睡菜醋酸乙酯部位化学成分及其神经保护作用研究（二）

3 结果与分析

3.1 结构鉴定

化合物1：白色粉末，睡菜神经EI-MS：m/z 368 +，醋酸成分分子式为C17H20O9。乙酯研究1H NMR (400 MHz,部位保护 DMSO-d6) δ: 7.51 (1H, d, J = 15.9 Hz, H-7′), 7.06 (1H, d, J = 1.9 Hz, H-2′), 7.02 (1H, dd, J = 8.1, 1.9 Hz, H-6′), 6.78 (1H, d, J = 8.1 Hz, H-5′), 6.28 (1H, d, J = 15.9 Hz, H-8′), 4.74 (1H, m, H-4), 4.08 (1H, m, H-5), 3.95 (1H, m, H-3), 3.63 (3H, s, -OCH3), 1.81～2.09 (4H, m, H-2, 6)；13C NMR (100 MHz, DMSO-d6) δ: 173.7 (C-7), 166.5 (C-9′), 148.5 (C-4′), 145.6 (C-7′), 144.8 (C-3′), 125.7 (C-1′), 121.3 (C-6′), 115.9 (C-5′), 114.7 (C-2′), 114.5 (C-8′), 75.6 (C-4), 73.5 (C-1), 65.4 (C-5), 64.5 (C-3), 51.7 (-OCH3), 40.9 (C-2), 38.1 (C-6)。以上数据与文献报道一致，化学故鉴定该化合为4-O-咖啡酰奎尼酸甲酯。作用

化合物2：白色粉末，睡菜神经EI-MS：m/z 368 +，醋酸成分分子式为C17H20O9。乙酯研究1H NMR (400 MHz,部位保护 CD3OD) δ: 7.51 (1H, d, J = 15.9 Hz, H-7′), 7.05 (1H, d, J = 1.9 Hz, H-2′), 6.95 (1H, dd, J = 8.1, 1.9 Hz, H-6′), 6.79 (1H, d, J = 8.1 Hz, H-5′), 6.20 (1H, d, J = 15.9 Hz, H-8′), 5.26 (1H, m, H-3), 4.13 (1H, m, H-5), 3.72 (1H, dd, J = 7.5, 3.1 Hz, H-4), 3.69 (3H, s, -OCH3), 2.00～2.23 (4H, m, H-2, 6)；13C NMR (100 MHz, CD3OD) δ: 175.5 (C-7), 168.3 (C-9′), 149.6 (C-4′), 147.4 (C-7), 146.6 (C-3′), 127.5 (C-1′), 123.1 (C-6′), 116.2 (C-5′), 115.2 (C-2′), 115.0 (C-8′), 75.7 (C-1), 72.3 (C-4), 72.1 (C-3), 70.1 (C-5), 53.0 (-OCH3), 38.1 (C-6), 37.6 (C-2)。以上数据与文献报道一致，化学故鉴定该化合物为绿原酸甲酯。作用

化合物3：白色粉末，睡菜神经EI-MS：m/z 354+，醋酸成分分子式为C18H18O9。乙酯研究1H NMR (400 MHz, CD3OD) δ: 7.58 (1H, d, J = 15.9 Hz, H-7′), 7.02 (1H, d, J = 2.0 Hz, H-2′), 6.95 (1H, dd, J = 8.1, 2.0 Hz, H-6′), 6.76 (1H, d, J = 8.0 Hz, H-5′), 6.32 (1H, t, J = 15.9 Hz), 5.35 (1H, m, H-3), 4.15 (1H, m, H-5), 3.65 (1H, dd, J = 8.5, 3.4 Hz, H-4), 1.96-2.22 (4H, m, H-2, 6)；13C NMR (100 MHz, CD3OD) δ: 178.3 (C-7), 169.1 (C-9′), 149.5 (C-4′), 146.6 (C-7′), 146.6 (C-3′), 127.8 (C-1′), 122.8 (C-6′), 116.5 (C-5′), 115.9 (C-8′), 115.1 (C-2′), 75.5 (C-1), 74.8 (C-4), 73.1 (C-3), 68.3 (C-5), 41.6 (C-6), 36.6 (C-2)。以上数据与文献报道一致，故鉴定该化合物为绿原酸。

