Chemopreventive agents from Physalis minima function as michael reaction acceptors
Ruizhi Men1, Ning Li1, Chihong Ding2, Yingzhan Tang1, Yachao Xing1, Wanjing Ding2, Zhongjun Ma2
1 School of Traditional Chinese Materia Medica; Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University), Ministry of Education, Wenhua Road 103, Shenyang 110016, PR China
2 Institute of Marine Biology, Ocean College, Zhejiang University, Zijingang Campus, No. 866 Yuhangtang Road, Hangzhou 310058, PR China
|Date of Submission||24-May-2015|
|Date of Decision||14-Jul-2015|
|Date of Web Publication||11-May-2016|
Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Wenhua Road 103, Shenyang 110016
Source of Support: None, Conflict of Interest: None
| Abstract|| |
Background: The fruits of some varieties of genus Physalis have been used as delicious fruits and functional food in the Northeast of China. Materials and Methods: To reveal the functional material basis, we performed bioactivity-guided phytochemical research and chemopreventive effect assay of the constituents from Physalis minima. Results: It was demonstrated that the ethyl acetate extract of P. minima L. (EEPM) had potential quinone reductase (QR) inducing activity with induction ratio (IR, QR induction activity) value of 1.47 ± 0.24, and glutathione binding property as potential Michael reaction acceptors (with an α, β-unsaturated ketone moiety). Furthermore, bioactivity-guided phytochemical research led eight compounds (1–8), which were elucidated as 3-isopropyl-5-acetoxycyclohexene-2-one-1 (1), isophysalin B (2), physalin G (3), physalin D (4), physalin I (5), physordinose B (6), stigmasterol-3-O-β-D-glucopyranoside (7) and 5α-6β-dihydroxyphysalin R (8) on the basis of nuclear magnetic resonance spectroscopy analyses and HRESIMS. Then, isophysalin B (2) and physordinose B (6) showed significant QR inducing activity with IR value of 2.80 ± 0.19 and 2.38 ± 0.46, respectively.
- An ultra.performance liquid chromatographic method with glutathione as the substrate was used to detect the Michael reaction acceptors in extracts of Physalis minima.(EPM)
- We investigated the chemical constituents of EPM guided by biological activity method
- Isophysalin B.(1) and physordinose B.(6) showed strong quinone reductase inducing activity with induction ratio values of 2.80±0.19 and 2.38±0.4
Abbreviations used: EPM: Extracts of Physalis minima, EEPM: Ethyl acetate extract of Physalis minima L., GSH: Glutathione, MRAs: Michael reaction acceptors, QR: Quinone reductase.
- This study generated useful information for consumers and many encourage researchers to utilize edible fruits from Physalis as a source of phytochemicals.
Keywords: Glutathione, Michael reaction acceptors, Physalis minima, Physalis, quinone reductase inducing activity
|How to cite this article:|
Men R, Li N, Ding C, Tang Y, Xing Y, Ding W, Ma Z. Chemopreventive agents from Physalis minima function as michael reaction acceptors. Phcog Mag 2016;12, Suppl S2:231-6
|How to cite this URL:|
Men R, Li N, Ding C, Tang Y, Xing Y, Ding W, Ma Z. Chemopreventive agents from Physalis minima function as michael reaction acceptors. Phcog Mag [serial online] 2016 [cited 2021 May 16];12, Suppl S2:231-6. Available from: http://www.phcog.com/text.asp?2016/12/46/231/182153
| Introduction|| |
The fruits of some varieties of genus Physalis have been used as delicious fruits and functional food in the Northeast of China. For example, the fruit of Physalis alkekengi has been used as a nutritious fruit as well as a treatment of aplastic anemia. And extractor infusions from Physalis have also been used in various countries in folk medicine as a treatment for different illnesses, such as spleen disorder, or as a tonic, diuretic, purgative, anticancer or anti-mycobacterial agent.
Quinone reductase (QR), a phase II enzyme, plays an important role in anticancer, detoxification pathways and antioxidant defense. It is currently included as a key member of a panel of in vitro bioassays directed toward the discovery of new plant-derived cancer chemopreventive agents. Many natural products have been found to have activities of inducing QR.,, The QR induction is regulated by the Keap1/Nrf2/ARE pathway in which Michael reaction acceptors (MRAs) (with α, β-unsaturated ketone moiety) can alkylate highly reactive cysteine residues in Keap1, and upregulate the expressions of phase II detoxifying enzymes, such as heme oxygenase 1 (HO -1), QR, and glutathione (GSH)-S-transferase.
