The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure-activity relationship

Phytochemistry

Volumn 71, Issue 2-3, 2010, Pages 312-324

  Shigetomi, Kengo ^a   Shoji, Kazuaki ^b   Mitsuhashi, Shinya ^a   Ubukata, Makoto ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b Toyama Agricultural Research Center   (Japan)

Author keywords

MurA; SAR; Tulipalin; Tuliposide

Indexed keywords

6 TULIPOSIDE B; 6-TULIPOSIDE B; ANTIINFECTIVE AGENT; DRUG DERIVATIVE; GAMMA BUTYROLACTONE; GLUCOSIDE; GLYCOSIDE; HYDROXYBUTYRIC ACID; PLANT EXTRACT; TULIPALIN B;

ARTICLE; BACTERIUM; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; FLOWER; MICROBIOLOGICAL EXAMINATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TULIP;

4-BUTYROLACTONE; ANTI-BACTERIAL AGENTS; BACTERIA; FLOWERS; GLUCOSIDES; GLYCOSIDES; HYDROXYBUTYRATES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PLANT EXTRACTS; STRUCTURE-ACTIVITY RELATIONSHIP; TULIPA;

BACTERIA (MICROORGANISMS); TULIPA;

EID: 73649107917     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2009.10.008     Document Type: Article

References (25)

1. Barbier P., and Benezra C. Allergic α-methylene-γ-butyrolactones. Stereospecific syntheses of (+)- and (-)-γ-methyl-α-methylene-γ-butyrolactones. A study of the specificity of (+)- and (-) enantiomers in inducing allergic contact dermatitis. J. Med. Chem. 25 (1982) 943-946
2. Barbier P., and Benezra C. Allergic 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. 29 (1986) 868-871
3. Christensen L.P. Tuliposides from Alstroemeria revoluta. Phytochemistry 38 (1995) 1371-1373
4. Christensen L.P. A further tuliposide from Alstroemeria revoluta. Phytochemistry 40 (1995) 49-51
5. Christensen L.P. Tuliposides from Tulipa sylvestris and T. turkestanica. Phytochemistry 51 (1999) 969-974
6. Christensen L.P., and Kristiansen K. Isolation and quantification of a new tuliposide (tuliposide D) by HPLC in Alstroemeria. Contact Dermatitis 33 (1995) 188-192
7. Gette M.T., and Marks J.E. Tulip fingers. Arch. Dermatol. 126 (1990) 202-205
8. Guo W., Wu W., Fan N., Wu Z., and Xia C. Synthesis of α-substituted N-aryl acrylamide derivatives through Baylis-Hillman reaction. Synth. Commun. 35 (2005) 1239-1251
9. Iino Y., Tanaka A., and Yamashita K. Plant growth inhibitory activities of synthetic α-methylene butyrolactones. Agr. Biol. Chem. 36 (1972) 2505-2509
10. Kato Y., Shoji K., Ubukata M., Shigetomi K., Sato Y., Nakajima N., and Ogita S. Purification and characterization of tuliposide-converting enzyme from the bulbs of Tulipa gesneriana. Biosci. Biotechnol. Biochem. 73 (2009) 1895-1897
11. Kim C.S., Hara T., Datta P.K., Itoh E., and Horiike M. Insecticidal component in Thunberg spiraea, Spiraea thunbergii, against Thrips palmi. Biosci. Biotechnol. Biochem. 62 (1998) 1546-1549
12. Lahti A. Contact urticaria and respiratory symptoms from tulips and lilies. Contact Dermatitis 14 (1986) 317-319
13. Marks J.G. Allergic contact dermatitis to Alstroemeria. Arch. Dermatol. 124 (1988) 914-917
14. Rastelli G., Rosenfeld R., Reid R., and Santi D.V. Molecular modeling and crystal structure of ERK2-hypothemycin complexes. J. Struct. Biol. 164 (2008) 18-23
15. Shibaoka H., Mitsuhashi M., and Shimokoriyama M. Promotion of adventitious root formation by heliangine and its removal by cysteine. Plant Cell Physiol. 8 (1967) 161-170
16. Shigetomi K., Kishimoto T., Shoji T., and Ubukata M. Synthesis of tulipalin B and 1-O-methyl-6-tuliposide B. Heterocycles 69 (2006) 63-67
17. Shigetomi K., Kishimoto T., Shoji K., and Ubukata M. First total synthesis of 6-tuliposide B. Tetrahedron: Asymmetry 19 (2008) 1444-1449
18. Shoji K., Ubukata M., Momonoi K., Tsuji T., and Morimatsu T. Anther-specific production of antimicrobial tuliposide B in tulips. J. Jpn. Soc. Hort. Sci. 74 (2005) 469-475
19. Slob A. Tulip allergens in Alstroemeria and some other Liliflorae. Phytochemistry 12 (1973) 811-815
20. Slob A., Jekel B., and de Jong B.D. On the occurrence of tuliposides in the Liliiflorae. Phytochemistry 14 (1975) 1997-2005
21. Smith A.B., and Fox R.J. Construction of a C(30-38) dioxabicyclo [3.2.1] octane subtarget for (+)-sorangicin A, exploiting a regio and stereocontrolled acid-catalyzed epoxide ring opening. Org. Lett. 6 (2004) 1477-1480
22. Steinbach A., Scheidig A.J., and Klein C.D. The unusual binding mode of cnicin to the antibacterial target enzyme MurA revealed by X-ray crystallography. J. Med. Chem. 51 (2008) 5143-5147
23. Taillier C., Gille B., Bellosta V., and Cossy J. Synthetic approaches and total synthesis of natural zoapatanol. J. Org. Chem. 70 (2005) 2097-2108
24. Tschesche R., Kämmerer F.-J., and Wulff G. Über die antibitisch wirksamen sustanzen der tulpe (Tulipa gesneriana). Tetrahedron Lett. 6 (1968) 701-706
25. Tschesche R., Kämmerer F.-J., and Wulff G. Über die struktur der antibiotisch aktiven sustanzen der Tulpe (Tulipa gesneriana L.). Chem. Ber. 102 (1969) 2057-2071