Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus
Zalihe Hakki, Benjamin Cao, Allison M Heskes, Jason QD Goodger, Ian E Woodrow, Spencer J Williams
CARBOHYDRATE RESEARCH | ELSEVIER SCI LTD | Published : 2010
Short syntheses of cuniloside B and cypellocarpin C, (+)-(R)-oleuropeic acid-containing carbohydrates, are reported. Also disclosed are syntheses of the noreugenin glycosides, undulatoside A and corymbosins K(1) and K(2). Leaf extracts of 28 diverse eucalypts revealed cuniloside B to be present in all, and cypellocarpin C to be present in most, of the species examined. The widespread occurrence of these carbohydrate monoterpenoid esters supports their roles in essential oil biosynthesis or mobilization from sites of synthesis to secretory cavity lumena.
This work was supported by grants from the Australian Research Council and the Holsworth Wildlife Research Fund (Victorian Community Foundation, ANZ Charitable Trusts). J.Q.D.G. is the recipient of an ARC Australian Research Fellowship. J. Karas is thanked for HPLC support.