Startseite Chemical composition and the anti-inflammatory effect of volatile compounds from Anaxagorea luzonensis A. Gray
Artikel
Lizenziert
Nicht lizenziert Erfordert eine Authentifizierung

Chemical composition and the anti-inflammatory effect of volatile compounds from Anaxagorea luzonensis A. Gray

  • Gia Buu Tran , Ty Viet Pham ORCID logo , Anh Tuan Le , Nguyen Hoai Nguyen , Nguyen Huy Hoang Vo und Bich Hang Do EMAIL logo
Veröffentlicht/Copyright: 14. Juni 2024
Veröffentlichen auch Sie bei De Gruyter Brill

Abstract

Anaxagorea luzonensis A. Gray, a member of the Annonaceae family, has been used to treat a variety of illnesses for a long time. For the first time, A. luzonensis volatile compounds (ALVCs) were extracted from the leaves, and the components were identified using gas chromatography-mass spectrometry (GC-MS). Further, the main compositions of ALVCs were also assessed for their ability to bind with anti-inflammatory proteins using a docking model. In addition, in vitro tests e.g. inhibition of protein degradation and the inhibition of nitric oxide release using RAW264.7 macrophage cells were utilized for evaluating the anti-inflammatory activity. The results showed that the principal compounds of ALVCs were bulnesol (34.1 %), cubitene (17.8 %), β-eudesmol (10.4 %), epi-longipinanol (5.9 %), and (Z)-nerolidyl acetate (5.5 %). Three compounds viz. bulnesol, cubitene, and β-eudesmol bound firmly to cyclooxygenase-1 (COX-1), cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX), as shown by the in silico analysis, similar to the positive control diclofenac. ALVCs effectively inhibited protein degradation with the IC50 of 31 ± 2.3 μg/mL and inhibited nitric oxide production with the IC50 of 43.30 ± 3.37 μg/mL. These findings showed that ALVCs might have a promising anti-inflammatory effect by blocking several inflammatory proteins.


Corresponding author: Bich Hang Do, Faculty of Pharmacy, Ton Duc Thang University, Ho Chi Minh City, Vietnam, E-mail:

Funding source: Ton Duc Thang University

Award Identifier / Grant number: 3633/QD-TDT 19/12/2022

Acknowledgments

The authors would like express their gratitude to Dr. Thien-Y Vu, Faculty of Pharmacy, Ton Duc Thang University, Vietnam for his support in docking study of the research project.

  1. Research ethics: Not applicable.

  2. Author contributions: Conceptualization and experiment design: Gia Buu Tran, Ty Viet Pham, Anh Tuan Le, Hoai Nguyen Nguyen, Nguyen Huy Hoang Vo, Bich Hang Do. Data curation & visualization: Huy Hoang Nguyen Vo, Gia Buu Tran, Bich Hang Do. Formal analysis: Anh Tuan Le, Hoai Nguyen Nguyen, Bich Hang Do. Writing-original draft: Ty Viet Pham, Anh Tuan Le, Hoai Nguyen Nguyen, Nguyen Huy Hoang Vo, Gia Buu Tran, Bich Hang Do. Review-editing: Bich Hang Do. The authors have accepted responsibility for the entire content of this manuscript and approved its submission.

  3. Competing interests: The authors state no conflict of interest.

  4. Research funding: This work was supported by Ton Duc Thang University under (3633/QD-TDT 19/12/2022).

  5. Data availability: The raw data can be obtained on a reasonable request from the corresponding author.

References

1. Furman, D, Campisi, J, Verdin, E, Carrera-Bastos, P, Targ, S, Franceschi, C, et al.. Chronic inflammation in the etiology of disease across the life span. Nat Med 2019;25:1822–32. https://doi.org/10.1038/s41591-019-0675-0.Suche in Google Scholar PubMed PubMed Central

2. Vonkeman, HE, van de Laar, MAFJ. Nonsteroidal anti-inflammatory drugs: adverse effects and their prevention. Semin Arthritis Rheum 2010;39:294–312. https://doi.org/10.1016/j.semarthrit.2008.08.001.Suche in Google Scholar PubMed

3. Riaz, M, Khalid, R, Afzal, M, Anjum, F, Fatima, H, Zia, S, et al.. Phytobioactive compounds as therapeutic agents for human diseases: a review. In: Food science and nutrition. John Wiley and Sons Inc; 2023, vol 11:2500–29 pp.10.1002/fsn3.3308Suche in Google Scholar PubMed PubMed Central

