Fungal isolate

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Fungal isolates have been researched for decades. Because fungi often exist in thin mycelial monolayers, with no protective shell, immune system, and limited mobility, they have developed the ability to synthesize a variety of unusual compounds for survival. Researchers have discovered fungal isolates with anticancer, antimicrobial, immunomodulatory, and other bio-active properties. The first statins, β-Lactam antibiotics, as well as a few important antifungals, were discovered in fungi.

Contents

Chemotherapeutic isolates

BMS manufactures paclitaxel using Penicillium and plant cell fermentation. Fungi can synthesize podophyllotoxin and camptothecin, precursors to etoposide, teniposide, topotecan, and irinotecan.

Lentinan, PSK, and PSP, are registered anticancer immunologic adjuvants. Irofulven and acylfulvene are anticancer derivatives of illudin S. Clavaric acid is a reversible farnesyltransferase inhibitor. Inonotus obliquus creates betulinic acid precursor betulin. Flammulina velutipes creates asparaginase. Plinabulin is a fungal isolate derivative currently being researched for anticancer applications.

Cholesterol inhibitors

The statins lovastatin, mevastatin, and simvastatin precursor monacolin J, are fungal isolates. Additional fungal isolates that inhibit cholesterol are zaragozic acids, eritadenine, and nicotinamide riboside.

Immunosuppressants

Ciclosporin, mycophenolic acid, mizoribine, FR901483, and gliotoxin, are immunosuppressant fungal isolates.

Antimicrobials

Penicillin, cephalosporins, fusafungine, usnic acid, fusidic acid, fumagillin, brefeldin A, verrucarin A, alamethicin, are antibiotic fungal isolates. Antibiotics retapamulin, tiamulin, and valnemulin are derivatives of the fungal isolate pleuromutilin. Griseofulvin, echinocandins, strobilurin, azoxystrobin, caspofungin, micafungin, are fungal isolates with antifungal activity.

Psychotropic isolates

The headache medications cafergot, dihydroergotamine, methysergide, methylergometrine, the dementia medications hydergine, nicergoline, the Parkinson's disease medications lisuride, bromocriptine, cabergoline, and pergolide were all derived from Claviceps isolates. Polyozellus multiplex synthesizes prolyl endopeptidase inhibitors polyozellin, thelephoric acid, and kynapcins. Boletus badius synthesizes L-theanine.

Other isolates

Vitamin D biosynthesis in fungi and animals.svg

Researchers have discovered other interesting fungal isolates like the antihyperglycemic compounds ternatin, aspergillusol A, sclerotiorin, and antimalarial compounds codinaeopsin, efrapeptins, and antiamoebin. The fungal isolate ergothioneine is actively absorbed and concentrated by the human body via SLC22A4. Other notable fungal isolates include vitamin D1, vitamin D2, and vitamin D4.

