1、硕士研究生课程硕士研究生课程高等波谱解析高等波谱解析天然药物及仿生药物国家重点实验室天然药物及仿生药物国家重点实验室 博士研究生导师博士研究生导师 杨杨 秀秀 伟伟1H NMR 谱（一维）CH,CH2,CH3中质子信号的归属1H 化学位移相关二维 NMR 谱 （自旋体系的解析）13C NMR 谱（一维）INEPT 谱（识别碳原子基团）1H-13C 化学位移相关二维 NMR 谱确定碳原子骨架NOE 相关二维 NMR 谱 NOE 差谱（确定 1H 的空间排布）确定分子结构（1H 原子的归属）13C 原子的归属天然化合物结构解析的一般程序天然化合物结构解析的一般程序 H=H0-2HH=H0+2HH=
2、H0+3HH=H0+HH=H0-HH=H0-3HH=H0+H-H=H0H=H0-H+H=H0H0H0CHHHCHHCl(Triplet)(Quarterlet)CHHClCHHH1:2:11:3:3:1可可能能存存在在自自旋旋方方向向 预预期期图图谱谱 峰峰强强度度比比 7.85(1H,d,J=9.5Hz,H-4)6.18(1H,d,J=9.5Hz,H-3)7.45(1H,d,J=8.3Hz,H-5)7.85(1H,d,J=9.5Hz,H-4)7.45(1H,d,J=8.3Hz,H-5)6.18(1H,d,J=9.5Hz,H-3)6.79(1H,dd,J=2.2,8.3Hz,H-6)6.71(
3、1H,d,J=2.2Hz,H-8)The 1H NMR Spectrum of UmbelliferoneOOHO123456784a8a728a45634a8The 13C NMR Spectrum of Umbelliferone155.4111.3102.1161.2113.0129.6144.4111.3160.31OOHO7.921HdJ=9.5HzH-4 7.471HsH-5 6.781HsH-8 6.211HdJ=9.5HzH-3 4.711HtJ=8.8HzH-23.192HdJ=8.8HzH-31.163HsH-51.143HsH-68a4a87654321OOOHO2345
4、6The 1H NMR Spectrum of NodakenetinThe 13C NMR Spectrum of Nodakenetin728a4654a3824356OOOHO160.4111.1144.5112.0155.0123.8125.4163.296.728.790.969.924.825.87.941HdJ=9.5HzH-46.231HdJ=9.5HzH-37.491HsH-56.231HsH-84.911HtJ=8.8HzH-24.891HdJ=7.3HzH-14.401HdJ=7.3HzH-17.941HdJ=9.5HzH-4 7.491HsH-5 6.811HsH-8
5、6.231HdJ=9.5HzH-3 4.911HtJ=8.8HzH-24.891HdJ=7.3HzH-14.401HdJ=8.0HzH-6b3.681HddJ=8.0,12.5HzH-6a3.282HdJ=8.8HzH-31.323HsH-51.193HsH-6The 1H NMR Spectrum of Nodakenin65432123456784a8aOOHHOHOOHOOOO234561524372 8a46534a816423543562The 13C NMR Spectrum of Nodakenin97.261.276.970.376.673.5OOHHOHOOHOOOO155.
6、0111.296.8123.8125.4144.6112.2160.489.729.177.023.220.6163.0The 1H NMR Spectrum of Forbesoside4.972HtJ=8.8HzH-34.621HdJ=7.8HzG-14.491HddJ=11.6HzG-6b4.351HddJ=11.6HzG-6aOH3.80OMe3.611HdddJ=2.3,8.0,9.0HzG-5G-3G-4G-227.601HdJ=9.3HzH-47.461HdJ=16.1HzH-87.171HsH-56.891HdJ=2.0HzH-26.791HddJ=2.0,8.1HzH-66.
7、681HdJ=8.1HzH-56.521HsH-86.171HdJ=16.1HzH-76.091HdJ=9.3HzH-31654328a4a8765432123456OOOOOHHOHOOOOHOOMe789The 1H NMR Spectrum of Tetraacetyl6-O-(trans-Feruloyl)Nodakenin1654328a4a8765432109111213OOOOOAcAcOAcOOCH2OMeAcOOO789612345The 1H NMR Spectrum of Tetraacetyl6-O-(trans-Feruloyl)nodakenin7.601HdJ=1
8、6.0HzH-77.521HdJ=9.5HzH-4 7.121HsH-5 7.03(2H,d,J=3.2Hz,H-5,6)7.02(1H,s,2)6.651HsH-8 6.311HdJ=16.0HzH-86.161HdJ=9.5HzH-3 5.241HtJ=9.4HzH-35.061HtJ=9.4HzH-44.941HddJ=9.4HzH-24.801HtJ=8.8HzH-10 4.831HdJ=8.1HzH-14.351HddJ=2.7,12.0HzH-6b 4.281HddJ=6.1,12.0HzH-6a 3.821HdddJ=2.9,6.1,9.4HzH-53.853HsOMe 3.17
9、2HdJ=8.8HzH-9 2.333HsAr-OAc(-Me)2.053HsGlc-OAc(-Me)1.993HsGlc-OAc(-Me)1.863HsGlc-OAc(-Me)1.353Hs131.263Hs121654328a4a8765432109111213OOOOOAcAcOAcOOCH2OMeAcOOO789612345The 1H NMR Spectrum of Tetraacetyl6-O-(trans-Feruloyl)nodakeninThe 13C NMR Spectrum of Tetraacetyl6-O-(trans-Feruloyl)nodakeninCOOCH3
10、COOCH39728a347465156824a381101135246OMe91312OMeOOHHHH161.3112.9143.7112.9152.8126.2107.3160.2117.96.19(d)7.58(d)7.27(d)6.81(d)7.55(dd)7.24(d)6.10(s)OHHHHRHO7.33(dd)8.18(d)香豆素类化合物的香豆素类化合物的NMR特征特征OO+-C3、C6、C8-H在较高场C4、C5、C7-H在较低场核磁共振波谱规律核磁共振波谱规律1H-NMR受内酯羰基吸电子共轭效应的影响受内酯羰基吸电子共轭效应的影响OOHH43H-3,d,6.16.4 J=9.5HzH-4,d,7.58.3 J=9.5HzOOHRO37C-7有氧取代，有氧取代，C-3-0.17ppmOORH45C-5有基团取代，有基团取代，H-4 -0.3 ppm，在，在7.9-8.2之间之间OOOHH2323OOOHH呋喃香豆素如果呋喃呋喃香豆素如果呋喃环上没有取代环上没有取代 H-2,H-2 7.34-7.80 线型线型H-36.7，角型，角型H-37.0OO23456788a4a160.4116.4143.6118.8128.1124.4131.8116.4有有OR取代取代 直接相连的碳直接相连的碳+30ppm邻碳邻碳 13ppm对碳对碳 8ppm13C-NMR