In our previous studies on active constituents with QR inducing the activity of plants of the Solanaceae family,, with anolides isolated from Physalis angulata L. var. villosa Bonati could induce QR activity. As the plant from the same genus, Physalis minima L., which is widely distributed throughout tropical and subtropical regions of the world, had been investigated in this paper for the search of active constituents with QR inducing activity. An ultra-performance liquid chromatographic (UPLC) method with GSH as the substrate was used to detect the MRAs in the ethyl extract of P. minima L. (EEPM). The result revealed that the EEPM had electrophiles that could induce QR activity. Then, we investigated the chemical constituents of EEPM guided by biological activity method. Finally, eight compounds, 3-isopropyl-5-acetoxycyclohexene-2-one-1 (1), isophysalin B  (2), physalin G  (3), physalin D  (4), physalin I  (5) physordinose B  (6), stigmasterol-3-O-β-D-glucopyranoside  (7) and 5α-6β-dihydroxyphysalin R  (8), were isolated from the EEPM. QR induction activity was measured for these compounds to evaluate their cancer chemopreventive properties. In this paper, we described the isolation, structural elucidation, and the quinine reductase activity of these components.
| Materials and Methods|| |
A UPLC mass system (UPLC, Waters, Milford, MS, USA) and a Bridge Ethylidene Hybrid Particle C18 column (2.1 mm × 50 mm, 1.7 μm) were used to perform the chromatographic analysis. The high-performance liquid chromatography (HPLC) analysis was performed on Shimadzu HPLC (DGU-20A5 Degasser, LC-20AT Liquid Chromatograph, SIL-20AC Autosampler, SPD-M20A Diode Array Detector, CTO-20AC Column Oven) using Inerstil ODS-SP (5 μm, 4.6 mm × 250 mm) column. Preparative HPLC was performed on Beijing Chuangxintongheng LC3000 Semi-preparation Gradient HPLC System using Sepax Amethyst C-18 (5 μm, 21.2 × 250 mm) column. Ultraviolet (UV) spectra were recorded on a UV-2550 (PC) spectro photometer, Shimadzu Corporation. One- and two-dimensional nuclear magnetic resonance (NMR) experiments were performed on a Ultra shield Plus 400 MHz spectrometer (Bruker Corporation, Germany). Chemical shifts were referred to tetramethylsilane. J values were given in Hz. HR-ESIMS spectra detection was performed on a Micromass Quattro Premier Tandem Quadrupole Mass Spectrometer (Waters, Manchester, UK) using an electrospray ionization source in positive mode. Thin-layer chromatography was carried out on Qingdao Puke Sil G/UV254 plates of 0.25 thickness, and spots were visualized by spraying with 20% H2 SO4/EtOH followed by heating.
The whole plants of P. minima (3.3 kg dried weight) were collected in August 2011 in Guangzhou, Guangdong Province of China. The plant material was identified by Dr. Bo Yang (Zhejiang Chinese Medical University, China) and deposited at Zhejiang Chinese Medical University, under the acquisition number A20120923.
Ultra-performance liquid chromatographic method analysis of the ethyl acetate extract of Physalis minima L. reacted with glutathione
To analyze, we used UPLC with GSH as the substrate and we detected electrophiles in EEPM. The 20 mg of EEPM was suspended in methanol (1 mL). After centrifugal separation, 40 µL of supernatant was added to 360 µL of 5 mM GSH dissolved by 25 mM Tris-HCl buffer (pH 8.0). For another 40 µL, GSH was taken out as a control. Then they were both incubated at 37°C for 2 h. In the whole UPLC system, A (H2O) and B (CH3 CN) were used as the mobile phase. For EEPM, a gradient program was applied according to the following method: 0–3 min, 10–30% B, 3–5 min, 20–30% B, 5–7 min 30–45% B, 7–9 min 45–75% B, and 9–13 min 75–85% B. The injection volume was 1 µL with the flow rate of 0.5 mL/min, and the column and sample temperatures were maintained at 35°C and 25°C, respectively.
Extraction and isolation
The dried and powdered whole plants of P. minima (3.3 kg) were extracted with 95% EtOH under reflux 3 times (3 L × 10 L). Evaporation of the solvent under reduced pressure provided the ethanolic extract (240 g). The extract was dissolved and suspended in H2O (1.5 L), and then partitioned with petroleum ether (3 L × 1.5 L), EtOAc (3 L × 1.5 L), respectively, to yield petroleum ether extract (20.0 g) and ethyl acetate extract (65 g).
