Metabolite profile of Nectandra oppositifolia Nees & Mart. and assessment of antitrypanosomal activity of bioactive compounds through efficiency analyses

Geanne A. Alves Conserva; Luis M. Quirós-Guerrero; Thais A. Costa-Silva; Laurence Marcourt; Erika G. Pinto; Andre G. Tempone; João Paulo S. Fernandes; Jean-Luc Wolfender; Emerson F. Queiroz; João Henrique G. Lago

doi:10.1371/journal.pone.0247334

Peer Review History

Original SubmissionNovember 28, 2020
30 Dec 2020 Decision Letter - Branislav T. Šiler, Editor PONE-D-20-37405 Metabolite profile of Nectandra oppositifolia and assessment of the antitrypanosomal activity of bioactive compounds through efficiency analyses PLOS ONE Dear Dr. Lago, Thank you for submitting your manuscript to PLOS ONE. After careful consideration, we feel that it has merit but does not fully meet PLOS ONE’s publication criteria as it currently stands. Therefore, we invite you to submit a revised version of the manuscript that addresses the points raised during the review process. Several modifications of the text should be made according to the reviewers' suggestions. Please add the species authority (Nees & Mart.) in the main title and the first mention in the Introduction section. Language should be polished by a native English speaker (e.g. L55: a genus cannot possess, it can contain...). Please do not use genus abbreviations in figure captions and table titles; whole Latin names shoud be provided instead. Please submit your revised manuscript by Feb 12 2021 11:59PM. If you will need more time than this to complete your revisions, please reply to this message or contact the journal office at plosone@plos.org. When you're ready to submit your revision, log on to https://www.editorialmanager.com/pone/ and select the 'Submissions Needing Revision' folder to locate your manuscript file. Please include the following items when submitting your revised manuscript: A rebuttal letter that responds to each point raised by the academic editor and reviewer(s). You should upload this letter as a separate file labeled 'Response to Reviewers'. A marked-up copy of your manuscript that highlights changes made to the original version. You should upload this as a separate file labeled 'Revised Manuscript with Track Changes'. An unmarked version of your revised paper without tracked changes. You should upload this as a separate file labeled 'Manuscript'. If you would like to make changes to your financial disclosure, please include your updated statement in your cover letter. Guidelines for resubmitting your figure files are available below the reviewer comments at the end of this letter. If applicable, we recommend that you deposit your laboratory protocols in protocols.io to enhance the reproducibility of your results. Protocols.io assigns your protocol its own identifier (DOI) so that it can be cited independently in the future. For instructions see: http://journals.plos.org/plosone/s/submission-guidelines#loc-laboratory-protocols We look forward to receiving your revised manuscript. Kind regards, Branislav T. Šiler, Ph.D. Academic Editor PLOS ONE Journal Requirements: When submitting your revision, we need you to address these additional requirements. 1. Please ensure that your manuscript meets PLOS ONE's style requirements, including those for file naming. The PLOS ONE style templates can be found at https://journals.plos.org/plosone/s/file?id=wjVg/PLOSOne_formatting_sample_main_body.pdf and https://journals.plos.org/plosone/s/file?id=ba62/PLOSOne_formatting_sample_title_authors_affiliations.pdf 2. We noticed you have some minor occurrence of overlapping text with the following previous publications, which needs to be addressed: - https://www.sciencedirect.com/science/article/abs/pii/S0045206819315536?via%3Dihub - https://onlinelibrary.wiley.com/doi/abs/10.1002/elps.201900240 - https://www.mdpi.com/1660-3397/18/1/47/html - https://www.frontiersin.org/articles/10.3389/fpls.2020.01287/full In your revision ensure you cite all your sources (including your own works), and quote or rephrase any duplicated text. [Note: HTML markup is below. Please do not edit.] Reviewers' comments: Reviewer's Responses to Questions Comments to the Author 1. Is the manuscript technically sound, and do the data support the conclusions? The manuscript must describe a technically sound piece of scientific research with data that supports the conclusions. Experiments must have been conducted rigorously, with appropriate controls, replication, and sample sizes. The conclusions must be drawn appropriately based on the data presented. Reviewer #1: Yes Reviewer #2: Yes ******** 2. Has the statistical analysis been performed appropriately and rigorously? Reviewer #1: Yes Reviewer #2: Yes ****** 3. Have the authors made all data underlying the findings in their manuscript fully available? The PLOS Data policy requires authors to make all data underlying the findings described in their manuscript fully available without restriction, with rare exception (please refer to the Data Availability Statement in the manuscript PDF file). The data should be provided as part of the manuscript or its supporting information, or deposited to a public repository. For example, in addition