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1 Supporting Information Bioactive Flavaglines and Other Constituents Isolated from Aglaia perviridis # Li Pan, Ulyana Muñoz Acuña, Jie Li, Nivedita Jena, Tran Ngoc Ninh, Caroline M. Pannell, Heebyung Chai, James R. Fuchs, Esperanza J. Carcache de Blanco,, Djaja D. Soejarto,, and A. Douglas Kinghorn *, Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210, United States Division of Pharmacy Practice and Administration, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210, United States Institute of Ecology and Biological Resources, Vietnamese Academy of Science and Technology, Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam Department of Plant Sciences, University of Oxford, South Parks Road, Oxford OX1 3RB, U. K. Program for Collaborative Research in the Pharmaceutical Science and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, United States Department of Botany, Field Museum of Natural History, 1400 S. Lake Shore Drive, Chicago, Illinois 60605, United States # Dedicated for Dr. Lester A. Mitscher, of the University of Kansas, for his pioneering
2 work on the discovery of bioactive natural products and their derivatives Supporting information list. Figure S H NMR spectrum of compound 1 (CDCl 3, 400 MHz). Figure S C DEPT 135 spectrum of compound 1 (CDCl 3, 100 MHz). Figure S C NMR spectrum of compound 1 (CDCl 3, 100 MHz). Figure S1-4. HSQC spectrum of compound 1 (CDCl 3, 400 MHz). Figure S1-5. HMBC spectrum of compound 1 (CDCl 3, 400 MHz). Figure S H- 1 H COSY spectrum of compound 1 (CDCl 3, 400 MHz). Figure S1-7. NOESY spectrum of compound 1 (CDCl 3, 400 MHz). Figure S H NMR spectrum of compound 2 (CDCl 3, 400 MHz). Figure S C DEPT 135 spectrum of compound 2 (CDCl 3, 100 MHz). Figure S C NMR spectrum of compound 2 (CDCl 3, 100 MHz). Figure S2-4. HSQC spectrum of compound 2 (CDCl 3, 400 MHz). Figure S2-5. HMBC spectrum of compound 2 (CDCl 3, 400 MHz). Figure S H- 1 H COSY spectrum of compound 2 (CDCl 3, 400 MHz). Figure S2-7. NOESY spectrum of compound 2 (CDCl 3, 400 MHz). Figure S H NMR spectrum of compound 3 (CDCl 3, 400 MHz). Figure S C DEPT 135 spectrum of compound 3 (CDCl 3, 100 MHz). Figure S C NMR spectrum of compound 3 (CDCl 3, 100 MHz). Figure S3-4. HSQC spectrum of compound 3 (CDCl 3, 400 MHz). Figure S3-5. HMBC spectrum of compound 3 (CDCl 3, 400 MHz). Figure S H- 1 H COSY spectrum of compound 3 (CDCl 3, 400 MHz). Figure S3-7. NOESY spectrum of compound 3 (CDCl 3, 400 MHz). Figure S H NMR spectrum of compound 4 (CDCl 3, 400 MHz). Figure S C DEPT 135 spectrum of compound 4 (CDCl 3, 100 MHz). Figure S C NMR spectrum of compound 4 (CDCl 3, 100 MHz). Figure S4-4. HSQC spectrum of compound 4 (CDCl 3, 400 MHz). Figure S4-5. HMBC spectrum of compound 4 (CDCl 3, 400 MHz). Figure S H- 1 H COSY spectrum of compound 4 (CDCl 3, 400 MHz). Figure S4-7. NOESY spectrum of compound 4 (CDCl 3, 400 MHz). Figure S H NMR spectrum of compound 5 (CDCl 3, 400 MHz). Figure S C DEPT 135 spectrum of compound 5 (CDCl 3, 100 MHz). Figure S C NMR spectrum of compound 5 (CDCl 3, 100 MHz). Figure S5-4. HSQC spectrum of compound 5 (CDCl 3, 400 MHz). Figure S5-5. HMBC spectrum of compound 5 (CDCl 3, 400 MHz). Figure S5-6. NOESY spectrum of compound 5 (CDCl 3, 400 MHz). Figure S H NMR spectrum of (R)-MTPA ester of compound 5 (pyridine-d 5, 400 MHz). Figure S H NMR spectrum of (S)-MTPA ester of compound 5 (pyridine-d 5, 400
