Retusone A, a Guaiane-Type Sesquiterpene Dimer from <i>Wikstroemia retusa</i> and Its Inhibitory Effects on Histone Acetyltransferase HBO1 Expression
Retusone A (<b>1</b>), a new sesquiterpene dimer consisting of two guaiane-type sesquiterpenoids, and oleodaphnal (<b>2</b>) were isolated from heartwood of <i>Wikstroemia retusa</i> (Thymelaeaceae). The planar structure of <b>1</b> was elucidated on t...
| Main Authors: | , , , , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-05-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/9/2909 |
| _version_ | 1797503617798766592 |
|---|---|
| author | Young Sook Yun Tomomi Nakano Haruhiko Fukaya Yukio Hitotsuyanagi Miho Nakamura Megumi Umetsu Nobuko Matsushita Katsunori Miyake Hiroyuki Fuchino Nobuo Kawahara Fuki Moriya Akihiro Ito Yuji Takahashi Hideshi Inoue |
| author_facet | Young Sook Yun Tomomi Nakano Haruhiko Fukaya Yukio Hitotsuyanagi Miho Nakamura Megumi Umetsu Nobuko Matsushita Katsunori Miyake Hiroyuki Fuchino Nobuo Kawahara Fuki Moriya Akihiro Ito Yuji Takahashi Hideshi Inoue |
| author_sort | Young Sook Yun |
| collection | DOAJ |
| description | Retusone A (<b>1</b>), a new sesquiterpene dimer consisting of two guaiane-type sesquiterpenoids, and oleodaphnal (<b>2</b>) were isolated from heartwood of <i>Wikstroemia retusa</i> (Thymelaeaceae). The planar structure of <b>1</b> was elucidated on the basis of HRESIMS and NMR spectroscopic data, and the relative stereochemistry was established by X-ray diffraction analysis. The absolute configuration of <b>1</b> was determined by electronic circular dichroism. Compound <b>1</b> suppressed luciferase reporter gene expression driven by the HBO1 (histone acetyltransferase binding to ORC1) gene promoter in human breast cancer MCF7 cells. Compound <b>1</b> also decreased the expression of endogenous HBO1 mRNA and protein, and inhibited proliferation of the cells. These results suggest that retusone A (<b>1</b>), which has a unique dimeric sesquiterpenoid structure with inhibitory activity against HBO1 expression, may contribute to the development of a novel therapeutic candidate for the treatment of breast cancer. |
| first_indexed | 2024-03-10T03:53:16Z |
| format | Article |
| id | doaj.art-0140a809d82341d587eef62da21174ce |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:53:16Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0140a809d82341d587eef62da21174ce2023-11-23T08:51:27ZengMDPI AGMolecules1420-30492022-05-01279290910.3390/molecules27092909Retusone A, a Guaiane-Type Sesquiterpene Dimer from <i>Wikstroemia retusa</i> and Its Inhibitory Effects on Histone Acetyltransferase HBO1 ExpressionYoung Sook Yun0Tomomi Nakano1Haruhiko Fukaya2Yukio Hitotsuyanagi3Miho Nakamura4Megumi Umetsu5Nobuko Matsushita6Katsunori Miyake7Hiroyuki Fuchino8Nobuo Kawahara9Fuki Moriya10Akihiro Ito11Yuji Takahashi12Hideshi Inoue13School of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, JapanSchool of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, JapanSchool of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, JapanSchool of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, JapanSchool of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, JapanSchool of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, JapanSchool of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, JapanSchool of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, JapanResearch Center for Medicinal Plant Resources, National Institutes of Biomedical Innovation, Health and Nutrition, Tsukuba 305-0843, JapanResearch Center for Medicinal Plant Resources, National Institutes of Biomedical Innovation, Health and Nutrition, Tsukuba 305-0843, JapanSchool of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, JapanSchool of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, JapanSchool of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, JapanSchool of Life