New Acylated Anthocyanins from Purple Yam and Their Antioxidant Activity

Supporting information

New acylated anthocyanins from purple yam and their antioxidant activity

Chiemi Moriyaa,†, Takahiro Hosoyaa,†, Sayuri Agawaa, Yasumasa Sugiyamab, Ikuko Kozonec, Kazuo Shin-yad, Norihiko Teraharae and Shigenori Kumazawaa,*

aDepartment of Food and Nutritional Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan; bBioorganic Chemistry Research Group, Faculty of Fisheries, Kagoshima University, 4-50-20 Shimoarata, Kagoshima 890-0056, Japan; cJapan Biological Informatics Consortium (JBIC), 2-4-7 Aomi, Koto-ku, Tokyo 135-0064, Japan; dNational Institute of Advanced Industrial Science and Technology (AIST), 2-4-7 Aomi, Koto-ku, Tokyo 135-0064, Japan; eDepartment of Food Science and Technology, Faculty of Health and Nutrition, Minami-Kyushu University, 5-1-2 Kirishima, Miyazaki 880-0032, Japan

*Corresponding author. Email:

†These authors contributed equally to this study.

Figure S1. Positive HR-ESIMS spectrum of alatanin D (1) S4

Figure S2. Positive HR-ESIMS/MS spectrum of alatanin D (1) S5

Figure S3. 1H NMR spectrum of alatanin D (1) S6

Figure S4. 13C NMR spectrum of alatanin D (1) S7

Figure S5. HSQC spectrum of alatanin D (1) S8

Figure S6. 1H-1HCOSY spectrum of alatanin D (1) S9

Figure S7. HMBC spectrum of alatanin D (1) S10

Figure S8. ROESY spectrum of alatanin D (1) S11

Figure S9. 1D-TOCSY spectrum of alatanin D (1) S12

Figure S10. 1D-TOCSY spectrum of alatanin D (1) S13

Figure S11. 1D-TOCSY spectrum of alatanin D (1) S14

Figure S12. 1H-1H 2D-TOCSY spectrum of alatanin D (1) S15

Figure S13. 1H-13C 2D-TOCSY spectrum of alatanin D (1) S16

Figure S14. Positive HR-ESIMS spectrum of alatanin E (2) S17

Figure S15. Positive HR-ESIMS/MS spectrum of alatanin E (2) S18

Figure S16. 1H NMR spectrum of alatanin E (2) S19

Figure S17. 13C NMR spectrum of alatanin E (2) S20

Figure S18. HSQC spectrum of alatanin E (2) S21

Figure S19. 1H-1HCOSY spectrum of alatanin E (2) S22

Figure S20. HMBC spectrum of alatanin E (2) S23

Figure S21. ROESY spectrum of alatanin E (2) S24

Figure S22. 1D-TOCSY spectrum of alatanin E (2) S25

Figure S23. 1D-TOCSY spectrum of alatanin E (2) S26

Figure S24. 1D-TOCSY spectrum of alatanin E (2) S27

Figure S25. 1H-1H 2D-TOCSY spectrum of alatanin E (2) S28

Figure S26. Positive HR-ESIMS spectrum of alatanin F (3) S29

Figure S27. Positive HR-ESIMS/MS spectrum of alatanin F (3) S30

Figure S28. 1H NMR spectrum of alatanin F (3) S31

Figure S29. 13C NMR spectrum of alatanin F (3) S32

Figure S30. HSQC spectrum of alatanin F (3) S33

Figure S31. 1H-1HCOSY spectrum of alatanin F (3) S34

Figure S32. HMBC spectrum of alatanin F (3) S35

Figure S33. ROESY spectrum of alatanin F (3) S36

Figure S34. 1D-TOCSY spectrum of alatanin F (3) S37

