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. Author manuscript; available in PMC: 2020 Jun 25.
Published in final edited form as: J Nat Prod. 2018 Nov 29;81(12):2716–2721. doi: 10.1021/acs.jnatprod.8b00650

Table 1.

NMR Spectroscopic Data (1H 600 MHz, 13C 150 MHz, CDCl3) for 1–3

anaephene A (1) anaephene B (2) anaephene C (3)
No δC, Type δH (J in Hz) HMBC COSY δC, Type δH (J in Hz) HMBC COSY δC, Type δH (J in Hz) HMBC COSY
1 155. 6, C 155.6, C 155.6, C
2 115.4, CH 6.65, br s 1, 3, 4 6, 1’ 115.4, CH 6.65, br s 1, 3, 4 6, 1’ 115.5, CH 6.66, br s 1, 3, 4 6, 1’
3 145.0, C 144.9, C 144.0, C
4 121.1, CH 6.75, d (7.7) 1, 2, 3 5, 6, 1’ 5 121.1, CH 6.75, d (7.7) 1, 2, 3 5, 6, 1’ 5 121.1, CH 6.76, d (7.7) 1, 2, 3 5, 6, 1’ 5
5 129.5, CH 7.13, t (7.7) 1, 3, 4 6 4, 6 129.6, CH 7.14, t (7.7) 1, 3, 4 6 4, 6 129.6, CH 7.14, t (7.7) 1, 3, 4 6 4, 6
6 112.6, CH 6.63, m 1, 2, 4 5 112.7, CH 6.64, d (2.6) 1, 2, 4 5 112.9, CH 6.64, d (2.6) 1, 2, 4 5
1’ 35.8, CH2 2.55, t (7.7) 2, 3, 4 2’ 2’ 35.8, CH2 2.56, t (7.7) 2, 3, 4 2’ 2’ 35.9, CH2 2.65, t (7.6) 2, 3, 4 2’
2’ 30.9, CH2 1.60, m 3, 1’, 3’ 4’ 1’, 3’ 30.8, CH2 1.60, m 3, 1’, 3’ 4’ 1’, 3’ 34.4, CH2 2.36, m 1’, 3’,4’ 1’, 3’
3’ 29.4, CH2 1.38, m 2’, 4’, 5’ 2’, 4’ 29.2, CH2 1.39, m 1’, 5’ 2’, 4’ 131.0, CH 5.59, m 1’, 2’ 4’
4’ 32.6, CH2 2.01, m 3’, 5’, 6’ 3’ 32.5, CH2 2.01, m 3’, 5’ 3’, 5’ 131.1, CH 6.04, m 3’, 5’ 3’
5’ 130.3, CH 5.38, m 4’, 6’ 6’ 131.4, CH 5.43, dt (15.5, 6.7) 4’, 6’ 130.4, CH 5.99, m 6’
6’ 130.6, CH 5.40, m 5’,7’ 5’, 7’ 129.4, CH 5.36, dt (15.5, 6.7) 8’ 5’, 7’ 133.0, CH 5.57, m 5’
7’ 34.9, CH2 1.95, m 6’, 8’, 9’ 6’, 8’ 31.6, CH2 2.09, m 6’, 8’, 9’ 6,’8’ 34.8, CH2 2.03, m 6’, 9’ 8’
8’ 22.9, CH2 1.34, m 6’, 9’ 7’, 9’ 28.5, CH2 1.58, m 10’ 7’, 9’ 26.6, CH2 1.40, m 6’, 7’, 9’ 7’, 9’
9’ 13.8, CH3 0.88, t (7.4) 7’, 8’ 8’ 17.9, CH2 2.18, m 11’ 11’ 13.9, CH3 0.90, t (7.4) 8’ 8’
10’ 87.6, C
11’ 68.4, CH 1.95, t (2.6) 9’
1-OH 4.79, br s 4.66, s 1, 2, 6 4.66, s 1, 2, 6