Cyclic sulfoxides garlicnins B2, B3, B4, C2, and C3 from Allium sativum.

Abstract

Several novel sulfides, called garlicnins B2 (1), B3 (2), B4 (3), C2 (4), and C3 (5), were isolated from acetone extracts of garlic, Allium sativum L. and characterized. These garlicnins are capable of suppressing M2 macrophage activation and they have a novel skeleton of cyclic sulfoxide. The structures of the former 3 and latter of 2 were deduced to be 2-(sulfenic acid)-5-(allyl)-3,4-dimethyltetrahydrothiophene-S-oxides and 2-(allyldithiine)-5-(propenylsulfoxide)-3,4-dimethyltetrahydrothiophene-S-oxides, respectively. The mechanism of the proposed production of these compounds is discussed. The identification of these novel sulfoxides from garlic accumulates a great deal of new chemistry in the Allium sulfide field, and future pharmacological investigations of these compounds will aid the development of natural, healthy foods and anti-cancer agents that may prevent or combat disease.

• Authors: Toshihiro Nohara, Yukio Fujiwara, Tsuyoshi Ikeda, Kohtaro Murakami, Masateru Ono, Daisuke Nakano, Junei Kinjo
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 61 Issue 7 Pg. 695-9 ( 2013) ISSN: 1347-5223 [Electronic] Japan
• PMID: 23812395 (Publication Type: Journal Article)

Chemical References

• Allyl Compounds
• Antigens, CD
• Antigens, Differentiation, Myelomonocytic
• CD163 antigen
• Disulfides
• Receptors, Cell Surface
• Sulfoxides
• Acetone
• diallyl disulfide

Topics

• Acetone (chemistry)
• Allyl Compounds (chemistry, isolation & purification, pharmacology)
• Antigens, CD (metabolism)
• Antigens, Differentiation, Myelomonocytic (metabolism)
• Cell Line
• Disulfides (chemistry, isolation & purification, pharmacology)
• Garlic (chemistry)
• Humans
• Macrophages (drug effects)
• Magnetic Resonance Spectroscopy
• Molecular Conformation
• Receptors, Cell Surface (metabolism)
• Sulfoxides (chemistry, isolation & purification, pharmacology)