Approximately 60 g of the EEPM was subjected to column chromatography on silica gel (200–300 mesh, 130 cm × 8 cm, 600 g) gradiently eluted with petroleum ether/ethyl acetate (15:1, 10:1, 5:1, 3:1, 2:1, 1:1, 1:2, 0:1) to give 18 fractions (Fr.A–Fr.R). Fr.K (0.5 g) was subjected to preparative HPLC using MeOH/H2O as the mobile phase (0–50 min, 37%; 50–120 min, 45%; flow rate 10 mL/min) to yield 6 sub-fractions (Kfr 1–Kfr 6), Kfr. 5 was reseparated by preparative HPLC using 30% MeOH/H2O as the mobile phase (10 mL/min) to give compound 1 (7 mg, tR = 59.0 min). Fr.O (3.0 g) was first subjected to silica gel chromatography eluted with dichloromethane/methanol (from 1:0–0:1) yielding Ofr. 1–Ofr10. Ofr. 2 (170 mg) was purified by preparative HPLC using 57% MeOH–H2O (10 mL/min) to give compound 2 (25 mg). Ofr. 5 (210 mg) was separated by Sephadex LH-20 eluted with CH2 Cl2/MeOH (1:1) and preparative HPLC using 40% MeOH–H2O (10 mL/min) to afford compound 3 (50 mg). Ofr. 10 was purified over preparative HPLC with 40% MeOH–H2O to give compound 4 (50 mg, tR = 60.0 min). Fr.P (4.0 g) was first applied to silica gel chromatography eluted with CH2 Cl2/MeOH (50:1, 30:1, 20:1) to give Pfr. 1–Pfr. 9. Pfr. 1 was purified over preparative HPLC with 50% MeOH–H2O to give compound 5 (10 mg, tR = 64.0 min). Fr.Q (4.0 g) was first subjected to silica gel chromatography eluted with CH2 Cl2/MeOH (50:1, 30:1, 20:1, 15:1, 0:1) yielding Qfr. 1–Qfr. 12. Qfr. 10 was separated by preparative HPLC using MeOH/H2O as the mobile phase (0–35 min, 30–100%; 35–55%, 100%; flow rate 10 mL/min) to get sub-fractions Qfr. 10-A–I. Qfr. 10-F was further purified by preparative HPLC using MeOH/H2O as the mobile phase (0–35 min, 30–100%; 35–55%, 100%; flow rate 10 mL/min) to get compound 6 (30 mg, tR = 43.0 min) and compound 7 (54 mg, tR = 55.0 min). Qfr. 10-A was applied to preparative HPLC using 30% MeOH-H2O (10 mL/min) to afford compound 8 (45 mg).
Bioassay for cytotoxic activity and quinine reductase activity
R inducing activity was assessed using hepa 1c1c7 cells (obtained from ATCC). The cells were maintained in α-minimum essential medium supplemented with 0.1% penicillin-streptomycin, 10% fetal bovine serum (GIBCO, NY, USA) and incubated in 5% CO2 at 37°C. Hepa lclc7 cells were seeded in 96-well plates at a density of 1.0 × 105 cells/mL in 100 μL of media. After 24 h, the test compounds were added, and the cells were cultured for another 48 h. The medium was decanted, and the cells were incubated with 50 μL of 0.8% digitonin and 2 mM EDTA solution (pH 7.8) for 10 min at 37°C. Then, 200 μL of a mixed solution containing bovine serum albumin (0.67 mg/mL), 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (0.72 mM), 1.5% Tween 20, 0.5 M tris-HCl, 5 μM FAD, 150 mM glucose-6-phosphate, 2 units/mL glucose-6-phosphate dehydrogenase, 50 mM NADP, and 50 mM menadione were added into each well. After incubation for 3 min, the plates were scanned at 550 nm. Stock solution of the compound was dissolved in dimethyl sulfoxide (DMSO), and the final concentration of DMSO was kept at 0.5% (v/v). 4'-bromoflavone in DMSO and DMSO were used as the positive and negative control, respectively, and their final concentrations of DMSO were both kept at 0.5% (v/v). The cytotoxicity of the compound was determined by a crystal violet assay as previously described. Induction ratio (IR) = (ODNOQ1DrugGroup− ODNOQ1BlankGroup) (ODCrystalVioletSolventGroup− ODCrystalVioletBlankGroup)/(ODNOQ1SolventGroup− ODNOQ1BlankGroup) (ODCrystalVioletDrugGroup− ODCrystalVioletBlankGroup) × 100%. Experiments were carried out 3 times on separate occasions.
