Synthesis of (±) sulphoraphene

Balenović, K.; Deljac, A.; Monković, Ivo; Štefanac, Z.

doi:10.1016/s0040-4020(01)82133-5

Cited by 11 publications

(5 citation statements)

References 11 publications

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“…The closely related olefin sulforaphene [4-isothiocyanato-(1R)-(methylsulfinyl)-1-(E)-butene (CAS 2404-46-8)] has been isolated from radish seeds and other plants (33,34) and has also been synthesized (35,36).…”

Section: H3cmentioning

confidence: 99%

A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure.

Zhang

Talalay

Cho

et al. 1992

Proc. Natl. Acad. Sci. U.S.A.

1,532

1,027

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Consumption of vegetables, especially crucifers, reduces the risk of developing cancer. Although the mechanisms of this protection are unclear, feeding of vegetables induces enzymes of xenobiotic metabolism and thereby accelerates the metabolic disposal of xenobiotics. Induction of phase II detoxication enzymes, such as quinone reductase [NAD(P)H:(quinone-acceptor) oxidoreductase, EC 1.6.99.2] and glutathione S-transferases (EC 2.5.1.18) in rodent tissues affords protection against carcinogens and other toxic electrophiles. To determine whether enzyme induction is responsible for the protective properties of vegetables in humans requires isolation of enzyme inducers from these sources. By monitoring quinone reductase induction in cultured murine hepatoma cells as the biological assay, we have isolated and identified (-)-1-isothiocyanato-(4R)-(methylsulfinyl)butane [CH3-SO-(CH2)4-NCS, sulforaphane] as a major and very potent phase II enzyme inducer in SAGA broccoli (Brassica oleracea italica). Sulforaphane is a monofunctional inducer, like other anticarcinogenic isothiocyanates, and induces phase II enzymes selectively without the induction of aryl hydrocarbon receptordependent cytochromes P-450 (phase I enzymes). To elucidate the structural features responsible for the high inducer potency of sulforaphane, we synthesized racemic sulforaphane and analogues differing in the oxidation state of sulfur and the number of methylene groups: CHSO5(CH2)n-NCS, where m = 0, 1, or 2 and n = 3, 4, or 5, and measured their inducer potencies in murine hepatoma cells. Sulforaphane is the most potent inducer, and the presence of oxygen on sulfur enhances potency. Sulforaphane and its sulfide and sulfone analogues induced both quinone reductase and glutathione transferase activities in several mouse tissues. The induction of detoxication enzymes by sulforaphane may be a significant component of the anticarcinogenic action of broccoli.Individuals who consume large amounts of green and yellow vegetables have a lower risk of developing cancer (1-3). Feeding of such vegetables to rodents also protects against chemical carcinogenesis (4, 5), and it results in the induction in many tissues of phase II § enzymes-e.g., quinone reductase [QR; NAD(P)H:(quinone-acceptor) oxidoreductase, EC 1.6.99.2] and glutathione S-transferases (EC 2.5.1.18) (11-17). Although much evidence suggests that induction of these enzymes is a major mechanism responsible for this protection (18)(19)(20), the precise role of enzyme induction in protection of humans requires clarification. The preceding report (21) shows that measurement of QR activity in Hepa lclc7 murine hepatoma cells provides a rapid, reliable, and convenient index of phase II enzyme inducer activity in vegetables. Using this assay (21-24), we found that cruciferous vegetables (broccoli, cauliflower, mustard, cress, brussels sprouts) were a rich source of inducer activity. We chose to investigate broccoli (Brassica oleracea italica) specifically because it is consumed in substantial quant...

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Section: H3cmentioning

confidence: 99%

A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure.

Zhang

Talalay

Cho

et al. 1992

Proc. Natl. Acad. Sci. U.S.A.

1,532

1,027

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“…Rotations of such compounds in the optically pure state are generally high (see text, e.g., Table I). The [a]o values of the sulfoxides obtained in the asymmetric oxidations using peracids75 [77][78][79][80] were uniformly low and generally ranged from 1 to 5°. Taking 5 % as a conservative upper limit for the optical purity of the sulfoxides produced in these asymmetric oxidations, * of the diastereomeric transition states is ca.…”

Section: Viii)mentioning

confidence: 99%

Absolute Configuration and Optical Rotatory Power of Sulfoxides and Sulfinate Esters^1,2

