Bench to Any Side—The Pharmacology and Applications of Natural and Synthetic Alkylated Hydroxy Cinnamates and Cinnamides

Round 1

Reviewer 1 Report

Comments and Suggestions for Authors

The authors have done a very good piece of work, and presented the data obtained from the literature review in an interesting and understandable form. They brought the reader closer to the data on biological activity not only on natural alkylated hydroxy cinnamates, but also highlighted a large area of research related to the study of synthetic derivatives. In particular, they have devoted a lot of space to antioxidant activity, anticancer activity and treatment of neurodegenerative disorders, in addition to other important biological activities. The literature they used is up-to-date, about one-third of all cited references were published in the last four years (2023 – 5 refs, 2022 – 11 refs, 2021 – 13 refs, 2020 – 22 refs), in internationally recognized journals. I believe that the paper is qualified for publication in Compounds, but after the authors’ response to several issues.

Conclusions and perspectives: this section is too long, more like a discussion of the results than an actual identification of the most important findings from the literature review. The Conclusions should also not cite the literature. I suggest that the authors treat the Conclusions and perspectives chapter as a Discussion of the results, and rewrite Conclusions in a short and concise form.

Keywords: lack of p-coumaric acid.

All Abbreviations have been tabulated at the end of the manuscript. However, I believe that regardless, each abbreviation should be explained where it first appears.

References: full bibliographic data (mostly page numbers) are missing for the following publications – 5, 29, 39, 70, 94, 100, 111, 117, 122, 125, and 133.

Author Response

Reviewer 1-

• The authors have done a very good piece of work, and presented the data obtained from the literature review in an interesting and understandable form. They brought the reader closer to the data on biological activity not only on natural alkylated hydroxy cinnamates, but also highlighted a large area of research related to the study of synthetic derivatives. In particular, they have devoted a lot of space to antioxidant activity, anticancer activity and treatment of neurodegenerative disorders, in addition to other important biological activities. The literature they used is up-to-date, about one-third of all cited references were published in the last four years (2023 – 5 refs, 2022 – 11 refs, 2021 – 13 refs, 2020 – 22 refs), in internationally recognized journals. I believe that the paper is qualified for publication in Compounds, but after the authors’ response to several issues.

Response- We sincerely thank the reviewer for their positive comments and motivation for our work.

• Conclusions and perspectives: this section is too long, more like a discussion of the results than an actual identification of the most important findings from the literature review. The Conclusions should also not cite the literature. I suggest that the authors treat the Conclusions and perspectives chapter as a Discussion of the results, and rewrite Conclusions in a short and concise form.

Response- We have concluded each section in the sequence of its appearance in the text. Therefore, the conclusion section has resulted as voluminous.  We agree with the reviewer suggestion and accordingly we have modified the title to “Brief summary of the review results” followed by the short and concise conclusion section.

• Keywords: lack of p-coumaric acid.

Response- We thank the reviewer for the suggestion. Accordingly, we have added the keyword.

• All Abbreviations have been tabulated at the end of the manuscript. However, I believe that regardless, each abbreviation should be explained where it first appears.

Response- We thank the reviewer for the suggestion. Accordingly, we have added some of the abbreviation at the first place it appears in the text.  At other places we have explained the abbreviation where it first appears and the changes are highlighted. As most of these abbreviations are well-known, we hope the reviewer will agree to keep the same format at the end of the manuscript. We have removed the unused abbreviation from the list.

 

• References: full bibliographic data (mostly page numbers) are missing for the following publications – 5, 29, 39, 70, 94, 100, 111, 117, 122, 125, and 133.

Response- Although all of the references were automatically extracted from their respective downloaded RIS or Endnote files using Endnote software some of these errors have remained unnoticed. We thank the reviewer for pointing out these errors. Accordingly, the article numbers or page numbers were added and the revised contents are stated below.

Ref 5 – S. Liu, J. Jiang, Z. Ma, M. Xiao, L. Yang, B. Tian, Y. Yu, C. Bi, A. Fang, Y. Yang, The Role of Hydroxycinnamic Acid Amide Pathway in Plant Immunity, Frontiers in Plant Science, 13 (2022) Article 922119.

Ref 29- M. Martinez-Garcia, J. Gracia-Vitoria, K. Vanbroekhoven, W. Dejonghe, Y. Satyawali, Selective Enzymatic Esterification of Lignin-Derived Phenolics for the Synthesis of Lipophilic Antioxidants, Antioxidants, 12 (2023) 657.

 

Ref 39- I.G. Munteanu, C. Apetrei, Analytical Methods Used in Determining Antioxidant Activity: A Review, International Journal of Molecular Sciences, 22 (2021) 3380.

 

Ref 70- T.-H. Tsai, C.-H. Yu, Y.-P. Chang, Y.-T. Lin, C.-J. Huang, Y.-H. Kuo, P.-J. Tsai, Protective Effect of Caffeic Acid Derivatives on tert-Butyl Hydroperoxide-Induced Oxidative Hepato-Toxicity and Mitochondrial Dysfunction in HepG2 Cells, Molecules, 22 (2017) 702.

 

Ref 94- B. Michels, K. Franke, A. Weiglein, H. Sultani, B. Gerber, L.A. Wessjohann, Rewarding compounds identified from the medicinal plant Rhodiola rosea, Journal of Experimental Biology, 223 (2020) jeb223982.

 

Ref100- H. Luo, B. Saubamea, S. Chasseigneaux, V. Cochois, M. Smirnova, F. Glacial, N. Perrière, C. Chaves, S. Cisternino, X. Declèves, Molecular and Functional Study of Transient Receptor Potential Vanilloid 1-4 at the Rat and Human Blood–Brain Barrier Reveals Interspecies Differences, Frontiers in Cell and Developmental Biology, 8 (2020) Article 578514.

