Isolation, Purification and NMR-Based Structural Elucidation of Sterol Derivatives from Ganoderma resinaceum (Fr.) Karst

Emran Habibi; Mohammad Azadbakht; Zahra Delroz; Abed Besmel; Lutfun Nahar

doi:10.53941/npa.2026.100003

Abstract

This study presents a detailed phytochemical investigation of the medicinal mushroom Ganoderma resinaceum (Fr.) Karst., collected from Mazandaran Province, Iran. Sequential maceration using n-hexane, ethyl acetate (EtOAc), and methanol (MeOH) yielded crude extracts of differing polarity. Chromatographic purification of the EtOAc fraction produced four major sterol derivatives: ergosterol, ergosterol peroxide, 9,11-dehydroergosterol peroxide, and ergosta-7,22-dien-3β-ol. Their structures were confirmed using comprehensive spectroscopic techniques, including ¹H NMR, ¹³C NMR, and DEPT. To the best of our knowledge, this is the first report of these sterol derivatives from Iranian G. resinaceum. The findings highlight the chemical diversity of the species and underscore the relevance of medium-polarity fractions as reservoirs of pharmacologically significant sterols.

References

1.
Glamočlija, J.; Soković, M. Fungi a Source with Huge Potential for “Mushroom Pharmaceuticals”. Lek. Sirovine 2017, 37, 50–56.
2.
Habibi, E.; Hemmati, P.; Arabnozari, H.; et al. Phytochemical Analysis and Immune-Modulatory Potential of Trichaptum biforme Polysaccharides: Implications for Cancer. Int. J. Biol. Macromol. 2024, 280, 135691.
3.
Lindequist, U.; Niedermeyer, T.H.; Jülich, W.-D. The Pharmacological Potential of Mushrooms. Evid. Based Complement. Altern. Med. 2005, 2, 285–299.
4.
Łysakowska, P.; Sobota, A.; Wirkijowska, A. Medicinal Mushrooms: Their Bioactive Components, Nutritional Value and Application in Functional Food Production—A Review. Molecules 2023, 28, 5393.
5.
Patel, S.; Goyal, A. Recent Developments in Mushrooms as Anti-Cancer Therapeutics: A Review. 3 Biotech 2012, 2, 1–5.
6.
Baby, S.; Johnson, A.J.; Govindan, B. Secondary Metabolites from Ganoderma. Phytochemistry 2015, 114, 66–101.
7.
Ahmad, M.F.; Alsayegh, A.A.; Ahmad, F.A.; et al. Ganoderma lucidum: Insight into Antimicrobial and Antioxidant Properties with Development of Secondary Metabolites. Heliyon 2024, 10, e25607.
8.
Vazirian, M.; Faramarzi, M.A.; Ebrahimi, S.E.; et al. Antimicrobial Effect of the Lingzhi or Reishi Medicinal Mushroom, Ganoderma lucidum (Higher Basidiomycetes) and Its Main Compounds. Int. J. Med. Mushrooms 2014, 16, 77–84.
9.
Ahmad, M.F. Ganoderma lucidum: Persuasive Biologically Active Constituents and Their Health Endorsement. Biomed. Pharmacother. 2018, 107, 507–519.
10.
Rangsinth, P.; Sharika, R.; Pattarachotanant, N.; et al. Potential Beneficial Effects and Pharmacological Properties of Ergosterol, a Common Bioactive Compound in Edible Mushrooms. Foods 2023, 12, 2529.
11.
Jeong, Y.U.; Park, Y.J. Ergosterol Peroxide from the Medicinal Mushroom Ganoderma lucidum Inhibits Differentiation and Lipid Accumulation of 3T3-L1 Adipocytes. Int. J. Mol. Sci. 2020, 21, 460.
12.
Wang, L.; Li, J.; Zhang, J.; et al. Traditional Uses, Chemical Components and Pharmacological Activities of the Genus Ganoderma P. Karst.: A Review. RSC Adv. 2020, 10, 42084–42097.
13.
Dai, J.; Mumper, R.J. Plant Phenolics: Extraction, Analysis and Their Antioxidant and Anticancer Properties. Molecules 2010, 15, 7313–7352.
14.
Habibi, E.; Sadat-Ebrahimi, S.E.; Mousazadeh, S.A.; et al. Mycochemical Investigation of the Turkey Tail Medicinal Mushroom Trametes versicolor (Higher Basidiomycetes): A Potential Application of the Isolated Compounds in Documented Pharmacological Studies. Int. J. Med. Mushrooms 2015, 17, 255–265.
15.
Bakhshi Jouybari, H.; Bekhradnia, A.; Mirzaee, F.; et al. Chemical Composition of the Lumpy Bracket Mushroom (Trametes gibbosa). Res. J. Pharmacogn. 2022, 9, 19–27.
16.
Panda, S.K.; Luyten, W. Medicinal Mushrooms: Clinical Perspective and Challenges. Drug Discov. Today 2022, 27, 636–651.
17.
Rašeta, M.; Kebert, M.; Mišković, J.; et al. Ganoderma pfeifferi Bres. and Ganoderma resinaceum Boud. as Potential Therapeutic Agents: A Comparative Study on Antiproliferative and Lipid-Lowering Properties. J. Fungi 2024, 10, 501.
18.
Kou, R.W.; Xia, B.; Wang, Z.J.; et al. Triterpenoids and Meroterpenoids from the Edible Ganoderma resinaceum and Their Potential Anti-Inflammatory, Antioxidant and Anti-Apoptosis Activities. Bioorg. Chem. 2022, 121, 105689.
19.
Sułkowska-Ziaja, K.; Zengin, G.; Gunia-Krzyża, A.; et al. Bioactivity and Mycochemical Profile of Extracts from Mycelial Cultures of Ganoderma spp. Molecules 2022, 27, 275.
20.
Lv, G.; Zhao, J.; Duan, J. a.; et al. Comparison of Sterols and Fatty Acids in Two Species of Ganoderma. Chem. Cent. J. 2012, 6, 10.
21.
Chafouz, R.; Karavergou, S.; Tsiftsoglou, O.S.; et al. Ganoderma adspersum (Ganodermataceae): Investigation of Its Secondary Metabolites and the Antioxidant, Antimicrobial, and Cytotoxic Potential of Its Extracts. Int. J. Mol. Sci. 2023, 25, 516.
22.
Chen, S.; Yong, T.; Zhang, Y.; et al. Anti-Tumor and Anti-Angiogenic Ergosterols from Ganoderma lucidum. Front. Chem. 2017, 5, 85.
23.
Li, L.; Zhu, Y.; Cheng, W.; et al. Efficacy of Ergosterol and Ergosterol Peroxide in Different Anti-Inflammatory Models—A Comparison Study. Food Agric. Immunol. 2024, 35, 2423638.
24.
Xu, J.; Xiao, C.; Xu, H.; et al. Anti-Inflammatory Effects of Ganoderma lucidum Sterols via Attenuation of the p38 MAPK and NF-κB Pathways in LPS-Induced RAW 264.7 Macrophages. Food Chem. Toxicol. 2021, 150, 112073.
25.
Yuan, L.; Zhang, F.; Shen, M.; et al. Phytosterols Suppress Phagocytosis and Inhibit Inflammatory Mediators via ERK Pathway on LPS-Triggered Inflammatory Responses in RAW264.7 Macrophages and the Correlation with Their Structure. Foods 2019, 8, 582.

Scilight Press

Author Information

Abstract

Keywords

References

About Scilight

Journals

Publishing Policies

Contact Us