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. Author manuscript; available in PMC: 2016 Dec 24.
Published in final edited form as: J Nat Prod. 2015 Dec 7;78(12):2917–2923. doi: 10.1021/acs.jnatprod.5b00519

Table 1.

1H and 13C NMR Data for 1, 2, 5 (CDCl3)a and 6 (MeOH-d4)a

berkchaetoazaphilone A (1) berkchaetoazaphilone B (2) berkchaetoazaphilone C (5) berkchaetorubramine (6)
no. δC, type δH (J in Hz) δC, type δH (J in Hz) δC, type δH (J in Hz) δC, type δH (J in Hz)
1 147.5, CH 7.35, bs 147.7, CH 7.44, bs 146.5, CH 7.36, s 144.9, CH 8.30, s
3 159.6, C 161.0, C 158.9, C 154.7, C
4 108.5, CH 6.06, s 107.6, CH 6.12, s 108.4, CH 6.03, s 120.0, CH 7.01, s
4a 144.1, C 145.0, C 145.3, C 153.7, C
5 106.0, CH 5.35, bs 105.2, CH 5.35, bs 103.4, CH 5.35, s 98.6, CH 6.69, s
6 191.5, C 189.1, C 198.5, C 174.2, C
7 82.8, C 84.1, C 73.1, C 87.1, C
8 42.7, CH 3.83, d (12.2) 72.1, C 40.5, CH 3.35, dd (10.1, 3.0) 196.6, C
8a 114.6, C 108.3, C 120.5, C 102.3, C
9 22.6, CH3 1.55, s 18.7, CH3 1.57, s 26.7, CH3 1.28, s 30.8, CH3 1.65, s
10 42.8, CH2 2.49, m 42.7, CH2 2.52, d (6.2) 42.9, CH2 2.47, m 41.4, CH2 2.81, m
11 65.6, CH 4.14, m 65.4, CH 4.14, m 65.6, CH 4.14, m 68.4, CH 4.44, bm
12 23.2, CH3 1.29, d (6.5) 23.7, CH3 1.27, d (6.1) 23.7, CH3 1.26, d (6.4) 23.9, CH3 1.30, d (6.1)
13 168.5, C 165.5, C 173.9, C
14 56.4, CH 3.70, d (12.2) 66.8, C 40.4, CH2 3.00, dd (18.6, 3.0)
2.28, m		 122.6, C
15 202.3, C 195.6, C 209.8, C 199.0, C
16 42.8, CH2 3.13, dd (18.4, 4.0)
2.48, dd (18.4, 7.9)		 42.0, CH2 2.80, dt (17.5, 7.0)
2.58, dt (17.5, 7.0)		 43.5, CH2 2.31, m
2.23, m		 40.8, CH2 2.96, m
2.81, m
17 23.7, CH2 1.24, bs 23.2, CH2 1.23, bs 23.5, CH2 1.47, bs 23.5, CH2 1.29, bs
18 28.9, CH2 1.24, bs 28.9, CH2 1.23, bs 29.2, CH2 1.24, bs 30.6, CH2 1.29, bs
19 29.2, CH2 1.24, bs 29.2, CH2 1.23, bs 29.4, CH2 1.24, bs 30.7, CH2 1.29, bs
20 29.4, CH2 1.24, bs 29.3, CH2 1.23, bs 29.4, CH2 1.24, bs 30.8, CH2 1.29, bs
21 29.4, CH2 1.24, bs 29.3, CH2 1.23, bs 29.2, CH2 1.24, bs 30.8, CH2 1.29, bs
22 31.8, CH2 1.24, bs 31.8, CH2 1.23, bs 31.8, CH2 1.24, bs 33.2, CH2 1.29, bs
23 23.0, CH2 1.24, bs 22.6, CH2 1.23, bs 22.6, CH2 1.24, bs 26.6, CH2 1.29, bs
24 14.1, CH3 0.85, t (6.9) 14.1, CH3 0.85, t (7.0) 14.1, CH3 0.85, t (6.8) 14.6, CH3 0.90, t (7.0)
1′ 58.1, CH2 4.29, bm
4.11, bm
2′ 61.8, CH2 3.87, bm
a

All assignments are based on COSY, NOE, HSQC and HMBC experiments, 500 MHz for 1H NMR and 125 MHz for 13C NMR.