Diterpenoids from the seeds of Euphorbia lathyris and their effects on microglial nitric oxide production

Zuo, Quan; Mu, Huaiping; Gong, Qi; Ding, Xun; Wang, Wei; Zhang, Haiyan; Zhao, Weimin

doi:10.1016/j.fitote.2021.104834

Cited by 12 publications

(14 citation statements)

References 24 publications

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“…[18], was found to be inactive. In a recent study, Zuo et al evaluated the inhibitory activity against NO production induced by LPS in BV-2 microgial cell of twenty-one lathyrane diterpenoids [17]. Seventeen compounds, 43 (Figure 6), 74, 75 and 77 (Figure 8), 91 (Figure 13), 107-110 and 113 (Figure 18) and 118-125 (Figure 20), that demonstrated low cytotoxicity were found to be significantly active against LPS-induced NO overproduction in BV-2 microglial cells at 10 µM.…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

“…Structures 93 (Figure 13), 118 and 124 (Figure 20) were effective at the non-toxic concentration 1 µM, indicating that their effective concentration was lower than other tested compounds. Following the comparison of the activity shown by compounds 118, 124, 125 and EFL 2 (77) (Figure 20), which are isomeric compounds in C-9 or/and C-11, it can be deduced that the anti-inflammatory activity depends on the configurations at C-9 and C-11 [17]. A systematic study of the anti-inflammatory activity of different types of lathyrane has been carried out by Wang et.…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

“…Procedures describe their extraction at room temperature by maceration and isolation through multistep separation protocols [ 13 ]. Among the biological activities shown by this group of compounds, their capability to modulate MDR [ 14 ], their cytotoxicity against cancer cell lines [ 13 ], their anti-inflammatory activity [ 15 , 16 , 17 , 18 , 19 ] and their capability to induce proliferation or differentiation of NPC stand out with potential clinical application [ 4 , 5 , 20 ]. The relevance of the activities shown by these compounds, as well as their high content in natural sources, has allowed the development of libraries of compounds through molecular derivatization, these have been directed toward the evaluation of structure–activity relationships (SAR).…”

Section: Bioactive Lathyranesmentioning

confidence: 99%

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Pharmacological Potential of Lathyrane-Type Diterpenoids from Phytochemical Sources

et al. 2022

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Lathyrane diterpenoids are one of the primary types of secondary metabolites present in the genus Euphorbia and one of the largest groups of diterpenes. They are characterized by having a highly oxygenated tricyclic system of 5, 11 and 3 members. These natural products and some synthetic derivatives have shown numerous interesting biological activities with clinical potential against various diseases, such as cytotoxic activity against cancer cell lines, multi-drug resistance reversal, antiviral properties, anti-inflammatory activity and their capability to induce proliferation or differentiation into neurons of neural progenitor cells. The structure of the lathyrane skeleton could be considered privileged because its framework is able to direct functional groups in a well-defined space. The favorable arrangement of these makes interaction possible with more than one target. This review aims to highlight the evidence of lathyranes as privileged structures in medicinal chemistry. Chemical structures of bioactive compounds, the evaluation of biological properties of natural and semisynthetic derivatives, and the exploration of the mechanisms of action as well as target identification and some aspects of their targeted delivery are discussed.

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Section: Anti-inflammatory Activitymentioning

confidence: 99%

Section: Anti-inflammatory Activitymentioning

confidence: 99%

Section: Bioactive Lathyranesmentioning

confidence: 99%

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Pharmacological Potential of Lathyrane-Type Diterpenoids from Phytochemical Sources

et al. 2022

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“…It is used for the treatment of amenorrhea, edema, abdominal distension, constipation, oliguria, and anuria by oral administration, as well as for therapy for stubborn dermatophytoses and warts by external use on the skin [ 2 , 3 ]. In recent years, Euphorbia semen has been reported to have excellent pharmacological actions allowing it to inhibit adipogenesis, reverse tumor multidrug resistance, and treat terminal schistosomiasis, giving it the potential to be developed as a weight-loss and oncotherapy drug [ 4 , 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