4. Proestos, C. The benefits of plant extracts for human health. In: Foods. Basel: MDPI; 2020, 9.10.3390/foods9111653Suche in Google Scholar PubMed PubMed Central

5. Miguel, M. Antioxidant and anti-inflammatory activities of essential oils: a short review. Molecules 2010;15:9252–87. https://doi.org/10.3390/molecules15129252.Suche in Google Scholar PubMed PubMed Central

6. Chouhan, S, Sharma, K, Guleria, S. Antimicrobial activity of some essential oils – present status and future perspectives. Medicine 2017;4:58. https://doi.org/10.3390/medicines4030058.Suche in Google Scholar PubMed PubMed Central

7. Blowman, K, Magalhães, M, Lemos, MFL, Cabral, C, Pires, IM. Anticancer properties of essential oils and other natural products. Dudai N, editor. Evid base Compl Alternative Med 2018;2018:3149362. https://doi.org/10.1155/2018/3149362.Suche in Google Scholar PubMed PubMed Central

8. Zuo, X, Gu, Y, Wang, C, Zhang, J, Zhang, J, Wang, G, et al.. A systematic review of the anti-inflammatory and immunomodulatory properties of 16 essential oils of herbs. Cuman RKN, editor. Evid Based Complement Alternat Med 2020;2020:8878927. https://doi.org/10.1155/2020/8878927.Suche in Google Scholar PubMed PubMed Central

9. Gonda, R, Takeda, T, Akiyama, T. Studies on the constituents of Anaxagorea iuzonensis A. Gray. Chem Pharm Bull 2000;48:1219–22. https://doi.org/10.1248/cpb.48.1219.Suche in Google Scholar PubMed

10. Tep-areenan, P, Wetchasit, P, Sawasdee, P. Extracted Anaxagorea luzonensis A Gray restored impairment of endothelium-dependent vasorelaxation induced by homocysteine thiolactone in rat aortic rings. J Med Assoc Thai. 2015;98:S31-7.Suche in Google Scholar

11. Pham, T, Van, T, Dang, N, Vo, QH, Ho, D. Chemical composition of the essential oils of Distichochlamys citrea leaves collected from central Vietnam. Vietnam J Chem 2017;55:358–62.Suche in Google Scholar

12. Pham, TV, Ngo, HPT, Thi, TDN, Khoa Nguyen, H, Thi, N, Hoang, H, et al.. Volatile constituents and anti-osteoporotic activity of the n-hexane extract from Homalomena gigantea rhizome. Nat Prod Commun 2022;17:1934578X221125433.10.1177/1934578X221125433Suche in Google Scholar

13. Dai, DN, Pham, TV, Dinh Luyen, N, Dung, VT, Huong, LT, Son, NT. Essential oils of two Vietnamese plants piper betle f. densum (piperaceae) and Disepalum plagioneurum (annonaceae): chemical composition, antimicrobial, and cytotoxic activities. Nat Prod Commun 2023;18:1934578X231190689. https://doi.org/10.1177/1934578x231190689.Suche in Google Scholar

14. Pham, T, Ha, N, Luyen, N, Thao, H, Thang, L, Ninh, TS, et al.. Chemical composition, mosquito larvicidal and antimicrobial activities, and molecular docking study of essential oils of Cinnamomum melastomaceum, Neolitsea buisanensis and Uvaria microcarpa from Vietnam. Chem Biodivers 2023;20:e202300652. https://doi.org/10.1002/cbdv.202300652.Suche in Google Scholar PubMed

15. Pham, T, Cuong, L, Ha, T, Luyen, N, Ha, N, Xuan, T, et al.. Essential oils of the leaves of Epaltes australis Less. and Lindera myrrha (Lour.) Merr.: chemical composition, antimicrobial, anti-inflammatory, Tyrosinase inhibitory, and molecular docking studies. Chem Biodivers 2024;20:e202301192. https://doi.org/10.1002/cbdv.202301192.Suche in Google Scholar PubMed

16. Adams, R. Identification of essential oil components by gas chromatography/quadrupole mass spectroscopy, 4th ed Carol Stream: Allured Publishing Corporation; 2007, 16:65–120 pp.Suche in Google Scholar

17. Fitzpatrick, FA. Cyclooxygenase enzymes: regulation and function. Curr Pharm Des 2004;10:577–88. https://doi.org/10.2174/1381612043453144.Suche in Google Scholar PubMed

