Herpecaudin from Herpetospermum caudigerum, a Xanthine Oxidase Inhibitor with a Novel Isoprenoid Scaffold.
Herpecaudin (3), a xanthine oxidase inhibitor with an unprecedented scaffold, was discovered from Herpetospermum caudigerum seeds. The structure was determined by spectroscopic and X-ray single crystallographic methods. A possible biogenetic pathway leading to herpecaudin is proposed, starting from congeners 23,24-dihydrocucurbitacin E (1) and endecaphyllacin B (2), and involving retro-aldol cleavage as a key step. All three compounds proved to be active and represent new scaffolds of non-purine analogue xanthine oxidase inhibitors.
Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
He Zhong
HZ
Jiang
School of Life Science and Engineering, and College of Medicine, Southwest Jiaotong University, Chengdu, P. R. China.
Rui
R
Tan
Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
Rui Hua
RH
Jiao
Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
Xin Zhao
XZ
Deng
Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
Ren Xiang
RX
Tan
D045744:Cell Line, Tumor; D019662:Cucurbitaceae / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D004791:Enzyme Inhibitors / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014969:Xanthine Oxidase / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D013729:Terpenes; C000614938:herpecaudin; D014969:Xanthine Oxidase