Two New Lactam Derivatives from <i>Micromelum falcatum</i> (Lour.) Tan. with Brine Shrimp Larvae Toxicity
Chemical investigation of the stems of <i>Micromelum falcatum</i> (Lour.) Tan. led to the isolation of two new lactam derivatives, named 3-(hydroxy(10-hydroxyphenyl)methyl)-4-(16-hydroxyphenyl)-1-methylpyrrolidin-2-one (<b>1</b>) and 3-(hydroxy(10-hydroxy-9-methoxyphenyl)meth...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-10-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/28/20/7157 |
| _version_ | 1797572747877941248 |
|---|---|
| author | Bin Liu Xiaobao Jin Xiaohong Chen Xin Wang Wenbo Zhang Xiongming Luo |
| author_facet | Bin Liu Xiaobao Jin Xiaohong Chen Xin Wang Wenbo Zhang Xiongming Luo |
| author_sort | Bin Liu |
| collection | DOAJ |
| description | Chemical investigation of the stems of <i>Micromelum falcatum</i> (Lour.) Tan. led to the isolation of two new lactam derivatives, named 3-(hydroxy(10-hydroxyphenyl)methyl)-4-(16-hydroxyphenyl)-1-methylpyrrolidin-2-one (<b>1</b>) and 3-(hydroxy(10-hydroxy-9-methoxyphenyl)methyl)-4-(16-hydroxyphenyl)-1-methylpyrrolidin-2-one (<b>2</b>), along with five known compounds, trans-4-hydroxycinnamic acid (<b>3</b>), 4-hydroxybenzaldehyde (<b>4</b>), m-hydroxybenzoic acid (<b>5</b>), p-hydroxybenzoic acid (<b>6</b>), and gallic acid (<b>7</b>). Their structures were determined on the basis of spectroscopic studies, including nuclear magnetic resonance (NMR) spectrum, mass spectrometry (MS) data, ultraviolet (UV) spectrum, infrared (IR) data, and comparison with the literature. All compounds were evaluated for toxicity against brine shrimp larvae and cytotoxicity to HeLa and HepG-2 cells. Compounds <b>1</b>–<b>2</b> exhibited moderate brine shrimp larvae toxicity with an LC<sub>50</sub> value of 50.6 and 121.8 μg mL<sup>−1</sup>, respectively. |
| first_indexed | 2024-03-10T21:00:14Z |
| format | Article |
| id | doaj.art-043cf8cb537946e6acd7bc7c231ab1e2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T21:00:14Z |
| publishDate | 2023-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-043cf8cb537946e6acd7bc7c231ab1e22023-11-19T17:33:33ZengMDPI AGMolecules1420-30492023-10-012820715710.3390/molecules28207157Two New Lactam Derivatives from <i>Micromelum falcatum</i> (Lour.) Tan. with Brine Shrimp Larvae ToxicityBin Liu0Xiaobao Jin1Xiaohong Chen2Xin Wang3Wenbo Zhang4Xiongming Luo5School of Life Sciences and Biopharmaceutics, Guangdong Pharmaceutical University, Guangzhou 510006, ChinaSchool of Life Sciences and Biopharmaceutics, Guangdong Pharmaceutical University, Guangzhou 510006, ChinaSchool of Life Sciences and Biopharmaceutics, Guangdong Pharmaceutical University, Guangzhou 510006, ChinaSchool of Basic Medical Sciences, Guangdong Pharmaceutical University, Guangzhou 510006, ChinaSchool of Life Sciences and Biopharmaceutics, Guangdong Pharmaceutical University, Guangzhou 510006, ChinaSchool of Life Sciences and Biopharmaceutics, Guangdong Pharmaceutical University, Guangzhou 510006, ChinaChemical investigation of the stems of <i>Micromelum falcatum</i> (Lour.) Tan. led to the isolation of two new lactam derivatives, named 3-(hydroxy(10-hydroxyphenyl)methyl)-4-(16-hydroxyphenyl)-1-methylpyrrolidin-2-one (<b>1</b>) and 3-(hydroxy(10-hydroxy-9-methoxyphenyl)methyl)-4-(16-hydroxyphenyl)-1-methylpyrrolidin-2-one (<b>2</b>), along with five known compounds, trans-4-hydroxycinnamic acid (<b>3</b>), 4-hydroxybenzaldehyde (<b>4</b>), m-hydroxybenzoic acid (<b>5</b>), p-hydroxybenzoic acid (<b>6</b>), and gallic acid (<b>7</b>). Their structures were determined on the basis of spectroscopic studies, including nuclear magnetic resonance (NMR) spectrum, mass spectrometry (MS) data, ultraviolet (UV) spectrum, infrared (IR) data, and comparison with the literature. All compounds were evaluated for toxicity against brine shrimp larvae and cytotoxicity to HeLa and HepG-2 cells. Compounds <b>1</b>–<b>2</b> exhibited moderate brine shrimp larvae toxicity with an LC<sub>50</sub> value of 50.6 and 121.8 μg mL<sup>−1</sup>, respectively.https://www.mdpi.com/1420-3049/28/20/7157<i>Micromelum falcatum</i> (Lour.) Tan.lactam derivativesbrine shrimp larvae |
| spellingShingle | Bin Liu Xiaobao Jin Xiaohong Chen Xin Wang Wenbo Zhang Xiongming Luo Two New Lactam Derivatives from <i>Micromelum falcatum</i> (Lour.) Tan. with Brine Shrimp Larvae Toxicity Molecules <i>Micromelum falcatum</i> (Lour.) Tan. lactam derivatives brine shrimp larvae |
| title | Two New Lactam Derivatives from <i>Micromelum falcatum</i> (Lour.) Tan. with Brine Shrimp Larvae Toxicity |
| title_full | Two New Lactam Derivatives from <i>Micromelum falcatum</i> (Lour.) Tan. with Brine Shrimp Larvae Toxicity |
| title_fullStr | Two New Lactam Derivatives from <i>Micromelum falcatum</i> (Lour.) Tan. with Brine Shrimp Larvae Toxicity |
| title_full_unstemmed | Two New Lactam Derivatives from <i>Micromelum falcatum</i> (Lour.) Tan. with Brine Shrimp Larvae Toxicity |
| title_short | Two New Lactam Derivatives from <i>Micromelum falcatum</i> (Lour.) Tan. with Brine Shrimp Larvae Toxicity |
| title_sort | two new lactam derivatives from i micromelum falcatum i lour tan with brine shrimp larvae toxicity |
| topic | <i>Micromelum falcatum</i> (Lour.) Tan. lactam derivatives brine shrimp larvae |
| url | https://www.mdpi.com/1420-3049/28/20/7157 |
| work_keys_str_mv | AT binliu twonewlactamderivativesfromimicromelumfalcatumilourtanwithbrineshrimplarvaetoxicity AT xiaobaojin twonewlactamderivativesfromimicromelumfalcatumilourtanwithbrineshrimplarvaetoxicity AT xiaohongchen twonewlactamderivativesfromimicromelumfalcatumilourtanwithbrineshrimplarvaetoxicity AT xinwang twonewlactamderivativesfromimicromelumfalcatumilourtanwithbrineshrimplarvaetoxicity AT wenbozhang twonewlactamderivativesfromimicromelumfalcatumilourtanwithbrineshrimplarvaetoxicity AT xiongmingluo twonewlactamderivativesfromimicromelumfalcatumilourtanwithbrineshrimplarvaetoxicity |