Isolation and Identification of <i>Cis-</i>2,5-Diketopiperazine from a Novel <i>Bacillus</i> Strain and Synthesis of Its Four Stereoisomers
The <i>Bacillus horneckiae</i>-like strain 2011SOCCUF3 was isolated from the marine sponge <i>Spongia officinalis</i> and its metabolome was studied for secondary metabolites with antimicrobial activity. Culturing in the presence of Diaion HP-20 resin and purifying the cultur...
Saved in:
| Main Authors: | , , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-05-01
|
| Series: | Marine Drugs |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1660-3397/23/6/234 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1849431511281958912 |
|---|---|
| author | Alan M. C. Obled Refaat B. Hamed Edward Spence Marija K. Zacharova Sunil V. Sharma Yunpeng Wang Rosemary Lynch Helen Connaris Adina Tatheer Marie-Lise Bourguet-Kondracki Gordon J. Florence Rebecca J. M. Goss |
| author_facet | Alan M. C. Obled Refaat B. Hamed Edward Spence Marija K. Zacharova Sunil V. Sharma Yunpeng Wang Rosemary Lynch Helen Connaris Adina Tatheer Marie-Lise Bourguet-Kondracki Gordon J. Florence Rebecca J. M. Goss |
| author_sort | Alan M. C. Obled |
| collection | DOAJ |
| description | The <i>Bacillus horneckiae</i>-like strain 2011SOCCUF3 was isolated from the marine sponge <i>Spongia officinalis</i> and its metabolome was studied for secondary metabolites with antimicrobial activity. Culturing in the presence of Diaion HP-20 resin and purifying the culture extract identified cyclo-phenylalanine-proline (cyclo-(Phe-Pro)), a 2,5-diketopiperazine (2,5-DKP), isolated as a major metabolite. Further, LCMS analysis of the extract showed the presence of two isomers of the molecule in the culture broth. To confirm the stereochemistry of the isomers observed in the natural extract, all four stereoisomers of cyclo-(Phe-Pro) were synthesised. NMR and LCMS studies identified the presence of both <i>cis-</i> and <i>trans</i>-cyclo-(Phe-Pro) isomers. Stability and epimerisation studies on synthetic isomers and the effect of culturing conditions suggested that the less stable <i>cis</i> isomer was naturally produced, which epimerised in culture broth. |
| format | Article |
| id | doaj-art-e1e10e64a54b4bb4a23ec616dcc96a02 |
| institution | Kabale University |
| issn | 1660-3397 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj-art-e1e10e64a54b4bb4a23ec616dcc96a022025-08-20T03:27:37ZengMDPI AGMarine Drugs1660-33972025-05-0123623410.3390/md23060234Isolation and Identification of <i>Cis-</i>2,5-Diketopiperazine from a Novel <i>Bacillus</i> Strain and Synthesis of Its Four StereoisomersAlan M. C. Obled0Refaat B. Hamed1Edward Spence2Marija K. Zacharova3Sunil V. Sharma4Yunpeng Wang5Rosemary Lynch6Helen Connaris7Adina Tatheer8Marie-Lise Bourguet-Kondracki9Gordon J. Florence10Rebecca J. M. Goss11School of Chemistry & BSRC, and Integrated Institute of Engineering, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKSchool of Chemistry & BSRC, and Integrated Institute of Engineering, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKSchool of Chemistry & BSRC, and Integrated Institute of Engineering, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKSchool of Chemistry & BSRC, and Integrated Institute of Engineering, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKSchool of Chemistry & BSRC, and Integrated Institute of Engineering, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKSchool of Chemistry & BSRC, and Integrated Institute of Engineering, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKSchool of Chemistry & BSRC, and Integrated Institute of Engineering, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKSchool of Chemistry & BSRC, and Integrated Institute of Engineering, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKSchool of Chemistry & BSRC, and Integrated Institute of Engineering, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKLaboratoire Molécules de Communication et Adaptation des Micro-Organismes, UMR 7245 CNRS, Muséum National d’Histoire Naturelle, 57 Rue Cuvier (C.P. 54), 75005 Paris, FranceSchool of Chemistry & BSRC, and Integrated Institute of Engineering, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKSchool of Chemistry & BSRC, and Integrated Institute of