Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A New Monoterpene Glucoside from Portulaca oleracea

  • Seo, Young-Wan (Division of Ocean Science, Korea Maritime University) ;
  • Shin, Jong-Heon (Natural Products Research Institute, College of Pharmacy, Seoul National University) ;
  • Cha, Hyo-Jun (Division of Ocean Science, Korea Maritime University) ;
  • Kim, You-Ah (Division of Ocean Science, Korea Maritime University) ;
  • Ahn, Jong-Woong (Division of Ocean Science, Korea Maritime University) ;
  • Lee, Burm-Jong (Department of Chemistry, Inje University) ;
  • Lee, Dong-Seok (Department of Biomedical Laboratory Science, Inje University)
  • Published : 2003.10.20
Download PDF
⟨ Previous Next ⟩

Abstract

Three monoterpene glucosides (1-3), including one new compound (3), have been isolated from the methanol extract of Portulaca oleracea. Structures of these compounds were determined to be (3S)-3-O-( ${\Beta}$-Dglucopyranosyl)-3,7-dimethylocta-1,6-dien-3-ol (1), (3S)-3-O-( ${\beta}$-D-glucopyranosyl)-3,7-dimethylocta-1,5-dien-3,7-diol (2) and (3S)-3-O-( ${\beta}$-D-glucopyranosyl)-3,7-dimethyl-7-hydroperoxyocta-1,5-dien-3-ol (3), respectively, by a combination of spectral analyses. Their stereochemistries were established by measurement of NOE and vicinal proton-proton coupling constants as well as comparisons of spectral data with those of previously related compounds.

Keywords

References

  1. Mohamed, A. I.; Hussein, A. S. Plant Foods for Human Nutrition1994, 45, 1. https://doi.org/10.1007/BF01091224
  2. Choi, K.-P.; Jung, S.-W.; Kim, E.-J.; Ham, S.-S. Journal of theEast Asian of Dietary Life 1997, 7, 527.
  3. Ghazanfar, S. A. Handbook of Arabian Medicinal Plants; CRCPress: Boca Raton, FL, 1994; p 176.
  4. Lim, J. P.; Suh, E. S. Korean J. Medicinal Crop Sci. 2000, 8, 189.
  5. Chan, K.; Islam, M.; Kamil, M.; Radhakrishnan, R.; Zakaria, M.N. M.; Habilullah, M.; Attas, A. Journal of Ethnopharmacology2000, 73, 445. https://doi.org/10.1016/S0378-8741(00)00318-4
  6. Lim, M.-K.; Kim, M. Korean J. Soc. Food. Cookery Sci. 2001, 17,565.
  7. Yoon, J.-W.; Ham, S. S.; Jun, H. S. U.S. Pat. 5869060, 1999.
  8. Islam, M. W.; Zakaria, M. N. M.; Radhakrishnan, R.; Liu, X. M.;Chen, H. B.; Chan, K.; Al-Attas, A. J. Pharm. Pharmacol. 2000,52, 258.
  9. Seo, Y.; Shin, J.; Lee, B.-J.; Lee D. S. J. Korean Chem. Soc. 2003,47, 1.
  10. Uchiyama, T.; Miyase, T.; Ueno, A.; Usmanghani, K. Phytochemistry1989, 28, 3369. https://doi.org/10.1016/0031-9422(89)80349-8
  11. Manns, D. Phytochemistry 1995, 39, 1115. https://doi.org/10.1016/0031-9422(95)00108-J
  12. Jung, C. M.; Kwon, H. C.; Seo, J. J.; Ohizumi, Y.; Matsunaga, K.;Saito, S.; Lee, K. R. Chem. Pharm. Bull. 2001, 49, 912. https://doi.org/10.1248/cpb.49.912

Cited by

  1. Forssk. (Boraginaceae) extracts: chemical constituents, antioxidant activity and cytotoxic effect in human cancer cell lines pp.1478-6427, 2018, https://doi.org/10.1080/14786419.2018.1437433
  2. Astonishing diversity of natural surfactants: 7. Biologically active hemi- and monoterpenoid glycosides vol.41, pp.1, 2006, https://doi.org/10.1007/s11745-006-5065-y
  3. A New Monoterpene Glucoside from Portulaca oleracea vol.35, pp.10, 2003, https://doi.org/10.1002/chin.200410167
  4. Portulaca oleracea L.: A Review of Phytochemistry and Pharmacological Effects vol.2015, pp.None, 2015, https://doi.org/10.1155/2015/925631
  5. A New Δ-2-Carene-β-D-Glucopyranoside from Fagonia Longispina vol.12, pp.9, 2017, https://doi.org/10.1177/1934578x1701200901
  6. A Pharmacological Review on Portulaca oleracea L.: Focusing on Anti-Inflammatory, Anti- Oxidant, Immuno-Modulatory and Antitumor Activities vol.22, pp.1, 2019, https://doi.org/10.3831/kpi.2019.22.001
  7. An Unusual Homoisoflavanone from PORTULACA OLERACEA vol.40, pp.6, 2003, https://doi.org/10.1002/bkcs.11732
  8. Evaluation of the Therapeutic Effects of the Hydroethanolic Extract of Portulaca oleracea on Surgical-Induced Peritoneal Adhesion vol.2021, pp.None, 2003, https://doi.org/10.1155/2021/8437753
  9. Water-soluble alkaloids isolated from Portulaca oleracea L. vol.113, pp.None, 2003, https://doi.org/10.1016/j.bioorg.2021.105023