Two New Cytotoxic Compounds from a Deep-Sea Penicillum citreonigrum XT20-134

Penicillum citreonigrum XT20-134 (MCCC 3A00956) is a fungus with cytotoxic activity, derived from deep-sea sediment. Five new compounds, adeninylpyrenocine (1), 2-hydroxyl-3-pyrenocine-thio propanoic acid (2), ozazino-cyclo-(2,3-dihydroxyl-trp-tyr) (3), 5,5-dichloro-1-(3,5-dimethoxyphenyl)-1,4-dihydroxypentan-2-one (4), and 2,3,4-trihydroxybutyl cinnamate (5), together with 19 known compounds (6–24), were isolated from an ethyl acetate (EtOAc) extract of its fermentation. The structures of the new compounds were comprehensively characterized by high-resolution electrospray ionization-mass spectrometry (HR-ESI-MS), 1D and 2D nuclear magnetic resonance (NMR). All isolates were evaluated for their cytotoxic activities. The heteroatom-containing new compounds 2 and 4 showed potent cytotoxicity to the human hepatoma tumor cell Bel7402 with IC50 values of 7.63 ± 1.46, 13.14 ± 1.41 μM and the human fibrosarcoma tumor cell HT1080 with IC50 values of 10.22 ± 1.32, 16.53 ± 1.67 μM, respectively.

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

Marine Drugs ◽

10.3390/md18030164 ◽

2020 ◽

Vol 18 (3) ◽

pp. 164 ◽

Cited By ~ 1

Author(s):

Zhongbin Cheng ◽

Wan Liu ◽

Runzhu Fan ◽

Shouye Han ◽

Yuanli Li ◽

...

Keyword(s):

Deep Sea ◽

Chemical Study ◽

Positive Control ◽

Hydroxyl Group ◽

Etoac Extract ◽

The Third ◽

Ic50 Value ◽

Ic50 Values ◽

New Compounds ◽

First Time

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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Cytotoxic Polyketides from a Deep-Sea Sediment Derived Fungus Diaporthe phaseolorum FS431

Molecules ◽

10.3390/molecules24173062 ◽

2019 ◽

Vol 24 (17) ◽

pp. 3062 ◽

Cited By ~ 1

Author(s):

Zheng Niu ◽

Yuchan Chen ◽

Heng Guo ◽

Sai-Ni Li ◽

Hao-Hua Li ◽

...

Keyword(s):

Tumor Cell ◽

Cell Lines ◽

Deep Sea ◽

Human Tumor ◽

Electron Capture Detection ◽

Cytotoxic Activities ◽

Tumor Cell Lines ◽

Deep Sea Sediment ◽

Diaporthe Phaseolorum

Two new chromone-derived polyketides phaseolorins, G and H (1 and 2), and one new anthraquinone derivative, phaseolorin I (3), together with three known compounds (4–6), were isolated from the deep-sea sediment-derived fungus Diaporthe phaseolorum FS431. The structures of the new compounds were determined by comprehensive analysis of their spectroscopic data, and the absolute configuration of 1 was established by quantum chemical calculations of electron capture detection (ECD). All the isolated compounds (1–6) were tested for their in vitro cytotoxic activities against four human tumor cell lines, of which compound 4 exhibited significant effect against MCF-7, HepG-2, and A549 tumor cell lines with IC50 values of 2.60, 2.55, and 4.64 µM, respectively.

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Chromone-Derived Polyketides from the Deep-Sea Fungus Diaporthe phaseolorum FS431

Marine Drugs ◽

10.3390/md17030182 ◽

2019 ◽

Vol 17 (3) ◽

pp. 182 ◽

Cited By ~ 4

Author(s):

Heng Guo ◽

Zhao-Ming Liu ◽

Yu-Chan Chen ◽

Hai-Bo Tan ◽

Sai-Ni Li ◽

...

