The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure-activity relationship. | Semantic Scholar (2024)

Skip to search formSkip to main contentSkip to account menu

Semantic ScholarSemantic Scholar's Logo
@article{Shigetomi2010TheAP, title={The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure-activity relationship.}, author={Kengo Shigetomi and Kazuaki Shoji and Shinya Mitsuhashi and Makoto Ubukata}, journal={Phytochemistry}, year={2010}, volume={71 2-3}, pages={ 312-24 }, url={https://api.semanticscholar.org/CorpusID:11030376}}
  • Kengo Shigetomi, K. Shoji, M. Ubukata
  • Published in Phytochemistry 1 February 2010
  • Chemistry, Medicine

35 Citations

Background Citations

8

Results Citations

1

Figures and Tables from this paper

  • figure 1
  • table 1
  • figure 2
  • table 2
  • figure 3

35 Citations

Identification of tuliposide G, a novel glucoside ester-type tuliposide, and its distribution in tulip
    Taiji NomuraY. Kato

    Biology, Chemistry

    Zeitschrift fur Naturforschung. C, Journal of…

  • 2020

Quantification of PosG in bulbs of 52 types of tulip, including 30 cultivars and 22 wild Tulipa spp.

  • 3
Asymmetric Total Synthesis of 6-Tuliposide B and Its Biological Activities against Tulip Pathogenic Fungi
    Kengo ShigetomiShoko OmotoY. KatoM. Ubukata

    Chemistry, Biology

    Bioscience, biotechnology, and biochemistry

  • 2011

Both the tuliposides and tulipalins showed pigment-inducing activity against Gibberella zeae and inhibitory activity against Fusarium oxysporum f.

  • 17
  • PDF
Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA.
    Thomas MendgenT. ScholzC. Klein

    Chemistry, Medicine

  • 2010
  • 34
A Novel Lactone-Forming Carboxylesterase: Molecular Identification of a Tuliposide A-Converting Enzyme in Tulip1[W]
    Taiji NomuraS. OgitaY. Kato

    Biology, Chemistry

    Plant Physiology

  • 2012

To the knowledge, TgTCEA is the first identified member of the lactone-forming carboxylesterases, specifically catalyzing intramolecular transesterification in the tulip defensive strategy.

  • 21
  • PDF
Molecular identification of tuliposide B-converting enzyme: a lactone-forming carboxylesterase from the pollen of tulip.
    Taiji NomuraT. MuraseS. OgitaY. Kato

    Biology, Chemistry

    The Plant journal : for cell and molecular…

  • 2015

Results indicate that mature TgTCEB1 is specifically localized in plastids of pollen grains, but not in the intracellular spaces of pollen grain, as previously reported.

  • 17
  • PDF
MurA as a Primary Target of Tulipalin B and 6-Tuliposide B
    Kengo ShigetomiS. OlesenYan YangS. MitsuhashiE. SchönbrunnM. Ubukata

    Biology, Chemistry

    Bioscience, biotechnology, and biochemistry

  • 2013

Observations suggest that these compounds induced bacterial cell death not through a MurA malfunction, but in such aMurA-mediated indirect manner as the inhibition of other Mur enzymes.

  • 12
  • PDF
Molecular diversity of tuliposide B-converting enzyme in tulip (Tulipa gesneriana): identification of the third isozyme with a distinct expression profile
    Taiji NomuraRyo KuchidaNaoki KitaokaY. Kato

    Biology, Chemistry

    Bioscience, biotechnology, and biochemistry

  • 2018

Identification of TgTCEB-L explains the PosB-converting activity detected in tissues where T gTCEB1 and Tg TCEB-R transcripts could not be detected, indicating that tulip subtilizes the three TGTCEB isozymes depending on the tissue.

  • 8
  • PDF
UDP-N-acetylglucosamine enolpyruvyl transferase as a potential target for antibacterial chemotherapy: recent developments
    A. GautamP. RishiR. Tewari

    Chemistry, Medicine

    Applied Microbiology and Biotechnology

  • 2011

The present review discusses the structural and functional features ofMurA of bacterial pathogens along with the development of MurA-targeted inhibitors.

  • 36
Molecular diversity of tuliposide B-converting enzyme in tulip (Tulipa gesneriana): identification of the root-specific isozyme
    Taiji NomuraA. UenoS. OgitaY. Kato

    Biology, Environmental Science

    Bioscience, biotechnology, and biochemistry

  • 2017

Tissue-specific isozymes are involved in the conversion of 6-tuliposide B, a major secondary metabolite in tulip, to antibacterial tulipalin B, which encodes a TCEB.

