New cyclic sulfides, garlicnins I2, M, N, and O, from Allium sativum

Toshihiro Nohara; Masateru Ono; Naho Nishioka; Fuka Masuda; Yukio Fujiwara; Tsuyoshi Ikeda; Daisuke Nakano; Junei Kinjo

doi:10.1007/s11418-017-1133-2

New cyclic sulfides, garlicnins I₂, M, N, and O, from Allium sativum

J Nat Med. 2018 Jan;72(1):326-331. doi: 10.1007/s11418-017-1133-2. Epub 2017 Oct 30.

Authors

Toshihiro Nohara¹, Masateru Ono², Naho Nishioka², Fuka Masuda², Yukio Fujiwara³, Tsuyoshi Ikeda⁴, Daisuke Nakano⁵, Junei Kinjo⁵

Affiliations

¹ Faculty of Pharmaceutical Sciences, Sojo University, 4-22-2 Ikeda, Nishi-ku, Kumamoto, 860-0082, Japan. none@ph.sojo-u.ac.jp.
² School of Agriculture, Tokai University, 5435 Minamiaso, Aso, Kumamoto, 869-1404, Japan.
³ Graduate School of Medical Sciences, Faculty of Life Sciences, Kumamoto University, 1-1-1, Honjo, Chuo-ku, Kumamoto, 860-8556, Japan.
⁴ Faculty of Pharmaceutical Sciences, Sojo University, 4-22-2 Ikeda, Nishi-ku, Kumamoto, 860-0082, Japan.
⁵ Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka, 814-0180, Japan.

PMID: 29086233
DOI: 10.1007/s11418-017-1133-2

Abstract

One atypical thiolane-type sulfide, garlicnin I₂ (1), two 3,4-dimethylthiolane-type sulfides, garlicnins M (2) and N (3), and one thiabicyclic-type sulfide, garlicnin O (4), were isolated from the acetone extracts of Chinese garlic bulbs, Allium sativum and their structures were characterized. Hypothetical pathways for the production of the respective sulfides were discussed.

Keywords: 3,4-Dimethylthiolane-type; Allium sativum; Atypical thiolane-type; Garlicnin M; Garlicnin O; Thiabicyclic-type.

MeSH terms

Acetone / chemistry
Disulfides / chemistry
Disulfides / isolation & purification*
Garlic / chemistry*
Molecular Conformation
Plant Extracts / chemistry
Plant Extracts / isolation & purification*
Plant Roots / chemistry
Solvents / chemistry
Thiophenes / chemistry
Thiophenes / isolation & purification*

Substances

Disulfides
Plant Extracts
Solvents
Thiophenes
Acetone