Macrophylloflavone: A New Biflavonoid from Garcinia macrophylla Mart. (Clusiaceae) for Antibacterial, Antioxidant, and Anti-Type 2 Diabetes Mellitus Activities

Table 1

Comparison of ¹H-NMR spectra in 3-flavanone-6″-flavone of macrophylloflavone (1) with a number of biflavonoid 3-flavanone-8″-flavone.

Compound	Position	2	3	4	5	6	7	8	9	10	1’	2’	3’	4’	5’	6’
Macrophylloflavone (1)	δH (ppm) (a)	5.75 (1H, d, J = 11.90 Hz)	4.83 (1H, d, J = 11.95 Hz)	—	—	5.96 (1H, d, J = 2.15 Hz)	—	5.98 (1H, d, J = 2.15 Hz)	—	—	—	7.07 (1H, d, J = 8.30 Hz)	6.64 (1H, d, J = 8.05 Hz)	—	6.43 (1H, d, J = 8.10 Hz)	7.10 (1H, d, J = 8.25 Hz)
Morelloflavone (2) [37]	δH (ppm) (b)	4.05 (1H, d, J = 12.00 Hz)	4.95 (1H, d, J = 12.00 Hz)	—	—	4.05 (1H, d)	—	4.05 (1H, d)	—	—	—	4.05 (1H, d)	4.05 (1H, d)	—	4.05 (1H, d)	4.05 (1H, d)
Morelloflavone (2) [38]	δH (ppm) (c)	5.87 (1H, d, J = 12.00 Hz)	5.07 (1H, d, J = 12.00 Hz)	—	—	6.10 (1H, d, J = 2.00 Hz)	—	6.38 (1H, d, J = 2.00 Hz)	—	—	—	7.30 (1H, d, J = 8.00 Hz)	6.63 (1H, d, J = 8.00 Hz)	—	6.63 (1H, d, J = 8.00 Hz)	7.30 (1H, d, J = 8.00 Hz)
Morelloflavone (2) [39]	δH (ppm) (d)	5.73 (1H, d, J = 12.00 Hz)	4.86 (1H, d, J = 12.00 Hz)	—	—	5.97 (1H, s)	—	5.97 (1H, s)	—	—	—	7.08 (1H, d, J = 9.00 Hz)	6.50 (1H, d, J = 9.00 Hz)	—	6.50 (1H, d, J = 9.00 Hz)	7.08 (1H, d, J = 9.00 Hz)
Morelloflavone (2) [40]	δH (ppm) (e)	5.64 (1H, d, J = 12.00 Hz)	4.83 (1H, d, J = 12.00 Hz)	—	—	5.95 (1H, s)	—	5.95 (1H, s)	—	—	—	7.09 (1H, d, J = 8.00 Hz)	6.50 (1H, d, J = 8.00 Hz)	—	6.50 (1H, d, J = 8.00 Hz)	7.09 (1H, d, J = 8.00 Hz)
Morelloflavone (2) [41]	δH (ppm) (f)	5.72 (1H, d, J = 12.00 Hz)	4.86 (1H, d, J = 12.00 Hz)	—	—	5.91 (1H, s)	—	5.91 (1H, s)	—	—	—	7.08 (1H, d, J = 8.00 Hz)	6.32 (1H, d, J = 8.00 Hz)	—	6.32 (1H, d, J = 8.00 Hz)	7.08 (1H, d, J = 8.00 Hz)
Morelloflavone (2) [42]	δH (ppm) (g)	5.88 (1H, d, J = 12.40 Hz)	5.00 (1H, d, J = 12.40 Hz)	—	—	6.04 (1H, br, s)	—	6.04 (1H, br, s)	—	—	—	7.25 (1H, d, J = 8.00 Hz)	6.54 (1H, d, J = 8.00 Hz)	—	6.54 (1H, d, J = 8.00 Hz)	7.25 (1H, d, J = 8.00 Hz)
