Isolation and identification of tuliposides D and F from tulip cultivars

Taiji NomuraORCID iD: https://orcid.org/0000-0003-4876-9866, Shinjiro Ogita
  • Faculty of Life and Environmental Sciences, Prefectural University of Hiroshima, 5562 Nanatsukacho, Shobara, Hiroshima 727-0023, Japan
  • Search for other articles:
  • degruyter.comGoogle Scholar
and Yasuo Kato
  • Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan
  • Search for other articles:
  • degruyter.comGoogle Scholar

Abstract

6-Tuliposides A (6-PosA) and B (6-PosB) are major defensive secondary metabolites in tulip cultivars (Tulipa gesneriana), having an acyl group at the C-6 position of d-glucose. Although some wild tulip species produce 1,6-diacyl-glucose type of Pos (PosD and PosF), as well as 6-PosA/B, they have not yet been isolated from tulip cultivars. Here, aiming at verifying the presence of PosD and PosF in tulip cultivars, tissue extracts of 25 cultivars were analyzed by high-performance liquid chromatography (HPLC). Although no HPLC peaks for PosD nor PosF were detected in most cultivars, we found two cultivars giving a minute HPLC peak for PosD and the other two cultivars giving that for PosF. PosD and PosF were then purified from petals of cultivar ‘Orca’ and from pistils of cultivar ‘Murasakizuisho’, respectively, and their identities were verified by spectroscopic analyses. This is the first report that substantiates the presence of 1,6-diacyl-glucose type of Pos in tulip cultivars.

    • Supplementary material
  • 1.

    Tschesche R, Kämmerer F-J, Wulff G, Schönbeck F. Über die antibiotisch wirksamen substanzen der tulpe (Tulipa gesneriana). Tetrahedron Lett 1968;9:701–6.

  • 2.

    Tschesche R, Kämmerer F-J, Wulff G. Über die struktur der antibiotisch aktiven substanzen der tulpe (Tulipa gesneriana L.). Chem Ber 1969;102:2057–71.

  • 3.

    Nomura T. Function and application of a non-ester-hydrolyzing carboxylesterase discovered in tulip. Biosci Biotechnol Biochem 2017;81:81–94.

  • 4.

    Christensen LP, Kristiansen K. Isolation and quantification of tuliposides and tulipalins in tulips (Tulipa) by high-performance liquid chromatography. Contact Dermat 1999;40:300–9.

  • 5.

    Kato Y, Shoji K, Ubukata M, Shigetomi K, Sato Y, Nakajima N, et al. Purification and characterization of a tuliposide-converting enzyme from bulbs of Tulipa gesneriana. Biosci Biotechnol Biochem 2009;73:1895–7.

  • 6.

    Nomura T, Ogita S, Kato Y. A novel lactone-forming carboxylesterase: Molecular identification of a tuliposide A-converting enzyme in tulip. Plant Physiol 2012;159:565–78.

  • 7.

    Nomura T, Tsuchigami A, Ogita S, Kato Y. Molecular diversity of tuliposide A-converting enzyme in the tulip. Biosci Biotechnol Biochem 2013;77:1042–8.

  • 8.

    Nomura T, Murase T, Ogita S, Kato Y. Molecular identification of tuliposide B-converting enzyme: a lactone-forming carboxylesterase from the pollen of tulip. Plant J 2015;83:252–62.

  • 9.

    Nomura T, Ueno A, Ogita S, Kato Y. Molecular diversity of tuliposide B-converting enzyme in tulip (Tulipa gesneriana): identification of the root-specific isozyme. Biosci Biotechnol Biochem 2017;81:1185–93.

  • 10.

    Nomura T, Kuchida R, Kitaoka N, Kato Y. Molecular diversity of tuliposide B-converting enzyme in tulip (Tulipa gesneriana): identification of the third isozyme with a distinct expression profile. Biosci Biotechnol Biochem 2018;82:810–20.

  • 11.

    Kato Y, Futanaga T, Nomura T. Substrate specificity of tuliposide-converting enzyme, a unique non-ester-hydrolyzing carboxylesterase in tulip: effects of the alcohol moiety of substrate on the enzyme activity. Bioorg Med Chem Lett 2019;29:664–7.

  • 12.

    Christensen LP. Tuliposides from Tulipa sylvestris and T. turkestanica. Phytochemistry 1999;51:969–74.

  • 13.

    Nomura T, Ogita S, Kato Y. One-step enzymatic synthesis of 1-tuliposide A using tuliposide-converting enzyme. Appl Biochem Biotechnol 2019;188:12–28.

  • 14.

    Wilford R. Tulips: species and hybrids for the gardener. Portland, OR: Timber Press, 2006.

  • 15.

    Nomura T, Hayashi E, Kawakami S, Ogita S, Kato Y. Environmentally benign process for the preparation of antimicrobial α-methylene-β-hydroxy-γ-butyrolactone (tulipalin B) from tulip biomass. Biosci Biotechnol Biochem 2015;79:25–35.

Purchase article
Get instant unlimited access to the article.
$42.00
Price including VAT
Log in
Already have access? Please log in.


Journal + Issues

A Journal of Biosciences: Zeitschrift für Naturforschung C (ZNC) is an international scientific journal for the emerging field of natural and natural-like products. ZNC publishes original research on the isolation, bio-chemical synthesis and bioactivities of natural products, their biochemistry, pharmacology, biotechnology, and biological activity and innovative developed computational methods for predicting their structure and/or function.

Search