Chemistry:Demethylzeylasteral

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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. ↑ 1.0 1.1 1.2 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. doi:10.1016/j.fitote.2022.105333. ISSN 0367-326X. PMID 36244595. 
  2. ↑ 2.0 2.1 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. ↑ 3.0 3.1 Wang, Yi; Zhao, Ban; Dang, Xin; Kong, Ling-Fei; Geng, Yi-Cong; He, Ping; Li, Zheng-Ying; Mao, Yong-hui et al. (2024). "A novel SPE-LC-MRM strategy for serum demethylzeylasteral quantitation developed with an 18O-labeled internal standard" (in en). Analytical and Bioanalytical Chemistry 416 (2): 467–474. doi:10.1007/s00216-023-05049-z. ISSN 1618-2642. PMID 37993551. 
  4. ↑ 4.0 4.1 Xu, Wenping; Lin, Zongming; Yang, Chunxin; Zhang, Yongkang; Wang, Guomin; Xu, Xunhui; Lv, Qianzhou; Ren, Yushen et al. (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 et al. (2024-08-01). "Demethylzeylasteral exerts potent efficacy against non-small-cell lung cancer via the P53 signaling pathway". Translational Oncology 46. doi:10.1016/j.tranon.2024.101989. ISSN 1936-5233. PMID 38781861. 
  6. ↑ 6.0 6.1 6.2 6.3 Zhang, Kui; Fu, Gang; Pan, Guangzhao; Li, Chongyang; Shen, Li; Hu, Renjian; Zhu, Shunqin; Chen, Yibiao et al. (2018-10-10). "Demethylzeylasteral inhibits glioma growth by regulating the miR-30e-5p/MYBL2 axis" (in en). Cell Death & Disease 9 (10): 1035. doi:10.1038/s41419-018-1086-8. ISSN 2041-4889. PMID 30305611. 
  7. ↑ Chang, Yuqian; Kang, Pan; Cui, Tingting; Guo, Weinan; Zhang, Weigang; Du, Pengran; Yi, Xiuli; Guo, Sen et al. (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. 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" (in en). Medicinal Research Reviews 41 (3): 1337–1374. doi:10.1002/med.21762. ISSN 0198-6325. PMID 33296090. 



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