TY - JOUR
T1 - Pyrrolidinooxazolidine alkaloids from two species of ladybird beetles
AU - Radford, Peter
AU - Attygalle, Athula B.
AU - Meinwald, Jerrold
AU - Smedley, Scott R.
AU - Eisner, Thomas
PY - 1997/8
Y1 - 1997/8
N2 - From the mixture of alkaloids obtained from adults of two species of ladybird beetles, Epilachna varivestis and Epilachna borealis, a novel bicyclic alkaloid, 5-(12'-aminotridecyl)pyrrolidinooxazolidine [(5α,7aβ)- hexahydro-α-methylpyrrolo[2,1-b]oxazole-5-dodecaneamine] (2) was characterized on the basis of spectrometric and synthetic investigations. This new alkaloid is related structurally to a monocyclic congener 1-(2- hydroxyethyl)-2-(12'-aminotridecyl)pyrrolidine (1), previously characterized from E. varivestis. Two additional alkaloids (lower homologs of 1 and 2) from E. borealis were characterized as 5-(10'-aminoundecyl)pyrrolidinooxazolidine [(5α,7aβ)-hexahydro-α-methylpyrrolo[2,1-b]oxazole-5-decaneamine] (7) and 1-(2-hydroxyethyl)-2(10'-aminoundecyl)pyrrolidine (8), on the basis of their mass spectra.
AB - From the mixture of alkaloids obtained from adults of two species of ladybird beetles, Epilachna varivestis and Epilachna borealis, a novel bicyclic alkaloid, 5-(12'-aminotridecyl)pyrrolidinooxazolidine [(5α,7aβ)- hexahydro-α-methylpyrrolo[2,1-b]oxazole-5-dodecaneamine] (2) was characterized on the basis of spectrometric and synthetic investigations. This new alkaloid is related structurally to a monocyclic congener 1-(2- hydroxyethyl)-2-(12'-aminotridecyl)pyrrolidine (1), previously characterized from E. varivestis. Two additional alkaloids (lower homologs of 1 and 2) from E. borealis were characterized as 5-(10'-aminoundecyl)pyrrolidinooxazolidine [(5α,7aβ)-hexahydro-α-methylpyrrolo[2,1-b]oxazole-5-decaneamine] (7) and 1-(2-hydroxyethyl)-2(10'-aminoundecyl)pyrrolidine (8), on the basis of their mass spectra.
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U2 - 10.1021/np970140v
DO - 10.1021/np970140v
M3 - Article
C2 - 9287414
AN - SCOPUS:0030609858
SN - 0163-3864
VL - 60
SP - 755
EP - 759
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 8
ER -