A Prenylated Flavonoid from the Methanol Fraction of Breadfruit Root (Artocarpus communis)

Abstract

Breadfruit (Artocarpus communis) is a tropical fruit plant that belongs to the genus Artocarpus of the Moraceae family. Prenylated flavonoid compounds were isolated from the methanol fraction of breadfruit root wood using maceration, partitioning, and chromatography methods, while characterization was carried out through phytochemical tests and ¹H-NMR spectrum data analysis. The K₁D₂ (P₁) compound obtained was a yellow solid with a mass of 5 mg. The phytochemical test of the K₁D₂ (P₁) compound gave positive results for the flavonoid group. The ¹H-NMR spectrum data (CDCl₃, 500 MHz) of compound K₁D₂ (P₁) showed a typical chemical shift at δ_H 13.42 (1H, s, 5-OH) for the hydroxy groups associated with carbonyl; 7.68 (1H, d, J = 8.5 Hz, H-6 ′); 6.71 (1H, dd, J = 16.0; 7.1 Hz, H-10); 6.56 (1H, d, J = 16.0 Hz, H-9); 6.54 (1H, dd, J = 8.5; 1.8 Hz, H-5 ′); 6.46 (1H, s, H-3); 6.42 (1H, d, J = 1.8 Hz, H-3 ′); 6.26 (1H, d, J = 9.3 Hz, H-14); 5.42 (1H, d, J = 9.3 Hz, H-15); 3.94 (3H, s, 2′-OCH₃); 2.47 (1H, m, H-11); 1.97 (3H, s, H-17); 1.69 (3H, s, H-18), and 1.10 (6H, d, J = 6.7 Hz, H-12 and H-13). Based on the results of phytochemical tests and analysis of ¹H-NMR spectrum data compared with literature data, it showed that the isolated K₁D₂ (P₁) compound is 4 ′, 5-dihydroxy-6,7- (2,2-dimethylpirano) -2'-methoxy- 8γ, γ-dimethylallylflavone (1).