IsolateSourceResearched activity / Chemical description
9-Deacetoxyfumigaclavine C endophytic Aspergillus fumigatuspotent, selective, anticancer activity comparable to doxorubicin (IC50 = 3.1 μM against K562) [1]
14-Norpseurotin A Aspergillusantiparasitic/anticancer [1]
3-O-Methylfunicone Penicillium pinophilum in vitro cancer stem cell inhibitor
Anicequol Penicillium aurantiogriseum in vitro anchorage-independent cancer inhibitor
Anomalin Asponge-derived Arthrinium angiogenesis inhibitor
Antiamoebin Emericellopsis anti-microbial/protozoan polypeptide
Arugosin C Aspergillus versicolor isolated from Red Sea green algabio-active anthraquinone [2]
Aspergillides A-Cmarine Aspergillus ostianusanticancer/cytotoxic
Aspergillusene "sea fan"-derived Aspergillus sydowii antioxidant sesquiterpene
Aspergilone A"sea fan"-derived Aspergillusanticancer and antifouling activity [3]
Aspergillusol A marine Aspergillus alpha-glucosidase inhibitor
Asperterrestide Amarine Aspergillus terreuscytotoxic and antiviral cyclic tetrapeptide
Asterric acid Antarctic Geomyces endothelin binding inhibitor
Auranthine Penicillium antimicrobial
Aurantiamine Penicillium aurantiogriseumvaline and histidine derived diketopiperazine
Aurantiomide sponge-derived Penicillium aurantiogriseum quinazoline alkaloid with cytotoxic/anticancer activity
Berkeleydione fungal extremophile (Berkeley Pit, Montana)anticancer polyketide-terpenoid
Berkeleytrione fungal extremophile (Berkeley Pit, Montana)anticancer polyketide-terpenoid
Berkelic acid fungal extremophile (Berkeley Pit, Montana)spiroketal anticancer compound
beta-Ergocryptine ergot dopaminergic ergot alkaloid
Bisvertinolone Trichoderma anticancer [4]
Botryodiplodin Penicillium antibiotic mycotoxin
Botryosphaeran Botryosphaeria rhodina free-radical scavenging and antioxidant [5]
Brevianamide Smarine Aspergillus versicolorantimicrobial dimeric diketopiperazine
Brevicompanines D-Hdeep ocean sediment Penicilliumlipopolysaccharide (LPS)-induced nitric oxide inhibitor
Cephalosporolide marine Penicillium novel lactones
Chaetoglobosin A Chaetomium anticancer [6]
Chaetoxanthone marine-derived Chaetomium bio-active xanthone
Chanoclavine ergot dopamine agonist
Chanoclavine II ergot
Chetracins BAntarctic psychrophilic Oidiodendron truncatumin vitro anticancer (nanomolar)
Chrysophanic acid antiviral/anticancer anthraquinone
Chrysosporide Sepedonium chrysospermum
Citreorosein Penicilliumantimicrobial polyketide
Citrinolactone Dmarine-derived Penicillium citrinin derivative
Citromycetin Australian Penicilliumbio-active polyketide
Citromycin Penicilliumantibiotic
Communesin B Mediterranean Axinella -derived Penicilliumanticancer
Costaclavin ergot
Cryptoechinuline Dmangrove rhizosphere soil-derived Aspergillusanticancer
Curvularin Penicilliumantimicrobial
Cycloprop-2-ene carboxylic acid Russula subnigricans causes rhabdomyolysis [7]
Decumbenone Cmarine Aspergillus sulphureusanticancer
Dehydroaltenusin Alternaria tenuis inhibitor of mammalian DNA polymerase α
Dehydrocurvularin Penicilliumantimicrobial
Disydonols A-Cmarine Aspergillusanticancer
Duclauxin Penicillium duclauxianticancer [8]
Epicoccins Cordyceps -colonizing Epicoccum nigrum antiviral
Epolactaene marine fungusantiinflammatory, inhibitory activity of DNA polymerases and DNA topoisomerase II, active synthetic analogs [9]
Epoxyagroclavine permafrost Penicillium ergot alkaloid
Epoxyphomalins A-Bmarine Paraconiothyriumpotent cytotoxics
Ergosine ergot dopaminergic ergot alkaloid
Ergostane mushrooms steroid
Ergostine ergot alpha-adrenergic blocking, vasoconstrictive ergot alkaloid
Eupenifeldin Eupenicillium brefeldianumantimicrobial cytotoxic bistropolone
Evariquinone Emericella variecolor (derived from the marine sponge Haliclona )
Fecosterol fungi and lichens steroid
Fellutanine Penicilliumbio-active diketopiperazine alkaloids
Festuclavine Aspergillus fumigatusbio-active ergoline
Fumigaclavine A endophytic Aspergillusbio-active ergoline
Fumigaclavine B endophytic Aspergillusbio-active ergoline
Fumigaclavine C endophytic Aspergillusbio-active ergoline
Fumiquinazoline soft coral Sinularia -derived Aspergillus fumigatuscytotoxic/anticancer
Fungisterol Cordyceps sinensis steroid
Glionitrin A mine-dwelling Aspergillus fumigatusantibiotic-anticancer
Glionitrin BAspergillus fumigatus KMC-901anticancer diketopiperazine
HymenosetinHymenoscyphus pseudoalbidusantimicrobial (active against MRSA) [10]
Integrasone Unknowninhibits HIV-1 integrase enzyme [11]
Isoemericellin marine Emericella variecolor
Leporizines A-CAspergilluscytotoxic epithiodiketopiperazines
Leptosphaerin marine Leptosphaeria oraemarisantifungal
Lichesterol fungi and lichens steroid
Luteoalbusins A-Bdeep sea Acrostalagmus luteoalbusanticancer indole diketopiperazines
Luteusin A Talaromyces luteus monoamine oxidase inhibitor
Malettinin Hypoxylon polyketide/antimicrobial
Maximiscin Tolypocladium (Salcha, Alaska) [12] anticancer polyketide-shikimate compound
Meleagrin deep ocean Penicilliumanticancer
Methylenolactocin Penicilliumanticancer
Neoxaline Aspergillus japonicus antimitotic and antiplatelet
Nigerapyrones A-Emarine mangrove-derived, endophytic Aspergillus nigeranticancer
Nigrosporin B Nigrosporaantimicrobial
Nocapyrones E-GNocardiopsis dassonvilleiantimicrobial alpha-pyrones
Notoamide marine Aspergillusbio-active prenylated indole alkaloid
Oxaline Penicillium oxalicum and Aspergillus japonicusanticancer (tubulin polymerization inhibitor), O-methylated derivative of meleagrin
Pencolide seaweed-derived endophytic fungibio-active maleimide
Penicitrinol Jmarine-derived Penicillium bio-active citrinin dimer
Penicitrinol Kmarine-derived Penicillium bio-active citrinin derivative
Penicitrinone Emarine-derived Penicillium bio-active citrinin dimer
Penochalasin A endophytic Chaetomium cytotoxic/anticancer cytochalasan-based alkaloid
Penostatin A Penicilliumcytotoxic metabolite
Pestalamides A-CPestalotiopsis theaeantiviral and antifungal
Petrosifungin sponge-derived Penicillium brevicompactumnovel cyclodepsipeptide
Phillyrin endophytic fungus (isolated from Forsythia )antiobesity
Piscarinine Penicillium piscarium westlingbio-active polycyclic diketopiperazine alkaloid
Prenylterphenyllinsmarine Aspergillus candidusanticancer
Protuboxepins A and BAspergillus SF-5044anticancer diketopiperazines
Pseurotin A endophytic Aspergillusantiparasitic and anticancer
Pyrenocine marine Penicillium paxilli antibiotic/antiinflammatory mycotoxin [13]
Questiomycin A Penicillium expansum antibiotic
Quinocitrinine permafrost Penicillium quinoline alkaloid
RES-1149-2Aspergillusnon-peptidic endothelin receptor antagonist
Retigeric acid B Lobaria (lichen)anticancer
Rubratoxin B Penicillium rubrumanticancer
Rugulovasine Penicillium
Sch 642305 Penicillium verrucosum and Rhizoctonia solanibacterial DNA primase inhibitor
Sclerotides A-BAspergillus sclerotiorum PT06-1bio-active cyclic hexapeptides
Secalonic acid marine funginootropic
Shamixanthone Aspergillusbio-active prenylated xanthone
Shearinine marine Penicillium janthinellumanticancer
Siderin Aspergillus versicolor isolated from Red Sea green algabio-active anthraquinone
Sorbicillactone A sponge-derived fungusnovel bio-active alkaloid
Spiculisporic acid marine Aspergillusbioactive γ-butenolide
Spiropreussione Preussia anticancer
Stephacidin Aspergillus ochraceus WC76466anticancer/cytotoxic
Stromemycin marine Emericella C-glycosidic depside matrix metalloproteinase inhibitor
Terpestacin endophytic fungus Drechslera raveneliianticancer
Terrestrolsmarine Penicillium terrestrecytotoxic/anticancer [14]
Terreulactone A Aspergillus terreusanti-acetylcholinesterase terpenoid
Topopyrone C Phoma and Penicilliumanticancer human topoisomerase I inhibitor
Trachyspic acid Talaromyces trachyspermus heparanase inhibitor
Trichodimerol Trichoderma bio-active pentacycle
Ustusolatesmarine Aspergillus ustusanticancer
Variecolactone Emericella purpurea myceliumimmunomodulatory sesterterpene
Variecolol Emericella aurantio-brunneaimmunosuppressant/antiviral alkaloid
Varixanthone marine Emericella variecolorantimicrobial
Vermiculine Penicillium vermiculatumantibiotic
Vermistatin fungal extremophile (Berkeley Pit, Montana)anticancer [15]
Vermixocin Penicillium vermiculatumcytotoxic metabolite
Verrucosidin Penicillium verrucosumcytotoxic pyrone-type polyketide
Verrulactone A Penicilliumantimicrobial alternariol
Versicolamide B marine Aspergillusa paraherquamide-stephacidin
Viscumamide mangrove-derived endophytic fungi cyclic peptide
Yaequinolone J1 Penicillium sp. FKI-2140antibiotic

