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Demethylzeylasteral

Demethylzeylasteral
Names
Preferred IUPAC name
(2R,4aS,6aR,6aS,14aS,14bR)-9-formyl-10,11-dihydroxy-2,4a,6a,6a,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • InChI=1S/C29H36O6/c1-25-6-7-26(2,24(34)35)14-21(25)29(5)11-9-27(3)17-12-19(32)23(33)16(15-30)22(17)18(31)13-20(27)28(29,4)10-8-25/h12-13,15,21,32-33H,6-11,14H2,1-5H3,(H,34,35)/t21-,25-,26-,27+,28-,29+/m1/s1
    Key: ZDZSFWLPCFRASW-CPISFEQASA-N
  • C[C@]12CC[C@@](C[C@H]1[C@@]3(CC[C@]4(C5=CC(=C(C(=C5C(=O)C=C4[C@]3(CC2)C)C=O)O)O)C)C)(C)C(=O)O
Properties
C29H36O6
Molar mass 480.601 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Demethylzeylasteral is a naturally occurring organic compound with the formula C29H36O6. It is a pentacyclic triterpenoid compound isolated from the roots of Tripterygium wilfordii, a species of vine native to East and Southeast Asia commonly referred to as thunder god vine.

Isolation

Tripterygium wilfordii, also called as thunder god vine, is a perennial vine native to East and Southeast Asia, particularly in China, Korea, and Japan.[1] Demethylzeylasteral is typically isolated from the root xylem[2] or the skin of the vine's root.[1] It was reportedly first isolated in the 1990s by researchers at the Pharmaceutical Science Research Laboratory of Zhongshan Hospital, Fudan University in Shanghai.[3]

Structure and properties

Demethylzeylasteral is classified as a pentacyclic triterpenoid[1] with the molecular formula C29H36O6 and a molecular weight of 480.601 g/mol.[4] The compound appears as a yellow amorphous powder.[4] The pharmacologically active constituents of T. wilfordii include a diverse range of terpenoids, alkaloids, lignans, and diterpenes. Among these, triptolide and celastrol have been extensively studied for their potent biological activities.[5]

Applications

The therapeutic profile of T. wilfordii encompasses a broad range of indications, particularly within the framework of traditional medicine. It has long been employed to manage autoimmune and inflammatory disorders, with notable effectiveness in treating rheumatoid arthritis.[3] Other autoimmune conditions traditionally treated with this plant include systemic lupus erythematosus (SLE), autoimmune hepatitis, and ankylosing spondylitis.[6]

Renal diseases such as chronic nephritis, nephrotic syndrome, idiopathic IgA nephropathy, and diabetic nephropathy have also been addressed using preparations derived from T. wilfordii.[6] Additionally, the plant is utilized in the management of dermatological conditions, including psoriasis[6] and vitiligo.[6][7]

Within the theoretical framework of traditional Chinese medicine (TCM), T. wilfordii is said to promote blood circulation, unblock meridians, expel wind and dampness, and alleviate pain and swelling.[8] It has also been used to treat fever, edema, and carbuncles.[2]

References

  1. ^ a b c Sun, Xiaojing; Shen, Binyu; Yu, Hui; Wu, Wenhui; Sheng, Ruilong; Fang, Yiwen; Guo, Ruihua (2022-11-01). "Therapeutic potential of demethylzeylasteral, a triterpenoid of the genus Tripterygium wilfordii". Fitoterapia. 163 105333. doi:10.1016/j.fitote.2022.105333. ISSN 0367-326X. PMID 36244595.
  2. ^ a b Bai, Jun-Ping; Shi, Yu-Liang; Fang, Xin; Shi, Qi-Xian (2003-03-07). "Effects of demethylzeylasteral and celastrol on spermatogenic cell Ca2+ channels and progesterone-induced sperm acrosome reaction". European Journal of Pharmacology. 464 (1): 9–15. doi:10.1016/S0014-2999(03)01351-7. ISSN 0014-2999. PMID 12600689.
  3. ^ a b Wang, Yi; Zhao, Ban; Dang, Xin; Kong, Ling-Fei; Geng, Yi-Cong; He, Ping; Li, Zheng-Ying; Mao, Yong-hui; Tie, Cai (2024). "A novel SPE-LC-MRM strategy for serum demethylzeylasteral quantitation developed with an 18O-labeled internal standard". Analytical and Bioanalytical Chemistry. 416 (2): 467–474. doi:10.1007/s00216-023-05049-z. ISSN 1618-2642. PMID 37993551.
  4. ^ a b Xu, Wenping; Lin, Zongming; Yang, Chunxin; Zhang, Yongkang; Wang, Guomin; Xu, Xunhui; Lv, Qianzhou; Ren, Yushen; Dong, Ying (2009-07-01). "Immunosuppressive effects of demethylzeylasteral in a rat kidney transplantation model". International Immunopharmacology. 9 (7): 996–1001. doi:10.1016/j.intimp.2009.04.007. ISSN 1567-5769. PMID 19383554.
  5. ^ Lv, Linxi; Zhou, Feng; Quan, Yizhou; Fan, Yiwei; Bao, Yunjia; Dou, Yaning; Qu, Hongyan; Dai, Xuanxuan; Zhao, Haiyang; Zheng, Suqing; Zhao, Chengguang; Yang, Lehe (2024-08-01). "Demethylzeylasteral exerts potent efficacy against non-small-cell lung cancer via the P53 signaling pathway". Translational Oncology. 46 101989. doi:10.1016/j.tranon.2024.101989. ISSN 1936-5233. PMC 11141460. PMID 38781861.
  6. ^ a b c d Zhang, Kui; Fu, Gang; Pan, Guangzhao; Li, Chongyang; Shen, Li; Hu, Renjian; Zhu, Shunqin; Chen, Yibiao; Cui, Hongjuan (2018-10-10). "Demethylzeylasteral inhibits glioma growth by regulating the miR-30e-5p/MYBL2 axis". Cell Death & Disease. 9 (10): 1035. doi:10.1038/s41419-018-1086-8. ISSN 2041-4889. PMC 6180101. PMID 30305611.
  7. ^ Chang, Yuqian; Kang, Pan; Cui, Tingting; Guo, Weinan; Zhang, Weigang; Du, Pengran; Yi, Xiuli; Guo, Sen; Gao, Tianwen; Li, Chunying; Li, Shuli (2023-07-04). "Pharmacological inhibition of demethylzeylasteral on JAK-STAT signaling ameliorates vitiligo". Journal of Translational Medicine. 21 (1): 434. doi:10.1186/s12967-023-04293-2. ISSN 1479-5876. PMC 10318684. PMID 37403086.
  8. ^ Zhang, Yanqiong; Mao, Xia; Li, Weijie; Chen, Wenjia; Wang, Xiaoyue; Ma, Zhaochen; Lin, Na (2021). "Tripterygium wilfordii: An inspiring resource for rheumatoid arthritis treatment". Medicinal Research Reviews. 41 (3): 1337–1374. doi:10.1002/med.21762. ISSN 0198-6325. PMID 33296090.

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