Hederagenin

Hederagenin
Names
IUPAC name
(3β)-3,23-Dihydroxyolean-12-en-28-oic acid
Identifiers
465-99-6 N
3D model (Jmol) Interactive image
ChEBI CHEBI:69579 N
ChEMBL ChEMBL486400 YesY
ChemSpider 66038 YesY
ECHA InfoCard 100.006.701
PubChem 73299
Properties
C30H48O4
Molar mass 472.71 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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.[1] HeadsUp Plant Protectant is made up of approximately equal ratios of the saponin aglycones oleanolic acid, hederagenin, and phytolaccinic 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.[2]

History

Hederagenin was discovered by L. Posselt in 1849 and named hederic acid.[3] 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.[4]

All 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.
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