Fungal isolate

{{short description|Compound isolated from fungi for medicinal benefit}}

{{more footnotes needed|date=April 2021}}

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.

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==

file: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.

class="wikitable" style="width: 80%; float: center; font-size: 90%; margin-left: 25px;"
scope="col" style="width: 70px;" | Isolate

! scope="col" width="100px" | Source

! scope="col" width="160px" | Researched activity / Chemical description

9-Deacetoxyfumigaclavine C

| endophytic Aspergillus fumigatus

| style="text-align: center;" | potent, selective, anticancer activity comparable to doxorubicin (IC50 = 3.1 μM against K562){{cite journal|vauthors=Ge HM, Yu ZG, Zhang J, Wu JH, Tan RX | title=Bioactive alkaloids from endophytic Aspergillus fumigatus. | journal=J Nat Prod | year= 2009 | volume= 72 | issue= 4 | pages= 753–5 | doi=10.1021/np800700e | pmid=19256529 }}

14-Norpseurotin A

| Aspergillus

| style="text-align: center;" |antiparasitic/anticancer

3-O-Methylfunicone

| Penicillium pinophilum

| style="text-align: center;" | in vitro cancer stem cell inhibitor

Anicequol

| Penicillium aurantiogriseum

| style="text-align: center;" | in vitro anchorage-independent cancer inhibitor

Anomalin A

| sponge-derived Arthrinium

| style="text-align: center;" | angiogenesis inhibitor

Antiamoebin

| Emericellopsis

| style="text-align: center;" | anti-microbial/protozoan polypeptide

Arugosin C

| Aspergillus versicolor isolated from Red Sea green alga

| style="text-align: center;" | bio-active anthraquinone{{cite journal|vauthors=Hawas UW, El-Beih AA, El-Halawany AM | title=Bioactive anthraquinones from endophytic fungus Aspergillus versicolor isolated from red sea algae. | journal=Arch Pharm Res | year= 2012 | volume= 35 | issue= 10 | pages= 1749–56 | doi=10.1007/s12272-012-1006-x | pmid=23139125 | s2cid=25106490 }}

Aspergillides A-C

| marine Aspergillus ostianus

| style="text-align: center;" | anticancer/cytotoxic

Aspergillusene

| "sea fan"-derived Aspergillus sydowii

| style="text-align: center;" | antioxidant sesquiterpene

Aspergilone A

| "sea fan"-derived Aspergillus

| style="text-align: center;" | anticancer and antifouling activity{{cite journal |vauthors=Shao CL, Wang CY, Wei MY, Gu YC, She ZG, Qian PY, etal | title=Aspergilones A and B, two benzylazaphilones with an unprecedented carbon skeleton from the gorgonian-derived fungus Aspergillus sp. | journal=Bioorg Med Chem Lett | year= 2011 | volume= 21 | issue= 2 | pages= 690–3 | doi=10.1016/j.bmcl.2010.12.005 | pmid=21194945 }}

Aspergillusol A

| marine Aspergillus

| style="text-align: center;" | alpha-glucosidase inhibitor

Asperterrestide A

| marine Aspergillus terreus

| style="text-align: center;" | cytotoxic and antiviral cyclic tetrapeptide

Asterric acid

| Antarctic Geomyces

| style="text-align: center;" | endothelin binding inhibitor

Auranthine

| Penicillium

| style="text-align: center;" | antimicrobial

Aurantiamine

| Penicillium aurantiogriseum

| style="text-align: center;" | valine and histidine derived diketopiperazine

Aurantiomide

| sponge-derived Penicillium aurantiogriseum

| style="text-align: center;" | quinazoline alkaloid with cytotoxic/anticancer activity

Berkeleydione

| fungal extremophile (Berkeley Pit, Montana)

| style="text-align: center;" | anticancer polyketide-terpenoid

Berkeleytrione

| fungal extremophile (Berkeley Pit, Montana)

| style="text-align: center;" | anticancer polyketide-terpenoid

Berkelic acid

| fungal extremophile (Berkeley Pit, Montana)

| style="text-align: center;" | spiroketal anticancer compound

beta-Ergocryptine

| ergot

| style="text-align: center;" | dopaminergic ergot alkaloid

Bisvertinolone

| Trichoderma

| style="text-align: center;" | anticancer{{cite journal|pmid=12120368|year=2002|last1=Abe|first1=N|last2=Arakawa|first2=T|last3=Hirota|first3=A|title=The biosynthesis of bisvertinolone: Evidence for oxosorbicillinol as a direct precursor|issue=3|pages=204–5|journal=Chemical Communications|doi=10.1039/b109505f}}