to summary statistics, the data points behind means, medians and variance measures should be available. If there are restrictions on publicly sharing data—e.g. participant privacy or use of data from a third party—those must be specified. Reviewer #1: Yes Reviewer #2: Yes ****** 4. Is the manuscript presented in an intelligible fashion and written in standard English? PLOS ONE does not copyedit accepted manuscripts, so the language in submitted articles must be clear, correct, and unambiguous. Any typographical or grammatical errors should be corrected at revision, so please note any specific errors here. Reviewer #1: Yes Reviewer #2: Yes ****** 5. Review Comments to the Author Please use the space provided to explain your answers to the questions above. You may also include additional comments for the author, including concerns about dual publication, research ethics, or publication ethics. (Please upload your review as an attachment if it exceeds 20,000 characters) Reviewer #1: Introductive lines on potential of bioactive compounds and nutraceuticals should be adde d and related references added such as: Durazzo, A.; Lucarini, M.; Santini, A. Nutraceuticals in Human Health. Foods 2020, 9, 370. Lines 68-73 should be enlarged Data in Table 1 should be better described in the text Lines 367-373 shold be rewritten Lines 484-490 should be better discussed. Major details should be given in Tables 2, 3, 4, 5 Data in Figures 3 and 4 should be better described in the text Limits, advantages, practical applications should be added in a paragraph Conclusion The resolution of all Figures should be improved Reviewer #2: The paper entitled " Metabolite profile of Nectandra oppositifolia and assessment of the antitrypanosomal activity of bioactive compounds through efficiency analyses” describe the dereprication of the bioactive fractions and the isolation of 12 known compounds. Compounds 7 was the most active against T. cruzi, and derivates were synthesized and tested. Only few minor modifications are advised for acceptance: 1) Line 100, please correct the name of the city: Montluçon. 2) Line 360, please correct and of PI and NI data. 3) The quality of the figures 3 and 4 need to be improved. 4) Please add the position numbering on the structures to match the NMR data. ****** 6. PLOS authors have the option to publish the peer review history of their article (what does this mean?). If published, this will include your full peer review and any attached files. If you choose “no”, your identity will remain anonymous but your review may still be made public. Do you want your identity to be public for this peer review? For information about this choice, including consent withdrawal, please see our Privacy Policy. Reviewer #1: No Reviewer #2: Yes:** Ombeline Danton [NOTE: If reviewer comments were submitted as an attachment file, they will be attached to this email and accessible via the submission site. Please log into your account, locate the manuscript record, and check for the action link "View Attachments". If this link does not appear, there are no attachment files.] While revising your submission, please upload your figure files to the Preflight Analysis and Conversion Engine (PACE) digital diagnostic tool, https://pacev2.apexcovantage.com/. PACE helps ensure that figures meet PLOS requirements. To use PACE, you must first register as a user. Registration is free. Then, login and navigate to the UPLOAD tab, where you will find detailed instructions on how to use the tool. If you encounter any issues or have any questions when using PACE, please email PLOS at figures@plos.org. Please note that Supporting Information files do not need this step. https://doi.org/10.1371/journal.pone.0247334.r001
Revision 1
28 Jan 2021 Author Response EDITORIAL OFFICE COMMENTS 1. Please ensure that your manuscript meets PLOS ONE's style requirements, including those for file naming. The PLOS ONE style templates can be found at https://journals.plos.org/plosone/s/file?id=wjVg/PLOSOne_formatting_sample_main_body.pdf and https://journals.plos.org/plosone/s/file?id=ba62/PLOSOne_formatting_sample_title_authors_affiliations.pdf Thanks for your note – the revised version of this manuscript was adequately revised in order to meet the PLoS ONE style. 2. We noticed you have some minor occurrence of overlapping text with the following previous publications, which needs to be addressed: • https://www.sciencedirect.com/science/article/abs/pii/S0045206819315536?via%3Dihub • https://onlinelibrary.wiley.com/doi/abs/10.1002/elps.201900240 • https://www.mdpi.com/1660-3397/18/1/47/html • https://www.frontiersin.org/articles/10.3389/fpls.2020.01287/full Dear editor, thanks for this important note. As observed, these minor overlapping texts refer to Experimental Part, especially bioassays and efficient analysis. In your revision ensure you cite all your sources (including your own works), and quote or rephrase any duplicated text. The manuscript was carefully revised to avoid duplicated text and the references were adequately cited. REVIEW COMMENTS TO THE AUTHOR Reviewer #1 Introductive lines on potential of bioactive compounds and nutraceuticals should be added and related references added such as: