Bioassay-guided isolation of cytotoxic constituents from the flowers of Aquilaria sinensis
Abstract Bioassay-guided fractionation of the EtOH extract from the flowers of Aquilaria sinensis (Lour.) Spreng. (Thymelaeaceae) led to the isolation of a new cucurbitane-type triterpenoid, aquilarolide A (1), along with five known compounds (2–6). The structure of 1 was elucidated by extensive 1D...
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| Format: | Article |
| Language: | English |
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SpringerOpen
2022-04-01
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| Series: | Natural Products and Bioprospecting |
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| Online Access: | https://doi.org/10.1007/s13659-022-00334-3 |
| _version_ | 1818774289905614848 |
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| author | Jun Yang Dong-Bao Hu Meng-Yuan Xia Ji-Feng Luo Xing-Yu Li Yue-Hu Wang |
| author_facet | Jun Yang Dong-Bao Hu Meng-Yuan Xia Ji-Feng Luo Xing-Yu Li Yue-Hu Wang |
| author_sort | Jun Yang |
| collection | DOAJ |
| description | Abstract Bioassay-guided fractionation of the EtOH extract from the flowers of Aquilaria sinensis (Lour.) Spreng. (Thymelaeaceae) led to the isolation of a new cucurbitane-type triterpenoid, aquilarolide A (1), along with five known compounds (2–6). The structure of 1 was elucidated by extensive 1D and 2D nuclear magnetic resonance (NMR) experiments and mass spectrometry (MS) data and theoretical calculations of its electronic circular dichroism (ECD) spectra. Aquilarolide A, cucurbitacin E (3), cucurbitacin B (4), and 7-hydroxy-6-methoxy-2-[2-(4-methoxyphenyl)ethyl]-4H-1-benzopyran-4-one (6) showed significant cytotoxicity against human lung adenocarcinoma SPC-A-1, human lung squamous cell carcinoma NCI-H520, human lung adenocarcinoma A549, and paclitaxel-resistant A549 (A549/Taxol) cell lines. All four active compounds, with IC50 values ranging from 0.002 to 0.91 μM, had better inhibitory activities against A549/Taxol cells than paclitaxel (IC50 = 1.80 μM). Among them, cucurbitacin E (IC50 = 0.002 μM) is the most active. Further studies are needed to evaluate their in vivo antitumor activities and to clarify their mechanisms. Graphical Abstract |
| first_indexed | 2024-12-18T10:38:47Z |
| format | Article |
| id | doaj.art-16d1652250ee4b9787b40dea430a2a12 |
| institution | Directory Open Access Journal |
| issn | 2192-2195 2192-2209 |
| language | English |
| last_indexed | 2024-12-18T10:38:47Z |
| publishDate | 2022-04-01 |
| publisher | SpringerOpen |
| record_format | Article |
| series | Natural Products and Bioprospecting |
| spelling | doaj.art-16d1652250ee4b9787b40dea430a2a122022-12-21T21:10:42ZengSpringerOpenNatural Products and Bioprospecting2192-21952192-22092022-04-011211910.1007/s13659-022-00334-3Bioassay-guided isolation of cytotoxic constituents from the flowers of Aquilaria sinensisJun Yang0Dong-Bao Hu1Meng-Yuan Xia2Ji-Feng Luo3Xing-Yu Li4Yue-Hu Wang5Key Laboratory of Economic Plants and Biotechnology and Yunnan Key Laboratory for Wild Plant Resources, Kunming Institute of Botany, Chinese Academy of SciencesSchool of Chemical Biology and Environment, Yuxi Normal UniversityKey Laboratory of Economic Plants and Biotechnology and Yunnan Key Laboratory for Wild Plant Resources, Kunming Institute of Botany, Chinese Academy of SciencesKey Laboratory of Economic Plants and Biotechnology and Yunnan Key Laboratory for Wild Plant Resources, Kunming Institute of Botany, Chinese Academy of SciencesCollege of Science, Yunnan Agricultural UniversityKey Laboratory of Economic Plants and Biotechnology and Yunnan Key Laboratory for Wild Plant Resources, Kunming Institute of Botany, Chinese Academy of SciencesAbstract Bioassay-guided fractionation of the EtOH extract from the flowers of Aquilaria sinensis (Lour.) Spreng. (Thymelaeaceae) led to the isolation of a new cucurbitane-type triterpenoid, aquilarolide A (1), along with five known compounds (2–6). The structure of 1 was elucidated by extensive 1D and 2D nuclear magnetic resonance (NMR) experiments and mass spectrometry (MS) data and theoretical calculations of its electronic circular dichroism (ECD) spectra. Aquilarolide A, cucurbitacin E (3), cucurbitacin B (4), and 7-hydroxy-6-methoxy-2-[2-(4-methoxyphenyl)ethyl]-4H-1-benzopyran-4-one (6) showed significant cytotoxicity against human lung adenocarcinoma SPC-A-1, human lung squamous cell carcinoma NCI-H520, human lung adenocarcinoma A549, and paclitaxel-resistant A549 (A549/Taxol) cell lines. All four active compounds, with IC50 values ranging from 0.002 to 0.91 μM, had better inhibitory activities against A549/Taxol cells than paclitaxel (IC50 = 1.80 μM). Among them, cucurbitacin E (IC50 = 0.002 μM) is the most active. Further studies are needed to evaluate their in vivo antitumor activities and to clarify their mechanisms. Graphical Abstracthttps://doi.org/10.1007/s13659-022-00334-3ThymelaeaceaeAquilaria sinensisPaclitaxel-resistant lung cancer cellsCucurbitane-type triterpenoids2-(2-Phenylethyl)chromones |
| spellingShingle | Jun Yang Dong-Bao Hu Meng-Yuan Xia Ji-Feng Luo Xing-Yu Li Yue-Hu Wang Bioassay-guided isolation of cytotoxic constituents from the flowers of Aquilaria sinensis Natural Products and Bioprospecting Thymelaeaceae Aquilaria sinensis Paclitaxel-resistant lung cancer cells Cucurbitane-type triterpenoids 2-(2-Phenylethyl)chromones |
| title | Bioassay-guided isolation of cytotoxic constituents from the flowers of Aquilaria sinensis |
| title_full | Bioassay-guided isolation of cytotoxic constituents from the flowers of Aquilaria sinensis |
| title_fullStr | Bioassay-guided isolation of cytotoxic constituents from the flowers of Aquilaria sinensis |
| title_full_unstemmed | Bioassay-guided isolation of cytotoxic constituents from the flowers of Aquilaria sinensis |
| title_short | Bioassay-guided isolation of cytotoxic constituents from the flowers of Aquilaria sinensis |
| title_sort | bioassay guided isolation of cytotoxic constituents from the flowers of aquilaria sinensis |
| topic | Thymelaeaceae Aquilaria sinensis Paclitaxel-resistant lung cancer cells Cucurbitane-type triterpenoids 2-(2-Phenylethyl)chromones |
| url | https://doi.org/10.1007/s13659-022-00334-3 |
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