Sciences, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Tokyo 192-0392, JapanRetusone A (<b>1</b>), a new sesquiterpene dimer consisting of two guaiane-type sesquiterpenoids, and oleodaphnal (<b>2</b>) were isolated from heartwood of <i>Wikstroemia retusa</i> (Thymelaeaceae). The planar structure of <b>1</b> was elucidated on the basis of HRESIMS and NMR spectroscopic data, and the relative stereochemistry was established by X-ray diffraction analysis. The absolute configuration of <b>1</b> was determined by electronic circular dichroism. Compound <b>1</b> suppressed luciferase reporter gene expression driven by the HBO1 (histone acetyltransferase binding to ORC1) gene promoter in human breast cancer MCF7 cells. Compound <b>1</b> also decreased the expression of endogenous HBO1 mRNA and protein, and inhibited proliferation of the cells. These results suggest that retusone A (<b>1</b>), which has a unique dimeric sesquiterpenoid structure with inhibitory activity against HBO1 expression, may contribute to the development of a novel therapeutic candidate for the treatment of breast cancer.https://www.mdpi.com/1420-3049/27/9/2909<i>Wikstroemia retusa</i>Thymelaeaceaesesquiterpeneguaiane-typeHBO1breast cancer |
| spellingShingle | Young Sook Yun Tomomi Nakano Haruhiko Fukaya Yukio Hitotsuyanagi Miho Nakamura Megumi Umetsu Nobuko Matsushita Katsunori Miyake Hiroyuki Fuchino Nobuo Kawahara Fuki Moriya Akihiro Ito Yuji Takahashi Hideshi Inoue Retusone A, a Guaiane-Type Sesquiterpene Dimer from <i>Wikstroemia retusa</i> and Its Inhibitory Effects on Histone Acetyltransferase HBO1 Expression Molecules <i>Wikstroemia retusa</i> Thymelaeaceae sesquiterpene guaiane-type HBO1 breast cancer |
| title | Retusone A, a Guaiane-Type Sesquiterpene Dimer from <i>Wikstroemia retusa</i> and Its Inhibitory Effects on Histone Acetyltransferase HBO1 Expression |
| title_full | Retusone A, a Guaiane-Type Sesquiterpene Dimer from <i>Wikstroemia retusa</i> and Its Inhibitory Effects on Histone Acetyltransferase HBO1 Expression |
| title_fullStr | Retusone A, a Guaiane-Type Sesquiterpene Dimer from <i>Wikstroemia retusa</i> and Its Inhibitory Effects on Histone Acetyltransferase HBO1 Expression |
| title_full_unstemmed | Retusone A, a Guaiane-Type Sesquiterpene Dimer from <i>Wikstroemia retusa</i> and Its Inhibitory Effects on Histone Acetyltransferase HBO1 Expression |
| title_short | Retusone A, a Guaiane-Type Sesquiterpene Dimer from <i>Wikstroemia retusa</i> and Its Inhibitory Effects on Histone Acetyltransferase HBO1 Expression |
| title_sort | retusone a a guaiane type sesquiterpene dimer from i wikstroemia retusa i and its inhibitory effects on histone acetyltransferase hbo1 expression |
| topic | <i>Wikstroemia retusa</i> Thymelaeaceae sesquiterpene guaiane-type HBO1 breast cancer |
| url | https://www.mdpi.com/1420-3049/27/9/2909 |
| work_keys_str_mv | AT youngsookyun retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT tomominakano retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT haruhikofukaya retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT yukiohitotsuyanagi retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT mihonakamura retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT megumiumetsu retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT nobukomatsushita retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT katsunorimiyake retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT hiroyukifuchino retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT nobuokawahara retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT fukimoriya retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT akihiroito retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT yujitakahashi retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression AT hideshiinoue retusoneaaguaianetypesesquiterpenedimerfromiwikstroemiaretusaianditsinhibitoryeffectsonhistoneacetyltransferasehbo1expression |