Durazzo, A.; Lucarini, M.; Santini, A. Nutraceuticals in Human Health. Foods 2020, 9, 370. Thanks for your suggestion – this reference and related papers were added in the revised version of this manuscript. Lines 68-73 should be enlarged This sentence was modified accordingly. Data in Table 1 should be better described in the text More details concerning the analysis described in Table 1 were included in the revised version of this manuscript. Lines 367-373 should be rewritten These sentences were rewritten as suggested. Lines 484-490 should be better discussed. Thank you for this observation. This part of the manuscript was rephrased and the discussion was slightly modified. We hope that these modifications (highlighted in the revised version) had improved the discussion of this topic. Major details should be given in Tables 2, 3, 4, 5 Additional information on Tables 2 – 5 were included as suggested. Data in Figures 3 and 4 should be better described in the text ClassyFire allows chemists to perform large-scale, rapid and automated chemical classification. Moreover, the accessible API allows easy access to more than 77 million “ClassyFire” classified compounds. The results can be used to help annotate known compounds as performed in the present work. Using this approach, as detailed indicated in figure 3, nineteen different and known compounds (A – S) were putatively identified in the studied extracts. Attending your suggestion, one reference was included in this part to allow to reads how these analyses were performed. In the case of figure 4, additional information was included in the revised manuscript, as suggested by the referee. Limits, advantages, practical applications should be added in a paragraph Conclusion This sentence was modified accordingly as could be seen in the revised version of manuscript. The resolution of all Figures should be improved Attending your suggestion, the resolution of all figures was improved as could be seen in the revised version of the manuscript. Reviewer #2 The paper entitled "Metabolite profile of Nectandra oppositifolia and assessment of the antitrypanosomal activity of bioactive compounds through efficiency analyses” describe the dereplication of the bioactive fractions and the isolation of 12 known compounds. Compound 7 was the most active against T. cruzi, and derivatives were synthesized and tested. Only few minor modifications are advised for acceptance: 1) Line 100, please correct the name of the city: Montluçon. Thanks for your careful reading and corrections in the manuscript. This point was modified accordingly in the revised manuscript. 2) Line 360, please correct and of PI and NI data. Thanks again for your careful reading. This point corrected in the revised manuscript. 3) The quality of the figures 3 and 4 need to be improved. The quality of all figures was improved attending your suggestion. 4) Please add the position numbering on the structures to match the NMR data. Attending your suggestion, the structures of compounds 1 – 12 as well as the semisynthetic derivatives 7a – 7e, containing the position numbering, were included i Attachments Attachment Submitted filename: Response to Reviewers.docx https://doi.org/10.1371/journal.pone.0247334.r002
29 Jan 2021 Decision Letter - Branislav T. Šiler, Editor PONE-D-20-37405R1 Metabolite profile of Nectandra oppositifolia and assessment of the antitrypanosomal activity of bioactive compounds through efficiency analyses PLOS ONE Dear Dr. Lago, Thank you for submitting your manuscript to PLOS ONE. After careful consideration, we feel that it has merit but does not fully meet PLOS ONE’s publication criteria as it currently stands. Therefore, we invite you to submit a revised version of the manuscript that addresses the points raised during the review process. ============================== The authors failed to spot and to respond to my comments provided in the previous report: "Please add the species authority (Nees & Mart.) in the main title and the first mention in the Introduction section. Language should be polished by a native English speaker (e.g. L55: a genus cannot possess, it can contain...). Please do not use genus abbreviations in figure captions and table titles; whole Latin names shoud be provided instead." Table 1 header: "source" instead of "sourct" L565: "exhibited showed" - please remove one Language improvement is still highly recommended. ============================== Please submit your revised manuscript by Mar 15 2021 11:59PM. If you will need more time than this to complete your revisions, please reply to this message or contact the journal office at plosone@plos.org. When you're ready to submit your revision, log on to https://www.editorialmanager.com/pone/ and select the 'Submissions Needing Revision' folder to locate your manuscript file. Please include the following items when submitting your revised manuscript: A rebuttal letter that responds to each point raised by the academic editor and reviewer(s). You should upload this letter as a separate file labeled 'Response to Reviewers'. A marked-up copy of your manuscript that highlights changes made to the original version. You should upload this as a separate file labeled 'Revised Manuscript