化合物4：白色粉末，EI-MS：m/z 220 +，分子式为C11H10O5。1H NMR (400 MHz, CD3OD) δ: 7.89 (1H, d, J = 9.5 Hz, H-4), 6.77 (1H, s, H-5), 6.32 (1H, d, J = 9.5 Hz, H-3), 3.81 (3H, s, 6-OCH3), 3.77 (3H, s, 7-OCH3)；13C NMR (100 MHz, CD3OD) δ: 160.3 (C-2), 149.9 (C-6), 144.9 (C-4), 140.3 (C-7), 138.5 (C-9), 138.4 (C-8), 114.6 (C-3), 114.5 (C-10), 100.4 (C-5), 60.7 (7-OCH3), 56.1 (6-OCH3)。以上数据与文献报道一致，故鉴定该化合物为异秦皮素。

化合物5：白色粉末，EI-MS：m/z 222 +，分子式为C11H10O5。1H NMR (400 MHz, CD3OD) δ: 7.83 (1H, d, J = 9.5 Hz, H-4), 6.91 (1H, s, H-5), 6.20 (1H, d, J = 9.5 Hz, H-3), 3.94 (3H, s, 6-OCH3), 3.88 (3H, s, 8-OCH3)。13C NMR (400 MHz, CD3OD)δ: 163.4 (C-2), 147.8 (C-8), 146.6 (C-4), 146.3 (C-9), 144.8 (C-7), 136.7 (C-8), 112.2 (C-3), 112.1 (C-10), 104.9 (C-5), 61.7 (8-OCH3), 56.7 (6-OCH3)。以上数据与文献报道一致，故鉴定该化合物为异嗪皮啶。

化合物6：白色无定形粉末，EI-MS：m/z 538 +，分子式为C26H34O12。1H NMR (400 MHz, CD3OD) δ: 7.14 (1H, d, J = 8.2 Hz, H-5), 7.12 (1H, d, J = 1.9 Hz, H-2), 7.02 (1H, d, J = 1.7 Hz, H-2′), 6.97 (1H, dd, J = 8.2, 1.9 Hz, H-6), 6.87 (1H, dd, J = 8.1, 1.7 Hz, H-6′), 6.78 (1H, d, J = 8.1 Hz, H-5′), 4.98 (1H, d, J = 8.1 Hz, H-7′), 4.93 (1H, d, J = 8.4 Hz, H-7), 4.89 (1H, d, J = 7.6 Hz, H-1′′), 3.89 (3H, s, 3-OCH3), 3.88 (3H, s, 3′-OCH3), 3.56～3.73 (4H, m, H-9, 9′), 2.32 (2H, m, H-8, 8′)；13C NMR (100 MHz, CD3OD) δ: 151.1 (C-3), 149.2 (C-3′), 147.6 (C-4), 147.4 (C-4′), 138.8 (C-1), 134.7 (C-1′), 120.5 (C-6), 120.3 (C-6′), 118.1 (C-5), 116.2 (C-5′), 111.7 (C-2), 111.2 (C-2′), 103.0 (C-1′′), 84.9 (C-7′), 84.2 (C-7), 78.2 (C-5′′), 77.9 (C-3′′), 74.4 (C-2′′), 71.4 (C-4′′), 62.6 (C-2′′), 61.9 (C-9), 61.7 (C-9′), 56.8 (3-OCH3), 56.5 (3′-OCH3), 55.4 (C-8′), 55.2 (C-8)；以上数据与文献报道一致，故鉴定该化合物为7R,7′R,8S,8′S-(＋)-新-橄榄脂素-4-O-β-D-吡喃葡萄糖苷。

化合物7：白色无定形粉末，EI-MS：m/z 552 +，分子式为C27H36O12。1H NMR (400 MHz, CD3OD) δ: 6.77 (1H, d, J = 1.8 Hz, H-2′), 6.71 (1H, d, J = 8.0 Hz, H-5′), 6.66 (2H, s, H-2, 6), 6.61 (1H, dd, J = 8.0, 1.8 Hz, H-6′), 4.86 (1H, d, J = 7.6 Hz, H-1′′), 4.75 (1H, d, J = 7.0 Hz, H-7), 3.99 (1H, m, H-9′a), 3.88 (1H, m, H-9a), 3.84 (6H, s, 3, 5-OCH3), 3.82 (3H, s, 3′-OCH3), 3.71 (1H, m, H-9′b), 3.58 (1H, d, J = 7.5 Hz, H-7′), 2.88 (1H, dd, J = 13.4, 5.1 Hz, H-7′a), 2.67 (1H, m, H-8′), 2.48 (1H, dd, J = 13.4, 2.4 Hz, H-7′b), 2.32 (1H, m, H-8)；13C NMR (100 MHz, CD3OD) δ: 154.3 (C-3, 5), 147.5 (C-3′), 144.6 (C-4′), 141.4 (C-4), 135.4 (C-1), 133.6 (C-1′), 122.2 (C-6′), 116.4 (C-5′), 113.2 (C-2′), 105.1 (C-1′′), 104.5 (C-2, 6), 83.9 (C-7), 78.2 (C-5′′), 77.7 (C-3′′), 75.6 (C-2′′), 73.8 (C-9′), 71.2 (C-4′′), 62.6 (C-6′′), 60.8 (C-9), 57.1 (3, 5-OCH3), 56.2 (3′-OCH3), 54.2 (C-8), 43.8 (C-8′), 33.5 (C-7′)。以上数据与文献报道一致，故鉴定该化合物为肿柄雪莲苷。

