2017Magnetic Resonance in ChemistryRequires access

Structure elucidation, total assignment of the 1H and 13C chemical shifts, and absolute configuration by NMR techniques of dammarane‐type triterpenes from Hippocratea volubilis

María L. Kennedy, Atteneri López‐Arencibia, María Reyes-Batllé, Jacob Lorenzo‐Morales, José E. Piñero, Isabel L. Bazzocchi, Ignacio A. Jiménez

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Abstract

Figure S1.1 1H NMR spectrum of compound 1 (600 MHz, CDCl3) S1.2. Expanded 1H NMR spectrum of compound 1 S2. 13C NMR spectrum of compound 1 (150 MHz, CDCl3) S3. COSY spectrum of compound 1 S4. HSQC spectrum of compound 1 S5. HMBC spectrum of compound 1 S6. ROESY spectrum of compound 1 S7.1. 1H NMR spectrum of compound 2 (600 MHz, CDCl3) S7.2. Expanded 1H NMR spectrum of compound 2 S8. 13C NMR spectrum of compound 2 (150 MHz, CDCl3) S9. COSY spectrum of compound 2 S10. HSQC spectrum of compound 2 S11. HMBC spectrum of compound 2 S12.1. 1D GOESY spectrum of compound 2 (600 MHz). Irradiation of H-5 S12.2. 1D GOESY spectrum of compound 2 (600 MHz). Irradiation of H-18 S12.3. 1D GOESY spectrum of compound 2 (600 MHz). Irradiation of H-30 S13.1. 1H NMR spectrum of compound 1a (600 MHz, CDCl3) S13.2. Expanded 1H NMR spectrum of compound 1a S14. 13C NMR spectrum of compound 1a (150 MHz, CDCl3) S15.1. 1H NMR spectrum of compound 1b (600 MHz, CDCl3) S15.2. Expanded 1H NMR spectrum of compound 1b S16. 13C NMR spectrum of compound 1b (150 MHz, CDCl3) S17.1. 1H NMR spectrum of compound 1c (600 MHz, CD3CN) S17.2. Expanded1H NMR spectrum of compound 1c S18. 13C NMR spectrum of compound 1c (150 MHz, CD3CN) S19. COSY spectrum of compound 1c S20. HMBC spectrum of compound 1c S21.1. 1H NMR spectrum of compound 1c (600 MHz, saturated with barium salt) S21.2. Expanded 1H NMR spectrum of compound 1c (saturated with barium salt) S22. 13C NMR spectrum of compound 1c (150 MHz, saturated with barium salt) S23. COSY spectrum of compound 1c, saturated with barium salt S24.1. HMBC spectrum of compound 1c, saturated with barium salt S24.2. Expanded HMBC spectrum of compound 1c, saturated with barium salt S25.1. 1H NMR spectrum of compound 2a (600 MHz, CD3CN) S25.2. Expanded 1H NMR spectrum of compound 2a S26. 13C NMR spectrum of compound 2a (150 MHz, CD3CN) S27. COSY spectrum of compound 2a S28. HMBC spectrum of compound 2a S29.1. 1H NMR spectrum of compound 2a (600 MHz, saturated with barium salt) S29.2. Expanded 1H NMR spectrum of compound 2a (saturated with barium salt) S30. 13C NMR spectrum of compound 2a (150 MHz, saturated with barium salt) S31. COSY spectrum of compound 2a, saturated with barium salt S32. HMBC spectrum of compound 2a, saturated with barium salt Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

