Tripterifordin
(Synonyms: 雷公藤福定) 目录号 : GC39111Tripterifordin 从 Tripterygium wilfordii 的根中分离出来,在 H9 淋巴细胞中具有显着的抗 HIV 复制活性,EC50 值为 3100 nM。
Cas No.:139122-81-9
Sample solution is provided at 25 µL, 10mM.
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Tripterifordin, isolated from the roots of Tripterygium wilfordii, possesses significant anti-HIV replication activities in H9 lymphocyte cells with an EC50 value of 3100 nM, respectively[1].
[1]. Kobayashi S, et al. Syntheses of (-)-Tripterifordin and (-)-Neotripterifordin from Stevioside.J Org Chem. 2018 Feb 2;83(3):1606-1613.
Cas No. | 139122-81-9 | SDF | |
别名 | 雷公藤福定 | ||
Canonical SMILES | C[C@@]12[C@]3([H])[C@@](COC1=O)(CCC2)[C@@]4([H])[C@]5(C[C@@]([C@](C)(O)C5)([H])CC4)CC3 | ||
分子式 | C20H30O3 | 分子量 | 318.45 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 3.1402 mL | 15.7011 mL | 31.4021 mL |
5 mM | 0.628 mL | 3.1402 mL | 6.2804 mL |
10 mM | 0.314 mL | 1.5701 mL | 3.1402 mL |
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Anti-AIDS agents, 4. Tripterifordin, a novel anti-HIV principle from Tripterygium wilfordii: isolation and structural elucidation
J Nat Prod 1992 Jan;55(1):88-92.PMID:1602302DOI:10.1021/np50079a013.
A new kaurane-type diterpene lactone, Tripterifordin [1], has been isolated from the roots of Tripterygium wilfordii. The structure of 1 was elucidated by spectroscopic methods, including the concerted application of a number of 2D nmr techniques that involved the 1H-1H COSY, heteronucleus-detected variants of the heteronuclear chemical shift correlation (HETCOR), phase-sensitive NOESY, and long-range HETCOR. Compound 1 shows anti-HIV replication activity in H9 lymphocyte cells with an EC50 of 1 microgram/ml.
Simultaneous determination of triptolide, Tripterifordin, celastrol and nine sesquiterpene alkaloids in Tripterygium preparations using high-performance liquid chromatography-triple quadrupole mass spectrometry
J Pharm Biomed Anal 2016 Jan 5;117:195-204.PMID:26363489DOI:10.1016/j.jpba.2015.08.043.
Tripterygium wilfordii tablet (TWT) and Tripterygium hypoglaucum tablet (THT), the preparations of the two Tripterygium herbs, are well known for the treatment of rheumatoid arthritis and other related inflammatory diseases clinically. In the present study, a high performance liquid chromatography (HPLC) coupled with electrospray ionization (ESI) tandem triple quadrupole mass spectrometry (QQQ/MS) method was developed for simultaneous quantification of 12 chemical components in Tripterygium preparations. The fragmentation patterns of analytes using ESI and collision-induced dissociation (CID) techniques were reported. This assay method was validated with respect to linearity (r(2)>0.9991), precision, repeatability, and accuracy (recovery rate between 97.2 and 104.2%). The proposed method was successfully applied for simultaneous quantification of the 12 compounds in Tripterygium preparations from the different manufactures. In addition, to evaluate the quality of Tripterygium preparations, partial least square discrimination analysis (PLS-DA) was performed to differentiate the contents of 12 compounds. In conclusion, the established HPLC/QQQ/MS method was proven to be useful and efficient for quality control of Tripterygium preparations.
T-96 attenuates inflammation by inhibiting NF-κB in adjuvant-induced arthritis
Front Biosci (Landmark Ed) 2020 Jan 1;25(3):498-512.PMID:31585899DOI:10.2741/4816.
The extract of the medicinal plant, Tripterygium wilfordii Hook. f. (TW), has been used in the treatment of diverse autoimmune diseases, including rheumatoid arthritis. However, the high frequency of toxic side effects has limited its clinical use. In order to reduce toxicity without losing the therapeutic benefit, the pharmacological activity and toxicity of four compounds (T-96, triptolide, neotripterifordin, and Tripterifordin) from TW were evaluated. The current study revealed that these compounds interfere with the IL-1β signaling pathway, which stimulates the secretion of pro-inflammatory cytokines (IL-6) in primary rheumatoid arthritis synovial fibroblasts (RASFs). These compounds inhibit IL-6 production, and among these, T-96 was the most effective. Moreover, T-96 blocks activation of NF-kappa B and p38 and ameliorates the joint destruction and the clinical signs of the disease in adjuvant-induced arthritic rats. These data suggest that among the four compounds of the TW, T-96 possesses highest anti-rheumatoid arthritis activity though inhibiting IL-1-mediated inflammatory signaling pathways.
[Effect of GR24 on accumulation of diterpenoids in Tripterygium wilfordii suspension cells]
Zhongguo Zhong Yao Za Zhi 2019 Aug;44(16):3582-3587.PMID:31602926DOI:10.19540/j.cnki.cjcmm.20190605.502.
Terpenoids are main bioactive components in Tripterygium wilfordii,but the contents of some terpenoids are relatively low. In order to provide scientific evidence for the regulation of terpenoids in T. wilfordii,this research explored the effect of GR24 on accumulations of four diterpenoids( triptolide,Tripterifordin,triptophenolide,and triptinin B) in T. wilfordii suspension cells by biological technology and UPLC-QQQ-MS/MS. The results indicated that 100 μmol·L-1 GR24 inhibited the accumulations of triptolide,Tripterifordin,triptophenolide,and triptinin B to different degrees. Compared with the control group,the contents of 4 diterpenoids( in the induced group) were down to 96.59%,63.80%,61.02% and 33.59% in 240 h,respectively. Among them,the accumulation of triptinin B iswas significantly inhibited. In addition,the key time point of inhibitory effect was 120 h after induction with GR24 in some diterpenoids. This is the first systematic study focusing on the effect of GR24 on the accumulations of diterpenoids in T. wilfordii suspension cells. The dynamic accumulation ruleregularity of four diterpenoids after induced by GR24 was summarized,which laid a foundation for further study on the chemical response mechanism of terpenoids to GR24.
Immunosuppressive diterpenoids from Tripterygium wilfordii
J Nat Prod 1999 Nov;62(11):1522-5.PMID:10579865DOI:10.1021/np9902183.
A clinically used extract of Tripterygium wilfordii afforded three new diterpenoids-3beta,19-dihydroxyabieta-8,11,13-triene (triptobenzene L) (1); 12,19-dihydroxy-3-oxoabieta-8,11,13-triene (triptobenzene M) (2); and 19-hydroxy-3,7-dioxo-abieta-8,11, 13-triene (triptobenzene N) (3)-along with 14 known diterpenoids. The structures of 1-3 were established on the basis of spectroscopic studies. Of the known compounds, the stereochemistry at C-4 of triptonediol (4) was reassigned. Tripterifordin (8) and 13-epi-manoyl oxide-18-oic acid (9) showed significant inhibitory effects on cytokine production.