Jatavaleridoids A-H, eight new iridoids from the roots and rhizomes of Valeriana jatamansi Jones

New Iridoids and Acyclic Monoterpenoids from the Roots and Rhizomes of Valeriana officinalis var. latifolia

“…Generally, naturally occurring iridoids display α-orientation for H-1 and β-orientation for H-5 and H-9. [22,26,28,30] The NOE crosspeaks of H-9/H 2 -10 in the ROESY spectrum (Figure SI) indicated that 8-OH was α-oriented. The coupling constant of H-6 and H-7 (J 6, 7 = 2.6 Hz) in 5 was similar to those in jatamanvaltrates T and U (J = 2.7 Hz), [30] as well as iridoidvols A-D (J = 2.8 Hz), [3] suggested that H-7 in compound 5 was also α-oriented.…”

“…This deduction was further supported by the HMBC correlations (Figure 2) from H 2 ‐1 ( δ H 4.45 and 3.92), H‐4 ( δ H 2.54) and Me‐11 ( δ H 1.26) to C‐5, together with the spin‐coupling system of H 2 ‐6/H 2 ‐7/H‐8/H‐9/H 2 ‐1 in the 1 H− 1 H COSY spectrum (Figure 2). Naturally occurring iridoids occupied β ‐orientation for 5‐OH and H‐9 [22,26,28,29] . In the ROESY spectrum of 4 (Figure 3), the NOE correlations of H‐9/Me‐10 and H‐9/Me‐11 indicated that both Me‐10 and Me‐11 were in β ‐orientation.…”

“…Naturally occurring iridoids occupied β-orientation for 5-OH and H-9. [22,26,28,29] In the ROESY spectrum of 4 (Figure 3), the NOE correlations of H-9/ Me-10 and H-9/Me-11 indicated that both Me-10 and Me-11 were in β-orientation. Finally, the comparison of the experimental and calculated ECD spectra of 4 (Figure 4b) allowed the determination of the absolute configuration of compound 4 to be 4R, 5R, 8S and 9S.…”

“…Furthermore, two isovaleroxyl groups were attached to C‐1 and C‐7, respectively, based on the HMBC correlations of H‐1/C‐1′ and H‐7/C‐1′′′. Generally, naturally occurring iridoids display α ‐orientation for H‐1 and β ‐orientation for H‐5 and H‐9 [22,26,28,30] . The NOE cross‐peaks of H‐9/H 2 ‐10 in the ROESY spectrum (Figure SI) indicated that 8‐OH was α ‐oriented.…”

“…[12,16] In recent years, a number of iridoids and sesquiterpenoids from the genus Valeriana have been reported by our group, and some of them showed cytotoxicity, anti-inflammatory and anti-influenza virus activities. [3,6,[19][20][21][22][23] In our continuing search for structurally novel and bioactive constituents from Valeriana species, seven iridoids including five new ones (valeralides A-E), as well as two new acyclic monoterpenoids (valeralides F and G) (Figure 1), were isolated from the roots and rhizomes of Valeriana officinalis var. latifolia.…”