Chemistry:Hederagenin
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 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.[2] It has been shown to act as an antagonist of the NPFF1 receptor.[3]
History
Hederagenin was discovered by L. Posselt in 1849 and named hederic acid.[4] 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.[5]
Related triterpenes
All of these compounds share the same pentacyclic framework:
- Betulinic acid
- Boswellic acid
- Glycyrrhetinic acid
- Moronic acid
- Oleanolic acid
- Ursolic acid
- Corosolic acid
- Amyrin
- Lupeol
- Maslinic acid
- Hopane
References
- ↑ BIOPESTICIDES REGISTRATION ACTION DOCUMENT, Saponins of Chenopodium quinoa.
- ↑ 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.
- ↑ Lentschat, H; Liessmann, F; Tydings, C; Schermeng, T; Stichel, J; Urban, N; Schaefer, M; Meiler, J et al. (Feb 2025). "Hederagenin is a Highly Selective Antagonist of the Neuropeptide FF Receptor 1 that Reveals Mechanisms for Subtype Selectivity". Angew Chem Int Ed Engl 64 (6). doi:10.1002/anie.202417786. PMID 39641914.
- ↑ L. Posselt, "On the constituents of the seeds of ivy", Liebig's Annalen der Chemie, January 1849.
- ↑ John Lionel Simonsen, The Terpenes, p. 174, Cambridge University Press, 1947 OCLC 309782.
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