Botryodiplodin

| Penicillium

| style="text-align: center;" | antibiotic mycotoxin

Botryosphaeran

|Botryosphaeria rhodina

|free-radical scavenging and antioxidant{{Cite journal |last1=Giese |first1=Ellen C. |last2=Gascon |first2=Jacob |last3=Anzelmo |first3=Gianluca |last4=Barbosa |first4=Aneli M. |last5=da Cunha |first5=Mário A. Alves |last6=Dekker |first6=Robert F.H. |date=January 2015 |title=Free-radical scavenging properties and antioxidant activities of botryosphaeran and some other β-D-glucans |journal=International Journal of Biological Macromolecules |volume=72 |pages=125–130 |doi=10.1016/j.ijbiomac.2014.07.046 |issn=0141-8130 |pmid=25128096}}

Brevianamide S

| marine Aspergillus versicolor

| style="text-align: center;" | antimicrobial dimeric diketopiperazine

Brevicompanines D-H

| deep ocean sediment Penicillium

| style="text-align: center;" | lipopolysaccharide (LPS)-induced nitric oxide inhibitor

Cephalosporolide

| marine Penicillium

| style="text-align: center;" | novel lactones

Chaetoglobosin A

| Chaetomium

| style="text-align: center;" | anticancer{{cite journal | pmid = 23881215 | title = New chaetoglobosin derivatives, MBJ-0038, MBJ-0039 and MBJ-0040, isolated from the fungus Chaetomium sp. f24230 | year = 2013 | last1 = Kawahara | first1 = T | last2 = Itoh | first2 = M | last3 = Izumikawa | first3 = M | last4 = Sakata | first4 = N | last5 = Tsuchida | first5 = T | last6 = Shin-Ya | first6 = K | doi = 10.1038/ja.2013.75 | journal = The Journal of Antibiotics | volume=66 | issue=12 | pages=727–30| s2cid = 2926936 }}

Chaetoxanthone

| marine-derived Chaetomium

| style="text-align: center;" | bio-active xanthone

Chanoclavine

| ergot

| style="text-align: center;" | dopamine agonist

Chanoclavine II

| ergot

| style="text-align: center;" |

Chetracins B

| Antarctic psychrophilic Oidiodendron truncatum

| style="text-align: center;" | in vitro anticancer (nanomolar)

Chrysophanic acid

|

| style="text-align: center;" | antiviral/anticancer anthraquinone

Chrysosporide

|Sepedonium chrysospermum

|

Citreorosein

| Penicillium

| style="text-align: center;" | antimicrobial polyketide

Citrinolactone D

| marine-derived Penicillium

| style="text-align: center;" | citrinin derivative

Citromycetin

| Australian Penicillium

| style="text-align: center;" | bio-active polyketide

Citromycin

| Penicillium

| style="text-align: center;" | antibiotic

Communesin B

| Mediterranean Axinella-derived Penicillium

| style="text-align: center;" | anticancer

Costaclavin

| ergot

| style="text-align: center;" |

Cryptoechinuline D

| mangrove rhizosphere soil-derived Aspergillus

| style="text-align: center;" | anticancer

Curvularin

| Penicillium

| style="text-align: center;" | antimicrobial

Cycloprop-2-ene carboxylic acid

|Russula subnigricans

| style="text-align: center;" |causes rhabdomyolysis{{cite journal |last1=Matsuura |first1=Masanori |last2=Saikawa |first2=Yoko |last3=Inui |first3=Kosei |last4=Nakae |first4=Koichi |last5=Igarashi |first5=Masayuki |last6=Hashimoto |first6=Kimiko |last7=Nakata |first7=Masaya |year=2009 |title=Identification of the toxic trigger in mushroom poisoning |journal=Nature Chemical Biology |volume=5 |issue=7 |pages=465–7 |doi=10.1038/nchembio.179 |pmid=19465932}}

