Loganin

Loganin
Names
IUPAC name
Methyl (1S,4aS,6S,7R,7aS)-1-(β-D-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Systematic IUPAC name
Methyl (1S,4aS,6S,7R,7aS)-6-hydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Other names
Loganoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.038.529 Edit this at Wikidata
EC Number
  • 242-398-0
KEGG
UNII
  • InChI=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
    Key: AMBQHHVBBHTQBF-UOUCRYGSSA-N
  • 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
    Key: AMBQHHVBBHTQBF-UOUCRYGSBL
  • 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
Properties
C17H26O10
Molar mass 390.385 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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),[1] 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.[2] 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.[3]

2D representation of the chemical structure of loganin.
loganin
+ NADPH
 
 
O2
2 H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
secologanin
+ NADP+
 


References

  1. ^ Adotey, J. P.; Adukpo, G. E.; Opoku-Boahen, Y.; Armah, F. A. (2012). "A Review of the Ethnobotany and Pharmacological Importance of Alstonia boonei De Wild (Apocynaceae)". ISRN Pharmacology. 2012 587160. doi:10.5402/2012/587160. PMC 3413980. PMID 22900200.
  2. ^ Madyastha, K. Madhava; Guarnaccia, Rocco; Baxter, Claire; Coscia, Carmine J. (1973). "S-Adenosyl-l-methionine:Loganic Acid Methyltransferase". Journal of Biological Chemistry. 248 (7): 2497–2501. doi:10.1016/S0021-9258(19)44136-7.
  3. ^ Yamamoto, Hirobumi; Katano, Nobuyuki; Ooi, Ayaka; Inoue, Kenichiro (2000). "Secologanin synthase which catalyzes the oxidative cleavage of loganin into secologanin is a cytochrome P450". Phytochemistry. 53 (1): 7–12. doi:10.1016/S0031-9422(99)00471-9. PMID 10656401.

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