Anti-oral Microbial Flavanes from Broussonetia papyrifera Under the Guidance of Bioassay

Abstract

A new flavane, bropapyriferol (1), and eleven known ones were isolated from the EtOAc part of Broussonetia papyrifera under the guidance of bioassay. The structure of compound 1 was determined by extensive 1D and 2D NMR, [α]D spectroscopic data and quantum computation. Daphnegiravan F (2) and 5,7,3′,4′-tetrahydroxy-3-methoxy-8,5′-diprenylflavone (3) showed significantly anti-oral microbial activity against five Gram-positive strains and three Gram-negative strains in vitro. Especially, compound 3 was more potent in suppressing Actinomyces naeslundii and Porphyromonas gingivalis (MIC = 1.95 ppm) than the positive control, triclosan.Graphical Abstract Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-019-0197-y) contains supplementary material, which is available to authorized users.

The Genus Broussonetia: An Updated Review of Phytochemistry, Pharmacology and Applications

“…In 2017, Park et al analyzed the antibacterial activity of papyriflavonol A within the dosage of 1-1000 µM; the results showed that the potent inhibitory effect of PLpro, with an IC 50 value of 3.7 µM, along with a further study, showed that it may be a potential anti-COVID-19 agent [105]. Geng et al [17] indicated that 5,7,3 ,4 -tetrahydroxy-3-methoxy-8,5 -diprenylflavone, isolated from the BP air-dried aerial part, showed more antibacterial activity in suppressing Actinomyces naeslundii and Porphyromonas gingivalis (MIC = 1.95 ppm) than the positive control, triclosan, at a dosage of 0.12-250 ppm. In 2021, Ghosh et al [18] found that six polyphenols (broussochalcone A, papyriflavonol A, 3 -(3-methylbut-2-enyl-3 ,4 ,7-trihydroxyflavane, broussoflavan A, kazinol F, and kazinol J) showed greater Mpro inhibitory effect than two repurposed drugs (lopinavir and darunavir) and may serve as promising anti-COVID-19 drugs.…”

“…The genus of Broussonetia has been found to present 338 compounds, including flavonoids, polyphenols, alkaloids, terpenoids, steroids, and others. Active compounds isolated from Broussonetia have been demonstrated to have several biological properties, including antitumor [2], antioxidant [13], anti-inflammation [14], antidiabetic [15], anti-obesity [16], antibacterial [17], and antiviral activities [18], as well as being used for skin whitening [19] and against skin wrinkles, as well as many other uses. In terms of representative applications, Broussonetia species could be used as forage for cattle, Hu rams and lambs, growing goats, and other animals because of the high content of protein and fiber [20,21].…”

Biological Activities of Paper Mulberry (Broussonetia papyrifera): More than a Skin-Lightening Agent

“…The seed oil of paper mulberry exerted antibacterial activities against Staphylococcus aureus, Proteus vulgaris, Bacillus cereus, and Enterobacter aerogenes, but did not affect fungal strains [57]. Extracts from the aerial parts of paper mulberries and the derived compounds, daphnegiravan F and 5,7,3 ,4 -tetrahydroxy-3-methoxy-8,5 -diprenylflavone, exhibited an anti-oral microbial effect on both Gram-positive and Gram-negative bacteria [76]. Prenylated flavonoids from paper mulberry also possess antimicrobial activities.…”

Progress in Chemical Constituents and Bioactivities of Broussonetia pa-pyrifera (L.) Vent

“…Above-mentioned compound 3 was isolated from the barks for the first time and compounds 7 and 8 were two new prenylflavones. [14][15][16] Besides, broussochalcone B (12), 3,4-dihydroxyisolonchocarpin (13), 4-hydroxyisolonchocarpin (14), kazinol E (15), 8-(1,1-dimethylallyl)-5'-(3-methylbut-2-enyl)-3',4',5,7-tetrahydroxyflanvonol (16), brossoflurenone A (17) and brossoflurenone B (18) were isolated from roots, in which compounds 17 and 18 were two novel benzofluoreneones. [17] Besides the above-mentioned compounds, flavonoids and their glycosides were also isolated from the fruits and leaves of B. papyrifera, which were named apigenin (19), apigenin-7-Oβ-D-glucopyranoside (20), broupapyrin A (21), cosmosiin (22), luteolin-7-O-β-D-glucopyranoside (23), and apigenin-6-C-β-Dglucopyranside (24).…”

“…Geng et al [16] reported that flavonols in B. papyrifera showed significantly anti-oral microbial activity in vitro. Among them, compound 5,7,3',4'-tetrahydroxy-3-methoxy-8,5'-diprenylflavone (8) was more effective in suppressing Actinomyces naeslundii and Porphyromonas gingivalis (MIC = 1.95 ppm) than the positive control, triclosan.…”