Penicillides from Penicillium and Talaromyces: Chemical Structures, Occurrence and Bioactivities
Abstract
:1. Introduction
2. Chemical Structures
3. Occurrence
4. Biological Properties
5. Biosynthesis of Penicillide and Purpactin A
6. Related Products
7. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Code | Compounds | Chemical Structure | Nominal Mass | Formula |
---|---|---|---|---|
1 | Penicillide (= vermixocin A) | 372 | C21H24O6 | |
2 | Purpactin A (= vermixocin B) | 414 | C23H26O7 | |
3 | Δ1′,3′-1-Dehydroxypenicillide | 352 | C21H20O5 | |
4 | 1′2′-Epoxy-3′,4′-didehydropenicillide | 368 | C21H20O6 | |
5 | Dehydroisopenicillide (= MC-141, 1,2-dehydropenicillide) | 370 | C21H22O6 | |
6 | 2′-Hydroxy-3′,4′-didehydropenicillide | 386 | C21H22O7 | |
7 | 5′-Hydroxypenicillide | 388 | C21H24O7 | |
8 | Hydroxypenicillide | 404 | C21H24O8 | |
9 | Isopenicillide | 388 | C21H24O7 | |
10 | 3′-O-Methyldehydroisopenicillide (= 3-methoxy-1′2-dehydropenicillide) | 384 | C22H24O6 | |
11 | Prenpenicillide | 354 | C21H22O5 |
Species | Substrate | Location | Compounds | Ref. |
---|---|---|---|---|
Penicillium sp. | - | Japan | 1 | [5] |
Penicillium sp. | endophytic in Taxus cuspidata | Gunma (Japan) | 4, 6, 5, 10 | [14] |
Penicillium sp. F60760 | soil | South Korea | 1 | [15] |
Penicillium sp. H1 | marine | China | 1 | [16] |
Penicillium sp. MA-37 1 | rhizosphere of Bruguiera gymnorrhiza | Hainan (China) | 1, 3, 5, 10 | [17] |
Penicillium sp. PF9 | endophytic in Artemisia princeps | South Korea | 1, 10 | [18] |
Penicillium sp. SCS-KFD16 | marine | China | 1 | [19] |
Penicillium sp. ZLN29 | marine sediment | Jiazhou Bay (China) | 1, 11 | [20] |
P. chrysogenum MT-12 | endophytic in Huperzia serrata | China | 1, 2, 8, 9 | [21] |
P. montanense KYI635 2 | soil | Kanagawa (Japan) | 1, 2 | [22] |
P. simplicissimum IFM53375 | unspecified | Japan | 1, 2 | [23] |
Talaromyces sp. | moss (Climacium dendroides) | Gangneung (South Korea) | 1, 2 | [24] |
Talaromyces sp. BTBU20213036 | mud from intertidal zone | Qingdao (China) | 1 | [25] |
Talaromyces sp. CS-258 | mussel from cold seep | South China Sea | 1, 2, 5 | [26] |
Talaromyces sp. HK1-18 | mangrove soil | Hainan (China) | 1 | [27] |
Talaromyces sp. IQ-567 | endophytic in Rhizophora mangle | Tecomate Lagoon (Mexico) | 1 | [28] |
Talaromyces sp. LF458 | sponge (Axinella verrucosa) | Elba island (Italy) | 3, 10 | [29] |
Talaromyces sp. M27416 | sea water | Dongshan island (China) | 1 | [30] |
Talaromyces sp. Wangcy005 | gorgonian (Subergorgia suberosa) | Weizhou island (China) | 1, 2, 3 | [31] |
Talaromyces sp. WHUF0362 | mangrove soil | Hainan (China) | 2 | [32] |
T. aculeatus IBT23209 | soil | Araracuara (Colombia) | 1, 2 | [33] |
T. aculeatus IBT23210 | 2 | |||
T. aculeatus IBT23211 | 2 | |||
T. aculeatus IBT23212 | 2 | |||
T. aculeatus PSU-RSPG105 | soil | Rajjaprabha Dam (Thailand) | 1, 2 | [34] |
T. albobiverticillius IBT4466 | imported pomegranate | Denmark | 2 | [35] |
T. albobiverticillius CBS113167 | air in cake factory | - | 2 | |
T. amestolkiae CBS433.62 | ground domestic waste | Verona (Italy) | 2 | [36] |
