Thiolane-type sulfides from garlic, onion, and Welsh onion

Abstract

In this paper, we review our work in the last 10 years wherein we examined the sulfides in the acetone extracts of garlic ( Allium sativum ), onion ( A. cepa ), and Welsh onion ( A. fistulosum ), obtained and characterized the structures of new sulfides, three 3,4-dimethylthiolane-type sulfides from onion and Welsh onion, respectively, and four acyclic-type, nine 3,4-dimethyl- thiolane-type, four 2-methylthiolane (and thiane)-type, two 1,2-dithiolane-type, and two 2-oxothiolane-type sulfides, together with ( E )-ajoene and one kujounin-type sulfide from garlic. During this process, structural corrections were made in onionin A group, garlicnin A, and garlicnin B group in some 3,4-dimethylthiolane-type sulfides. Next, hypothetical pathways for the production of the aforementioned sulfides were proposed. Furthermore, it was revealed that a typical 3,4-dimethylthiolane-type sulfide, onionin A 1 obtained from onion, having the isomeric structure of garlicnin B 1 obtained from garlic, decreased tumor proliferation and controlled tumor metastasis. These results showed that onionin A 1 is an effective agent for controlling tumors, and that the antitumor effects observed in vivo are likely caused by reversing the antitumor immune system. Activation of the antitumor immune system by onionin A 1 might be an effective adjuvant therapy for patients with osteosarcoma, ovarian cancer and other malignant tumors.

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