Structural characterization of prenylated compounds from Broussonetia kazinoki and their antiosteoclastogenic activity

Vu, Ngoc Khanh; Ha, Manh Tuan; Kim, Chung Sub; Gal, Minju; Kim, Jeong Ah; Woo, Mi Hee; Lee, Jeong‐Hyung

doi:10.1016/j.phytochem.2021.112791

Cited by 6 publications

(11 citation statements)

References 26 publications

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“…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].…”

Section: Introductionmentioning

confidence: 99%

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

Chen¹,

Wang²,

Li³

et al. 2022

Molecules

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The Broussonetia genus (Moraceae), recognized for its value in many Chinese traditional herbs, mainly includes Broussonetia papyrifera (L.) L’Hér. ex Vent. (BP), Broussonetia kazinoki Siebold (BK), and Broussonetia luzonica (Blanco) Bureau (BL). Hitherto, researchers have found 338 compounds isolated from BP, BK, and BL, which included flavonoids, polyphenols, phenylpropanoids, alkaloids, terpenoids, steroids, and others. Moreover, its active compounds and extracts have exhibited a variety of pharmacological effects such as antitumor, antioxidant, anti-inflammatory, antidiabetic, anti-obesity, antibacterial, and antiviral properties, and its use against skin wrinkles. In this review, the phytochemistry and pharmacology of Broussonetia are updated systematically, after its applications are first summarized. In addition, this review also discusses the limitations of investigations and the potential direction of Broussonetia. This review can help to further understand the phytochemistry, pharmacology, and other applications of Broussonetia, which paves the way for future research.

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Section: Introductionmentioning

confidence: 99%

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

Chen¹,

Wang²,

Li³

et al. 2022

Molecules

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“…The long-range correlations from H-9 to C-4′/5′, H-14 to C-1′/6′, and H-2 to C-2′ indicated that two prenyl groups were adjacent to each other and attached at the C-5′ and C-6′ positions of ring B. The large coupling constant (11.5 Hz) between H-2 and H-3 indicated that ring C had a 2,3- trans -configuration, not a cis -configuration which gave a small J value (~2 Hz) [ 3 ], and the absolute configuration of compound 4 was considered to be 2 R ,3 R based on its positive specific rotation (

+74.6°) by comparison with the reported data of related structures [ 3 , 21 ]. Based on the above analysis, the structure of compound 4 was assigned (2 R ,3 R )-3,5,7,3′,4′-pentahydroxy-5′,6′-diprenylflavanonol, and was named broussonol N.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Broussonetia kazinoki , a deciduous shrub tree belonging to the family Moraceae, is widely distributed throughout Korea, China, and Japan [ 1 , 2 , 3 ]. Since ancient times, its leaves, branches, roots and fruits have been used for various therapeutic purposes including the amelioration of vision, and suppression of edema [ 1 , 2 , 3 , 4 ]. In addition, it has been traditionally used for dermatologic diseases such as burns and acne in Korea according to the Principles and Practice of Eastern Medicine , an encyclopedia of medical knowledge [ 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

“…In addition, it has been traditionally used for dermatologic diseases such as burns and acne in Korea according to the Principles and Practice of Eastern Medicine , an encyclopedia of medical knowledge [ 5 , 6 ]. Previous biological investigations have demonstrated that B. kazinoki exhibited a variety of pharmacological effects, such as antioxidant, anti-inflammatory, anticancer, anti-allergic, anti-diabetic, and anti-hyperglycemic activities [ 2 , 3 , 4 , 5 , 6 , 7 ]. Moreover, the extract of B. kazinoki has been registered as a skin-whitening agent by the Korea Food and Drug Administration (KFDA) due to its potent tyrosinase inhibitory and anti-melanogenic effects [ 5 , 8 ].…”

Section: Introductionmentioning

confidence: 99%

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Microbial Transformation and Biological Activities of the Prenylated Aromatic Compounds from Broussonetia kazinoki

Choi¹,

Han²,

Park³

et al. 2022

Molecules

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Broussonetia kazinoki has been used as a traditional medicine for the treatment of burns and acne, and its extracts have been found to show tyrosinase inhibitory and anticancer activities. In this study, the tyrosinase inhibitory and cytotoxic activities of B. kazinoki were explored, leading to the isolation of kazinol C (1), kazinol E (2), kazinol F (3), broussonol N (4), and kazinol X (5), of which the compounds 4 and 5 have not been previously reported. Microbial transformation has been recognized as an efficient tool to generate more active metabolites. Microbial transformation of the major compounds 1 and 3 was conducted with Mucor hiemalis, where four glucosylated metabolites (6–9) were produced from 1, while one hydroxylated (10) and one glucosylated (11) metabolites were obtained from 3. Structures of the isolated metabolites were determined by extensive spectroscopic analyses. All compounds were evaluated for their tyrosinase inhibitory and cytotoxic activities. Compound 3 and its metabolites, kazinol Y (10) and kazinol F-4″-O-β-d-glucopyranoside (11), exhibited the most potent tyrosinase inhibitory activities with the IC50 values ranging from 0.71 to 3.36 µM. Meanwhile, none of the metabolites, except for kazinol C-2′,3″-di-O-β-d-glucopyranoside (7), showed moderate cytotoxic activities (IC50 17.80 to 24.22 µM) against A375P, B16F10 and B16F1 cell lines.

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Phytochemistry and pharmacology of natural prenylated flavonoids

Wang

Luo

et al. 2023

Arch. Pharm. Res.

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Prenylated flavonoids are a special kind of flavonoid derivative possessing one or more prenyl groups in the parent nucleus of the flavonoid. The presence of the prenyl side chain enriched the structural diversity of flavonoids and increased their bioactivity and bioavailability. Prenylated flavonoids show a wide range of biological activities, such as anti-cancer, anti-inflammatory, neuroprotective, anti-diabetic, anti-obesity, cardioprotective effects, and anti-osteoclastogenic activities. In recent years, many compounds with significant activity have been discovered with the continuous excavation of the medicinal value of prenylated flavonoids, and have attracted the extensive attention of pharmacologists. This review summarizes recent progress on research into natural active prenylated flavonoids to promote new discoveries of their medicinal value. Supplementary Information The online version contains supplementary material available at 10.1007/s12272-023-01443-4.

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Structural characterization of prenylated compounds from Broussonetia kazinoki and their antiosteoclastogenic activity

Cited by 6 publications

References 26 publications

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

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

Microbial Transformation and Biological Activities of the Prenylated Aromatic Compounds from Broussonetia kazinoki

Phytochemistry and pharmacology of natural prenylated flavonoids

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