Aucubin

Aucubin

Names
IUPAC name (2S,3R,4S,5S,6R)-2-[-(1S,4aR,5S,7aS-5-Hydroxy-7-(hydroxymethyl-1,4a,5,7a-tetrahydrocyclopenta-[c]-pyran-1-yl]-oxy]-6-(hydroxymethyl)-oxane-3,4,5-triol
Other names Aucubin
Identifiers
CAS Number	479-98-1 N
3D model (Jmol)	Interactive image
Beilstein Reference	50340
ChEMBL	ChEMBL514882 N
ChemSpider	82585 Y
ECHA InfoCard	100.006.856
PubChem	91458
InChI InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1 Y Key: RJWJHRPNHPHBRN-FKVJWERZSA-N Y InChI=1/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1 Key: RJWJHRPNHPHBRN-FKVJWERZBS
SMILES O2\C=C/[C@@H]1[C@@H](C(=C/[C@H]1O)\CO)[C@@H]2O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO
Properties
Chemical formula	C15H22O9
Molar mass	346.33 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Iridoids decrease the growth rates of many generalist herbivores.

Aucubin, as other iridoids, is found in asterids such as Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), Plantago asiatic, Plantago major, Plantago lanceolata (Plantaginaceae), Galium aparine (Rubiaceae) and others. These plants are used in traditional Chinese and folk medicine.

Agnuside is composed of aucubin and p-hydroxybenzoic acid.

Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally.

Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety.

Geranyl pyrophosphate (GPP) is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multi-step process, including the dephosphorylation DMAPP, IPP and DMAPP are combined to form the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis.