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. Author manuscript; available in PMC: 2008 Jul 1.
Published in final edited form as: J Nat Prod. 2008 Jan 15;71(2):199–207. doi: 10.1021/np0705763

Table 1.

1H (400 MHz) and 13C (75.4 MHz) NMR Spectroscopic Data (pyridine-d5) of Demycarosyl-3D-β-d-digitoxosyl-MTM (1) and Deoliosyl-3C-α-l-digitoxosyl-MTM (2)

1
 2
pos. δC, mult. δH (J in Hz) HMBC NOESY δC δH (J in Hz) HMBC NOESY
1 204.3, qC 204.2
2 78.7, CH 4.96 d (11.6) C-1, C-1C, C-3, C-4, C-1′ H-1C, H-3, H-4ax, H-4eq 77.9 4.93 d (11.6) C-1, C-1C, C-3, C-4, C-1′ H-1C, H-3, H-4ax, H-4eq
3 42.8, CH 3.48 m C-2, C-4, C-1′ H-2, H-4ax, H-4eq, H-1′ 42.8 3.41 m C-2, C-4, C-1′ H-2, H-4ax, H-4eq, H-1′
4ax 28.5, CH2 3.11 dd (15.9 and 3.6) C-2, C-3, C-1′ H-3, H-2 28.2 3.08 dd (15.9 and 3.6) C-2, C-3, C-1′ H-3, H-2
4eq 3.27 dd (15.9 and 13.0) H-3, H-2 3.26 dd (15.9 and 13.0)
4a 137.2, qC 137.2
5 102.2, CH 7.05 s C-6, C-8a, C-7, C-10 H-10, H-1A, H-5A 102.1 7.04 s C-6, C-8a, C-7, C-10 H-10, H-1A, H-5A
6 160.4, qC 160.4
7 111.7, qC 111.6
7-CH3 9.4, CH3 2.47 s C-6, C-7, C-8 9.4 2.47 s C-6, C-7, C-8
8 156.9, qC 157.0
8a 109.4, qC 109.4
9 165.7, qC 165.7
9a 108.9, qC 108.9
10 117.4, CH 6.63 s C-5, C-8a, C-9a, C-10a H-5, H-1A, H-4ax, H-4eq 117.4 6.61 s C-5, C-8a, C-9a, C-10a H-5, H-1A, H-4ax, H-4eq
10a 139.5, qC 139.4
1′ 83.1, CH 5.49 d (1.2) C-2, C-3, C-4, 1′-OCH3, C-2′ H-2, H-3, 1′-OCH3 83.1 5.46 d (1.2) C-2, C-3, C-4, 1′-OCH3, C-2′ H-2, H-3, 1′-OCH3
1′-OCH3 59.1, CH3 3.69 s C-1′, C-2′, C-3 59.4 3.69 s C-1′, C-2′, C-3
2′ 213.5, qC 213.4
3′ 81.4, CH 4.70 d (2.8) C-2′, C-4′, C-5′ H-4′, H-5′ 81.3 4.71 d (2.8) C-2′, C-4′, C-5′ H-4′, H-5′
4′ 69.6, CH 4.84 dq (6.2 and 2.8) C-2′, C-3′, C-5′ H-5′, H-3′ 69.6 4.84 dq (6.2 and 2.8) C-2′, C-3′, C-5′ H-5′, H-3′
5′ 19.7, CH3 1.60 d (6.2) C-3′, C-4′ H-4′, H-3′ 21.1 1.58 d (6.2) C-3′, C-4′ H-4′, H-3′
