N-Glucosides of Fairy Chemicals, 2-Azahypoxanthine and 2-Aza-8-oxohypoxanthine, in Rice

Jae-Hoon Choi; Jing Wu; Azusa Sawada; Syougo Takeda; Hirohide Takemura; Kaoru Yogosawa; Hirofumi Hirai; Mitsuru Kondo; Kunihisa Sugimoto; Tomohiro Asakawa; Makoto Inai; Toshiyuki Kan; Hirokazu Kawagishi

doi:10.1021/acs.orglett.7b03736

N-Glucosides of Fairy Chemicals, 2-Azahypoxanthine and 2-Aza-8-oxohypoxanthine, in Rice

Org Lett. 2018 Jan 5;20(1):312-314. doi: 10.1021/acs.orglett.7b03736. Epub 2017 Dec 13.

Authors

Jae-Hoon Choi, Jing Wu, Azusa Sawada, Syougo Takeda, Hirohide Takemura, Kaoru Yogosawa, Hirofumi Hirai, Mitsuru Kondo, Kunihisa Sugimoto¹, Tomohiro Asakawa², Makoto Inai³, Toshiyuki Kan³, Hirokazu Kawagishi

Affiliations

¹ Research & Utilization Division, Japan Synchrotron Radiation Research Institute , 1-1-1 Koto, Sayo-cho, Sayo-gun, Hyogo 679-5198, Japan.
² Tokai University Institute of Innovative Science and Technology , 4-1-1 Kitakaname, Hiratsuka City, Kanagawa 259-1292, Japan.
³ School of Pharmaceutical Sciences, University of Shizuoka , 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.

PMID: 29235343
DOI: 10.1021/acs.orglett.7b03736

Abstract

Plant growth stimulators, 2-azahypoxanthine (AHX) and 2-aza-8-oxohypoxanthine (AOH), were isolated from the fairy-ring-forming fungus, Lepista sordida, and AHX-treated rice, respectively. Further metabolites of AHX were detected in AHX-treated rice by HPLC, and the metabolites 1-4 were isolated from the rice. The structures of 1-4 were determined by spectroscopic analysis and synthesis. Compounds 1-4 exhibited no significant activity against rice, indicating that rice regulates the activity of AHX and AOH by converting them into their glucosides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Glucosides
Hypoxanthines
Molecular Structure
Oryza*

Substances

2-aza-8-oxohypoxanthine
Glucosides
Hypoxanthines
2-azahypoxanthine