《黄酮化合物解谱》ppt课件

1、13.012.58.07.57.06.56.012.85 s OH-5 8.06 dJ=7.9Hz H-2, 6 7.58 m H-3, 4, 56.94 s H-3 6.53 dJ=1.9Hz H-8 6.23 dJ=1.9Hz H-63754186421OOOHHO白杨素白杨素13.012.58.07.57.06.512.89 s OH-5 7.87 ddJ=1.6, 8.0Hz H-6 7.41 dtJ=1.6, 8.0Hz H-4 7.07 ddJ=2.0, 8.0Hz H-37.06 s H-3 7.01 dtJ=1.6, 8.0Hz H-5 6.48 dJ=2.0Hz H-8 6.

2、22 dJ=2.0Hz H-63754186421OOOHHOHO25, 7, 2-trihydroxyflavone3754186421OOOHOH13.012.58.07.57.06.512.82 s OH-5 7.96 dJ=8.7Hz H-2, 6 7.65 tJ=8.3Hz H-7 7.13 dJ=8.3Hz H-8 6.97 dJ=8.7Hz H-3, 56.90 s H-3 6.79 dJ=8.3Hz H-65, 4-Dihydroxyflavone8.07.57.06.54.03.53754186421OOOMeHO7-Hydroxy-4-methoxyflavone 8.01

3、 dJ=8.9Hz H-2, 6 7.89 dJ=8.7Hz H-5 7.10 dJ=8.9Hz H-3, 5 7.00 dJ=2.1Hz H-8 6.93 ddJ=2.2, 8.7Hz H-66.79 s H-3 3.84 s-OMe 8.58.07.57.06.52-Hydroxy-4-methoxychalcone7.92 d (J=15.4Hz, H-)7.84 d (J=15.4Hz, H-)6.98-7.06 m H-3, -5 7.56 ddJ=1.3, 8.0Hz H-4 8.26 ddJ=1.3, 8.0Hz H-6 7.89 dJ=8.6HzH-2, -6 7.04 dJ=

4、8.6HzH-3 or -5 7.01 dJ=8.6HzH-5 or -3OHOOMe2345623456 12.70 br s3.84 br s12.512.07.06.56.03.0 3.23 tJ=7.4Hz H- 2.77 tJ=7.4Hz H- 12.24 br s H-2 5.82 s H-3 H-52463OHOHOOHOH26 4535 7.03 dJ=8.4Hz H-2, -6 6.67 dJ=8.4Hz H-3, -5Phloretin12.07.06.56.05.53.53.0 5.43 ddJ=2.8, 12.7Hz H-2 3.26 ddJ=12.7, 17.1Hz

5、H-3ax 2.69 ddJ=2.8, 17.1Hz H-3eq 12.15 s 5.90 sH-6, -8 7.32 d J=8.5Hz H-2, 6 6.81 d J=8.5Hz H-3, 5Naringenin2346841OOOHHOOHHeqHaxH12.06.56.05.55.04.5 4.99 d J=11.1Hz H-2 4.51 d J=11.1Hz H-3 11.90 s 5-OH 5.88 dJ=2.0Hz H-6 5.92 dJ=2.0Hz H-8 6.89 s H-2 6.75 sH-5, H-6 2468OOHOOHOHOHOH5 7635Taxifolin化合物化

6、合物黄黄 酮酮黄酮醇黄酮醇异黄酮异黄酮左栏化合物左栏化合物的的7-O-糖苷糖苷二氢黄酮二氢黄酮二氢黄酮醇二氢黄酮醇左栏化合物左栏化合物的的7-O-糖苷糖苷H-66.00 6.20 d6.20 6.40 d5.75 5.95 d5.90 6.10 dH-86.30 6.506.50 6.90 d5.90 6.10 d6.10 6.40 d5, 7-二羟基黄酮类化合物的二羟基黄酮类化合物的H-6和和H-8的化学位移的化学位移低场位移低场位移低场位移低场位移化合物化合物H-5H-6H-8黄黄 酮酮黄酮醇黄酮醇异黄酮异黄酮7.90 8.20 d6.70 7.10 dd6.70 7.00 d二氢黄酮二氢

