Ree acetyl groups over the structure of 7. The H-6 and C-6 of glucose were downfield shifted to H four.14 (m), 4.31(m); C 63.27 (DMSO), H four.69 (dd, J = 3.7, 11.four Hz), four.88 (d, J = 11.four Hz) and C 63.61 (pyridine-d6) (Figures S38S42) compared with normal values of glucose [34]. This downfield shift supports C-6 acetylation. More evidence for C-6 acetylation was obtained from NOESY experiments exactly where NOE correlations have been CA Ⅱ web observed between the acetyl protons at H 2.00 (s) and H-5 at H 3.99 (m) (Figures S33 37). An H2BC experiment was applied to assign the rhamnose protons and carbons (Figures S31 and S32). The downfield shift of H-2″, H-3″, H-4″ to H five.91 (s), five.95 (d, J = 7.7 Hz) and 5.71 (t, J = 9.six Hz) (pyridine-d6) (Figures S38 and S39) pointed out their acylated nature. The position of the cinnamoyl moiety was decided by way of the evaluation of HMBC experiment correlations measured in pyridine d6 (Figures S44 and S45). Three bond contours had been clear among H-3″ at H five.95 along with the cinnamoyl carbonyl signal at C 165.89. Both H-2″, H-4″ at H 5.91, 5.71 showed 3 bond correlations with the two acetyl carbonyls at C 169.89 and 170.21 (Figures S44 and S45). Based on the above discussion, compound two was identified as 6-O–L (2″, 4″-diacetyl, 3″-O-trans-cinnamoyl) CBP/p300 Purity & Documentation rhamnopyranosyl-6 -acetyl catalpol and was offered the trivial name 6 -acetyl hypericifolioside B.Biology 2021, ten,5 ofTable 1. 1 H NMR data ( ppm, J in parentheses in Hz) for compounds 1 and 7 . Pos. 1 CD3 OD 1 three 4 5 six 7 9 10 1 2 three four 5 six 1″ 2″ 3″ 4″ 5″ 6″ 3 2 ,six 7 8 3″””” 2″”, 6″” 7″” 8″” 4.95 (d, 9.eight) 6.43 (d, five.8) 5.16 (t, five.4) two.54 (bq, 4.five) four.03 (d, 8.0) three.71 (s) 2.65 (t, 9.0) three.78 (d, 13.0) four.18 4.83 (d, 7.9) 3.32 (m) three.43 (m) 3.43 (m) three.52 (m) 4.28 (dd, five.0, 12.0) 4.47 (d, six.8) five.13 (s) 5.43 (bs) 5.53 (dd, 2.7,10.0) five.32 (t, ten.0) four.18 1.27 (d, six.0) 7.35 7.49 (d, six.6) 7.61 (d, 16.0) six.40 (d, 16.0) 7.35 7.53 (d, six.6) 7.70 (d, 16.0) 6.50 (d, 16.0) DMSO d6 4.83 (d, 9.two) six.44 (d, 1.five) five.04 2.39 (bs) three.93 3.69 (s) 2.46 (bt, eight.0) three.63 (d, 12.4) three.93 four.66 (d, 7.0) 3.11 (bt, 7.5) three.25 (bt, eight.4) 3.19 (bt, eight.9) 3.42 (m) 4.14 (m) four.31 (m) 5.14 (s) five.27 (bs) 5.27 (bs) five.04 3.93 1.16 (d, four.three) 7.43 (bs), 7.69 (bs) 7.60 (d, 16.0) six.54 (d, 16.0) 2 Pyridine d6 five.45 6.47 (d, five.2) 5.45 2.76 (bs) 4.25 three.93 (s) 2.85 (t, 7.7) 4.39 (d, 13.0) 4.50 (d, 13.0) 5.45 (Overl.) four.ten (m) 4.25 4.ten (m) 3.99 (m) 4.69 (dd, three.7, 11.4) 4.88 (d, 11.four) five.45 five.91(s) five.95 (d, 7.7) five.71 (t, 9.six) four.34 (m) 1.38(d, 5.five) 7.30 (bs), 7.47 (d, five.8) 7.91 (d, 16.0) six.74 (d, 16.0) CD3 OD five.14 six.43 (bd, 5.five) 5.14 2.55 (bq, 4.three) 4.11 (d, 8.0) three.72 (s) 2.64 (t, 9.4) three.87 (d, 13.two) four.16 (m) four.83 (d, 7.9) 3.32 (m) 3.46 (t, 9.0) three.32 (m) 3.37 (m) three.67 (dd, 6.five, 11.9) three.96 (d, 10.9) five.14 five.43 (bs) five.55 (dd, 3.2, ten.2) 5.33 (t, ten.0) 4.16 1.28 (d, six.2) 7.34 7.47 (d, 6.4) 7.60 (d, 16.0) six.39 (d, 16.0) 7.34 7.51 (d, six.1) 7.71 (d, 16.0) 6.49 (d, 16.0) three Pyridine d6 5.51 (d, eight.8) 6.48 (d, five.7) five.19 (t, five.0) 2.76 (bq, 3.9) 4.12 3.80 (s) 2.84 (t, 8.9) four.48 5.51 (d, eight.8) four.12 4.30 4.19 (bt, 9.2) 4.01 (bt, six.7) 4.30 four.53 (d, 11.8) 5.43 (s) 5.94 six.09 (dd, 2.6, 10.0) five.89 4.44 (m) 1.46(d, 6.0) 7.31 (bs) 7.24 (d, 7.3) 7.89 (d, 16.0) six.72 (d, 16.0) 7.57(bs) 7.39 (d, 7.2) 7.99 (d, 16.0) six.80 (d, 16.0) CD3 OD five.11 6.42 (bd, six.0) 5.11 two.51 (bq, 4.six) 4.09 (d, 8.4) three.70 (s) 2.62 (bt, 9.three) 3.85 (d, 13.two) four.18 (d, 13.two) 4.80 (d, 7.9) 3.28 (m) 3.44 (bt,9.0) three.28 (m) three.33 (m) 3.65 (dd, 6.8, 12.0) three.94 (bd, 12.0) five.11 5.39 (m) five.41.
