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Hederagenin

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Hederagenin
Names
IUPAC name 3β,23-Dihydroxyolean-12-en-28-oic acid
Systematic IUPAC name (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-9-Hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.701 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C30H48O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1Key: PGOYMURMZNDHNS-MYPRUECHSA-N
  • InChI=1/C30H48O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,23-,26-,27-,28+,29+,30-/m0/s1Key: PGOYMURMZNDHNS-MYPRUECHBG
SMILES
  • O=C(O)35(C\2=C\C14((CC1(/2(C)CC3)C)(C)(CO)(O)CC4)C)CC(C)(C)CC5
Properties
Chemical formula C30H48O4
Molar mass 472.710 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Hederagenin is a triterpenoid which is a chemical constituent of the Hedera helix plant.

Hederagenin is the aglycone part of numerous saponins found in Hedera helix (common ivy), the most prevalent of these being hederacoside C and alpha-hederin. It is also one of three primary triterpenoids extracted from the Chenopodium quinoa plant categorized by the EPA as a biopesticide. HeadsUp Plant Protectant is made up of approximately equal ratios of the saponin aglycones oleanolic acid, hederagenin, and phytolaccagenic acid and is intended for use as a seed treatment on tuber (e.g. potato seed pieces), legume, and cereal seeds or as a pre-plant root dip for roots of transplants, at planting, to prevent fungal growth, bacterial growth, and viral plant diseases.

Hederagenin has been found to have antidepressant-like effects in a rodent models.

History

Hederagenin was discovered by L. Posselt in 1849 and named hederic acid. However, Posselt was not able to isolate a pure substance or obtain an exact formula: his hederic acid was hederagenin mixed with some tannin impurity.

Related triterpenes

All of these compounds share the same pentacyclic framework:

References

  1. BIOPESTICIDES REGISTRATION ACTION DOCUMENT, Saponins of Chenopodium quinoa.
  2. Zhou, D; Jin, H; Lin, HB; Yang, XM; Cheng, YF; Deng, FJ; Xu, JP (2010). "Antidepressant effect of the extracts from Fructus Akebiae". Pharmacology Biochemistry and Behavior. 94 (3): 488–95. doi:10.1016/j.pbb.2009.11.003. PMID 19931301.
  3. L. Posselt, "On the constituents of the seeds of ivy", Liebig's Annalen der Chemie, January 1849.
  4. John Lionel Simonsen, The Terpenes, p. 174, Cambridge University Press, 1947 OCLC 309782.
Saponin Glycosides
Sapogenin (aglycone)
Steroidal
(C27 skeleton)
Triterpene
(C30 skeleton)
Tetracyclic
Pentacyclic
Glycone
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