Decumbenone C

| marine Aspergillus sulphureus

| style="text-align: center;" | anticancer

Dehydroaltenusin

| Alternaria tenuis

| style="text-align: center;" | inhibitor of mammalian DNA polymerase α

Dehydrocurvularin

| Penicillium

| style="text-align: center;" | antimicrobial

Disydonols A-C

| marine Aspergillus

| style="text-align: center;" | anticancer

Duclauxin

| Penicillium duclauxi

| style="text-align: center;" | anticancer{{cite journal|pmid=4799788|year=1973|last1=Kuhr|first1=I|last2=Fuska|first2=J|last3=Sedmera|first3=P|last4=Podojil|first4=M|last5=Vokoun|first5=J|last6=Vanĕk|first6=Z|title=An antitumor antibiotic produced by Penicillium stipitatum Thom; its identity with duclauxin|volume=26|issue=9|pages=535–6|journal=The Journal of Antibiotics|doi=10.7164/antibiotics.26.535|doi-access=free}}

Epicoccins

| Cordyceps-colonizing Epicoccum nigrum

| style="text-align: center;" | antiviral

Epolactaene

| marine fungus

| style="text-align: center;" | antiinflammatory, inhibitory activity of DNA polymerases and DNA topoisomerase II, active synthetic analogs{{cite journal |vauthors=Mizushina Y, Kuramochi K, Ikawa H, Kuriyama I, Shimazaki N, Takemura M, etal | title=Structural analysis of epolactaene derivatives as DNA polymerase inhibitors and anti-inflammatory compounds. | journal=Int J Mol Med | year= 2005 | volume= 15 | issue= 5 | pages= 785–93 | doi= 10.3892/ijmm.15.5.785| pmid=15806299 }}

Epoxyagroclavine

| permafrost Penicillium

| style="text-align: center;" | ergot alkaloid

Epoxyphomalins A-B

| marine Paraconiothyrium

| style="text-align: center;" | potent cytotoxics

Ergosine

| ergot

| style="text-align: center;" | dopaminergic ergot alkaloid

Ergostane

| mushrooms

| style="text-align: center;" | steroid

Ergostine

| ergot

| style="text-align: center;" | alpha-adrenergic blocking, vasoconstrictive ergot alkaloid

Eupenifeldin

| Eupenicillium brefeldianum

| style="text-align: center;" | antimicrobial cytotoxic bistropolone

Evariquinone

| Emericella variecolor (derived from the marine sponge Haliclona)

| style="text-align: center;" |

Fecosterol

| fungi and lichens

| style="text-align: center;" | steroid

Fellutanine

| Penicillium

| style="text-align: center;" | bio-active diketopiperazine alkaloids

Festuclavine

| Aspergillus fumigatus

| style="text-align: center;" | bio-active ergoline

Fumigaclavine A

| endophytic Aspergillus

| style="text-align: center;" | bio-active ergoline

Fumigaclavine B

| endophytic Aspergillus

| style="text-align: center;" | bio-active ergoline

Fumigaclavine C

| endophytic Aspergillus

| style="text-align: center;" | bio-active ergoline

Fumiquinazoline

| soft coral Sinularia-derived Aspergillus fumigatus

| style="text-align: center;" | cytotoxic/anticancer

Fungisterol

| Cordyceps sinensis

| style="text-align: center;" | steroid

Glionitrin A

| mine-dwelling Aspergillus fumigatus

| style="text-align: center;" | antibiotic-anticancer

Glionitrin B

| Aspergillus fumigatus KMC-901

| style="text-align: center;" | anticancer diketopiperazine

Hymenosetin

| Hymenoscyphus pseudoalbidus

| style="text-align: center;" | antimicrobial (active against MRSA){{cite journal |vauthors=Halecker S, Surup F, Kuhnert E, Mohr KI, Brock NL, Dickschat JS, etal | title=Hymenosetin, a 3-decalinoyltetramic acid antibiotic from cultures of the ash dieback pathogen, Hymenoscyphus pseudoalbidus. | journal=Phytochemistry | year= 2014 | volume= 100 | pages= 86–91 | doi=10.1016/j.phytochem.2014.01.018 | pmid=24529574 | bibcode=2014PChem.100...86H | hdl=10033/337879 | hdl-access=free }}

Integrasone

|Unknown

|inhibits HIV-1 integrase enzymeHerath, 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.

