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Molecules 2018, 23(6), 1361; https://doi.org/10.3390/molecules23061361

Phytochemical Composition, Hepatoprotective, and Antioxidant Activities of Phyllodium pulchellum (L.) Desv

1
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
2
Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266071, China
3
Marine Agriculture Research Center, Tobacco Research Institute of Chinese Academy of Agricultural Sciences, Qingdao 266101, China
*
Authors to whom correspondence should be addressed.
Received: 17 April 2018 / Revised: 28 May 2018 / Accepted: 4 June 2018 / Published: 5 June 2018
(This article belongs to the Section Natural Products Chemistry)
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Abstract

Phyllodiumpulchellum has been traditionally used as a medicinal herb because of its health-promoting effects, such as its hepatoprotective and antioxidant activities. In the present study, the petroleum ether fraction, ethyl acetate fraction, n-butanol fraction, and aqueous fraction were successively obtained from the ethanol extract of P. pulchellum. Two fractions, ethyl acetate fraction and n-butanol fraction, were found to display hepatoprotective and antioxidant activities. Further chemical investigation of the active fractions led to the isolation of its main constituents, including 11 flavonoids (111) and 8 indole alkaloids (1219). There were 9 flavonoids (19) that were obtained from the ethyl acetate fraction, and 2 flavonoids (10 and 11) and 8 alkaloids (1219) from the n-butanol fraction. Compounds 111 and 1619 were isolated for the first time from P. pulchellum, and 1, 2, 8, 11, and 18 were obtained from the genus Phyllodium initially. Subsequently, the isolated compounds were evaluated for their in vitro hepatoprotective effects on the human normal hepatocyte cell line L-O2 injured by d-galactosamine and radical scavenging activities against 1,1-diphenyl-2-picrylhydrazyl (DPPH). The flavonoids (−)-epigallocatechin (5) and (−)-epicatechin (6) exhibited prominent hepatoprotective activities with higher cell viability values (65.53% and 62.40% at 10 μM·mL−1, respectively) than the positive control, silymarin (61.85% at 10 μM·mL−1). In addition, compared with the positive control of vitamin C (IC50: 5.14 μg·mL−1), (−)-gallocatechin (3) and (−)-epigallocatechin (5) exhibited stronger antioxidant activities with IC50 values of 3.80 and 3.97 μg·mL−1, respectively. Furthermore, the total flavonoids from P. pulchellum were characterized using a high-performance liquid chromatography-linear ion trap quadrupole-Orbitrap-mass spectrometry (HPLC-LTQ-Orbitrap-MS). In total, 34 flavonoids were tentatively identified, which had not been previously reported from P. pulchellum. In addition, we performed a semi-quantitative analysis of the isolated flavonoids. The contents of compounds 111 were 3.88, 17.73, 140.35, 41.93, 27.80, 4.34, 0.01, 0.20, 9.67, 795.85, and 5.23 μg·g−1, respectively. In conclusion, this study revealed that the flavonoids that were isolated from P. pulchellum showed hepatoprotective and antioxidant activities, indicating that, besides alkaloids, the flavonoids should be the potential pharmacodynamic ingredients that are responsible for the hepatoprotective and antioxidant activities of P. pulchellum. View Full-Text
Keywords: Phyllodium pulchellum; flavonoids; hepatoprotective; antioxidant; HPLC-LTQ-Orbitrap-MS Phyllodium pulchellum; flavonoids; hepatoprotective; antioxidant; HPLC-LTQ-Orbitrap-MS
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Fan, Y.-C.; Yue, S.-J.; Guo, Z.-L.; Xin, L.-T.; Wang, C.-Y.; Zhao, D.-L.; Guan, H.-S.; Wang, C.-Y. Phytochemical Composition, Hepatoprotective, and Antioxidant Activities of Phyllodium pulchellum (L.) Desv. Molecules 2018, 23, 1361.

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