 

Ref 111- Y.-H. Shih, S.-M. Hsia, K.-C. Chiu, T.-H. Wang, C.-Y. Chien, P.-J. Li, Y.-H. Kuo, T.-M. Shieh, In Vitro Antimicrobial Potential of CAPE and Caffeamide Derivatives against Oral Microbes, International Journal of Molecular Sciences, 23 (2022) 4099.

 

Ref 117- W. Song, J. Xin, C. Yu, C. Xia, Y. Pan, Alkyl ferulic acid esters: Evaluating their structure and antibacterial properties, Frontiers in Microbiology, 14 (2023) 1135308.

Ref 122- S.P. Lopes, L.M. Yepes, Y. Pérez-Castillo, S.M. Robledo, D.P. de Sousa, Alkyl and Aryl Derivatives Based on p-Coumaric Acid Modification and Inhibitory Action against Leishmania braziliensis and Plasmodium falciparum, Molecules, 25 (2020) 3178.

Ref 125- S.P. Lopes, Y.P. Castillo, M.L. Monteiro, R.R.P.P.B.d. Menezes, R.N. Almeida, A.M.C. Martins, D.P.d. Sousa, Trypanocidal Mechanism of Action and in silico Studies of p-Coumaric Acid Derivatives, International Journal of Molecular Sciences, 20 (2019) 5916.

Ref 133- Y.C. Boo, p-Coumaric Acid as An Active Ingredient in Cosmetics: A Review Focusing on its Antimelanogenic Effects, Antioxidants, 8 (2019) 275.

Reviewer 2 Report

Comments and Suggestions for Authors

This manuscript titled Bench to any side- Pharmacology and applications of Natural and Synthetic Alkylated Hydroxy Cinnamates and Cinnamides”. The comments for this manuscript are as follows:

 

1.          There are some errors in the references. Every word in the title of references is capitalized, and the format is inconsistent. Please refer to the ²Instructions for Authors of the Journal². The authors are requested to check the entire manuscript carefully to avoid any errors.

2.          I did not see the author's statement in reference 31 that 10% (W/W) can be made into sun oil, sunscreen cream, lotion, hair spray, cologne, liquid foundation and anti-wrinkle cream. Is the author's quote correct? Although the authors emphasizes the sunscreen advantages of sinapoyl-L-malate, and many papers have indeed studied that sinapoyl-L-malate has good sunscreen activity. However, in fact, sinapoyl-L-malate is not currently added to the formula of sunscreen products. Could the authors explain what factors caused it ?

3.          There are many small errors in the text, such as numbers that exceed three digits and require a comma between each three digits. In addition, many places that should be superscripted are not superscripted. The author is asked to check carefully and correct them.

 

I decided it should be a minor revision.

Author Response

Reviewer 2-

This manuscript titled Bench to any side- Pharmacology and applications of Natural and Synthetic Alkylated Hydroxy Cinnamates and Cinnamides”. The comments for this manuscript are as follows:

 

1. There are some errors in the references. Every word in the title of references is capitalized, and the format is inconsistent. Please refer to the ²Instructions for Authors of the Journal². The authors are requested to check the entire manuscript carefully to avoid any errors.

Response- We sincerely thank the reviewer for their positive comments and motivation for our work. We have checked the manuscript and references for consistency. Most of the references were automatically extracted from their respective downloaded RIS or Endnote files using Endnote software.

 

2. I did not see the author's statement in reference 31 that 10% (W/W) can be made into sun oil, sunscreen cream, lotion, hair spray, cologne, liquid foundation and anti-wrinkle cream. Is the author's quote correct? Although the authors emphasizes the sunscreen advantages of sinapoyl-L-malate, and many papers have indeed studied that sinapoyl-L-malate has good sunscreen activity. However, in fact, sinapoyl-L-malate is not currently added to the formula of sunscreen products. Could the authors explain what factors caused it ?

Response- Reference 31 is the review article- N. Razzaghi-Asl, J. Garrido, H. Khazraei, F. Borges, O. Firuzi, Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships, Current Medicinal Chemistry, 20 (2013) 4436-4450 which does not discuss the above mentioned.

            Rather “structure 31 and the corresponding text “The UV absorption (λmax - 332 nm) and high molar absorptivity (ε 19800 M−1 cm−1) resulted in topical formulations of sun oil, sunscreen cream, lotion, hair spray, cologne, liquid foundation, anti-wrinkle cream which were prepared using upto 10% w/w of 31” was taken from reference 149 which is a patent document- H. Taniguchi, E. Nomura, T. Tsuno, S. Minami, Ferulic acid ester antioxidant/UV absorbent, in: E.P. Office (Ed.) EP0681825A2, Tsuno Food Industrial Co. Ltd, Japan, 1995. This was confirmed to be correct.

With reference to sinapoyl malate and its uses in sunscreens, we believe that currently the researchers studied sinapoyl malate as bio-based, safe, and natural skin product as an excellent alternative to substitute chemical filters in sunscreens in their paper. We feel that much more research may be required for the commercial application therefore we undertook the work of highlighting such projects.

 

3. There are many small errors in the text, such as numbers that exceed three digits and require a comma between each three digits. In addition, many places that should be superscripted are not superscripted. The author is asked to check carefully and correct them.

 Response- We thank the reviewer for pointing out these minor errors. Accordingly, we have added the commas between each three digits and the corrected text is highlighted. We have carefully checked the superscripted places and corrected them accordingly.

I decided it should be a minor revision.

Response – we thank the reviewer for their decision on our manuscript.