14 was the identical as compound V, which was the item from the alkaline hydrolysis of parasiticolide A [27]. Even so, the absolute configuration of compound V was ambiguous. The relative configuration of 14 was also defined by the NOESY correlation. The correlations of H3 -14 with H1 -5 and H1 -6, and H2 -13 with H2 -15 have been located within the NOESY spectrum, which signifies H1 -5, H1 -6, and H3 -4 have been on the identical side, and H2 -13 and H2 -15 have been on the opposite face (Figure 3). Thus, the absolute configuration of the stereogenic centers in 14 was assigned as 4R, 5R, 6S, 10S by comparing its experimental ECD spectrum with that in the calculated model molecule (Figure four). Lastly, compound 14 was named as astellolide J. Astellolide Q (15) was also acquired as a yellow powder. It molecular formula was determined as C17 H24 O6 based on HRESIMS evaluation at m/z 347.14578 [M+Na]+ (calcd. 347.14651), indicating six degrees of unsaturation. The 1 H NMR of 15 showed two methyls (H 1.15 and 2.08), four methylenes (H 1.16, 1.45, 1.54, 1.78, 1.91, two.05, 2.34 and 2.50), a single methines (H 1.74) a single hydroxymethine (H 4.55) and 3 hydroxy-methylenes (H 3.34, 3.92, four.09, 4.33, four.84 and five.04). Also, as outlined by the HSQC data, the 13 C NMR data showed the presence of 17 carbon signals, like two ester carbonyl carbons (C 173.1, 177.0) and two olefinic carbons (C 124.0, 169.0), one particular methyl, seven methylenes (three oxygenated), two methines (one oxygenated), two aliphatic quaternary carbons (Table 2).SFRP2, Human (HEK293, His) Analysis of its 1 H NMR and 13 C NMR information in association together with the 2D NMR information established a nucleus of drimane sesquiterpenoid characterized by an astellolide scaffold, structurally similar towards the co-isolated compound 14 (Figures S26 and S27). It might be clearly observedMar. Drugs 2022, 20,six ofthat compound 15 has an further acetyl fragment. In addition, the HMBC from H2 -13 to Ac-OCO indicated that the acetyl fragment was linked to C-13 (Figure 3).Table two. 1 H NMR (400 MHz) and 13 C NMR (one hundred MHz) of 15 in CD3 OD. Position 1 two three four five 6 7 8 9 C 35.three (CH2 ) 19.five (CH2 ) 37.0 (CH2 ) 39.three (C) 56.4 (CH) 63.six (CH) 33.0 (CH2 ) 124.0 (C) 169.0 (C) 1.74, s 4.61, d (11.0) two.34, d, (18.9) two.50, d (18.3) H (J in Hz) 1.45, m 2.05, m 1.54, m 1.78, m 1.16, m 1.91, m Position 10 11 12 13 14 15 Ac-CH3 Ac-OCO C 44.MMP-1 Protein Source 2 (C) 71.PMID:24101108 eight (CH2 ) 177.0 (C) 68.1 (CH2 ) 28.1 (CH3 ) 65.7 (CH2 ) 20.eight (CH3 ) 173.1 (C) 4.44, d (11.two) four.62, d (5.four) 1.16, s three.76, d (12.0) 4.33, d (11.9) 2.08, s 5.00, d (17.7) 4.84, d (17.6) H (J in Hz)Lastly, the NOESY correlation and experimental ECD spectrum of compound 15 had been identical to those of 14 (Figures three and 4). Hence, the absolute configuration of 15 was also assigned as 4R, 5R, 6S, 10S. two.2. Antimicrobial Assay Compounds 15 were investigated for their antimicrobial activities against two phytopathogenic fungi and four bacterial strains. As shown in Table 3, andrastin-type meroterpenoids have superior antimicrobial activities against phytopathogenic fungus than against bacteria. Most of all the tested compounds (9 compounds out of total 15 compounds) displayed potent antimicrobial activities (MIC 50 /mL). Among them, compounds 1, 5 and ten exhibited outstanding antimicrobial activities against Penicillium italicum and Colletrichum gloeosporioides with MIC values of six.25, 1.56, six.25 and six.25, three.13, 6.25 /mL. Moreover, compound 1 showed inhibitory activities against Bacillus subtilis under concentration of six.25 /mL. Compound ten also displayed significan.
