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. 2024 Apr 5;87(4):1003–1012. doi: 10.1021/acs.jnatprod.3c01288

Table 1. NMR Spectroscopic Data (1H 500 and 13C 125 MHz) of Oblarotenoids E (1), F (2) (CD2Cl2a), and G (CDCl3).

  1
2
3
position δC, type δH (J in Hz) HMBCb δC, type δH (J in Hz) HMBC δC, type δH (J in Hz) HMBC
1 106.6, CH 6.31 s C-1a, C-2, C-3, C-4a, C-12a 105.9, CH 6.54 s C-1a, C-2, C-3, C-4a, C-12a 107.1, CH 8.32 s C-2, C-3, C-4a, C-12a
1a 109.4, C     109.9, C     111.8, C    
2 138.9, C     149.5, C     142.9, C    
3 136.3, C     142.4, C     147.4, C    
4 136.9, C     99.3, CH 6.46 s C-1a, C-2, C-3 98.7, CH 6.53 s C-1a, C-2, C-3
4a 133.2, C     149.5, C     147.5, C    
6 66.8, CH2 4.65 dd (12.5, 2.6) C-4a, C-6a, C-12a 64.0, CH2 4.58 dd (13.5, 2.6) C-4a, C-6a, C-12a 65.0, CH2 4.96 s C-4a, C-6a, C-12a
4.21 br d (12.5) C-4a,C-6a 4.46 d (13.5, 2.6) C-4a,C-6a
6a 72.7, CH 4.94 dd (2.6) C-1a, C-4a, C-6, C-12, C-12a 76.4, CH 4.56 br d (3.6) C-1a, C-4a, C-6, C-12, C-12a 156.8, C    
7a 163.0, C     157.5, C     156.7, C    
8 100.9, CH 6.44 d (2.3) C-7a, C-9, C-10, C-11a 100.3, CH 6.40 s C-7a, C-9, C-10, C-11a 100.3, CH 6.83 d (2.2) C-7a, C-9, C-10, C-11a
9 167.0, C     157.3, C     164.0, C    
10 110.9, CH 6.59 dd (8.9, 2.3) C-8, C-9, C-11a 145.3, C   C-8, C-9, C-11a 114.7, CH 7.00 dd (8.9, 2.2) C-8, C-11a
11 129.6, CH 7.85 d (8.9) C-7a, C-9, C-12 106.9, CH 7.25 s C-7a, C-9, C-12 127.9, CH 8.20 d (8.9) C-7a, C-9, C-12
11a 113.1, C     109.5, C     118.7, C    
12 189.0, CO     191.3, CO     174.2, CO    
12a 45.0, CH 3.81c C-1a, C-4, C-6 67.9, C     112.3, C    
OCH2O 102.7, CH2 5.97 d (1.4); 5.91 d (1.4) C-3, C-4 101.5, CH2 5.83 d (1.4); 5.86 d (1.4) C-2, C-3 101.5, CH2 5.96 s C-2, C-3
OMe-2 57.2, CH3 3.73 s C-2            
OMe-9 56.2, CH3 3.81 s C-9 56.4, CH3 3.86 s C-9 56.0, CH3 3.92 s C-9
OMe-10       56.5, CH3 3.88 s C-10      
a

CD2Cl2 was used due to the gradual color change observed in the slightly acidic CDCl3.

b

HMBC correlations, optimized for 6 Hz, are from the stated proton(s) to the indicated carbon.

c

Signal overlapping with that of OMe-9.