| Results and Discussion|| |
Ultra-performance liquid chromatographic method analysis of ethyl acetate extract of Physalis minima L. conjugated with glutathione
In [Figure 1], it was obvious that more than three peaks were weakened and three peaks disappeared by comparing UPLC chromatograms of EEPM before and after incubating with GSH, which suggested that the constituents disappeared or reduced might represent electrophiles to potentially induce QR activities as natural MARs. Among the eight compounds isolated from EEPM, compound 6 conjugated well with GSH. The UPLC chromatograms before and after incubated with GSH are shown in [Figure 2].
|Figure 1: UPLC fingerprinting of the ethyl acetate extract of Physalis minima L. (EEPM) before and after the combination with GSH (A: before, B: after)|
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|Figure 2: UPLC fingerprinting of compound 2 (isophysalin B) before and after the combination with GSH (A: before, B: after)|
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The EEPM of the whole plant of P. minima was subjected to repeated column chromatography and HPLC to afford eight compounds (1–8) [Figure 3]. They were identified as 3-isopropyl-5-acetoxycyclohexene-2-one-1 (1), isophysalin B (2), physalin G (3), physalin D (4), physalin I (5), physordinose B (6), stigmasterol-3-O-β-D-glucopyranoside (7) and 5α-6β-dihydroxyphysalin R (8) by analysis of spectral data.
White amorphous powder;1 H-NMR (400 MHz, CDCl3): δ 5.69 (1H, brs, H-2), δ1.97 (1H, m, H-4α), δ1.53 (1H, dd, J = 14.8, 3.8 Hz, H-4β), δ4.33 (1H, m, H-5), δ2.46 (1H, m, H-6α), δ1.78 (1H, dd, J = 13.2, 3.9 Hz, H-6β), δ1.60 (1H, br.s, H-7), δ 1.47 (3H, s, H-8), δ 1.27 (3H, s, H-9), δ 1.78 (3H, s, H-11);13 C NMR (100 MHz, CDCl3): 182.7 (C-1), 113.0 (C-2), 86.9 (C-3), 45.8 (C-4), 67.0 (C-5), 47.5 (C-6), 36.1 (C-7), 26.6 (C-8), 27.2 (C-9), 172.1 (C-10), 30.8 (C-11).
White needle crystal;1 H NMR (DMSO-d6, 400 MHz) [Table 1];13 C NMR (DMSO-d6, 100 MHz) [Table 3].
|Table 1: The 1H-NMR spectroscopic data of compounds 2, 3 and 4 (400 MHz, DMSO-d6) |
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Light yellow powder;1 H NMR (DMSO-d6, 400 MHz) [Table 1];13 C NMR (DMSO-d6, 100 MHz) [Table 3].
White amorphous powder;1 H NMR (DMSO-d6, 400 MHz) [Table 1];13 C NMR (DMSO-d6, 100 MHz) [Table 3].
White needle crystal; HREIMS [M + Na]+ m/z: 581.1978 (calcd for C29H34O11, 581.1999).1 H NMR (DMSO-d6, 400 MHz) [Table 2];13 C NMR (DMSO-d6, 100 MHz) [Table 3].
|Table 2: The 1H-NMR spectroscopic data of compounds 5 and 8 (400 MHz, DMSO-d6 or MeOD) |
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|Table 3: The 13C-NMR spectroscopic data of compounds 2, 3, 4, 5 and 8 (100 MHz for 13C, DMSO-d6 or MeOD) |
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Colorless oil;1 H NMR (DMSO-d6, 400 MHz): δ 5.40 (1H, m, H-1), δ 4.99 (1H, t, J = 4.9 Hz, H-2), δ 5.17 (1H, m, H-3), δ 4.54 (1H, m, H-5), δ 2.34 (1H, m, H-2” α), δ 2.24 (1H, m, H-2” β), δ 5.30 (1H, d, J = 8.0 Hz, H-3'), δ 1.25 (16H, br.s, CH2-5” -CH2-11” ), δ 0.88 (3H, t, J = 7 Hz, H-12'');13 C NMR (DMSO-d6, 100 MHz):.88.8 (C-1), 67.4 (C-2), 71.9 (C-3), 70.5 (C-4), 72.8 (C-5), 61.7 (C-6), 62.5 (C-1'), 103.2 (C-2'), 76.6 (C-3'), 71.8 (C-4'), 82.8 (C-5'), 59.9 (C-6'), 172.6 (Lauroyl O-2 C-1''), 33.4 (CH2-2'), 24.6 (CH2-3''), 28.6 (CH2-4''), 29.1 (CH2-5''-CH2-11''), 29.0 (CH2-5''-CH2-11''), 28.8 (CH2-5''-CH2-11''), 28.6 (CH2-5''-CH2-11''), 29.1 (CH2-5''-CH2-11''), 31.4 (CH2-5''-CH2-11''), 22.2 (CH2-5''-CH2-11''), 14.0 (CH3-12''), 175.1 (iBu-3 C-1'''), 33.5 (CH-C-2'''), 18.6 (CH3-C-3'''), 18.7 (CH3-C-4'''), 175.2 (iBu-3' C-1''''), 34.1 (CH-C-2''''), 15.8 (CH3-C-3''''), 18.9 (CH3-C-4'''').
