molecular formula C22 H28 O5 . By comparing the NMR information of 12 with those of 10, it was discovered that the NMR information of 12 have been identical to those of 10 except for the added Caspase 8 Inhibitor Compound ethoxyl proton signals at H three.56 (2H, q, J = 7.0 Hz) and 1.29 (3H, t, J = 7.0 Hz) (Table 2). It was suggested that the methoxyl group belonging for the 3-methoxy-3-methylbutyl substituent in ten was replaced by an ethoxyl group in 12. This deduction was constant using the difference in molecular ion masses [m/z = 14.0155 mmu (CH2 )]. HMBC correlations in between the protons at H 3.56 (H-1 ) and 1.29 (H-2 ) and also the carbon at c 76.3 (C-3 ) confirmed the attachment of the ethoxyl group at C-3 (Figure 3). For that reason, compound 12 was assigned 4,2 ,4 -trihydroxy-3 -(3-O-ethyl-3-methylbutyl)dihydrochalcone. Compound 13 was obtained as a pale yellow amorphous powder. The HRESIMS of 13 displayed an [M + Na]+ peak at m/z 349.1416 which was consistent using the molecular formula C20 H22 O4 , indicating 10 indices of GSK-3β Inhibitor custom synthesis hydrogen deficiency. UV spectrum showed absorption maxima at 220 and 286 nm. Comparison of its NMR spectroscopic information withInt. J. Mol. Sci. 2021, 22,6 ofthose of ten indicated that 13 possess a comparable structure but with a two,2-dimethyldihydropyran ring within the case of 13 (Table 2). On the basis on the HMBC correlation from H-5 to C-3 together using the presence of the intramolecular H-bonded hydroxyl proton signal at H 13.17 (2 -OH), it was confirmed that the further two,2-dimethyldihydropyran ring was fused to ring A by means of C-3 and C-4 positions. Compound 13 was for that reason characterized as four,two -dihydroxy-(two,2-dimethyl-3,4-dihydropyran)-(5″,6″:3 ,four )dihydrochalcone. Compound 14, isolated as a pale yellow amorphous powder, showed a sodium adduct molecular ion peak at m/z 349.1415 in the HRESIMS corresponding to the molecular formula C20 H22 O4 , which was the same as that of 13. The general NMR data of 14 showed analogous structural options to these of 13 except for the absence of an H-bonded hydroxyl proton resonance inside the decrease field (Table three). These data suggested that the 2,2dimethyldihydropyran ring was fused to C-2 and C-3 positions of 14. Supportive proof for this deduction was offered by the up-field shifted carbon resonance at C 155.2 (C-2 ) right after combined analysis of its HSQC and HMBC information. Additionally, the NMR information of six were in great accordance with those of deoxydihydroxanthoangelol H in which a methoxyl group was attached at C-4 as an alternative of a hydroxyl group in six [20]. Hence, the structure of 14 was assigned four,four -dihydroxy-(2,2-dimethyl-3,4-dihydropyran)-(5″,6″:3 ,2 )dihydrochalcone.Table three. 1 H- and 13 C-NMR data for 147 and 19 in DMSO-d6 . No. C/H C=O 1 2,6 three,five 4 1 two 3 4 five six 6.40 d (eight.six) 7.38 d (8.six) two.55 t (six.7) 1.76 t (six.7) 1.29 s 1.29 s 7.00 d (8.1) 6.66 d (eight.1) H (J/Hz) 3.12 t (7.3) two.75 t (7.3)a14 Cb15 H (J/Hz) three.23 t (7.7) 2.82 t (7.7)a16 Cb17 Cb19 CbH (J/Hz) 3.23 t (7.1) two.82 t (7.1)aH (J/Hz) 7.72 s 7.72 saH (J/Hz) three.17 t (7.7) two.81 t (7.7)aCb44.9 29.5 198.six 131.7 128.9 115.0 155.three 118.2 155.two 108.1 161.2 107.0 129.39.5 29.2 204.6 130.39.0 29.1 204.6 130.117.five 143.6 191.1 125.38.9 29.3 203.8 131.7.06 d (eight.0) 6.67 d (eight.0)129.2 115.1 155.six 113.7 159.4 113.7.06 d (8.3) 6.67 d (eight.three)129.1 115.0 155.five 112.0 162.1 107.7.74 d (eight.0) six.84 d (eight.0)131.1 125.7 160.four 112.0 163.eight 115.7.06 d (8.2) 6.67 d (eight.two)129.two 115.0 155.five 111.4 162.three 115.12.80 s (OH) 6.41 d (8.7) 7.81 d (eight.7) three.04 d (8.eight) four.71 t (8.8) 1.13 s 1.12 s166.eight 101.7 132.1″17.26.2″ 3″ 4″ 5″31.1 74.7 26.five 26.9