化合物8：白色晶体，EI-MS：m/z 418 +，分子式为C22H26O8。1H NMR (400 MHz, CDCl3) δ: 6.60 (4H, s, H-2, 2′, 6, 6′), 4.72 (2H, d, J = 3.9 Hz, H-7, 7′), 4.29 (2H, dd, J = 8.9, 6.4 Hz, H-9a, 9a′), 3.88 (12H, s, 4×OCH3), 3.86～3.92 (2H, m, H-9b, 9b′), 3.10 (2H, m, H-8, 8′)；13C NMR (100 MHz, DMSO-d6) δ: 147.2 (C-3, 3′, 5, 5′), 134.5 (C-4, 4′), 132.3 (C-1, 1′), 102.6 (C-2, 2′, 6, 6′), 86.4 (C-7, 7′), 71.8 (C-9, 9′), 56.5 (4×OCH3), 54.6 (C-8, 8′)。以上数据与文献报道一致，故鉴定该化合物为丁香脂素。

化合物9：白色无定形粉末, EI-MS：m/z 348 +，分子式为C18H20O7。1H NMR (400 MHz, DMSO-d6) δ: 9.80 (1H, s, H-7′), 7.46 (1H, dd, J = 8.4, 2.0 Hz, H-6′), 7.35 (1H, d, J = 1.9 Hz, H-2′), 7.23 (1H, d, J = 8.5 Hz, H-5′), 7.01 (1H, d, J = 1.9 Hz, H-2), 6.80 (1H, dd, J = 8.1, 1.9 Hz, H-6), 6.67 (1H, d, J = 8.0 Hz, H-5), 4.71 (1H, d, J = 5.6 Hz, H-7), 4.65-4.51 (1H, m, H-8), 3.80 (3H, s, 3′-OCH3), 3.73 (3H, s, 3-COH3), 3.65 (1H, dd, J = 11.9, 5.9 Hz, H-9a), 3.51 (1H, dd, J = 11.9, 3.4 Hz, H-9b)；13C NMR (100 MHz, DMSO-d6)δ: 191.2 (C-7′), 154.1 (C-4′), 149.6 (C-4), 147.0 (C-3′), 145.5 (C-3), 132.8 (C-1), 129.2 (C-1′), 125.6 (C-6′), 119.2 (C-6), 114.5 (C-5′), 113.7 (C-5), 111.1 (C-2), 110.3 (C-2′), 83.5 (C-8), 71.4 (C-7), 60.3 (C-9), 56.1 (3′-OCH3), 55.9 (3-OCH3)。以上数据与文献报道一致，故鉴定该化合物为苏式-(7R,8R)-愈创木基丙三醇-8-香草醛醚。