See also

Related Research Articles

<span class="mw-page-title-main">Mold</span> Wooly, dust-like fungal structure or substance

A mold or mould is one of the structures that certain fungi can form. The dust-like, colored appearance of molds is due to the formation of spores containing fungal secondary metabolites. The spores are the dispersal units of the fungi. Not all fungi form molds. Some fungi form mushrooms; others grow as single cells and are called microfungi.

<i>Penicillium</i> Genus of fungi

Penicillium is a genus of ascomycetous fungi that is part of the mycobiome of many species and is of major importance in the natural environment, in food spoilage, and in food and drug production.

<i>Aspergillus</i> Genus of fungi

Aspergillus is a genus consisting of several hundred mould species found in various climates worldwide.

<i>Penicillium roqueforti</i> Species of fungus

Penicillium roqueforti is a common saprotrophic fungus in the genus Penicillium. Widespread in nature, it can be isolated from soil, decaying organic matter, and plants.

<span class="mw-page-title-main">Gliotoxin</span> Chemical compound

Gliotoxin is a sulfur-containing mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by several species of fungi, especially those of marine origin. It is the most prominent member of the epipolythiopiperazines, a large class of natural products featuring a diketopiperazine with di- or polysulfide linkage. These highly bioactive compounds have been the subject of numerous studies aimed at new therapeutics. Gliotoxin was originally isolated from Gliocladium fimbriatum, and was named accordingly. It is an epipolythiodioxopiperazine metabolite that is one of the most abundantly produced metabolites in human invasive Aspergillosis (IA).

Aspergillus ochraceus is a mold species in the genus Aspergillus known to produce the toxin ochratoxin A, one of the most abundant food-contaminating mycotoxins, and citrinin. It also produces the dihydroisocoumarin mellein. It is a filamentous fungus in nature and has characteristic biseriate conidiophores. Traditionally a soil fungus, has now began to adapt to varied ecological niches, like agricultural commodities, farmed animal and marine species. In humans and animals the consumption of this fungus produces chronic neurotoxic, immunosuppressive, genotoxic, carcinogenic and teratogenic effects. Its airborne spores are one of the potential causes of asthma in children and lung diseases in humans. The pig and chicken populations in the farms are the most affected by this fungus and its mycotoxins. Certain fungicides like mancozeb, copper oxychloride, and sulfur have inhibitory effects on the growth of this fungus and its mycotoxin producing capacities.

<span class="mw-page-title-main">Cerevisterol</span> Chemical compound

Cerevisterol (5α-ergosta-7,22-diene-3β,5,6β-triol) is a sterol. Originally described in the 1930s from the yeast Saccharomyces cerevisiae, it has since been found in several other fungi and, recently, in deep water coral. Cerevisterol has some in vitro bioactive properties, including cytotoxicity to some mammalian cell lines.

Throughout human history, fungi have been utilized as a source of food and harnessed to ferment and preserve foods and beverages. In the 20th century, humans have learned to harness fungi to protect human health, while industry has utilized fungi for large scale production of enzymes, acids, and biosurfactants. With the advent of modern nanotechnology in the 1980s, fungi have remained important by providing a greener alternative to chemically synthesized nanoparticle.

<span class="mw-page-title-main">Chaetoglobosin A</span> Chemical compound

Chaetoglobosin A is a fungal isolate with anticancer activity in vitro. Derivatives of the compound include MBJ-0038, MBJ-0039, and MBJ-0040.

<span class="mw-page-title-main">Vermistatin</span> Chemical compound

Vermistatin is an organic compound and a metabolite of mine-dwelling Penicillium vermiculatum found in Berkeley Pit Lake, Butte, Montana. Penisimplicissin is a vermistatin analog with anticancer activity.

