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

He Zhong Jiang; Rui Tan; Rui Hua Jiao; Xin Zhao Deng; Ren Xiang Tan

doi:10.1055/s-0042-108210

Planta Medica, Inhaltsverzeichnis

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^**

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China

²School of Life Science and Engineering, and College of Medicine, Southwest Jiaotong University, Chengdu, P. R. China

,

Rui Tan^**

²School of Life Science and Engineering, and College of Medicine, Southwest Jiaotong University, Chengdu, P. R. China

,

Rui Hua Jiao

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China

,

Xin Zhao Deng

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China

,

Ren Xiang Tan

¹Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China

› Institutsangaben

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

Volltext

Referenzen

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Zusatzmaterial

Supporting Information

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

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