Figure S35. 1D-TOCSY spectrum of alatanin F (3) S38

Figure S36. Positive HR-ESIMS spectrum of alatanin G (4) S39

Figure S37. Positive HR-ESIMS/MS spectrum of alatanin G (4) S40

Figure S38. 1H NMR spectrum of alatanin G (4) S41

Figure S39. 13C NMR spectrum of alatanin G (4) S42

Figure S40. HSQC spectrum of alatanin G (4) S43

Figure S41. 1H-1HCOSY spectrum of alatanin G (4) S44

Figure S42. HMBC spectrum of alatanin G (4) S45

Figure S43. ROESY spectrum of alatanin G (4) S46

Figure S44. 1D-TOCSY spectrum of alatanin G (4) S47

Figure S45. 1D-TOCSY spectrum of alatanin G (4) S48

S31

Figure S1. Positive HR-ESIMS spectrum of alatanin D (1)

Figure S2. Positive HR-ESIMS/MS spectrum of alatanin D (1)

Figure S3. 1H NMR spectrum of alatanin D (1)

Figure S4. 13C NMR spectrum of alatanin D (1)

Figure S5. HSQC spectrum of alatanin D (1)

Figure S6. 1H-1HCOSY spectrum of alatanin D (1)

Figure S7. HMBC spectrum of a alatanin D (1)

Figure S8. ROESY spectrum of alatanin D (1)

Figure S9. 1D-TOCSY spectrum of alatanin D (1)

Figure S10. 1D-TOCSY spectrum of alatanin D (1)

Figure S11. 1D-TOCSY spectrum of alatanin D (1)

Figure S12. 1H-1H 2D-TOCSY spectrum of alatanin D (1)

Figure S13. HSQC-TOCSY spectrum of alatanin D (1)

Figure S14. Positive HR-ESIMS spectrum of alatanin E (2)

Figure S15. Positive HR-ESIMS/MS spectrum of alatanin E (2)

Figure S16. 1H NMR spectrum of alatanin E (2)

Figure S17. 13C NMR spectrum of alatanin E (2)

Figure S18. HSQC spectrum of alatanin E (2)

Figure S19. 1H-1HCOSY spectrum of alatanin E (2)

Figure S20. HMBC spectrum of alatanin E (2)

Figure S21. ROESY spectrum of alatanin E (2)

Figure S22. 1D-TOCSY spectrum of alatanin E (2)

Figure S23. 1D-TOCSY spectrum of alatanin E (2)

Figure S24. 1D-TOCSY spectrum of alatanin E (2)

Figure S25. 1H-1H 2D-TOCSY spectrum of alatanin E (2)

Figure S26. Positive HR-ESIMS spectrum of alatanin F (3)

Figure S27. Positive HR-ESIMS/MS spectrum of alatanin F (3)

Figure S28. 1H NMR spectrum of alatanin F (3)

Figure S29. 13C NMR spectrum of alatanin F (3)

Figure S30. HSQC spectrum of alatanin F (3)

Figure S31. 1H-1HCOSY spectrum of alatanin F (3)

Figure S32. HMBC spectrum of alatanin F (3)

Figure S33. ROESY spectrum of alatanin F (3)

Figure S34. 1D-TOCSY spectrum of alatanin F (3)

Figure S35. 1D-TOCSY spectrum of alatanin F (3)

Figure S36. Positive HR-ESIMS spectrum of alatanin G (4)

Figure S37. Positive HR-ESIMS/MS spectrum of alatanin G (4)

Figure S38. 1H NMR spectrum of alatanin G (4)

Figure S39. 13C NMR spectrum of alatanin G (4)

Figure S40. HSQC spectrum of alatanin G (4)

Figure S41. 1H-1HCOSY spectrum of alatanin G (4)

Figure S42. HMBC spectrum of alatanin G (4)

Figure S43. ROESY spectrum of alatanin G (4)

Figure S44. 1D-TOCSY spectrum of alatanin G (4)

Figure S45. 1D-TOCSY spectrum of alatanin G (4)

S31