TY - JOUR
T1 - Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellata
AU - White, Andrew M.
AU - Pierens, Gregory K.
AU - Skinner-Adams, Tina
AU - Andrews, Katherine T.
AU - Bernhardt, Paul V.
AU - Krenske, Elizabeth H.
AU - Mollo, Ernesto
AU - Garson, Mary J.
N1 - Publisher Copyright:
© 2015 The American Chemical Society and American Society of Pharmacognosy.
PY - 2015/6/26
Y1 - 2015/6/26
N2 - Five new isocyano/isothiocyanato sesquiterpenes (1-5) with tri- or bicyclic carbon skeletons have been characterized from Australian specimens of the nudibranch Phyllidia ocellata. Spectroscopic analyses at 900 MHz were informed by DFT calculations. The 1S, 5S, 8R configuration of 2-isocyanoclovene (1) was determined by X-ray crystallographic analysis of formamide 6. A biosynthetic pathway to clovanes 1 and 2 from epicaryolane precursors is proposed. Isocyanides 1, 2, and 4 showed activity against Plasmodium falciparum (IC50 0.26-0.30 μM), while isothiocyanate 3 and formamide 6 had IC50 values of >10 μM.
AB - Five new isocyano/isothiocyanato sesquiterpenes (1-5) with tri- or bicyclic carbon skeletons have been characterized from Australian specimens of the nudibranch Phyllidia ocellata. Spectroscopic analyses at 900 MHz were informed by DFT calculations. The 1S, 5S, 8R configuration of 2-isocyanoclovene (1) was determined by X-ray crystallographic analysis of formamide 6. A biosynthetic pathway to clovanes 1 and 2 from epicaryolane precursors is proposed. Isocyanides 1, 2, and 4 showed activity against Plasmodium falciparum (IC50 0.26-0.30 μM), while isothiocyanate 3 and formamide 6 had IC50 values of >10 μM.
UR - http://www.scopus.com/inward/record.url?scp=84933055130&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.5b00354
DO - 10.1021/acs.jnatprod.5b00354
M3 - Article
C2 - 26056748
AN - SCOPUS:84933055130
SN - 0163-3864
VL - 78
SP - 1422
EP - 1427
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 6
ER -