Antimicrobial Compounds from Endolichenic Fungi

Version	Summary	Created by	Modification	Content Size	Created at	Operation
1		Priyani Ashoka Paranagama	+ 1851 word(s)	1851	2021-06-28 06:10:02	\|
2	format correction	Peter Tang	Meta information modification	1851	2021-07-06 03:35:22	\|

This entry is adapted from the peer-reviewed paper 10.3390/molecules26133901

A lichen is a symbiotic relationship between a fungus and a photosynthetic organism, which is algae or cyanobacteria. Endolichenic fungi are a group of microfungi that resides asymptomatically within the thalli of lichens. Endolichenic fungi can be recognized as luxuriant metabolic artists that produce propitious bioactive secondary metabolites.

endolichenic fungi antibacterial antifungal antiviral antiplasmodial secondary metabolites

1. Introduction

Thousands of microorganisms, including fungi and bacteria, often associate with living and dead plant tissues ^[1]. Oftentimes, the importance of these microorganisms is unobserved; only the saprotrophic and pathogenic relationships are being investigated, and are viewed as a troublesome group of organisms. However, there are groups of micro-organisms that are phyto-friendly and able to produce a plethora of secondary metabolites with significant biological activities that will aid them to adapt better to their surroundings ^[2]^[3].

Lichens are an amalgamation or a symbiotic partnership between a fungus and a photosynthetic organism. The heterotrophic fungal partner is termed as a “mycobiont”, while the photoautotrophic “photobiont”, could be either green algae or cyanobacteria ^[4]^[5]^[6]. As the mycobiont usually plays the more prominent member, lichens have traditionally exhibited characteristics similar to theirs. The two partners share water, nutrients and gases ^[6] and this mutualism allows the lichens to develop under extremely exceptional ecological conditions like deserts, rocky coasts, alpine zones and droughts ^[5]^[6]^[7]^[8]. Living under these unusual conditions enables lichens to give birth to a variety of luxurious compounds with complex structures and numerous bioactivities, making this a highly interesting stream for natural product chemists to pursue ^[8]^[9]^[10]. However, lichen flora is less abundant in the neighbourhood of urban and industrialized areas, as lichens are easily affected by air pollutants ^[11]. Lichens display a wide distribution of more than 20,000 different species worldwide ^[12], and have been utilized on various occasions in the past, such as in food, perfumes, dyes and as antidotes for folk medication ^[10]^[11].

2. Antimicrobial Compounds Extracted from Endolichenic Fungi

The need for new antimicrobial drugs is enhanced by the emergence of microbial resistance against almost all the currently available antibiotics and the sudden appearance of deadly viral infections ^[13]. Discovery of novel antimicrobial drugs was speculated as a solution to the growing threat of antibiotic-resistant microorganisms by the former secretary general of the United Nations, Ban Ki-Moon, at the UN General Assembly in 2016 ^[14].

The significant role of fungal species in producing antibiotics is elicited after the discovery of Penicillin G in 1928 ^[7]. Symbiotic fungal species like endophytic fungi are known to produce a plethora of antimicrobial compounds pertinent in therapeutics and agriculture ^[15]. Similar to other symbiotic fungi, ELF produces several secondary metabolites, which protect the lichen from biotic as well as abiotic stress ^[16]. ELF-derived antimicrobial compounds are one such group of metabolites essential to overcome the constant microbial threats faced by lichens. In some cases, extracts or natural products isolated from ELF show strong antimicrobial properties even though these bioactivities are not naturally observed within their ecological niche.

The discovery of many antimicrobial metabolites from ELF, establishes a hopeful satisfaction to the perpetual thirst for new antimicrobial drugs. However, these compounds might need further optimizations to modify their pharmacological and toxicological profiles. On the other hand, the development of synthetic pathways to produce these compounds, an industrial scale is essential to minimize the cost of production and minimize the environmental impacts. Thus, a detailed summary is provided here to describe the antimicrobial compounds isolated from ELF, including their sources, structures, activities and potencies in antimicrobial drug discovery.