Mislow¹,

Green²,

Laur³

et al. 1965

J. Am. Chem. Soc.

297

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thoroughly extracted with 6 N hydrochloric acid, the acidic extract was made strongly alkaline by addition of potassium carbonate, and this basic solution was extracted with ether. After drying with anhydrous magnesium sulfate the ether was carefully distilled off leaving a small quantity (ca. 200 mg.) of a white crystalline material with an infrared spectrum identical with that of urethan.In a similar irradiation of a more concentrated solution of I in cyclohexane (1:10 M ratio) a small amount of diethyl hydrazodiformate (IX) was found.Attempted Radical-Initiated Decomposition of Ethyl Azidoformate in Cyclohexane. In a water bath of 49 ± 1°, a solution of 1.060 g. (9 X 10-3 mole) of redistilled ethyl azidoformate in 125 ml. of purified cyclohexane was placed in the flask, and the system was flushed with purified nitrogen and then sealed. A total of about 1.8 X 10-2 moles of diethyl peroxydi-carbonate67 was injected in portions over a 4-day period producing a slow evolution of an unidentified gas; the volume evolved at various intervals is re-(4) R.

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“…However, these analogs include iberin b) and alyssin c) ( Karrer et al, 1950 ) with a methylsulfonyl group, ibertin d) ( Kjær et al, 1955a ), erucin e) ( Kjær and Gmelin, 1955 ) and berteroin f) ( Kjær et al, 1955b ) with a methylsulfonyl group, and cheirolin g) ( Schneider, 1908 ) and erysolin h) ( Schneider and Kaufmann, 1912 ) with a methylsulfonyl group. The α,β-unsaturated analog of sulforaphene i) is also known ( Balenović et al, 1966 ) ( Figure 3 ). However, researchers have not achieved satisfactory biological activity regardless of whether they converted the sulfoxide group in SFN structure into sulfones or sulfide in methyl mercaptan groups, or substituted sulfoxides with methylene or carbonyl groups, or changed the number of methylene units from 4 to 3 or 5.…”

Section: Sulforaphane and Its Enantiomers And Analoguesmentioning

confidence: 99%

Sulforaphane and bladder cancer: a potential novel antitumor compound

Zuo,

Chen,

Liao

et al. 2023

Front. Pharmacol.

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Bladder cancer (BC) is a common form of urinary tract tumor, and its incidence is increasing annually. Unfortunately, an increasing number of newly diagnosed BC patients are found to have advanced or metastatic BC. Although current treatment options for BC are diverse and standardized, it is still challenging to achieve ideal curative results. However, Sulforaphane, an isothiocyanate present in cruciferous plants, has emerged as a promising anticancer agent that has shown significant efficacy against various cancers, including bladder cancer. Recent studies have demonstrated that Sulforaphane not only induces apoptosis and cell cycle arrest in BC cells, but also inhibits the growth, invasion, and metastasis of BC cells. Additionally, it can inhibit BC gluconeogenesis and demonstrate definite effects when combined with chemotherapeutic drugs/carcinogens. Sulforaphane has also been found to exert anticancer activity and inhibit bladder cancer stem cells by mediating multiple pathways in BC, including phosphatidylinositol-3-kinase (PI3K)/protein kinase B (Akt)/mammalian target of rapamycin (mTOR), mitogen-activated protein kinase (MAPK), nuclear factor kappa-B (NF-κB), nuclear factor (erythroid-derived 2)-like 2 (Nrf2), zonula occludens-1 (ZO-1)/beta-catenin (β-Catenin), miR-124/cytokines interleukin-6 receptor (IL-6R)/transcription 3 (STAT3). This article provides a comprehensive review of the current evidence and molecular mechanisms of Sulforaphane against BC. Furthermore, we explore the effects of Sulforaphane on potential risk factors for BC, such as bladder outlet obstruction, and investigate the possible targets of Sulforaphane against BC using network pharmacological analysis. This review is expected to provide a new theoretical basis for future research and the development of new drugs to treat BC.

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Synthesis of (±) sulphoraphene

Cited by 11 publications

References 11 publications

A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure.

A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure.

Absolute Configuration and Optical Rotatory Power of Sulfoxides and Sulfinate Esters^1,2

Sulforaphane and bladder cancer: a potential novel antitumor compound

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Synthesis of (±) sulphoraphene

Cited by 11 publications

References 11 publications

A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure.

A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure.

Absolute Configuration and Optical Rotatory Power of Sulfoxides and Sulfinate Esters1,2

Sulforaphane and bladder cancer: a potential novel antitumor compound

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Absolute Configuration and Optical Rotatory Power of Sulfoxides and Sulfinate Esters^1,2