. 2021 May 6;46:163–187. doi: 10.3767/persoonia.2021.46.06

Table 4.

Reported extrolites produced by members of Penicillium section Canescentia.

Strain	Original identity	Identification method, ITS	Correct identity	Series	Extrolites
CBS 141311	P. arizonense	MH492021, culture ex-type of P. arizonense	P. arizonense	Canescentia	Austalide B, J, K, L, curvulinic acid, dechlorogriseofulvin, 6-farnesyl-5,7-di-hydroxy-4-methylphthalide, fumagillin, griseofulvin, pseurotin A, pyripyropene A, E, F, O, tryptoquivaline C (or 27-epi-tryptoquivaline), tryptoquivaline G (or L), xanthoepocin^1,²
CGMCC 3.9958	P. canescens	Reported to be 100% identical to ex-type of P. canescens	P. canescens	Canescentia	Penicanone, penicanescone A-C, integrastatin B³
CGMCC 3.9958	P. canescens	Reported to be 100% identical to ex-type of P. canescens	P. canescens	Canescentia	Canescone A-E⁴ (Canescone A-C, two stereoisomers each)
PL9A	P. canescens	Comparison to culture ex-type of P. canescens	P. canescens	Canescentia	Curvulic acid, dechlorogriseofulvin, griseofulvin, Sch 642305⁵
ATCC 10419	P. canescens	Culture ex-type	P. canescens	Canescentia	Griseofulvin⁶, Decaturin A, C, D, F, G, 15-deoxyoxalicine A & B, predecaturin E⁷
4.1.4.6a	P. canescens	MH820167	P. arizonense, P. canescens, P. janczewskii, P. jensenii, P. murcianum, or P. radiatolobatum (all in series Canescentia). Presence of the bromphilone chromophore in the culture ex-type of P. canescens indicates that the fungus is indeed P. canescens	Canescentia	Bromophilone A & B, citreohybridinol, curvulinic acid, dechlorogriseofulvin, griseofulvin, griseophenone B, C, G, griseoxanthone C, methyl 3-chloro-2-(2,4-dimethoxy-6-methylphenoxy)-6-hydroxy-4-methoxybenzoate, methylcurvulinate, 3-O-methyl curvulinate, norlichexanthone, penicillic acid, piscarinine B, vulculic acid⁸
VKM F-1148, VKM F-1287, VKM F-3108	Unknown identity	Morphology	P. canescens	Canescentia	Fellutanine A, isorugulosuvine A & B⁹
Sp. 4829	Penicillium species	MH465534	P. rubens but extrolite data suggest P. canescens	Canescentia	Citreohybriddione C, citreohybridinol, curvulinic acid, 2,4-dihydroxy-6-(oxopropyl) benzoic acid, (S)-2-(2-hydroxypropanamido) benzamide, griseofulvin, N-(2-hydroxypropanoyl)-2-amino benzoic acid, niacinamide, methyl 2-acetyl-3,5-dihydroxyphenylacetate, 6-O-methylnorlichexanthone, penicamide A & B, peni-isochroman A & B, 2-pyruvamidobenzamide, 2-pyruvoylaminobenzamide, pseurotin A, 3,6,8-trihydroxy-1-methylxanthone¹⁰,¹¹
MMS 194, MMS 460	P. canescens	Morphology	P. cf. canescens	Canescentia	Dechlorogriseofulvin, griseofulvin, maculosin, oxaline, orselllinic acid, penicillic acid, penitremone A-C (tentative id.)¹²
ILF-002	P. canescens	FASTA files for ITS and β-tubulin sequences show that this strain is not P. canescens s.str., but a new species	New species sister to Penicillium canescens	Canescentia	Dechlorogriseofulvin, 6-desmethyldechlorogriseofulvin,6-desmethylgriseofulvin, 1,6-dihydroxy-3-methoxy-8-methylxanthone, griseofulvin, orsellinic acid, penicillic acid, pseurotin A, 1,2,3,5,6-pentahydroxy-8-methylxanthone, 1,3,5,6-tetra-hydroxy-8-methylxanthone, vulculic acid¹³
