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Euphol

From Wikipedia, the free encyclopedia
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 mass426.729 g·mol−1
Densityg/cm3
Melting point116 °C (241 °F; 389 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Euphol is a tetracyclictriterpene with the molecular formulaC30H50O.[1]

Natural occurrence

[edit]

Euphol was isolated from cucumber and is an active principle of various plant species belonging to theEuphorbia genus.[2]

Uses

[edit]

The compound is known for its potentialhypotensive,anti-inflammatory, andantitumor activities.[3][4][5]

References

[edit]
  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. Retrieved22 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. Retrieved22 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. Retrieved22 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.
Types ofterpenes andterpenoids (# ofisoprene units)
Basic forms:
  • Acyclic (linear,cis andtrans forms)
  • Monocyclic (single ring)
  • Bicyclic (2 rings)
  • Iridoids (cyclopentane ring)
  • Iridoid glycosides (iridoids bound to a sugar)
  • Steroids (4 rings)
Hemiterpenoids (1)
Monoterpenes
(C10H16)(2)
Acyclic
Monocyclic
Bicyclic
Monoterpenoids
(2,modified)
Acyclic
Monocyclic
Bicyclic
Sesquiterpenoids (3)
Diterpenoids (4)
Acyclic
Monocyclic
Bicyclic
Tricyclic
Tetracyclic
Resin acids
Sesterterpenoids (5)
  • Geranylfarnesol
Triterpenoids (6)
Steroids
Other
Sesquarterpenes/oids (7)
  • Ferrugicadiol
  • Tetraprenylcurcumene
Tetraterpenoids
(Carotenoids) (8)
Carotenes
Xanthophylls:
Polyterpenoids (many)
Norisoprenoids (modified)
  • 3-oxo-α-ionol
  • 7,8-dihydroionone
Synthesis
Activated isoprene forms
Classes
Antibiotics
Antidepressants
(TeCAs)
Steroids
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