化合物10：白色无定形粉末，EI-MS：m/z 522 +，分子式为C26H34O11。1H NMR (400 MHz, CD3OD) δ: 7.13 (1H, d, J = 8.4 Hz, H-5), 7.01 (1H, d, J = 1.7 Hz, H-2), 6.94 (1H, dd, J = 8.4, 1.7 Hz, H-6), 6.73 (1H, d, J = 1.7 Hz, H-6′), 6.71 (1H, d, J = 1.7 Hz, H-2′), 5.53 (1H, d, J = 5.8 Hz, H-7), 4.89 (1H, d, J = 7.3 Hz, Glc, H-1′′), 3.83 (3H, s, 3-OCH3), 3.82 (3H, s, 3′-OCH3), 3.75 (1H, m, H-9a), 3.66 (1H, m, H-9b), 3.54 (2H, t, J = 6.5 Hz, H-9′), 3.45 (1H, m, H-8), 2.62 (2H, t, J = 7.5 Hz, H-7′), 1.81 (2H, m, H-8′)；13C NMR (100 MHz, CD3OD) δ: 149.4 (C-3), 146.3 (C-4), 146.1 (C-4′), 143.7 (C-3′), 137.1 (C-1), 135.6 (C-1′), 128.3 (C-5′), 118.0 (C-6), 116.8 (C-5), 116.5 (C-6′), 112.7 (C-2′), 109.7 (C-2), 101.3 (C-1′′), 87.2 (C-7), 76.9 (C-5′′), 76.4 (C-3′′), 73.4 (C-2′′), 70.1 (C-4′′), 63.6 (C-9), 61.2 (C-6′′), 60.7 (C-9′), 55.5 (3-OCH3), 55.2 (3′-OCH3), 54.3 (C-8), 34.5 (C-8′), 31.5 (C-7′)。以上数据与文献报道一致，故鉴定该化合物为(7S,8R)-二氢去氢二松柏醇-4-O-β-D-吡喃糖葡萄苷。

化合物11：白色粉末，EI-MS：m/z 522 +，分子式为C26H34O11。1H NMR (400 MHz, DMSO-d6) δ: 7.01 (1H, d, J = 9.0 Hz, H-5′), 6.89 (1H, br s, H-2), 6.76 (1H, d, J = 1.9 Hz, H-6′), 6.75 (1H, s, H-6), 6.65 (1H, d, J = 8.1 Hz, H-5), 6.55 (1H, d, J = 2.0 Hz, H-2′), 4.85 (1H, d, J = 7.0 Hz, Glc, H-1′′), 4.73 (1H, d, J = 6.0 Hz, H-7′), 3.89 (1H, m, 6.0 Hz, H-9′), 3.73 (6H, s, 2×OCH3), 3.45 (2H, m, H-9), 2.21 (1H, m, H-8′), 3.66 (1H, m, H-8′), 3.59 (1H, t, J = 7.4 Hz, H-9′), 2.82 (1H, m, H-7′), 2.56 (1H, m, H-8), 2.40 (1H, m, H-7′), 2.20 (1H, m, H-8′)；13C NMR (100 MHz, DMSO-d6) δ: 148.6 (C-3′), 147.5 (C-3), 145.4 (C-4′), 144.5 (C-4), 137.1 (C-1′), 131.7 (C-1), 120.7 (C-6), 117.6 (C-6′), 115.4 (C-5), 115.4 (C-5′), 112.6 (C-2′), 112.6 (C-2), 100.2 (C-1′′), 81.6 (C-7′), 77.0 (C-5′′), 71.8 (C-2′′), 71.8 (C-9), 69.7 (C-4′′), 60.4 (C-6′′), 58.4 (C-9′), 56.2 (-OCH3), 55.3 (-OCH3), 52.6 (C-8′), 41.8 (C-8), 32.2 (C-7)。以上数据与文献报道一致，故鉴定该化合物为(-)-落叶松脂素- 4-O-β-D-吡喃葡萄糖苷。

化合物12：黄色针晶，EI-MS：m/z 594 +，分子式为C27H30O15。1H NMR (400 MHz, DMSO-d6) δ: 7.99 (2H, d, J = 8.0, H-2′, 6′), 6.86 (2H, d, J = 8.0 Hz, H-3′, 5′), 6.35 (1H, s, H-8), 6.16 (1H, s, H-6), 5.29 (1H, d, J = 8.0 Hz, Glc, H-1′′), 4.40 (1H, br s, Rha, H-1′′′), 1.00 (3H, d, J = 7.5 Hz, Rha, H-6′′′)；13C NMR (100 MHz, DMSO-d6) δ: 177.3 (C-4), 165.4 (C-7), 161.2 (C-5), 160.1 (C-4), 156.5 (C-2), 133.3 (C-3), 131.0 (C-2′, 6′), 120.8 (C-1), 115.2 (C-3′, 5′), 103.4 (C-10), 101.5 (C-1′′), 100.7 (C-1′′′), 99.0 (C-6), 93.8 (C-8), 76.3 (C-3′′), 75.9 (C-5′′), 74.1 (C-2′′), 71.9 (C-4′′′), 70.5 (C-4′′), 70.4 (C-2′′′), 69.8 (C-3′′′), 68.2 (C-5′′′), 67.0 (C-6′′), 17.7 (C-6′′′)。以上数据与文献报道一致，故鉴定该化合物为山柰酚-3-O-芸香糖苷。

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