Addressing the aforesaid requirement, Table 1 of this review provides an overview of antimicrobial secondary metabolites isolated from ELF, which includes 31 antibacterial compounds, 58 antifungal compounds, two antiviral compounds, and one antiplasmodial (antimalarial) compound. The structures of these compounds are given in the Figure 1. Most of the authors have either reported only the antimicrobial properties of the lichenic and endolichenic fungal extracts without isolation of the metabolites responsible for the relevant bioactivity or have not quantified it in the form of Minimum Inhibitory Concentration (MIC) or IC₅₀. However, only the endolichenic fungal secondary metabolites, whose antimicrobial properties are satisfactorily quantified, are summarized in this review. For ease of comparison, all of the antimicrobial potencies are presented in µg/mL and activities of the positive control are also given wherever available.

Figure 1. Structures of the antimicrobial compounds isolated from ELF.

Table 1. Antimicrobial Compounds Isolated from ELF.

Lichen	Endolichenic Fungi	No.	Compound	Microorganism	Activity (µg/mL)	Positive Control	Activity (µg/mL)	Reference
Diorygma hieroglyphicum	Talaromyces funiculosus	1	Funiculosone	Escherichia coli	IC₅₀ = 25	-	-	^[17]
		1	Funiculosone	Staphylococcus aureus	IC₅₀ = 58	-	-
		2	Mangrovamide J	Escherichia coli	IC₅₀ = 65	-	-
		2	Mangrovamide J	Staphylococcus aureus	IC₅₀ = 104	-	-
		3	Ravenilin	Escherichia coli	IC₅₀ = 23	-	-
				Pseudomonas aeruginosa	IC₅₀ = 96	-	-
				Staphylococcus aureus	IC₅₀ = 25	-	-
Everniastrum sp.	Ulocladium sp.	4	6-hydroxy-8-methoxy-3a-methyl-3a,9b-dihydro-3H-furo[3,2-c]isochromene-2,5-dione	Bacillus subtilis	IC₅₀ = 25.0	Gentamicin	IC₅₀ < 0.048	^[18]
		5	6-O-methylnorlichexanthone	Bacillus subtilis	IC₅₀ = 0.39
		6	Altenusin	Bacillus subtilis	IC₅₀ = 11.3
		7	Alterlactone	Bacillus subtilis	IC₅₀ = 11.8
		8	Griseoxanthone C	Bacillus subtilis	IC₅₀ = 0.35
		9	Isoaltenuene	Bacillus subtilis	IC₅₀ = 14.7
		10	Norlichexanthone	Bacillus subtilis	IC₅₀ = 0.58
		10	Norlichexanthone	Methicillin Resistant Staphylococcus aureus.	IC₅₀ = 5.4	Vancomycin	IC₅₀ < 1.03
		11	Tricycloalternarene 1b	Bacille Calmette-Guérin strain	MIC = 125	-	-	^[19]
	Ulocladium sp. (CHMCC 5507)	12	Ophiobolin P	Bacillus subtilis	MIC = 12.6	Gentamicin	MIC = 0.05	^[20]
		12	Ophiobolin P	Methicillin Resistant Staphylococcus aureus.	MIC = 25.1	Vancomycin	MIC = 1.0
		13	Ophiobolin T	Bacille Calmette-Guérin strain	MIC = 12.7	Hygromycin	MIC = 0.35
				Bacillus subtilis	MIC = 6.3	Gentamicin	MIC = 0.05
				Methicillin Resistant Staphylococcus aureus	MIC = 12.7	Vancomycin	MIC = 1.0
Parmelinella wallichiana	Nigrospora sphaerica	14	Alternariol	Bacillus subtilis	MIC = 31.2	Amikacin sulfate	MIC = 0.45	^[21]
				Escherichia coli	MIC = 62.5		MIC = 0.90
				Staphylococcus aureus	MIC = 62.5		MIC = 0.90
		15	Alternariol-9-methyl ether	Bacillus subtilis	MIC = 62.5		MIC = 0.45
				Pseudomonas fluorescens	MIC = 31.2		MIC = 0.90
				Staphylococcus aureus	MIC = 62.5		MIC = 0.90
Parmotrema rampoddense	Fusarium proliferatum	16	Acetyl tributyl citrate	Klebsiella pneumoniae	MIC = 125	-	-	^[22]
				Pseudomonas aeruginosa	MIC = 125	-	-
				Staphylococcus aureus	MIC = 125	-	-
		17	Fusarubin	Escherichia coli	MIC = 1.56	-	-
				Pseudomonas aeruginosa	MIC = 1.56	-	-
				Staphylococcus aureus	MIC = 1.56	-	-
Parmotrema ravum	Aspergillus niger	18	Asperpyrone A	Staphylococcus aureus MTCC 737	IC₅₀ = 112	-	-	^[23]
		19	Aurasperone A	Dickeya solani GBBC 1502	IC₅₀ = 63	-	-
				Listeria innocua LMG11387	IC₅₀ = 141	-	-
				Pectobacterium sp.	IC₅₀ = 76	-	-
				Pseudomonas aeruginosa MTCC 424	IC₅₀ = 160	-	-
				Pseudomonas syringae pv. Maculicola I11004	IC₅₀ = 80	-	-
				Staphylococcus aureus MTCC 737	IC₅₀ = 135	-	-
		20	Carbonarone A	Dickeya solani GBBC 1502	IC₅₀ = 88	-	-
		21	Fonsecinone A	Escherichia coli MTCC 443	IC₅₀ = 47	-	-
				Pseudomonas syringae pv. Maculicola I11004	IC₅₀ = 154	-	-
				Staphylococcus aureus MTCC 738	IC₅₀ = 120	-	-
		22	Pyrophen	Aeromonas hydrophila ATCC 7966	IC₅₀ = 78	-	-
				Listeria innocua LMG11387	IC₅₀ = 86	-	-
				Micrococcus luteus DPMB3	IC₅₀ = 63	-	-
Sticta fuliginosa	Xylariaceae sp. (CR1546C)	23	(R)-4,6,8-trihydroxy-3,4-dihydro-1(2H)-naphthalenone	Bacillus subtilis	IC₅₀ = 104.2	Streptomycin sulphate	IC₅₀ = 5.2	^[24]
		24	18-O-acetylambuic acid	Staphylococcus aureus ATCC 6538	IC₅₀ = 10.9	Antimicrobial peptide (AMP)		^[25]
		25	6,8-dihydroxy-(3R)-(2-oxopropyl)-3,4-dihydroisocoumarin	Bacillus subtilis	IC₅₀ = 106.4	Streptomycin sulphate	IC₅₀ = 5.2	^[24]
		26	Ambuic acid	Staphylococcus aureus ATCC 6538	IC₅₀ = 15.4	Antimicrobial peptide (AMP)		^[25]
Usnea sp.	Hypoxylon fuscum	27	16-α-D-mannopyranosyloxyisopimar-7-en-19-oic acid	Staphylococcus aureus CGMCC 1.2465	MIC = 46.4	Vancomycin Hydrochloride	MIC = 3.12	^[26]
		28	8-methoxy-1-naphthyl-β-glucopyranoside	Staphylococcus aureus CGMCC 1.2465	MIC = 30.1
		29	Phomol	Staphylococcus aureus CGMCC 1.2465	MIC = 21.1
-	Coniochaeta sp.	30	Coniothienol A	Enterococcus faecalis (CGMCC 1.2535)	IC₅₀ = 4.89	Ampicillin	IC₅₀ = 2.61	^[27]
		30	Coniothienol A	Enterococcus faecium (CGMCC 1.2025)	IC₅₀ = 2.00		IC₅₀ = 0.51
		31	Coniothiepinols A	Enterococcus faecalis (CGMCC 1.2535)	IC₅₀ = 11.51		IC₅₀ = 2.61
		31	Coniothiepinols A	Enterococcus faecium (CGMCC 1.2025)	IC₅₀ = 3.93		IC₅₀ = 0.51
Cetraria islandica	Myxotrichum sp.	32	Myxodiol A	Candida albicans SC 5314	MIC = 128	Fluconazole	MIC = 2	^[28]
	Pestalotiopsis sp.	33	Ambuic acid derivative 1	Fusarium oxysporum	MIC = 8	Ketoconazole	MIC = 8	^[29]
		34	Ambuic acid derivative 2	Fusarium oxysporum	MIC = 32		MIC = 8
		35	Ambuic acid derivative 4	Verticillium dahlia	MIC = 32		MIC = 1
		36	Ambuic acid derivative 5	Fusarium gramineum	MIC = 8		MIC = 8
				Fusarium oxysporum	MIC = 8		MIC = 8
				Verticillium dahlia	MIC = 16		MIC = 1
		37	Ambuic acid derivative 6	Fusarium gramineum	MIC = 8		MIC = 8
		38	Ambuic acid derivative 7	Rhizoctonia solani	MIC = 32		MIC = 8
		39	Ambuic acid derivative 8	Rhizoctonia solani	MIC = 32		MIC = 8
		40	Ambuic acid derivative 9	Fusarium gramineum	MIC = 32		MIC = 8
		40	Ambuic acid derivative 9	Fusarium oxysporum	MIC = 16		MIC = 8
		41	Ambuic acid derivative 11	Fusarium gramineum	MIC = 32		MIC = 8
Cetrelia sp.	Aspergillus sp. CPCC 400810	42	Isocoumarindole A	Candida albicans	MIC = 32.0	Caspofungin	MIC = 0.03	^[30]
Diorygma hieroglyphicum	Talaromyces funiculosus	1	Funiculosone	Candida albicans	IC₅₀ = 35	-	-	^[17]
Everniastrum sp.	Ulocladium sp.	43	7-hydroxy-3-(2-hydroxy-propyl)-5-methyl-isochromen-1-one	Candida albicans SC 5314	IC₅₀ = 45.4	Amphotericin B	IC₅₀ = 1.03	^[18]
		44	7-hydroxy-3,5-dimethyl-isochromen-1-one	Candida albicans SC 5314	IC₅₀ = 18.7		IC₅₀ = 1.03
		6	Altenusin	Aspergillus fumigatus	IC₅₀ = 57.5		IC₅₀ = 0.74
		8	Griseoxanthone C	Candida albicans SC 5314	IC₅₀ = 40.6		IC₅₀ = 1.03
		10	Norlichexanthone	Aspergillus fumigatus	IC₅₀ = 43.6		IC₅₀ = 0.74
		45	Rubralactone	Aspergillus fumigatus	IC₅₀ = 63.3		IC₅₀ = 0.74
		45	Rubralactone	Candida albicans SC 5314	IC₅₀ = 54.7		IC₅₀ = 1.03
Lethariella zahlbruckner	Tolypocladium cylindrosporum	46	Pyridoxatin	Candida albicans (Multiple strains)	MIC = 0.5 − 8.0	Fluconazole	MIC = 1.0 − 2.0	^[31]
				Candida glabrata (Multiple strains)	MIC = 1.0 − 8.0		MIC = 1.0 − 2.0
				Candida krusei (Multiple strains)	MIC = 1.0 − 4.0		MIC = 1.0 − 2.0
				Candida tropicalis CT2	MIC = 32		MIC = 2.0
Lobaria quercizans	Aspergillus versicolor	47	3,7-dihydroxy-1,9-dimethyldibenzofuran	Candida albicans	MIC = 64	Fluconazole	MIC = 2	^[32]
		48	Cordyol C	Candida albicans	MIC = 8
		49	Diorcinol D	Candida albicans	MIC = 8
		50	Diorcinol I	Candida albicans	MIC = 32
		51	Violaceol I	Candida albicans	MIC = 8
		52	Violaceol II	Candida albicans	MIC = 8
Parmelia sp.	Periconia sp.	53	3-(2-oxo-2H-pyran-6-yl)propanoic acid	Aspergillus niger	MIC = 31	Cycloheximide	MIC < 16	^[33]
		54	Pericocin A	Aspergillus niger	MIC = 31	Cycloheximide	MIC < 16
		55	Pericocin B	Aspergillus niger	MIC = 31
		56	Pericocin C	Aspergillus niger	MIC = 31
		57	Pericocin D	Aspergillus niger	MIC = 31
		58	Pericoterpenoid A	Aspergillus niger	MIC = 31			^[34]
	Tolypocladium sp. (4259a)	46	Pyridoxatin	Candida albicans	MIC = 0.5	-	-	^[35]
