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

CAS Number

* 18524-94-2 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:15771

ChemSpider |

* 79111

EC Number |

* 242-398-0

KEGG |

* C01433

PubChem CID

* 87691

UNII |

* H7WJ16Q93C Y

InChI

* 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

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

Properties

Chemical formula

| 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).

Infobox references

Tracking categories (test):

* SizeSet

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 (LAMT). 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.

## 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. PMID 22900200.

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*[CID]: Compound ID