170A/28	P. canescens	Morphology	Probably P. nigricans	Canescentia	Penitrem A^14,¹⁵
CBS 288.53	P. canescens	Morphology	New species of Penicillium	Canescentia	Canescin¹⁶
BAFC 3291	P. canescens	Morphology	Probably P. aurantiogriseum	Canescentia	Aurantiamine, cyclo(L-Phe-L-Hyp), cyclo(L-Phe-L-Pro), cyclo(D-Phe-L-Val-D-Val-L-Tyr), pseurotin A¹⁷
No number	P. canescens	No data	Unknown	Canescentia	Adamantanecarboxanilide, aphthosin, 9,10-anthracenedione, borane, decane, diethylphthalate, di-p-tolylacetylene, dodecane, eicosane, heptadecane, hexa-decane, hexadecanoic acid, 1,3,8-p-menthatriene, nicodicodine, orcinol, oxalic acid, phenanthrene, tetradecane, thioxanthene, tridecane, p-xylene¹⁸ (mostly volatiles)
No number	P. canescens	Morphology	Unknown	Canescentia	Citrinin¹⁹,²⁰
No number	P. canescens (two strains)	Morphology	P. cyclopium or P. canescens	Canescentia	Penicillic acid²¹,²²
ZJQY610	P. canescens	GU556971	P. canescens or other series Canescentia species	Canescentia	O-acetylbenzeneamidino-carboxylic acid, griseofulvin, 4-hydroxy-5-methoxy-2-methyl-naphtho[1,2-b]furan-3-carboxylic acid²³
No number	P. canescens	Morphology	Unknown	Canescentia	Citrinin, patulin, penicillic acid²⁴
SCSIOz053	P. canescens	JN585930	Talaromyces fusiformis?	Canescentia	Canescenin A & B²⁵
No number	P. canescens	Morphology	Talaromyces sp.?	Canescentia	Rugulosin²⁶
No number	P. canescens	Morphology	Probably P. verrucosum	Canescentia	Ochratoxin A²⁷
NRRL 2301	P. janczewskii	Morphology	P. janczewskii	Canescentia	Bromogriseofulvin, dechlorogriofulvin, griseofulvin^28,^29,³⁰, fungistatic and bacteriostatic red pigment³¹
CBS 141000	P. corvianum	KT887875, culture ex-type	P. corvianum	Canescentia	Compactin (= mevastatin), fiscalin C, trichodermamide C, C₁₁H₁₅O₃N, C₁₈H₂₂O₅, C₂₉H₃₀O₇S₂³²
VKMF-312	P. janczewskii	Morphology	P. janczewskii	Canescentia	Dechlorogriseofulvin, griseofulvin, patulin³³
VKMF-2191, VKMF-2378, VKMF-3023	P. janczewskii	Morphology	P. janczewskii	Canescentia	Dechlorogriseofulvin, griseofulvin³³
VKMF-685	P. janczewskii	Morphology	P. janczewskii or P. nigricans	Canescentia	Aurantioclavine, 6-N-ethylaurantioclavine³³
VKMF-2377	P. janczewskii	Morphology	P. janczewskii?	Canescentia	Epicostaclavine³³
VKMF-2489	P. janczewskii	Morphology	P. janczewskii?	Canescentia	16-N-ethylroquefortine D, glandicolin B, (E)-3-(1H-imidazol-4-yl-methylene)-6-(1H-indol-3-yl methyl)-2,5-piperazinediol, meleagrin, roquefortine C³³
DSM 17433 = KMPB H-TW5/869	P. janczewskii	Morphology	P. janczewskii?	Canescentia	3R^,4R^- and 3S^,4R^-Dihydroxy-4-(4’-methoxyphenyl)-3,4-dihydro-2(1H)-quinolinone, 3-methoxy-4-hydroxy-4-(4’-methoxyphenyl)-3,4-dihydro-2(1H)-quinolinone, peniprequinolone³⁴
F 2757 & F 2641	P. janczewskii	Morphology	P. janczewskii?	Canescentia	Fumagillin methyl ester, cis-fumagillin methyl ester^35,³⁶
No number	P. janczewskii	Morphology	P. janczewskii?	Canescentia	Cycloaspeptide A, gliovictin, gliovictin acetate, peniprequinolone, pseurotin A^37,³⁸
