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]
Historyedit
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 triterpenesedit
All of these compounds share the same pentacyclic framework:
^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.
^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.
January 01, 1970
hederagenin, triterpenoid, which, chemical, constituent, hedera, helix, plant, names, iupac, name, dihydroxyolean, acid, systematic, iupac, name, 12ar, 12br, 14bs, hydroxy, hydroxymethyl, hexamethyl, octadecahydropicene, carboxylic, acid, identifiers, number, . Hederagenin is a triterpenoid which is a chemical constituent of the Hedera helix plant Hederagenin Names IUPAC name 3b 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 465 99 6 Y 3D model JSmol Interactive image ChEBI CHEBI 69579 N ChEMBL ChEMBL486400 Y ChemSpider 66038 Y ECHA InfoCard 100 006 701 PubChem CID 73299 UNII RQF57J8212 Y 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 s1 YKey PGOYMURMZNDHNS MYPRUECHSA N YInChI 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 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 Chemical formula C 30H 48O 4 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 N verify what is Y N Infobox references 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 History editHederagenin 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 editAll 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 HopaneReferences edit 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 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 Retrieved from https en wikipedia org w index php title Hederagenin amp oldid 1152844303, wikipedia, wiki, book, books, library,