3 MHz). Figure S H NMR spectrum of compound 6 (CDCl 3, 400 MHz). Figure S C DEPT 135 spectrum of compound 6 (CDCl 3, 100 MHz). Figure S C NMR spectrum of compound 6 (CDCl 3, 100 MHz). Figure S6-4. HSQC spectrum of compound 6 (CDCl 3, 400 MHz). Figure S6-5. HMBC spectrum of compound 6 (CDCl 3, 400 MHz). Figure S H- 1 H COSY spectrum of compound 6 (CDCl 3, 400 MHz). Figure S6-7. NOESY spectrum of compound 6 (CDCl 3, 400 MHz). Figure S H NMR spectrum of (R)-MTPA ester of compound 6 (pyridine-d 5, 400 MHz). Figure S H NMR spectrum of (S)-MTPA ester of compound 6 (pyridine-d 5, 400 MHz). Figure S H NMR spectrum of compound 7 (CDCl 3, 400 MHz). Figure S C DEPT 135 spectrum of compound 7 (CDCl 3, 100 MHz). Figure S C NMR spectrum of compound 7 (CDCl 3, 100 MHz). Figure S7-4. HSQC spectrum of compound 7 (CDCl 3, 400 MHz). Figure S7-5. HMBC spectrum of compound 7 (CDCl 3, 400 MHz). Figure S H- 1 H COSY spectrum of compound 7 (CDCl 3, 400 MHz). Figure S7-7. NOESY spectrum of compound 7 (CDCl 3, 400 MHz). Figure S H NMR spectrum of (R)-MTPA ester of compound 7 (pyridine-d 5, 400 MHz). Figure S H NMR spectrum of (S)-MTPA ester of compound 7 (pyridine-d 5, 400 MHz). Figure S H NMR spectrum of compound 8 (methanol-d 4, 400 MHz). Figure S C DEPT 135 spectrum of compound 8 (methanol-d 4, 100 MHz). Figure S C NMR spectrum of compound 8 (methanol-d 4, 100 MHz). Figure S8-4. HSQC spectrum of compound 8 (methanol-d 4, 400 MHz). Figure S8-5. HMBC spectrum of compound 8 (methanol-d 4, 400 MHz). Figure S H- 1 H COSY spectrum of compound 8 (methanol-d 4, 400 MHz). Figure S8-7. NOESY spectrum of compound 8 (methanol-d 4, 400 MHz).
4 Figure S H NMR spectrum of compound 1 (CDCl 3, 400 MHz). Figure S C DEPT135 spectrum of compound 1 (CDCl 3, 100 MHz).
5 Figure S C NMR spectrum of compound 1 (CDCl 3, 100 MHz). Figure S1-4. HSQC spectrum of compound 1 (CDCl 3, 400, 100 MHz).
6 Figure S1-5. HMBC spectrum of compound 1 (CDCl 3, 400, 100 MHz). Figure S H- 1 H COSY spectrum of compound 1 (CDCl 3, 400 MHz).
7 Figure S1-7. NOESY spectrum of compound 1 (CDCl 3, 400 MHz). Figure S H NMR spectrum of compound 2 (CDCl 3, 400 MHz).
8 Figure S C DEPT135 spectrum of compound 2 (CDCl 3, 100 MHz). Figure S C NMR spectrum of compound 2 (CDCl 3, 100 MHz).
9 Figure S2-4. HSQC spectrum of compound 2 (CDCl 3, 400, 100 MHz). Figure S2-5. HMBC spectrum of compound 2 (CDCl 3, 400, 100 MHz).
10 Figure S H- 1 H COSY spectrum of compound 2 (CDCl 3, 400 MHz). Figure S2-7. NOESY spectrum of compound 2 (CDCl 3, 400 MHz).
11 Figure S H NMR spectrum of compound 3 (CDCl 3, 400 MHz). Figure S C DEPT135 spectrum of compound 3 (CDCl 3, 100 MHz).
12 Figure S C NMR spectrum of compound 3 (CDCl 3, 100 MHz). Figure S3-4. HSQC spectrum of compound 3 (CDCl 3, 400, 100 MHz).
