Table 1 A in Polyketide-derived macrobrevins from marine macroalga-associated Bacillus amyloliquefaciens as promising antibacterial agents against pathogens causing nosocomial infections

Table 1A NMR spectroscopic data of macrobrevin analogues, 1–2.
No.13C1H (mult., int., J in Hz) aCOSYHMBCNo.13C1H (mult., int., J in Hz) aCOSYHMBC1166.2–––1166.2–––2122.96.05 (d, 1H, 13.8)H-3C-1, 42122.45.82 (d, 1H, 13.1)H-3C-1, 43148.47.09 (d, 1H, 12.1)–C-13155.26.89 (dd, 1H, 12.1, 4.1)H-4C-1481.2–––437.52.65 (m, 1H, 2.1)H-5, H-35–579.83.35 (t, 1H β, 3.8)H-6C-3, 4, 7579.63.40 (m, 1H β)H-6C-3, 7631.01.65 (m, 2H)H-7–629.01.64 (m, 2H)H-7–728.41.49 (m, 2H)H-8–717.51.48 (m, 2H)H-8–837.51.67 (m, 2H)H-9C-6836.81.65 (m, 2H)H-9C-6973.13.15 (q, 1H α, 2.7)H-10C-7, 10975.44.32 (t, 1H α, 2.7)–C-7, 101019.01.78 (m, 1H β)H-11, H-36C-810138.6–––1128.51.38 (m, 2H)H-12–11127.65.19 (t, 1H, 10.5)H-12–1232.41.44 (m, 2H)H-13–1240.52.07 (t, 2H, 1.2)H-13–1345.22.15 (m, 1H α)H-14, H-37C-11, 37a1342.62.15 (m, 1H α)H-14, H-37C-11, 3714130.35.48 (dd, 1H, 13.1, 2.4)––14129.25.46 (dd, 1H, 13.0, 2.1)–15131.65.52 (dt, 1H, 12.5, 2.1)H-16C-1715130.45.68 (dt, 1H, 12.1, 2.5)H-16C-171630.42.07 (m, 2H)H-17–1628.12.04 (m, 2H)H-17C-141731.81.50 (m, 2H)H-18–1731.51.50 (m, 1H)H-18–1836.81.72 (m, 1H α)H-19, H-38C-201838.51.78 (m, 1H α)H-19, H-38C-201970.93.44 (q, 1H α, 3.1)H-20C-17, 211971.33.60 (q, 1H α, 2.2)H-20C-17, 212037.91.53 (t, 2H, 3.5)H-21C-212037.81.52 (t, 2H, 3.5)H-21C-212170.23.92 (q, 1H β, 4.8)H-22C-12170.93.91 (m, 1H β)H-22C-12234.92.21 (m, 1H α)H-23, H-39C-21, 242233.12.40 (m, 1H α)H-23, H-39C-21, 242338.61.27 (t, 2H, 3.0)H-24C-212338.61.27 (t, 2H, 2.5)H-24C-212435.61.69 (m, 1H β)H-25, H-40C-262435.31.68 (m, 1H β)H-25, H-40C-262531.71.23 (m, 2H)H-26C-232530.21.25 (m, 2H)H-26C-232634.51.46 (m, 2H)H-27–2634.11.46 (m, 2H)H-27–2771.73.57 (q, 1H, 3.9)H-28C-28, 4127129.96.00 (t, 1H, 13.9)–C-28, 412847.82.42 (m, 1H β)H-29, H-41C-3028133.7–––29133.35.32 (t, 1H, 13.0)–C-2729135.86.47 (d, 1H, 13.1)H-30C-2730135.45.41 (t, 1H, 10.2)H-31C-31, 3230129.35.39 (t, 1H, 10.2)H-31C-31, 323174.23.97 (t, 1H β, 4.1)H-32–3176.23.96 (t, 1H β, 3.2)H-32–3245.51.83 (m, 1H β)H-33, H-42C-343242.11.81 (m, 1H β)H-33, H-42C-343323.31.55 (m, 2H)H-34C-313324.71.54 (m, 2H)H-34C-313411.50.97 (t, 3H, 1.8)––3411.30.96 (t, 3H, 1.7)––3524.71.33 (s, 3H β)–C-43524.51.33 (d, 3H β, 2.4)–C-43615.91.02 (d, 3H α, 2.8)–C-103613.30.98 (s, 3H α)–C-103728.11.41 (m, 2H)H-37aC-143723.31.02 (d, 3H β, 2.1)–C-1437a12.10.93 (t, 3H, 2.1)–C-373816.00.97 (d, 3H β, 2.2)–C-183816.10.99 (d, 3H β, 3.0)–C-183913.80.94 (d, 3H β, 1.6)–C-22, 233953.43.63 (d, 2H, 1.6)–C-22, 234022.70.92 (d, 3H α, 2.1)–C-244021.20.95 (d, 3H α, 2.5)–C-244112.11.01 (s, 3H α)–C-284113.01.03 (d, 3H α, 2.8)–C-284215.20.83 (d, 3H α, 3.4)–C-324214.10.88 (d, 3H α, 3.4)–C-32–––––1166.3–––1166.3–––2122.55.87 (d, 1H, 12.8)H-3C-1, 42122.45.85 (d, 1H, 12.9)H-3C-1, 43155.76.84 (dd, 1H, 12.6, 4.5)H-4C-1, 53155.96.84 (dd, 1H, 12.1, 4.3)H-4C-1436.72.36 (m, 1H, 2.1)H-5, H-35–436.82.64 (m, 