Isoflavone Dimers and Other Bioactive Constituents from the Figs of Ficus mucuso

Abstract

Phytochemical investigation of the figs of Ficus mucuso led to the isolation of three new isoflavone dimer derivatives, mucusisoflavones A-C (1-3), together with 16 known compounds. Some of the isolates were tested in vitro for their inhibitory properties toward β-glucuronidase and Plasmodium falciparum enoyl-ACP reductase (PfENR) enzymes. Compound 1 (IC₅₀) 0.68 μM) showed inhibitory activity on β-glucuronidase enzyme, while 3 (IC₅₀) 7.69 μM) exhibited a weak inhibitory activity against P. falciparum enoyl-ACP reductase (PfENR).

The potential of anti-malarial compounds derived from African medicinal plants, part II: a pharmacological evaluation of non-alkaloids and non-terpenoids

“…The isoflavone dimer, mucusisoflavone C ( 33 ), derived from the figs of Ficus mucuso , harvested near Yaoundé in Cameroon, exhibited a weak inhibitory activity against the validated drug target P. falciparum enoyl-ACP reductase ( Pf ENR), with an IC 50 value of 7.69 μM [66]. …”

New insights of phenolic compounds from optimized fruit extract of Ficus auriculata

“…Isoflavones consisted of three compounds such as trihydroxy-octadecadienoic acid, trihydroxy octadecanoic acid and hydroxy-octadecatrienoic acid (compounds 10, 11, 13). Most of them have been reported in several Ficus species, including F. carica , F. tikoua , and F. mucuso 43 , 46 , 47 .

Figure 8 LC–MS fingerprinting analysis of fruits of F. auriculata analysed in the negative ionization mode.

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High-Resolution Inhibition Profiling Combined with HPLC-HRMS-SPE-NMR for Identification of PTP1B Inhibitors from Vietnamese Plants

“…From 40.0 g dried material of F. racemosa , 450 mg EtOAc extract was obtained and subsequently subjected to preparative-scale HPLC (described in Section 3.6 ) to obtain the material eluted as peak 1 (3.5 mg), 2 (1.2 mg), 3 (0.7 mg), 4 (1.5 mg), 5 (1.2 mg), 6 (0.6 mg), and 7 (0.4 mg). On the basis of HRMS as well as 1D and 2D NMR spectra, peak 5 was assigned to mucusisoflavone B ( 4 ), C 40 H 32 O 10 , HR-ESIMS(+) m / z 673.2068 [M + H] + , 1 H-NMR (600 MHz, acetone- d 6 ) ppm: δ 13.03 (2H, s, OH-5, OH-16′′), 8.24 (1H, s, H-13′′), 8.14 (1H, s, H-2), 7.74 (1H, d, J = 2.1 Hz, H-23′′), 7.37 (1H, dd, J = 8.3, 2.1 Hz, H-27′′), 7.35 (1H, dd, J = 8.2, 2.0 Hz, H-6′), 7.33 (1H, d, J = 2.0 Hz, H-2′), 7.10 (1H, d, J = 16.2 Hz, H-11′′), 6.96 (1H, d, J = 8.3 Hz, H-26′′), 6.90 (1H, d, J = 8.2 Hz, H-5′), 6.60 (1H, d, J = 16.2 Hz, H-10′′), 6.43 (1H, d, J = 2.2 Hz, H-19′′), 6.42 (1H, d, J = 2.2 Hz, H-8), 6.29 (1H, d, J = 2.2 Hz, H-17′′), 6.28 (1H, d, J = 2.2 Hz, H-6), 5.19 (1H, m, H-5′′), 3.92 (1H, m, H-4′′), 2.12 and 1.80 (each 1H, overlapping signals, H 2 -3′′), 1.84 (3H, s, H 3 -7′′), 1.78 (3H, s, H 3 -8′′), 1.55 (3H, s, H 3 -9′′); 13 C-NMR (150 MHz, acetone- d 6 ) ppm: δ 181.6 (C-4, C-15′′), 165.2 (C-7, C-18′′), 163.9 (C-5, C-16′′), 159.1 (C-9), 159.0 (C-20′′), 155.7 (C-4′, C-25′′), 154.6 (C-2), 154.3 (C-13′′), 136.3 (C-10′′), 134.0 (C-6′′), 130.6 (C-2′), 130.2 (C-27′′), 129.3 (C-6′), 128.5 (C-23′′), 128.3 (C-5′′), 125.4 (C-3′), 124.8 (C-22′′), 124.2 (C-3), 124.0 (C-14′′), 123.6 (C-1′), 123.5 (C-24′′), 123.2 (C-11′′), 117.9 (C-5′), 116.5 (C-26′′), 106.1 (C-10, C-21′′), 99.9 (C-6, C-17′′), 94.5 (C-8, C-19′′), 77.4 (C-2′′), 40.1 (C-3′′), 32.6 (C-4′′), 26.0 (C-8′′), 24.4 (C-9′′), 18.1 (C-7′′) [ 25 ]. Peaks 3 , 6 and 7 were impure and the subsequent purification of these peaks was not successful despite several efforts.…”