with Track Changes'. An unmarked version of your revised paper without tracked changes. You should upload this as a separate file labeled 'Manuscript'. If you would like to make changes to your financial disclosure, please include your updated statement in your cover letter. Guidelines for resubmitting your figure files are available below the reviewer comments at the end of this letter. If applicable, we recommend that you deposit your laboratory protocols in protocols.io to enhance the reproducibility of your results. Protocols.io assigns your protocol its own identifier (DOI) so that it can be cited independently in the future. For instructions see: http://journals.plos.org/plosone/s/submission-guidelines#loc-laboratory-protocols We look forward to receiving your revised manuscript. Kind regards, Branislav T. Šiler, Ph.D. Academic Editor PLOS ONE [Note: HTML markup is below. Please do not edit.] [NOTE: If reviewer comments were submitted as an attachment file, they will be attached to this email and accessible via the submission site. Please log into your account, locate the manuscript record, and check for the action link "View Attachments". If this link does not appear, there are no attachment files.] While revising your submission, please upload your figure files to the Preflight Analysis and Conversion Engine (PACE) digital diagnostic tool, https://pacev2.apexcovantage.com/. PACE helps ensure that figures meet PLOS requirements. To use PACE, you must first register as a user. Registration is free. Then, login and navigate to the UPLOAD tab, where you will find detailed instructions on how to use the tool. If you encounter any issues or have any questions when using PACE, please email PLOS at figures@plos.org. Please note that Supporting Information files do not need this step. https://doi.org/10.1371/journal.pone.0247334.r003
Revision 2
29 Jan 2021 Author Response Branislav T. Šiler, Ph.D. Academic Editor PLOS ONE Sao Paulo, January 29th, 2021 Dear Dr. Branislav T. Šiler, There is included here the revised version of the manuscript Metabolite profile of Nectandra oppositifolia (Nees & Mart.) and assessment of the antitrypanosomal activity of bioactive compounds through efficiency analyses to be analyzed for publication in PLOS ONE (PONE-D-20-37405). The authors thank the suggestions and corrections made in the manucript, and we sincerely hope that new alterations we have made, and the extra material that we have added in response to the points will be satisfactory for publication in PLOS ONE. Sincerely yours Prof. Dr. Joao Henrique G. Lago Attachments Attachment Submitted filename: Response to Reviewers.docx https://doi.org/10.1371/journal.pone.0247334.r004
2 Feb 2021 Decision Letter - Branislav T. Šiler, Editor PONE-D-20-37405R2 Metabolite profile of Nectandra oppositifolia (Nees & Mart.) and assessment of the antitrypanosomal activity of bioactive compounds through efficiency analyses PLOS ONE Dear Dr. Lago, Thank you for submitting your manuscript to PLOS ONE. After careful consideration, we feel that it has merit but does not fully meet PLOS ONE’s publication criteria as it currently stands. Therefore, we invite you to submit a revised version of the manuscript that addresses the points raised during the review process. ============================== The authors have considerably improved the language usage throughout the text. However, minor flaws have still remained: Species authority should not stand in brackets in the main title, L30 and L60 (please see e.g. http://www.plantsoftheworldonline.org/taxon/urn:lsid:ipni.org:names:281241-2). Delete "(L.)" from the L65. Genus names are commonly abbreviated with its first letter; therefore it does not need clarification. Please italicize the species Latin name in L215-216. L261: "Table 6 summarizes" instead of "Table 6 summarize". L548-550: The first sentence of the Conclusions section is vague, having poor syntax. Please rewrite to get sense. ============================== Please submit your revised manuscript by Mar 19 2021 11:59PM. If you will need more time than this to complete your revisions, please reply to this message or contact the journal office at plosone@plos.org. When you're ready to submit your revision, log on to https://www.editorialmanager.com/pone/ and select the 'Submissions Needing Revision' folder to locate your manuscript file. Please include the following items when submitting your revised manuscript: A rebuttal letter that responds to each point raised by the academic editor and reviewer(s). You should upload this letter as a separate file labeled 'Response to Reviewers'. A marked-up copy of your manuscript that highlights changes made to the original version. You should upload this as a separate file labeled 'Revised Manuscript with Track Changes'. An unmarked version of your revised paper without tracked changes. You should upload this as a separate file labeled 'Manuscript'. If you would like to make changes to your financial disclosure, please include your updated statement in your cover letter. Guidelines for resubmitting your figure files are available below the reviewer comments at the end of this letter. If applicable, we recommend that you deposit your laboratory