Submitted Successfully!
To reward your contribution, here is a gift for you: A free trial for our video production service.
Thank you for your contribution! You can also upload a video entry or images related to this topic.
Version Summary Created by Modification Content Size Created at Operation
1 + 1851 word(s) 1851 2021-06-28 06:10:02 |
2 format correction Meta information modification 1851 2021-07-06 03:35:22 |

Video Upload Options

Do you have a full video?

Confirm

Are you sure to Delete?
Cite
If you have any further questions, please contact Encyclopedia Editorial Office.
Paranagama, P.A. Antimicrobial Compounds from Endolichenic Fungi. Encyclopedia. Available online: https://encyclopedia.pub/entry/11681 (accessed on 15 June 2024).
Paranagama PA. Antimicrobial Compounds from Endolichenic Fungi. Encyclopedia. Available at: https://encyclopedia.pub/entry/11681. Accessed June 15, 2024.
Paranagama, Priyani Ashoka. "Antimicrobial Compounds from Endolichenic Fungi" Encyclopedia, https://encyclopedia.pub/entry/11681 (accessed June 15, 2024).
Paranagama, P.A. (2021, July 05). Antimicrobial Compounds from Endolichenic Fungi. In Encyclopedia. https://encyclopedia.pub/entry/11681
Paranagama, Priyani Ashoka. "Antimicrobial Compounds from Endolichenic Fungi." Encyclopedia. Web. 05 July, 2021.
Antimicrobial Compounds from Endolichenic Fungi
Edit

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]

Staphylococcus aureus

IC50 = 58

-

-

2

Mangrovamide J

Escherichia coli

IC50 = 65

-

-

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

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]

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]

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

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

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

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

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

-

-

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]

Difenoconazole

MIC = 8.1

-

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]

15

Alternariol-9-methyl ether

Herpes Simplex Virus

IC50 = 64.0

-

-

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

Molecules 26 03901 i001

4, 9, 14, 15, 25, 42, 43, 44, 45, 53, 54, 56, 57, 66, 67, 68, 69, 70, 71

Molecules 26 03901 i002

1, 2, 3, 5, 8, 10, 18, 19, 20, 21, 30, 31, 55, 59

Molecules 26 03901 i003

24, 26, 33, 34, 35, 36, 37, 38, 39, 40, 41

Molecules 26 03901 i004

48, 49, 50, 51, 52

Molecules 26 03901 i005

17, 61, 63

Molecules 26 03901 i006

23, 64, 65

References

  1. 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.
  2. Petrini, O. Fungal endophytes of tree leaves. In Microbial Ecology of Leaves; Springer: New York, NY, USA, 1991; pp. 179–197.
  3. Strobel, G.; Daisy, B. Bioprospecting for microbial endophytes and their natural products. Microbiol. Mol. Biol. Rev. 2003, 67, 491–502.
  4. 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.
  5. 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.
  6. 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.
  7. 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.
  8. Boustie, J.; Tomasi, S.; Grube, M. Bioactive lichen metabolites: Alpine habitats as an untapped source. Phytochem. Rev. 2011, 10, 287–307.
  9. Lawrey, J.D. Biological role of lichen substances. Bryologist 1986, 89, 111–122.
  10. 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.
  11. Galloway, D.J. Biodiversity: A lichenological perspective. Biodivers. Conserv. 1992, 1, 312–323.
  12. 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.
  13. Strobel, G.; Daisy, B.; Castillo, U.; Harper, J. Natural products from endophytic microorganisms. J. Nat. Prod. 2004, 67, 257–268.
  14. 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.
  15. 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.
  16. 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.
  17. 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.
  18. 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.
  19. 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.
  20. 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.
  21. Gu, W. Bioactive metabolites from Alternaria brassicicola ML-P08, an endophytic fungus residing in Malus halliana. World J. Microbiol. Biotechnol. 2009, 25, 1677–1683.
  22. 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.
  23. 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.
  24. 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.
  25. 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.
  26. 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.
  27. 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.
  28. 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.
  29. 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.
  30. 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.
  31. 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.
  32. 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.
  33. 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.
  34. 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.
  35. 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.
  36. 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.
  37. 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.
  38. 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.
  39. 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.
  40. 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.
  41. 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.
  42. Bialonska, D.; Zjawiony, J.K. Aplysinopsins—marine indole alkaloids: Chemistry, bioactivity and ecological significance. Mar. Drugs 2009, 7, 166–183.
More
Information
Contributor MDPI registered users' name will be linked to their SciProfiles pages. To register with us, please refer to https://encyclopedia.pub/register :
View Times: 475
Revisions: 2 times (View History)
Update Date: 06 Jul 2021
1000/1000
Video Production Service