A New Apiofuranoside from the Rattan of Piper flaviflorum
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1 Supporting Information Rec. Nat. Prod. 8:1 (2014) 1-6 A New Apiofuranoside from the Rattan of Piper flaviflorum Qianliang Ming 1,a, Yu Wu 1,a, Chengjian Zheng 1*, Xuehong Deng 1,2, Jianyong Zhu 1 and Luping Qin 1,3* 1 Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, Shanghai , P. R. China 2 Department of Pharmacy, Fujian University of Traditional Chinese Medicine, 1 Huatuo Road, Fuzhou , P. R. China 3 Shanghai Key Laboratory for Pharmaceutical Metabolite Research, Shanghai , P. R. China Table of Contents Page S1: HR-ESI-MS Spectrum of Compound 1 (flavifloside A) 3 S2: 1 H-NMR (600 MHz, CD 3 D) Spectrum of Compound 1 (flavifloside A) 4 S3: 13 C-NMR (150 MHz, CD 3 D) Spectrum of Compound 1 (flavifloside A) 5 S4: DEPT (150 MHz, CD 3 D) Spectrum of Compound 1 (flavifloside A) 6 S5: H-HCSY (600 MHz) Spectrum of Compound 1 (flavifloside A) 7 S6: HSQC (600 MHz) Spectrum of Compound 1 (flavifloside A) 8 S7: HMBC (600 MHz) Spectrum of Compound 1 (flavifloside A) 9 S8: NESY (600 MHz) Spectrum of Compound 1 (flavifloside A) 10 S9: 1 H-NMR (600 MHz, CD 3 D) Spectrum of Compound 2 (seguinoside E) 11 S10: Expansion of the 1 H-NMR Spectrum of Compound 2 (seguinoside E) 12 S11: Expansion of the 1 H-NMR Spectrum of Compound 2 (seguinoside E) 13 S12: 13 C-NMR (150 MHz, CD 3 D) Spectrum of Compound 2 (seguinoside E) 14 S13: DEPT (150 MHz, CD 3 D) Spectrum of Compound 2 (seguinoside E) 15 S14: 1 H-NMR (600 MHz, CD 3 D) Spectrum of Compound 3 (seguinoside K) 16 S15: Expansion of the 1 H-NMR Spectrum of Compound 3 (seguinoside K) 17 S16: Expansion of the 1 H-NMR Spectrum of Compound 3 (seguinoside K) 18 1
2 S17: 13 C-NMR (150 MHz, CD 3 D) Spectrum of Compound 3 (seguinoside K) 19 S18: DEPT (150 MHz, CD 3 D) Spectrum of Compound 3 (seguinoside K) 20 S19: HR-ESI-MS Spectrum of Compound 4 (6'--(3,4-dimethoxycinnamoyl)-arbutin) 21 S20: 1 H-NMR (600 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4- dimethoxycinnamoyl)-arbutin) 22 S21: Expansion of the 1 H-NMR Spectrum of Compound 4 (6'--(3,4-dimethoxycinnamoyl)- arbutin) 23 S22: Expansion of the 1 H-NMR Spectrum of Compound 4 (6'--(3,4-dimethoxycinnamoyl)- arbutin) 24 S23: 13 C-NMR (150 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4- dimethoxycinnamoyl)-arbutin) 25 S24: DEPT (150 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4-dimethoxycinnamoyl)- arbutin) 26 S25: H-HCSY (600 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4- dimethoxycinnamoyl)-arbutin) 27 S26: HSQC (600 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4-dimethoxycinnamoyl)- arbutin) 28 S27: HMBC (600 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4- dimethoxycinnamoyl)-arbutin) 29 S28: NESY (600 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4- dimethoxycinnamoyl)-arbutin) 30 2
3 S1: HR-ESI-MS Spectrum of Compound 1 (flavifloside A) 3
4 H ' H 4' 1' 3' H 2' H S2: 1 H-NMR (600 MHz, CD 3 D) Spectrum of Compound 1 (flavifloside A) 4
5 H ' H 4' 1' 3' H 2' H S3: 13 C-NMR (150 MHz, CD 3 D) Spectrum of Compound 1 (flavifloside A) 5
