Environmentally benign process for the preparation of antimicrobial α-methylene-β-hydroxy-γ-butyrolactone (tulipalin B) from tulip biomass

Bioscience, Biotechnology and Biochemistry

Volumn 79, Issue 1, 2015, Pages 25-35

  Nomura, Taiji ^a   Hayashi, Emiko ^a   Kawakami, Shohei ^a   Ogita, Shinjiro ^a   Kato, Yasuo ^a  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

Enzymatic process; Tulip; Tulipalin; Tuliposide; Tuliposide converting enzyme

Indexed keywords

ENZYMES; ETHANOL; MICROORGANISMS; PURIFICATION;

CONVERTING ENZYME; ENZYMATIC PROCESS; TULIP; TULIPALIN; TULIPOSIDE;

TRICHLOROETHYLENE;

TULIPA; TULIPA GESNERIANA;

6-TULIPOSIDE B; ALCOHOL; ANTIINFECTIVE AGENT; CARBOXYLESTERASE; CHARCOAL; GAMMA BUTYROLACTONE; GLUCOSIDE; HYDROXYBUTYRIC ACID; IMMOBILIZED ENZYME; PLANT EXTRACT; TULIPALIN B; VEGETABLE PROTEIN;

ANALOGS AND DERIVATIVES; BIOMASS; BIOSYNTHESIS; CHEMISTRY; ENZYMOLOGY; FLOWER; GREEN CHEMISTRY; ISOLATION AND PURIFICATION; METABOLISM; TULIP;

4-BUTYROLACTONE; ANTI-INFECTIVE AGENTS; BIOMASS; CARBOXYLIC ESTER HYDROLASES; CHARCOAL; ENZYMES, IMMOBILIZED; ETHANOL; FLOWERS; GLUCOSIDES; GREEN CHEMISTRY TECHNOLOGY; HYDROXYBUTYRATES; PLANT EXTRACTS; PLANT PROTEINS; TULIPA;

EID: 84924569639     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1080/09168451.2014.946395     Document Type: Article

References (40)

