Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells
Marinobazzanan (<b>1</b>), a new bazzanane-type sesquiterpenoid, was isolated from a marine-derived fungus belonging to the genus <i>Acremonium</i>. The chemical structure of <b>1</b> was elucidated using NMR and mass spectroscopic data, while the relative configu...
| Main Authors: | , , , , , , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-02-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/21/3/153 |
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| author | Sultan Pulat Prima F. Hillman Sojeong Kim Ratnakar N. Asolkar Haerin Kim Rui Zhou İsa Taş Chathurika D. B. Gamage Mücahit Varlı So-Yeon Park Sung Chul Park Inho Yang Jongheon Shin Dong-Chan Oh Hangun Kim Sang-Jip Nam William Fenical |
| author_facet | Sultan Pulat Prima F. Hillman Sojeong Kim Ratnakar N. Asolkar Haerin Kim Rui Zhou İsa Taş Chathurika D. B. Gamage Mücahit Varlı So-Yeon Park Sung Chul Park Inho Yang Jongheon Shin Dong-Chan Oh Hangun Kim Sang-Jip Nam William Fenical |
| author_sort | Sultan Pulat |
| collection | DOAJ |
| description | Marinobazzanan (<b>1</b>), a new bazzanane-type sesquiterpenoid, was isolated from a marine-derived fungus belonging to the genus <i>Acremonium</i>. The chemical structure of <b>1</b> was elucidated using NMR and mass spectroscopic data, while the relative configurations were established through the analysis of NOESY data. The absolute configurations of <b>1</b> were determined by the modified Mosher’s method as well as vibrational circular dichroism (VCD) spectra calculation and it was determined as 6<i>R</i>, 7<i>R</i>, 9<i>R</i>, and 10<i>R</i>. It was found that compound <b>1</b> was not cytotoxic to human cancer cells, including A549 (lung cancer), AGS (gastric cancer), and Caco-2 (colorectal cancer) below the concentration of 25 μM. However, compound <b>1</b> was shown to significantly decrease cancer-cell migration and invasion and soft-agar colony-formation ability at concentrations ranging from 1 to 5 μM by downregulating the expression level of KITENIN and upregulating the expression level of KAI1. Compound <b>1</b> suppressed β-catenin-mediated TOPFLASH activity and its downstream targets in AGS, A549, and Caco-2 and slightly suppressed the Notch signal pathway in three cancer cells. Furthermore, <b>1</b> also reduced the number of metastatic nodules in an intraperitoneal xenograft mouse model. |
| first_indexed | 2024-03-11T06:16:21Z |
| format | Article |
| id | doaj.art-7cf2938036544c699a748468918caf3b |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-11T06:16:21Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-7cf2938036544c699a748468918caf3b2023-11-17T12:17:15ZengMDPI AGMarine Drugs1660-33972023-02-0121315310.3390/md21030153Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer CellsSultan Pulat0Prima F. Hillman1Sojeong Kim2Ratnakar N. Asolkar3Haerin Kim4Rui Zhou5İsa Taş6Chathurika D. B. Gamage7Mücahit Varlı8So-Yeon Park9Sung Chul Park10Inho Yang11Jongheon Shin12Dong-Chan Oh13Hangun Kim14Sang-Jip Nam15William Fenical16College of Pharmacy and Research Institute of Life and Pharmaceutical Sciences, Sunchon National University, Sunchon 57922, Republic of KoreaDepartment of Chemistry and Nanoscience, Ewha Womans University, Seoul 03760, Republic of KoreaGraduate School of Industrial Pharmaceutical Sciences, Ewha Womans University, Seoul 03760, Republic of KoreaCenter for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California-San Diego, La Jolla, CA 92093-0204, USAGraduate School of Industrial Pharmaceutical Sciences, Ewha Womans University, Seoul 03760, Republic of KoreaCollege of Pharmacy and Research Institute of Life and Pharmaceutical Sciences, Sunchon National University, Sunchon 57922, Republic of KoreaCollege of Pharmacy and Research Institute of Life and Pharmaceutical