7、黄酮二氢黄酮醇二氢黄酮醇7.70 7.90 d6.40 6.50 dd6.30 6.40 d7-OH黄酮类化合物的黄酮类化合物的H-5、H-6和和H-8的化学位移的化学位移 ()化合物化合物二二 氢氢 黄黄 酮酮H-2, -67.10 7.30 dH-3, -5二氢黄酮醇二氢黄酮醇异异 黄黄 酮酮7.20 7.40 d7.20 7.50 d查查 耳耳 酮酮橙橙 酮酮7.40 7.60 d7.60 7.80 d6.50 7.10 d黄黄 酮酮黄黄 酮酮 醇醇7.70 7.90 d7.90 8.10 d 4 -氧取代黄酮类化合物的氧取代黄酮类化合物的H-2 ，H-6和和H-3，-5的化学位移的化学

8、位移 ()化化 合合 物物H-2H-6黄黄 酮酮 (3, 4 OH 及及3-OH, 4 -OMe)7.20 7.30 d7.30 7.50黄酮醇黄酮醇 (3, 4 OH 及及3-OH, 4 -OMe)7.50 7.70 d7.60 7.90 d黄酮醇黄酮醇 (3-OMe，4 -OH)7.60 7.80 d7.40 7.60 d黄酮醇黄酮醇 (3, 4 -OH, 3-O-糖糖) 7.20 7.50 d7.30 7.70 d3，4 -二氧取代黄酮类化合物的二氧取代黄酮类化合物的 H-2和和H-6的化学位移的化学位移化合物化合物二氢黄酮二氢黄酮二氢黄酮醇二氢黄酮醇二氢黄酮醇二氢黄酮醇 3-O-糖苷糖

9、苷H-25.00 5.50 dd4.80 5.00 dd5.00 5.60 ddH-3接近接近 2.80 dd4.10 4.30 d4.30 4.60 d二氢黄酮和二氢黄酮醇的二氢黄酮和二氢黄酮醇的H-2和和H-3的化学位移的化学位移 ()168.6 169.8 (s).8 140.7 (d)122.1 122.3 (s)异橙酮类异橙酮类174.5 184.0 (s)160.5 163.2 (s)104.7 111.8 (d)黄酮类黄酮类149.8 155.4 (d)122.3 125.9 (s)异黄酮类异黄酮类147.9 (s).0 (s)黄酮醇类黄酮醇类182.5 182.7 (s)146

10、.1 147.7 (s)111.6 111.9 (d)(=CH-)橙酮类橙酮类188.0 197.0 (s).9 145.4 (d)116.6 128.1 (d)查耳酮类查耳酮类75.0 80.3 (d)42.8 44.6 (t)二氢黄酮类二氢黄酮类82.7 (d)71.2 (d)二氢黄酮醇类二氢黄酮醇类13C NMR谱中黄酮类构造的中央三碳核的信号特征谱中黄酮类构造的中央三碳核的信号特征 化学位移，化学位移，in DMSO-d620010015050197.1161.1159.0153.9150.1146.5129.3125.5116.4115.9113.2102.493.074.560.5

11、56.341.54759528134610623634627-OMe8-OMe3a3b6.62, dd6.75, d6.92, d6.25, s5.70, dd2.80, dd3.18, ddOHOOHHHHOOMeMeOOH13C-1H COSY Spectrum of (2S)-5, 2, 5-trihydroxy-7, 8-dimethoxyflavone197.1161.1159.0153.9150.1146.5129.3125.5116.44115.9113.2102.493.074.560.556.341.5475952813610623634627-OMe8-OMe5-OH*2-

12、OH5-OH*3a3b*12.58.07.57.06.5 12.65-OH 7.79J=8.7Hz2, 6 H 6.93J=8.7Hz3, 5 H 6.42J=2.0Hz8 H 6.22J=2.0Hz6 HR1R2R3R5R4R6OHOHOHOHG1G6G4G3G5G2OH5.55.04.54.03.53.01.0OHOHOOMeOOOHHOOHOOHOHOHOOH1246814115731H NMR Spectrum of Kaempferol 3-O-glucosyl(1-2)-rhamnosideH2OOHOHOOMeOOOHHOOHOOHOHOHOOH1246814115733.003

