Bioactive constituents from the leaves of Croton tiglium

Jiang, Zhi‐Yong; Duan, Li-Kun; Feng, Jin-E; Liu, Chunjiang; Li, Xiaofei; Li, Yuan; Huang, Chun-Qiu; Shi, Sheng-Li; Zuo, Ai‐Xue; He, Hongping

doi:10.1016/j.phytol.2022.03.003

Cited by 5 publications

(7 citation statements)

References 27 publications

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“…In addition, numerous phorbol esters have been isolated from the leaves and seed oil of Jatropha curcas L., which belongs to the same family as croton (Euphorbiaceae). 11–13…”

Section: Introductionmentioning

confidence: 99%

“…In addition, numerous phorbol esters have been isolated from the leaves and seed oil of Jatropha curcas L., which belongs to the same family as croton (Euphorbiaceae). [11][12][13] J. curcas is an energy crop which is capable of withstanding drought, and it contains high oil content in its seeds. However, the utilization of the seeds and seed oil is hindered by the presence of toxic phorbol esters, which would cause skin irritation and promote tumor growth.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and anti-leukemia activity of phorbol 13,20-diesters and phorbol 12,13,20-triesters

Wang

Feng

et al. 2023

Journal of Chemical Research

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Phorbol esters and their derivatives, such as TPA, have been reported as potential natural antitumor products, with some derivatives entering clinical research for leukemia treatment. In this study, 16 phorbol derivatives were synthesized from phorbol, and their anti-leukemia activity against Jurkat, HL-60, and K562 were tested. The results showed that several derivatives had anti-leukemia activity, with 5B demonstrating the strongest cytotoxic activity against the K562 cell line (IC50 = 0.24 ± 0.04 μM). Based on the IC50 values, a structure-activity relationship was established. When the substituent contained an aromatic group, phorbol derivatives esterified with long-chain organic acids at three reactive hydroxyl groups (C12-OH, C13-OH, and C20-OH) had better activity. When aryl groups were absent from the substituent groups, phorbol derivatives esterified with short-chain organic acids at two hydroxyl groups had better activity. Derivatives esterified with heterocyclic acids, either tri-substituted or di-substituted, showed a significant decrease in cytotoxicity. The mechanism of anti-leukemia activity was explored through flow cytometry, which indicated that phorbol esters inhibited the growth of leukemia cells by inducing apoptosis, leading to cell death. Molecular docking data of compound 5B docking to PKC δC1B suggested that substituent groups should not be too large, and caution should be taken when substituting C20-OH. Overall, these findings provide valuable insights into the design of more effective phorbol esters as anti-leukemia agents, but further research is needed to confirm their safety and efficacy in clinical settings.

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“…In addition, numerous phorbol esters have been isolated from the leaves and seed oil of Jatropha curcas L., which belongs to the same family as croton (Euphorbiaceae). 11–13…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and anti-leukemia activity of phorbol 13,20-diesters and phorbol 12,13,20-triesters

Wang

Feng

et al. 2023

Journal of Chemical Research

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“…[1,2] Several Croton species have played an important role in the traditional use of medicinal plants in Africa, Asia, and South America. [1,2] These medicinal Croton plants have been reported as a source of bioactive secondary metabolites such as clerodanes, [3][4][5][6] sesquiterpenoids, [7,8] diterpenoids, [9][10][11] alkaloids, [3,5] glycosides, [12] and pyran-2-one derivatives. [13,14] Some of these compounds exhibit a wide range of biological activities including antiinflammatory, [6,7] antibacterial, [4,11,13] anticancer, [4,5,9] and α-glucosidase inhibition.…”

Section: Introductionmentioning

confidence: 99%

“…[13,14] Some of these compounds exhibit a wide range of biological activities including antiinflammatory, [6,7] antibacterial, [4,11,13] anticancer, [4,5,9] and α-glucosidase inhibition. [10,14] Croton krabas is a shrub, 1-3 m in height, occurring in Thailand, Laos, and Cambodia. [15] This plant is commonly used as folk medicines for the treatment of digestive problems, body aches, and fever.…”

Section: Introductionmentioning

confidence: 99%

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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“…Our group investigated Croton spp. plants, including the leaves of C. damayeshu , C. tiglium , and C. yunnanensis . We observed that extracts of the roots of C. yunnanensis presented hypoglycemic activity in insulin-resistant (IR) 3T3-L1 adipocytes, distinctively from the bioactivity for the leaves of C. damayeshu , C. tiglium , and C. yunnanensis .…”

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confidence: 99%

In Vitro Hypoglycemic Diterpenoids from the Roots of Croton yunnanensis

et al. 2023

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Fifteen compounds including nine new diterpenes were isolated from the roots of Croton yunnanensis. By HRESIMS, NMR, ECD data, and X-ray diffraction analysis, the new compounds were characterized as eight neo-clerodane diterpenes (compounds 1−8) and one 15,16-dinor-ent-pimarane diterpene (9). All diterpenes were assayed for their hypoglycemic activities. Compounds 1−4, 6, 7, and 10 promoted glucose uptake activity in insulin-resistant 3T3-L1 adipocytes. Compounds 1 and 6 showed insulin sensitizing activity, potentiating conspicuously their glucose uptake activity at a concentration of 20 μM when treated synergistically with low-concentration insulin at 1 nM.

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Bioactive constituents from the leaves of Croton tiglium

Cited by 5 publications

References 27 publications

Synthesis and anti-leukemia activity of phorbol 13,20-diesters and phorbol 12,13,20-triesters

Synthesis and anti-leukemia activity of phorbol 13,20-diesters and phorbol 12,13,20-triesters

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

In Vitro Hypoglycemic Diterpenoids from the Roots of Croton yunnanensis

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