Chemistry:Serratenediol
Serratenediol is a naturally occurring pentacyclic triterpenoid.[1] The compound has drawn interest for its distinctive carbon framework and potential biological activities. Serratenediol is characterized by a rare seven‑membered C-ring, a defining feature of the serratene class of triterpenoids[2], which differentiates it from the more common lupane, oleanane, or ursane types.[3] The compound is also called pinusenediol.[4]
Natural occurrence
The compound is found primarily in plants of the Lycopodiaceae family, especially in the genus Lycopodium (now often segregated into genera like Huperzia and Phlegmariurus).[5][6][7]
Synthesis
The synthesis of serratenediol is accomplished in several steps by using polyene cyclization.[8]
Physical properties
The compound forms powder. It is poorly soluble in water, but soluble in chloroform, dichloromethane, ethyl acetate, DMSO, acetone, etc.[9]
Uses
Scientific studies have investigated serratenediol for several potential therapeutic applications: anti-inflammatory effects, cancer research, antiviral activity (it has demonstrated strong inhibitory effects on the activation of the Epstein–Barr virus), bone health studies.[10][11]
References
- ↑ Devon, T. K. (2 December 2012) (in en). Handbook of Naturally Occurring Compounds V2. Elsevier. p. 341. ISBN 978-0-323-14510-7. https://www.google.ru/books/edition/Handbook_of_Naturally_Occurring_Compound/RyolATGGfVIC?hl=en&gbpv=1&dq=Serratenediol&pg=PA341&printsec=frontcover. Retrieved 2 January 2026.
- ↑ Sjostrom, Eero (22 October 2013) (in en). Wood Chemistry: Fundamentals and Applications. Elsevier. p. 101. ISBN 978-0-08-092589-9. https://www.google.ru/books/edition/Wood_Chemistry/NCkXBQAAQBAJ?hl=en&gbpv=1&dq=Serratenediol+solubility&pg=PA101&printsec=frontcover. Retrieved 3 January 2026.
- ↑ ApSimon, John (22 September 2009) (in en). The Total Synthesis of Natural Products, Volume 6. John Wiley & Sons. p. 132. ISBN 978-0-470-12957-9. https://www.google.ru/books/edition/The_Total_Synthesis_of_Natural_Products/rJPjBKe_FoEC?hl=en&gbpv=1&dq=Serratenediol&pg=PA132&printsec=frontcover. Retrieved 2 January 2026.
- ↑ (in en) Handbook of Natural Products Data: Pentacyclic triterpenoids. Elsevier. 1990. p. 1518. ISBN 978-0-444-88173-1. https://www.google.ru/books/edition/Handbook_of_Natural_Products_Data_Pentac/mPLvAAAAMAAJ?hl=en&gbpv=1&bsq=Serratenediol+pinusenediol&dq=Serratenediol+pinusenediol&printsec=frontcover. Retrieved 3 January 2026.
- ↑ Inubushi, Y.; Sano, T.; Tsuda, Y. (1 January 1964). "Serratenediol: A new skeletal triterpenoid containing a seven membered ring". Tetrahedron Letters 5 (21): 1303–1310. doi:10.1016/S0040-4039(00)90472-6. ISSN 0040-4039.
- ↑ Zhou, Jiaju; Xie, Guirong; Yan, Xinjian (21 February 2011) (in en). Encyclopedia of Traditional Chinese Medicines - Molecular Structures, Pharmacological Activities, Natural Sources and Applications: Vol. 4: Isolated Compounds N-S. Springer Science & Business Media. p. 537. ISBN 978-3-642-16779-9. https://www.google.ru/books/edition/Encyclopedia_of_Traditional_Chinese_Medi/VPjcIdkqStAC?hl=en&gbpv=1&dq=Serratenediol&pg=PA537&printsec=frontcover. Retrieved 2 January 2026.
- ↑ Orito, K.; Manske, R. H.; Rodrigo, R. (15 October 1972). "The Triterpenes of Lycopodiumlucidulum Michx.". Canadian Journal of Chemistry 50 (20): 3280–3282. doi:10.1139/v72-525. ISSN 0008-4042.
- ↑ Nakanishi, Koji (1974) (in en). Natural Products Chemistry. University Science Books. p. 199. ISBN 978-0-935702-14-9. https://www.google.ru/books/edition/Natural_Products_Chemistry/5KRKN9IEMvQC?hl=en&gbpv=1&dq=Serratenediol+synthesis&pg=PA698&printsec=frontcover. Retrieved 3 January 2026.
- ↑ "Serratenediol | CAS:2239-24-9 | Triterpenoids | High Purity | Manufacturer BioCrick". biocrick.com. https://www.biocrick.com/Serratenediol-BCN5061.html#:~:text=Soluble%20in%20Chloroform%2CDichloromethane%2CEthyl%20Acetate%2CDMSO%2CAcetone%2Cetc..
- ↑ "Serratenediol | BCL | Caspase | PARP | TargetMol" (in en). TargetMol.com. https://www.targetmol.com/compound/serratenediol.
- ↑ Tanaka, Reiko; Minami, Toshifumi; Ishikawa, Yohei; Matsunaga, Shunyo; Tokuda, Harukuni; Nishino, Hoyoku (10 July 2003). "Cancer chemopreventive activity of serratane-type triterpenoids on two-stage mouse skin carcinogenesis". Cancer Letters 196 (2): 121–126. doi:10.1016/s0304-3835(03)00214-3. ISSN 0304-3835.
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