Serratenediol
| Names | |
|---|---|
| IUPAC name
(3S,6R,8S,11R,12S,15S,16R,19S,21R)-3,7,7,11,16,20,20-heptamethylpentacyclo[13.8.0.03,12.06,11.016,21]tricos-1(23)-ene-8,19-diol
| |
| Other names
Pinusenediol[1]
| |
| Identifiers | |
3D model (JSmol)
|
|
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C30H50O2 | |
| Molar mass | 442.728 g·mol−1 |
| Appearance | Powder[2] |
| poorly soluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
| |
Serratenediol is a naturally occurring pentacyclic triterpenoid.[3] 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[4], which differentiates it from the more common lupane, oleanane, or ursane types.[5] The compound is also called pinusenediol.[6]
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).[7][8][9]
Synthesis
The synthesis of serratenediol is accomplished in several steps by using polyene cyclization.[10]
Physical properties
The compound forms powder. It is poorly soluble in water, but soluble in chloroform, dichloromethane, ethyl acetate, DMSO, acetone, etc.[11]
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.[12][13]
References
- ^ Dev, Sukh (1 February 2018). Handbook of Terpenoids: Volume II. CRC Press. p. 2056. ISBN 978-1-351-08966-1. Retrieved 3 January 2026.
- ^ "CAS NO. 2239-24-9 | Serratenediol | Catalog BBP00103 | Arctom | Products". arctomsci.com. Retrieved 3 January 2026.
- ^ Devon, T. K. (2 December 2012). Handbook of Naturally Occurring Compounds V2. Elsevier. p. 341. ISBN 978-0-323-14510-7. Retrieved 2 January 2026.
- ^ Sjostrom, Eero (22 October 2013). Wood Chemistry: Fundamentals and Applications. Elsevier. p. 101. ISBN 978-0-08-092589-9. Retrieved 3 January 2026.
- ^ ApSimon, John (22 September 2009). The Total Synthesis of Natural Products, Volume 6. John Wiley & Sons. p. 132. ISBN 978-0-470-12957-9. Retrieved 2 January 2026.
- ^ Handbook of Natural Products Data: Pentacyclic triterpenoids. Elsevier. 1990. p. 1518. ISBN 978-0-444-88173-1. 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). 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. 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). Natural Products Chemistry. University Science Books. p. 199. ISBN 978-0-935702-14-9. Retrieved 3 January 2026.
- ^ "Serratenediol | CAS:2239-24-9 | Triterpenoids | High Purity | Manufacturer BioCrick". biocrick.com. Retrieved 3 January 2026.
- ^ "Serratenediol | BCL | Caspase | PARP | TargetMol". TargetMol.com. Retrieved 3 January 2026.
- ^ 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.