PDF herunterladen
Planta Med 2018; 84(05): 336-343
DOI: 10.1055/s-0043-121698
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Isoprenylated Phenolic Compounds from Morus macroura as Potent Tyrosinase Inhibitors

Yifan Wang
1   Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai, Peopleʼs Republic of China
2   Innovation Center of Chinese Medicine, China State Institute of Pharmaceutical Industry, Shanghai, Peopleʼs Republic of China
,
Liangjin Xu
2   Innovation Center of Chinese Medicine, China State Institute of Pharmaceutical Industry, Shanghai, Peopleʼs Republic of China
,
Wen Gao
3   Shineway Pharmaceutical Group Co. Ltd., Shijiazhuang, Hebei, Peopleʼs Republic of China
,
Lixin Niu
2   Innovation Center of Chinese Medicine, China State Institute of Pharmaceutical Industry, Shanghai, Peopleʼs Republic of China
,
Chunyue Huang
2   Innovation Center of Chinese Medicine, China State Institute of Pharmaceutical Industry, Shanghai, Peopleʼs Republic of China
,
Peiming Yang
2   Innovation Center of Chinese Medicine, China State Institute of Pharmaceutical Industry, Shanghai, Peopleʼs Republic of China
,
Xiao Hu
2   Innovation Center of Chinese Medicine, China State Institute of Pharmaceutical Industry, Shanghai, Peopleʼs Republic of China
› Institutsangaben
Weitere Informationen

Publikationsverlauf

received 06. Juli 2017
revised 14. Oktober 2017

accepted 16. Oktober 2017

Publikationsdatum:
02. November 2017 (online)

Auch verfügbar auf
    Lizenzen und Reprints

Abstract

Three new Diels-Alder adducts, macrourins E – G (1–3), one new 2-arylbenzofuran, macrourin H (4), and eight known Diels-Alder adducts (5–12) were isolated from Morus macroura. Their structures were elucidated through extensive analysis of spectroscopic data. The 1H NMR and ECD trends in the determination of the configurations of these Diels-Alder adducts were summarized. The tyrosinase inhibitory activities of all compounds isolated were evaluated, and the new compounds (1–4) as well as the eight known compounds (5–12) were found to be potent with IC50 values ranging from 0.39 to 4.54 µM. Among them, 1 showed the best tyrosinase inhibitory activity with an IC50 value of 0.39 µM, approximately 50 times stronger than the positive control, kojic acid.

Key words

Morus macroura - Moraceae - Diels-Alder adducts - 2-arylbenzofuran - kojic acid - tyrosinase inhibitory activity

Supporting Information

    The 1D NMR, 2D NMR, HRESIMS, and ECD spectra for compounds 1–4, the plausible biogenetic pathway proposed for compound 3, the chiral separation chromatograph of compound 4, the 1H NMR data of two pairs of all-trans and cis-trans DAs (2 and 10, and 5 and 6), and the ECD spectra reported by Nomura et al. [13] are available as Supporting Information.

