Isolation and Characterization of New Onionins A2 and A3 from Allium cepa, and of Onionins A1, A2, and A3 from Allium fistulosum

• Published in: Chemical & pharmaceutical bulletin Vol. 62; no. 11; pp. 1141 - 1145
• Main Authors: Nohara, Toshihiro, Fujiwara, Yukio, Kudo, Rino, Yamaguchi, Koki, Ikeda, Tsuyoshi, Murakami, Kotaro, Ono, Masateru, Kajimoto, Tetsuya, Takeya, Motohiro
• Format: Journal Article
• Language: English
• Published: Japan The Pharmaceutical Society of Japan 01-11-2014; Pharmaceutical Society of Japan; Japan Science and Technology Agency
• Subjects: Allium cepa; anticancer agent; Antigens, CD - analysis; Antigens, CD - immunology; Antigens, Differentiation, Myelomonocytic - analysis; Antigens, Differentiation, Myelomonocytic - immunology; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Cells, Cultured; Humans; Immunologic Factors - chemistry; Immunologic Factors - isolation & purification; Immunologic Factors - pharmacology; macrophage activation; Macrophages - drug effects; Macrophages - immunology; onion; onionin; Onions - chemistry; Plant Roots - chemistry; Receptors, Cell Surface - analysis; Receptors, Cell Surface - immunology; Sulfenic Acids - chemistry; Sulfenic Acids - isolation & purification; Sulfenic Acids - pharmacology; tetrahydrothiophene; Thiophenes - chemistry; Thiophenes - isolation & purification; Thiophenes - pharmacology
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.c14-00461

In this study, the new stable sulfur-containing compounds onionins A2 (1) and A3 (2) were isolated from the acetone extracts of the bulbs of Allium cepa L. and identified as the stereoisomers of onionin A1 discovered in our previous study. Their chemical structures, 3,4-dimethyl-5-(1E-propenyl)-tetrahydrothiophene-2-sulfenic acid-S-oxides, were characterized using various spectroscopic techniques. In addition, 1 and 2 together with onionin A1 were successfully isolated from the leaves of the Welsh onion, Allium fistulosum L. The onion-extracted fractions showed good potential to inhibit the polarization of M2 activated macrophages, indicating their possible ability to inhibit tumor cell proliferation.