Cannabisin F
(Synonyms: 大麻酰胺F) 目录号 : GC62886Cannabisin F 是一种 SIRT1 调制器。Cannabisin F 作为大麻籽木素酰胺,可用于抗炎、抗氧化研究。Cannabisin F 作为SIRT1/NF-κB 和 Nrf2 的调节因子,可能是一种潜在的神经退行性疾病的调节剂。
Cas No.:163136-19-4
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Cannabisin F is a SIRT1 modulator. Cannabisin F, as a hempseed lignanamide, can be used for the research of anti-inflammatory and anti-oxidative. Cannabisin F may be a potential agent of neurodegenerative diseases as modulators of SIRT1/NF-κB and Nrf2[1].
Cannabisin F (0~15 μM; 1 hour; BV2 microglia cells) inhibits the phosphorylation of IκBα, p65, but enhances the expression of Nrf2 and HO-1[1].Cannabisin F (0~15 μM; 24 hours; BV2 microglia cells) has no significant effect on cell survival, inhibits IL-6 and TNF-α production and their mRNA expression, inhibits the production of ROS and increases the expression of SIRT1[1].
[1]. Wang S, et al. Cannabisin F from Hemp (Cannabis sativa) Seed Suppresses Lipopolysaccharide-Induced Inflammatory Responses in BV2 Microglia as SIRT1 Modulator. Int J Mol Sci. 2019;20(3):507. Published 2019 Jan 25.
Cas No. | 163136-19-4 | SDF | |
别名 | 大麻酰胺F | ||
分子式 | C36H36N2O8 | 分子量 | 624.68 |
溶解度 | 储存条件 | ||
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Cannabisin F from Hemp ( Cannabis sativa) Seed Suppresses Lipopolysaccharide-Induced Inflammatory Responses in BV2 Microglia as SIRT1 Modulator
Int J Mol Sci 2019 Jan 25;20(3):507.PMID:30691004DOI:10.3390/ijms20030507.
Hemp seed (Fructus cannabis) is rich in lignanamides, and initial biological screening tests showed their potential anti-inflammatory and anti-oxidative capacity. This study investigated the possible effects and underlying mechanism of Cannabisin F, a hempseed lignanamide, against inflammatory response and oxidative stress in lipopolysaccharide (LPS)-stimulated BV2 microglia cells. Cannabisin F suppressed the production and the mRNA levels of pro-inflammatory mediators such as interleukin 6 (IL-6) and tumor necrosis factor α (TNF-α) in a concentration-dependent manner in LPS-stimulated BV2 microglia cell. Furthermore, Cannabisin F enhanced SIRT1 expression and blocked LPS-induced NF-κB (Nuclear factor kappa B) signaling pathway activation by inhibiting phosphorylation of IκBα (Inhibit proteins of nuclear factor kappaB) and NF-κB p65. And the SIRT1 inhibitor EX527 significantly inhibited the effect of Cannabisin F on pro-inflammatory cytokines production, suggesting that the anti-inflammatory effects of Cannabisin F are SIRT1-dependent. In addition, Cannabisin F reduced the production of cellular reactive oxygen species (ROS) and promoted the expression of Nrf2 (Nuclear factor erythroid-2 related factor 2) and HO-1 (Heme Oxygenase-1), suggesting that the anti-oxidative effects of Cannabisin F are related to Nrf2 signaling pathway. Collectively, these results suggest that the neuro-protection effect of Cannabisin F against LPS-induced inflammatory response and oxidative stress in BV2 microglia cells involves the SIRT1/NF-κB and Nrf2 pathway.
Metabolites Identification of Bioactive Compounds Daturataturin A, Daturametelin I, N-Trans-Feruloyltyramine, and Cannabisin F From the Seeds of Datura metel in Rats
Front Pharmacol 2018 Jul 9;9:731.PMID:30050436DOI:10.3389/fphar.2018.00731.
Datura metel L. is a widely used traditional herbal medicine, and withanolides and amides are the two groups of main bioactive constituents in Datura metel seeds. This study aimed to elucidate the metabolism of four representative bioactive compositions containing daturataturin A (1), daturametelin I (2), N-trans-feruloyltyramine (3), and Cannabisin F (4) in rats. After separately oral administration of 20 mg/kg withanolides (1, 2) and amides (3, 4) to rats, a total of 12, 24, and 21 metabolites were detected in the plasma, urine, and fecal samples, respectively. Among them, three hydroxylated metabolites, 1-M3, 2-M2, and 3-M5, were detected in plasma and rat liver microsome incubation system in high abundance. Two metabolites of 1 and 2 were unambiguously identified by comparing with reference standards. Particularly, the methylated metabolite 27α-methoxy-(22R)-22,26-epoxy-27-[(β-D-glucopyranosyl)oxy]ergosta-2,4,6,24-tetraene-1,26-dione (daturametelin L) is a new compound. The withanolides could readily get hydroxylation or methylation metabolism. Meanwhile, the phase II metabolism (glucuronidation or sulfation) was the major reaction for the amides. This is the first study on in vivo metabolism of these active compounds in seeds of Datura metel.
Characterization of enantiomeric lignanamides from Solanum nigrum L. and their neuroprotective effects against MPP+-induced SH-SY5Y cells injury
Phytochemistry 2019 May;161:163-171.PMID:30661806DOI:10.1016/j.phytochem.2019.01.001.
Five pairs of enantiomeric lignanamides including nine undescribed compounds along with a known one were obtained from Solanum nigrum L. (Solanaceae). Their structures with absolute configurations were elucidated based on comprehensive spectroscopic analyses and quantum chemical calculations of electronic circular dichroism (ECD) curves. Additionally, all isolates were evaluated for their neuroprotective activity against MPP+ (1-methyl-4-phenylpyridinium)-induced SH-SY5Y cells injury. Among them, Cannabisin F showed the most significant neuroprotective effects at different concentrations (12.5, 25, 50 μM). Further studies by Hoechst 33258 staining, monodansylcadaverine (MDC) staining and Annexin V/PI analysis demonstrated that Cannabisin F could induce protective autophagy to protect SH-SY5Y cells from MPP+-induced apoptosis.
[Anti-complement alkaloids from whole plants of Viola yedoensis]
Zhongguo Zhong Yao Za Zhi 2017 Dec;42(24):4794-4800.PMID:29493149DOI:10.19540/j.cnki.cjcmm.20170928.012.
Fifteen alkaloids were isolated from the 95% ethanol extract of the whole plants of Viola yedoensis by various column chromatographic techniques such as silica gel and Sephadex LH-20. Their structures were identified as neoechinulin A(1),N-benzoyl-L-p-hydroxy-phenylalaninol(2),aurantiamide acetate(3),aurantiamide(4),anabellamide(5),trichosanatine(6),indole-3-carboxylic acid methyl ester(7),3-carboxyindole(8),N-trans-feruloyl-tyramine(9),paprazine(10),7'-(3', 4'-dihydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide(11),Cannabisin F(12),N-(4-hydroxyphenethyl)octacosanamide(13),N-(4-hydroxyphenethyl)hexacosanamide(14)and N-benzoyl-L-phenylalaninol(15). All the compounds except 3 and 4 were isolated from this plant for the first time. These alkaloids exhibited anti-complement activity against the classical pathway(CP)and the alternative pathway(AP)with the CH50 and AP50 values ranging from 0.12 to 0.33 g•L⁻¹ and 0.22 to 0.50 g•L⁻¹, respectively. Preliminary mechanism study using complement-depleted sera showed that these alkaloids acted on different complement components in the complement activation cascade.