A Novel 3-Arylcoumarin and Three New 2-Arylbenzofurans from Mucuna birdwoodiana

Gong, Ting; Wang, Dongxiao; Yang, Yan; Liu, Ping; Chen, Ruo-Yun; Yu, De‐Quan

doi:10.1248/cpb.58.254

Cited by 9 publications

(6 citation statements)

References 8 publications

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“…The NMR spectra of 1 were similar to those of 3 except for an additional hydroxyl group in aromatic ring B, which was further deduced by the extra 16 mass units [8]. The OH group was determined to be at C-3' by the three proton ABX spin system at H-2', H-5' and H-6' of coupling system at δ H 6.79 (d, J = 9.0) and 7.21 (d, J = 9.0), similar to the 1 H-NMR data of 4 [10], was assigned to the 2',4'-dimethoxyl-3'-hydroxyl-2-phenyl moiety (ring C). This was confirmed by the HMBC spectrum ( Figure 3).…”

supporting

confidence: 53%

“…coupling system at δ H 6.79 (d, J = 9.0) and 7.21 (d, J = 9.0), similar to the 1 H-NMR data of 4 [10], was assigned to the 2',4'-dimethoxyl-3'-hydroxyl-2-phenyl moiety (ring C). This was confirmed by the HMBC spectrum (Figure 3).…”

Section: -1745mentioning

confidence: 65%

“…Another methoxy at δ H 3.77 must be positioned at C-5 and one aromatic proton singlet at δ H 7.09 assigned as H-4 was determined by the key HMBC correlations of OCH 3 -5/C-5, H-4/C-5, C-6 and C-8 and the ROESY correlation between H-4/5-OMe. Thus, the structure of 2 was determined and named maclurin B. Phytochemical study of this plant also resulted in the isolation of six known compounds, ononin (3) [8], pterofuran (4) [10], osajin (5) [5c], pomiferin (6) [5c], 3,4-dihydroxybenzoic acid (7) [11] and 2,3,4-trihydroxybenzoic acid (8) [12], which were determined by comparison of their NMR and MS spectroscopic data with the reported values in the literature. Among them, compounds 3 and 4 were isolated from the genus Maclura Nutt for the first time.…”

Section: -1745mentioning

confidence: 99%

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Phenolics from the Fruits of Maclura pomifera

Wang

Wei

et al. 2017

Natural Product Communications

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Two new compounds, maclurin A (1) and maclurin B (2), and six known ones, ononin (3), pterofuran (4), osajin (5), pomiferin (6), 3,4-dihydroxybenzoic acid (7), and 2,3,4-trihydroxybenzoic acid (8) were isolated from the fruit of Maclura pomifera. Compounds 3 and 4 were isolated from the genus for the first time. Structure elucidation was achieved by spectroscopic measurements and by comparison with literature data. Compounds 2-4 exhibited activities against the cancer cell lines A549 and Panc-28 with GI 50 values from 18.1 to 32.2, and 20.6 to 43.5 µM, respectively. Compounds 2 and 4 also showed cytotoxicity against HCT 116 with GI 50 values of 47.2 and 24.4 µM, respectively.

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supporting

confidence: 53%

Section: -1745mentioning

confidence: 65%

Section: -1745mentioning

confidence: 99%

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Phenolics from the Fruits of Maclura pomifera

Wang

Wei

et al. 2017

Natural Product Communications

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“…Natural products containing 3-arylcoumarin compounds are mainly extracted and isolated from Glycyrrhiza uralensis Fisch., Glycyrrhiza glabra L. and Glycyrrhiza inflata Bat. (Licorice) 35–38 , Mucuna birdwoodiana (Leguminosae) 39 , Sphenostylis marginata ssp (Fabaceae) 40 and Pongamiopsis pervilleana (Baill) 41 ( Table 1 ).…”

Section: Chemistrymentioning

confidence: 99%

Natural source, bioactivity and synthesis of 3-Arylcoumarin derivatives

Zhang

Miao

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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3-arylcoumarins with different pharmacological properties widely exist in a variety of natural plants. The extensive research on 3-arylcoumarins was attributed to its therapeutic and relatively easy isolation. Therefore, 3-arylcoumarins can be recognised as useful structures for the design of novel compounds with potential pharmacological interest, particularly in the fields of anti-inflammatory, anti-cancer, antioxidant, Monoamine oxidase (MAO) enzyme inhibition, etc. The current review highlights the biological activities, design, and chemical synthetic methods of 3-arylcoumarins derivatives as well as their important natural product sources.

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“…The naturally-occurring 3-phenylcoumarins that have been published in the past decade are listed in Table 1. Mucodianin A was isolated from the vine stems of Mucuna birdwoodiana [1]. The 3-(4-ethynylphenyl)-4-formylcoumarin has been isolated from a methanol extract of the red ants of ChangBai Mountain, Tetramorium sp.…”

Section: Presence Of 3-phenylcoumarins In Naturementioning

confidence: 99%

3-Phenylcoumarins as a Privileged Scaffold in Medicinal Chemistry: The Landmarks of the Past Decade

2021

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3-Phenylcoumarins are a family of heterocyclic molecules that are widely used in both organic and medicinal chemistry. In this overview, research on this scaffold, since 2010, is included and discussed, focusing on aspects related to its natural origin, synthetic procedures and pharmacological applications. This review paper is based on the most relevant literature related to the role of 3-phenylcoumarins in the design of new drug candidates. The references presented in this review have been collected from multiple electronic databases, including SciFinder, Pubmed and Mendeley.

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A Novel 3-Arylcoumarin and Three New 2-Arylbenzofurans from Mucuna birdwoodiana

Cited by 9 publications

References 8 publications

Phenolics from the Fruits of Maclura pomifera

Phenolics from the Fruits of Maclura pomifera

Natural source, bioactivity and synthesis of 3-Arylcoumarin derivatives

3-Phenylcoumarins as a Privileged Scaffold in Medicinal Chemistry: The Landmarks of the Past Decade

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