Chemistry:Sapogenin
Sapogenins are aglycones (non-saccharide moieties) of saponins, a large family of natural products. Sapogenins contain steroid or other triterpene frameworks as their key organic feature. Some steroidal sapogenins can serve as a practical starting point for the semisynthesis of particular steroid hormones.
Examples
The Spirostanols are Listed alphabetically:[1]
Agapanthagenin, Agavogenin, Andesgenin, Australigenin, Bethogenin, Cacogenin,[2] Cepagenin, Chiapagenin, Chlorogenin, Cholegenin,[3] cologenin, Convallagenin-A, Convallagenin-B, Convallamarogenin, Correllogenin, 9-dehydromanogenin, Digalogenin, Digitogenin, Diosgenin, Diotigenin, Epiruscogenin, Epitigogenin, Gentrogenin (botogenin), Gitogenin, Hecogenin,[4] Heloniogenin, Hispidogenin, Isochiapagenin, Isocholegenin, Isorhodeasapogenin, Isokammogenin, Isonarthogenin, Isonuatigenin, Isorhodeasapogenin, Jimogenin,[5] Kammogenin, Kogagenin, Kitigenin, Laxogenin, Lubigenin, Isonuatigenin, Lilagenin, Magogenin,[6] Manogenin, Markogenin, Metagenin, Mexogenin, Namogenin B, Narthogenin, Neobotogenin, Neochlorogenin, Neodigalogenin, Neodigitogenin,Neogitogenin, Neohecogenin, Neokammogenin, Neomanogenin, Neonogiragenin, Neomexogenin, Neoruscogenin, Neotigogenin, Nogiragenin, Nuatigenin, Pennogenin, Pentologenin, Prazerigenin A, Rhodeasapogenin, Ricogenin,[7] Rockogenin, Ruscogenin, Samogenin, Sisalagenin, Sarsasapogenin, Solagenin, Smilagenin, Spirostanol, Spirotaccagenin, Tamusgenin, Texogenin, Tigogenin, Tokorogenin, Willagenin, Yamogenin, Yonogenin & Yuccagenin.
Some alkaloidal spirostanols that are classed as spirosolans include: solasodine, tomatidine
Other examples of steroidal sapogenins include: diosgenone, Penupogenin & Qingyangshengenin & Smilagenone.
Selected furostanols: Prototigogenin, Protoneotigogenin, Protodiosgenin, Protogitogenin, Protoneogitogenin.
An example of a Triterpenoid sapogenin is Cryptogenin, oleanolic acid, hederagenin, gypsogenin.
References
- ↑ Elks, J. (1964). "Rodd's Chemistry of Carbon Compounds". Steroid Saponins and Sapogenins. Elsevier. pp. 1–53. doi:10.1016/B978-044453345-6.50582-4. https://linkinghub.elsevier.com/retrieve/pii/B9780444533456505824.
- ↑ Marker, R. E. (October 1947). "Steroidal Sapogenins. No. 169. Magogenin and Cacogenin and their Biogenesis to Chlorogenin and Tigogenin". Journal of the American Chemical Society 69 (10): 2399–2401. doi:10.1021/ja01202a045. https://pubs.acs.org/doi/abs/10.1021/ja01202a045.
- ↑ Mazur, Y.; Spring, F. S. (1954). "Steroids. Part XII. The structures of cholegenin and isocholegenin". Journal of the Chemical Society (Resumed): 1223. doi:10.1039/jr9540001223. ISSN 0368-1769. https://xlink.rsc.org/?DOI=jr9540001223.
- ↑ Djerassi, Carl; Martinez, H.; Rosenkranz, G. (1951). "Steroidal Sapogenins. Vii.1Experiments in the Hecogenin Series (Part 1)". The Journal of Organic Chemistry 16 (2): 303–308. doi:10.1021/jo01142a021.
- ↑ Hill, R. A., ed (1991). Dictionary of steroids (1st ed.). Chapman & Hall. ISBN 978-0-412-27060-4.
- ↑ MARKER RE. Steroidal sapogenins; magogenin and cacogenin and their biogenesis to chlorogenin and tigogenin. J Am Chem Soc. 1947 Oct;69(10):2399. doi:10.1021/ja01202a045. PMID 20268295.
- ↑ Marker, R. E. (19 November 1949). "STEROIDAL SAPOGENINS, 173. 16-DEHYDROPREGNEN-5-OL-3-DIONE-12,20 FROM RICOGENIN, A NEW STEROIDAL SAPOGENIN". Journal of the American Chemical Society 71 (11): 3856–3856. doi:10.1021/ja01179a527. https://pubs.acs.org/doi/abs/10.1021/ja01179a527.
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