HPLC/ESI-MS and NMR Analysis of Chemical Constitutes in Bioactive Extract from the Root Nodule of <i>Vaccinium emarginatum</i>
<i>Vaccinium emarginatum</i> Hayata is a medicinal plant that has been historically used in ethnopharmacy to treat diseases in Taiwan. The objective of this study is to evaluate the anti-cancer and anti-bacterial constitutes from the root nodule extract of <i>V. emarginatum</i&g...
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MDPI AG
2021-10-01
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| Online Access: | https://www.mdpi.com/1424-8247/14/11/1098 |
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| author | Hsiang-Ming Huang Chien-Yi Ho Geng-Ruei Chang Wei-Yau Shia Cheng-Hung Lai Chih-Hao Chao Chao-Min Wang |
| author_facet | Hsiang-Ming Huang Chien-Yi Ho Geng-Ruei Chang Wei-Yau Shia Cheng-Hung Lai Chih-Hao Chao Chao-Min Wang |
| author_sort | Hsiang-Ming Huang |
| collection | DOAJ |
| description | <i>Vaccinium emarginatum</i> Hayata is a medicinal plant that has been historically used in ethnopharmacy to treat diseases in Taiwan. The objective of this study is to evaluate the anti-cancer and anti-bacterial constitutes from the root nodule extract of <i>V. emarginatum</i>. The chemical composition of <i>V. emarginatum</i> fractions was analyzed by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) and the chemical constitutes were isolated and structurally identified by nuclear magnetic resonance (NMR) spectroscopy. Bioassay-guided chromatography showed that the ethyl acetate (EA) fraction was bioactive on the hepatocellular carcinoma (HepG2). By LC-ESI-MS/MS analysis, twenty peaks of EA fraction were partially identified and the phytochemical investigation of the fractions led to the isolation and identification of protocatuchuic acid (<b>1</b>), epicatechin (<b>2</b>), catechin (<b>3</b>), procyanidin B3 (<b>4</b>), procyanidin A1 (<b>5</b>), hyperin (<b>6</b>), isoquercetin (<b>7</b>), quercetin (<b>8</b>), lupeol (<b>9</b>), beta-amyrin (<b>10</b>), and alpha-amyrin (<b>11</b>). Both procyanidin B3 and A1 exhibited anti-proliferative activity against HepG2 and gastric adenocarcinoma (AGS) cells at IC<sub>50</sub> values between 38.4 and 41.1 μM and 79.4 and 83.8 μM, respectively. In addition, isoquercetin displayed the strongest anti-proliferative activity against the HepG2, lung carcinoma (A549), and AGS cell at 18.7, 24.6 and 68.5 μM, respectively. Among the triterpenoids, only lupeol showed the inhibitory activity against all tested tumor cell lines at IC<sub>50</sub> values between 72.9 and 146.8 μM. Furthermore, procyanidins B3, A1 and isoquercetin displayed moderate anti-bacterial activity against <i>Staphylococcus aureus</i>. In conclusion, this study provides background information on the exploitation of <i>V. emarginatum</i> as a potential natural anti-cancer and anti-bacterial agent in pharmaceutical research. |
| first_indexed | 2024-03-10T05:10:13Z |
| format | Article |
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| language | English |
| last_indexed | 2024-03-10T05:10:13Z |
| publishDate | 2021-10-01 |
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| spelling | doaj.art-a5582054212b4c3ba3f178597d7f369b2023-11-23T00:55:11ZengMDPI AGPharmaceuticals1424-82472021-10-011411109810.3390/ph14111098HPLC/ESI-MS and NMR Analysis of Chemical Constitutes in Bioactive Extract from the Root Nodule of <i>Vaccinium emarginatum</i>Hsiang-Ming Huang0Chien-Yi Ho1Geng-Ruei Chang2Wei-Yau Shia3Cheng-Hung Lai4Chih-Hao Chao5Chao-Min Wang6Neurosurgery Department, China Medical University Hsinchu Hospital, Hsinchu 302, TaiwanDepartment of Biomedical Imaging and Radiological Science, China Medical University, Taichung 404, TaiwanDepartment of Veterinary Medicine, National Chiayi University, 580 Xinmin Road, Chiayi 600, TaiwanDepartment of Veterinary