18. Sun, QY, Zhou, HH, Mao, XY. Emerging roles of 5-lipoxygenase phosphorylation in inflammation and cell death. Tocchetti CG, editor. Oxid Med Cell Longev 2019;2019:2749173. https://doi.org/10.1155/2019/2749173.Suche in Google Scholar PubMed PubMed Central

19. Nguyen, HT, Vu, TY, Chandi, V, Polimati, H, Tatipamula, VB. Dual COX and 5-LOX inhibition by clerodane diterpenes from seeds of Polyalthia longifolia (Sonn.) Thwaites. Sci Rep 2020;10:15965. https://doi.org/10.1038/s41598-020-72840-8.Suche in Google Scholar PubMed PubMed Central

20. Berman, HM, Westbrook, J, Feng, Z, Gilliland, G, Bhat, TN, Weissig, H, et al.. The protein data bank. Nucleic Acids Res 2000;28:235–42. https://doi.org/10.1093/nar/28.1.235.Suche in Google Scholar PubMed PubMed Central

21. Madhavi, SG, Adzhigirey, M, Day, T, Annabhimoju, R, Sherman, W. Protein and ligand preparation: parameters, protocols, and influence on virtual screening enrichments. J Comput Aided Mol Des 2013;27:221–34. https://doi.org/10.1007/s10822-013-9644-8.Suche in Google Scholar PubMed

22. Friesner, RA, Murphy, RB, Repasky, MP, Frye, LL, Greenwood, JR, Halgren, TA, et al.. Extra precision Glide: docking and scoring incorporating a model of hydrophobic enclosure for protein–ligand complexes. J Med Chem 2006;49:6177–96. https://doi.org/10.1021/jm051256o.Suche in Google Scholar PubMed

23. Halgren, TA, Murphy, RB, Friesner, RA, Beard, HS, Frye, LL, Pollard, WT, et al.. Glide: a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. J Med Chem 2004;47:1750–9. https://doi.org/10.1021/jm030644s.Suche in Google Scholar PubMed

24. Genheden, S, Ryde, U. The MM/PBSA and MM/GBSA methods to estimate ligand-binding affinities. In: Expert opinion on drug discovery. London: Informa Healthcare; 2015, 10:449–61 pp.10.1517/17460441.2015.1032936Suche in Google Scholar PubMed PubMed Central

25. de Alencar, DC, Pinheiro, MLB, Pereira, JLda S, de Carvalho, JE, Campos, FR, Serain, AF, et al.. Chemical composition of the essential oil from the leaves of Anaxagorea brevipes (Annonaceae) and evaluation of its bioactivity. Nat Prod Res 2016;30:1088–92. https://doi.org/10.1080/14786419.2015.1101103.Suche in Google Scholar PubMed

26. Salleh, WMNHW, Khamis, S. Composition of volatile oil from Anaxagorea javanica. Chem Nat Compd 2021;57:474–5. https://doi.org/10.1007/s10600-021-03415-w.Suche in Google Scholar

27. Andrade, E, Oliveira, J, Zoghbi, M. Volatiles of Anaxagorea dolichocarpa Spreng. & Sandw. and Annona densicoma mart. Growing wild in the state of Pará, Brazil. Flavour Fragr J 2007;22:158–60. https://doi.org/10.1002/ffj.1776.Suche in Google Scholar

28. Cascaes, MM, da Silva, SHM, de Oliveira, MS, Cruz, JN, de Moraes, AAB, do Nascimento, LD, et al.. Exploring the chemical composition, in vitro and in silico study of the anticandidal properties of Annonaceae species essential oils from the Amazon. PLoS One 2023;18:e0289991. https://doi.org/10.1371/journal.pone.0289991.Suche in Google Scholar PubMed PubMed Central

29. Lavor, É, Fernandes, A, Teles, R, Leal, A, Oliveira Junior, R, Silva, M, et al.. Essential oils and their major compounds in the treatment of chronic inflammation: a review of antioxidant potential in preclinical studies and molecular mechanisms. Oxid Med Cell Longev 2018;2018:1–23. https://doi.org/10.1155/2018/6468593.Suche in Google Scholar PubMed PubMed Central

30. Zhao, Q, Zhu, L, Wang, S, Gao, Y, Jin, F. Molecular mechanism of the anti-inflammatory effects of plant essential oils: a systematic review. J Ethnopharmacol 2023;301:115829. https://doi.org/10.1016/j.jep.2022.115829.Suche in Google Scholar PubMed

