| Item type |
デフォルトアイテムタイプ_（フル）(1) |
| 公開日 |
2024-12-25 |
| タイトル |
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|
タイトル |
Detection of seco-macrotetrolides caused by regiospecific hydrolysis in Indonesian Streptomyces strains isolated at the karst area in Sulawesi Island |
|
言語 |
en |
| 作成者 |
Muslimin, Rukman
Ali, Alimuddin
Ogaki, Sho
Nurjannah
Alam, Ummu Kalsum
Choi, Sisun
Kim, Eung-Soo
Arakawa, Kenji
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| アクセス権 |
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アクセス権 |
embargoed access |
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アクセス権URI |
http://purl.org/coar/access_right/c_f1cf |
| 権利情報 |
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|
言語 |
en |
|
権利情報 |
© 2024. This manuscript version is made available under the CC-BY-NC-ND 4.0 license https://creativecommons.org/licenses/by-nc-nd/4.0/ |
| 権利情報 |
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言語 |
en |
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権利情報 |
This is not the published version. Please cite only the published version. |
| 権利情報 |
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言語 |
ja |
|
権利情報 |
この論文は出版社版ではありません。引用の際には出版社版をご確認、ご利用ください。 |
| 主題 |
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言語 |
en |
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主題Scheme |
Other |
|
主題 |
Endophytic streptomyces |
| 主題 |
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言語 |
en |
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主題Scheme |
Other |
|
主題 |
Sulawesi island |
| 主題 |
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言語 |
en |
|
主題Scheme |
Other |
|
主題 |
Macrotetrolides |
| 主題 |
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言語 |
en |
|
主題Scheme |
Other |
|
主題 |
Hydrolysis |
| 主題 |
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言語 |
en |
|
主題Scheme |
Other |
|
主題 |
Seco-acids |
| 内容記述 |
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|
内容記述 |
Among a total of 30 endophytic Streptomyces strains collected at the karst area in Sulawesi Island, Indonesia, four strains showed antimicrobial activity together with distinct purple-colored spot(s) on TLC after anisaldehyde staining and baking. Four endophytic strains AA004, AA010, AA034, and AA035 accumulated ionophore macrotetrolides (cyclic tetraesters) including nonactin, monactin, dinactin, trinactin, and tetranactin. Occasionally, strains AA034 and AA035 accumulated considerable amount of seco-macrotetrolides (ring-opened, linear macrotetrolides) including seco-dinactin, seco-monactin, and seco-trinactin, together with macrotetrolides as above mentioned. Time-course increase of seco-macrotetrolides indicates the subsequent hydrolysis of macrotetrolides. Seco-macrotetrolides in strain AA034 were separated from macrotetrolides and other metabolites through Sephadex LH20 and silica gel chromatographies, although seco-macrotetrolides contain inseparable five analogs. We here investigated the hydrolyzed positions in seco-macrotetrolides. ESI-CID-MS/MS analysis of seco-dinactin (m/z 805 as [M+Na]+) and its derivatives, methyl ester (m/z 819 as [M+Na]+) and O-acetyl methyl ester (m/z 861 as [M+Na]+), revealed that seco-dinactin obtained in strains AA034/AA035 is a single regioisomer with a cleavage at an ester bond between the alcohol of (−)-homononactate and the carboxylate of (+)-nonactate, suggesting the regioselective hydrolysis on the occurrence of seco-dinactin. Further ESI-CID-MS/MS analysis revealed that seco-monactin (m/z 791 as [M+Na]+) is also single regioisomer with the ester-bond cleavage between the alcohol of (−)-homononactate and the carboxylate of (+)-nonactate. In the case of seco-trinactin (m/z 819 as [M+Na]+), additional regioisomer with the ester-bond cleavage between the alcohol of (−)-homononactate and the carboxylate of (+)-homononactate was detected, together with the regioisomer with the ester-bond cleavage between the alcohol of (−)-homononactate and the carboxylate of (+)-nonactate. A mixture of seco-macrotetrolides exhibited no antimicrobial activity, indicating the importance of macrocyclic structure for antimicrobial activity. |
|
言語 |
en |
| 内容記述 |
|
