Austalides V and W, new meroterpenoids from the fungus Aspergillus ustus and their antitumor activities

Антипова, Т. В.; Zaitsev, Kirill V.; Oprunenko, Yuri F.; Zherebker, Alexander; Rystsov, Gleb K.; Zemskova, Marina; Желифонова, В. П.; Ivanushkina, N. E.; Kozlovsky, A. G.

doi:10.1016/j.bmcl.2019.126708

Cited by 13 publications

(22 citation statements)

References 21 publications

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“…31 The polyketides described here add to the large chemical diversity of metabolites from Aspergillus subgenus Nidulantes. 1,9,32 So far in the genus Aspergillus, polyketides with a phthalide moiety include several from subgenus Fumigati section Fumigati (Aspergillus duricaulis), 33 others from subgenus Nidulantes, including asperlide in A. unguis, 34 porriolides (silvaticols, and the nitrogen-containing cichorine) in A. nidulans and A. silvaticus, 35,36 emefuranones in an Aspergillus ("Emericella") species from section Usti or Cavernicolarum, 29 austalides in A. ustus, 37 A. aureolatus, 38 and A. alabamensis, 39 and mycophenolic acids from subgenus Aspergillus section Restricti (A. glabripes, A. gracilis, A. pachycaulis, A. penicillioides, and A. tardicrescens), 40 section Aspergillus (A. pseudoglaucus), 41 and also from subgenus Fumigati section Fumigati (A. unilaterialis). 42 However, none of those phthalides resemble 2−4 except the emefuranones.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Taxonomy Driven Discovery of Polyketides from Aspergillus californicus

et al. 2021

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Five new polyketides were isolated from the rare filamentous fungus Aspergillus californicus IBT 16748 including calidiol A (1); three phthalide derivatives califuranones A1, A2, and B (2–4); and a pair of enantiomers (−)-calitetralintriol A (−5) and (+)-calitetralintriol A (+5) together with four known metabolites (6–9). The structures of the new products were established by extensive spectroscopic analyses including HRMS and 1D and 2D NMR. The absolute configurations of two diastereomers 2 and 3 and the enantiomers (−5) and (+5) were assigned by comparing their experimental and calculated ECD data, whereas the absolute configuration of 4 was proposed by analogy. Compound 1 showed moderate activity against methicillin-resistant Staphylococcus aureus.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Taxonomy Driven Discovery of Polyketides from Aspergillus californicus

et al. 2021

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“…The isolated compounds were also evaluated for their inhibitory effects against NO production in LPS-activated RAW 264.7 macrophages at the concentration of 50 µM following the same procedures in our previous study [10]. The cell viability was further determined by the MTT assay to evaluate whether the inhibition on NO production was owing to the cytotoxicity.…”

Section: Compoundmentioning

confidence: 99%

“…These meroterpenoids were mainly produced by the species of the fungal genera Aspergillus and Penicillium, especially those from marine environments. Since austalides A−E were first reported in 1981, a total of 36 analogues have been identified [2][3][4][5][6][7][8][9][10][11]. The structural variations of austalides are attributed to oxidation occurring at C-13, C-14, C-17, and the isopropyl (C-15, C-25, C-26) to generate alcohol, isopropenyl, lactone, ester, or ether functionalities.…”

Section: Introductionmentioning

confidence: 99%

“…The structural variations of austalides are attributed to oxidation occurring at C-13, C-14, C-17, and the isopropyl (C-15, C-25, C-26) to generate alcohol, isopropenyl, lactone, ester, or ether functionalities. Some of the analogues exhibited significant bioactivities, such as cytotoxicity [6,10] antibacterial activity [7], anti-influenza A virus (H1N1) activity [8], endo-1,3-D-glucanase inhibition [9], and osteoclast differentiation inhibitory effects [11].…”

Section: Introductionmentioning

confidence: 99%

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Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities

et al. 2020

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A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus Penicillium thomii YPGA3 led to the isolation of a new austalide meroterpenoid (1) and seven known analogues (2−8), two new labdane-type diterpenoids (9 and 10) and a known derivative (11). The structures of new compounds 1, 9, and 10 were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of 1, 9, and 10 were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound 1 represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of Penicillium for the first time. Compound 1 showed cytotoxicity toward MDA-MB-468 cells with an IC50 value of 38.9 μM. Compounds 2 and 11 exhibited inhibition against α-glucosidase with IC50 values of 910 and 525 μM, respectively, being more active than the positive control acarbose (1.33 mM).

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“…5‐ ( 3 ’, 3 ’ ‐dimethylallyloxy ) ‐7‐hydroxy‐6‐methylphthalide ( 11 ) which is isolated from cultures of the basidiomycete Albatrellus confluens shows strong cytotoxic activity against hepatocellular carcinoma cell line (SMMC‐7721) with IC 50 values of 1.81 μM [52] . Austalide W ( 12 ) is isolated from the fungus Aspergillus ustus VKM F‐4692, affecting negatively proliferation and migration of prostate and bladder cancer cells [53] . Mycophenolic acid (MPA) ( 13 ), which was isolated as a fermentation product of Penicillium stoloniferum has antifungal, antibacterial, antiviral, and immunosuppressive activities, [54,55] and its morpholino ester ‐ mycophenolate mofetil (MMF) ( 14 ) ‐ is widely used in solid organ transplantation to prevent rejection [55–57] (Figure 3) etc.…”

Section: Introductionmentioning

confidence: 99%

An Overview of Natural and Synthetic Phthalides Involved in Cancer Studies: Past, Present, and Future

et al. 2022

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Phthalides, mainly isolated from two genera: Ligusticum and Angelica of the Apiceae (syn Umbelliferae) family, are thought to be a potent natural compound with many therapeutic effects, such as antiplatelet, antitussive, antinociceptive, anti‐inflammatory, antibacterial, antiviral, and immunosuppressive activities. They also have antifungal, antioxidant, and anticancer activities. Phthalides are responsible for the characteristic odor of celery. Since ancient times, phthalides containing plants have been used in Asia, Europe, and North America as traditional medicines and food flavoring agents. In this review, we have provided the data regarding the mechanisms of action related with phthalides on different cancer cells, their chemopreventive properties, and their possible therapeutic potential against various types of human cancer. Our attempt is to make a case for the use of phthalide and their derivatives as one of the plant‐based compounds in targeting metabolic treatment of cancer diseases.

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Austalides V and W, new meroterpenoids from the fungus Aspergillus ustus and their antitumor activities

Cited by 13 publications

References 21 publications

Taxonomy Driven Discovery of Polyketides from Aspergillus californicus

Taxonomy Driven Discovery of Polyketides from Aspergillus californicus

Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities

An Overview of Natural and Synthetic Phthalides Involved in Cancer Studies: Past, Present, and Future

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