S-substituted cysteine derivatives and thiosulfinate formation in Petiveria alliacea - Part II

Phytochemistry

Volumn 61, Issue 6, 2002, Pages 675-680

  Kubec, Roman ^b   Kim, Seokwon ^a   Musah, Rabi A ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

6 Hydroxyethiin; Petiveria alliacea; Petivericin; Petiveriin; Phytolaccaceae; S (2 Hydroxyethyl)cysteine; S (2 Hydroxyethyl)cysteine sulfoxide; Thiosulfinate

Indexed keywords

BENZENE DERIVATIVE; BENZYL DERIVATIVE; CYSTEINE; CYSTEINE DERIVATIVE; PETIVERIA ALLIACEA EXTRACT; PLANT EXTRACT; S (2 HYDROXYETHYL)(2 HYDROXYETHANE)PHENYLMETHANETHIOSULFINATE; S (2 HYDROXYETHYL)CYSTEINE; S (2 HYDROXYETHYL)CYSTEINE SULFOXIDE DERIVATIVE; S (2 HYDROXYETHYL)PHENYLMETHANETHIOSULFINATE; S BENZYL(2 HYDROXYETHANE)PHENYLMETHANETHIOSULFINATE; S BENZYLPHENYLMETHANETHIOSULFINATE; SULFINIC ACID DERIVATIVE; SULFUR; THIOSULFINATE; THIOSULFINIC ACIDS; UNCLASSIFIED DRUG;

ARTICLE; CARYOPHYLLACEAE; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MEDICINAL PLANT; METABOLISM; OXIDATION; PETIVERIA ALLIACEA; PLANT ROOT; SPECTROSCOPY;

CARYOPHYLLACEAE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYSTEINE; SPECTRUM ANALYSIS; SULFINIC ACIDS;

PETIVERIA ALLIACEA; PHYTOLACCACEAE;

EID: 0036855513     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(02)00328-X     Document Type: Article

References (22)

1. Adesogan, E.K., 1974. Trithiolaniacin, a novel trithiolan from Petiveria alliacea. J. Chem. Soc. Chem. Commun. 21, 906-907.
2. Ayedoun, M.A., Moudachirou, M., Sossou, P.V., Garneau, F.-X., Gagnon, H., Jean, F.-I., 1998. Volatile constituents of the root oil of Petiveria alliacea L. from Benin. J. Essent. Oil Res. 10, 645-646.
3. Ayodele, E.T., Hudson, H.R., Ojo, I.A.O., Pianka, M., 2000. Organosulfur compounds as potential fungicides: The preparation and properties of some substituted benzyl 2-hydroxyethyl oligosulfides. Phosphorus, Sulfur Silicon Relat. Elem 159, 123-142.
4. Benevides, P.J.C., Young, M.C.M., Giesbrecht, A.M., Roque, N.F., Bolzani, V.S., 2001. Antifungal polysulphides from Petiveria alliacea L. Phytochemistry 57, 743-747.
5. Block. E., 1992. The organosulfur chemistry of the genus Allium-implications for the organic chemistry of sulfur. Angew. Chem., Int. Ed. Engl. 31, 1135-1178.
6. Chatgilialoglu, C., Gilbert, B.C., Gill, B., Sexton, M.D., 1980. Electron spin resonance studies of radicals formed during the thermolysis and photolysis of sulphoxides and thiolsulphonates. J. Chem. Soc. Perkin 2 1141-1150.
7. Furukawa, M., Tsuiji, S., Kojima, Y., Hayashi, S., 1973. The reaction of benzyl phenylmethanethiosulfinate with amines. Chem. Pharm. Bull 21, 2391-2395.
8. Hefner Jr., R.E., Watanabe, P.G., Gehring, P.J., 1975. Fate of inhaled vinyl chloride monomer in rats. Environ. Health Perspect. 11, 85-95.
9. Jones, A.R., Wells, G., 1981. The comparative metabolism of 2-bromoethanol and ethylene oxide in the rat. Xenobiotica 11, 763-770.
10. Kice, J.L., Parham, F.M., Simons, R.M., 1960. The thermal decomposition of thiolsulfonates. J. Am. Chem. Soc. 82, 834-842.
11. Kubec, R., Svobodová, M., Velíšek, J., 1999. Gas chromatographic determination of S-alk(en)ylcysteine sulfoxides. J. Chromatogr. A 862, 85-94.
12. Kubec, R., Musah, R.A., 2001. Cysteine sulfoxide derivatives in Petiveria alliacea. Phytochemistry 58, 981-985.
13. Mata-Greenwood, E., Ito, A., Westenburg, H., Cui, B., Mehta, R.G., Kinghorn, A.D., Pezzuto, J.M., 2001. Discovery of novel inducers of cellular differentiation using HL-60 promyelocytic cells. Anticancer Res. 21, 1763-1770.
14. Nachtomi, E., Alumot, E., Bondi, A., 1966. The metabolism of ethylene dibromide in the rat I. Identification of detoxification products in urine. Israel J. Chem. 4, 239-246.
15. Ratner, S., Clarke, HT., 1937. The action of formaldehyde upon cysteine. J. Am. Chem. Soc. 59, 200-206.
16. Shiraiwa, T., Tadokoro, K., Tanaka, H., Nanba, K., Yokono, N., Shibazaki, K., Kubo, M., Kurokawa, H., 1998. Synthesis of optically active 1,4-thiazane-3-carboxylic acid via optical resolution by preferential crystallization of (RS)-2-amino-3-[(2-chloroethyl)sulfanyl]propanoic acid hydrochloride. Biosci. Biotechnol. Biochem. 62, 2382-2387.
17. Smythe, J.A., 1922. Decomposition of benzyl disulphoxide. J. Chem. Soc. 121, 1400-1405.
18. Sousa, J.R., Demuner, A.J., Pinheiro, J.A., Breitmaier, E., Cassels, B.K., 1990. Dibenzyl trisulphide and trans-N-methyl-4-methoxyproline from Petiveria alliacea. Phytochemistry 29, 3653-3655.
19. Stoll, A., Seebeck, E., 1949. Über die spezifität der alliinase und die synthese mehrerer dem alliin verwandter verbindungen. Helv. Chim. Acta 32, 866-876.
20. Szczepanski, C., Zgorzelak, P., Hoyer, G.-A., 1972. Isolierung, strukturaufklärung und synthese einer antimikrobiell wirksamen substanz aus Petiveria alliacea L. Arzneim.-Forsch. 22, 1975-1976.
21. White, R.C., Dellinger, D., 1985. Photolysis of benzyl toluene-α-thiosulphonate. J. Chem. Res. S 64-65.
22. Ziegler, S.J., Sticher, O., 1989. HPLC of S-alk(en)yl-L-cysteine derivatives in garlic including quantitative determination of (+)-S-allyl-L-cysteine sulfoxide (alliin). Planta Med. 55, 372-378.