IFO 7745 = CBS 744.70 = ATCC 18380	P. nigricans var. sulphuratum	Morphology	P. janczewskii	Canescentia	Griseofulvin³⁹
IMI 228669 and no number17	P. janczewskii	Morphology	P. janczewskii	Canescentia	19-Deoxypaxillin-16β-ol, nigrifortine (= amauromine), paxilline, penitrem A, penitrem E, pennigritrem^15,^40,^41,^42,⁴³
SIIA-F3933	P. janczewskii	Morphology	Probably P. corvianum	Canescentia	Compactin (= mevastatin)⁴⁴
NRRL 909	P. jensenii	AY443470, culture ex-type	P. jensenii	Canescentia	Griseofulvin⁶
VKMF-292, VKMF-293	P. jensenii	Morphology	P. jensenii	Canescentia	Meleagrin, roquefortine C & D⁹
F-2813	P. jensenii	Morphology	P. jensenii	Canescentia	Fumagillin, fumagillol⁴⁵
No number	P. nigricans	Morphology	P. nigricans	Canescentia	Griseofulvin^46,⁴⁷
No number & LSHTM P38 = BRL 250	P. nigricans	Morphology	P. nigricans	Canescentia	Griseofulvin^48,⁴⁹
No number	P. nigricans	Morphology	P. nigricans?	Canescentia	MT81⁵⁰
F-5261	P. nigricans	Morphology	P. nigricans	Canescentia	Fumagillin, fumagillol⁴⁵
IMI 228669	P. nigricans	Morphology	P. janczewskii	Canescentia	19-Deoxypaxillin-16β-ol, nigrifortine (= amauromine), paxilline, penitrem A, penitrem C, penitrem E, PC-M6, pennigritrem^40,^41,^45,⁵¹
LSHTM P38	P. nigricans	Morphology	P. nigricans	Canescentia	Cyclo(L-Phe-L-Phe)⁵²
170/D2 & 170/D4	P. nigricans	Morphology	P. nigricans? or P. brasilianum	Canescentia	Verruculogen (as toxin X)^53,⁵⁴
No number	P. nigricans	Morphology	P. nigricans?	Canescentia	Albidin⁴⁸
CBS 410.69	P. yarmokense	Ex type, KC411757	P. yarmokense	Canescentia	Griseofulvin⁶
MMS 351 = LCP 99.43.43, MMS 747	section Canes-centia species	JN676192 (and β-tubulin: JN794530)	P. yarmokense (first identified as P. waksmanii)⁵⁶	Canescentia	Agroclavine, dechlorogriseofulvin, festuclavine, griseofulvin, penicillic acid, ligerin, nortryptoquivaline, orcinol, orsellinic acid^12,⁵⁵
FH-14	P. antarcticum	Morphology, identified by Westerdijk Fungal Biodiversity Institute (WFBI)	P. antarcticum	Atroveneta	Antarone A & B⁵⁶
MMS 14, MMS 15	P. antarcticum	Morphology, ITS	P. antarcticum	Atroveneta	Antarone A, aurantioclavine, chrysogine, cladosporin (= asperentin), 5-hydroxy-asperentin, patulin, terrestric acid?, violaceic acid^12,⁵⁷
AF3-117C	Penicillium species	JX967116	P. antarcticum	Atroveneta	Cladosporin (= asperentin), epiepoformin, patulin, phyllostin⁵⁸
YK-247	P. coralligerum	LC2145672	P. antarcticum	Atroveneta	5′-hydroxyasperentin, cladomarine, cladosporine (= asperentin)⁵⁹
No number	P. antarcticum	Polyphasic identification, no data	P. antarcticum	Atroveneta	cis-Cyclo(4R-Hyp, L- Leu), trans-cyclo(4R-Hyp, L-Leu), cis-cyclo(4R-Hyp, L-Phe), cyclo-(L-Pro, Gly), ethyl 8-hydroxyhexylitaconate, ethyl-9-hydroxyitaconate, (-)-hydroxyhexylitaconate, cis-4-hydroxymellein, methyl-8-hydroxyhexylitaconate, methyl-9-hydroxyitaconate, methylitaconate, 2-phenetylalcohol⁶⁰
KMM 4668	P. piltunense	Culture ex-type (but synonym of P. antarcticum)	P. antarcticum	Atroveneta	Penigrisacid D, piltunine A-F⁶¹
No number	Marine-derived P. atrovenetum	Morphology	Probably P. antarcticum, as P. atrovenetum is a soil fungus	Atroveneta	Citreohybridinol⁶²
