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CC BY 4.0 · Pharmaceutical Fronts 2021; 03(01): e8-e12
DOI: 10.1055/s-0041-1730957
Original Article

Phenolic Constituents from the Stems of Morus nigra and their α-Glucosidase Inhibitory Activities

Ling-Ling Wang
1   State Key Laboratory of New Drug and Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
,
Liang-Jin Xu
1   State Key Laboratory of New Drug and Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
,
Meng-Jie Ma
1   State Key Laboratory of New Drug and Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
,
Chun-Yue Huang
1   State Key Laboratory of New Drug and Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
,
Tong Wu
1   State Key Laboratory of New Drug and Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
,
Xiao Hu
1   State Key Laboratory of New Drug and Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, People's Republic of China
2   Shanghai Xinshengyuan Pharmaceutical Co., Ltd., Shanghai, People's Republic of China
› Author Affiliations Funding This work was supported by the Natural Science Foundation of Shanghai (Grant No.19ZR1454400), the National Natural Science Foundation of China (Grant No. 81803844), and the National Science and Technology Major Project (Grant No. 2018ZX09731-016).
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Abstracts

A new sanggenon-type flavanone, nigragenon F (1), together with 11 known compounds, trans-resveratrol (2), (E)-4-isopentenyl-3,5,2′,4′-tetrahydroxystilbene (3), notabilisin E (4), notabilisin A (5), morusin (6), petalopurpurenol (7), 8-geranyl-5,7-dihydroxycoumarin (8), 2,4-dihydroxybenzaldehyde (9), 4-ethoxy-2,6-dihydroxybenzoic acid (10), 3-hydroxy-4-methoxybenzaldehyde (11), and 4-hydroxybenzaldehyde (12), were isolated from the stems of Morus nigra. Compound 10 was a new natural product, compounds 3, 4, 7, and 8 were reported from the Morus genus for the first time. All of the isolated compounds were evaluated for their α-glucosidase inhibition activity. Among them, six compounds showed obvious inhibitory effects against α-glucosidase with IC50 values ranging from 1.24 to 19.00 µmol/L.

Keywords

Moraceae - Morus nigra - sanggenon-type flavanone - nigragenon F - α-glucosidase

Supplementary Material



Publication History

Received: 02 February 2021

Accepted: 30 April 2021

Article published online:
23 June 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/)

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  • Reference

  • 1 Zhang MQ. Isolation, Purification and Characterization of α-Glucosidase Inhibitors from Sargassum fusiforme. [in Chinese]. Jiangsu: Jiangnan University; 2020
    Google Scholar
  • 2 Li Y, Sun B, Hu X. et al. Research and development progress on the synthesized utilization of mulberry. [in Chinese]. North Sericulture 2009; 30 (03) 12-15
    Google Scholar
  • 3 Jiang NZ, Bo M, Wu ZP, Tan JZ. The advancement of lowering blood glucose studies on mulberry pharmaceutical resources. [in Chinese]. Jiangsu Sericulture 2005; (04) 1-4
    Google Scholar
  • 4 Lu H, Ding TL, Wu SG. et al. The medicinal value of Xinjiang black mulberry and its application in Uighur medicine. [in Chinese]. Can Ye Ke Xue 2011; 37 (06) 1098-1101
    Google Scholar
  • 5 Hu X, Wu JW, Zhang XD. et al. Isoprenylated flavonoids and adipogenesis-promoting constituents from Morus nigra. J Nat Prod 2011; 74 (04) 816-824
    CrossrefPubMedGoogle Scholar
  • 6 Xu L, Huang T, Huang C, Wu C, Jia A, Hu X. Chiral separation, absolute configuration, and bioactivity of two pairs of flavonoid enantiomers from Morus nigra. Phytochemistry 2019; 163: 33-37
    CrossrefPubMedGoogle Scholar
  • 7 Xu L, Yu M, Niu L. et al. Phenolic compounds isolated from Morus nigra and their α-glucosidase inhibitory activities. Nat Prod Res 2020; 34 (05) 605-612
    CrossrefPubMedGoogle Scholar
  • 8 Wei Q, Ji XY, Xu F, Li QR, Yin H. Chemical constituents from leaves of Hibiscus syriacus and their α-glucosidase inhibitory activities [in Chinese]. Zhong Yao Cai 2015; 38 (05) 975-979
    PubMedGoogle Scholar
  • 9 Fukai T, Pei YH, Nomura T, Xu CQ, Wu LJ, Chen YJ. Isoprenylated flavanones from Morus cathayana . Phytochemistry 1998; 47 (02) 273-280
    CrossrefGoogle Scholar
  • 10 Shi YQ, Fukai T, Ochiai M, Nomura T. Absolute structures of 3-hydroxy-2-prenylflavanones with an ether linkage between the 2′- and 3-positions from moraceous plants. Heterocycles 2001; 55 (01) 13-20
    CrossrefGoogle Scholar
  • 11 Sivakumar B, Murugan R, Baskaran A, Khadangale BP, Murugan S, Senthilkumar UP. Identification and characterization of process-related impurities of trans-resveratrol. Sci Pharm 2013; 81 (03) 683-695
    CrossrefPubMedGoogle Scholar
  • 12 Jayasinghe ULB, Puvanendran S, Hara N, Fujimoto Y. Stilbene derivatives with antifungal and radical scavenging properties from the stem bark of Artocarpus nobilis. Nat Prod Res 2004; 18 (06) 571-574
    CrossrefPubMedGoogle Scholar
  • 13 Hu X, Ji J, Wang M. et al. New isoprenylated flavonoids and adipogenesis-promoting constituents from Morus notabilis. Bioorg Med Chem Lett 2011; 21 (15) 4441-4446
    CrossrefPubMedGoogle Scholar
  • 14 Nomura T, Fukai T, Yamada S. et al. Phenolic constituents of the cultivated mulberry tree (Morus alba L.). Chem Pharm Bull (Tokyo) 1976; 24: 2898-2900
    CrossrefGoogle Scholar
  • 15 Huang L, Fullas F, McGivney RJ. et al. A new prenylated flavonol from the root of Petalostemon purpureus. J Nat Prod 1996; 59 (03) 290-292
    CrossrefPubMedGoogle Scholar
  • 16 Sarker SD, Armstrong JA, Gray AI. Sesquiterpenyl coumarins and geranyl benzaldehyde derivatives from the aerial parts of Eriostemon myoporoides. Phytochemistry 1994; 37 (05) 1287-1294
    CrossrefGoogle Scholar
  • 17 Zheng ZP, Xu Y, Qin C. et al. Characterization of antiproliferative activity constituents from Artocarpus heterophyllus. J Agric Food Chem 2014; 62 (24) 5519-5527
    CrossrefPubMedGoogle Scholar
  • 18 Maruyama S, Kaneko Y. 4-Alkoxy-3,5-dihalo-2,6-dihydroxybenzoic acids. Ger Offen; 1969
    Google Scholar
  • 19 Bi D, Xia G, Li Y, Liang X, Zhang L, Wang L. Two new cassane diterpene lactams from the fruits of Caesalpinia mimosoides Lam. Nat Prod Res 2018; 32 (08) 875-879
    CrossrefPubMedGoogle Scholar
  • 20 Hornung PS, Masisi K, Malunga LN. Natural bioactive starch film from Amazon turmeric (Curcuma longa L.). Polym Bull 2018; 75 (10) 4735-4752
    CrossrefGoogle Scholar