1H, 2.3)H-5, H-35–579.03.34 (m, 1H β)H-6C-7581.82.84 (m, 1H β)H-6C-3, 7, 5a631.31.62 (m, 2H)H-7–5a57.43.48 (s, 3H)–C-5719.21.49 (m, 2H)H-8–628.31.65 (m, 2H)H-7–836.81.65 (m, 2H)H-9C-10719.11.47 (m, 2H)H-8–975.34.37 (t, 1H α, 2.1)–C-7, 10, 36837.31.77 (m, 2H)H-9C-610138.4–––975.14.31 (t, 1H α, 2.1)–C-1011127.55.27 (t, 1H, 10.4)H-12–10138.4–––1240.22.04 (t, 2H, 1.2)H-13–11127.55.18 (t, 1H, 10.4)H-12–1345.52.13 (m, 1H α)H-14, H-37C-11, 371240.42.07 (t, 2H, 1.1)H-13–14129.25.44 (dd, 1H, 13.4, 2.7)––1342.62.14 (m, 1H α)H-14, H-37C-11, 3715129.95.55 (dt, 1H, 12.7, 2.5)H-16C-1714130.35.45 (dd, 1H, 12.4, 2.3)––1629.72.01 (m, 2H)H-17C-1415130.05.52 (dt, 1H, 12.3, 2.5)H-16C-171731.51.53 (m, 1H)H-18–1628.12.03 (m, 2H)H-17C-141837.41.71 (m, 1H α)H-19, H-38C-201728.51.51 (m, 1H)H-18–1971.63.39 (q, 1H α, 2.6)H-20C-171837.71.90 (m, 1H α)H-19, H-38C-202038.61.56 (t, 2H, 3.5)H-21C-211971.03.39 (q, 1H α, 2.4)H-20C-172170.53.92 (m, 1H β)H-22C-12038.61.53 (t, 2H, 3.3)H-21–2234.12.22 (m, 1H α)H-23, H-39–2168.33.90 (m, 1H β)H-22C-12337.81.29 (t, 2H, 2.4)H-24C-212233.12.37 (m, 1H α)H-23, H-39C-21, 242435.31.69 (m, 1H β)H-25, H-40C-262338.51.26 (t, 2H, 2.2)H-24C-212531.91.21 (m, 2H)H-26C-232436.01.81 (m, 1H β)H-25, H-40–2633.11.43 (m, 2H)H-27–2529.71.24 (m, 2H)H-26C-2327131.85.58 (t, 1H, 13.9)–C-28, 412635.31.42 (m, 2H)H-27–28143.8––27135.95.61 (dt, 1H, 13.1, 4.1)H-28–29130.36.26 (d, 1H, 13.1)H-30C-2728129.26.05 (dd, 1H, 13.4, 3.5)H-29C-3030135.85.61 (t, 1H, 10.2)H-31C-31, 3229128.76.46 (dd, 1H, 13.0, 3.2)H-30C-273175.54.65 (t, 1H β, 3.2)H-32C-31a30135.85.70 (dd, 1H, 11.2, 3.6)H-31C-3231a170.3–––3175.73.57 (t, 1H, 3.3)H-32–31b22.72.06 (s, 3H)–C-31, 31a3245.51.93 (m, 1H β)H-33, H-41–3245.22.26 (m, 1H β)H-33, H-42C-343324.61.37 (m, 2H)H-34C-313324.71.59 (m, 2H)H-34C-313412.10.96 (t, 3H, 2.5)–C-323411.30.94 (t, 3H, 1.5)––3523.21.34 (d, 3H β)–C-43523.21.35 (d, 3H β)–C-43615.80.97 (s, 3H α)–C-103615.90.97 (s, 3H α)–C-103722.71.01 (s, 3H β, 2.3)–C-143722.51.02 (d, 3H β, 2.2)–C-143816.61.00 (d, 3H β, 2.3)–C-183817.50.99 (d, 3H β, 2.6)–C-183915.30.93 (d, 3H β, 1.4)–C-22, 233912.00.91 (d, 3H β, 1.4)–C-22, 234021.30.92 (d, 3H α, 1.4)–C-244021.20.89 (d, 3H α, 1.6)–C-244116.10.91 (d, 3H α, 2.1)–C-324168.54.21 (s, 2H)–C-28–––––4216.10.83 (d, 3H α, 2.2)–C-32–––––
Nuclear magnetic resonance (NMR) assignments were made by means of correlation spectroscopy (1 H– 1 H COSY), nuclear Overhauser effect spectroscopy (NOESY), heteronuclear multiple-bond correlation spectroscopy (HMBC), and heteronuclear single-quantum correlation spectroscopy (HSQC) experiments.
NOESY relations have been represented by double-sided arrows, wherein the red and blue colored arrows indicated alpha and beta protons, respectively.
a NMR spectra were recorded using Bruker AVANCE III 500 MHz (AV 500) spectrometer in CDCl as aprotic solvent at ambient temperature with TMS as the internal 3 standard (δ 0 ppm). Values in parts per million (ppm), multiplicity and coupling constants (J = Hz) are indicated in parentheses.