Garlicnins B(1), C(1), and D, from the fraction regulating macrophage activation of Allium sativum

Chem Pharm Bull (Tokyo). 2012;60(6):747-51. doi: 10.1248/cpb.60.747.

Abstract

Several novel sulfides from acetone extracts of bulbs of garlic (Allium sativum L.), were identified and investigated. These were named garlicnins B(1) (1), C(1) (2), and D (3), and they were found to have the ability to control macrophage activation. Garlicnins B(1) (1) and C(1) (2) possess a new skeleton of cyclic sulfoxide and their structures of garlicnins B(1) (1) and C(1) (2) were characterized as 3,4-dimethyltetrahydrothiophene-S-oxide derivatives carrying the substitutions of a propenyl and a sulfenic acid, and an allyldithiine and a 1-propene-sulfenic acid (a), respectively. The mechanism of the proposed production of these compounds is discussed. Garlicnin D (3), dithiine-type, was estimated to be derived by addition of (a)+allyl thiosulfenic acid (b) derived from allicin. The identification of these novel sufoxides from onion and garlic accumulates a great deal of new chemistry to the Allium sulfide field, and future pharmacological investigations aid the development of natural, healthy foods and anti-cancer agents that could potentially prevent or combat disease.

MeSH terms

  • Antigens, CD / metabolism
  • Antigens, Differentiation, Myelomonocytic / metabolism
  • Garlic* / chemistry
  • Humans
  • Macrophage Activation / drug effects
  • Receptors, Cell Surface / antagonists & inhibitors
  • Receptors, Cell Surface / metabolism
  • Thiophenes / chemistry*
  • Thiophenes / pharmacology

Substances

  • Antigens, CD
  • Antigens, Differentiation, Myelomonocytic
  • CD163 antigen
  • Receptors, Cell Surface
  • Thiophenes
  • garlicnin B(1)
  • garlicnin C(1)
  • garlicnin D