Hypolipidemic Activity of Monacolin Derivatives from the Highland Barley Monascus purpureus
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HYPOLIPIDEMIC ACTIVITY OF MONACOLIN DERIVATIVES FROM THE HIGHLAND BARLEY Monascus purpureus
Rongrui Wei,1 Qinge Ma,1* Wei Jiang,1 Guoyue Zhong,1 and Zhipei Sang2
A new monacolin derivative, namely (1S,2S,5 ′R,6R,8aR)-7-hydroxy-2,6-dimethyl-8-prenyl-1,2,6,8atetrahydronaphthalene-4′,5′-dihydro-2H-pyran-1′-one (1), and five known monacolin derivatives (2–6) were separated from the highland barley Monascus purpureus Went. for the first time. Their structures were elucidated on the basis of 1D and 2D NMR, HR-ESI-MS, and relevant references. Compounds 1–6 were tested for their hypolipidemic activities by measuring the triglyceride content in HepG2 cells. Among them, compounds 1 and 2 (10 μM) exhibited moderate hypolipidemic activity. Keywords: highland barley Monascus purpureus Went., monacolin derivative, hypolipidemic activity. Highland barley Monascus purpureus Went. is fermented by Monascus purpureus with highland barley as substrate, and it has uses in both medicine and food [1]. Modern research shows that highland barley Monascus purpureus can lower cholesterol, activate blood circulation, remove blood stasis, reduce blood fat, and lower blood sugar [2]. Previous phytochemical investigations show that highland barley Monascus purpureus contain polysaccharides [3], monascus pigment [4], monacolins [5], sterols [6], and statins [2]. Highland barley Monascus purpureus has been reported to display diverse biological activities, such as hypoglycemic [7], hypolipidemic [8], hepatoprotective [9], antitumor [10], hypotensive [11], and anti-inflammatory [12] activities. In our continuing efforts to investigate potential hypolipidemic agents from highland barley Monascus purpureus, a bioassay-guided investigation was implemented to study the hypolipidemic constituents of highland barley Monascus purpureus. We have isolated a new monacolin derivative (1) and five known monacolin derivatives (2–6) from highland barley Monascus purpureus for the first time. The isolated compounds (1–6) were evaluated for their hypolipidemic activities by measuring the triglyceride content in HepG2 cells. The isolation, structural elucidation, and biological evaluation of compounds 1–6 are described in this paper. O
O
O
O
H
H R
HO
H
H
H
R1 O
R
R
H
R=
1
2
3
4, 5
O
HO O H
6
4: R1 = COCH(CH3)CH2CH3 5: R1 = H
1) Research Center of Natural Resources of Chinese Medicinal Materials and Ethnic Medicine, Key Laboratory of Modern Preparation of TCM of Ministry of Education, Jiangxi University of Traditional Chinese Medicine, 330004, Nanchang, P. R. China, e-mail: [email protected]; 2) College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, 473061, Nanyang, P. R. China. Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2020, pp. 920–922. Original article submitted December 10, 2019. 1072
0009-3130/20/5606-1072 ©2020 Springer Science+Business Media, LLC
TABLE 1. 1H (400 MHz) and 13C (100 MHz) NMR of Compound 1 (acetone-d6, δ, ppm, J/Hz) C atom
δH
δC
C atom
δH
δC
1 2 3 4 4a 5 6 7
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