1. Jenecka A, Wyrębska A, Gach K, Fichna J, Janecki T. Natural and synthetic α-methylenelactones and α-methylenelactams with anticancer potential. Drug Discov. Today. 2012;17:561-572.
2. Jun-Tao F, De-Long W, Yong-Ling W, He Y, Xing Z. New antifungal scaffold from a natural pharmacophore: Synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium. Bioorg. Med. Chem. Lett. 2013;23:4393-4397.
3. Cavallito CJ, Haskell T. α-Methylene butyrolactone from Erythronium americanum. J. Am. Chem. Soc. 1946;68:2332-2334.
4. Bergman BHH, Beijersbergen JCM, Overeem JC, Kaars Sijpesteijn A. Isolation and identification of α-methylenebutyrolactone, a fungitoxic substance from tulips. Recl. Trav. Chim. Pays-Bas. 1967;86:709-714.
5. Bergman BHH, Beijersbergen JCM. A fungitoxic substance extracted from tulips and its possible role as a protectant against disease. Neth. J. Plant Pathol. 1968;74:157-162.
6. Verspyck Mijnssen GAW. Pathogenesis and causative agent of "tulip finger". Br. J. Dermatol. 1969;81:737-745.
7. Tschesche R, Kämmerer F-J, Wulff G, Schönbeck F. Über die antibiotisch wirksamen der tulpe (Tulipa gesneriana) [On the antibiotically active substances of the tulip (Tulipa gesneriana)]. Tetrahedron Lett. 1968;9:701-706.
8. Tschesche R, Kämmerer F-J, Wulff G. Über die struktur der antibiotisch aktiven substanzen der tulpe (Tulipa gesneriana L.) [On the structure of antibiotically active substances of the tulip (Tulipa gesneriana L.)]. Chem. Ber. 1969;102: 2057-2071.
9. Beijersbergen JCM. A method for determination of tulipalin A and B concentrations in crude extracts of tulip tissues. Recl. Trav. Chim. Pays-Bas. 1972;91:1193-1200.
10. Beijersbergen JCM, Lemmers CBG. Enzymic and non-enzymic liberation of tulipalin A (α-methylene butyrolactone) in extracts of tulip. Physiol. Plant Pathol. 1972;2:265-270.
11. Schönbeck F, Schroeder C. Role of antimicrobial substances (tuliposides) in tulips attacked by Botrytis spp. Physiol. Plant Pathol. 1972;2:91-99.
12. Mendgen T, Scholz T, Klein CD. Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA. Bioorg. Med. Chem. Lett. 2010;20:5757-5762.
13. Shigetomi K, Shoji K, Mitsuhashi S, Ubukata M. The antibacterial properties of 6-tuliposide B: synthesis of 6-tuliposide B analogues and structure-activity relationship. Phytochemistry. 2010;71:312-324.
14. Shigetomi K, Omoto S, Kato Y, Ubukata M. Asymmetric total synthesis of 6-tuliposide B and its biological activities against tulip pathogenic fungi. Biosci. Biotechnol. Biochem. 2011;75: 718-722.
15. Shigetomi K, Olesen SH, Yang Y, Mitsuhashi S, Schönbrunn E, Ubukata M. MurA as a primary target of tulipalin B and 6-tuliposide B. Biosci. Biotechnol. Biochem. 2013;77:2517-2519.
16. Slob A, Varekamp HQ. Tuliposide contents of tulip (Tulipa) species and cultivars during the flowering stage. Proc. K. Ned. Acad. Wet. C Biol Med. Sci. 1977;80:201-211.
17. Christensen LP, Kristiansen K. Isolation and quantification of tuliposides and tulipalins in tulips (Tulipa) by high-performance liquid chromatography. Contact Dermat. 1999;40:300-309.
18. van Rossum MWPC, Alberda M, van der Plas LHM. Tulipaline and tuliposide in cultured explants of tulip bulb scales. Phytochemistry. 1998;49:723-729.
19. Kato Y, Shoji K, Ubukata M, Shigetomi K, Sato Y, Nakajima N, Ogita S. Purification and characterization of a tuliposideconverting enzyme from bulbs of Tulipa gesneriana. Biosci. Biotechnol. Biochem. 2009;73:1895-1897.
20. Nomura T, Ogita S, Kato Y. A novel lactone-forming carboxylesterase: molecular identification of a tuliposide A-converting enzyme in tulip. Plant Physiol. 2012;159:565-578.
21. Nomura T, Tsuchigami A, Ogita S, Kato Y. Molecular diversity of tuliposide A-converting enzyme in the tulip. Biosci. Biotechnol. Biochem. 2013;77:1042-1048.
22. Hoffmann HMR, Rabe J. Synthesis and biological activity of α-methylene-γ-butyrolactones. Angew. Chem. Int. Ed. Eng. 1985;24:94-110.
23. Jean M, Roch ML, Renault J, Uriac P. Synthesis of a laterally branched polyamine from α-methylene-γ-butyrolactone. Org. Lett. 2005;7:2663-2665.
24. Kuroda M, Yoshida D, Mizusaki S. Bio-antimutagenic effect of lactones on chemical mutagenesis in Escherichia coli. Agric. Biol. Chem. 1986;50:243-245.
25. Kim C-S, Hara T, Datta PK, Itoh E, Horiike M. Insecticidal component in thunberg spiraea, Spiraea thunbergii, against Thrips palmi. Biosci. Biotechnol. Biochem. 1998;62:1546-1549.
26. Agarwal S, Jin Q, Maji S. Biobased polymers from plant-derived tulipalin A. In: Smith PB, Gross RA, editors. Biobased monomers, polymers, and materials, ACS symposium series. Washington (DC): American Chemical Society; 2012. p. 197-212.
27. Slob A. Tulip allergens in Alstroemeria and some other Liliflorae. Phytochemistry. 1973;12:811-815.
28. Barbier P, Benezra C. Allergenic α-methylene-γ-butyrolactones. Study of the capacity of β-acetoxy- and β-hydroxy-α-methylene-γ-butyrolactones to induce allergic contact dermatitis in guinea pigs. J. Med. Chem. 1986;29:868-871.
29. Papageorgiou C, Stampf J-L, Benezra C. Allergic contact dermatitis to tulips: an example of enantiospecificity. Arch. Dermatol. Res. 1988;280:5-7.
30. Tanaka A, Yamashita K. Synthesis of (S)-(+)-methyl β, γ-dihydroxy-α-methylenebutyrate and (S)-(-)-tulipalin B. Agric. Biol. Chem. 1980;44:199-202.
31. Papageorgiou C, Benezra C. Use of enzymic hydrolysis of dimethyl malates for a short synthesis of tulipalin B and of its enantiomer. J. Org. Chem. 1985;50:1144-1145.
32. Ohgiya T, Nishiyama S. Synthesis of (-)-tulipalin B utilizing 2-bromo-1-alkenes conveniently synthesized from the 3-Osubstituted 1,2-dibromoalkane system by regioselective elimination. Heterocycles. 2004;63:2349-2354.
33. Shigetomi K, Kishimoto T, Shoji K, Ubukata M. Synthesis of tulipalin B and 1-O-methyl-6-tuliposide B. Heterocycles. 2006;69:63-67.
34. Shigetomi K, Kishimoto T, Shoji K, Ubukata M. First total synthesis of 6-tuliposide B. Tetrahedron: Asymmetry. 2008;19:1444-1449.
35. Kato Y, Yoshida H, Shoji K, Sato Y, Nakajima N, Ogita S. A facile method for the preparation of α-methylene-γ-butyrolactones from tulip tissues by enzyme-mediated conversion. Tetrahedron Lett. 2009;50:4751-4753.
36. Tang SLY, Smith RL, Poliakoff M. Principles of green chemistry: productivity. Green Chem. 2005;7:761-762.
37. Capello C, Fischer U, Hungerbühler K. What is a green solvent? A comprehensive framework for the environmental assessment of solvents. Green Chem. 2007;9:927-934.
38. Horváth IT, Anastas PT. Innovations and green chemistry. Chem. Rev. 2007;107:2169-2173.
39. Li C-J, Trost BM. Green chemistry for chemical synthesis. Proc. Natl. Acad. Sci. USA. 2008;105:13197-13202.
40. nd ed. Weinheim: Wiley-Blackwell; 2012.