  • Supporting Information
 

  • References

  • 1 Agarwal S, Kanwar K. Comparison of genetic transformation in Morus alba L. via different regeneration systems. Plant Cell Rep 2007; 26: 177-185
    CrossrefPubMedSuche in Google Scholar
  • 2 Nomura T, Fukai T. Constituents of the cultivated mulberry tree. Heterocycles 1981; 15: 31-67
    PubMedSuche in Google Scholar
  • 3 Hu X, Wu JW, Zhang XD, Zhao QS, Huang JM, Wang HY, Hou AJ. Isoprenylated flavonoids and adipogenesis-promoting constituents from Morus nigra . J Nat Prod 2011; 74: 816-824
    CrossrefPubMedSuche in Google Scholar
  • 4 Hu X, Wang M, Zhao QS, Wang HY, Hou AJ. 2-Arylbenzofuran dimer, flavonoid and tyrosinase inhibitory constituents of Morus yunnanensis . J Nat Prod 2012; 75: 82-87
    CrossrefPubMedSuche in Google Scholar
  • 5 Dai SJ, Ma ZB, Wu Y, Chen RY, Yu DQ. Guangsangons F-J, anti-oxidant and anti-inflammatory Diels-Alder type adducts, from Morus macroura Miq. Phytochemistry 2004; 65: 3135-3141
    CrossrefPubMedSuche in Google Scholar
  • 6 Dai SJ, Mi ZM, Ma ZB, Li S, Chen RY, Yu DQ. Bioactive Diels-Alder type adducts from the stem bark of Morus macroura . Planta Med 2004; 70: 758-763
    Thieme ConnectPubMedSuche in Google Scholar
  • 7 Nguyen NT, Nguyen M, Nguyen HX, Nguyen M. Tyrosinase inhibitors from the wood of Artocarpus heterophyllus . J Nat Prod 2012; 75: 1951-1955
    CrossrefPubMedSuche in Google Scholar
  • 8 Yang ZZ, Wang YC, Wang Y, Zhang YF. Bioassay-guided screening and isolation of α-glucosidase and tyrosinase inhibitors from leaves of Morus alba . Food Chem 2012; 13: 617-625
    PubMedSuche in Google Scholar
  • 9 Zheng ZP, Cheng KW, Zhu Q, Wang XC, Lin ZX, Wang M. Tyrosinase inhibitory constituents from the roots of Morus nigra: a structure-activity relationship study. J Agric Food Chem 2010; 58: 5368-5373
    CrossrefPubMedSuche in Google Scholar
  • 10 Kim YJ, Uyama H. Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci 2005; 62: 1707-1723
    CrossrefPubMedSuche in Google Scholar
  • 11 Han P, Chen CQ, Zhang CL, Zhou KK, Chen QX. Inhibitory effects of 4-chlorosalicylic acid on mushroom tyrosinase and its antimicrobial activities. Food Chem 2008; 107: 797-803
    CrossrefPubMedSuche in Google Scholar
  • 12 Hano Y, Nomura T, Ueda S. Two new Diels-Alder type adducts, mulberrofuran T and Kuwanonl E from callus tissues of Morus alba L. Heterocycles 1989; 29: 2035-2041
    CrossrefPubMedSuche in Google Scholar
  • 13 Hano Y, Suzuki S, Nomura T, Iitaka Y. Absolute configuration of natural Diels-Alder type adducts from the Morus root bark. Heterocycles 1988; 27: 2315-2325
    CrossrefPubMedSuche in Google Scholar
  • 14 Wang M, Gao LX, Wang J, Li JY, Yu MH, Li J, Hou AJ. Diels-Alder adducts with PTP1B inhibition from Morus notabilis . Phytochemistry 2015; 109: 140-146
    CrossrefPubMedSuche in Google Scholar
  • 15 Kang J, Yu DQ, Chen RY. Five new Diels-Alder type adducts from the stem and root bark of Morus mongolica . Planta Med 2006; 72: 52-59
    Thieme ConnectPubMedSuche in Google Scholar
  • 16 Fukai T, Hano Y, Hirakura K, Nomura T, Uzawa J. Structures of a novel 2-arylbenzofuran derivative and two flavone derivatives from the cultivated mulberry tree (Morus lhou KOIDZ.). Chem Pharm Bull 1985; 33: 4288-4295
    CrossrefPubMedSuche in Google Scholar
  • 17 Tee JT, Chee CF, Buckle MJC, Lee VS, Chong WL, Khaledi H, Rahman NA. Model studies on construction of the oxabicyclic [3.3.1] core of the mulberry Diels-Alder adducts morusalbanol A and 441772-64-1. Tetrahedron Lett 2015; 56: 5082-5085
    CrossrefPubMedSuche in Google Scholar
  • 18 Chen HD, Ding YQ, Yang SP, Li XC, Wang XJ, Zhang HY, Yue JM. Morusalbanol A, a neuro-protective Diels-Alder adduct with an unprecedented architecture from Morus alba. . Tetrahedron 2012; 68: 6054-6058
    CrossrefPubMedSuche in Google Scholar
  • 19 Hano Y, Kohno H, Itoh M, Nomura T. Structures of three new 2-arylbenzofuran derivatives from the chinese crude drug “Sang-Bai-Pi” (morus root bark). Chem Pharm Bull 1985; 33: 5294-5300
    CrossrefPubMedSuche in Google Scholar
  • 20 Tan YX, Gong T, Liu C, Chen RY, Yu DQ. Five new 2-arylbenzofuran derivatives from Morus wittiorum . Chem Pharm Bull 2010; 58: 579-581
    CrossrefPubMedSuche in Google Scholar
  • 21 Dai SJ, Chen RY, Yu DQ. Diels-Alder type adducts of Morus macroura Miq. J China Pharm Univ 2006; 37: 119-122
    PubMedSuche in Google Scholar
  • 22 Zheng ZP, Tan HY, Wang MF. Tyrosinase inhibition constituents from the roots of Morus australis . Fitoterapia 2012; 83: 1008-1013
    CrossrefPubMedSuche in Google Scholar
  • 23 Jeong SH, Ryu YB, Curtislong MJ, Ryu HW, Baek YS, Kang JE. Tyrosinase inhibitory polyphenols from roots of Morus lhou . J Agric Food Chem 2009; 59: 1195-1203
    PubMedSuche in Google Scholar