Nortrachelogenin
(Synonyms: (-)-Wikstromol; (-)-Nortrachelogenin) 目录号 : GC63117Nortrachelogenin ((-)-Wikstromol) 可从 Partrinia scabiosaefolia 分离得到,可诱导 Candida albicans 的凋亡.
Cas No.:34444-37-6
Sample solution is provided at 25 µL, 10mM.
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Nortrachelogenin ((-)-Wikstromol) from Partrinia scabiosaefolia elicits an apoptotic response in Candida albicans[1].
[1]. Heejeong Lee, et al. (-)-Nortrachelogenin from Partrinia scabiosaefolia elicits an apoptotic response in Candida albicans. FEMS Yeast Res. 2016 May;16(3):fow013.
Cas No. | 34444-37-6 | SDF | |
别名 | (-)-Wikstromol; (-)-Nortrachelogenin | ||
分子式 | C20H22O7 | 分子量 | 374.38 |
溶解度 | 储存条件 | ||
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1 mg | 5 mg | 10 mg | |
1 mM | 2.6711 mL | 13.3554 mL | 26.7108 mL |
5 mM | 0.5342 mL | 2.6711 mL | 5.3422 mL |
10 mM | 0.2671 mL | 1.3355 mL | 2.6711 mL |
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2.
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Attenuating Effects of Nortrachelogenin on IL-4 and IL-13 Induced Alternative Macrophage Activation and on Bleomycin-Induced Dermal Fibrosis
J Agric Food Chem 2018 Dec 26;66(51):13405-13413.PMID:30458613DOI:10.1021/acs.jafc.8b03023.
Excessive alternative macrophage activation contributes to fibrosis. We studied the effects of Nortrachelogenin, the major lignan component of Pinus sylvestris knot extract, on alternative (M2) macrophage activation. J774 murine and THP-1 human macrophages were cultured with IL-4+IL-13 to induce alternative activation, together with the extract and its components. Effects of Nortrachelogenin were also studied in bleomycin-induced murine dermal fibrosis model. Knot extract significantly decreased the expression of alternative activation markers-arginase 1 in murine macrophages (97.4 ± 1.3% inhibition at 30 μg/mL) and CCL13 and PDGF in human macrophages-as did Nortrachelogenin (94.9 ± 2.4% inhibition of arginase 1 at 10 μM). Nortrachelogenin also decreased PPARγ expression but had no effect on STAT6 phosphorylation. In vivo, Nortrachelogenin reduced bleomycin-induced increase in skin thickness as well as the expression of collagens COL1A1, COL1A2, and COL3A1 (all by >50%). In conclusion, Nortrachelogenin suppressed IL-4+IL-13-induced alternative macrophage activation and ameliorated bleomycin-induced fibrosis, indicating therapeutic potential in fibrosing conditions.
Anti-inflammatory Effects of Nortrachelogenin in Murine J774 Macrophages and in Carrageenan-Induced Paw Edema Model in the Mouse
Planta Med 2017 Apr;83(6):519-526.PMID:27737478DOI:10.1055/s-0042-118188.
Nortrachelogenin is a pharmacologically active lignan found in knot extracts of Pinus sylvestris. In previous studies, some lignans have been shown to have anti-inflammatory properties, which made Nortrachelogenin an interesting candidate for our study. In inflammation, bacterial products and cytokines induce the expression of inducible nitric oxide synthase, cyclooxygenase-2, and microsomal prostaglandin E synthase-1. These enzymes synthesize factors, which, together with proinflammatory cytokines, are important mediators and drug targets in inflammatory diseases.The effects of Nortrachelogenin on the expression of inducible nitric oxide synthase, cyclooxygenase-2, and microsomal prostaglandin E synthase-1 as well as on the production of nitric oxide, prostaglandin E2, and cytokines interleukin-6 and monocyte chemotactic protein-1 were investigated in the murine J774 macrophage cell line. In addition, we examined the effect of Nortrachelogenin on carrageenan-induced paw inflammation in mice.Interestingly, Nortrachelogenin reduced carrageenan-induced paw inflammation in mice and inhibited the production of inflammatory factors nitric oxide, prostaglandin E2, interleukin-6, and monocyte chemotactic protein-1 in J774 macrophages in vitro. Nortrachelogenin inhibited microsomal prostaglandin E synthase-1 protein expression but had no effect on cyclooxygenase-2 protein levels. Nortrachelogenin also had a clear inhibitory effect on inducible nitric oxide synthase protein expression but none on its mRNA levels, and the proteasome inhibitor lactacystin reversed the effect of Nortrachelogenin on inducible nitric oxide synthase expression, suggesting a post-transcriptional mechanism of action.The results revealed hitherto unknown anti-inflammatory properties of Nortrachelogenin, which could be utilized in the development of anti-inflammatory treatments.
