Essential oil composition, anti-tyrosinase activity, and molecular docking studies of Knema intermedia Warb. (Myristicaceae)

Wan Mohd Nuzul Hakimi Wan Salleh

Abstract

Knema is one of the genera in the Myristicaceae family. The genus includes 60 species in Southeast Asia and is traditionally used for treating skin disorders. Here, for the first time, the essential oil, anti-tyrosinase, and molecular docking studies of Knema intermedia were evaluated. The essential oil was obtained by hydrodistillation and fully characterized by gas chromatography (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Anti-tyrosinase activity was evaluated against mushroom tyrosinase, whereas molecular docking studies were performed using Autodock vina embedded in PyRx to evaluate the binding interactions of major components. A total of 37 components (97.3%) were successfully identified in the essential oil, which was characterized by high amounts of t-muurolol (20.1%), ?-copaene (14.4%), ?-cadinene (13.9%), germacrene B (9.5%), and ?-selinene (7.0%). The essential oil displayed moderate inhibitory activity towards tyrosinase with an IC50 value of 70.2 ?g/mL. The best docking energy was observed with ?-selinene (-7.8 kcal/mol), and it also forms interactions with His85, His263, and His244 which are important amino acid residues of the tyrosinase receptor. Hence, this study provides valuable scientific data on K. intermedia as potential candidate for the development of natural antiaging formulations. 2023 Walter de Gruyter GmbH, Berlin/Boston.

References

Hara, M. Potential use of essential oils to enhance heat tolerance in plants. Z Naturforsch C Biosci 2020;75:225–31. https://doi.org/10.1515/znc-2019-0233.Search in Google ScholarPubMed

Salleh, WMNHW, Ahmad, F, Khong, HY. Chemical compositions and antimicrobial activity of the essential oils of Piper abbreviatum, P. erecticaule and P. lanatum (Piperaceae). Nat Prod Commun 2014;9:1795–8. https://doi.org/10.1177/1934578x1400901235.Search in Google Scholar

Salleh, WMNHW, Khamis, S. Essential oil composition and antioxidant activity of Paramignya lobata. Chem Nat Compd 2021;57:774–5. https://doi.org/10.1007/s10600-021-03474-z.Search in Google Scholar

Salleh, WMNHW, Ahmad, F. Antioxidant and anti-inflammatory activities of essential oils of Actinodaphne macrophylla and A. pruinosa (Lauraceae). Nat Prod Commun 2016;11:853–5. https://doi.org/10.1177/1934578x1601100639.Search in Google Scholar

Salleh, WMNHW, Muhammad, NA, Ghani, NA, Jauri, MH. Volatile components of Dillenia reticulata King (Dilleniaceae) essential oil and their cytotoxicity. Bull Chem Soc Ethiop 2023;37:245–9.10.4314/bcse.v37i1.19Search in Google Scholar

Fiocco, D, Arciuli, M, Arena, MP, Benvenuti, S, Gallone, A. Chemical composition and the anti-melanogenic potential of different essential oils. Flav Frag J 2016;31:255–61. https://doi.org/10.1002/ffj.3315.Search in Google Scholar

Kim, YJ, Uyama, H. Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci 2005;62:1707–23. https://doi.org/10.1007/s00018-005-5054-y.Search in Google ScholarPubMed

Sinclair, J. The genus Knema (Myristicaceae) in Malaysia and outside Malaysia. Singapore: Garden Bulletin; 1961.Search in Google Scholar

Salleh, WMNHW, Anuar, MZA, Khamis, S, Nafiah, MA, Sul’ain, MD. Chemical investigation and biological activities of the essential oil of Knema kunstleri Warb. from Malaysia. Nat Prod Res 2021;35:2279–84. https://doi.org/10.1080/14786419.2019.1669027.Search in Google ScholarPubMed

Salleh, WMNHW, Ahmad, F. Phytochemistry and biological activities of the genus Knema (Myristicaceae). Pharmaceut Sci 2017;23:249–55. https://doi.org/10.15171/ps.2017.37.Search in Google Scholar