Isoemericellin

| marine Emericella variecolor

| style="text-align: center;" |

Leporizines A-C

| Aspergillus

| style="text-align: center;" | cytotoxic epithiodiketopiperazines

Leptosphaerin

| marine Leptosphaeria oraemaris

| style="text-align: center;" | antifungal

Lichesterol

| fungi and lichens

| style="text-align: center;" | steroid

Luteoalbusins A-B

| deep sea Acrostalagmus luteoalbus

| style="text-align: center;" | anticancer indole diketopiperazines

Luteusin A

| Talaromyces luteus

| style="text-align: center;" | monoamine oxidase inhibitor

Malettinin

| Hypoxylon

| style="text-align: center;" | polyketide/antimicrobial

Maximiscin

| Tolypocladium (Salcha, Alaska){{cite journal | pmid = 24285637 | year = 2013 | last1 = Du | first1 = L | last2 = Robles | first2 = AJ | last3 = King | first3 = JB | last4 = Powell | first4 = DR | last5 = Miller | first5 = AN | last6 = Mooberry | first6 = SL | last7 = Cichewicz | first7 = RH | title = Crowdsourcing Natural Products Discovery to Access Uncharted Dimensions of Fungal Metabolite Diversity | doi = 10.1002/anie.201306549 | journal = Angewandte Chemie International Edition in English | pages = 804–9| volume=53 | issue=3 | pmc=4028707}}

| style="text-align: center;" | anticancer polyketide-shikimate compound

Meleagrin

| deep ocean Penicillium

| style="text-align: center;" | anticancer

Methylenolactocin

| Penicillium

| style="text-align: center;" | anticancer

Neoxaline

| Aspergillus japonicus

| style="text-align: center;" | antimitotic and antiplatelet

Nigerapyrones A-E

| marine mangrove-derived, endophytic Aspergillus niger

| style="text-align: center;" | anticancer

Nigrosporin B

| Nigrospora

| style="text-align: center;" | antimicrobial

Nocapyrones E-G

| Nocardiopsis dassonvillei

| style="text-align: center;" | antimicrobial alpha-pyrones

Notoamide

| marine Aspergillus

| style="text-align: center;" | bio-active prenylated indole alkaloid

Oxaline

| Penicillium oxalicum and Aspergillus japonicus

| style="text-align: center;" | anticancer (tubulin polymerization inhibitor), O-methylated derivative of meleagrin

Pencolide

| seaweed-derived endophytic fungi

| style="text-align: center;" | bio-active maleimide

Penicitrinol J

| marine-derived Penicillium

| style="text-align: center;" | bio-active citrinin dimer

Penicitrinol K

| marine-derived Penicillium

| style="text-align: center;" | bio-active citrinin derivative

Penicitrinone E

| marine-derived Penicillium

| style="text-align: center;" | bio-active citrinin dimer

Penochalasin A

| endophytic Chaetomium

| style="text-align: center;" | cytotoxic/anticancer cytochalasan-based alkaloid

Penostatin A

| Penicillium

| style="text-align: center;" | cytotoxic metabolite

Pestalamides A-C

| Pestalotiopsis theae

| style="text-align: center;" | antiviral and antifungal

Petrosifungin

| sponge-derived Penicillium brevicompactum

| style="text-align: center;" | novel cyclodepsipeptide

Phillyrin

| endophytic fungus (isolated from Forsythia)

| style="text-align: center;" | antiobesity

Piscarinine

| Penicillium piscarium westling

| style="text-align: center;" | bio-active polycyclic diketopiperazine alkaloid

Prenylterphenyllins

| marine Aspergillus candidus

| style="text-align: center;" | anticancer

Protuboxepins A and B

| Aspergillus SF-5044

| style="text-align: center;" | anticancer diketopiperazines

Pseurotin A

| endophytic Aspergillus

| style="text-align: center;" | antiparasitic and anticancer

Pyrenocine

| marine Penicillium paxilli

| style="text-align: center;" | antibiotic/antiinflammatory mycotoxin{{cite journal |vauthors=Toledo TR, Dejani NN, Monnazzi LG, Kossuga MH, Berlinck RG, Sette LD, etal | title=Potent Anti-Inflammatory Activity of Pyrenocine A Isolated from the Marine-Derived Fungus Penicillium paxilli Ma(G)K. | journal=Mediators Inflamm | year= 2014 | volume= 2014 | pages= 767061 | pmid=24574582 | doi=10.1155/2014/767061 | pmc= 3916108 | doi-access=free }}

