POLYPHENOLS AND BIOLOGICAL ACTIVITIES OF Feijoa ...

More documents

Recommendations

Info

106 S.M. El-shenawy et al. (1 H, d, J = 7.7 Hz, H-1), 4.94 (1 H, dd, J = 13, 6 Hz, H-6 a ), 4.58 (1 H, t-like, J = 10 Hz, H-4), 4.03 (1 H, br dd, J = 9.2, 6.2 Hz, H-5), 3.67 (1 H, br d, J = 13 Hz, H-6 b ), 3.55 (1 H, t-like, J = 9.2 Hz, H-3), 3.35 (1 H, t-like, J = 8.4 Hz, H-2). 13 C NMR (75 MHz, DMSO-d 6 ): δ ppm 167.83, 167.09 (C-7```/7``HHDP), 164.62 (C-7` G), 145.62 (C-3`⁄5` G), 144.50, 144.41 (C-6``/6``` HHDP), 144.26. 144.23 (C-4``/4``` HHDP), 139.17 (C-4` G), 135.33, 134.96 (C-5``/5``` HHDP), 124.70, 124.42 (C-2``/2```HHDP), 118.42 (C-1` G), 115.55, 115.23 (1``/1```HHDP), 109.09 (C-2`/6` G), 106.29, 105.51 (C-3``⁄ 3``` HHDP), 94.73 (C-1), 73.82 (C-3), 73.33 (C-5), 71.61 (C- 4/2), 62.74 (C-6); G = galloyl and HHDP = hexahydroxydiphenoyl moieties. Casuarin (4) Brown amorphous powder; R f -values: 0.14 (S 1 ), 0.30 (S 2 ) on PC; it gives dark purple fluorescent spot by short UV-light and dull brown under long UV-light, turned to indigo-red and deep blue colour with NaNO 2 - glacial AcOH and FeCl 3 , respectively. UV λ max (MeOH), nm: 246, 285 sh. 1 H NMR (500 MHz, DMSO-d 6 ): δ ppm 6.44, 6.24, 6.15 (1 H each, s, H-3````/3``/3``` HHDP), 5.38 (1 H, br s, H-1), 5.18 (1 H, br s, H-3), 4.8 (1 H, br s, H-4), 4.65 (1 H, br s, H-2), 4.34 (1 H, br d, J = 9.2 Hz, H-6 a ), 3.91 (1 H, br s, H-5), 3.73 (1 H, br d, J = 10.7 Hz, H-6 b ). 13 C NMR (75 MHz, DMSO-d 6 ): δ ppm 169.27, 168.87, 167.57 (C-7``, C-7````, C- 7```), 163.63 (C-7`), 145.79, 144.92, 144.64, 144.60 (C-6`/6``/6```/6```` HHDP), 144.42, 144.30, 144.11 (C-4``/4```/4```` HHDP), 142.62 (C-4` HHDP), 137.64 (C-5`), 135.68, 134.30, 133.74 (C-5``/5```/5```` HHDP), 126.06 (C-2``), 125.55 (C-2````), 123.56 (C- 2```), 119.35 (C-2`), 115.89 (C-1`), 115.70, 115.41 (2C) (C-1``/1```/1```` HHDP), 114.32 (C-3` HHDP), 106.27 (C-3````), 104.67 (C- 3``), 103.03 (C-3``` HHDP), 75.78 (C-2), 75.33 (C-4), 69.69 (C-3), 67.50 (C-1), 66.91 (C-5), 66.14 (C-6). Castalagin (5) Brown amorphous powder; R f -values: 0.04 (S 1 ), 0.61 (S 2 ) on PC. It gives dark purple fluorescent spot by short UV-light and dull brown under long UV-light, turned to indigo-red and deep blue colour with NaNO 2 - glacial AcOH and FeCl 3 , respectively. UV λmax (MeOH), nm: 246, 288 sh. Negative HRESI-MS/MS: m/z 933.06324 [M-H] ‾ (calcd. 