Morelloflavone-4‴-O-β-D-glucoside (3) [30]	δH (ppm) (h)	5.89 (1H, d, J = 12.61 Hz)	4.93 (1H, d, J = 12.61 Hz)	—	—	5.94 (1H, d, J = 4.60 Hz)	—	6.53 (1H, d, J = 5.00 Hz)	—	—	—	6.63 (1H, dd, J = 7.60 Hz)	7.15 (1H, dd, J = 7.97 Hz)	—	7.15 (1H, dd, J = 7.97 Hz)	6.63 (1H, dd, J = 7.60 Hz)
Volkensiflavone (4) [43]	δH (ppm) (i)	4.30 (1H, d, J = 14.00 Hz)	5.10 (1H, d, J = 14.00 Hz)	—	—	3.9 (1H, s)	—	4.00 (1H, s)	—	—	—	2.90 (1H, d)	3.40 (1H, d)	—	3.40 (1H, d)	2.90 (1H, d)
Compound	Position	2″	3″	4″	5″	6″	7″	8″	9″	10″	1‴	2‴	3‴	4‴	5‴	6‴
Macrophylloflavone (1)	δH (ppm) (a)	—	6.39 (1H, s)	—	—	—	—	6.25 (1H, s)	—	—	—	7.33 (1H, m)	—	—	6.91 (1H, d, J = 8.35 Hz)	7.29 (1H, d, J = 8.40 Hz)
Morelloflavone (2) [37]	δH (ppm) (b)	—	3.90 (1H, s)	—	—	4.05 (1H, s)	—	—	—	—	—	4.95 (1H, d)	—	—	4.95 (1H, d)	4.95 (1H, d)
Morelloflavone (2) [38]	δH (ppm) (c)	—	6.55 (1H, s)	—	—	6.08 (1H, s)	—	—	—	—	—	7.52 (1H, m)	—	—	6.68 (1H, d, J = 8.00 Hz)	7.52 (1H, m)
Morelloflavone (2) [39]	δH (ppm) (d)	—	6.43 (1H, s)	—	—	6.20 (1H, s)	—	—	—	—	—	7.72 (1H, d, J = 2.00 Hz)	—	—	6.80 (1H, d, J = 9.00 Hz)	7.19 (1H, dd, J = 9.00, 2.00 Hz)
Morelloflavone (2) [40]	δH (ppm) (e)	—	6.44 (1H, s)	—	—	6.19 (1H, s)	—	—	—	—	—	7.37 (1H, m)	—	—	6.84 (1H, d, J = 8.00 Hz)	7.37 (1H, m)
Morelloflavone (2) [41]	δH (ppm) (f)	—	6.53 (1H, s)	—	—	6.17 (1H, s)	—	—	—	—	—	7.31 (1H, br, s)	—	—	7.20 (1H, br)	6.80 (1H, br)
Morelloflavone (2) [42]	δH (ppm) (g)	—	6.48 (1H, s)	—	—	6.32 (1H, s)	—	—	—	—	—	7.52 (1H, br, s)	—	—	7.03 (1H, d, J = 8.00 Hz)	7.54 (1H, br, d, J = 8.00 Hz)
Morelloflavone-4‴-O-β-D-glucoside (3) [30]	δH (ppm) (h)	—	6.76 (1H, s)	—	—	6.59 (1H, s)	—	—	—	—	—	7.32 (1H, s)	—	—	6.97 (1H, d, J = 8.10 Hz)	7.49 (1H, dd, J = 8.10 Hz)
Volkensiflavone (4) [43]	δH (ppm) (i)	—	3.45 (1H, s)	—	—	3.70 (1H, s)	—	—	—	—	—	2.40 (1H, d)	3.20 (1H, d)	—	3.20 (1H, d)	2.40 (1H, d)

Solvent and magnetic field strength for (a) CD₃OD, 500 MHz; (b) acetone-d₆; (c) DMSO-d₆; (d) DMSO-d₆, 100 MHz; (e) DMSO-d₆; (f) DMSO-d₆, 100 MHz; (g) CDCl₃, 400 MHz; (h) DMSO-d₆, 400 MHz; and (i) hexadeuteriodimethylsulphoxide, 100 MHz.