6 S4: DEPT (150 MHz, CD 3 D) Spectrum of Compound 1 (flavifloside A) 6
7 H ' H 4' 1' 3' H 2' H S5: H-HCSY (600 MHz) Spectrum of Compound 1 (flavifloside A) 7
8 H ' H 4' 1' 3' H 2' H S6: HSQC (600 MHz) Spectrum of Compound 1 (flavifloside A) 8
9 H ' H 4' 1' 3' H 2' H S7: HMBC (600 MHz) Spectrum of Compound 1 (flavifloside A) 9
10 H ' H 4' 1' 3' H 2' H S8: NESY (600 MHz) Spectrum of Compound 1 (flavifloside A) 10
11 5''' H 4''' 6''' 1''' 6' 2 3 3''' 5" 1" 1 4 2''' 4" 5' 4' H 3" 2" 1' 6 5 H H H 3' 2' H H S9: 1 H-NMR (600 MHz, CD 3 D) Spectrum of Compound 2 (seguinoside E) 11
12 S10: Expansion of the 1 H-NMR Spectrum of Compound 2 (seguinoside E) 12
13 S11: Expansion of the 1 H-NMR Spectrum of Compound 2 (seguinoside E) 13
14 5''' H 4''' 6''' 1''' 6' 2 3 3''' 5" 1" 1 4 2''' 4" 5' 4' H 3" 2" 1' 6 5 H H H 3' 2' H H S12: 13 C-NMR (150 MHz, CD 3 D) Spectrum of Compound 2 (seguinoside E) 14
15 5''' H 4''' 6''' 1''' 6' 2 3 3''' 5" 1" 1 4 2''' 4" 5' 4' H 3" 2" 1' 6 5 H H H 3' 2' H H S13: DEPT (150 MHz, CD 3 D) Spectrum of Compound 2 (seguinoside E) 15
16 5''' H 4''' 6''' 1''' 6' 2 3 3''' 5" 1" 1 4 2''' 4" 5' 4' H 3" 2" 1' 6 5 H H H 3' 2' H H S14: 1 H-NMR (600 MHz, CD 3 D) Spectrum of Compound 3 (seguinoside K) 16
17 S15: Expansion of the 1 H-NMR Spectrum of Compound 3 (seguinoside K) 17
18 S16: Expansion of the 1 H-NMR Spectrum of Compound 3 (seguinoside K) 18
19 5''' H 4''' 6''' 1''' 6' 2 3 3''' 5" 1" 1 4 2''' 4" 5' 4' H 3" 2" 1' 6 5 H H H 3' 2' H H S17: 13 C-NMR (150 MHz, CD 3 D) Spectrum of Compound 3 (seguinoside K) 19
20 5''' H 4''' 6''' 1''' 6' 2 3 3''' 5" 1" 1 4 2''' 4" 5' 4' H 3" 2" 1' 6 5 H H H 3' 2' H H S18: DEPT (150 MHz, CD 3 D) Spectrum of Compound 3 (seguinoside K) 20
21 S19: HR-ESI-MS Spectrum of Compound 4 (6'--(3,4-dimethoxycinnamoyl)-arbutin) 21
22 β α 6' 5' 4' H H 3' 2" 3" 1" 4" H 1' 6" 5" 2' H S20: 1 H-NMR (600 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4- dimethoxycinnamoyl)-arbutin) 22
23 S21: Expansion of the 1 H-NMR Spectrum of Compound 4 (6'--(3,4-dimethoxycinnamoyl)- arbutin) 23
24 S22: Expansion of the 1 H-NMR Spectrum of Compound 4 (6'--(3,4-dimethoxycinnamoyl)- arbutin) 24
25 β α 6' 5' 4' H H 3' 2" 3" 1" 4" H 1' 6" 5" 2' H S23: 13 C-NMR (150 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4- dimethoxycinnamoyl)-arbutin) 25
26 β α 6' 5' 4' H H 3' 2" 3" 1" 4" H 1' 6" 5" 2' H S24: DEPT (150 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4-dimethoxycinnamoyl)- arbutin) 26
27 β α 6' 5' 4' H H 3' 2" 3" 1" 4" H 1' 6" 5" 2' H S25: H-HCSY (600 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4- dimethoxycinnamoyl)-arbutin) 27
28 β α 6' 5' 4' H H 3' 2" 3" 1" 4" H 1' 6" 5" 2' H S26: HSQC (600 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4-dimethoxycinnamoyl)- arbutin) 28
29 β α 6' 5' 4' H H 3' 2" 3" 1" 4" H 1' 6" 5" 2' H S27: HMBC (600 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4- dimethoxycinnamoyl)-arbutin) 29
30 2 β 3 1 α 6' 5' ' H H 3' 2' H 2" 3" 1" 4" H 1' 6" 5" S28: NESY (600 MHz, CD 3 D) Spectrum of Compound 4 (6'--(3,4- dimethoxycinnamoyl)-arbutin) 30
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