Antioxidant and Tyrosinase Inhibitory Effects of Neolignan Glycosides from Crataegus pinnatifida Seeds

Xiao-Xiao Huang; Qing-Bo Liu; Jie Wu; Li-Hong Yu; Qian Cong; Yan Zhang; Li-Li Lou; Ling-Zhi Li; Shao-Jiang Song

doi:10.1055/s-0034-1383253

Planta Medica, Table of Contents

Planta Med 2014; 80(18): 1732-1738
DOI: 10.1055/s-0034-1383253

Natural Product Chemistry

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Antioxidant and Tyrosinase Inhibitory Effects of Neolignan Glycosides from Crataegus pinnatifida Seeds

Xiao-Xiao Huang^*

¹Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang, P. R. China

²Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, P. R. China

,

Qing-Bo Liu^*

¹Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang, P. R. China

²Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, P. R. China

,

Jie Wu

¹Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang, P. R. China

²Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, P. R. China

,

Li-Hong Yu

¹Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang, P. R. China

²Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, P. R. China

,

Qian Cong

¹Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang, P. R. China

²Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, P. R. China

,

Yan Zhang

³School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, P. R. China

,

Li-Li Lou

¹Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang, P. R. China

²Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, P. R. China

,

Ling-Zhi Li

¹Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang, P. R. China

²Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, P. R. China

,

Shao-Jiang Song

¹Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang, P. R. China

²Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, P. R. China

› Author Affiliations

Abstract

In our efforts to find an inhibitor of melanin formation and develop potential depigmenting agents for skin-protecting cosmetics and medicinal products from natural resources, we focused on the seeds of Crataegus pinnatifida which showed antioxidant and tyrosinase-inhibiting activities. By activity-guided fractionation of an extract of C. pinnatifida seeds, four new neolignan glycosides, pinnatifidaninsides A–D (1–4), along with two known compounds (5–6), were isolated. Their structures were elucidated by spectroscopic analyses, especially 1D, 2D NMR and CD spectra. The antioxidant and tyrosinase-inhibiting activities of all isolates were assayed. Compound 6 showed good activity against 2,2-diphenyl-1-pikrylhydrazyl, while compounds 1, 2, 5, and 6 exhibited strong 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) free radical scavenging activity, being as effective as, or even more effective than the positive control Trolox. Moreover, compounds 5 and 6 displayed a moderate mushroom tyrosinase inhibitory activity.

Key words

Crataegus pinnatifida - Rosaceae - hawthorn - neolignan glycosides - tyrosinase-inhibiting activity - antioxidant activity

Full Text

References

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