Cyclic Sulfoxides-Garlicnins K₁, K₂, and H₁-Extracted from <i>Allium sativum</i>

Abstract

Newly identified cyclic sulfoxides-garlicnins K 1 (1), K 2 (2), and H 1 (3)-were isolated from the acetone extracts of the bulbs of garlic, Allium sativum. Garlicnin H 1 (3) demonstrated potential to suppress tumor cell proliferation by regulating macrophage activation. The structures of garlicnins K 1 and K 2 , 3,4-dimethyl-5-allyl-tetrahydrothiophen-2-one-S-oxides, and the structure of garlicnin H 1 , 3-carboxy-3-hydroxy-4-methyl-5-allylsulfoxide-tetrahydrothiophen-2-(ethane-1,2-diol)-S-oxide were characterized by spectroscopic analysis.

Neutrophil Immunomodulatory Activity of Natural Organosulfur Compounds

“…Approximately 100 organosulfur compounds have been identified in garlic EO from Allium sativum , with diallyl sulfide, diallyl disulfide, allyl methyl sulfide, and diallyl trisulfide as the principal compounds [20]. Moreover, novel sulfides called garlicnins have been isolated from Allium sativum L. and were shown to modulate macrophage activity [21,22,23]. However, the effects of volatile organosulfur compounds from garlic EO on neutrophil functions have not been thoroughly examined.…”

Atypical Cyclic Sulfides, Garlicnins G, I, and J, Extracted from <i>Allium sativum</i>

“…Therefore, it can be assumed that the ingredients of garlic may exhibit suppress tumor cell proliferation. [6][7][8][9][10][11][12][13] In previous studies, the acetone extract of garlic was separated using silica gel chromatography to obtain linear acyclic sulfide types L-1-L-4, E, and F, 14) and cyclic sulfoxides, garlicnins A, 15) B 1 -B 4 , 13,16) C 1 -C 3 , 13,16) D, 13) K 1,2 , and H 1 , 17) and their chemical structures were characterized. Furthermore, the activity of cyclic sulfoxide, onionin A 1 isolated from onion (Allium cepa L.), 18) corresponding to the isomer of garlicnin B series, was examined for its ability to inhibit tumor progression in both osteosarcoma and ovarian cancer mouse model.…”

“…1) spectroscopy. Taking into consideration the above mentioned by HR-FAB-MS and the fact that other garlicnins consist of a combination of an allyl sulfenic acid and an allyl thiosulfenic acid derived from allicin, [13][14][15][16][17][18] 1 was deduced to be composed of one mole each of the allyl sulfenic acid, allyl group, and allyl thiosulfenic acid. It was also deduced that the allyl sulfenic acid was situated adjacent to the carbon at δ 73.4 and that the thiosulfenic acid would form a 1,2-dithiolane ring.…”

New Sulfoxide-Containing Derivatives from the Resin of Ferula sinkiangensis

“…Sulfoxide-containing derivatives are not widespread in nature and mostly restricted to cyclic and acyclic sulfoxides from Allium spe-cies [1][2][3][4][5][6][7][8], as well as polypeptide sulfoxides [9,10], β-carboline alkaloid sulfoxides [11], polysulfides [12], and other compounds [13] from marine sponges, cyanobacteria, and tunicates. These metabolites have displayed biological activities such as regulating macrophage activation [3] and cytotoxicity against human lung cancer cells NCI-H460 [12], murine leukemia cells P388 and L1210, and human epidermoid carcinoma cells KB [13].…”