Isolation and Identification of Sodium 2-Propenyl Thiosulfate from Boiled Garlic (<i>Allium sativum</i>) That Oxidizes Canine Erythrocytes

Yamato, Osamu; Sugiyama, Yuko; Matsuura, Hideyuki; Lee, Keun-Woo; Goto, Koichi; Hossain, Mohammad Alamgir; Maede, Yoshimitsu; Yoshihara, Toshio

doi:10.1271/bbb.67.1594

Cited by 20 publications

(9 citation statements)

References 8 publications

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“…Din-propyl-disulphide (H 7 C 3 S 2 C 3 H 7 ) and allyl propyl disulphide (H 5 C 3 S 2 C 3 H 7 ) have been implicated in onion-induced haemolytic anaemia (Kay, 1983;Fenwick and Hanley, 1985;Houston and Myers, 1993;Gault et al, 1995;Talcott, 2004;Sebastian, 2007) but, recently, more active oxidizing sulphur-containing compounds have been discovered and proposed as causative agents, either in onion (Munday et al, 2003) or in garlic (Yamato et al, 2003) poisoning episodes. The susceptibility to onion intoxication depends on several factors (Talcott, 2004), the hereditary condition resulting in erythrocytes with high concentrations of reduced glutathione and potassium probably being the most studied (Yamato and Maede, 1992;Yamato et al, 1999).…”

Section: Discussionmentioning

confidence: 99%

Heinz body anaemia in two dogs after Catalan spring onion ("calcot") ingestion: a case report

Guitart¹,

Mateu²,

Agullo³

et al. 2008

Vet. Med. - Czech

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Catalan spring onions, or "calcots", are a very popular kind of vegetables obtained by special agronomic practices that avoid photosynthesis and subsequent metabolism by the Allium cepa plants. They have been considered for more than a century harmless for pets, as pleasant odour and sweet taste differ so largely from any other onion that can be ingested by children and adults in huge quantities, up to ~3% body weight, without problems being observed. However, the organosulphur chemicals responsible for oxidative damage to canine red blood cells found in this plant species seem to remain present, as two dogs were confirmed to be poisoned after eating left-over "calcots". Both patients presented haemolytic anaemia with Heinz body formation, and eccentrocytosis. Veterinarians and owners should be aware of the dangers associated with this particular onion variety and type, as it is highly palatable to pets and no effective treatment is currently available.

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Section: Discussionmentioning

confidence: 99%

Heinz body anaemia in two dogs after Catalan spring onion ("calcot") ingestion: a case report

Guitart¹,

Mateu²,

Agullo³

et al. 2008

Vet. Med. - Czech

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“…Other studies showed that garlic had radiation‐protective effects in the liver and lungs of rats (Jaiswal & Bordia, ). Sodium 2‐propenyl thiosulfate, NaC 3 H 5 O 3 S (2PTS) and n‐propyl thiosulfate (C 6 H 14 O 3 S 2 , NPTS), two garlic and onion‐derived agents (Yamato et al, ), which cause hemolytic anemia in dogs, have beneficial effects on humans including tumor growth inhibition (Chang, Yamato, Yamasaki, Ko, & Maede, ; Sabelli et al, ), improving leukocyte ability (Nepravishta et al, ) and stimulatory effects on phase II detoxifying enzymes (Chang et al, ). However, they do not cause anemia in humans (Chang, Yamato, Sakai, Yamasaki, & Maede, ; Chang, Yamato, Yamasaki, & Maede, ).…”

Section: A Sativummentioning

confidence: 99%

Allium vegetables for possible future of cancer treatment

Asemani

Zamani

Bayat

et al. 2019

Phytotherapy Research

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Natural resources such as plants are an upright curing option in treating cancers and reducing the side effects of current therapeutic modalities. Allium genus vegetables are of the most interesting herbs in restricting cancers that includes garlic, onions, leeks, chives, and shallots. These plants have been exploited in folk medicine because of their beneficial health effects in improving numerous diseases. The phytochemical analysis of various Allium genus members showed that, to date, 16 species have proved potential anticancer properties due to the accumulation of various sulfur and organic compounds like S‐allyl mercaptocysteine, quercetin, flavonoids, and ajoene. These compounds with various mechanisms such as hindering cell cycle, inhibiting signaling pathways, inducing apoptosis, and antioxidant activity interfere with diverse stages of formation, growth, differentiation, and metastasis of cancer cells. Similar to garlic and onion, other species have exhibited anticancer activities, so that active natural molecules extracted from them might serve as possible anticancer agents. Therefore, evaluating the main ingredients and studying their anticancer mechanisms are of great importance. In this review, we aim to summarize the available data on anticancer mechanisms of 16 species of Allium genus and their major compounds to assist further researches on the treatment and prevention of cancers.

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“…In particular, we studied the interaction of 2‐PTS with rhodanese and investigated the effect of this OSC on the expression and activity of rhodanese. Sodium 2‐propenyl thiosulfate is present in aqueous garlic extract [28] and has an anti‐aggregator effect in vitro on both canine and human platelets as a result of the inhibition of cyclooxygenase activity [29]. The antitumor effect of 2‐PTS, resulting from induction of the apoptosis process, has been recently investigated [7].…”

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confidence: 99%

Rhodanese–thioredoxin system and allyl sulfur compounds

et al. 2008

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Sodium 2-propenyl thiosulfate, a water-soluble organo-sulfane sulfur compound isolated from garlic, induces apoptosis in a number of cancer cells. The molecular mechanism of action of sodium 2-propenyl thiosulfate has not been completely clarified. In this work we investigated, by in vivo and in vitro experiments, the effects of this compound on the expression and activity of rhodanese. Rhodanese is a protein belonging to a family of enzymes widely present in all phyla and reputed to play a number of distinct biological roles, such as cyanide detoxification, regeneration of iron-sulfur clusters and metabolism of sulfur sulfane compounds. The cytotoxic effects of sodium 2-propenyl thiosulfate on HuT 78 cells were evaluated by flow cytometry and DNA fragmentation and by monitoring the progressive formation of mobile lipids by NMR spectroscopy. Sodium 2-propenyl thiosulfate was also found to induce inhibition of the sulfurtransferase activity in tumor cells. Interestingly, in vitro experiments using fluorescence spectroscopy, kinetic studies and MS analysis showed that sodium 2-propenyl thiosulfate was able to bind the sulfur-free form of the rhodanese, inhibiting its thiosulfate:cyanide-sulfurtransferase activity by thiolation of the catalytic cysteine. The activity of the enzyme was restored by thioredoxin in a concentration-dependent and time-dependent manner. Our results suggest an important involvement of the essential thioredoxin-thioredoxin reductase system in cancer cell cytotoxicity by organo-sulfane sulfur compounds and highlight the correlation between apoptosis induced by these compounds and the damage to the mitochondrial enzymes involved in the repair of the Fe-S cluster and in the detoxification system.

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Isolation and Identification of Sodium 2-Propenyl Thiosulfate from Boiled Garlic (Allium sativum) That Oxidizes Canine Erythrocytes

Cited by 20 publications

References 8 publications

Heinz body anaemia in two dogs after Catalan spring onion ("calcot") ingestion: a case report

Heinz body anaemia in two dogs after Catalan spring onion ("calcot") ingestion: a case report

Allium vegetables for possible future of cancer treatment

Rhodanese–thioredoxin system and allyl sulfur compounds

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