Hederagenin

Last updated
Hederagenin
Hederagenin.svg
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.701 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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/s1 Yes check.svgY
    Key: PGOYMURMZNDHNS-MYPRUECHSA-N Yes check.svgY
  • 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/s1
    Key: PGOYMURMZNDHNS-MYPRUECHBG
  • O=C(O)[C@]35[C@H](C\2=C\C[C@@H]1[C@@]4([C@@H](CC[C@]1([C@]/2(C)CC3)C)[C@](C)(CO)[C@@H](O)CC4)C)CC(C)(C)CC5
Properties
C30H48O4
Molar mass 472.710 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hederagenin is a triterpenoid which is a chemical constituent of the Hedera helix plant.

Contents

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]

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. ↑ Lentschat, H; Liessmann, F; Tydings, C; Schermeng, T; Stichel, J; Urban, N; Schaefer, M; Meiler, J; Beck-Sickinger, AG (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): e202417786. doi:10.1002/anie.202417786. PMID   39641914.{{cite journal}}: CS1 maint: article number as page number (link)
  4. ↑ L. Posselt, "On the constituents of the seeds of ivy", Liebig's Annalen der Chemie, January 1849.
  5. ↑ John Lionel Simonsen, The Terpenes, p. 174, Cambridge University Press, 1947 OCLC   309782.
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