Questiomycin A

| Penicillium expansum

| style="text-align: center;" | antibiotic

Quinocitrinine

| permafrost Penicillium

| style="text-align: center;" | quinoline alkaloid

RES-1149-2

| Aspergillus

| style="text-align: center;" | non-peptidic endothelin receptor antagonist

Retigeric acid B

| Lobaria (lichen)

| style="text-align: center;" | anticancer

Rubratoxin B

| Penicillium rubrum

| style="text-align: center;" | anticancer

Rugulovasine

| Penicillium

| style="text-align: center;" |

Sch 642305

| Penicillium verrucosum and Rhizoctonia solani

| style="text-align: center;" | bacterial DNA primase inhibitor

Sclerotides A-B

| Aspergillus sclerotiorum PT06-1

| style="text-align: center;" | bio-active cyclic hexapeptides

Secalonic acid

| marine fungi

| style="text-align: center;" | nootropic

Shamixanthone

| Aspergillus

| style="text-align: center;" | bio-active prenylated xanthone

Shearinine

| marine Penicillium janthinellum

| style="text-align: center;" | anticancer

Siderin

| Aspergillus versicolor isolated from Red Sea green alga

| style="text-align: center;" | bio-active anthraquinone

Sorbicillactone A

| sponge-derived fungus

| style="text-align: center;" | novel bio-active alkaloid

Spiculisporic acid

| marine Aspergillus

| style="text-align: center;" | bioactive γ-butenolide

Spiropreussione

| Preussia

| style="text-align: center;" | anticancer

Stephacidin

| Aspergillus ochraceus WC76466

| style="text-align: center;" | anticancer/cytotoxic

Stromemycin

| marine Emericella

| style="text-align: center;" | C-glycosidic depside matrix metalloproteinase inhibitor

Terpestacin

| endophytic fungus Drechslera ravenelii

| style="text-align: center;" | anticancer

Terrestrols

| marine Penicillium terrestre

| style="text-align: center;" | cytotoxic/anticancer{{cite journal|vauthors=Chen L, Fang Y, Zhu T, Gu Q, Zhu W | title=Gentisyl alcohol derivatives from the marine-derived fungus Penicillium terrestre. | journal=J Nat Prod | year= 2008 | volume= 71 | issue= 1 | pages= 66–70 | doi=10.1021/np070421v | pmid=18163588 }}

Terreulactone A

| Aspergillus terreus

| style="text-align: center;" | anti-acetylcholinesterase terpenoid

Topopyrone C

| Phoma and Penicillium

| style="text-align: center;" | anticancer human topoisomerase I inhibitor

Trachyspic acid

| Talaromyces trachyspermus

| style="text-align: center;" | heparanase inhibitor

Trichodimerol

| Trichoderma

| style="text-align: center;" | bio-active pentacycle

Ustusolates

| marine Aspergillus ustus

| style="text-align: center;" | anticancer

Variecolactone

| Emericella purpurea mycelium

| style="text-align: center;" | immunomodulatory sesterterpene

Variecolol

| Emericella aurantio-brunnea

| style="text-align: center;" | immunosuppressant/antiviral alkaloid

Varixanthone

| marine Emericella variecolor

| style="text-align: center;" | antimicrobial

Vermiculine

| Penicillium vermiculatum

| style="text-align: center;" | antibiotic

Vermistatin

| fungal extremophile (Berkeley Pit, Montana)

| style="text-align: center;" | anticancer{{cite journal|vauthors=Stierle AA, Stierle DB, Girtsman T | title=Caspase-1 inhibitors from an extremophilic fungus that target specific leukemia cell lines. | journal=J Nat Prod | year= 2012 | volume= 75 | issue= 3 | pages= 344–50 | pmid=22295871 | doi=10.1021/np200414c | pmc=3330824 }}

Vermixocin

| Penicillium vermiculatum

| style="text-align: center;" | cytotoxic metabolite

Verrucosidin

| Penicillium verrucosum

| style="text-align: center;" | cytotoxic pyrone-type polyketide

Verrulactone A

| Penicillium

| style="text-align: center;" | antimicrobial alternariol

Versicolamide B

| marine Aspergillus

| style="text-align: center;" | a paraherquamide-stephacidin

Viscumamide

| mangrove-derived endophytic fungi

| style="text-align: center;" | cyclic peptide

Yaequinolone J1

| Penicillium sp. FKI-2140

| style="text-align: center;" | antibiotic

See also

References

{{Reflist}}