933.06363), (MS 2 ) 914.92332 [M-H- H 2 O] ‾ , 631.06571 [M-H-ellagic acid] ‾ , (MS 3 ) 896.95412 [M-H-2H 2 O] ‾ , (MS 4 ) 878.95503 [M-H-3H 2 O] ‾ , 301.01411 [Ellagic acid-H] ‾ ; 1 H NMR (300 MHz, DMSO-d 6 ): δ ppm 6.62 (1 H, s, H-3``` FLG), 6.52 (1 H, s, H-3```` HHDP), 6.38 (1 H, s, H-3````` HHDP), 5.47 (1 H, d, J = 4.5 Hz, H-1), 5.40 (1 H, br d, J = 7.8 Hz, H-5), 4.91 (1 H, t-like, J = 7.8 Hz, H-4), 4.89 (1 H, dd, J = 12.6, 3 Hz, H-6a), 4.82 (2 H, m, H-3/2), 3.96 (1H, br d, J = 12.6 Hz, H-6b). 13 C NMR (100 MHz, DMSO-d 6 ): δ ppm 168.14, 165.84 (C-7````/C-7````` HHDP), 165.80 (C-7``` FLG), 165.32 (C-7`` FLG), 162.87 (C-7` FLG), 146.40 (C-4``` FLG), 144.85, 144.73 (C-6````/6````` HHDP), 144.46, 144.12 (C-4````/4````` HHDP, 4`/4`` FLG), 143.67, 142.47, 142.35 (C-6`/6``/6``` FLG), 137.14 (C-5``` FLG), 135.75, 135.57 (C-5````/5````` HHDP), 135.11 (C-5`` FLG), 133.20 (C-5``` FLG), 125.91 (C-2`` FLG), 124.80, 123.52 (C-2````/2````` HHDP), 123.42 (C-2``` FLG), 121.10 (C-2` FLG), 115.25, 114.47, 114.25 (each 2C), (C- 1````/1````` HHDP, C-1`/1``/1``` FLG, C-3` FLG), 111.70 (C-3`` FLG), 106.84 (each 2 C), 105.60 (C-3``` FLG, C-3````/3````` HHDP), 72.73 (C-2), 69.86 (C-5), 67.90 (C-4), 66.68 (C-1), 65.99 (C-3), 65.12 (C-6). Ellagic acid (6) Off-white amorphous powder; R f -values: 0.39 (S 1 ), 0.19 (S 2 ) on PC; it gives buff fluorescent spot by long and short UV light, turned to dull yellow fluorescence on exposure to ammonia vapours, greenish yellow with Naturstoff, and faint blue colour with FeCl 3 . UV λ max (MeOH), nm: 215, 256, 362.
Polyphenols and biological activities of <strong>Feijoa</strong> sellowiana Rev. Latinoamer. Quím. 36/3 (2008) 107 Negative HRESI-MS, m/z 300.99789 [M-H] ‾ (calcd. 300.99896). Ellagic acid 4-O-methyl ether (7) Pale yellow amorphous powder; R f -values: 0.29 (S 1 ), 0.30 (S 2 ) on PC; it gives faint mauve fluorescent spot under long and short UV light turned to greenish-yellow with ammonia vapours and faint blue with FeCl 3 . UV λ max (MeOH), nm: 245, 272 sh, 353 sh and 385. 