Parmelinella wallichiana	Nigrospora sphaerica	14	Alternariol	Candida albicans	MIC = 80.0	Ketoconazole	MIC = 1.90	^[21]
Parmotrema ravum	Aspergillus niger	59	Aspergyllone	Candida parapsilosis	IC₅₀ = 52	-	-	^[23]
		19	Aurasperone A	Candida krusei MTCC 9215	IC₅₀ = 373	-	-
		20	Carbonarone A	Candida albicans MTCC 227	IC₅₀ = 103	-	-
		20	Carbonarone A	Candida krusei MTCC 9215	IC₅₀ = 31	-	-
		22	Pyrophen	Candida albicans MTCC 227	IC₅₀ = 74	-	-
				Candida glabrata	IC₅₀ = 97	-	-
				Candida utilis IHEM 400	IC₅₀ = 62	-	-
Pseudosyphellaria sp.	Biatriospora sp.	60	2-acetonyl-3-methyl-5-hydroxy-7-methoxynaphthazarin	Candida albicans	MIC = 64	Fluconazole	MIC = 2	^[36]
		61	6-deoxy-7-O-demethyl-3,4-anhydrofusarubin	Candida albicans	MIC = 32
		62	Biatriosporin D	Candida albicans	MIC = 16
		63	Biatriosporin K	Candida albicans	MIC = 64
Sticta fuliginosa	Xylariaceae sp. (CR1546C)	64	(3R,4S)-3,4,8-trihydroxy-3,4-dihydro-1(2H)-naphthalenone	Candida albicans	IC₅₀ = 63.2	Amphotericin B	IC₅₀ = 1.3	^[24]
		65	(3S,4S)-3,4,6,8-tetrahydroxy-3,4-dihydro-1(2H)-naphthalenone	Candida albicans	IC₅₀ = 67.8
		23	(R)-4,6,8-trihydroxy-3,4-dihydro-1(2H)-naphthalenone	Candida albicans	IC₅₀ = 78.2
		66	2,4-dihydroxy-6-(2-oxopropyl)-benzoic acid	Candida albicans	IC₅₀ = 101.3
		67	5,6,8-trihydroxy-3(R)-methyl-3,4-dihydroisocoumarin	Candida albicans	IC₅₀ = 71.4
		68	6,8-dihydroxy-(3)-(2-oxopropyl)-isocoumarin	Candida albicans	IC₅₀ = 98.1
		25	6,8-dihydroxy-(3R)-(2-oxopropyl)-3,4-dihydroisocoumarin	Candida albicans	IC₅₀ = 71.2
		69	6,8-dihydroxy-3(R)-methyl-3,4-dihydroisocoumarin	Candida albicans	IC₅₀ = 65.1
		70	6,8-dihydroxy-3-[(2S)-2-hydroxypropyl]-isocoumarin	Candida albicans	IC₅₀ = 99.1
		71	6,8-dihydroxy-3-methylisocoumarin	Candida albicans	IC₅₀ = 67.2
Umbilicaria sp.	Floricola striata	72	Floricolin A	Candida albicans	MIC = 16	-	-	^[37]
		73	Floricolin B	Candida albicans	MIC = 8	-	-
		74	Floricolin C	Candida albicans	MIC = 8	-	-
		75	Floricolin D	Candida albicans	MIC = 64	-	-
		76	Terphenyl 2	Candida albicans	MIC = 64	-	-
Usnea baileyi	Xylaria venustula	77	N-dodecyldiethanolamine (DDE)	Candida albicans NCTC713	MIC = 5.5	-	-	^[38]^[39]
		78	Piliformic acid	Colletotrichum gloeosporioides	MIC = 625.2	Captan	MIC = 5000	^[38]^[40]
		78	Piliformic acid	Colletotrichum gloeosporioides	MIC = 625.2	Difenoconazole	MIC = 8.1	^[38]^[40]
-	Coniochaeta sp.	31	Coniothiepinols A	Fusarium oxysporum (CGMCC 3.2830)	IC₅₀ = 13.12	Carbendazim	IC₅₀ = 0.44	^[27]
Parmelinella wallichiana	Nigrospora sphaerica	14	Alternariol	Herpes Simplex Virus	IC₅₀ = 34.9	-	-	^[41]
Parmelinella wallichiana	Nigrospora sphaerica	15	Alternariol-9-methyl ether	Herpes Simplex Virus	IC₅₀ = 64.0	-	-	^[41]
Usnea baileyi	Xylaria venustula	79	Isoplysin A	Plasmodium falciparum	MIC = 0.97	-	-	^[38]^[42]

