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Pachymic acid

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Pachymic acid
Names
IUPAC name 3β-(Acetyloxy)-16α-hydroxy-24-methylidenelanost-8-en-21-oic acid
Systematic IUPAC name (2R)-2-phenanthren-1-yl]-6-methyl-5-methylideneheptanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+Key: JNUUNUQHXIOFDA-XTDASVJISA-N
  • InChI=1S/C33H52O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h19,22,25-28,35H,3,10-18H2,1-2,4-9H3,(H,36,37)/t22-,25-,26+,27+,28+,31-,32-,33+/m1/s1Key: VDYCLYGKCGVBHN-DRCQUEPLSA-N
SMILES
  • CC(C)C(=C)CC(1(C2(1(CCC3=C2CC43(CC(C4(C)C)OC(=O)C)C)C)C)O)C(=O)O
Properties
Chemical formula C33H52O5
Molar mass 528.76 g/mol
Density 1.1±0.1 g/cm3
Boiling point 612.2±55.0 °C at 760 mmHg
Hazards
Flash point 184.7±25.0 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Pachymic acid is a naturally occurring steroid that can be extracted from the parasitic fungus Wolfiporia extensa (synonym Wolfiporia cocos). The dried sclerotia of the fungus is used as a traditional Chinese medicine, and pachymic acid is thought to be the principal bioactive component of it. Pachymic acid is a white powder that is not absorbed well by the body due the poor solubility it has in water.

Effects

Pachymic acid is known to inhibit the Epstein–Barr virus and to inhibit the snake venom phospholipase A2. It also has antitumor and anti-inflammatory properties. Pachymic acid anti-tumor properties are due to the cytotoxic effects it has on the tumors making them less viable and proliferate less. Various cancer cells can have their cell growth stopped and undergo apotosis, however the exact mechanism is not known.

References

  1. ^ Shu, Shaohua; Chen, Bei; Zhou, Mengchun; Zhao, Xinmei; Xia, Haiyang; Wang, Mo (2013). "De Novo Sequencing and Transcriptome Analysis of Wolfiporia cocos to Reveal Genes Related to Biosynthesis of Triterpenoids". PLOS ONE. 8 (8): e71350. Bibcode:2013PLoSO...871350S. doi:10.1371/journal.pone.0071350. PMC 3743799. PMID 23967197.
  2. ^ Wei, Chunyong; Wang, Hezhen; Sun, Xun; Bai, Zhixun; Wang, Jing; Bai, Guohui; Yao, Qizheng; Xu, Yingshu; Zhang, Lei (2022-07-01). "Pharmacological profiles and therapeutic applications of pachymic acid (Review)". Experimental and Therapeutic Medicine. 24 (3). doi:10.3892/etm.2022.11484. ISSN 1792-0981. PMC 9366251.
  3. "Pachymic acid Biological Test Results". PubChem compound database. 3 March 2016.
  4. Jiang, Feng; Zhu, Tieming; Yang, Chunfeng; Chen, Yang; Fu, Zhidong; Jiang, Lihui; Liu, Yongzhi (2023). "Pachymic Acid Inhibits Growth and Metastatic Potential in Liver Cancer HepG2 and Huh7 Cells". Biological and Pharmaceutical Bulletin. 46 (1): 35–41. doi:10.1248/bpb.b22-00440.
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