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Sapogenin

Sapogenins are aglycones 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.

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The chemical structure of yamogenin,1 a sapogenin found in fenugreek source ↗

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:2
Agapanthagenin, Agavogenin, Andesgenin, Australigenin, Bethogenin, Cacogenin,3 Cepagenin, Chiapagenin, Chlorogenin, Cholegenin,4 cologenin, Convallagenin-A, Convallagenin-B, Convallamarogenin, Correllogenin, 9-dehydromanogenin, dihydrokryptogenin, Digalogenin, Digitogenin, Diosgenin, Diotigenin, Epiruscogenin, Epitigogenin, Gentrogenin (botogenin), Gitogenin, Hecogenin,5 Heloniogenin, Hispidogenin, Isochiapagenin, Isocholegenin, Isorhodeasapogenin, Isokammogenin, Isonarthogenin, Isonuatigenin, Isorhodeasapogenin, Jimogenin,6 Kammogenin, Kogagenin, Kitigenin, Laxogenin, Lilagenin, Lubigenin, Isonuatigenin, Lilagenin, Magogenin,7 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,8 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

References

  1. Roland Hardman, Ezekiel Abayomi Sofowora (March 1970). "Isolation and characterization of yamogenin from balanites aegyptiaca". Phytochemistry. 9 (3): 645–649. doi:10.1016/S0031-9422(00)85706-4.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. Hill, R. A., ed. (1991). Dictionary of steroids (1st ed.). Chapman & Hall. ISBN 978-0-412-27060-4.
  7. 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.
  8. 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.