Integrated Analysis of Transcriptome and microRNA Profile Reveals the Toxicity of Euphorbia Factors toward Human Colon Adenocarcinoma Cell Line Caco-2

et al. 2022

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Euphorbia factors, lathyrane-type diterpenoids isolated from the medical herb Euphorbia lathyris L. (Euphorbiaceae), have been associated with intestinal irritation toxicity, but the mechanisms underlying this phenomenon are still unknown. The objective of this study was to evaluate the transcriptome and miRNA profiles of human colon adenocarcinoma Caco-2 cells in response to Euphorbia factors L1 (EFL1) and EFL2. Whole transcriptomes of mRNA and microRNA (miRNA) were obtained using second generation high-throughput sequencing technology in response to 200 μM EFL treatment for 72 h, and the differentially expressed genes and metabolism pathway were enriched. Gene structure changes were analyzed by comparing them with reference genome sequences. After 72 h of treatment, 16 miRNAs and 154 mRNAs were differently expressed between the EFL1 group and the control group, and 47 miRNAs and 1101 mRNAs were differentially expressed between the EFL2 group and the control. Using clusters of orthologous protein enrichment, the sequenced mRNAs were shown to be mainly involved in transcription, post-translational modification, protein turnover, chaperones, signal transduction mechanisms, intracellular trafficking, secretion, vesicular transport, and the cytoskeleton. The differentially expressed mRNA functions and pathways were enriched in transmembrane transport, T cell extravasation, the IL-17 signaling pathway, apoptosis, and the cell cycle. The differentially expressed miRNA EFLs caused changes in the structure of the gene, including alternative splicing, insertion and deletion, and single nucleotide polymorphisms. This study reveals the underlying mechanism responsible for the toxicity of EFLs in intestinal cells based on transcriptome and miRNA profiles of gene expression and structure.

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“…Semen Euphorbiae (SE) consists of the dried seeds of Euphorbia lathyris L. It is a mildly poisonous traditional Chinese medicine that is used for its anti‐inflammatory properties and adjuvant antitumor support (Adolf & Hecker, 1971; Mesas et al, 2013; Zhang et al, 2018; Zuo et al, 2021). Medicinal chemistry studies have indicated that diterpenoids are the main active components, including L1, L2, L3, L7a, L7b, and L8 (Lee et al, 2015; Teng et al, 2018; Zhang et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Characterization of diterpene metabolism in rats with ingestion of seed products from Euphorbia lathyris L. (Semen Euphorbiae and Semen Euphorbiae Pulveratum) using UHPLC‐Q‐Exactive MS

Zhang

Jiang

Yue

et al. 2022

Biomedical Chromatography

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Previous pharmacological studies have indicated that diterpenoids are the primary effective chemical cluster in the seeds of Euphorbia lathyris L. The seed products are used in traditional Chinese medicine in the forms of Semen Euphorbiae (SE) and Semen Euphorbiae Pulveratum (SEP). However, the metabolism of the plant's diterpenoids has not been well elucidated, which means that the in vivo metabolite products have not been identified. The current study screened the physiological metabolites of six diterpenes [Euphorbia factor L 1 (L1), L 2 (L2), L 3 (L3), L 7a (L7a), L 7b (L7b), and L 8 (L8)] in feces and urine of rats after oral administration of SE and SEP using UHPLC-Q-Exactive MS. A total of 22 metabolites were detected in feces and 8 in urine, indicating that the major elimination route of diterpenoids is via the colon.Hydrolysis, methylation, and glucuronidation served as the primary metabolic pathways of these diterpenoids. In sum, this study contributed to the elucidation of new metabolites and metabolic pathways of SE and SEP, and the new chemical identities can be used to guide further pharmacokinetic studies.

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Diterpenoids from the seeds of Euphorbia lathyris and their effects on microglial nitric oxide production

Cited by 12 publications

References 24 publications

Pharmacological Potential of Lathyrane-Type Diterpenoids from Phytochemical Sources

Pharmacological Potential of Lathyrane-Type Diterpenoids from Phytochemical Sources

Integrated Analysis of Transcriptome and microRNA Profile Reveals the Toxicity of Euphorbia Factors toward Human Colon Adenocarcinoma Cell Line Caco-2

Characterization of diterpene metabolism in rats with ingestion of seed products from Euphorbia lathyris L. (Semen Euphorbiae and Semen Euphorbiae Pulveratum) using UHPLC‐Q‐Exactive MS

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