Hederagenin

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Hederagenin
Hederagenin.svg
Identifiers
CAS number 465-99-6 N
PubChem 73299
ChemSpider 66038 YesY
ChEBI CHEBI:69579 N
ChEMBL CHEMBL486400 YesY
Jmol-3D images Image 1
Properties
Molecular formula C30H48O4
Molar mass 472.70 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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[edit]

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]

Related triterpenes[edit]

All these compounds share the same pentacyclic framework:

References[edit]

  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.