French
DeutschCycloeucalenol
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| Names | |
|---|---|
| IUPAC name (3β,4α,5α,9β)-4,14-Dimethyl-9,19-cycloergost-24(28)-en-3-ol | |
| Other names 3beta-Cycloeucalenol | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| KEGG | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| C30H50O | |
| Molar mass | 426.729 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Cycloeucalenol is a 3β-sterol, a pentacyclic triterpenoid and a member of phytosterols group.[1][2] The compound derives from a hydride of a 5α-ergostane.
Natural occurrence
[edit]Cycloeucalenol is a naturally occurring triterpenoid and a sterol-like compound found in certain plants[3][4] (i.e. Boophone disticha,[5] Herissanthia tiubae,[6] etc.) and microorganisms. It is classified as a cycloartane-type triterpenoid, a subgroup of terpenoids characterized by a cyclopropane ring in their structure. Cycloeucalenol is an intermediate in the biosynthesis of phytosterols, which are essential components of plant cell membranes.[7]
Biosynthesis
[edit]Cycloeucalenol is derived from cycloartenol, a key precursor in the phytosterol biosynthetic pathway. The conversion involves enzymatic modifications, including the opening of the cyclopropane ring and subsequent rearrangements.[8]
References
[edit]- ^ Heintz, R.; Bimpson, T.; Benveniste, P. (1 November 1972). "Plant sterol metabolism studies on the substrate specificity of an enzyme capable of opening the cyclopropane ring of cycloeucalenol". Biochemical and Biophysical Research Communications. 49 (3): 820–826. Bibcode:1972BBRC...49..820H. doi:10.1016/0006-291X(72)90484-6. ISSN 0006-291X. PMID 4638757. Retrieved 20 July 2025.
- ^ Chopra, R. N. (2005). Biology of Bryophytes. New Age International. p. 207. ISBN 978-81-224-1343-4. Retrieved 20 July 2025.
- ^ Cruz, Jorddy Neves (28 August 2023). Drug Discovery and Design Using Natural Products. Springer Nature. p. 191. ISBN 978-3-031-35205-8. Retrieved 20 July 2025.
- ^ Pal, Dilipkumar; Nayak, Amit Kumar (14 December 2020). Bioactive Natural Products for Pharmaceutical Applications. Springer Nature. p. 488. ISBN 978-3-030-54027-2. Retrieved 20 July 2025.
- ^ Adewusi, Emmanuel Adekanmi; Steenkamp, Paul; Fouche, Gerda; Steenkamp, Vanessa (1 September 2013). "Isolation of Cycloeucalenol from Boophone Disticha and Evaluation of its Cytotoxicity". Natural Product Communications. 8 (9): 1934578X1300800906. doi:10.1177/1934578X1300800906. ISSN 1934-578X. Retrieved 20 July 2025.
- ^ Gomes, Ana Yara S.; Souza, Maria de Fátima V.; Cortes, Steyner F.; Lemos, Virgínia S. (October 2005). "Mechanism Involved in the Spasmolytic Effect of a Mixture of Two Triterpenes, Cycloartenol and Cycloeucalenol, Isolated from Herissanthia tiubae in the Guinea-Pig Ileum". Planta Medica. 71 (11): 1025–1029. Bibcode:2005PlMed..71.1025G. doi:10.1055/s-2005-871291. ISSN 0032-0943. PMID 16320203. Retrieved 20 July 2025.
- ^ Brar, Satinder Kaur; Sarma, Saurabh Jyoti; Pakshirajan, Kannan (2 June 2016). Platform Chemical Biorefinery: Future Green Chemistry. Elsevier. p. 346. ISBN 978-0-12-803004-2. Retrieved 20 July 2025.
- ^ Martonosi, Anthony (6 December 2012). The Enzymes of Biological Membranes: Volume 2 Biosynthesis of Cell Components. Springer Science & Business Media. p. 215. ISBN 978-1-4684-2655-7. Retrieved 20 July 2025.