1A 97.9, CH 5.68 dd (9.6 and 2.0) C-6 H-3A, H-5A, H-2Aax, H-2Aeq, H-5, H-10 97.9 5.67 dd (9.6 and 2.0) C-6 H-5, H-10, H-3A, H-5A, H-2Aax, H-2Aeq
2Aax 38.0, CH2 2.25 ddd (12, 12 and 9.6) C-1A, C-3A, C-4A H-1A, H-4A, H-2Aeq 37.7 2.24 ddd (12, 12 and 9.6) C-1A, C-3A H-1A, H-4A
2Aeq 2.72 ddd (12, 5.0 and 2.0) H-1A, H-3A, H-2Aax 2.73 ddd (12, 5.0 and 2.0) H-1A
3A 80.1, CH 4.29 ddd (12, 9.0 and 5.0) C-1B, C-4A H-1A, H-1B, H-5A, H-2Aax, H-2Aeq 80.1 4.29 ddd (12, 9.0 and 5.0) C-1B, C-4A H-1A, H-1B, H-5A, H-2Aeq
4A 76.1, CH 3.63 t (9.0 Hz) C-3A, C-5A, C-6A H-2Aax, H3-6A 76.1 3.63 t (9.0) C-3A, C-5A, C-6A H-2Aax, H3-6A
5A 73.9, CH 4.00 dq (9.0 and 6.0) C-1A, C-3A, C-4A, C-6A H-1A, H-3A, H3-6A 73.9 4.00 dq (9.0 and 6.0) C-4A, C-6A H-1A, H-3A, H3-6A
6A 19.4, CH3 1.71 d (6.0) C-4A, C-5A H-4A, H-5A 19.6 1.71 d (6.0) C-4A, C-5A H-4A, H-5A
1B 99.4, CH 5.05 dd (9.6 and 2.0) C-3A H-2Bax, H-2Beq, H-3A, H-3B, H-5B 99.3 5.05 dd (9.6 and 2.0) C-3A H-3A, H-3B, H-5B, H-2Bax, H-2Beq
2Bax 41.6, CH2 2.15 ddd (12, 12 and 9.6) C-1B, C-3B, C-4B H-1B, H-4B 41.6 2.17 ddd (12, 12 and 9.6) C-1B, C-3B H-1B, H-4B
2Beq 2.65 ddd (12, 5.0 and 2.0) H-1B 2.65 ddd (12, 5.0 and 2.0) H-1B
3B 72.4, CH 4.16 ddd (12, 9.0 and 5.0) C-4B H-2Beq, H-1B, H-5B 72.4 4.15 ddd (12, 9.0 and 5.0) C-1B, C-4B H-1B, H-5B
4B 78.7, CH 3.58 t (9.0) C-3B, C-5B, C-6B H-2Bax, H3-6B 78.7 3.58 t (9.0) C-3B, C-5B, C-6B H-2Bax, H-3B, H-5B, H3-6B
5B 74.6, CH 3.75 dq (9.0 and 6.0) C-1B, C-3B, C-4B, C-6B H-1B, H-3B, H3-6B 74.0 3.75 dq (9.0 and 6.2) C-4B, C-6B H-1B, H-3B, H-4B, H3-6B
6B 19.1, CH3 1.64 d (6.0) C-4B, C-5B H-5B 19.3 1.64 d (6.2) C-4B, C-5B H-4B, H-5B
1C 101.9, CH 5.39 dd (9.6 and 2.0) C-2 H-2, H-3C, H-5C, H-2Ceq 101.9 5.37 dd (9.6 and 2.0) C-2 H-2, H-3C, H-5C, H-2Ceq, H-2Cax
2Cax 38.7, CH2 2.02 ddd (12, 12 and 9.6) C-1C, C-3C, C-4C H-4C 37.7 1.93 ddd (12, 12 and 9.6) C-3C H-4C
2Ceq 2.99 ddd (12, 5.0 and 2.0) H-1C 2.98 ddd (12, 5.0 and 2.0) H-1C, H-1D, H-3C, H-2Cax