Sciences, Sunchon National University, Sunchon 57922, Republic of KoreaCollege of Pharmacy and Research Institute of Life and Pharmaceutical Sciences, Sunchon National University, Sunchon 57922, Republic of KoreaCollege of Pharmacy and Research Institute of Life and Pharmaceutical Sciences, Sunchon National University, Sunchon 57922, Republic of KoreaCollege of Pharmacy and Research Institute of Life and Pharmaceutical Sciences, Sunchon National University, Sunchon 57922, Republic of KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 08826, Republic of KoreaDepartment of Convergence Study on the Ocean Science and Technology, Korea Maritime and Ocean University, Busan 49112, Republic of KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 08826, Republic of KoreaNatural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 08826, Republic of KoreaCollege of Pharmacy and Research Institute of Life and Pharmaceutical Sciences, Sunchon National University, Sunchon 57922, Republic of KoreaDepartment of Chemistry and Nanoscience, Ewha Womans University, Seoul 03760, Republic of KoreaCenter for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California-San Diego, La Jolla, CA 92093-0204, USAMarinobazzanan (<b>1</b>), a new bazzanane-type sesquiterpenoid, was isolated from a marine-derived fungus belonging to the genus <i>Acremonium</i>. The chemical structure of <b>1</b> was elucidated using NMR and mass spectroscopic data, while the relative configurations were established through the analysis of NOESY data. The absolute configurations of <b>1</b> were determined by the modified Mosher’s method as well as vibrational circular dichroism (VCD) spectra calculation and it was determined as 6<i>R</i>, 7<i>R</i>, 9<i>R</i>, and 10<i>R</i>. It was found that compound <b>1</b> was not cytotoxic to human cancer cells, including A549 (lung cancer), AGS (gastric cancer), and Caco-2 (colorectal cancer) below the concentration of 25 μM. However, compound <b>1</b> was shown to significantly decrease cancer-cell migration and invasion and soft-agar colony-formation ability at concentrations ranging from 1 to 5 μM by downregulating the expression level of KITENIN and upregulating the expression level of KAI1. Compound <b>1</b> suppressed β-catenin-mediated TOPFLASH activity and its downstream targets in AGS, A549, and Caco-2 and slightly suppressed the Notch signal pathway in three cancer cells. Furthermore, <b>1</b> also reduced the number of metastatic nodules in an intraperitoneal xenograft mouse model.https://www.mdpi.com/1660-3397/21/3/153marinobazzananbazzanane-type sesquiterpenoid<i>Acremonium</i> sp.cytotoxicityanticancer |
| spellingShingle | Sultan Pulat Prima F. Hillman Sojeong Kim Ratnakar N. Asolkar Haerin Kim Rui Zhou İsa Taş Chathurika D. B. Gamage Mücahit Varlı So-Yeon Park Sung Chul Park Inho Yang Jongheon Shin Dong-Chan Oh Hangun Kim Sang-Jip Nam William Fenical Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells Marine Drugs marinobazzanan bazzanane-type sesquiterpenoid <i>Acremonium</i> sp. cytotoxicity anticancer |
| title | Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells |
| title_full | Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells |
| title_fullStr | Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells |
| title_full_unstemmed | Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells |
| title_short | Marinobazzanan, a Bazzanane-Type Sesquiterpenoid, Suppresses the Cell Motility and Tumorigenesis in Cancer Cells |
| title_sort | marinobazzanan a bazzanane type sesquiterpenoid suppresses the cell motility and tumorigenesis in cancer cells |
| topic | marinobazzanan bazzanane-type sesquiterpenoid <i>Acremonium</i> sp. cytotoxicity anticancer |
| url | https://www.mdpi.com/1660-3397/21/3/153 |
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