Medicine, National Chung-Hsing University, 145 XingDa Road, Taichung 402, TaiwanDepartment of Veterinary Medicine, National Chung-Hsing University, 145 XingDa Road, Taichung 402, TaiwanDivision of Chest Medicine, Attending Physician of Chang Bing Show Chwan Memorial Hospital, 6 Lugong Road, Lukang Township, Changhua 505, TaiwanDepartment of Veterinary Medicine, National Chiayi University, 580 Xinmin Road, Chiayi 600, Taiwan<i>Vaccinium emarginatum</i> Hayata is a medicinal plant that has been historically used in ethnopharmacy to treat diseases in Taiwan. The objective of this study is to evaluate the anti-cancer and anti-bacterial constitutes from the root nodule extract of <i>V. emarginatum</i>. The chemical composition of <i>V. emarginatum</i> fractions was analyzed by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) and the chemical constitutes were isolated and structurally identified by nuclear magnetic resonance (NMR) spectroscopy. Bioassay-guided chromatography showed that the ethyl acetate (EA) fraction was bioactive on the hepatocellular carcinoma (HepG2). By LC-ESI-MS/MS analysis, twenty peaks of EA fraction were partially identified and the phytochemical investigation of the fractions led to the isolation and identification of protocatuchuic acid (<b>1</b>), epicatechin (<b>2</b>), catechin (<b>3</b>), procyanidin B3 (<b>4</b>), procyanidin A1 (<b>5</b>), hyperin (<b>6</b>), isoquercetin (<b>7</b>), quercetin (<b>8</b>), lupeol (<b>9</b>), beta-amyrin (<b>10</b>), and alpha-amyrin (<b>11</b>). Both procyanidin B3 and A1 exhibited anti-proliferative activity against HepG2 and gastric adenocarcinoma (AGS) cells at IC<sub>50</sub> values between 38.4 and 41.1 μM and 79.4 and 83.8 μM, respectively. In addition, isoquercetin displayed the strongest anti-proliferative activity against the HepG2, lung carcinoma (A549), and AGS cell at 18.7, 24.6 and 68.5 μM, respectively. Among the triterpenoids, only lupeol showed the inhibitory activity against all tested tumor cell lines at IC<sub>50</sub> values between 72.9 and 146.8 μM. Furthermore, procyanidins B3, A1 and isoquercetin displayed moderate anti-bacterial activity against <i>Staphylococcus aureus</i>. In conclusion, this study provides background information on the exploitation of <i>V. emarginatum</i> as a potential natural anti-cancer and anti-bacterial agent in pharmaceutical research.https://www.mdpi.com/1424-8247/14/11/1098<i>Vaccinium emarginatum</i>anti-canceranti-bacterialprocyanidins |
| spellingShingle | Hsiang-Ming Huang Chien-Yi Ho Geng-Ruei Chang Wei-Yau Shia Cheng-Hung Lai Chih-Hao Chao Chao-Min Wang HPLC/ESI-MS and NMR Analysis of Chemical Constitutes in Bioactive Extract from the Root Nodule of <i>Vaccinium emarginatum</i> Pharmaceuticals <i>Vaccinium emarginatum</i> anti-cancer anti-bacterial procyanidins |
| title | HPLC/ESI-MS and NMR Analysis of Chemical Constitutes in Bioactive Extract from the Root Nodule of <i>Vaccinium emarginatum</i> |
| title_full | HPLC/ESI-MS and NMR Analysis of Chemical Constitutes in Bioactive Extract from the Root Nodule of <i>Vaccinium emarginatum</i> |
| title_fullStr | HPLC/ESI-MS and NMR Analysis of Chemical Constitutes in Bioactive Extract from the Root Nodule of <i>Vaccinium emarginatum</i> |
| title_full_unstemmed | HPLC/ESI-MS and NMR Analysis of Chemical Constitutes in Bioactive Extract from the Root Nodule of <i>Vaccinium emarginatum</i> |
| title_short | HPLC/ESI-MS and NMR Analysis of Chemical Constitutes in Bioactive Extract from the Root Nodule of <i>Vaccinium emarginatum</i> |
| title_sort | hplc esi ms and nmr analysis of chemical constitutes in bioactive extract from the root nodule of i vaccinium emarginatum i |
| topic | <i>Vaccinium emarginatum</i> anti-cancer anti-bacterial procyanidins |
| url | https://www.mdpi.com/1424-8247/14/11/1098 |
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