<span class="mw-page-title-main">Shearinine</span>

Shearinines A,D,E,and F, are marine fungal isolates with anticancer activity in vitro. They were isolated from a stain of Penicillium janthinellum Biourge. Their potential anticancer activity has been suggested by their induction of apoptosis in HL-60 cells. Shearinines D, E and G have also been found to block activity on large-conductance calcium-activated potassium channels.

<span class="mw-page-title-main">Meleagrin</span> Chemical compound

Meleagrin and its derivatives such as oxaline are bio-active benzylisoquinoline alkaloids made by various species of Penicillium fungi. It is similar to other fungal alkaloids, such as Roquefortine C, which is made as an intermediate in the same biosynthetic pathway.

<span class="mw-page-title-main">14-Norpseurotin A</span> Chemical compound

14-Norpseurotin A is an alkaloid and a bio-active metabolite of Aspergillus, featuring an oxa-spiro-lactam core.

Aspergillus penicillioides is a species of fungus in the genus Aspergillus, and is among the most xerophilic fungi.

<span class="mw-page-title-main">Dideoxyverticillin A</span> Chemical compound

Dideoxyverticillin A, also known as (+)-11,11′-dideoxyverticillin A, is a complex epipolythiodioxopiperazine initially isolated from the marine fungus Penicillium sp. in 1999. It has also been found in the marine fungus Bionectriaceae, and belongs to a class of naturally occurring 2,5-diketopiperazines.

Streptomyces isolates have yielded the majority of human, animal, and agricultural antibiotics, as well as a number of fundamental chemotherapy medicines. Streptomyces is the largest antibiotic-producing genus of Actinomycetota, producing chemotherapy, antibacterial, antifungal, antiparasitic drugs, and immunosuppressants. Streptomyces isolates are typically initiated with the aerial hyphal formation from the mycelium.

<span class="mw-page-title-main">9-Deacetoxyfumigaclavine C</span> Chemical compound

9-Deacetoxyfumigaclavine C is an ergoline alkaloid. It is a potent, selective, anticancer compound, with in vitro activity comparable to doxorubicin (IC50 = 3.1 μM against K562). 9-Deacetoxyfumigaclavine C is a compound made by a variety of fungi.

Medicinal fungi are fungi that contain metabolites or can be induced to produce metabolites through biotechnology to develop prescription drugs. Compounds successfully developed into drugs or under research include antibiotics, anti-cancer drugs, cholesterol and ergosterol synthesis inhibitors, psychotropic drugs, immunosuppressants and fungicides.

<span class="mw-page-title-main">Human interactions with fungi</span> Overview of human—fungi interactions

Human interactions with fungi include both beneficial uses, whether practical or symbolic, and harmful interactions such as when fungi damage crops, timber, food, or are pathogenic to animals.

<span class="mw-page-title-main">Phomoxanthone</span> Class of chemical compounds

The phomoxanthones are a loosely defined class of natural products. The two founding members of this class are phomoxanthone A and phomoxanthone B. Other compounds were later also classified as phomoxanthones, although a unifying nomenclature has not yet been established. The structure of all phomoxanthones is derived from a dimer of two covalently linked tetrahydroxanthones, and they differ mainly in the position of this link as well as in the acetylation status of their hydroxy groups. The phomoxanthones are structurally closely related to other tetrahydroxanthone dimers such as the secalonic acids and the eumitrins. While most phomoxanthones were discovered in fungi of the genus Phomopsis, most notably in the species Phomopsis longicolla, some have also been found in Penicillium sp.

