正文 番石榴葉乙醇提取物的化學成分研究(2 / 3)

化合物6 無色針晶(甲醇);mp 79~81 ℃;ESI-MS m/z 243 [M+Na]+。1H-NMR(CDCl3,400 MHz)δ:5.27(1H,d,J=5.6 Hz,H-2),5.35(1H,d,J=5.6 Hz,H-3),1.47(1H,m,H-5),1.37(1H,m,H-6a),1.45(1H,m,H-6b),1.13(1H,m,H-7a),1.32(1H,m,H-7b),3.36(1H,br s,H-9),1.58(1H,m,H-10a),2.00(1H,m,H-10b),1.08(1H,m,H-11a),1.67(1H,dd,J=10.0,4.8 Hz,,H-11b),0.95(1H,m,H-12a),1.45(1H,m,H-12b),0.91(3H,s,H-13),1.01(3H,s,H-14),0.90(3H,s,H-15);13C-NMR(CDCl3,100 MHz)δ:49.5(C-1),136.0(C-2),138.5(C-3),47.4(C-4),49.2(C-5),20.7(C-6),33.8(C-7),35.1(C-8),74.0(C-9),27.9(C-10),33.8(C-11),35.1(C-12),24.4(C-13),33.0(C-14),27.9(C-15)。上述數據與文獻[7]報道一致,化合物6鑒定為clov-2-ene-9α-ol。

化合物7 無色油狀物;ESI-MS m/z 319 [M+Na]+。1H-NMR(CDCl3,400 MHz)δ:4.99(1H,dd,J=10.4,1.2 Hz,H-1a),5.14(1H,dd,J=17.2,1.2 Hz,H-1b),5.86(1H,dd,J=17.2,10.4 Hz,H-2),0.95~1.55(24H,m,H-4~15),0.75~0.85(15H,m,H-16~20);13C-NMR(CDCl3,100 MHz)δ:111.5(C-1),145.3(C-2),73.1(C-3),42.7(C-4),21.2(C-5),37.3(C-6),32.8(C-7),37.4(C-8),24.4(C-9),37.4(C-10),32.8(C-11),37.4(C-12),24.9(C-13),39.3(C-14),28.2(C-15),22.7(C-16),22.6(C-17),19.7(C-18),19.7(C-19),27.7(C-20)。上述數據與文獻[9]報道一致,化合物7鑒定為異植物醇。

化合物8 黃色粉末;mp 253~255 ℃,ESI-MS m/z 323 [M+Na]+。1H-NMR(DMSO-d6,400 MHz)δ:12.46(1H,s,5-OH),6.19(1H,d,J=2.4 Hz,H-6),6.47(1H,d,J=2.4 Hz,H-8),7.75(1H,d,J=2.4 Hz,H-2′),6.94(1H,d,J=11.2 Hz,H-5′),7.68(1H,dd,J=11.2,2.8 Hz,H-6′),3.84(3H,s,4′-OCH3);13C-NMR(DMSO-d6,100 MHz)δ:146.6(C-2),135.8(C-3),175.9(C-4),160.7(C-5),98.2(C-6),163.9(C-7),93.6(C-8),156.1(C-9),103.0(C-10),121.9(C-1′),115.5(C-2′),147.3(C-3′),148.8(C-4′),111.7(C-5′),121.7(C-6′),55.8(4′-OCH3)。上述數據與文獻[10]報道一致,化合物8鑒定為檉柳黃素。

化合物9 黃色粉末;mp >300 ℃,ESI-MS m/z 341 [M+Na]+。1H-NMR(DMSO-d6,400 MHz)δ:6.25(1H,s,H-6),7.84(1H,d,J=2.0 Hz,H-2′),7.74(1H,dd,J=8.4,2.0 Hz,H-6′),6.88(1H,d,J=8.4 Hz,H-5′);13C-NMR(DMSO-d6,100 MHz)δ:148.7(C-2),137.0(C-3),177.6(C-4),154.1(C-5),98.9(C-6),154.4(C-7),125.9(C-8),146.7(C-9),104.2(C-10),124.4(C-1′),116.2(C-2′),146.1(C-3′),148.1(C-4′),116.3(C-5′),122.0(C-6′)。上述數據與文獻[11]報道一致,化合物9鑒定為棉花素。

化合物10 黃色粉末;mp>300 ℃,ESI-MS m/z 325 [M+Na]+。1H-NMR(DMSO-d6,400 MHz)δ:12.49(1H,s,5-OH),6.18(1H,d,J=2.4 Hz,H-6),6.40(1H,d,J=2.4 Hz,H-8),7.67(1H,d,J=2.2 Hz,H-2′),7.53(1H,dd,J =8.4,2.2 Hz,H-6′),6.88(1H,d,J=8.4 Hz,H-5′);13C-NMR(DMSO-d6,100 MHz)δ:146.8(C-2),135.7(C-3),175.8(C-4),160.7(C-5),98.1(C-6),163.8(C-7),93.3(C-8),156.1(C-9),102.9(C-10),121.9(C-1′),115.5(C-2′),145.0(C-3′),147.6(C-4′),115.0(C-5′),119.9(C-6′)。上述數據與文獻[12]報道一致,化合物10鑒定為槲皮素。

