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Planta Med 2016; 82(11/12): 1122-1127
DOI: 10.1055/s-0042-108210
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Herpecaudin from Herpetospermum caudigerum, a Xanthine Oxidase Inhibitor with a Novel Isoprenoid Scaffold[*]

He Zhong Jiang   **
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China
2   School of Life Science and Engineering, and College of Medicine, Southwest Jiaotong University, Chengdu, P. R. China
,
Rui Tan   **
2   School of Life Science and Engineering, and College of Medicine, Southwest Jiaotong University, Chengdu, P. R. China
,
Rui Hua Jiao
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China
,
Xin Zhao Deng
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China
,
Ren Xiang Tan
1   Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China
› Author Affiliations
Further Information

Publication History

received 18 April 2016
revised 25 April 2016

accepted 29 April 2016

Publication Date:
07 June 2016 (online)

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Abstract

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.

Key words

Herpetospermum caudigerum - Cucurbitaceae - Herpecaudin - xanthine oxidase inhibitor - retro-aldol reaction - cucurbitane-type terpenoid

* Dedicated to Professor Dr. Dr. h. c. mult. Kurt Hostettmann in recognition of his outstanding contribution to natural product research.


** These authors contributed equally to this work.


Supporting Information

 

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