Burkill, IH. A dictionary of the economic products of the Malay Peninsula. Malaysia: Ministry of Agriculture and Co-operatives, Kuala Lumpur; 1966.Search in Google Scholar

Siddiqi, MR, Wilson, TK. Floral anatomy of the genus Knema (Myristicaceae). Biologia 1976;22:127–41.Search in Google Scholar

Siddiqi, MR, Wilson, TK. Leaf anatomy of the genus Knema. Biologia 1975;21:167–75.Search in Google Scholar

Yahaya, AAH, Salleh, WMNHW, Ghani, NA, Khamis, S, Rezali, NS, Juhari, MAA. Chemical composition and bioactivities of Magnolia candollii H. Keng essential oil. Z Naturforsch C J Biosci 2022;77:519–23. https://doi.org/10.1515/znc-2022-0100.Search in Google ScholarPubMed

Salleh, WMNHW, Ghani, NA, Abdel-Aal, MAB. Chemical composition and anticholinesterase activity of Lepisanthes rubiginosa (Roxb.) Leenh. essential oil. Z Naturforsch C J Biosci 2022;77:525–9. https://doi.org/10.1515/znc-2022-0105.Search in Google ScholarPubMed

Azhar, MAM, Salleh, WMNHW, Khamis, S. Essential oil composition of three Cryptocarya species from Malaysia. Z Naturforsch C J Biosci 2020;75:297–301. https://doi.org/10.1515/znc-2020-0079.Search in Google ScholarPubMed

Shakri, NM, Salleh, WMNHW, Khamis, S, Ali, NAM, Nadri, MH. Composition of the essential oils of three Malaysian Xylopia species (Annonaceae). Z Naturforsch C J Biosci 2020;75:479–84. https://doi.org/10.1515/znc-2020-0096.Search in Google ScholarPubMed

Shakri, NM, Salleh, WMNHW, Khamis, S, Ali, NAM, Shaharudin, SM. Chemical composition of the essential oils of four Polyalthia species from Malaysia. Z Naturforsch C J Biosci 2020;75:473–8. https://doi.org/10.1515/znc-2020-0097.Search in Google ScholarPubMed

Adams, RP. Identification of essential oil components by gas chromatography/mass spectroscopy. Illinois: Allured Publishing Co. Carol Stream; 1995.Search in Google Scholar

Salleh, WMNHW, Khamis, S. Chemical composition and tyrosinase inhibitory activity of the essential oil of Rhodamnia cinerea. Chem Nat Compd 2021;57:770–1. https://doi.org/10.1007/s10600-021-03472-1.Search in Google Scholar

Abbas, Q, Ashraf, Z, Hassan, M, Nadeem, H, Latif, M, Afzal, S, et al.. Development of highly potent melanogenesis inhibitor by in vitro, in vivo and computational studies. Drug Des Dev 2017;11:2029–46. https://doi.org/10.2147/dddt.s137550.Search in Google ScholarPubMed PubMed Central

Hassan, M, Vanjare, BD, Sim, KY, Raza, H, Lee, KH, Shahzadi, S, et al.. Biological and cheminformatics studies of newly designed triazole based derivatives as potent inhibitors against mushroom tyrosinase. Molecules 2022;27:1731–44. https://doi.org/10.3390/molecules27051731.Search in Google ScholarPubMed PubMed Central

Thinh, BB, Khoi, NT, Doudkin, RV, Thin, DB, Ogunwande, IA. Chemical composition of essential oil and antioxidant activity of the essential oil and methanol extracts of Knema globularia (Lam.) Warb. from Vietnam. Nat Prod Res 2022 (in press). https://doi.org/10.1080/14786419.2022.2103698.Search in Google ScholarPubMed

Salleh, WMNHW, Ahmad, F, Khong, HY, Zulkifli, RM. Comparative study of the essential oils of three Beilschmiedia species and their biological activities. Int J Food Sci Technol 2016;51:240–9. https://doi.org/10.1111/ijfs.12962.Search in Google Scholar