Loganin

{{Chembox | ImageFile = Loganin structure.svg | ImageSize = 200px | ImageAlt = | ImageFile2 = Loganin 3D BS.png | ImageSize2 = 200px | ImageAlt2 = | IUPACName = Methyl (1''S'',4a''S'',6''S'',7''R'',7a''S'')-1-(β-<small>D</small>-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[''c'']pyran-4-carboxylate | SystematicName = Methyl (1''S'',4a''S'',6''S'',7''R'',7a''S'')-6-hydroxy-7-methyl-1-{[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4a,5,6,7,7a-hexahydrocyclopenta[''c'']pyran-4-carboxylate | OtherNames = Loganoside |Section1={{Chembox Identifiers | CASNo = 18524-94-2 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = H7WJ16Q93C | PubChem = 87691 | ChEBI = 15771 | SMILES = C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O | StdInChI = 1S/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1 | StdInChIKey = AMBQHHVBBHTQBF-UOUCRYGSSA-N | EINECS = 242-398-0 | ChemSpiderID = 79111 | InChI = 1/C17H26O10/c1-6-9(19)3-7-8(15(23)24-2)5-25-16(11(6)7)27-17-14(22)13(21)12(20)10(4-18)26-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9-,10+,11+,12+,13-,14+,16-,17-/m0/s1 | InChIKey = AMBQHHVBBHTQBF-UOUCRYGSBL | RTECS = | MeSHName = | KEGG = C01433}} |Section2={{Chembox Properties | C=17 | H=26 | O=10 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''Loganin''' is one of the best-known of the iridoid glycosides. It is named for the Loganiaceae, having first been isolated from the seeds of a member of that plant family, namely those of ''Strychnos nux-vomica''. It also occurs in ''Alstonia boonei'' (Apocynaceae),<ref>{{cite journal | last1 = Adotey | first1 = J. P. | last2 = Adukpo | first2 = G. E. | last3 = Opoku-Boahen | first3 = Y. | last4 = Armah | first4 = F. A. | title = A Review of the Ethnobotany and Pharmacological Importance of ''Alstonia boonei'' De Wild (Apocynaceae) | journal = ISRN Pharmacology | year = 2012 | volume = 2012 | article-number = 587160 | doi = 10.5402/2012/587160 | pmid = 22900200 | pmc = 3413980 | doi-access = free }}</ref> a medicinal tree of West Africa and in the medicinal/entheogenic shrub Desfontainia spinosa (Columelliaceae) native to Central America and South America.

==Biosynthesis== Loganin is formed from loganic acid by the enzyme loganic acid O-methyltransferase.<ref>{{cite journal |last1=Madyastha |first1=K. Madhava |last2=Guarnaccia |first2=Rocco |last3=Baxter |first3=Claire |last4=Coscia |first4=Carmine J. |title=S-Adenosyl-l-methionine:Loganic Acid Methyltransferase |journal=Journal of Biological Chemistry |date=1973 |volume=248 |issue=7 |pages=2497–2501 |doi=10.1016/S0021-9258(19)44136-7 |doi-access=free }}</ref> Loganin then becomes a substrate for the enzyme secologanin synthase (SLS) to form secologanin, a secoiridoid monoterpene found as part of ipecac and terpene indole alkaloids.<ref>{{cite journal |last1=Yamamoto |first1=Hirobumi |last2=Katano |first2=Nobuyuki |last3=Ooi |first3=Ayaka |last4=Inoue |first4=Kenichiro |title=Secologanin synthase which catalyzes the oxidative cleavage of loganin into secologanin is a cytochrome P450 |journal=Phytochemistry |date=2000 |volume=53 |issue=1 |pages=7–12 |doi=10.1016/S0031-9422(99)00471-9 |pmid=10656401 }}</ref>

{{chemrxn|width=65%| {{chemrxn/cpd|loganin|upright=2.3 }} {{chemrxn/txt|+ NADPH}} {{chemrxn/arw|fwd_in={{chem2|O2}}|fwd_out={{chem2|2 H2O}} }} {{chemrxn/sub|class=skin-invert-image|caption=secologanin }} {{chemrxn/txt|+ NADP⁺ }} }}

==References== {{reflist}}

Category:Iridoid glycosides Category:Cyclopentanes