Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Ingacamerounol, A New Flavonol and Other Chemical Constituents from Leaves and Stem Bark of Inga edulis Mart.

  • Tchuenmogne, Aimee M.T. (Department of Organic Chemistry, Faculty of Science, TWAS Research Unit (TRU) of the University of Yaounde I) ;
  • Donfack, Erik V. (Department of Organic Chemistry, Faculty of Science, TWAS Research Unit (TRU) of the University of Yaounde I) ;
  • Kongue, Michel D.T. (Institute of Organic and Biomolecular Chemistry, Georg-August University) ;
  • Lenta, Bruno N. (Department of Chemistry, Higher Teacher Training College, University of Yaounde I) ;
  • Ngouela, Silvere (Department of Organic Chemistry, Faculty of Science, TWAS Research Unit (TRU) of the University of Yaounde I) ;
  • Tsamo, Etienne (Department of Organic Chemistry, Faculty of Science, TWAS Research Unit (TRU) of the University of Yaounde I) ;
  • Sidhu, Navdeep (Department of Structural Chemistry, University of Gottingen) ;
  • Dittrich, Birger (Department of Structural Chemistry, University of Gottingen) ;
  • Laatsch, Hartmut (Institute of Organic and Biomolecular Chemistry, Georg-August University)
  • Received : 2013.07.03
  • Accepted : 2013.09.09
  • Published : 2013.12.20
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Abstract

Keywords

Experimental Section

General. UV/Vis spectra were recorded in neutral, acidic (HCl), and basic (NaOH) MeOH on a Varian CARY (3E) UV/Vis spectrophotometer. The CD spectrum was recorded on a Jasco J-810 spectropolarimeter. The optical rotation was recorded in MeOH on a Jasco P-2000 polarimeter. IR spectra were recorded on a Jasco FT/IR-4100 Fourier-transform infrared spectrometer type A. The 1H NMR spectra were recorded on Varian Mercury-300 (300.141 MHz), Varian VNMRS-300 (300.536 MHz), Varian Inova-500 (499.8 MHz) and Inova-600 (599.744 MHz) spectrometers equipped with 3 mm probes; 13C NMR spectra were measured at 125.707 MHz and 150.821 MHz relatively to TMS as internal standard; shifts are reported as δ values. Electrospray-ionization mass spectrometry (ESIMS) and high-resolution mass spectra (HRESIMS) were recorded on a micrOTOF time-of-flight mass spectrometer (Bruker Daltonics, Bremen/Germany), as well as on an Apex IV7 Tesla Fourier-transform ion cyclotron resonance mass spectrometer (Bruker Daltonics, Billerica, MA/USA). Flash and column chromatography (CC): silica gels (SiO2; 230- 400 and 70-230 mesh; Merck). Pre-coated silica gel 60 F254 aluminum sheets were used for TLC with different mixtures of n-hexane, ethyl acetate, dichloromethane and methanol as eluents; spots were detected using UV lamps (254 and 365 nm) or by spraying with 50% H2SO4 followed by heating at 50-100 ℃.

Plant Material. The stem bark and leaves of I. edulis were collected in January 2010 at Mbalmayo in the Centre Region of the Republic of Cameroon. The plant was identified by Mr. V. Nana, botanist at the National Herbarium (Yaounde, Cameroon), where a voucher specimen (no. 65644 HNC) has been deposited.

Ingacamerounol (1): Yellow powder; molecular formula C17H12O8; 0° (c 0.25, MeOH); UV/Vis (MeOH): λmax (log ε) 218 (4.34), 261 (4.27), 297 (3.86) and 363 (4.22) nm. - UV/Vis (HCl): λmax (log ε) 216 (4.38), 261 (4.28), 298 (3.88) and 363 (4.22) nm. - UV/Vis (NaOH): λmax (log ε) 221 (4.44), 273 (4.38), 323 (3.92) and 408 (4.36) nm; IR λmax 3339, 3081, 1648, 1612, 1557, 1030 cm-1;1H NMR (300 MHz, DMSO-d6) and 13C NMR (125 MHz, DMSO-d6) data, see Table 1; MS ((+)-ESI) m/z: 367.1 [M+Na]+, 711.1 [2M+Na]+, 1055.2 [3M+Na]+, 1399.3 [4M+Na]+. - MS ((-)- ESI) m/z: 343.0 [M-H]-, 687.1 [2M-H]-, 1031.1 [3M-H]-. - HRMS((+)-ESI) m/z: 367.0423 (calcd. 367.0424 for C17H12NaO8, [M+Na]+) and HRMS ((-)-ESI) m/z:343.0458 (calcd. 343.0459 for C17H11O8, [M-H]-).

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