Biocatalytic Production of Acyclic Bis[bibenzyls] from Dihydroresveratrol by Crude Momordica charantia Peroxidase

Abstract

Biotransformation of dihydroresveratrol by crude Momordica charantia peroxidase provided six new acyclic bis[bibenzyls] 1-6. Their structures were established on the basis of NMR and MS analyses as C-C, C-O-C, and C-CH(2)-C dimers of dihydroresveratrol. Compounds 1-6 were tested for antiproliferative activity against human prostate cancer PC3 cell line in vitro, and 2 and 6 were found to be more potent than the parent compound.

Phenolic Constituents with Antioxidative, Tyrosinase Inhibitory and Anti-aging Activities from Dendrobium loddigesii Rolfe

“…Eleven known compounds were identified to be crepidatin 4 [24], moscatilin 5 [25], 4,5,4′-trihydroxy-3,3′-dimethoxybibenzyl 6 [26], 4′,5-dihydroxy-3,3′-dimethoxybibenzyl 7 [27], tristin 8 [28], batatasin III 9 [27], 3,5,3′-hydroxybibenzyl 10 [29], aphyllals C 11 [15], densiflorol A 12 [30], dihydroconiferyl dihydro- p -coumarate 13 [31], p -hydroxyphenethyl trans -ferulate 14 [32] by spectroscopic analysis and comparing their spectral data with literature.…”

Chemotypes and Biomarkers of Seven Species of New Caledonian Liverworts from the Bazzanioideae Subfamily

“…Due to the functionalization of vittatin ( 51 ), hypothesis can be proposed suggesting that this bis(bibenzyl) should be formed by biaryl meta - meta coupling at the aromatic ring A (or C) of lunularic acid ( 49a ) leading to a putative intermediate ( 50a ). It is interesting to note that Momordica charantia peroxidase catalyzes biaryl meta - meta coupling with dihydroresveratrol as substrate [ 36 ]. The last step could be the formation of a methylenedioxy junction between the two phenol functions in para position of the aromatic cycle (A and C) leading to vittatin ( 51 ) as shown in Figure 6 .…”

Cytotoxic bibenzyl dimers from the stems of Dendrobium fimbriatum Hook

“…The above data and its biological sources suggested that this compound should be a bibenzyl dimers derivative. 15,16,22,30 The HMBC spectrum of 1 demonstrated the expected key correlations: from H-7a to C-1a, C-2a and 7a, from H-6a to C-4a, C-5a and C-7a, from H-8a to C-1a, C-9a, C-10a and C-14a, from H-10a to C-9a, C-11a, C-12a and C-14a, from H-14a to C-13a; from H7b to C-2b, C-6b, C-9b and C-9b, from H-2b and H-6b to C-7b, from H-8b to C-1b, C-7b, C-9b, C-10b and C-14b, from H-10b and H-12b to C-11b. In addition, the correlations were observed from d H (OCH 3 ) 3.83, 3.76, 3.67, 3.66 to C-3a, C-3b, C-11b and C-11a in the HMBC spectrum, respectively.…”

“…This type of compound has only provided 14,14 0 methylene-diDR in the biotransformation experiment. 30 Considering the ecological habitat and a large of the bibenzyl compounds in D. fimbriatum Hook, it might be of the consequence of entophytes. The activity of those compounds in inhibiting tumor cell growth in vitro decreased as the number of oxygen-containing groups in the structure decreases.…”