13 Figure S3-5. HMBC spectrum of compound 3 (CDCl 3, 400, 100 MHz). Figure S H- 1 H COSY spectrum of compound 3 (CDCl 3, 400 MHz).
14 Figure S3-7. NOESY spectrum of compound 3 (CDCl 3, 400 MHz). Figure S H NMR spectrum of compound 4 (CDCl 3, 400 MHz).
15 Figure S C DEPT135 spectrum of compound 4 (CDCl 3, 100 MHz). Figure S C NMR spectrum of compound 4 (CDCl 3, 100 MHz).
16 Figure S4-4. HSQC spectrum of compound 4 (CDCl 3, 400, 100 MHz). Figure S4-5. HMBC spectrum of compound 4 (CDCl 3, 400, 100 MHz).
17 Figure S H- 1 H COSY spectrum of compound 4 (CDCl 3, 400 MHz). Figure S4-7. NOESY spectrum of compound 4 (CDCl 3, 400 MHz).
18 Figure S H NMR spectrum of compound 5 (CDCl 3, 400 MHz). Figure S C DEPT135 spectrum of compound 5 (CDCl 3, 100 MHz).
19 Figure S C NMR spectrum of compound 5 (CDCl 3, 100 MHz). Figure S5-4. HSQC spectrum of compound 5 (CDCl 3, 400, 100 MHz).
20 Figure S5-5. HMBC spectrum of compound 5 (CDCl 3, 400, 100 MHz). Figure S5-6. NOESY spectrum of compound 5 (CDCl 3, 400 MHz).
21 Figure S H NMR spectrum of (R)-MTPA ester of compound 5 (pyridine-d5, 400 MHz). Figure S H NMR spectrum of (S)-MTPA ester of compound 5 (pyridine-d5, 400 MHz).
22 Figure S H NMR spectrum of compound 6 (CDCl 3, 400 MHz). Figure S C DEPT135 spectrum of compound 6 (CDCl 3, 100 MHz).
23 Figure S C NMR spectrum of compound 6 (CDCl 3, 100 MHz). Figure S6-4. HSQC spectrum of compound 6 (CDCl 3, 400, 100 MHz).
24 Figure S6-5. HMBC spectrum of compound 6 (CDCl 3, 400, 100 MHz). Figure S H- 1 H COSY spectrum of compound 6 (CDCl 3, 400 MHz).
25 Figure S6-7. NOESY spectrum of compound 6 (CDCl 3, 400 MHz). Figure S H NMR spectrum of (R)-MTPA ester of compound 6 (pyridine-d5, 400 MHz).
26 Figure S H NMR spectrum of (S)-MTPA ester of compound 6 (pyridine-d5, 400 MHz). Figure S H NMR spectrum of compound 7 (CDCl 3, 400 MHz).
27 Figure S C DEPT135 spectrum of compound 7 (CDCl 3, 100 MHz). Figure S C NMR spectrum of compound 7 (CDCl 3, 100 MHz).
28 Figure S7-4. HSQC spectrum of compound 7 (CDCl 3, 400, 100 MHz). Figure S7-5. HMBC spectrum of compound 7 (CDCl 3, 400, 100 MHz).
29 Figure S H- 1 H COSY spectrum of compound 7 (CDCl 3, 400 MHz). Figure S7-7. NOESY spectrum of compound 7 (CDCl 3, 400 MHz).
30 Figure S H NMR spectrum of (R)-MTPA ester of compound 8 (pyridine-d5, 400 MHz). Figure S H NMR spectrum of (S)-MTPA ester of compound 7 (pyridine-d5, 400 MHz).
31 Figure S H NMR spectrum of compound 8 (methanol-d 4, 400 MHz). Figure S C DEPT135 spectrum of compound 8 (methanol-d 4, 100 MHz).
32 Figure S C NMR spectrum of compound 8 (methanol-d 4, 100 MHz). Figure S8-4. HSQC spectrum of compound 8 (methanol-d 4, 400, 100 MHz).
33 Figure S8-5. HMBC spectrum of compound 8 (methanol-d 4, 400, 100 MHz). Figure S H- 1 H COSY spectrum of compound 8 (methanol-d 4, 400 MHz).
34 Figure S8-7. NOESY spectrum of compound 8 (methanol-d 4, 400 MHz).
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