) as well as the two oxygen-bearing carbons at C 79.2 and 72.five indicating the dihydroxylation took location at the olefinic double bond in the prenyl group. Around the basis of these evidences, structure of compound six was elucidated as 5,7,3 ,four -tetrahydroxy5 -(two,3-dihydroxy-3-methylbutyl)isoflavone.Int. J. Mol. Sci. 2021, 22,3 ofTable 1. 1 H- and 13 C-NMR data for 5 in CD3 OD.No. C/H 2 three 4 five six 7 8 9 10 1 two three four five six 1″ 2″ 3″ 4″ 5″ H a (J/Hz) four.65 t (eight.3) four.53 dd (10.0, 5.4) four.23 dd (ten.0, five.four) 5 Cb6 H a (J/Hz) 8.04 s Cb7 Ha(J/Hz)Cb70.5 46.9 197.9 156.0 95.four 157.0 125.three 149.two 102.0 115.7 150.7 110.9 153.3 108.five 129.three 116.six 129.1 75.1 26.5 26.153.five 127.two 180.9 162.four 98.7 164.6 93.four 158.3 104.9 123.6 122.three 143.9 145.1 122.0 114.2 32.eight 79.2 72.five 24.3 23.eight.03 s153.six 123.three 180.eight 162.four 98.8 164.five 93.5 158.3 104.9 122.7 120.8 141.2 145.three 120.six 113.8 30.7 69.2 77.4 24.four 19.a5.99 s6.22 d (two.1) 6.34 d (2.1)six.22 d (2.0) 6.33 d (2.0)6.81 d (two.1)6.75 d (2.1)6.34 d (8.three) six.91 d (eight.3) six.69 d (ten.0) five.68 d (10.0) 1.40 s 1.40 s6.92 d (2.1) two.97 dd (14.0, 1.9) 2.68 dd (14.0, ten.two) 3.65 dd (ten.two, 1.9) 1.25 s 1.25 s6.86 s 3.03 dd (16.7, five.four) 2.74 dd (16.7, 7.3) three.79 m 1.39 s 1.31 sAssignments were accomplished depending on HSQC and HMBC. J values (Hz) are given in parentheses. b 100 MHz.400 MHzpound 7 was obtained as a yellow amorphous powder. The HRESIMS spectrum of 7 exhibited an [M + Na]+ peak at m/z 393.0951 (calcd for C20 H18 O7 Na, 393.0950), which recommended a molecular formula of C20 H18 O7 corresponding to an epoxidized metabolite of 2. It showed 1 H- and 13 C-NMR spectral functions closely related to these of six. Compared using the NMR spectral information of compound 2, compound 7 exhibited the absence of olefinic proton signals belonging for the prenyl group. Meanwhile, presence of 1 oxygen-bearing methine H2 Receptor Agonist Compound carbon signal at c 69.two corresponding using the proton signal at H 3.79 and 1 oxygen-bearing quaternary carbon signal at c 77.4 had been observed depending on the HSQC and HMBC correlations. These benefits suggested that the olefinic double bond in the prenyl group was epoxidized. Therefore, the structure of 7 was elucidated as five,7,3 ,four -tetrahydroxy-5 (2-epoxy-3-methylbutyl)isoflavone. 2.two. CDK7 Inhibitor Source Biotransformation of Two Chalcones, Echinatin (3) and Isobavachalcone (4) having a. niger KCCM 60332 Biotransformation of echinatin (three) furnished two recognized metabolites 8 and 9. Biotransformation of isobavachalcone (4) afforded twelve metabolites 101, of which 107 and 19 were determined to be structurally new (Figure 2). Compounds eight and 9 were obtained as a pale yellow amorphous powder and a yellow amorphous powder, respectively. Their structures had been elucidated as (E)-1-(three,4dihydroxyphenyl)-3-(4-hydroxy-2-methoxyphenyl)-prop-2-en-1-one (eight) and loureirin C (9) by comparing their 1 H-NMR data (Figures S26 and S27) with those in the literatures [17,18].two.2. Biotransformation of Two Chalcones, Echinatin (3) and Isobavachalcone (four) having a. niger KCCMInt. J. Mol. Sci. 2021, 22,Biotransformation of echinatin (3) furnished two known metabolites 8 and 9. Bio-4 of 16 transformation of isobavachalcone (4) afforded twelve metabolites 101, of which 107 and 19 were determined to be structurally new (Figure 2).Figure 2. Compounds 81 Compounds 81 obtained by biotransformation of 3 and four using a. niger. Figure 2. obtained by biotransformation of three and four having a. nigerpounds eight and 9 had been acquired as aapale yellow amorphous powder and Its molecular Compound ten was obtained as pale yellow amorphous powder. a yellow formula o
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