1 H NMR (300 MHz, DMSOd 6 ): δ ppm 7.91 (1 H, s, H-5), 7.33 (1 H, s, H-5`), 3.86 (3 H, s, OCH 3 -3). Avicularin (8) Yellow amorphous powder; R f -values: 0.38 (S 1 ), 0.44 (S 2 ) on PC; it gave dark purple spot by long UV light turned to green with FeCl 3 and orange with Naturstoff reagent. UV λ max (MeOH), nm: 296, 296 sh, 351; (+ NaOMe): 273, 327 sh, 403; (+ NaOAc): 270, 320 sh, 361; (+ NaOAc/ H 3 BO 3 ): 270, 400; (+ AlCl 3 ): 273, 304 sh, 335 sh, 421; (+ AlCl 3 /HCl): 268, 290 sh, 361 sh, 398. Negative HRESI/MS: m/z 433.07730 [M-H] ‾ (calcd.: 433.07763), 867.16187 [2M-H] ‾ , 300.02756 [Mpentoside] ‾ = [quercetin-H] ‾ . 1 H and 13 C NMR data are listed in Table 1. Hyperin (9) Yellow amorphous powder; R f -values: 0.48 (S 1 ), 0.61 (S 2 ) on PC; it gave dark purple spot by long UV light turned to green with FeCl 3 and orange with Naturstoff reagent. UV λ max (MeOH), nm: 261, 359; (+ NaOMe): 273, 411; (+ NaOAc): 265, 374; (+ NaOAc/ H 3 BO 3 ): 262, 374; (+ AlCl 3 ): 252 sh, 260, 270, 408; (+ AlCl 3 /HCl): 252 sh, 260, 270, 364. Negative HRESI/MS: m/z 463.08789 [M-H] ‾ (calcd.: 463.08820), 927.18396 [2M-H] ‾ , 301.02255 [M-deoxyhexoside] ‾ = [quercetin-H] ‾ , (MS 3 ) 178.89877 (C 9 H 7 O 4 , cinnamoyl fragment), 150.89915 (C 6 H 3 O 4 , Table 1: 1 H and 13 C NMR spectral data of 8-10 (DMSO-d 6 , 300 and 75 MHz) Carbon 8 9 10 No 13 C 1 H 13 C 1 H 13 C 1 H C-2 156.91 156.28 157.65 C-3 133.37 133.49 134.58 C-4 177.67 177.46 178.10 C-5 161.18 161.17 161.66 C-6 98.64 6.2 (d, 2.1) 98.68 6.2 (d,2.4) 99.05 6.2 (d,2.4) C-7 164.19 164.06 164.58 C-8 93.53 6.4 (d, 2.1) 93.52 6.4 (d,2.4) 93.98 6.39 (d,2.4) C-9 156.32 156.25 156.80 C-10 103.94 103.92 104.43 C-1` 121.68 121.34 121.09 C-2` 115.53 7.47 (d, 2.1) 115.19 7.58 (d,2.4) 115.82 7.23 (d,2.1) C-3` 145.05 144.78 145.56 C- 4` 148.43 148.43 148.80 C-5` 115.53 6.85 (d, 8.1) 115.59 6.83 (d, 8.7) 116.01 6.86 (d,8.7) C-6` 120.94 7.56 (dd, 8.1, 2.1) 121.10 7.66 (dd, 8.2, 2.4) 121.46 7.27 (dd, 8.7,2.1) C-1`` 107.86 5.58 (d, 1.2) 101.86 5.36 (d,7.8) 102.20 5.25 (d,1.5) C-2`` 82.09 4.15 (dd, 3.6, 1.2) 71.22 3.67-3.26 (m, 70.72 3.97dd (3.3,1.5) H-2``, H-3``, H-4``, H-5``) C-3`` 76.96 3.72 (m) 73.20 70.94 3.77-3.05 (m, H3``, H-4”, H-5”) C-4`` 85.86 3.57 (m) 67.34 71.55 C-5`` 60.66 3.33 (dd, 11.7, 2.75``a) 75.81 70.41 3.26 (dd, 11.7, 6.95``b) C-6`` - 60.15 17.85 0.80 (d, 5.7)
Page 1 and 2: POLYPHENOLS AND BIOLOGICAL ACTIVITI
Page 3: Polyphenols and biological activiti
Page 7 and 8: Polyphenols and biological activiti

POLYPHENOLS AND BIOLOGICAL ACTIVITIES OF Feijoa ...

You also want an ePaper? Increase the reach of your titles

Delete template?

Save as template?