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Li, H.;  Yang, Z. Active Compounds from Antrodia cinnamomea. Encyclopedia. Available online: https://encyclopedia.pub/entry/28742 (accessed on 19 April 2024).
Li H,  Yang Z. Active Compounds from Antrodia cinnamomea. Encyclopedia. Available at: https://encyclopedia.pub/entry/28742. Accessed April 19, 2024.
Li, Hua-Xiang, Zhen-Quan Yang. "Active Compounds from Antrodia cinnamomea" Encyclopedia, https://encyclopedia.pub/entry/28742 (accessed April 19, 2024).
Li, H., & Yang, Z. (2022, October 10). Active Compounds from Antrodia cinnamomea. In Encyclopedia. https://encyclopedia.pub/entry/28742
Li, Hua-Xiang and Zhen-Quan Yang. "Active Compounds from Antrodia cinnamomea." Encyclopedia. Web. 10 October, 2022.
Active Compounds from Antrodia cinnamomea
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This entry is adapted from the peer-reviewed paper 10.3390/bioengineering9100494

Antrodia cinnamomea is a precious and popular edible and medicinal mushroom. It has attracted increasing attention due to its various and excellent bioactivities, such as hepatoprotection, hypoglycemic, antioxidant, antitumor, anticancer, anti-inflammatory, immunomodulation, and gut microbiota regulation properties. To elucidate its bioactivities and develop novel functional foods or medicines, numerous studies have focused on the isolation and identification of the bioactive compounds of A. cinnamomea. 

Antrodia cinnamomea bioactive compound isolation purification

1. Introduction

Antrodia cinnamomea (syn. Antrodia camphorate) is a precious edible and medicinal mushroom; it belongs to phylum Basidiomycetes, family Polyporaceae, and genus Antrodia [1][2]. This fungus grows only on the inner cavity of a native tree called Cinnamomum kanehirai Hayata at an extremely slow pace and has been known as “ruby in the forest” [3][4]. A. cinnamomea has been historically used to treat food and drug intoxication [5]. A. cinnamomea exhibits various physiological and pharmacological properties, such as anticancer, antitumor, antioxidant, anti-inflammatory, hypoglycemic, hepatoprotective, immunomodulation, and gut microbiota regulation activities [6][7][8][9]. It has also attracted increasing research attention for the development of novel medicine due to its therapeutic action, particularly its prospective application as a chemoprophylaxis agent [1].
However, the wild fruiting bodies of A. cinnamomea are extremely expensive and in short supply because of host scarcity and slow growth. Accordingly, artificial cultivation techniques, such as cutting wood culture, solid-state fermentation, submerged fermentation, and dish culture, have been developed to supplement the expanding demand for A. cinnamomea. However, obtaining adequate amounts of excellent-quality A. cinnamomea through artificial culture has been greatly challenging [10][11]. Several differences exist between the type and content of the fruiting bodies and cultured mycelia of A. cinnamomea. Accordingly, numerous studies have demonstrated various methods for bridging such a disparity in bioactive metabolites between fruiting bodies and cultured mycelia [10][12].
With further in-depth studies, the research on A. cinnamomea is no longer limited to crude extracts. Various single substances, including polysaccharides, triterpenoids, ubiquinone derivatives, and maleic and succinic acid derivatives, have been isolated from fruiting bodies and cultured mycelia of A. cinnamomea. Currently, numerous kinds of isolation methods are used for the metabolites from A. cinnamomea. However, the standardization of product quality and purity is lacking. Numerous active substances remain undiscovered due to the limitations of isolation and purification methods.

2. Isolation and Purification of Bioactive Compounds from A. cinnamomea

More than 200 compounds have been isolated and identified in A. cinnamomea, and they include polysaccharides, triterpenoids, ubiquinone derivatives, maleic and succinic acid derivatives, benzene derivatives, and glycoprotein. The chemical structures of the main bioactive components from A. cinnamomea are showed in Figure 1. However, a number of compounds with significant biological activity in A. cinnamomea still have not been found [13][14]. The following section summarizes the separation and purification methods of various active substances from A. cinnamomea.
Bioengineering 09 00494 g001a 550Bioengineering 09 00494 g001b 550
Figure 1. The chemical structures of the main bioactive components from Antrodia cinnamomea. (a) Triterpenoids, (b) ubiquinone derivatives, (c) maleic and succinic acid derivatives, (d) benzene derivatives.

3. Identification and Quantification of Bioactive Compounds from A. cinnamomea

Aside from isolation and purification, the identification of particular bioactive compounds of A. cinnamomea is critical. This knowledge is essential for understanding the biological activities of these metabolites and discovering new A. cinnamomea bioactive compounds. Typically, the characterization and quantification of natural products can use various detection techniques, including nuclear magnetic resonance (NMR), infrared spectra, and mass spectrometry (MS) detection. NMR has steadily developed and has become an essential technology for chemical identification and structural characterization. This technique enables the acquisition of data from extremely mass-limited samples and the investigation of very complex materials [15]. 1H-NMR and 13C-NMR analyses were used to identify compounds from solid-state cultured mycelia of A. cinnamomea [16]. Finally, a quinone, four phenolic acid derivatives, three ubiquinone derivatives, two alkaloids, and a triterpenoid has been identified. These compounds exhibit potent neuroprotective activities against 6-hydroxydopamine-induced toxicity in PC12 cells [16]. NMR can also be used to determine the amounts of various components in a mixture quickly and precisely. This method, known as quantitative NMR (qNMR), has found novel uses in biological and pharmacological research. qNMR is a primary ratio method compared with other instrumental analytical methods because the resulting peak areas are proportionate to the number of matching nuclei. Consequently, qNMR has been selected for the quantitative analysis of a benzenoid-rich fraction containing three primary benzenoids of A. cinnamomea due to its superiority to other standard chromatographic techniques in detecting the amounts of specific herbal mixture elements [17].
Fingerprint analysis is used for the thorough assessment of the quality of herbal medicines and their associated products. Recently, the HPLC fingerprinting approach supplemented by ultraviolet (UV) and photodiode array (PDA) has been widely utilized for herbal-quality testing. However, UV and PDA detectors present several problems in the isolation of target analytes from interfering impurities. Thus, these techniques involve time-consuming sample preparation and long HPLC run times. To resolve these issues, scientists use the more sensitive liquid chromatography–tandem MS (HPLC-MS/MS), which can offer better overall information, such as molecular weight, retention time, and analyte collision fragments. Accordingly, a validated HPLC-MS/MS method for the quick and precise measurement of compounds from A. cinnamomea was established [18]. The method can be used to simultaneously measure seven characteristic chemicals, including antcin A, antcin B, antcin C, antcin H, antcin K, dehydroeburicoic acid, and DMB [18]. Triterpenoids are a significant bioactive component of A. cinnamomea, and different cultivation techniques exhibit significant variations. Qiao et al. [19] reported the contents of 10 ergostane-type and 8 landostane-type triterpenoids of A. cinnamomea samples derived from cutting wood culture, solid-state fermentation, submerged fermentation, and dish culture. It was determined by ultra-high performance liquid chromatography/ultraviolet (UPLC/UV) or supercritical fluid chromatography coupled with mass spectrometry (SFC/MS, for 25R/S-antcin A) within 16 min. The result showed that the 18 kinds of triterpenoids accounted for 118.2 ± 28.2, 89.4 ± 30.8, and 116.5 ± 1.1 mg·g−1 in wood-cultured fruiting bodies, wood-cultured mycelia, and dish-cultured, respectively. However, no triterpenoids were detected in the solid support cultivation or submerged fermentation samples in this research [19]. The development of products derived from A. cinnamomea benefits from the precise and rapid measurement of signature compounds in various samples using this method. Ultra-performance liquid chromatography quadrupole time-of-flight MS (UPLC/Q-TOF/MS) has been used to characterize and quantify mixture compounds. For the first time, the UPLC/Q-TOF/MS method was used to identify the extracts from A. cinnamomea and led to the discovery of 139 chemical compounds, including 102 terpenoids, 8 benzenoids, 2 purine nucleosides, and 27 other classes [20]. The development of this method has significant implications for the exploration of A. cinnamomea products.