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Figure S1.1 1H NMR spectrum of compound 1 (600 MHz, CDCl3) S1.2. Expanded 1H NMR spectrum of compound 1 S2. 13C NMR spectrum of compound 1 (150 MHz, CDCl3) S3. COSY spectrum of compound 1 S4. HSQC spectrum of compound 1 S5. HMBC spectrum of compound 1 S6. ROESY spectrum of compound 1 S7.1. 1H NMR spectrum of compound 2 (600 MHz, CDCl3) S7.2. Expanded 1H NMR spectrum of compound 2 S8. 13C NMR spectrum of compound 2 (150 MHz, CDCl3) S9. COSY spectrum of compound 2 S10. HSQC spectrum of compound 2 S11. HMBC spectrum of compound 2 S12.1. 1D GOESY spectrum of compound 2 (600 MHz). Irradiation of H-5 S12.2. 1D GOESY spectrum of compound 2 (600 MHz). Irradiation of H-18 S12.3. 1D GOESY spectrum of compound 2 (600 MHz). Irradiation of H-30 S13.1. 1H NMR spectrum of compound 1a (600 MHz, CDCl3) S13.2. Expanded 1H NMR spectrum of compound 1a S14. 13C NMR spectrum of compound 1a (150 MHz, CDCl3) S15.1. 1H NMR spectrum of compound 1b (600 MHz, CDCl3) S15.2. Expanded 1H NMR spectrum of compound 1b S16. 13C NMR spectrum of compound 1b (150 MHz, CDCl3) S17.1. 1H NMR spectrum of compound 1c (600 MHz, CD3CN) S17.2. Expanded1H NMR spectrum of compound 1c S18. 13C NMR spectrum of compound 1c (150 MHz, CD3CN) S19. COSY spectrum of compound 1c S20. HMBC spectrum of compound 1c S21.1. 1H NMR spectrum of compound 1c (600 MHz, saturated with barium salt) S21.2. Expanded 1H NMR spectrum of compound 1c (saturated with barium salt) S22. 13C NMR spectrum of compound 1c (150 MHz, saturated with barium salt) S23. COSY spectrum of compound 1c, saturated with barium salt S24.1. HMBC spectrum of compound 1c, saturated with barium salt S24.2. Expanded HMBC spectrum of compound 1c, saturated with barium salt S25.1. 1H NMR spectrum of compound 2a (600 MHz, CD3CN) S25.2. Expanded 1H NMR spectrum of compound 2a S26. 13C NMR spectrum of compound 2a (150 MHz, CD3CN) S27. COSY spectrum of compound 2a S28. HMBC spectrum of compound 2a S29.1. 1H NMR spectrum of compound 2a (600 MHz, saturated with barium salt) S29.2. Expanded 1H NMR spectrum of compound 2a (saturated with barium salt) S30. 13C NMR spectrum of compound 2a (150 MHz, saturated with barium salt) S31. COSY spectrum of compound 2a, saturated with barium salt S32. HMBC spectrum of compound 2a, saturated with barium salt Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

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Available abstract

Figure S1.1 1H NMR spectrum of compound 1 (600 MHz, CDCl3) S1.2. Expanded 1H NMR spectrum of compound 1 S2. 13C NMR spectrum of compound 1 (150 MHz, CDCl3) S3. COSY spectrum of compound 1 S4. HSQC spectrum of compound 1 S5. HMBC spectrum of compound 1 S6. ROESY spectrum of compound 1 S7.1. 1H NMR spectrum of compound 2 (600 MHz, CDCl3) S7.2. Expanded 1H NMR spectrum of compound 2 S8. 13C NMR spectrum of compound 2 (150 MHz, CDCl3) S9. COSY spectrum of compound 2 S10. HSQC spectrum of compound 2 S11. HMBC spectrum of compound 2 S12.1. 1D GOESY spectrum of compound 2 (600 MHz). Irradiation of H-5 S12.2. 1D GOESY spectrum of compound 2 (600 MHz). Irradiation of H-18 S12.3. 1D GOESY spectrum of compound 2 (600 MHz). Irradiation of H-30 S13.1. 1H NMR spectrum of compound 1a (600 MHz, CDCl3) S13.2. Expanded 1H NMR spectrum of compound 1a S14. 13C NMR spectrum of compound 1a (150 MHz, CDCl3) S15.1. 1H NMR spectrum of compound 1b (600 MHz, CDCl3) S15.2. Expanded 1H NMR spectrum of compound 1b S16. 13C NMR spectrum of compound 1b (150 MHz, CDCl3) S17.1. 1H NMR spectrum of compound 1c (600 MHz, CD3CN) S17.2. Expanded1H NMR spectrum of compound 1c S18. 13C NMR spectrum of compound 1c (150 MHz, CD3CN) S19. COSY spectrum of compound 1c S20. HMBC spectrum of compound 1c S21.1. 1H NMR spectrum of compound 1c (600 MHz, saturated with barium salt) S21.2. Expanded 1H NMR spectrum of compound 1c (saturated with barium salt) S22. 13C NMR spectrum of compound 1c (150 MHz, saturated with barium salt) S23. COSY spectrum of compound 1c, saturated with barium salt S24.1. HMBC spectrum of compound 1c, saturated with barium salt S24.2. Expanded HMBC spectrum of compound 1c, saturated with barium salt S25.1. 1H NMR spectrum of compound 2a (600 MHz, CD3CN) S25.2. Expanded 1H NMR spectrum of compound 2a S26. 13C NMR spectrum of compound 2a (150 MHz, CD3CN) S27. COSY spectrum of compound 2a S28. HMBC spectrum of compound 2a S29.1. 1H NMR spectrum of compound 2a (600 MHz, saturated with barium salt) S29.2. Expanded 1H NMR spectrum of compound 2a (saturated with barium salt) S30. 13C NMR spectrum of compound 2a (150 MHz, saturated with barium salt) S31. COSY spectrum of compound 2a, saturated with barium salt S32. HMBC spectrum of compound 2a, saturated with barium salt Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Key concepts: Chemistry, Proton NMR, Carbon-13 NMR, Carbon-13 NMR satellite, Heteronuclear single quantum coherence spectroscopy, Chemical shift, Stereochemistry, NMR spectra database

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Structure elucidation, total assignment of the 1H and 13C chemical shifts, and absolute configuration by NMR techniques of dammarane‐type triterpenes from Hippocratea volubilis — Research Paper | ScholarLens