Hederagenin

Hederagenin
Names
	IUPAC name (3β)-3,23-Dihydroxyolean-12-en-28-oic acid
Identifiers
CAS Number	465-99-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:69579 ;
ChEMBL	ChEMBL486400 ;
ChemSpider	66038 ;
ECHA InfoCard	100.006.701
PubChem CID	73299;
UNII	RQF57J8212 ;
	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 Key: PGOYMURMZNDHNS-MYPRUECHSA-N ; 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;
	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	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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	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 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

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

All of these compounds share the same pentacyclic framework:

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.
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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[cquinoa-1] BIOPESTICIDES REGISTRATION ACTION DOCUMENT, Saponins of Chenopodium quinoa.

[Zhou-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.