T. amestolkiae CBS436.62 | alum solution | - | 2 | |
T. atroroseus IBT3933 | - | - | 2 | [35] |
T. atroroseus TRP-NRC | agricultural waste | Egypt | 2 | [37] |
T. derxii NHL2981 | soil | Kurashiki (Japan) | 1, 5 | [38] |
T. flavus CCMF-276 | soil | Jàchymov (Czechia) | 1, 2 | [39] |
T. flavus ATCC74110 | - | - | 1 | [40] |
T. flavus TGGP34 | endophytic in Acanthus ilicifolius | China | 1, 2, 5 | [41] |
T. fuscoviridis CBS193.69 | soil | the Netherlands | 2 | [42] |
T. gwangjuensis CNUFC-WT19-1 | freshwater | Yeosu (South Korea) | 2 | [43] |
T. koreana CNUFC-YJW2-13 | freshwater | Yeosu (South Korea) | 2 | |
T. pinophilus AF-02 | endophytic in Allium fistulosum | Lanzhou (China) | 1 | [44] |
T. pinophilus FKI-5653 | soil | Hachijo island (Japan) | 1, 5 | [45] |
T. pinophilus H608 | mangrove sediment | Xiamen (China) | 1, 2, 3, 5, 7, 9 | [46] |
T. pinophilus LT6 | tobacco rhizosphere | Lecce area (Italy) | 1 | [47] |
T. pinophilus SCAU037 | rhizosphere of Rhizophora stylosa | Techeng isle (China) | 1, 9, 10 | [48] |
T. pinophilus XS-20090E18 | unidentified gorgonian | Xisha islands (China) | 1, 2, 8, 9 | [49] |
T. purgamentorum CBS113145 | forest leaf litter | Peña Roja (Colombia) | 1, 2 | [33] |
T. purpureogenus CFRM02 | unspecified | Karnataka (India) | 1 | [50] |
T. purpureogenus FO-608 | soil | Japan | 2 | [6] |
T. purpureogenus ATCC44445 | corn kernel | Georgia (USA) | 2 | [36] |
T. purpureogenus ATCC20204 | - | Japan | 2 | |
T. purpureogenus CBS286.36 | - | Japan | 2 | |
T. purpureogenus IBT17540 | barley | Winnipeg (Canada) | 2 | |
T. purpureogenus IBT11632 | imported marjoram | Denmark | 2 | |
T. purpureogenus IBT12779 | marine | France | 2 | |
T. purpureogenus IMI112715 | rhizosphere of Trifolium alexandrinum | Egypt | 2 | |
T. purpureogenus IMI136126 | molded corn | Wisconsin (USA) | 2 | |
T. purpureogenus IMI136127 | molded corn | Wisconsin (USA) | 2 | |
T. purpureogenus NRRL3290 | - | Georgia (USA) | 2 | |
T. purpureogenus MM | cotton textile | Egypt | 1, 10 | [51] |
T. ruber CBS237.93 | unknown | Unknown | 2 | [36] |
T. ruber CBS113160 | - | - | 2 | |
T. ruber CBS132699 | sandy soil | Sousse (Tunisia) | 2 | |
T. ruber FRR1503 | preserved wood | Australia | 2 | |
T. ruber IBT31167 | - | - | 2 | |
T. stellenboschiensis CBS135665 | soil | Stellenbosch (South Africa) | 2 | [42] |
T. stipitatus SK-4 | leaf of Acanthus ilicifolius | Guangxi (China) | 1, 2 | [52] |
T. thailandensis PSU-SPSF059 | soil | Thailand | 2 | [53] |
T. veerkampii CBS500.78 | soil | Meta (Colombia) | 1, 2 | [42] |
T. veerkampii CBS136668 | soybean seed | Matou (Taiwan) | 1, 2 | [42] |
T. verruculosus TGM14 | mangrove (Xylocarpus granatum) | Hainan (China) | 1 | [54] |
Biological Activity | Concentration | Results and Further Details | Ref. |
---|---|---|---|
Penicillide (1) | |||
Antibacterial | 100 µg mL−1 | Acinetobacter baumannii (40% inhibition) | [28] |
50 µg mL−1 | Clostridium perfringens (MIC) | [44] | |
64 µg mL−1 | Escherichia coli (MIC) | [26] | |
64 µg mL−1 | Klebsiella pneumoniae (MIC) | [26] | |
50 µg mL−1 | Micrococcus tetragenus (MIC) | [44] | |
32 µg mL−1 | Pseudomonas aeruginosa (MIC) | [26] | |