31. Aati, H, El-Gamal, A, Kayser, O. Chemical composition and biological activity of the essential oil from the root of Jatropha pelargoniifolia Courb. native to Saudi Arabia. Saudi Pharmaceut J 2019;27:88–95. https://doi.org/10.1016/j.jsps.2018.09.001.Suche in Google Scholar PubMed PubMed Central

32. Kambiré, DA, Kablan, ACL, Yapi, TA, Vincenti, S, Maury, J, Baldovini, N, et al.. Neuropeltis acuminata (P. Beauv.): investigation of the chemical variability and in vitro anti-inflammatory activity of the leaf essential oil from the ivorian species. Molecules 2022;27:3759. https://doi.org/10.3390/molecules27123759.Suche in Google Scholar PubMed PubMed Central

33. Kumar, R, Kumar, R, Anjum, B, Prakash, O, Joshi, A, Pant, A, et al.. Phytochemical analysis, in-vitro antioxidant, anti-inflammatory and insect antifeeding activity of methanolic extract of Limnophila indica (L.). Druce 2019;7:1691–6.Suche in Google Scholar

34. Dong, H, He, L, Huang, M, Dong, Y. Anti-inflammatory components isolated from Atractylodes macrocephala Koidz. Nat Prod Res 2008;22:1418–27. https://doi.org/10.1080/14786410801931629.Suche in Google Scholar PubMed

35. Bouyahya, A, Guaouguaou, FE, El Omari, N, el Menyiy, N, Balahbib, A, El-Shazly, M, et al.. Anti-inflammatory and analgesic properties of Moroccan medicinal plants: phytochemistry, in vitro and in vivo investigations, mechanism insights, clinical evidences, and perspectives. J Pharm Anal 2021;12:35–7. https://doi.org/10.1016/j.jpha.2021.07.004.Suche in Google Scholar PubMed PubMed Central

36. Nam, SY, Kim, HY, Kim, HM, Jeong, HJ. Βeta-eudesmol reduces stem cell factor-induced mast cell migration. Int Immunopharmacol 2017;48:1–7. https://doi.org/10.1016/j.intimp.2017.04.017.Suche in Google Scholar PubMed

37. Kim, K. Anti-inflammatory and ECM gene expression modulations of β-eudesmol via NF-κB signaling pathway in normal human dermal fibroblasts. Biomedical Dermatology 2018;2. https://doi.org/10.1186/s41702-017-0014-3.Suche in Google Scholar

38. Seo, MJ, Kim, SJ, Kang, TH, Rim, HK, Jeong, HJ, Um, JY, et al.. The regulatory mechanism of β-eudesmol is through the suppression of caspase-1 activation in mast cell–mediated inflammatory response. Immunopharmacol Immunotoxicol 2011;33:178–85. https://doi.org/10.3109/08923973.2010.491082.Suche in Google Scholar PubMed

39. Xu, Q, Li, J, Chen, Z, Mao, Y, Tao, C. Protective effects of β-eudesmol against septic liver injury via inhibition of NF-κB signaling. Trop J Pharmaceut Res 2022;21:1183–8. https://doi.org/10.4314/tjpr.v21i6.7.Suche in Google Scholar

40. Chandra, M, Prakash, O, Kumar, R, Bachheti, RK, Bhushan, B, Kumar, M, et al.. β-Selinene-rich essential oils from the parts of Callicarpa macrophylla and their antioxidant and pharmacological activities. Medicine 2017;4:52. https://doi.org/10.3390/medicines4030052.Suche in Google Scholar PubMed PubMed Central

41. Trevizan, L, Nascimento, K, Santos, J, Kassuya, C, Cardoso, C, Vieira, M, et al.. Anti-inflammatory, antioxidant and anti-Mycobacterium tuberculosis activity of viridiflorol: the major constituent of Allophylus edulis (A. St.-Hil., A. Juss. & Cambess.) Radlk. J Ethnopharmacol 2016;192:510–5.10.1016/j.jep.2016.08.053Suche in Google Scholar PubMed


Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/znc-2023-0177).


Received: 2023-12-05
Accepted: 2024-03-08
Published Online: 2024-06-14
Published in Print: 2024-09-25

© 2024 Walter de Gruyter GmbH, Berlin/Boston

Heruntergeladen am 21.10.2025 von https://www.degruyterbrill.com/document/doi/10.1515/znc-2023-0177/html?lang=de
Button zum nach oben scrollen