protocols in protocols.io to enhance the reproducibility of your results. Protocols.io assigns your protocol its own identifier (DOI) so that it can be cited independently in the future. For instructions see: http://journals.plos.org/plosone/s/submission-guidelines#loc-laboratory-protocols We look forward to receiving your revised manuscript. Kind regards, Branislav T. Šiler, Ph.D. Academic Editor PLOS ONE [Note: HTML markup is below. Please do not edit.] [NOTE: If reviewer comments were submitted as an attachment file, they will be attached to this email and accessible via the submission site. Please log into your account, locate the manuscript record, and check for the action link "View Attachments". If this link does not appear, there are no attachment files.] While revising your submission, please upload your figure files to the Preflight Analysis and Conversion Engine (PACE) digital diagnostic tool, https://pacev2.apexcovantage.com/. PACE helps ensure that figures meet PLOS requirements. To use PACE, you must first register as a user. Registration is free. Then, login and navigate to the UPLOAD tab, where you will find detailed instructions on how to use the tool. If you encounter any issues or have any questions when using PACE, please email PLOS at figures@plos.org. Please note that Supporting Information files do not need this step. https://doi.org/10.1371/journal.pone.0247334.r005
Revision 3
4 Feb 2021 Author Response Dear Dr Anna Fodor PLOS ONE Recently, we received the following message from editorial office of PLOS ONE: Your manuscript files have been checked in-house but before we can proceed we need you to address the following issues: 1) Please upload a copy of Supporting Information Figures S71-270 which you refer to in your text in line 387 Its important to mention that there is a mistake in this sentence - the correct is "Figures S1 - S70", as indicated in the Supporting information file. Please, the manuscript was adequately modified as suggested. We sincerely hope that the new alterations we have made, and the extra material that we have added in response to the points raised by the referees, will be satisfactory for publication in PLOS ONE. Sincerely yours Dr. Joao H G Lago Attachments Attachment Submitted filename: Response to Reviewers.docx https://doi.org/10.1371/journal.pone.0247334.r006
5 Feb 2021 Decision Letter - Branislav T. Šiler, Editor Metabolite profile of Nectandra oppositifolia Nees & Mart. and assessment of the antitrypanosomal activity of bioactive compounds through efficiency analyses PONE-D-20-37405R3 Dear Dr. Lago, We’re pleased to inform you that your manuscript has been judged scientifically suitable for publication and will be formally accepted for publication once it meets all outstanding technical requirements. Within one week, you’ll receive an e-mail detailing the required amendments. When these have been addressed, you’ll receive a formal acceptance letter and your manuscript will be scheduled for publication. An invoice for payment will follow shortly after the formal acceptance. To ensure an efficient process, please log into Editorial Manager at http://www.editorialmanager.com/pone/, click the 'Update My Information' link at the top of the page, and double check that your user information is up-to-date. If you have any billing related questions, please contact our Author Billing department directly at authorbilling@plos.org. If your institution or institutions have a press office, please notify them about your upcoming paper to help maximize its impact. If they’ll be preparing press materials, please inform our press team as soon as possible -- no later than 48 hours after receiving the formal acceptance. Your manuscript will remain under strict press embargo until 2 pm Eastern Time on the date of publication. For more information, please contact onepress@plos.org. Kind regards, Branislav T. Šiler, Ph.D. Academic Editor PLOS ONE Additional Editor Comments (optional): Reviewers' comments: https://doi.org/10.1371/journal.pone.0247334.r007
Formally Accepted
9 Feb 2021 Acceptance Letter - Branislav T. Šiler, Editor PONE-D-20-37405R3 Metabolite profile of Nectandra oppositifolia Nees & Mart. and assessment of antitrypanosomal activity of bioactive compounds through efficiency analyses Dear Dr. Lago: I'm pleased to inform you that your manuscript has been deemed suitable for publication in PLOS ONE. Congratulations! Your manuscript is now with our production department. If your institution or institutions have a press office, please let them know about your upcoming paper now to help maximize its impact. If they'll be preparing press materials, please inform our press team within the next 48 hours. Your manuscript will remain under strict press embargo until 2 pm Eastern Time on the date of publication. For more information please contact onepress@plos.org. If we can help with anything else, please email us at plosone@plos.org. Thank you for submitting your work to PLOS ONE and supporting open access. Kind regards, PLOS ONE Editorial Office Staff on behalf of Dr. Branislav T. Šiler Academic Editor PLOS ONE https://doi.org/10.1371/journal.pone.0247334.r008

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