Further chemical studies on the Antarctic nudibranch Austrodoris kerguelenensis: new terpenoid acylglycerols and revision of the previous stereochemistry

The diterpenoid acylglycerol fraction from an extract of the mantle of a new collection of the Antarctic dorid gastropod mollusc Austrodoris kerguelenensis has been chemically analysed. Two novel 2-monoacylglycerols 9 and 12, along with known 1,2-diacyl glyceryl esters 5 and 6, now reassigned as 7 and 8, have been isolated. The linkage of a diterpenoid moiety at C-2 of glycerol characterizes all the compounds. Because the R absolute stereochemistry at C-2 of glycerol has been established for the corresponding 1,3-glyceryl esters 1 and 2, derived from 7 and 8 by acyl-migration of the terpenoid moiety from C-2 to C-3, our finding implies that 1,2-derivatives from Antarctic nudibranchs have the same S stereochemistry as all 1,2-sn-diacylglycerols from the other dorids.