9 strains, no numbers	P. antarcticum	No data	P. antarcticum (?)	Atroveneta	Butylphthalate, dibutylphthalate, di-2-ethylhexylphthalate, hydrocarbons, squalene, and fatty acids (the latter are general metabolites)⁶³
Strain 68 & 56	P. atrovenetum & P. coralligerum	MH881491, MH881479	P. antarcticum	Atroveneta	Aspinonene, atrovenetin, atrovenetinone, brevicompanine E, citreohydridonol, deoxyherquenone, griseofulvin, marcfortine C^*, penitrem B, phytosphingosine⁶⁴
Strains 4-7 & 9-13	P. atrovenetum & P. antarcticum	ITS and morphology	P. antarcticum (P. atrovenetum is regarded as a soil-borne species)	Atroveneta	2-Acetyl-4(3H)-quinazolinone, aflatoxin M1^, andrastin A, andrastin “X” (wrongly identified as (wia) antibiotic UK 88051-9), antarone B (wia purpactin A), anti-biotic SMTP8^, arisugacin B^, asperentin (wia (S)-curvularin), atrovenetin, atro-venetinone (wia tetrahydrohalenaquinone A), bionectin B^, (S)-chrysogine, chaetoglobosin 510^, cladosporin-8-methylether (wia antibiotic PO1), cytosporone A^, cytosporone E^, deacetoxyfructigenine A (wia tubingensin A or B), deoxy-herquenone (= UP31), dictyosphaeric acid^, hamigeromycin^, hamigerone (wia austalide K), hongoquercin A^, (S)- 5-hydroxyasperentin (wia 11α-hydroxycurvularin), a hydroxyasperentin (wia 7,8-dihydro-7α-hydroxyresorcylide), 4-hydroxy-1-methoxy-5-phenyl-3-(tetrahydro-6-(3-hydroxy-1-methylpropyl)-3,5-dimethyl-2H-pyran-2-yl)-2(1H)-pyridinone^, libertellone B^, 3-O-methylterprenin^, patulin, penitrem A, penitrem E, podosporin A^, sporidesmin D^, stachybosin^, talaro-convolutin B^, territrem C^, 2’,2’’,3’,3’’-tetrahydrobisvertinolone^, tropolactone C^, UP10, 11, 12, 15, 9, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 32^** ⁶⁵
IMI 061837 = CBS 241.56	P. atrovenetum	AF033492, culture ex-type, morphology	P. atrovenetum	Atroveneta	3-nitropropionic acid⁶⁶, atrovenetin⁶⁷
HO9-2	P. atrovenetum	EMBL no. KC009765	P. atrovenetum?	Atroveneta	Cyclopiazonic acid⁶⁸
CECT 2886	P. novae-zeelandiae	Morphology	P. novae-zeelandiae	Atroveneta	Gentisylalcohol, 3-hydroxybenzylalcohol, patulin (in 1949 reported as expansine)^6,^32,^69,⁷⁰
IBT 21392 (= IMI 204086), IBT 22457	P. novae-zeelandiae	Morphology	P. novae-zeelandiae	Atroveneta	Atlantinone A⁷¹
No number	P. novae-zeelandiae	Morphology	P. novae-zeelandiae?	Atroveneta	Penitrem A, verruculogen¹⁵
No number	P. novae-zeelandiae	Morphology	P. novae-zeelandiae?	Atroveneta	Curvulinic acid⁷²
CBS 140987	P. nucicola	KT887860, culture ex-type	P. nucicola	Atroveneta	Andrastin A-D, austin, C₂₀H₂₀O₆³²

* The metabolites tentatively identified may also be other secondary metabolites with the same molecular mass. For example if aflatoxin M1 in P. antarcticum would have been correctly identified, one would also expect presence of aflatoxin B1 and B2, which are usually the main biosynthetic products in the aflatoxin secondary metabolite biosynthetic family.

** UP: Unknown secondary metabolites with a known molecular mass.

*** Penicillium linzhiense was recently described and thus not examined during this study.

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