The antitumor lignan Nortrachelogenin sensitizes prostate cancer cells to TRAIL-induced cell death by inhibition of the Akt pathway and growth factor signaling
Biochem Pharmacol 2013 Sep 1;86(5):571-83.PMID:23747345DOI:10.1016/j.bcp.2013.05.026.
Prostate cancer cells frequently develop resistance toward androgen-deprivation and chemotherapy. To identify new approaches to treat androgen-dependent prostate cancer, we have performed a structure-activity analysis of lignan polyphenols for cancer cell specific sensitization to tumor necrosis factor-related apoptosis-inducing ligand (TRAIL), a death ligand that has ability to induce tumor-specific cell death. In this study, we report that the lignan Nortrachelogenin (NTG) is the most efficient of the 27 tested lignan compounds in sensitizing prostate cancer cells to TRAIL-induced apoptosis. Importantly, pretreatment with NTG does not sensitize a non-malignant prostate cell line to TRAIL-induced cell death. The structural comparison of lignans reveals that the dibenzylbutyrolactone skeleton is required for the apoptosis-sensitizing activity, while substitutions at the aromatic rings do not seem to play a critical role in this lignan function. Our study also characterizes the cellular effects and molecular mechanisms involved in NTG anticancer activity. We previously reported that specific lignans inhibit the Akt survival-signaling pathway in concert with TRAIL sensitization. While NTG is also shown to be a effective inhibitor of Akt signaling, in this study we further demonstrate that NTG potently inhibits tyrosine kinase (RTK) activation in response to growth factors, such as insulin and insulin-like growth factor I (IGF-I). Our results identify NTG as a novel agent for prostate cancer therapy with ability to inhibit Akt membrane localization and activity as well as the activation of growth factor receptors (GFRs), thereby efficiently synergizing with TRAIL exposure.
(+)Nortrachelogenin, a new pharmacologically active lignan from Wikstroemia indica
Lloydia 1979 Mar-Apr;42(2):159-62.PMID:449625doi
A new lignan, (+)-nortrachelogenin (I), and a known compound, daphnoretin were isolated from Wikstroemia indica C.A. Meyer (Thymelaeaceae). The structure of (+)-nortrachelogenin was established as 8(R)8'-4,4',8'-trihydroxy-3,3'-dimethoxylignan-olid, (9,9') on the basis of spectroscopic evidence and comparison with its enantiomer, (-)-nortrachelogenin. +-nortrachelogenin(I) showed effects on the central nervous system producing depression in rabbits.
Lignans from Trachelospermum jasminoides
Planta Med 2005 Jan;71(1):93-5.PMID:15678384DOI:10.1055/s-2005-837761.
Seven lignans having a diarylhydroxybutyrolactone skeleton were isolated from the leaves and stems of Trachelospermum jasminoides (Lindl.) Lem. Their structures were elucidated to be Nortrachelogenin 8' -O-beta-D-glucopyranoside (1), Nortrachelogenin 5'- C- beta-D-glucopyranoside (2), trachelogenin amide (3), nortracheloside, trachelogenin, tracheloside, and trachelogenin 4'- O- beta-gentiobioside, respectively, on the basis of spectroscopic analyses. Lignans 1 - 3 were structurally identified to be new compounds, and 2 was a rare C-glucosyl-lignan.