Iridoids and sesquiterpenoids from Valeriana jatamansi and their anti-influenza virus activities

Valeridoids G – Q, Eleven seco‐Iridoids from Valeriana jatamansi and Their Bioactivites

“…Compound 2 was obtained as yellow oil, and its molecular formula C 18 H 24 O 7 was deduced from a pseudomolecular ion peak at m/z 375.1421 [M + Na] + in the positive HR-ESI-MS, indicating 14 mass units more than compound 7. Comparison of the NMR spectroscopic data of 2 with those of 7 suggested that they were quite similar to each other, except for the replacement of the isovaleroxy group (OIv) in 7 by a (R)-3-methylvaleroxy group [19] (OMv) [δ C 173.1 (s, C-1'), 41.6 (t, C-2'), 32.7 (d, C-3'), 29.7 (t, C-4'), 11.6 (q, C-5') and 19.5 (q, C-6')] [15] in 2. A series of HMBCs (Figure 2 3b) assigned the absolute configuration of 2 to be 1S, 8S and 9S.…”

“…Compound 11 was isolated as a yellow oil, whose molecular formula was determined to be C 15 -11). The above NMR data were extremely comparable to those of jatamanin J, [3] except for the presence of the isovaleryloxy group.…”

“…Compound 2 was obtained as yellow oil, and its molecular formula C 18 H 24 O 7 was deduced from a pseudomolecular ion peak at m/z 375.1421 [M+Na] + in the positive HR‐ESI‐MS, indicating 14 mass units more than compound 7 . Comparison of the NMR spectroscopic data of 2 with those of 7 suggested that they were quite similar to each other, except for the replacement of the isovaleroxy group (OIv) in 7 by a ( R )‐3‐methylvaleroxy group [19] (OMv) [ δ C 173.1 (s, C‐1′), 41.6 (t, C‐2′), 32.7 (d, C‐3′), 29.7 (t, C‐4′), 11.6 (q, C‐5′) and 19.5 (q, C‐6′)] [15] in 2 . A series of HMBCs ( Figure 2) from H 2 ‐2′ [ δ H 2.37 (dd, J =15.1, 6.0) and 2.17 (dd, J =15.1, 8.1)] to C‐1′, C‐3′ and C‐6′, and from H 2 ‐4′ [ δ H 1.41–1.35 (m) and 1.27–1.21 (m)], Me‐5′ [ δ H 0.89 (t, J =7.4, 3H)] and Me‐6′ [ δ H 0.94 (d, J =6.5, 3H)] to C‐3′, together with the spin systems of H 2 ‐2′/H‐3′/Me‐6′ and H 2 ‐2′/H‐3′/H 2 ‐4′/Me‐5′ in the 1 H‐ 1 H COSY spectrum ( Figure 2), supported the existence of the OMv moiety.…”

“…Appropriate conformers of model compounds were generated by Spartan 14 using the MMFF94 molecular mechanics force field calculation [15,25,26] . The selected conformers of the calculated compounds were further optimized by the density functional theory method at the APFD/6‐31G (d) level (compounds 1 , 2 , 5 , 8 , 9 , 10 and 12 ) or B3LYP/6‐31G (d) level (compound 11 ).…”

“…Appropriate conformers of model compounds were generated by Spartan 14 using the MMFF94 molecular mechanics force field calculation. [15,25,26] The selected conformers of the calculated compounds were further optimized by the density functional theory method at the APFD/6-31G (d) level (compounds 1, 2, 5, 8, 9, 10 and 12) or B3LYP/6-31G (d) level (compound 11). The ECD calculations of compounds were carried out using TD-DFT-APFD/6-31G (d) (compounds 1, 2, 5, 8, 9, 10 and 12) or TD-DFT-B3LYP/6-311 + G (2d, p) (compound 11) with the IEFPCM solvent model in MeOH based on the optimized geometries.…”