3. Structural Features Which Affect the Antimicrobial Activity of the Compounds

ELF are metabolically versatile organisms that can produce secondary metabolites belonging to different natural product classes. However, by observing the structures of the compounds isolated from ELF categorized above, some common scaffolds leading to distinct antimicrobial properties can be identified. Knowledge of the bioactivities of such chemical scaffolds plays an important role in rational drug discovery and in natural product-related research to make intelligent guesses about the potentials of isolated compounds. The presence of a large pool of data about the potencies of natural compounds or their synthetic or semi-synthetic derivatives with common scaffolds will be helpful in structure–activity relationship (SAR) studies. In order to facilitate such studies, we have summarized the structural scaffolds in Table 2 that can be identified commonly among the antimicrobial compounds isolated from ELF.

Table 2. Common structural scaffolds among the antimicrobial compounds isolated from ELF.

Scaffold	Compounds
	4, 9, 14, 15, 25, 42, 43, 44, 45, 53, 54, 56, 57, 66, 67, 68, 69, 70, 71
	1, 2, 3, 5, 8, 10, 18, 19, 20, 21, 30, 31, 55, 59
	24, 26, 33, 34, 35, 36, 37, 38, 39, 40, 41
	48, 49, 50, 51, 52
	17, 61, 63
	23, 64, 65

