The protons H-1 and H-6; H-6 and H-7; H-6 firmed in the NOE correlations amongst the protons H-1 and H-6; H-6 and H-7; H-6 and H-10, all with -orientation (Figures S17 20). The chemical shift of C-6 at 83.74 and H-10, all with -orientation (Figures S17 20). The chemical shift of C-6 at C 83.74 C was diagnostic to get a substituted position. The six CLK medchemexpress carbon resonances at 96.41, 71.05, was diagnostic for any substituted position. The six carbon resonances at C 96.41, 71.05, C 69.92, 69.45, 66.89 in addition to the CECR2 Accession methyl carbon at 16.53 correlated by the HSQC 69.92, 69.45, 66.89 as well as the methyl carbon1 at C 16.53 correlated by the HSQC C experiment with all the proton doublets at C 1.27 in 1 H NMR spectra had been assigned to a experiment with the proton doublets at C 1.27 in H NMR spectra have been assigned to a rhamnosyl substituent (Figure S9). HMBC correlations between the H-6 doublet at H rhamnosyl substituent (Figure S9). HMBC correlations in between the H-6 doublet at H four.03 4.03 and C-1 of rhamnose at C 96.41C too as the NOE correlation among H-6 and and C-1″ of rhamnose at help C as position of a rhamnosy moeity at C-6. H-6 and H-1″ H-1 singlet at H five.13 all C 96.41 the effectively because the NOE correlation involving Quite a few iridoid singlet at H 5.13 all help the position of a rhamnosy moeity were previously reported glycosides such as 7 and 8 bearing a rhamnose moiety at C-6 at C-6. Several iridoid glycosides such as [292]. Compared rhamnose moiety at bearswere previously reported (Figures S10 14) 7 and eight bearing a with compound 7, 1 C-6 an additional two acetyls (Figures trans-cinnamoyl (Tables 1 and with compound 7, 1 bears an extra two acetyls and 1 S10 14) [292]. Compared two). The H-6 and C-6 in the glucose moiety in 1 were and 1 trans-cinnamoyl (Tables 1 = five, 12 Hz), 4.47(d, J = C-6′ in the glucose moiety in 1 downfield shifted to H 4.28 (dd, J and 2). The H-6′ and six.eight Hz) and C 62.74 compared have been standard values of glucose4.28 (dd, J = 5, 12 Hz), four.47(d, J =position.and Ccorrelations with downfield shifted to H [33], indicating acylation at that six.eight Hz) NOE 62.74 comparedobserved in between the acetyl protonsindicating acylation at that position. NOE5, 12 had been with typical values of glucose [33], at H two.07 (s) and H-6 at H four.28 (dd, J = correlations have been observedH-5 at Hthe acetyland H-4 at H two.07 (s) and H-6′ at H 4.28 (dd, J Hz), four.47(d, J = 6.8 Hz), amongst three.52 (m) protons at 3.43 (m) (Figures S17 20). Additional = five, 12 Hz), 4.47(d, J = 6.eight Hz), H-5′ at H 3.52 (m) and H-4’correlations (Figures S17 20). proof for C-6 acetylation was obtained from the HMBC at 3.43 (m) among both H-6 Additional proof methyl protons at H two.07 with all the acetyl carbonyl correlations amongst protons, and also the for C-6′ acetylation was obtained in the HMBC at C 171.40 (Figures each H-6′ protons, andexperiment protons at H two.07used to assign protons and C 171.40 S10 14). The H2BC the methyl was extensively with the acetyl carbonyl at carbons, (Figures S10 14). The H2BC experiment was extensively used to assign protons shifts of specifically those in the rhamnose moiety (Figures S15 and S16). The chemical and carbons, particularly thoseH 5.43 (bs), 5.53 (dd, J = two.7, 10 Hz) and 5.32 (t, JThe chemical shifts H-2″, H-3″, H-4″ at from the rhamnose moiety (Figures S15 and S16). = 10 Hz) indicated of H-2”, 3 positions H five.43 (bs), 5.53 (dd, J = 2.7, 10 Hz) the two cinnamoyl as well as the left that the H-3”, H-4” at are acylated. The assignments of and five.32.