  • 7
  • PDF
Antibacterial Flavonoids against Oral Bacteria of Enterococcus faecalis ATCC 29212 from Sarang Semut (Myrmecodia pendans) and its Inhibitor Activity against Enzyme MurA.
    D. KurniaE. ApriyantiC. SorayaM. Satari

    Medicine, Environmental Science

    Current drug discovery technologies

  • 2018

The study demonstrated that ethyl acetate fraction of Sarang Semut contained antibacterial flavonoids as active constituents that showed activity against E. faecalis, proving the plant's potential in herbal medicine and the development of new antibacterial agent for pathogenic dental caries.

  • 23

...

...

25 References

Anther-specific Production of Antimicrobial Tuliposide B in Tulips
    K. ShojiM. UbukataK. MomonoiT. TsujiTakashi Morimatsu

    Agricultural and Food Sciences

  • 2005

The results suggest that a novel defense strategy evolved in tulips to protect pollens from bacterial pollution in the reproductive process by producing an anther-specific 6-tuliposide B.

  • 17
  • PDF
Tuliposides from Tulipa sylvestris and T. turkestanica
    L. Christensen

    Chemistry

  • 1999
  • 36
Synthesis of tulipalin B and 1-O -methyl-6-tuliposide B
    M. UbukataKengo ShigetomiT. KishimotoK. Shoji

    Chemistry

  • 2006

Toward the total synthesis of 6-tuliposide B, facile synthesis of tulipalin B and l-O-methyl-6-tuliposide B (Methyl 6-O-((S)-3',4'-dihydroxy-2'-methylenebutanoyl)-β-D-glucopyranoside) has been

  • 6
Isolation and quantification of a new tuliposide (tuliposide D) by HPLC in Alstroemeria
    L. ChristensenK. Kristiansen

    Biology, Environmental Science

    Contact dermatitis

  • 1995

From aqueous extracts of flowers, stems and leaves of 1 Brazilian and 15 Chilean Alstroemeria species, the content of a new tuliposide, named tuliposide D, was determined by isocratic reversed‐phase

  • 17
First total synthesis of 6-tuliposide B
    Kengo ShigetomiT. KishimotoK. ShojiM. Ubukata

    Chemistry

  • 2008
  • 9
The unusual binding mode of cnicin to the antibacterial target enzyme MurA revealed by X-ray crystallography.
    A. SteinbachA. ScheidigC. Klein

    Chemistry

    Journal of medicinal chemistry

  • 2008

The structure reveals that MurA has catalyzed the formation of a covalent adduct between cnicin and UNAG, which can be regarded as a noncovalent suicide inhibitor.

  • 32
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
    P. BarbierC. Benezra

    Chemistry, Medicine

    Journal of medicinal chemistry

  • 1986

No cross-reaction was demonstrated between gamma,Gamma-unsubstituted and gamma,gamma-subStituted compounds showing a great specificity of ACD.

  • 19
A further tuliposide from Alstroemeria revoluta
    L. Christensen

    Chemistry

  • 1995
  • 12
Über Glykoside mit lacton-bildendem Aglykon, II. Über die Struktur der antibiotisch aktiven Substanzen der Tulpe (Tulipa gesneriana L.)
    R. TschescheF.-J. KämmererG. Wulff

    Chemistry

  • 1969

Aus Tulipa gesneriana L. wurden zwei antibiotisch aktive Glucoside, 1-Tuliposid A (14a) und 1-Tuliposid B (15a), isoliert, die Acyl-β-D-glucopyranoside der γ-Hydroxy-α-methylen-buttersaure bzw.

  • 81
On the occurrence of tuliposides in the liliiflorae
    A. SlobB. JekelB. D. JongEls G. M. Schlatmann

    Biology, Environmental Science

  • 1975
  • 48

...

...

Related Papers

Showing 1 through 3 of 0 Related Papers

    The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure-activity relationship. | Semantic Scholar (2024)
    Top Articles
    Latest Posts
    Article information

    Author: Annamae Dooley

    Last Updated:

    Views: 6665

    Rating: 4.4 / 5 (45 voted)

    Reviews: 92% of readers found this page helpful

    Author information

    Name: Annamae Dooley

    Birthday: 2001-07-26

    Address: 9687 Tambra Meadow, Bradleyhaven, TN 53219

    Phone: +9316045904039

    Job: Future Coordinator

    Hobby: Archery, Couponing, Poi, Kite flying, Knitting, Rappelling, Baseball

    Introduction: My name is Annamae Dooley, I am a witty, quaint, lovely, clever, rich, sparkling, powerful person who loves writing and wants to share my knowledge and understanding with you.