References

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  2. ↑ Hawas UW, El-Beih AA, El-Halawany AM (2012). "Bioactive anthraquinones from endophytic fungus Aspergillus versicolor isolated from red sea algae". Arch Pharm Res. 35 (10): 1749–56. doi:10.1007/s12272-012-1006-x. PMID   23139125. S2CID   25106490.
  3. ↑ Shao CL, Wang CY, Wei MY, Gu YC, She ZG, Qian PY, et al. (2011). "Aspergilones A and B, two benzylazaphilones with an unprecedented carbon skeleton from the gorgonian-derived fungus Aspergillus sp". Bioorg Med Chem Lett. 21 (2): 690–3. doi:10.1016/j.bmcl.2010.12.005. PMID   21194945.
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  5. ↑ Giese, Ellen C.; Gascon, Jacob; Anzelmo, Gianluca; Barbosa, Aneli M.; da Cunha, Mário A. Alves; Dekker, Robert F.H. (January 2015). "Free-radical scavenging properties and antioxidant activities of botryosphaeran and some other β-D-glucans". International Journal of Biological Macromolecules. 72: 125–130. doi:10.1016/j.ijbiomac.2014.07.046. ISSN   0141-8130. PMID   25128096.
  6. ↑ Kawahara, T; Itoh, M; Izumikawa, M; Sakata, N; Tsuchida, T; Shin-Ya, K (2013). "New chaetoglobosin derivatives, MBJ-0038, MBJ-0039 and MBJ-0040, isolated from the fungus Chaetomium sp. f24230". The Journal of Antibiotics. 66 (12): 727–30. doi:10.1038/ja.2013.75. PMID   23881215. S2CID   2926936.
  7. ↑ Matsuura, Masanori; Saikawa, Yoko; Inui, Kosei; Nakae, Koichi; Igarashi, Masayuki; Hashimoto, Kimiko; Nakata, Masaya (2009). "Identification of the toxic trigger in mushroom poisoning". Nature Chemical Biology. 5 (7): 465–7. doi:10.1038/nchembio.179. PMID   19465932.
  8. ↑ Kuhr, I; Fuska, J; Sedmera, P; Podojil, M; Vokoun, J; Vanĕk, Z (1973). "An antitumor antibiotic produced by Penicillium stipitatum Thom; its identity with duclauxin". The Journal of Antibiotics. 26 (9): 535–6. doi: 10.7164/antibiotics.26.535 . PMID   4799788.
  9. ↑ Mizushina Y, Kuramochi K, Ikawa H, Kuriyama I, Shimazaki N, Takemura M, et al. (2005). "Structural analysis of epolactaene derivatives as DNA polymerase inhibitors and anti-inflammatory compounds". Int J Mol Med. 15 (5): 785–93. doi:10.3892/ijmm.15.5.785. PMID   15806299.
  10. ↑ Halecker S, Surup F, Kuhnert E, Mohr KI, Brock NL, Dickschat JS, et al. (2014). "Hymenosetin, a 3-decalinoyltetramic acid antibiotic from cultures of the ash dieback pathogen, Hymenoscyphus pseudoalbidus". Phytochemistry. 100: 86–91. Bibcode:2014PChem.100...86H. doi:10.1016/j.phytochem.2014.01.018. hdl: 10033/337879 . PMID   24529574.
  11. ↑ Herath, K.; Jayasuriya, H.; Bills, G.; Polishook, J.; Dombrowski, A.; Guan, Z.; Felock, P.; Hazuda, D.; Singh, S. Isolation, Structure, Absolute Stereochemistry and HIV-1 Inhibitory Activity of Integrasone, a Novel Fungal Polyketide. J. Nat. Prod. 2004, 67, 872-874.
  12. ↑ Du, L; Robles, AJ; King, JB; Powell, DR; Miller, AN; Mooberry, SL; Cichewicz, RH (2013). "Crowdsourcing Natural Products Discovery to Access Uncharted Dimensions of Fungal Metabolite Diversity". Angewandte Chemie International Edition in English. 53 (3): 804–9. doi:10.1002/anie.201306549. PMC   4028707 . PMID   24285637.
  13. ↑ Toledo TR, Dejani NN, Monnazzi LG, Kossuga MH, Berlinck RG, Sette LD, et al. (2014). "Potent Anti-Inflammatory Activity of Pyrenocine A Isolated from the Marine-Derived Fungus Penicillium paxilli Ma(G)K". Mediators Inflamm. 2014: 767061. doi: 10.1155/2014/767061 . PMC   3916108 . PMID   24574582.
  14. ↑ Chen L, Fang Y, Zhu T, Gu Q, Zhu W (2008). "Gentisyl alcohol derivatives from the marine-derived fungus Penicillium terrestre". J Nat Prod. 71 (1): 66–70. doi:10.1021/np070421v. PMID   18163588.
  15. ↑ Stierle AA, Stierle DB, Girtsman T (2012). "Caspase-1 inhibitors from an extremophilic fungus that target specific leukemia cell lines". J Nat Prod. 75 (3): 344–50. doi:10.1021/np200414c. PMC   3330824 . PMID   22295871.
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