3C 81.7, CH 4.06 ddd (12, 9.0 and 5.0) C-1D, C-4C H-1C, H-1D, H-5C, H-2Ceq 77.9 4.08 ddd (12, 9.0 and 5.0) C-1D, C-4C H-1C, H-5C, H-4C, H-2Ceq
4C 76.3, CH 3.46 t (9.0) C-3C, C-5C, C-6C H-2Cax, H3-6C 76.5 3.48 t (9.0) C-3C, C-6C H-2Cax, H-5C, H-6C
5C 73.5, CH 3.68 dq (9.0 and 6.0) C-4C, C-6C H-3C, H-1C, H3-6C 73.4 3.68 dq (9.0 and 6.0) C-4C, C-6C H-1C, H-3C, H-4C, H3-6C
6C 19.7, CH3 1.59 d (6.0) C-4C, C-5C H-5C, H-4C 19.4 1.57 d (6.0) C-4C, C-5C H-4C, H-5C
1D 100.4, CH 4.78 dd (9.6 and 2.0) C-3C H-3D, H-5D, H-2Deq, H-3C 94.9 5.22 dd (4.0 and 2.3) C-3C H-3D, H-2Ceq, H-2Deq, H-2Dax
2Dax 33.3, CH2 2.42 ddd (12, 12 and 9.6) C-1D, C-3D, C-4D H-1D 34.6 2.02 ddd (14.4, 4.0 and 3.0) C-1D, C-3D H-1D, H-3D, H-2Deq,
2Deq 2.18 ddd (12, 5.0 and 2.0) 2.35 ddd (14.4, 3.0 and 2.3) H-1D, H-3D, H-2Dax
3D 77.2, CH 4.22 ddd (12, 5.0 and 2.5) C-1E, C-4D H-1D, H-2Deq, H-5D, H-1E 75.2 4.39 ddd (3.0 3.0 and 3.0) C-1D, C-4D, C-5D, C-1E H-1D, H-2Dax, H-2Deq, H-1E
4D 70.2, CH 4.10 br d (2.5) C-3D, C-5D H3-6D 72.8 3.67 ddd (9.0 and 3.0) C-5D, C-6D H-5D, H3-6D
5D 74.6, CH 3.71 dq (6.0 and 2.5) C-4D, C-6D H-1D, H-3D, H3-6D 67.4 4.69 dq (9.0 and 6.2) C-4D, C-6D H-1D, H-4D, H3-6D
6D 19.4, CH3 1.54 d (6.0) C-4D, C-5D H-5D 18.9 1.54 d (6.2) C-4D, C-5D H-4D, H-5D
1E 97.8, CH 5.62 dd (9.6 and 2.0) C-3D H-5E, H-2Eax, H-2Eeq, H-3D 98.7 5.44 dd (9.6 and 2.0) C-3D H-2Eax, H-2Eeq, H-3D, H-5E
2Eax 40.3, CH2 2.00 ddd (12, 9.6 and 3.0) C-1E, C-3E, C-4E H-1E, H-2Eax 45.5 1.86 dd (13.0, and 9.0) C-1E, C-3E H-1E, H-4E,
2Eeq 2.45 ddd (12, 3.0 and 2.0) 2.41 dd (13.0 and 2.0) H-1E
3E 69.1, CH 4.45 ddd (3.0, 3.0, and 3.0) C-4E H-4E 71.4
3E-CH3 28.2 1.44 s C-3E, C-4E, C-2E H-4E
4E 72.4, CH 3.62 dd (9.2 and 3.0) C-3E, C-5E H-2Eax, H-3E, H3-6E 77.8 3.31 d (9.2) 3E-CH3, C-5E, C-6E H-2Eax, H3-3E, H-5E, H3-6E
5E 71.2, CH 4.42 dq (9.2 and 6.0) C-1E, C-4E, C-6E H3-6E, H-1E 72.2 4.22 dq (9.2 and 6.0) H-1E, H3-6E
6E 17.9, CH3 1.61 d (6.0) C-4E, C-5E H-5E 19.1 1.60 d (6.0) C-4E, C-5E H-4E, H-5E