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Comparative Study
. 2017 Mar 2;12(3):e0172069.
doi: 10.1371/journal.pone.0172069. eCollection 2017.

Comparison of pancreatic lipase inhibitory isoflavonoids from unripe and ripe fruits of Cudrania tricuspidata

Yang Hee Jo  1 , Seon Beom Kim  1 , Qing Liu  1 , Seon-Gil Do  2 , Bang Yeon Hwang  1 , Mi Kyeong Lee  1
Affiliations
Comparative Study

Comparison of pancreatic lipase inhibitory isoflavonoids from unripe and ripe fruits of Cudrania tricuspidata

Yang Hee Jo et al. PLoS One. .

Abstract

The composition and content of the active constituents and their biological activity vary according to diverse factors including their maturation stages. A previous study showed that the fruits of Cudrania tricuspidata inhibited pancreatic lipase activity, a key enzyme in fat absorption. In this study, we investigated the chemical composition and pancreatic lipase inhibitory activity of unripe and ripe fruits of C. tricuspidata. Unripe fruits of C. tricuspidata have a higher content of total phenolic and flavonoids and exhibited stronger pancreatic lipase inhibition compared to ripe fruits. HPLC analysis revealed the different chemical compositions of the unripe and ripe fruits. Further fractionation resulted in the isolation of 30 compounds including two new isoflavonoids. Analysis of the chemical constituents of the unripe and ripe fruits revealed that a 2,2-dimethylpyran ring, a cyclized prenyl, was the predominant side chain in the unripe fruits, whereas it was a linear prenyl group in the ripe fruits. In addition, a new isoflavonoid (19) from the unripe fruits showed the most potent inhibition on pancreatic lipase. Taken together, the maturation stage is an important factor for maximum efficacy and that unripe fruits of C. tricuspidata are a good source of new bioactive constituents for the regulation of obesity.

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Conflict of interest statement

Competing Interests: The author [SGD] is an employee and shareholder of the company Univera. [SGD] contributed to this work by designing the experiment and conducting data analysis. Univera did not have any additional role in the study design, data collection and analysis, decision to publish, or preparation of the manuscript. This does not alter our adherence to PLOS ONE policies on sharing data and materials.

Figures

Fig 1
Fig 1. (A) Photographs of unripe and ripe fruits of C. tricuspidata, (B) effect on pancreatic lipase activity, (C) relative ratio of EtOAc and aqueous fraction, (D) effect on total flavonoid contents, and (E) effect on total phenolic content.
Fig 2
Fig 2. HPLC chromatogram of extract from (A) unripe and (B) ripe fruits.
Chromatographic separation was accomplished by Gemini-NX 3μ C18 110A (150 x 4.60 mm) using acetonitrile-water (60:40) at a flow rate of 1.0 mL/min. The wavelengths for the detection was set at 254 nm.
Fig 3
Fig 3. Key HMBC correlation of compounds 7 and 19 from unripe fruits of C. tricuspidata.
Fig 4
Fig 4. Chemical structures of compounds isolated from unripe and ripe fruits of C. tricuspidata fruits.
Fig 5
Fig 5. Effect of compounds on pancreatic lipase activity.
Fig 6
Fig 6. Lineweaver-Burk plots of the inhibitory activity of compound 19.
See this image and copyright information in PMC

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