New bioactive adjacent bis-THF annonaceous acetogenins from Annona bullata.
Five new adjacent bis-THF annonaceous acetogenins, 32-hydroxybullatacin, 31-hydroxybullatacin, 30-hydroxybullatacin, and (2,4-cis and trans)-28-hydroxybullatacinones, were isolated from the ethanolic extract of the bark of Annona bullata Rich. (Annonaceae). The absolute configurations of the above five compounds, as well as those of (2,4-cis and trans)-32-, 31-, and 30-hydroxybullatacinones and (2,4-cis and trans)-bulladecinones, previously isolated from the same extract, were defined by the application of the advanced Mosher ester [methoxy(trifluoromethyl)phenyl acetate or MTPA] methodology. The determination of the absolute configuration of C-20 of (2,4-cis and trans)-bulladecinones to be S supports our hypothesis that the cyclization of the THF rings of (2,4-cis and trans)-bulladecinones starts from C-12 (the right side). The first five compounds listed above showed potent bioactivities in the brine shrimp lethality test (BST) and among six human solid tumour cell lines.
Gu
Z M
ZM
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, IN 47907, USA.
Zeng
L
L
Schwedler
J T
JT
Wood
K V
KV
McLaughlin
J L
JL
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D001156:Artemia; D002460:Cell Line; D005663:Furans / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D018547:Plant Stems; D010946:Plants, Medicinal; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans