Antimicrobial properties of Fomitopsis officinalis in the light of its bioactive metabolites: a review

Figures & data

Table 1. Secondary metabolites isolated from F. officinalis.

Molecule	References	Antimicrobial properties
Eburicoic acid	Wu et al. 2005 and Shi et al. 2017	–
Sulfurenic acid	Wu et al. 2005	–
Fomefficinic acid A-E	Wu et al. 2004	–
Versisponic acid D	Wu et al. 2005	–
Fomefficinic acid F,G	Wu et al. 2009 and Naranmandakh et al. 2018	–
Dehydroeburicoic acid	Wu et al. 2005, Feng et al. 2010 and Shi et al. 2017	–
Dehydrosulfurenic acid	Wu et al. 2005 and Feng et al. 2010	–
3-Ketodehydrosulfurenic acid	Wu et al. 2005, Feng et al. 2010 and Shi et al. 2017	–
Fomefficinol A-B	Wu et al. 2009	–
Fomlactone A-C	Wu et al. 2009	–
Obtusifoldienol	Epstein and Van Lear 1966	–
Eburicodiol	Anderson and Epstein 1971	–
(3β,5α,6β)-3,6-dihydroxy-4,4,14-trimethyl-Pregn-8- en-20-one	Anderson et al. 1972	–
3α-hydroxy-4,4,14α-trimethyl-5α-pregn-8-en-20- one	Epstein and Van Lear 1966	–
Eburical	Anderson and Epstein 1971	–
Agaric acid	Airapetova et al. 2010 and Airapetova and Gromovykh. 2013	–
Laricinolic acid	Erb et al. 2000 and Wu et al. 2009	–
Officinalic acid	Epstein et al. (1979), Erb et al. (2000) and Wu et al. (2009)	–
2H-6-chloro-2-oxo-4-phenyl-1-Benzopyran-3- carboxylicacidethylester	Hwang et al. 2013	Antimicrobial
6-Chloro-4-phenyl-coumarin	Hwang et al. 2013	Antimicrobial
Officimalonic acids A-H	Han et al. 2016	–
Fomitopsin A	Han et al. 2016	–
Fomitopsin C	Shi et al. 2017	–
Fomitopsin F, G, H	Naranmandakh et al. 2018	Trypanocidal
Demalonyl fomitopsin H	Naranmandakh et al. 2018	Trypanocidal
Fomitopsin D Ethyl ester	Naranmandakh et al. 2018	Trypanocidal
3-acetyloxylanosta-8, 24-dien-21-oic acid	Shi et al. 2017	–
(25S)-(+)-12α-hydroxy-3α- malonyloxy-24-methyllanosta-8,24(31)-dien-26-oic acid	Naranmandakh et al. 2018	–
15α-hydroxy- 3-oxo-24-methylenelanosta-7,9(11)-dien-21-oic acid	Wu et al. 2004, Han et al. 2016 and Naranmandakh et al. 2018	Trypanocidal
t-Z-trans-zeatin	Vedenicheva et al. 2016	–
c-Z-cis-zeatin	Vedenicheva et al. 2016	–
ZR-zeatin riboside	Vedenicheva et al. 2016	–
zeatin-О-glucoside	Vedenicheva et al. 2016	–

Figure 1. Simple coumarin or benzopyrone.

Table 2. Fomitopsins isolated from Fomitopsis species.

	F. feei	F. spraguei	F. officinalis
Fomitopsin A		Quang et al. 2005	Han et al. 2016
Fomitopsin B		Quang et al. 2005
Fomitopsin C		Quang et al. 2005	Shi et al. 2017
Fomitopsin D	Isaka et al. 2017
Fomitopsin E	Isaka et al. 2017
Fomitopsin F	Isaka et al. 2017		Naranmandakh et al. 2018
Fomitopsin G			Naranmandakh et al. 2018
Fomitopsin H			Naranmandakh et al. 2018

Figure 2. Naturally occurring coumarins (1–2) and newly synthesised analogues (3–4) from F. officinalis. (1) 6-chloro-4-phenyl-2H-chromen-2-one; (2) ethyl 6-chloro-2-oxo-4-phenyl-2H-chromen-3-carboxylate. From Hwang et al. (2013).

Figure 3. Lanostane or (5S,8R,9S,10R,13R,14S,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,5,6,7,8,9,11,12, 15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene. From: https://pubchem.ncbi.nlm.nih.gov/compound/Lanostane.

Figure 4. Lanostane-type triterpenoids isolated from F. officinalis. (1) 3-[2-(carboxyacetyl)oxy]-12-hydroxy24-methyl-lanost-8,24-dien-26,23-lactone named fomitopsin G; (2) 3-[2-(carboxyacetyl)oxy]-18,23-epoxy-12-hydroxy-24- methyl-lanost-8-en-26,23-lactone named fomitopsin H; (3) 18,23-epoxy-3,12,-dihydroxy-24-methyl-lanost-8-en-26,23-lactone named demalonyl fomitopsin H; (4) ethyl ester derivative of fomitopsin D; (5) fomitopsin F; (6) (25S)-(+)-12α-hydroxy-3αmalonyloxy-24-methyllanosta-8,24(31)-dien-26-oic acid; (7) fomeofficinic acid G; (8) 15α-hydroxy-3-oxo-24-methylenelanosta-7,9(11)-dien-21- oic; (9) fomitopsin C; (10) officimalonic acid A; (11) (3R, 12R, 23S)-3-carboxyacetyloxy-12-hydroxy-24-methyl-7-oxo-lanost-8,24-dien-26,23-lactone, named officimalonic acid B; (12) officimalonic acid C; (13) officimalonic acid D; (14) officimalonic acid E; (15) officimalonic acid F; (16) officimalonic acid G; (17) officimalonic acid H. Modified from Quang et al. (2005), Han et al. (2016) and Naranmandakh et al. (2018).

Wu X, Yang JS, Dong YS. 2005. Chemical constituents of Fomes officinalis (Ⅰ). Chin Tradit Herb Drugs. 36:811–814.

 Google Scholar

Shi ZT, Bao HY, Feng S. 2017. Antitumor activity and structure-activity relationship of seven lanostane-type triterpenes from Fomitopsis pinicola and F. officinalis. Zhongguo Zhong Yao Za Zhi= Zhongguo Zhongyao Zazhi [China J Chin Mater Med]. 42(5):915–922. Chinese.

 PubMedGoogle Scholar

Wu X, Yang JS, Zhou L, Dong YS. 2004. New lanostane-typetriterpenes from Fomes officinalis. Chem Pharm Bull. 52:1375–1377.

 PubMed Web of Science ®Google Scholar

Wu X, Yang JS, Yan M. 2009. Four New Triterpenes from Fungus of Fomes officinalis. Chem Pharm Bull. 57:195–197.

 PubMed Web of Science ®Google Scholar

Naranmandakh S, Murata T, Odonbayar B, Suganuma K, Batkhuu J, Sasaki K. 2018. Lanostane triterpenoids from Fomitopsis officinalis and their trypanocidal activity. J Nat Med. 72(2):523–529.

 PubMed Web of Science ®Google Scholar

Feng W, Yang J, Xu X, Liu Q. 2010. Quantitative determination of lanostane triterpenes in Fomes officinalis and their fragmentation study by HPLC‐ESI. Phytochem Anal. 21(6):531–538.

 PubMed Web of Science ®Google Scholar

Epstein WW, Van Lear G. 1966. Metabolites of Fomes officinalis. J Org Chem. 31:3434–3435.

 Web of Science ®Google Scholar

Anderson C, Epstein W. 1971. Metabolic intermediates in the biological oxidation of lanosterol to eburicoic acid. Phytochemistry. 10:2713–2717.

 Web of Science ®Google Scholar

Anderson CG, Vanlear G, Epstein WW. 1972. Minor triterpenes of Fomes officinalis. Phytochemistry. 11:2847–2852.

 Web of Science ®Google Scholar

Airapetova AY, Gavrilin MV, Dmitriev AB, Mezenova TD. 2010. Examination of the structure of agaricinic acid using 1 H and 13 C NMR spectroscopy. Pharm Chem J. 44(9):510–513.

 Web of Science ®Google Scholar

Airapetova A, Gromovykh T. 2013. Выделение и идентификация агарициновой кислоты из мицелия Fomitopsis officinalis (Vill. Fr.:) Bond. et Sing. [Selection and identification of agaricine acid from micelia of Fomitopsis officinalis (Vill. Fr.:) Bond. et Sin]. Химия Растительного Сырья [Chem Plant Raw Mater]. 2:101–106.

 Google Scholar

Erb B, Borschberg HJ, Arigoni D. 2000. The structure of laricinolic acid and its biomimetic transformation into officinalic acid. J Chem Soc Perkin Trans. 1(15):2307–2309.

 Google Scholar

Epstein WW, Sweat FW, Van Lear G, Lovell FM, Gabe EJ. 1979. Structure and stereochemistry of officinalic acid, a novel triterpene from Fomes officinalis. J Am Chem Soc. 101:2748–2750.

 Web of Science ®Google Scholar

Hwang CH, Jaki BU, Klein LL, Lankin DC, McAlpine JB, Napolitano JG, Fryling NA, Franzblau SG, Cho SH, Stamets PE, et al. 2013. Chlorinated coumarins from the polypore mushroom Fomitopsis officinalis and their activity against Mycobacterium tuberculosis. J Nat Prod. 76(10):1916–1922.

 PubMed Web of Science ®Google Scholar

Vedenicheva NP, Al-Maali GA, Mytropolska NY, Mykhaylova OB, Bisko NA, Kosakivska IV. 2016. Endogenous cytokinins in medicinal Basidiomycetes mycelial biomass. Biotechnol Acta. 9(1):55–63.

 Google Scholar

Quang DN, Arakawa Y, Hashimoto T, Asakawa Y. 2005. Lanostane triterpenoids from the inedible mushroom Fomitopsis spraguei. Phytochemistry. 66(14):1656–1661.

 PubMed Web of Science ®Google Scholar

Isaka M, Chinthanom P, Srichomthong K, Thummarukcharoen T. 2017. Lanostane triterpenoids from fruiting bodies of the bracket fungus Fomitopsis feei. Tetrahedron Lett. 58(18):1758–1761.

 Web of Science ®Google Scholar