References

Gunatilaka, A.A.L. Natural products from plant-associated microorganisms: Distribution, structural diversity, bioactivity, and implications of their occurrence. J. Nat. Prod. 2006, 69, 509–526.
Petrini, O. Fungal endophytes of tree leaves. In Microbial Ecology of Leaves; Springer: New York, NY, USA, 1991; pp. 179–197.
Strobel, G.; Daisy, B. Bioprospecting for microbial endophytes and their natural products. Microbiol. Mol. Biol. Rev. 2003, 67, 491–502.
Henskens, F.L.; Green, T.G.A.; Wilkins, A. Cyanolichens can have both cyanobacteria and green algae in a common layer as major contributors to photosynthesis. Ann. Bot. 2012, 110, 555–563.
Basnet, B.B.; Liu, H.; Liu, L.; Suleimen, Y.M. Diversity of anticancer and antimicrobial compounds from lichens and lichen-derived fungi: A systematic review (1985–2017). Curr. Org. Chem. 2018, 22, 2487–2500.
Gao, H.; Zou, J.; Li, J.; Zhao, H. Endolichenic fungi: A potential treasure trove for discovery of special structures and bioactive compounds. In Studies in Natural Products Chemistry; Atta-Ur-Rahman, Ed.; Elsevier: Amsterdam, The Netherlands, 2016; Volume 48, pp. 347–397.
Agrawal, S.; Deshmukh, S.K.; Reddy, M.S.; Prasad, R.; Goel, M. Endolichenic fungi: A hidden source of bioactive metabolites. S. Afr. J. Bot. 2020, 134, 163–186.
Boustie, J.; Tomasi, S.; Grube, M. Bioactive lichen metabolites: Alpine habitats as an untapped source. Phytochem. Rev. 2011, 10, 287–307.
Lawrey, J.D. Biological role of lichen substances. Bryologist 1986, 89, 111–122.
Shukla, V.; Joshi, G.P.; Rawat, M.S.M. Lichens as a potential natural source of bioactive compounds: A review. Phytochem. Rev. 2010, 9, 303–314.
Galloway, D.J. Biodiversity: A lichenological perspective. Biodivers. Conserv. 1992, 1, 312–323.
Lücking, R.; Hodkinson, B.P.; Leavitt, S.D. The 2016 classification of lichenized fungi in the Ascomycota and Basidiomycota-approaching one thousand genera. Bryologist 2016, 119, 361–416.
Strobel, G.; Daisy, B.; Castillo, U.; Harper, J. Natural products from endophytic microorganisms. J. Nat. Prod. 2004, 67, 257–268.
Sarasan, M.; Puthumana, J.; Job, N.; Han, J.; Lee, J.S.; Philip, R. Marine algicolous endophytic fungi-a promising drug resource of the era. J. Microbiol. Biotechnol. 2017, 27, 1039–1052.
Alwis, Y.V.; Wethalawe, A.N.; Udukala, D.N.; Paranagama, P.A. Endophytic microflora of sri lankan plants: An overview of the therapeutic and agricultural applications of the secondary metabolites. In Endophytes; Patil, R.H., Maheshwari, V.L., Eds.; Springer: Singapore, 2021; pp. 153–175.
Nguyen, K.H.; Chollet-Krugler, M.; Gouault, N.; Tomasi, S. UV-protectant metabolites from lichens and their symbiotic partners. Nat. Prod. Rep. 2013, 30, 1490–1508.
Padhi, S.; Masi, M.; Cimmino, A.; Tuzi, A.; Jena, S.; Tayung, K.; Evidente, A. Funiculosone, a substituted dihydroxanthene-1,9-dione with two of its analogues produced by an endolichenic fungus Talaromyces funiculosus and their antimicrobial activity. Phytochemistry 2019, 157, 175–183.
Wang, Q.X.; Bao, L.; Yang, X.L.; Guo, H.; Yang, R.N.; Ren, B.; Zhang, L.X.; Dai, H.Q.; Guo, L.D.; Liu, H.W. Polyketides with antimicrobial activity from the solid culture of an endolichenic fungus Ulocladium sp. Fitoterapia 2012, 83, 209–214.
Wang, Q.X.; Bao, L.; Yang, X.L.; Guo, H.; Ren, B.; Guo, L.D.; Song, F.H.; Wang, W.Z.; Liu, H.W.; Zhang, L.X. Tricycloalternarenes F-H: Three new mixed terpenoids produced by an endolichenic fungus Ulocladium sp. using OSMAC method. Fitoterapia 2013, 85, 8–13.
Wang, Q.X.; Bao, L.; Yang, X.L.; Liu, D.L.; Guo, H.; Dai, H.Q.; Song, F.H.; Zhang, L.X.; Guo, L.D.; Li, S.J.; et al. Ophiobolins P-T, five new cytotoxic and antibacterial sesterterpenes from the endolichenic fungus Ulocladium sp. Fitoterapia 2013, 90, 220–227.
Gu, W. Bioactive metabolites from Alternaria brassicicola ML-P08, an endophytic fungus residing in Malus halliana. World J. Microbiol. Biotechnol. 2009, 25, 1677–1683.
Tan, M.A.; Castro, S.G.; Oliva, P.M.P.; Yap, P.R.J.; Nakayama, A.; Magpantay, H.D.; dela Cruz, T.E.E. Biodiscovery of antibacterial constituents from the endolichenic fungi isolated from Parmotrema rampoddense. 3 Biotech 2020, 10, 1–7.
Padhi, S.; Masi, M.; Panda, S.K.; Luyten, W.; Cimmino, A.; Tayung, K.; Evidente, A. Antimicrobial secondary metabolites of an endolichenic Aspergillus niger isolated from lichen thallus of Parmotrema ravum. Nat. Prod. Res. 2020, 34, 2573–2580.
Kim, K.H.; Beemelmanns, C.; Murillo, C.; Guillén, A.; Umaña, L.; Tamayo-Castillo, G.; Kim, S.N.; Clardy, J.; Cao, S. Naphthalenones and isocoumarins from a Costa Rican fungus Xylariaceae sp. CR1546C. J. Chem. Res. 2014, 38, 722–725.