Engineering, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UKThe <i>Bacillus horneckiae</i>-like strain 2011SOCCUF3 was isolated from the marine sponge <i>Spongia officinalis</i> and its metabolome was studied for secondary metabolites with antimicrobial activity. Culturing in the presence of Diaion HP-20 resin and purifying the culture extract identified cyclo-phenylalanine-proline (cyclo-(Phe-Pro)), a 2,5-diketopiperazine (2,5-DKP), isolated as a major metabolite. Further, LCMS analysis of the extract showed the presence of two isomers of the molecule in the culture broth. To confirm the stereochemistry of the isomers observed in the natural extract, all four stereoisomers of cyclo-(Phe-Pro) were synthesised. NMR and LCMS studies identified the presence of both <i>cis-</i> and <i>trans</i>-cyclo-(Phe-Pro) isomers. Stability and epimerisation studies on synthetic isomers and the effect of culturing conditions suggested that the less stable <i>cis</i> isomer was naturally produced, which epimerised in culture broth.https://www.mdpi.com/1660-3397/23/6/234<i>Bacillus</i>marine sponge bacteriadiketopiperazinecyclopeptideantimicrobial |
| spellingShingle | Alan M. C. Obled Refaat B. Hamed Edward Spence Marija K. Zacharova Sunil V. Sharma Yunpeng Wang Rosemary Lynch Helen Connaris Adina Tatheer Marie-Lise Bourguet-Kondracki Gordon J. Florence Rebecca J. M. Goss Isolation and Identification of <i>Cis-</i>2,5-Diketopiperazine from a Novel <i>Bacillus</i> Strain and Synthesis of Its Four Stereoisomers Marine Drugs <i>Bacillus</i> marine sponge bacteria diketopiperazine cyclopeptide antimicrobial |
| title | Isolation and Identification of <i>Cis-</i>2,5-Diketopiperazine from a Novel <i>Bacillus</i> Strain and Synthesis of Its Four Stereoisomers |
| title_full | Isolation and Identification of <i>Cis-</i>2,5-Diketopiperazine from a Novel <i>Bacillus</i> Strain and Synthesis of Its Four Stereoisomers |
| title_fullStr | Isolation and Identification of <i>Cis-</i>2,5-Diketopiperazine from a Novel <i>Bacillus</i> Strain and Synthesis of Its Four Stereoisomers |
| title_full_unstemmed | Isolation and Identification of <i>Cis-</i>2,5-Diketopiperazine from a Novel <i>Bacillus</i> Strain and Synthesis of Its Four Stereoisomers |
| title_short | Isolation and Identification of <i>Cis-</i>2,5-Diketopiperazine from a Novel <i>Bacillus</i> Strain and Synthesis of Its Four Stereoisomers |
| title_sort | isolation and identification of i cis i 2 5 diketopiperazine from a novel i bacillus i strain and synthesis of its four stereoisomers |
| topic | <i>Bacillus</i> marine sponge bacteria diketopiperazine cyclopeptide antimicrobial |
| url | https://www.mdpi.com/1660-3397/23/6/234 |
| work_keys_str_mv | AT alanmcobled isolationandidentificationoficisi25diketopiperazinefromanovelibacillusistrainandsynthesisofitsfourstereoisomers AT refaatbhamed isolationandidentificationoficisi25diketopiperazinefromanovelibacillusistrainandsynthesisofitsfourstereoisomers AT edwardspence isolationandidentificationoficisi25diketopiperazinefromanovelibacillusistrainandsynthesisofitsfourstereoisomers AT marijakzacharova isolationandidentificationoficisi25diketopiperazinefromanovelibacillusistrainandsynthesisofitsfourstereoisomers AT sunilvsharma isolationandidentificationoficisi25diketopiperazinefromanovelibacillusistrainandsynthesisofitsfourstereoisomers AT yunpengwang isolationandidentificationoficisi25diketopiperazinefromanovelibacillusistrainandsynthesisofitsfourstereoisomers AT rosemarylynch isolationandidentificationoficisi25diketopiperazinefromanovelibacillusistrainandsynthesisofitsfourstereoisomers AT helenconnaris isolationandidentificationoficisi25diketopiperazinefromanovelibacillusistrainandsynthesisofitsfourstereoisomers AT adinatatheer isolationandidentificationoficisi25diketopiperazinefromanovelibacillusistrainandsynthesisofitsfourstereoisomers AT marielisebourguetkondracki isolationandidentificationoficisi25diketopiperazinefromanovelibacillusistrainandsynthesisofitsfourstereoisomers AT gordonjflorence isolationandidentificationoficisi25diketopiperazinefromanovelibacillusistrainandsynthesisofitsfourstereoisomers AT rebeccajmgoss isolationandidentificationoficisi25diketopiperazinefromanovelibacillusistrainandsynthesisofitsfourstereoisomers |