Amyrisin B [5,7-dihydroxy-2- (4-((2-hydroxy-3-methylbut-3-en-1-yl)oxy)phenyl)-6-methoxy-4H-chromen-4-one]
IUPAC name: 5,7-Dihydroxy-2-(4-((2-hydroxy-3-methylbut-3-en-1-yl) oxy)phenyl)-6-methoxy-4H-chromen-4-one
Sub-class: O-Prenylated flavone
Chemical structure
Source: Amyris madrensis S. Watson (Family: Rutaceae); leaves and twigs
Molecular formula: C21H20O7
Molecular weight: 384
State: Yellow powder
Bioactivity studied: Anticancerous [IC50 = (17.5 ± 4.5) μM against PC-3 cancer cells]
Specific rotation: [α]20D +6.3° (MeOH, c 0.03)
UV (MeCN-H2O): λmax 274, 335 nm
1H-NMR (CDCl3, 500 MHz): δ 6.58 (1H, s, H-3), 6.60 (1H, s, H-8), 7.84 (2H, d, J = 9.0 Hz, H-2′ and H-6′), 7.05 (2H, d, J = 9.0 Hz, H-3′ and H-5′), 4.14 (1H, dd, J = 9.5, 3.2 Hz, H-1′′a), 4.04 (1H, t, J = 9.2 Hz, H-1′′b), 4.53 (1H, m, H-2′′), 5.19 (1H, s, H-4′′a), 5.06 (1H, s, H-4′′b), 1.86 (3H, s, H-5′′), 4.05 (3H, s, 6-OCH3), 13.01 (1H, s, 5-OH), 6.49 (1H, s, 7-OH).
13C-NMR (CDCl3, 125 MHz): δ 164.1 (C-2), 103.9 (C-3), 182.7 (C-4), 152.3 (C-5), 130.4 (C-6), 155.1 (C-7), 93.4 (C-8), 153.8 (C-9), 105.7 (C-10), 124.5 (C-1′), 128.3 (C-2′, C-6′), 115.1 (C-3′, C-5′), 161.7 (C-4′), 71.9 (C-1′′), 74.1 (C-2′′), 143.3 (C-3′′), 113.3 (C-4′′), 18.7 (C-5′′), 60.7 (C6-OCH3).
HSQC: δ 6.58 (H-3) vs δ 103.9 (C-3), δ 6.60 (H-8) vs δ 93.4 (C-8), δ 7.84 (H-2′/H-6′) vs δ 128.3 (C-2′/C-6′), δ 7.05 (H-3′/ H-5′) vs δ 115.1 (C-3′/C-5′), δ 4.14 (H-1′′a) and 4.04 (H-1′′b) vs δ 71.9 (C-1′′), δ 4.53 (H-2′′) vs δ 74.1 (C-2′′), δ 5.19 (H-4′′a) and 5.06 (H-4′′b) vs δ 113.3 (C-4′′), δ 1.86 (H-5′′) vs δ 18.7 (C-5′′), δ 4.05 (6-OCH3) vs δ 60.7 (C6-OCH3).
HMBC: δ 4.14 (H-1′′a) and 4.04 (H-1′′b) vs δ 161.7 (C-4′) indicating the presence of the prenyloxy group at C-4′.
HRMS: m/z 385.1299 ([M + H]+, Calcd. for C21H21O7, 385.1287).
Reference
Peng J, Hartley R M, Fest G A, Mooberry S L. (2012). Amyrisins A-C, O-prenylated flavonoids from Amyris madrensis. J Nat Prod 75: 494–496.
Amyrisin C [5,7-Dihydroxy-6-methoxy-2-(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyl)-4H-chromen-4-one]
IUPAC name: 5,7-Dihydroxy-6-methoxy-2-(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyl)-4H-chromen-4-one
Sub-class: O-Prenylated flavone
Chemical structure
Source: Amyris madrensis S. Watson (Family: Rutaceae); leaves and twigs
Molecular formula: C22H22O7
Molecular weight: 398
State: Yellow powder
Bioactivity studied: Anticancerous [IC50 = (23.05 ± 5.3) μM against PC-3 cancer cells]
UV (MeCN-H2O): λmax 275, 342 nm
1H-NMR (CDCl3, 500 MHz): δ 6.96 (1H, s, H-3), 6.98 (1H, s, H-8), 7.224 (1H, d, J = 2.1 Hz, H-2′), 6.97 (1H, d, J = 8.6 Hz, H-5′), 7.49 (1H, dd, J = 8.5, 2.1 Hz, H-6′), 4.67 (2H, d, J = 6.6 Hz, H-1′′), 5.52 (1H, t, J = 6.6 Hz, H-2′′), 1.77 (3H, s, H-4′′), 1.80 (3H, s, H-5′′), 4.05 (3H, s, 6-OCH3), 3.96 (3H, s, 3′-OCH3), 13.09 (1H, s, 5-OH).
13C-NMR (CDCl3, 125 MHz): δ 164.1 (C-2), 103.9 (C-3), 182.7 (C-4), not detected (C-5), 130.1 (C-6), 155.0 (C-7), 93.4 (C-8), 153.1 (C-9), 105.8 (C-10), 123.5 (C-1′), 108.8 (C-2′), 149.6 (C-3′), 151.6 (C-4′), 112.7 (C-5′), 120.1 (C-6′), 66.1 (C-1′′), 119.3 (C-2′′), 138.7 (C-3′′), 18.0 (C-4′′), 25.5 (C-5′′), 61.0 (C6-OCH3), 56.3 (C3′-OCH3).
HMBC: δ 4.67 (H-1′′) vs δ 151.6 (C-4′), δ 3.96 (3′-OCH3) vs δ 149.6 (C-3′) (selected HMBC correlations were shown).
HRMS: m/z 399.1447 ([M + H]+, Calcd. for C22H23O7, 399.1444).
Reference
Peng J, Hartley RM, Fest GA, Mooberry SL. (2012). Amyrisins A-C, O-prenylated flavonoids from Amyris madrensis. J Nat Prod 75: 494–496.
Angepubebisin
IUPAC name: (E)-(R)-(7-methoxy-2-oxo-2H-chromen-6-yl)((S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)methyl 2-methylbut-2-enoate
Sub-class: Coumarin
Chemical structure
Source: Angelica pubescens Maxim. f. biserrata Shan et Yuan (Family: Umbelliferae); roots
Molecular formula: C23H28O7
Molecular weight: 416
State: Amorphous powder
Specific rotation: [α]20D −59.0° (CHCl3, c 0.09)
UV (MeOH): λmax ...