Atypical Cyclic Sulfides, Garlicnins G, I, and J, Extracted from &lt;i&gt;Allium sativum&lt;/i&gt;

Ono, M.; Fujiwara, Yukio; Ikeda, Tsuyoshi; Pan, Cheng; El‐Aasr, Mona; Lee, Jong Hyun; Nakano, Daisuke; Kinjo, Junei; Nohara, Toshihiro

doi:10.1248/cpb.c16-00648

Cited by 10 publications

(8 citation statements)

References 20 publications

(23 reference statements)

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“…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.…”

Section: Introductionmentioning

confidence: 99%

Neutrophil Immunomodulatory Activity of Natural Organosulfur Compounds

et al. 2019

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Organosulfur compounds are bioactive components of garlic essential oil (EO), mustard oil, Ferula EOs, asafoetida, and other plant and food extracts. Traditionally, garlic (Allium sativum) is used to boost the immune system; however, the mechanisms involved in the putative immunomodulatory effects of garlic are unknown. We investigated the effects of garlic EO and 22 organosulfur compounds on human neutrophil responses. Garlic EO, allyl propyl disulfide, dipropyl disulfide, diallyl disulfide, and allyl isothiocyanate (AITC) directly activated Ca2+ flux in neutrophils, with the most potent being AITC. Although 1,3-dithiane did not activate neutrophil Ca2+ flux, this minor constituent of garlic EO stimulated neutrophil reactive oxygen species (ROS) production. In contrast, a close analog (1,4-dithiane) was unable to activate neutrophil ROS production. Although 1,3-dithiane-1-oxide also stimulated neutrophil ROS production, only traces of this oxidation product were generated after a 5 h treatment of HL60 cells with 1,3-dithiane. Evaluation of several phosphatidylinositol-3 kinase (PI3K) inhibitors with different subtype specificities (A-66, TGX 221, AS605240, and PI 3065) showed that the PI3K p110δ inhibitor PI 3065 was the most potent inhibitor of 1,3-dithiane-induced neutrophil ROS production. Furthermore, 1,3-dithiane enhanced the phosphorylation of extracellular signal-regulated kinase 1/2 (ERK1/2), glycogen synthase kinase 3 α/β (GSK-3α/β), and cAMP response element binding (CREB) protein in differentiated neutrophil-like HL60 cells. Density functional theory (DFT) calculations confirmed the reactivity of 1,3-dithiane vs. 1,4-dithiane, based on the frontier molecular orbital analysis. Our results demonstrate that certain organosulfur compounds can activate neutrophil functional activity and may serve as biological response modifiers by augmenting phagocyte functions.

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Section: Introductionmentioning

confidence: 99%

Neutrophil Immunomodulatory Activity of Natural Organosulfur Compounds

et al. 2019

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“…Therefore, it can be assumed that the ingredients of Chinese garlic may suppress tumor cell proliferation. In previous studies, the acetone extract of Chinese garlic was separated using silica gel chromatography to obtain linear acyclic sulfide types L-1-L-4, E, and F [15], 3,4-dimethylthiolanetype sulfides, garlicnins A [16], B 1 -B 4 [14,17], and C 1 -C 3 [14,17], and atypical cyclic-type sulfides, garlicnins G, I, and J [18], and their chemical structures were characterized. Furthermore, the activity of a 3,4-dimethylthiolanetype sulfide, onionin A 1 , isolated from onion (Allium cepa L.) [19], corresponding to the isomer of the garlicnin B series, was examined for its ability to inhibit tumor progression in both osteosarcoma and an ovarian cancer mouse model.…”

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confidence: 99%

New cyclic sulfides, garlicnins I2, M, N, and O, from Allium sativum

et al. 2017

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“…Structures of garlicnins and onionins isolated from garlic filtrate was concentrated at 40 °C in vacuum to obtain the extract in a small volume that was partitioned between ethyl acetate and water. The ethyl acetate extractive (5.9 g) was separated by column chromatography on silica gel eluting with n-hexane: acetone (from 6: 1 to 2: 1) to yield 21 new sulfides named garlicnins A (48.2 mg) [12], B 1 (242.0 mg), B 2 (47.2 mg), B 3 (29.8 mg), B 4 (19.3 mg), C 1 (26.4 mg), C 2 (23.4 mg), C 3 (14.6 mg) [13,14], G (17.2 mg), I 1 (17.4 mg) [15], I 2 (15.6 mg) [16], J 1 (17.4 mg) [15], J 2 (19.4 mg) [17], L-1 (47.2 mg), L-2 (19.8 mg), L-3 (19.3 mg), L-4 (23.4 mg) [18], M (21.1 mg) [16], P (18.4 mg) [17], and onionins B 1 (27.4 mg), and B 2 (26.2 mg) [19], together with the known sulfide, (E)-ajoene (279.7 mg) [10], and kujounin A 1 derivative (22.1 mg), which related to kujounin A 1 obtained from Allium fistulosum by Matsuda et al [20]. The structures of the obtained sulfides were characterized using high-resolution fast atom bombardment mass spectroscopy (HR-FABMS), 1 H-NMR, 13 C-NMR, 1 H-1 H NMR correlation spectroscopy (COSY), 1 H-detected heteronuclear correlation through multiplet quantum coherence (HMQC), heteronuclear multiple bond correlation (HMBC) and nuclear Overhauser effect spectroscopy (NOESY).…”

Section: Tablementioning

confidence: 99%

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

et al. 2021

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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 A1 obtained from onion, having the isomeric structure of garlicnin B1 obtained from garlic, decreased tumor proliferation and controlled tumor metastasis. These results showed that onionin A1 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 A1 might be an effective adjuvant therapy for patients with osteosarcoma, ovarian cancer and other malignant tumors.

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

Cited by 10 publications

References 20 publications

Neutrophil Immunomodulatory Activity of Natural Organosulfur Compounds

Neutrophil Immunomodulatory Activity of Natural Organosulfur Compounds

New cyclic sulfides, garlicnins I2, M, N, and O, from Allium sativum

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

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