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Resolution and identification of scalemic caged xanthones from the leaf extract of Garcinia propinqua having potent cytotoxicities against colon cancer cells

Journal Article


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Abstract


  • A new scalemic 8,8a-dihydro caged xanthone (1) was isolated from the leaf extract of Garcinia propinqua. Five other known natural products, the three caged xanthones (2, 5 and 6) and the two neocaged xanthones, (3 and 4) were also isolated as scalemic mixtures. Their structures were characterized by spectroscopic methods. The enantiomeric ratios (er) of compounds 1-6 ranged from 1:0.7 to 1:0.9. These compounds were also resolved by semipreparative chiral HPLC. The absolute configurations of (+)-2 and (+)-3 were determined by single-crystal X-ray diffraction analysis using Cu Kα radiation while the absolute configurations of the other compounds were determined by comparisons of their ECD spectra. Compounds (-)-4, (+)-4, (-)-5, (+)-5, and (-)-6 showed potent cytotoxicities against a colon cancer cell line HCT116 with IC 50 values of 2.60, 7.02, 1.47, 3.37, and 4.14μM, respectively, which were better than the standard control doxorubicin (IC 50 9.74μM).

UOW Authors


  •   Sriyatep, Teerayut (external author)
  •   Tantapakul, Cholpisut (external author)
  •   Andersen, Raymond J. (external author)
  •   Patrick, Brian O. (external author)
  •   Pyne, Stephen
  •   Muanprasat, Chatchai (external author)
  •   Seemakhan, Sawinee (external author)
  •   Borwornpinyo, Suparerk (external author)
  •   Laphookhieo, Surat (external author)

Publication Date


  • 2018

Citation


  • Sriyatep, T., Tantapakul, C., Andersen, R. J., Patrick, B. O., Pyne, S. G., Muanprasat, C., Seemakhan, S., Borwornpinyo, S. & Laphookhieo, S. (2018). Resolution and identification of scalemic caged xanthones from the leaf extract of Garcinia propinqua having potent cytotoxicities against colon cancer cells. Fitoterapia, 124 34-41.

Scopus Eid


  • 2-s2.0-85031744074

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=6196&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/5143

Number Of Pages


  • 7

Start Page


  • 34

End Page


  • 41

Volume


  • 124

Place Of Publication


  • Netherlands

Abstract


  • A new scalemic 8,8a-dihydro caged xanthone (1) was isolated from the leaf extract of Garcinia propinqua. Five other known natural products, the three caged xanthones (2, 5 and 6) and the two neocaged xanthones, (3 and 4) were also isolated as scalemic mixtures. Their structures were characterized by spectroscopic methods. The enantiomeric ratios (er) of compounds 1-6 ranged from 1:0.7 to 1:0.9. These compounds were also resolved by semipreparative chiral HPLC. The absolute configurations of (+)-2 and (+)-3 were determined by single-crystal X-ray diffraction analysis using Cu Kα radiation while the absolute configurations of the other compounds were determined by comparisons of their ECD spectra. Compounds (-)-4, (+)-4, (-)-5, (+)-5, and (-)-6 showed potent cytotoxicities against a colon cancer cell line HCT116 with IC 50 values of 2.60, 7.02, 1.47, 3.37, and 4.14μM, respectively, which were better than the standard control doxorubicin (IC 50 9.74μM).

UOW Authors


  •   Sriyatep, Teerayut (external author)
  •   Tantapakul, Cholpisut (external author)
  •   Andersen, Raymond J. (external author)
  •   Patrick, Brian O. (external author)
  •   Pyne, Stephen
  •   Muanprasat, Chatchai (external author)
  •   Seemakhan, Sawinee (external author)
  •   Borwornpinyo, Suparerk (external author)
  •   Laphookhieo, Surat (external author)

Publication Date


  • 2018

Citation


  • Sriyatep, T., Tantapakul, C., Andersen, R. J., Patrick, B. O., Pyne, S. G., Muanprasat, C., Seemakhan, S., Borwornpinyo, S. & Laphookhieo, S. (2018). Resolution and identification of scalemic caged xanthones from the leaf extract of Garcinia propinqua having potent cytotoxicities against colon cancer cells. Fitoterapia, 124 34-41.

Scopus Eid


  • 2-s2.0-85031744074

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=6196&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/5143

Number Of Pages


  • 7

Start Page


  • 34

End Page


  • 41

Volume


  • 124

Place Of Publication


  • Netherlands