Applying Mosher's method to acetogenins bearing vicinal diols. The absolute configurations of muricatetrocin C and rollidecins A and B, new bioactive acetogenins from Rollinia mucosa.
Muricatetrocin C (1), rollidecin A (2), and rollidecin B (3), three new bioactive annonaceous acetogenins bearing vicinal diols, were isolated from the leaves of Rollinia mucosa (Annonaceae) using activity-directed fractionation. The total structural elucidations of 1-3, including the absolute stereochemistries of the vicinal diols, were achieved by analyzing their per-Mosher ester derivatives. All three compounds showed potent and selective inhibitory effects against several human cancer cell lines.
Shi
G
G
Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, IN 47907, USA.
Gu
Z M
ZM
He
K
K
Wood
K V
KV
Zeng
L
L
Ye
Q
Q
MacDougal
J M
JM
McLaughlin
J L
JL
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry*; D001156:Artemia; D005663:Furans / Q000737:chemistry*; D006801:Humans; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011487:Protein Conformation; D013237:Stereoisomerism; D014197:Trees / Q000737:chemistry*
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; C100863:rollinecin A; C100864:rollinecin B; C095614:muricatocin A; D015107:4-Butyrolactone