LAT Transport Inhibitors from Pittosporum venulosum Identified by NMR Fingerprint Analysis

1H NMR fingerprints were used as the guiding principle for the isolation of minor compounds related to the l-type amino acid transporter inhibitors venulosides A (1) and B (2). Two new monoterpene glycosides, namely, venulosides C (3) and D (4), were isolated from a Queensland collection of the plan...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2015-06, Vol.78 (6), p.1215-1220
Main Authors: Grkovic, Tanja, Pouwer, Rebecca H, Wang, Qian, Guymer, Gordon P, Holst, Jeff, Quinn, Ronald J
Format: Article
Language:English
Subjects:
Amino Acid Transport Systems - chemistry
Amino Acids - metabolism
Biological Transport
Glycosides - chemistry
Glycosides - isolation & purification
Glycosides - pharmacology
Humans
Large Neutral Amino Acid-Transporter 1
Leucine - metabolism
Male
Molecular Structure
Monoterpenes - chemistry
Monoterpenes - isolation & purification
Monoterpenes - pharmacology
Nuclear Magnetic Resonance, Biomolecular
Rosales - chemistry
Structure-Activity Relationship
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Summary:1H NMR fingerprints were used as the guiding principle for the isolation of minor compounds related to the l-type amino acid transporter inhibitors venulosides A (1) and B (2). Two new monoterpene glycosides, namely, venulosides C (3) and D (4), were isolated from a Queensland collection of the plant Pittosporum venulosum. Compounds 3 and 4 were found to inhibit l-leucine transport in LNCaP cells with IC50 values of 11.47 and 39.73 μM, respectively. The venulosides are the first reported natural product inhibitors of leucine transport in prostate cancer cells, and the isolation of the minor compounds provides some early SAR information.
ISSN:0163-3864
1520-6025
DOI:10.1021/np500968t