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内容記述タイプ |
Other |
|
内容記述 |
This work was supported by Grants-in-Aid for Scientific Research (B) (No. 22H02274 to K.A.), and Fund for the Promotion of Joint International Research (Fostering Joint International Research (B) (No. 19KK0149 to K.A.) from Japan Society for the Promotion of Science (JSPS). Kenji Arakawa was supported by the JSPS Program for Fostering Globally Talented Researchers (No. JPMXS05S2900002). Alimuddin Ali was supported by the Ministry of Education and Culture, Indonesia, through DIPA Universitas Negeri Makassar (No. 570/UN36/HK/2022). Sisun Choi and Eung-Soo Kim were supported by the National Research Foundation in Korea (No. NRF-2021R1A2C2012203). Rukman Muslimin received a Scholarship for Research Students (Special Selection) from Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT), and Novice Lecture Fund DIKTI (Indonesia) 2022 and 2023 (Nos. 003/E5/PG.02.00/2022 and 185/E5/PG.02.00.PL/2023). This work was partly supported by a JSPS A3 Foresight Program (to S.C., E.-S.K., and K.A.). |
|
言語 |
en |
| 出版者 |
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出版者 |
Elsevier |
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言語 |
en |
| 言語 |
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言語 |
eng |
| 資源タイプ |
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資源タイプ識別子 |
http://purl.org/coar/resource_type/c_6501 |
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資源タイプ |
journal article |
| 出版タイプ |
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|
出版タイプ |
AM |
|
出版タイプResource |
http://purl.org/coar/version/c_ab4af688f83e57aa |
| 関連情報 |
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|
関連タイプ |
isVersionOf |
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識別子タイプ |
DOI |
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関連識別子 |
https://doi.org/10.1016/j.tet.2024.134045 |
| 助成情報 |
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助成機関名 |
日本学術振興会 |
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言語 |
ja |
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研究課題番号URI |
https://kaken.nii.ac.jp/ja/grant/KAKENHI-PROJECT-23K23541/ |
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研究課題番号 |
22H02274 |
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研究課題名 |
放線菌シグナル分子制御系の分子基盤解明および休眠二次代謝遺伝子の覚醒化 |
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言語 |
ja |
| 助成情報 |
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助成機関名 |
Japan Society for the Promotion of Science |
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言語 |
en |
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研究課題番号URI |
https://kaken.nii.ac.jp/ja/grant/KAKENHI-PROJECT-19KK0149/ |
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研究課題番号 |
19KK0149 |
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研究課題名 |
Elucidation of molecular basis of Streptomyces signaling-molecule-dependent regulatory pathway and activation of silent secondary metabolite biosynthetic genes |
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言語 |
en |
| 助成情報 |
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助成機関名 |
日本学術振興会 |
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言語 |
ja |
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研究課題名 |
多様な生態系を創出するインドネシア・スラウェシ島の天然資源調査と徹底的利活用 |
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言語 |
ja |
| 助成情報 |
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助成機関名 |
Japan Society for the Promotion of Science |
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言語 |
en |
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研究課題名 |
Exploring and extensive utilization of natural products in Sulawesi Island, Indonesia, creating the ecosystem diversity |
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言語 |
en |
| 開始ページ |
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開始ページ |
134045 |
| 書誌情報 |
en : Tetrahedron
巻 160,
p. 134045,
発行日 2024-05-18
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| 旧ID |
55902 |
| 備考 |
The full-text file will be made open to the public on 18 May 2026 in accordance with publisher's 'Terms and Conditions for Self-Archiving' |
Tetrahedron_160_134045.pdf (5.2 MB)