References

  1. Lu, M.C.; El-Shazly, M.; Wu, T.Y.; Du, Y.C.; Chang, T.T.; Chen, C.F.; Hsu, Y.M.; Lai, K.H.; Chiu, C.P.; Chang, F.R.; et al. Recent research and development of Antrodia cinnamomea. Pharmacol Ther. 2013, 139, 124–156.
  2. Chang, T.T.; Chou, W.N. Antrodia cinnamomea sp. nov. on Cinnamomum kanehirai in Taiwan. Mycol. Res. 1995, 99, 756–758.
  3. Liu, Y.K.; Chen, K.H.; Leu, Y.L.; Way, T.D.; Wang, L.W.; Chen, Y.J.; Liu, Y.M. Ethanol extracts of Cinnamomum kanehirai Hayata leaves induce apoptosis in human hepatoma cell through caspase-3 cascade. Onco Targets Ther. 2015, 8, 99–109.
  4. Jin, Y.; Liu, H.; Liu, J.; Xing, H.; Wang, F.; Deng, L. Efficient production of 4-Acetylantroquinonol B from Antrodia cinnamomea through two-stage carbon source coordination optimization. Bioresour. Technol. Rep. 2021, 15, 100732.
  5. Ao, Z.H.; Xu, Z.H.; Lu, Z.M.; Xu, H.Y.; Zhang, X.M.; Dou, W.F. Niuchangchih (Antrodia camphorata) and its potential in treating liver diseases. J. Ethnopharmacol. 2009, 121, 194–212.
  6. Ding, R.; Ning, X.; Ye, M.; Yin, Y. Antrodia camphorata extract (ACE)-induced apoptosis is associated with BMP4 expression and p53-dependent ROS generation in human colon cancer cells. J. Ethnopharmacol. 2021, 268, 113570.
  7. Cheng, J.J.; Chao, C.H.; Chang, P.C.; Lu, M.K. Studies on anti-inflammatory activity of sulfated polysaccharides from cultivated fungi Antrodia cinnamomea. Food Hydrocoll. 2016, 53, 37–45.
  8. Lin, I.Y.; Pan, M.H.; Lai, C.S.; Lin, T.T.; Chen, C.T.; Chung, T.S.; Chen, C.L.; Lin, C.H.; Chuang, W.C.; Lee, M.C.; et al. CCM111, the water extract of Antrodia cinnamomea, regulates immune-related activity through STAT3 and NF-kappaB pathways. Sci. Rep. 2017, 7, 4862.
  9. Chao, T.Y.; Hsieh, C.C.; Hsu, S.M.; Wan, C.H.; Lian, G.T.; Tseng, Y.H.; Kuo, Y.H.; Hsieh, S.C. Ergostatrien-3beta-ol (EK100) from Antrodia camphorata attenuates oxidative stress, inflammation, and liver injury in nitro and in vivo. Prev. Nutr. Food Sci. 2021, 26, 58–66.
  10. Zhang, B.B.; Guan, Y.Y.; Hu, P.F.; Chen, L.; Xu, G.R.; Liu, L.; Cheung, P.C.K. Production of bioactive metabolites by submerged fermentation of the medicinal mushroom Antrodia cinnamomea: Recent advances and future development. Crit. Rev. Biotechnol. 2019, 39, 541–554.
  11. Chen, L.; Wang, Z.; Zhang, B.; Ge, M.; Ng, H.; Niu, Y.; Liu, L. Production, structure and morphology of exopolysaccharides yielded by submerged fermentation of Antrodia cinnamomea. Carbohydr. Polym. 2019, 205, 271–278.
  12. Zeng, W.W.; Chen, T.C.; Liu, C.H.; Wang, S.Y.; Shaw, J.F.; Chen, Y.T. Identification and isolation of an intermediate metabolite with dual antioxidant and anti-proliferative activity present in the fungus Antrodia cinnamomea cultured on an alternative medium with Cinnamomum kanehirai leaf extract. Plants 2021, 10, 737.
  13. Ganesan, N.; Baskaran, R.; Velmurugan, B.K.; Thanh, N.C. Antrodia cinnamomea-An updated minireview of its bioactive components and biological activity. J. Food Biochem. 2019, 43, e12936.
  14. Geethangili, M.; Tzeng, Y.M. Review of Pharmacological Effects of Antrodia camphorata and Its Bioactive Compounds. Evid. Based Complement. Altern. Med. 2011, 2011, 212641.
  15. Ocampos, F.M.M.; Menezes, L.R.A.; Dutra, L.M.; Santos, M.F.C.; Ali, S.; Barison, A. NMR in Chemical Ecology: An Overview Highlighting the Main NMR Approaches. eMagRes 2017, 6, 325–341.
  16. Zou, X.G.; Xu, M.T.; Dong, X.L.; Ying, Y.M.; Guan, R.F.; Wu, W.C.; Yang, K.; Sun, P.L. Solid-state-cultured mycelium of Antrodia camphorata exerts potential neuroprotective activities against 6-hydroxydopamine-induced toxicity in PC12 cells. J. Food Biochem. 2022, 46, e14208.
  17. Wu, T.Y.; Du, Y.C.; Hsu, Y.M.; Lu, C.Y.; Singab, A.N.B.; El-Shazly, M.; Hwang, T.L.; Lin, W.Y.; Lai, K.H.; Lu, M.C.; et al. New approach to the characterization and quantification of Antrodia cinnamomea benzenoid components utilizing HPLC-PDA, qNMR and HPLC-tandem MS: Comparing the wild fruiting bodies and its artificial cultivated commercial products. Food Res. Int. 2013, 51, 23–31.
  18. Huang, H.S.; Hsu, J.L.; Yu, C.C.; Chang, L.C.; Chen, C.R.; Huang, T.C.; Chang, C.I. Qualitative and quantitative analysis of seven signature components in the fruiting body of Antrodia cinnamomea by HPLC—ESI—MS/MS. Acta Chromatogr. 2016, 28, 387–402.
  19. Qiao, X.; Song, W.; Wang, Q.; Liu, K.D.; Zhang, Z.X.; Bo, T.; Li, R.Y.; Liang, L.N.; Tzeng, Y.M.; Guo, D.A.; et al. Comprehensive chemical analysis of triterpenoids and polysaccharides in the medicinal mushroom Antrodia cinnamomea. RSC Adv. 2015, 5, 47040–47052.
  20. Zhang, Y.; Lv, P.; Ma, J.; Chen, N.; Guo, H.; Chen, Y.; Gan, X.; Wang, R.; Liu, X.; Fan, S.; et al. Antrodia cinnamomea exerts an anti-hepatoma effect by targeting PI3K/AKT-mediated cell cycle progression in vitro and in vivo. Acta Pharm. Sin. B 2022, 12, 890–906.
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Subjects: Food Science & Technology; Biotechnology & Applied Microbiology
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Hua-Xiang Li
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Zhen-Quan Yang
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Entry Collection: Extraction Techniques in Sample Preparation
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Update Date: 11 Oct 2022
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