Cytotoxicity against HL60 Cells of Ficifolidione Derivatives with Methyl, <i>n</i>-Pentyl, and <i>n</i>-Heptyl Groups
Ficifolidione, a natural insecticidal compound isolated from the essential oils of Myetaceae species, is a spiro phloroglucinol with an isobutyl group at the C-4 position. We found that ficifolidione showed cytotoxicity against cancer cells via apoptosis. Replacement of the isobutyl group by <i&g...
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MDPI AG
2019-11-01
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| Online Access: | https://www.mdpi.com/1420-3049/24/22/4081 |
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| author | Hisashi Nishiwaki Megumi Ikari Satomi Fujiwara Kosuke Nishi Takuya Sugahara Koichi Akiyama Satoshi Yamauchi |
| author_facet | Hisashi Nishiwaki Megumi Ikari Satomi Fujiwara Kosuke Nishi Takuya Sugahara Koichi Akiyama Satoshi Yamauchi |
| author_sort | Hisashi Nishiwaki |
| collection | DOAJ |
| description | Ficifolidione, a natural insecticidal compound isolated from the essential oils of Myetaceae species, is a spiro phloroglucinol with an isobutyl group at the C-4 position. We found that ficifolidione showed cytotoxicity against cancer cells via apoptosis. Replacement of the isobutyl group by <i>n</i>-propyl group did not influence the potency, but the effect of the replacement of this group by a shorter or longer alkyl group on the biological activity remains unknown. In this study, ficifolidione derivatives with alkyl groups such as methyl, <i>n</i>-pentyl, and <i>n</i>-heptyl group—instead of the isobutyl group at the C-4 position—were synthesized to evaluate their cytotoxicity against the human promyelocytic leukaemia cell line HL60 and their insecticidal activity against mosquito larvae. The biological activities of their corresponding 4-epimers were also evaluated. As a result, the conversion of the isobutyl group to another alkyl group did not significantly influence the cytotoxicity or insecticidal activity. In HL60 cells treated with the <i>n</i>-heptyl-ficifolidione derivative, the activation of caspase 3/7 and the early stages of apoptosis were detected by using immunofluorescence and flow cytometric techniques, respectively, suggesting that the cytotoxicity should be induced by apoptosis even though the alkyl group was changed. |
| first_indexed | 2024-12-17T07:39:24Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-17T07:39:24Z |
| publishDate | 2019-11-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-fec8487cb3da4519835b1a2ed4533e3d2022-12-21T21:58:12ZengMDPI AGMolecules1420-30492019-11-012422408110.3390/molecules24224081molecules24224081Cytotoxicity against HL60 Cells of Ficifolidione Derivatives with Methyl, <i>n</i>-Pentyl, and <i>n</i>-Heptyl GroupsHisashi Nishiwaki0Megumi Ikari1Satomi Fujiwara2Kosuke Nishi3Takuya Sugahara4Koichi Akiyama5Satoshi Yamauchi6Graduate School of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, JapanGraduate School of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, JapanGraduate School of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, JapanGraduate School of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, JapanGraduate School of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, JapanADRES Tarumi station, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, JapanGraduate School of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, JapanFicifolidione, a natural insecticidal compound isolated from the essential oils of Myetaceae species, is a spiro phloroglucinol with an isobutyl group at the C-4 position. We found that ficifolidione showed cytotoxicity against cancer cells via apoptosis. Replacement of the isobutyl group by <i>n</i>-propyl group did not influence the potency, but the effect of the replacement of this group by a shorter or longer alkyl group on the biological activity remains unknown. In this study, ficifolidione derivatives with alkyl groups such as methyl, <i>n</i>-pentyl, and <i>n</i>-heptyl group—instead of the isobutyl group at the C-4 position—were synthesized to evaluate their cytotoxicity against the human promyelocytic leukaemia cell line HL60 and their insecticidal activity against mosquito larvae. The biological activities of their corresponding 4-epimers were also evaluated. As a result, the conversion of the isobutyl group to another alkyl group did not significantly influence the cytotoxicity or insecticidal activity. In HL60 cells treated with the <i>n</i>-heptyl-ficifolidione derivative, the activation of caspase 3/7 and the early stages of apoptosis were detected by using immunofluorescence and flow cytometric techniques, respectively, suggesting that the cytotoxicity should be induced by apoptosis even though the alkyl group was changed.https://www.mdpi.com/1420-3049/24/22/4081phloroglucinolficifolidionehl60cytotoxicity |
| spellingShingle | Hisashi Nishiwaki Megumi Ikari Satomi Fujiwara Kosuke Nishi Takuya Sugahara Koichi Akiyama Satoshi Yamauchi Cytotoxicity against HL60 Cells of Ficifolidione Derivatives with Methyl, <i>n</i>-Pentyl, and <i>n</i>-Heptyl Groups Molecules phloroglucinol ficifolidione hl60 cytotoxicity |
| title | Cytotoxicity against HL60 Cells of Ficifolidione Derivatives with Methyl, <i>n</i>-Pentyl, and <i>n</i>-Heptyl Groups |
| title_full | Cytotoxicity against HL60 Cells of Ficifolidione Derivatives with Methyl, <i>n</i>-Pentyl, and <i>n</i>-Heptyl Groups |
| title_fullStr | Cytotoxicity against HL60 Cells of Ficifolidione Derivatives with Methyl, <i>n</i>-Pentyl, and <i>n</i>-Heptyl Groups |
| title_full_unstemmed | Cytotoxicity against HL60 Cells of Ficifolidione Derivatives with Methyl, <i>n</i>-Pentyl, and <i>n</i>-Heptyl Groups |
| title_short | Cytotoxicity against HL60 Cells of Ficifolidione Derivatives with Methyl, <i>n</i>-Pentyl, and <i>n</i>-Heptyl Groups |
| title_sort | cytotoxicity against hl60 cells of ficifolidione derivatives with methyl i n i pentyl and i n i heptyl groups |
| topic | phloroglucinol ficifolidione hl60 cytotoxicity |
| url | https://www.mdpi.com/1420-3049/24/22/4081 |
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