Euphol

Euphol
Names
IUPAC name
(3S,5R,10S,13S,14S,17S)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Other names
Euphadienol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22+,25+,26+,28-,29+,30-/m1/s1
    Key: CAHGCLMLTWQZNJ-WZLOIPHISA-N
  • C[C@H](CCC=C(C)C)[C@@H]1CC[C@]2([C@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C
Properties
C30H50O
Molar mass 426.729 g·mol−1
Density g/cm3
Melting point 116 °C (241 °F; 389 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Euphol is a tetracyclic triterpene with the molecular formula C30H50O.

Natural occurrence

Euphol was isolated from cucumber and is an active principle of various plant species belonging to the Euphorbia genus.

Uses

The compound is known for its potential hypotensive, anti-inflammatory, and antitumor activities.

References

  1. ↑ Shaban, Aya Fadle; Abd El Kawy, Mostafa A.; Hamed, Ahmed Ragab; Salama, Abeer; El Motayam, Amira Kamal (1 June 2025). "Euphol: chemical and biological aspects: A review". Egyptian Journal of Chemistry. 68 (6): 705–726. doi:10.21608/ejchem.2024.322067.10466. ISSN 0449-2285. Retrieved 22 July 2025.
  2. ↑ Silva, Viviane A. O.; Rosa, Marcela N.; Miranda-Gonçalves, Vera; Costa, Angela M.; Tansini, Aline; Evangelista, Adriane F.; Martinho, Olga; Carloni, Adriana C.; Jones, Chris; Lima, João Paulo; Pianowski, Luiz F.; Reis, Rui Manuel (April 2019). "Euphol, a tetracyclic triterpene, from Euphorbia tirucalli induces autophagy and sensitizes temozolomide cytotoxicity on glioblastoma cells". Investigational New Drugs. 37 (2): 223–237. doi:10.1007/s10637-018-0620-y. hdl:1822/57883. ISSN 1573-0646. PMID 29931585.
  3. ↑ Zhao, Maoyuan; Yang, Yi; Nian, Qing; Shen, Caifei; Xiao, Xiaolin; Liao, Wenhao; Zheng, Qiao; Zhang, Gang; Chen, Nianzhi; Gong, Daoyin; Tang, Jianyuan; Wen, Yueqiang; Zeng, Jinhao (1 February 2023). "Phytochemicals and mitochondria: Therapeutic allies against gastric cancer". Phytomedicine. 110 154608. doi:10.1016/j.phymed.2022.154608. ISSN 0944-7113. PMID 36586205. Retrieved 22 July 2025.
  4. ↑ Singh, G. B.; Singh, Surjeet; Sharma, M. L.; Suri, O. P.; Chopra, C. L.; Ammon, H. P. T. (December 1989). "Hypotensive Activity of 8,24-Euphadien-3β-ol (Euphol)". Planta Medica. 55 (6): 498–500. Bibcode:1989PlMed..55..498S. doi:10.1055/s-2006-962079. ISSN 0032-0943. PMID 2616667. Retrieved 22 July 2025.
  5. ↑ Cruz, L. S.; De Oliveira, T. L.; Kanunfre, C. C.; Paludo, K. S.; Minozzo, B. R.; Prestes, A. P.; Wang, M.; Fernandes, D.; Santos FAD; Manda, V. K.; Khan, S. I.; Ali, Z.; De Messias-Reason, I. J.; Avula, B.; Khan, I. A.; Beltrame, F. L. (2018). "Pharmacokinetics and cytotoxic study of euphol from Euphorbia umbellata (Bruyns) Pax latex". Phytomedicine. 47: 105–112. doi:10.1016/j.phymed.2018.04.055. PMID 30166094. S2CID 52132966.