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.
01Steroid sapogenins
The Spirostanols are Listed alphabetically:
Agapanthagenin, Agavogenin, Andesgenin, Australigenin, Bethogenin, Cacogenin, Cepagenin, Chiapagenin, Chlorogenin, Cholegenin, cologenin, Convallagenin-A, Convallagenin-B, Convallamarogenin, Correllogenin, 9-dehydromanogenin, dihydrokryptogenin, Digalogenin, Digitogenin, Diosgenin, Diotigenin, Epiruscogenin, Epitigogenin, Gentrogenin (botogenin), Gitogenin, Hecogenin, Heloniogenin, Hispidogenin, Isochiapagenin, Isocholegenin, Isorhodeasapogenin, Isokammogenin, Isonarthogenin, Isonuatigenin, Isorhodeasapogenin, Jimogenin, Kammogenin, Kogagenin, Kitigenin, Laxogenin, Lilagenin, Lubigenin, Isonuatigenin, Lilagenin, Magogenin, 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, 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.
02Other Triterpenoid sapogenins
Triterpenoid sapogenins might be even be more complicated to understand than the steroidal sapogenins listed above. They can be grouped according to their skeleton type:
- Oleanane-type, e.g. oleanolic acid, hederagenin, gypsogenin, bayogenin, echinocystic acid, maslinic acid, arjunolic acid, & momordin aglycones.
- Ursane-type, e.g. Ursolic acid, Asiatic acid, Corosolic acid, Pomolic acid, Rotungenic acid & Madecassic acid.
- Lupane-type, e.g. Lupeol, Betulin, Betulinic acid & Betulonic acid.
- Dammarane-type, e.g Protopanaxadiol, Protopanaxatriol, Dammarendiol, Dammarenediol‑II, & Ocotillol‑type aglycones.
- Lanostane-type, e.g. Lanosterol, Cycloartenol, Parkeol, Schiglauzic acid, Ganoderic acids (from Ganoderma), & Lucidenic acids.
- Hopane-type, e.g. Hopane, Diploptene & Moretenol.
- Cucurbitane-type, e.g. Cucurbitacin B, Cucurbitacin E & Cucurbitacin R.
- Tirucallane/Euphane-type, e.g. Tirucallol, Euphol & Dammaradienol.
- Friedelane-type, e.g. Friedelin, Friedelan‑3‑one, & Epifriedelanol.
- Onocerane-type, e.g. Onoceranone & Onocerol.
- Quassinoid-type, e.g. Bruceanol A, Eurycomanone & Quassin.
- Cycloartane-type, e.g. Cycloastragenol & Astragenol.
- Holostane-type, e.g. Holostane aglycones & Echinosides (aglycones)
- and more unusually Onoceranes, Tetranortriterpenoids & Limonoids.
Unsorted list of examples: caulophyllogenin, cryptogenin, medicagenic acid, , soyasapogenol a, soyasapogenol b, soyasapogenol e, zanhic acid.
Sources and credits
This article is adapted from the Wikipedia article “Sapogenin”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Yamogenin.svg by User:Edgar181, Public domain
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