Demethylzeylasteral

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
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).
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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

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