Chemistry:Sapogenin

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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.

Steroid sapogenins

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, dihydrokryptogenin, 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, Lilagenin, 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.

Other 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:

  1. Oleanane-type, e.g. oleanolic acid, hederagenin, gypsogenin, bayogenin, echinocystic acid, maslinic acid, arjunolic acid, & momordin aglycones.
  2. Ursane-type, e.g. Ursolic acid, Asiatic acid, Corosolic acid, Pomolic acid, Rotungenic acid & Madecassic acid.
  3. Lupane-type, e.g. Lupeol, Betulin, Betulinic acid & Betulonic acid.
  4. Dammarane-type, e.g Protopanaxadiol, Protopanaxatriol, Dammarendiol, Dammarenediol‑II, & Ocotillol‑type aglycones.
  5. Lanostane-type, e.g. Lanosterol, Cycloartenol, Parkeol, Schiglauzic acid, Ganoderic acids (from Ganoderma), & Lucidenic acids.
  6. Hopane-type, e.g. Hopane, Diploptene & Moretenol.
  7. Cucurbitane-type, e.g. Cucurbitacin B, Cucurbitacin E & Cucurbitacin R.
  8. Tirucallane/Euphane-type, e.g. Tirucallol, Euphol & Dammaradienol.
  9. Friedelane-type, e.g. Friedelin, Friedelan‑3‑one, & Epifriedelanol.
  10. Onocerane-type, e.g. Onoceranone & Onocerol.
  11. Quassinoid-type, e.g. Bruceanol A, Eurycomanone & Quassin.
  12. Cycloartane-type, e.g. Cycloastragenol & Astragenol.
  13. Holostane-type, e.g. Holostane aglycones & Echinosides (aglycones)
  14. and more unusually Onoceranes, Tetranortriterpenoids & Limonoids.

Unsorted list of examples: caulophyllogenin, cryptogenin, medicagenic acid, , soyasapogenol a, soyasapogenol b, soyasapogenol e, zanhic acid.

References

  1. ↑ 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. 
  2. ↑ 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. 
  3. ↑ 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. 
  4. ↑ 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. 
  5. ↑ Hill, R. A., ed (1991). Dictionary of steroids (1st ed.). Chapman & Hall. ISBN 978-0-412-27060-4. 
  6. ↑ 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.
  7. ↑ 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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