化合物11 黃色粉末;mp >300 ℃,ESI-MS m/z 309 [M+Na]+。1H-NMR(DMSO-d6,400 MHz)δ:6.17(1H,d,J=2.0 Hz,H-6),6.39(1H,d,J=2.0 Hz,H-8),8.08(2H,d,J=8.8 Hz,H-2′,6′),6.90(2H,d,J=8.8 Hz,H-3′,5′);13C-NMR(DMSO-d6,100 MHz)δ:148.1(C-2),137.1(C-3),177.4(C-4),162.5(C-5),99.4(C-6),165.8(C-7),94.5(C-8),158.3(C-9),104.5(C-10),123.8(C-1′),116.3(C-2′,6′),130.7(C-3′,5′),160.6(C-4′)。上述數據與文獻[13]報道一致,化合物11鑒定為山柰酚。

化合物12 黃色粉末;245~246 ℃,ESI-MS m/z 457 [M+Na]+。1H-NMR(DMSO-d6,400 MHz)δ:6.20(1H,d,J=1.8 Hz,H-6),6.40(1H,d,J=1.8 Hz,H-8),7.51(1H,d,J = 2.0 Hz,H-2′),6.84(1H,d,J=8.4 Hz,H-5′),7.65(1H,dd,J=8.4,2.0 Hz,H-6′),5.27(1H,d,J=4.8 Hz,H-1″),3.18~3.76(4H,m,H-2″~5″);13C-NMR(DMSO-d6,100 MHz)δ:156.3(C-2),133.7(C-3),177.5(C-4),161.2(C-5),98.6(C-6),164.2(C-7),93.5(C-8),156.3(C-9),103.9(C-10),122.0(C-1′),115.7(C-2′),144.9(C-3′),148.6(C-4′),115.3(C-5′),120.9(C-6′),101.4(C-1″),70.6(C-2″),71.6(C-3″),66.0(C-4″),64.2(C-5″)。上述數據與文獻[14]報道一致,化合物12鑒定為guajaverin。

化合物13 黃色粉末;230~232 ℃,ESI-MS m/z 457 [M+Na]+。1H-NMR(DMSO-d6,400 MHz)δ:6.27(1H,d,J=2.0 Hz,H-6),6.41(1H,d,J=2.0 Hz,H-8),7.48(1H,d,J = 2.1 Hz,H-2′),7.55(1H,dd,J=8.4,2.1 Hz,H-6′),6.90(1H,d,J=8.4 Hz,H-5′),5.58(1H,br s,H-1″),3.58~4.10(4H,m,H-2″~5″);13C-NMR(DMSO-d6,100 MHz)δ:156.3(C-2),133.3(C-3),177.7(C-4),161.2(C-5),98.6(C-6),164.2(C-7),93.5(C-8),156.9(C-9),103.9(C-10),121.6(C-1′),115.5(C-2′),145.0(C-3′),148.4(C-4′),115.5(C-5′),120.9(C-6′),107.8(C-1″),82.0(C-2″),76.9(C-3″),85.8(C-4″),60.6(C-5″)。上述數據與文獻[14]報道一致,化合物13鑒定為avicularin。

化合物14 黃色粉末;mp 218~220 ℃,ESI-MS m/z 501 [M+Na]+。1H-NMR(DMSO-d6,400 MHz)δ:6.47(1H,s,H-3),6.68(1H,s,H-8),7.90(2H,m,H-2′,6′),7.54(2H,m,H-3′,5′),7.52(1H,m,H-4′),4.90(1H,d,J=9.6 Hz,H-1″),3.30~4.17(5H,m,H-2″~6″);13C-NMR(DMSO-d6,100 MHz)δ:165.6(C-2),106.1(C-3),184.1(C-4),162.1(C-5),109.5(C-6),165.6(C-7),95.5(C-8),159.0(C-9),105.3(C-10),132.4(C-1′),127.4(C-2′,C-6′),130.4(C-3′,C-5′),133.1(C-4′),75.4(C-1″),72.7(C-2″),80.1(C-3″),71.7(C-4″),82.7(C-5″),62.8(C-6″)。上述數據與文獻[15]報道一致,化合物14鑒定為chrysin 6-C-glucoside。

化合物15 白色粉末;mp >300 ℃,ESI-MS m/z 513 [M+Na]+。1H-NMR(DMSO-d6,400 MHz)δ:6.35(2H,s,H-3a),7.41(1H,t,J=2.0 Hz,H-5),7.80(1H,s,H-5′),3.38(3H,s,3′-OCH3),5.06(1H,d,J=4.8 Hz,H-1″),3.17~3.75(5H,m,H-2″~6″);13C-NMR(DMSO-d6,100 MHz)δ:113.4(C-1),131.3(C-2),138.3(C-3),150.6(C-4),104.6(C-5),111.6(C-6),158.0(C-7),115.2(C-1′),141.2(C-2′),141.9(C-3′),152.1(C-4′),112.6(C-5′),112.3(C-6′),157.3(C-7′),101.5(C-1″),73.4(C-2″),76.6(C-3″),69.6(C-4″),77.4(C-5″),60.7(C-6″),61.7(3′-OCH3),104.0(C-3a)。上述光譜數據與文獻[16]報道一致,化合物15鑒定為3′-O-methyl-3,4-methylenedioxyellagic acid 4′-O-β-D-glucopyranoside。

化合物16 無色針晶(甲醇);mp 207~209 ℃,ESI-MS m/z 161 [M+Na]+。1H-NMR(CD3OD,400 MHz)δ:7.87(2H,d,J=8.4 Hz,H-2,6),6.81(2H,d,J=8.4 Hz,H-3,5);13C-NMR(CD3OD,100 MHz)δ:122.6(C-1),133.0(C-2,6),116.0(C-3,5),163.3(C-4),170.1(C-7)。上述數據與文獻[17]報道一致,化合物16鑒定為對羥基苯甲酸。