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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
› Author Affiliations
Further Information

Publication History

received 06 July 2017
revised 14 October 2017

accepted 16 October 2017

Publication Date:
02 November 2017 (online)

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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

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