Keyword(s):

Deep Sea ◽

Human Cancer ◽

Electron Capture Detection ◽

Cytotoxic Activities ◽

Ionization Mass ◽

Chemical Transformations ◽

Human Cancer Cell Lines ◽

Diaporthe Phaseolorum ◽

New Compounds

Five new chromone-derived polyketides phaseolorins A-F (1–5), together with nine known compounds, were isolated from the deep-sea derived fungus Diaporthe phaseolorum FS431. The structures of new compounds were determined by analysis of their NMR and high-resolution electrospray ionization mass spectroscopy (HRESIMS) spectroscopic data. The absolute configurations were confirmed by chemical transformations, extensively experimental electron capture detection (ECD) calculations, or X-ray crystallography. Among them, compound 2 represented the first example for a new family of chromone derivative possessing an unprecedented recombined five-member γ-lactone ring. Moreover, the new compounds (1–5) were evaluated for in vitro cytotoxic activities against a panel of human cancer cell lines.

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Antibacterial and Cytotoxic Phenolic Polyketides from Two Marine-Derived Fungal Strains of Aspergillus unguis

Pharmaceuticals ◽

10.3390/ph15010074 ◽

2022 ◽

Vol 15 (1) ◽

pp. 74

Author(s):

Cao Van Anh ◽

Joo-Hee Kwon ◽

Jong Soon Kang ◽

Hwa-Sun Lee ◽

Chang-Su Heo ◽

...

Keyword(s):

Tumor Cell ◽

Detailed Analysis ◽

Cell Lines ◽

Spectroscopic Data ◽

Bacterial Activity ◽

Tumor Cell Lines ◽

Fungal Strains ◽

Aspergillus Unguis ◽

Ic50 Values ◽

New Compounds

A chemical investigation on the EtOAc extracts from two marine-derived fungal strains of Aspergillus unguis resulted in the isolation of three previously undescribed phenolic polyketides including unguidepside C (1), aspersidone B (3), and agonodepside C (12), and their 14 known congeners. The structures of the new compounds were determined based on detailed analysis and comparison of their spectroscopic data with literature values, as well as Snatzke’s method. The new compounds (1, 3, and 12) displayed a significant anti-Gram-positive bacterial activity, with MIC values ranging from 5.3 to 22.1 µM. Additionally, the isolated compounds (1–11 and 13–16) were evaluated for their cytotoxicity against a panel of tumor cell lines. Most of them (except for 9) displayed cytotoxicity against all the tested cell lines, with IC50 values ranging from 2.5 to 46.9 µM.

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Dechdigliotoxins A–C, Three Novel Disulfide-Bridged Gliotoxin Dimers from Deep-Sea Sediment Derived Fungus Dichotomomyces cejpii

Marine Drugs ◽

10.3390/md17110596 ◽

2019 ◽

Vol 17 (11) ◽

pp. 596 ◽

Cited By ~ 5

Author(s):

Zhaoming Liu ◽

Zhen Fan ◽

Zhanghua Sun ◽

Hongxin Liu ◽

Weimin Zhang

Keyword(s):

Tumor Cell ◽

Quantum Chemical Calculations ◽

Cell Lines ◽

Deep Sea ◽

Quantum Chemical ◽

Biosynthetic Pathway ◽

Spectroscopic Analysis ◽

Tumor Cell Lines ◽

Disulfide Linkage ◽

Deep Sea Sediment

Dechdigliotoxins A–C (1–3), which represented the first examples of gliotoxin dimers with an unprecedented exocyclic disulfide linkage, were obtained from a deep-sea derived fungus Dichotomomyces cejpii FS110. The structures of these compounds were elucidated on the basis of spectroscopic analysis and the absolute configurations were unambiguously determined through quantum chemical calculations, as well as DP4+ probability simulations. The proposed biosynthetic pathway suggested 1–3 were generated from unusual L-Phe and D-Ser. All the isolates were evaluated for their cytotoxicity against four tumor cell lines.

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Highly Substituted Benzophenone Aldehydes and Eremophilane Derivatives from the Deep-Sea Derived Fungus Phomopsis lithocarpus FS508

Marine Drugs ◽

10.3390/md16090329 ◽

2018 ◽

Vol 16 (9) ◽

pp. 329 ◽

Cited By ~ 9

Author(s):

Jian-Lin Xu ◽

Hong-Xin Liu ◽

Yu-Chan Chen ◽

Hai-Bo Tan ◽

Heng Guo ◽

...

