Chemistry:Cycloeucalenol

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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

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

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

  1. ↑ 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. doi:10.1016/0006-291X(72)90484-6. ISSN 0006-291X. PMID 4638757. Bibcode: 1972BBRC...49..820H. https://www.sciencedirect.com/science/article/abs/pii/0006291X72904846#:~:text=For%20example%2C%20the%20bramble%20isomerase,vivo%20roles%20of%20cyclopropyl%20sterols.. Retrieved 20 July 2025. 
  2. ↑ Chopra, R. N. (2005) (in en). Biology of Bryophytes. New Age International. p. 207. ISBN 978-81-224-1343-4. https://books.google.com/books?id=zYj4Re6VNc0C&dq=Cycloeucalenol&pg=PA207. Retrieved 20 July 2025. 
  3. ↑ Cruz, Jorddy Neves (28 August 2023) (in en). Drug Discovery and Design Using Natural Products. Springer Nature. p. 191. ISBN 978-3-031-35205-8. https://books.google.com/books?id=v5XTEAAAQBAJ&dq=Cycloeucalenol++cycloartenol&pg=PA191. Retrieved 20 July 2025. 
  4. ↑ Pal, Dilipkumar; Nayak, Amit Kumar (14 December 2020) (in en). Bioactive Natural Products for Pharmaceutical Applications. Springer Nature. p. 488. ISBN 978-3-030-54027-2. https://books.google.com/books?id=kfsOEAAAQBAJ&dq=Cycloeucalenol&pg=PA488. Retrieved 20 July 2025. 
  5. ↑ Adewusi, Emmanuel Adekanmi; Steenkamp, Paul; Fouche, Gerda; Steenkamp, Vanessa (1 September 2013). "Isolation of Cycloeucalenol from Boophone Disticha and Evaluation of its Cytotoxicity" (in EN). Natural Product Communications 8 (9). doi:10.1177/1934578X1300800906. ISSN 1934-578X. https://journals.sagepub.com/doi/10.1177/1934578X1300800906. Retrieved 20 July 2025. 
  6. ↑ 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" (in en). Planta Medica 71 (11): 1025–1029. doi:10.1055/s-2005-871291. ISSN 0032-0943. PMID 16320203. Bibcode: 2005PlMed..71.1025G. https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-2005-871291. Retrieved 20 July 2025. 
  7. ↑ Brar, Satinder Kaur; Sarma, Saurabh Jyoti; Pakshirajan, Kannan (2 June 2016) (in en). Platform Chemical Biorefinery: Future Green Chemistry. Elsevier. p. 346. ISBN 978-0-12-803004-2. https://books.google.com/books?id=dbV7BgAAQBAJ&dq=Cycloeucalenol&pg=PA346. Retrieved 20 July 2025. 
  8. ↑ Martonosi, Anthony (6 December 2012) (in en). The Enzymes of Biological Membranes: Volume 2 Biosynthesis of Cell Components. Springer Science & Business Media. p. 215. ISBN 978-1-4684-2655-7. https://books.google.com/books?id=dlvTBwAAQBAJ&dq=Cycloeucalenol&pg=PA215. Retrieved 20 July 2025. 



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