100 µg mL−1 | Staphylococcus aureus (MIC) | [25] | |
0.78 µg mL−1 | MRSA S. aureus (MIC) | [27] | |
64 µg mL−1 | Vibrio alginolyticus (MIC) | [26] | |
32 µg mL−1 | Vibrio parahaemolyticus (MIC) | [26] | |
Antifouling | 2.6 µg mL−1 | Balanus amphitrite (EC50) | [49] |
Antifungal | 128 µg mL−1 | Cryptococcus neoformans (MIC) | [34] |
Anti-inflammatory | 11.5 µM | RAW264.7 (IC50) | [18] |
Antimalarial | 16.41 µM | Plasmodium falciparum (IC50) | [34] |
Brine shrimp lethal | 158.5 µM | LD50 | [17] |
Cholesterol acyltransferase inhibition | 22.9 µM | rabbit liver microsomes (IC50) | [22] |
Cytotoxic | 50 µg mL−1 | P388 | [39] |
9.7 µM | Hep G2 (IC50) | [20] | |
6.7 µM | HEp-2 (IC50) | [49] | |
43.77 µM | KB (IC50) | [34] | |
7.8 µM | RD (IC50) | [49] | |
53.73 µM | Vero (IC50) | [34] | |
50 µg mL−1 | incorporation of uridine, thymidine and valine in P388 | [39] | |
m-Calpain inhibition | 7.1 µM | SLLVY-AMC (IC50) | [15] |
Oxytocin binding inhibition | 67 µM | IC50 | [40] |
α-Glucosidase inhibition | 78.4 µM | IC50 | [48] |
Purpactin A (2) | |||
Antibacterial | 8 µg mL−1 | Aeromonas hydrophila (MIC) | [26] |
4 µg mL−1 | E. coli (MIC) | ||
2.42 µmol L−1 | Helicobacter pylori 129 (MIC) | [32] | |
4.83 µmol L−1 | H. pylori G27 (MIC) | ||
64 µg mL−1 | K. pneumoniae (MIC) | [26] | |
64 µg mL−1 | MRSA S. aureus (MIC) | ||
8 µg mL−1 | Micrococcus luteus (MIC) | ||
32 µg mL−1 | P. aeruginosa (MIC) | ||
16 µg mL−1 | Vibrio anguillarum (MIC) | ||
8 µg mL−1 | Vibrio harveyi (MIC) | ||
32 µg mL−1 | V. parahaemolyticus (MIC) | ||
Antifouling | 4.8 µg mL−1 | B. amphitrite (IC50) | [31] |
10 µg mL−1 | B. amphitrite (EC50) | [49] | |
Antimalarial | 5.69 µM | P. falciparum (IC50) | [34] |
Cholesterol acyltransferase inhibition | 120 µM | rat microsomes (IC50) | [6,75] |
1.2 µM | J774 (IC50) | ||
8.2 µM | rabbit liver microsomes (IC50) | [22] | |
Cytotoxic | 15.1 µM | HCT-116 (IC50) | [31] |
38.95 µM | Hep G2 (IC50) | [29] | |
50 µg mL−1 | incorporation of uridine, thymidine and valine in P388 | [39] | |
9.7 µM | J774 (IC50) | [6,75] | |
52.5 µM | KB (IC50) | [34] | |
16.4 µM | MCF-7 (IC50) | [31] | |
75.28 µM | MCF-7 (IC50) | [34] | |
41.21 µM | NIH 3 T3 (IC50) | [29] | |
32.57 µM | Vero (IC50) | [34] | |
Elastase inhibition | 37.2 µg mL−1 | IC50 | [76] |
α-Glucosidase inhibition | 80.9 µM | IC50 | [52] |
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Salvatore, M.M.; Nicoletti, R.; Fiorito, F.; Andolfi, A. Penicillides from Penicillium and Talaromyces: Chemical Structures, Occurrence and Bioactivities. Molecules 2024, 29, 3888. https://doi.org/10.3390/molecules29163888
Salvatore MM, Nicoletti R, Fiorito F, Andolfi A. Penicillides from Penicillium and Talaromyces: Chemical Structures, Occurrence and Bioactivities. Molecules. 2024; 29(16):3888. https://doi.org/10.3390/molecules29163888
Chicago/Turabian StyleSalvatore, Maria Michela, Rosario Nicoletti, Filomena Fiorito, and Anna Andolfi. 2024. "Penicillides from Penicillium and Talaromyces: Chemical Structures, Occurrence and Bioactivities" Molecules 29, no. 16: 3888. https://doi.org/10.3390/molecules29163888