13、.504.004.505.005.50 3.003.504.004.505.005.50R1G1R2R3G6G2, G5G3, G4 , R4R51H-1H COSY Spectrum of Kaempferol-3-O-glucosyl(12)rhamnosideOHOHOHOH82807876747270686664623.003.203.403.603.804.004.2081.577.577.075.773.571.871.071.061.7R2R5R3R4G2G6G3G5G4OHOHOOMeOOOHHOOHOOHOHOHOOH1246814115731H-13C COSY Spect

14、rum of Kaempferol-3-O-glucosyl(12)rhamnosideG2, G5G3, G4 , R4R5G6R3G1R2OMeHOHOOHOOOOOHOHOHHOHOMeO157.9134.6178.0105.9156.2161.099.5161.894.7130.8115.5115.5130.8160.2101.970.370.871.670.118.098.470.270.471.169.917.6化化 合合 物物糖基糖基H-1黄酮醇黄酮醇 3-O-葡萄糖苷葡萄糖苷5.70 6.00黄酮类黄酮类 7-O-葡萄糖苷葡萄糖苷4.80 5.20黄酮类黄酮类 4-O-葡萄糖苷

15、葡萄糖苷黄酮类黄酮类 5-O-葡萄糖苷葡萄糖苷黄酮类黄酮类 6-及及8-C-葡萄糖苷葡萄糖苷黄酮醇黄酮醇 3-O-鼠李糖苷鼠李糖苷5.00 5.10二氢黄酮醇二氢黄酮醇 3-O-葡萄糖苷葡萄糖苷4.10 4.30二氢黄酮醇二氢黄酮醇 3-O-鼠李糖苷鼠李糖苷4.00 4.20黄酮苷类化合物的糖基黄酮苷类化合物的糖基H-1的化学位移的化学位移苷化位置苷 元 的 苷 化 位 移 平 均 值23456789101234567-O-糖+0.8-1.4+1.1+1.77-O-鼠李糖+0.8-2.4+1.0+1.73-O-糖+9.2-2.1+1.5+0.4+1.0-0.8+1.1-0.3+0.7-0.4+

16、1.53-O-鼠李糖+10.3-1.1+2.0+0.6+1.15-O-葡萄糖-2.8+2.2-6.0-2.7+4.4-3.0+3.2+1.4+4.3-1.3-1.2-0.4-0.8-1.0-1.23 -O-葡萄糖-0.5+0.4+1.6+1.4+0.4+3.24 -O-葡萄糖+0.1+1.0+3.7+0.4+2.0-1.2+1.4黄酮类化合物黄酮类化合物13C NMR 谱苷化位移谱苷化位移12.510.07.55.02.50.00.99, br s6.70, s6.48, s7.53, s6.89, d, J=8.4Hz7.62, d, J=8.4Hz3.86, s4.88, d, J=10.

17、2Hz 5.34, t, J=9.5Hz3.47, m3.49, m3.34, m3.61, m; 3.80, m2.06, m1.25, m1.25, m0.60, t, J=7.2Hz0.69, d, J=6.9HzMeMeOOHOHOOOHHOOHOOMeOOHHaHbHMeMeOOHOHOOOHHOOHOOMeOOHHaHbH7.55.02.50.99, br s6.48, s3.86, s0.69, d, J=6.9Hz2.06, m1.25, m1.25, m0.60, t, J=7.2Hz 5.34, t, J=9.5Hz3.47, m3.49, m3.61, m; 3.80,

18、m3.34, m4.88, d, J=10.2Hz7.53, s6.70, s7.62, d, J=8.4Hz6.89, d, J=8.4Hz161.8MeMeOOHOHOOOHHOOHOOMeOOHHaHbH164.6102.4182.1161.894.6162.7103.2155.6104.2121.7114.1145.9150.1115.7119.670.771.575.770.682.361.356.6174.540.225.711.216.41751501251007550250DEPT Spectrum of Trolliuside IMeMeOOHOHOOOHHOOHOOMeOOHHaHbH23612561234561234581066255233662211OMeOMe6666343, 45522333355441H-1H COSY Spectrum of Trolliuside IMeMeOOHOHOOOHHOOHOOMeOOHHaHbH164.6102.4182.1161.894.6162.7103.