ten degrees of unsaturation were accounted for by one ketone, three carbonyls, and two double bonds, the remaining degrees of unsaturation required that 1 be tetracyclic. The abovementioned data were quite similar to that of the known ingenane diterpenoid 5,20-O-diacetyl-3-O-(2,3-dimethylbutanoyl)-13-Ododecanoylingenol [15], except for the absence of an acetyl group and an upfield-shifted signal [δ H 3.87 (1H, d, J = 6.5 Hz)], indicating that 1 was a deacetylated derivative of the previously described compound.…”

Section: Resultsmentioning

confidence: 99%

“…In our continuing efforts toward discovering structurally intriguing anti-inflammatory substances from Euphorbiaceae plants [13,14], two new ingenane diterpenoids and sixteen analogues were isolated from the roots of E. kansui. These compounds were screened for anti-inflammatory activity by using the lipopolysaccharide (LPS)-induced NO production model, and the action mechanism of the active compounds was further explored.…”

Section: Introductionmentioning

confidence: 99%

Anti-inflammatory Ingenane Diterpenoids from the Roots of Euphorbia kansui

et al. 2018

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Bioassay-guided fractionation of the ethanolic extract of the roots of led to the isolation of two new ingenane diterpenoids, euphorkans A (1: ) and B (2: ), together with 16 known analogues (3: - 18: ). Their structures were determined by combined spectral and chemical methods. All the isolates were evaluated for their inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophage cells. Compounds 1: - 6: and 10: - 13: exhibited pronounced inhibitory activity with IC values in the range of 2.78 - 10.6 µM, and were more potent than the positive control, quercetin (IC = 15.8 µM). Compounds 1: and 5: were selected for further assays toward the key inflammation mediators TNF- and IL-6, and showed a significant inhibition in a dose-dependent manner. The preliminary mechanistic study revealed that 1: and 5: inhibited NF-B activity, which may exert a role in their anti-inflammatory activity.

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A New Clerodane from the Leaves of Croton krabas and Its Cholinesterase Inhibitory Activities

Linphosan,

Uk‐at,

Setsuwan

et al. 2023

Chemistry & Biodiversity

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Chromatographic separation of the leaves of Croton krabas resulted in the isolation of one new clerodane, crotoeurin D (1), along with two known compounds, 6S‐crotoeurin C (2) and blumenol A (3). Their structures were determined based on extensive nuclear magnetic resonance spectroscopic data analysis and mass spectrometry. The absolute configuration of the new clerodane was assigned by nuclear overhauser effect spectroscopy correlations and electronic circular dichroism calculations. Compound 1 exhibited significant acetylcholinesterase and butyrylcholinesterase inhibitory activities. Moreover, the binding modes of 1 revealed that its structure formed strong hydrogen bonds and hydrophobic interactions with the active sites of both enzymes.

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Bioactive diterpenoids from Croton laevigatus

Cited by 20 publications

References 25 publications

Halimane diterpenoids: sources, structures, nomenclature and biological activities

Halimane diterpenoids: sources, structures, nomenclature and biological activities

Anti-inflammatory Ingenane Diterpenoids from the Roots of Euphorbia kansui

A New Clerodane from the Leaves of Croton krabas and Its Cholinesterase Inhibitory Activities

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