Ding, G.; Li, Y.; Fu, S.; Liu, S.; Wei, J.; Che, Y. Ambuic acid and torreyanic acid derivatives from the endolichenic fungus Pestalotiopsis sp. J. Nat. Prod. 2009, 72, 182–186.
Basnet, B.B.; Chen, B.; Suleimen, Y.M.; Ma, K.; Guo, S.; Bao, L.; Huang, Y.; Liu, H. Cytotoxic secondary metabolites from the endolichenic fungus Hypoxylon fuscum. Planta Med. 2019, 85, 1088–1097.
Wang, Y.; Niu, S.; Liu, S.; Guo, L.; Che, Y. The first naturally occurring thiepinols and thienol from an endolichenic fungus Coniochaeta sp. Org. Lett. 2010, 12, 5081–5083.
Yuan, C.; Wang, H.Y.; Wu, C.S.; Jiao, Y.; Li, M.; Wang, Y.Y.; Wang, S.Q.; Zhao, Z.T.; Lou, H.X. Austdiol, fulvic acid and citromycetin derivatives from an endolichenic fungus, Myxotrichum sp. Phytochem. Lett. 2013, 6, 662–666.
Yuan, C.; Ding, G.; Wang, H.Y.; Guo, Y.H.; Shang, H.; Ma, X.J.; Zou, Z.M. Polyketide-terpene hybrid metabolites from an endolichenic fungus Pestalotiopsis sp. Biomed Res. Int. 2017, 2017, 1–10.
Chen, M.; Wang, R.; Zhao, W.; Yu, L.; Zhang, C.; Chang, S.; Li, Y.; Zhang, T.; Xing, J.; Gan, M.; et al. Isocoumarindole A, a chlorinated isocoumarin and indole alkaloid hybrid metabolite from an endolichenic fungus Aspergillus sp. Org. Lett. 2019, 21, 1530–1533.
Chang, W.; Zhang, M.; Li, Y.; Li, X.; Gao, Y.; Xie, Z.; Lou, H. Lichen endophyte derived pyridoxatin inactivates Candida growth by interfering with ergosterol biosynthesis. Biochim. Biophys. Acta Gen. Subj. 2015, 1850, 1762–1771.
Li, X.; Zhou, Y.; Zhu, R.; Chang, W.; Yuan, H. Identification and biological evaluation of secondary metabolites from the endolichenic fungus Aspergillus versicolor. Chem. Biodivers. 2015, 12, 575–592.
Wu, Y.H.; Xiao, G.K.; Chen, G.D.; Wang, C.X.; Hu, D.; Lian, Y.Y.; Lin, F.; Guo, L.D.; Yao, X.S.; Gao, H. Pericocins A-D, new bioactive compounds from Periconia sp. Nat. Prod. Commun. 2015, 10, 2127–2130.
Wu, Y.H.; Chen, G.D.; Wang, C.X.; Hu, D.; Li, X.X.; Lian, Y.Y.; Lin, F.; Guo, L.D.; Gao, H. Pericoterpenoid A, a new bioactive cadinane-type sesquiterpene from Periconia sp. J. Asian Nat. Prod. Res. 2015, 17, 671–675.
Hu, C.H.; Zhou, Y.H.; Xie, F.; Li, Y.L.; Zhao, Z.T.; Lou, H.X. Two new α-pyrone derivatives from an endolichenic fungus Tolypocladium sp. J. Asian Nat. Prod. Res. 2017, 19, 786–792.
Zhou, Y.H.; Zhang, M.; Zhu, R.X.; Zhang, J.Z.; Xie, F.; Li, X.B.; Chang, W.Q.; Wang, X.N.; Zhao, Z.T.; Lou, H.X. Heptaketides from an endolichenic fungus Biatriospora sp. and their antifungal activity. J. Nat. Prod. 2016, 79, 2149–2157.
Li, W.; Gao, W.; Zhang, M.; Li, Y.L.; Li, L.; Li, X.B.; Chang, W.Q.; Zhao, Z.T.; Lou, H.X. P-Terphenyl derivatives from the endolichenic fungus Floricola striata. J. Nat. Prod. 2016, 79, 2188–2194.
Santiago, K.A.A.; Edrada-Ebel, R.; Dela Cruz, T.E.E.; Cheow, Y.L.; Ting, A.S.Y. Biodiscovery of potential antibacterial diagnostic metabolites from the endolichenic fungus Xylaria venustula using LC–MS-based metabolomics. Biology 2021, 10, 191.
Lambert, P.A.; Smith, A.R.W. The mode of action of N-(n-dodecyl)diethanolamine with particular reference to the effect of protonation on uptake by Escherichia coli. J. Gen. Microbiol. 1977, 103, 367–374.
Elias, L.M.; Fortkamp, D.; Sartori, S.B.; Ferreira, M.C.; Gomes, L.H.; Azevedo, J.L.; Montoya, Q.V.; Rodrigues, A.; Ferreira, A.G.; Lira, S.P. The potential of compounds isolated from Xylaria spp. as antifungal agents against anthracnose. Brazilian J. Microbiol. 2018, 49, 840–847.
He, J.W.; Chen, G.D.; Gao, H.; Yang, F.; Li, X.X.; Peng, T.; Guo, L.D.; Yao, X.S. Heptaketides with antiviral activity from three endolichenic fungal strains Nigrospora sp., Alternaria sp. and Phialophora sp. Fitoterapia 2012, 83, 1087–1091.
Bialonska, D.; Zjawiony, J.K. Aplysinopsins—marine indole alkaloids: Chemistry, bioactivity and ecological significance. Mar. Drugs 2009, 7, 166–183.

© Text is available under the terms and conditions of the Creative Commons Attribution (CC BY) license; additional terms may apply. By using this site, you agree to the Terms and Conditions and Privacy Policy.

Upload a video for this entry

Information

Subjects: Biochemistry & Molecular Biology

Contributor MDPI registered users' name will be linked to their SciProfiles pages. To register with us, please refer to https://encyclopedia.pub/register :

Priyani Ashoka Paranagama

View Times: 439

Update Date: 06 Jul 2021

Table of Contents

Video Upload Options

Confirm

1. Introduction

2. Antimicrobial Compounds Extracted from Endolichenic Fungi

3. Structural Features Which Affect the Antimicrobial Activity of the Compounds

References