Keyword(s):

Cytotoxic Activity ◽

Cell Lines ◽

A549 Cell ◽

Marine Sediment ◽

Deep Sea ◽

Crystallographic Analysis ◽

X Ray ◽

Naturally Occurring ◽

Ic50 Values ◽

New Compounds

Five new benzophenone derivatives named tenellones D–H (1–5), sharing a rare naturally occurring aldehyde functionality in this family, and a new eremophilane derivative named lithocarin A (7), together with two known compounds (6 and 8), were isolated from the deep marine sediment-derived fungus Phomopsis lithocarpus FS508. All of the structures for these new compounds were fully characterized and established on the basis of extensive spectroscopic interpretation and X-ray crystallographic analysis. Compound 5 exhibited cytotoxic activity against HepG-2 and A549 cell lines with IC50 values of 16.0 and 17.6 μM, respectively.

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Cytotoxic Polyketides from the Marine Sponge-Derived Fungus Pestalotiopsis heterocornis XWS03F09

Molecules ◽

10.3390/molecules24142655 ◽

2019 ◽

Vol 24 (14) ◽

pp. 2655 ◽

Cited By ~ 2

Author(s):

Lei ◽

Zhou ◽

Hu ◽

Niu ◽

...

Keyword(s):

Marine Sponge ◽

Spectroscopic Analysis ◽

Fermentation Broth ◽

Human Cancer ◽

Optical Rotation ◽

Cytotoxic Activities ◽

Human Cancer Cell Lines ◽

Chemical Structures ◽

Ic50 Values ◽

New Compounds

Four new compounds, including two new polyketides, heterocornols M and N (1, 2), and a pair of epimers, heterocornols O and P (3, 4), were isolated from the fermentation broth of the marine sponge-derived fungus Pestalotiopsis heterocornis XWS03F09, together with three known compounds (5–7). The new chemical structures were established on the basis of a spectroscopic analysis, optical rotation, experimental and calculated electronic circular dichroism (ECD). All of the compounds (1–7) were evaluated for their cytotoxic activities, and heterocornols M-P (1–4) exhibited cytotoxicities against four human cancer cell lines with IC50 values of 20.4–94.2 μM.

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20-Nor-isopimarane cycloethers from the deep-sea sediment-derived fungus Aspergillus wentii SD-310

RSC Advances ◽

10.1039/c6ra17638k ◽

2016 ◽

Vol 6 (79) ◽

pp. 75981-75987 ◽

Cited By ~ 13

Author(s):

Xin Li ◽

Xiao-Ming Li ◽

Xiao-Dong Li ◽

Gang-Ming Xu ◽

Yang Liu ◽

...

Keyword(s):

Tumor Cell ◽

Cell Lines ◽

Deep Sea ◽

Tumor Cell Lines ◽

Deep Sea Sediment ◽

Aspergillus Wentii ◽

Tetracyclic System

Five new 20-nor-isopimaranes, asperethers A–E (1–5), were isolated from the deep-sea derived fungus Aspergillus wentii SD-310. These compounds possess a unique 6/6/6/5 tetracyclic system and exhibited cytotoxicity against several tumor cell lines.

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New Antiproliferative Compounds against Glioma Cells from the Marine-Sourced Fungus Penicillium sp. ZZ1750

Marine Drugs ◽

10.3390/md19090483 ◽

2021 ◽

Vol 19 (9) ◽

pp. 483

Author(s):

Kuo Yong ◽

Sidra Kaleem ◽

Bin Wu ◽

Zhizhen Zhang

Keyword(s):

Chemical Degradation ◽

Ionization Mass ◽

X Ray Diffraction ◽

Penicillium Sp ◽

Electrospray Ionization Mass Spectroscopy ◽

Ionization Mass Spectroscopy ◽

Ic50 Values ◽

Rice Medium ◽

Antiglioma Activity ◽

New Compounds

Seven novel compounds, namely peniresorcinosides A–E (1–5), penidifarnesylin A (6), and penipyridinone A (7), together with the 11 known ones 8–17, were isolated from a culture of the marine-associated fungus Penicillium sp. ZZ1750 in rice medium. The structures of the new compounds were established based on their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses, chemical degradation, Mosher’s method, 13C-NMR calculations, electronic circular dichroism (ECD) calculations, and single crystal X-ray diffraction. Peniresorcinosides A (1) and B (2) are rare glycosylated alkylresorcinols and exhibited potent antiglioma activity, with IC50 values of 4.0 and 5.6 µM for U87MG cells and 14.1 and 9.8 µM for U251 cells, respectively.

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