White amorphous powder;1 H-NMR (400 MHz, DMSO-d6): δ 2.36 (1H, m, H-2α), δ2.13 (1H, t, J = 11.8 Hz, H-2 β), δ3.42 (1H, m, H-3α), δ2.88 (1H, m, H-4α), δ3.02 (1H, m, H-4 β), δ5.32 (1H, br. s, H-6), δ0.64 (3H, s, H-18), δ0.95 (3H, s, H-19), δ1.22 (3H, br.s, H-21), δ4.85 (1H, d, J = 5.0 Hz, H-22), δ 4.81 (1H, d, J = 5.0 Hz, H-23), δ 4.21 (1H, d, J = 7.8 Hz, H-1'), 2.90–3.66 (5H, m, H-Glc).13 C NMR (DMSO-d6, 100 MHz): 36.9 (C-1), 31.3 (C-2), 70.2 (C-3), 41.9 (C-4), 140.6 (C-5), 121.3 (C-6), 31.3 (C-7), 31.5 (C-8), 48.7 (C-9), 36.3 (C-10), 20.1 (C-11), 38.4 (C-12), 41.9 (C-13), 56.3 (C-14), 23.9 (C-15), 29.3 (C-16), 55.6 (C-17), 11.8 (C-18), 19.2 (C-19), 40.1 (C-20), 20.7 (C-21), 138.1 (C-22), 128.5 (C-23), 49.6 (C-24), 31.9 (C-25), 20.4 (C-26), 18.6 (C-27), 23.9 (C-28), 12.1 (C-29), 100.8 (C-1'), 76.8 (C-2'), 76.8 (C-3'), 70.2 (C-4'), 73.5 (C-5'), 61.2 (C-6').
White amorphous powder;1 H NMR (MeOD, 400 MHz) [Table 2];13 C NMR (MeOD, 100 MHz) [Table 3].
Quinone reductase induction activities of isolated compounds
As the EEPM of P. minima showed potential QR induction value of 1.47 ± 0.24 at the final concentration of 20 μg/mL, we measured the QR induction activity of constituents (1–8) isolated from the EEPM. In the in vitro bioactivity assay, compounds 2 (20 μM) and 6 (20 μM) showed strong QR inducing activity with IR value of 2.80 ± 0.19 and 2.38 ± 0.46, respectively, using 4-bromoflavone as a positive control substance (2.15 ± 0.09, 10 μg/mL) [Table 4].
|Table 4: Cytotoxic activities and quinine reductase activities of compounds 1-8 in hepa 1c1c7 cells |
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GSH conjugating results showed that compound 2 conjugated well with GSH, which was in agreement with the result of QR inducing assay.
| Conclusion|| |
The results showed that the UPLC method with GSH as the substrate could be used to detect the MRAs in extracts of P. minima. Isophysalin B (1) and physordinose B (6) showed strong QR inducing activity with IR value of 2.80 ± 0.19 and 2.38 ± 0.46. This study generated useful information for consumers and many encourage researchers to utilize edible fruits from Physalis as a source of phytochemicals.
The work was supported partially by National Natural Science Foundation of China (81173531), Fund for long-term training of young teachers in Shenyang Pharmaceutical University (ZCJJ2013409).
Financial support and sponsorship
Conflicts of interest
There are no conflicts of interest.
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| Authors|| |
Ning Li, Professor at the College of traditional Chinese medicine, Shenyang Pharmaceutical University. Her scientific interest includes isolate active ingredient and its quality control from traditional Chinese medicine and natural medicine
[Figure 1], [Figure 2], [Figure 3]
[Table 1], [Table 2], [Table 3], [Table 4]