Apoptotic Activity of New Oxisterigmatocystin Derivatives from the Marine-Derived Fungus Aspergillus nomius NC06

Sponge-derived fungi have recently attracted attention as an important source of interesting bioactive compounds. Aspergillus nomius NC06 was isolated from the marine sponge Neopetrosia chaliniformis. This fungus was cultured on rice medium and yielded four compounds including three new oxisterigmatocystins, namely, J, K, and L (1, 2, and 3), and one known compound, aspergillicin A (4). Structures of the compounds were elucidated by 1D and 2D NMR spectroscopy and by high-resolution mass spectrometry. The isolated compounds were tested for cytotoxic activity against HT 29 colon cancer cells, where compounds 1, 2, and 4 exhibited IC50 values of 1.21, 2.23, and 5.62 µg/mL, respectively. Under the fluorescence microscope by using a double staining method, HT 29 cells were observed to be viable, apoptotic, and necrotic after treatment with the cytotoxic compounds 1, 2, and 4. The result shows that compounds 1 and 2 were able to induce apoptosis and cell death in HT 29 cells.

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Azaphilones from the Red Sea Fungus Aspergillus falconensis

Marine Drugs ◽

10.3390/md18040204 ◽

2020 ◽

Vol 18 (4) ◽

pp. 204 ◽

Cited By ~ 2

Author(s):

Dina H. El-Kashef ◽

Fadia S. Youssef ◽

Rudolf Hartmann ◽

Tim-Oliver Knedel ◽

Christoph Janiak ◽

...

Keyword(s):

Red Sea ◽

Cancer Cell Line ◽

2D Nmr ◽

X Ray Diffraction ◽

2D Nmr Spectroscopy ◽

Nmr Data ◽

Ic50 Values ◽

Rice Medium ◽

Optical Rotations ◽

New Compounds

The marine-derived fungus Aspergillus falconensis, isolated from sediment collected from the Canyon at Dahab, Red Sea, yielded two new chlorinated azaphilones, falconensins O and P (1 and 2) in addition to four known azaphilone derivatives (3−6) following fermentation of the fungus on solid rice medium containing 3.5% NaCl. Replacing NaCl with 3.5% NaBr induced accumulation of three additional new azaphilones, falconensins Q−S (7−9) including two brominated derivatives (7 and 8) together with three known analogues (10−12). The structures of the new compounds were elucidated by 1D and 2D NMR spectroscopy and HRESIMS data as well as by comparison with the literature. The absolute configuration of the azaphilone derivatives was established based on single-crystal X-ray diffraction analysis of 5, comparison of NMR data and optical rotations as well as on biogenetic considerations. Compounds 1, 3−9, and 11 showed NF-κB inhibitory activity against the triple negative breast cancer cell line MDA-MB-231 with IC50 values ranging from 11.9 to 72.0 µM.

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Mono- and Dimeric Xanthones with Anti-Glioma and Anti-Inflammatory Activities from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722

Marine Drugs ◽

10.3390/md20010051 ◽

2022 ◽

Vol 20 (1) ◽

pp. 51

Author(s):

Senhua Chen ◽

Heng Guo ◽

Minghua Jiang ◽

Qilin Wu ◽

Jing Li ◽

...

Keyword(s):

High Resolution Mass Spectrometry ◽

2D Nmr ◽

Crystallographic Analysis ◽

Selective Cytotoxicity ◽

X Ray ◽

Planar Structures ◽

Spectroscopic Analyses ◽

Ic50 Values ◽

Anti Inflammatory ◽

Resolution Mass

Seven new xanthones, diaporthones A−G (1−7), together with 13 known analogues, including five mono- (8−14) and six dimeric xanthones (15−20), were obtained from the ascidian-derived fungus Diaporthe sp. SYSU-MS4722. Their planar structures were established by extensive spectroscopic analyses, including 1D and 2D NMR and high-resolution mass spectrometry (HR-ESIMS). The absolute configurations of 1−7 were clearly identified by X-ray crystallographic analysis and calculation of the ECD Spectra. Compounds 15−20 showed significant anti-inflammatory activity with IC50 values between 6.3 and 8.0 μM. In addition, dimeric xanthones (15−20) showed selective cytotoxicity against T98G cell lines with IC50 values ranging from 19.5 to 78.0 μM.

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Homoadamantane and Adamantane Acylphloroglucinols from Hypericum hirsutum

Planta Medica ◽

10.1055/a-1617-7573 ◽

2021 ◽

Author(s):

Julianna Max ◽

Jörg Heilmann

Keyword(s):

Petroleum Ether Extract ◽

2D Nmr ◽

Positive Control ◽

Ionization Mass ◽

2D Nmr Spectroscopy ◽

Vitro Assay ◽

Ionization Mass Spectroscopy ◽

Ic50 Values ◽

Adamantane Skeleton

Abstract 1H NMR-guided fractionation of the petroleum ether extract of the aerial parts from Hypericum hirsutum yielded to the isolation of 19 polyprenylated polycyclic acylphloroglucinols. Structure elucidation based on 1D and 2D NMR spectroscopy together with high-resolution electrospray ionization mass spectroscopy revealed 14 acylphloroglucinols with a homoadamantane scaffold (1–14), while 5 further compounds showed an adamantane skeleton (15–19). Except for hookerione C (15), all isolated metabolites are hitherto unknown. While structurally-related metabolites have been isolated from other Hypericum species, it is the first report of admantan and homoadamantan type acylphloroglucinols in section Taeniocarpium Jaub. & Spach (Hypericaceae). The isolated compounds have been tested in a crystal violet-based in vitro assay on their properties to reduce the proliferation of human microvascular endothelial cells compared to hyperforin as the positive control. They showed a moderate reduction of proliferation with IC50 values in the range ~ 3 – 22 µM, with the homoadamantane-based compounds 2 and 4 being the most active. In addition, inhibition of the TNF-α-induced ICAM-1 expression was determined for 1 – 5, 7, and 10 – 12. Substances 3 and 12 reduced the ICAM-1 expression significantly (to 46.7% of control for 3, 62.3% for 12, at 50 µM).

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Unusual Polyhydroxylated Steroids from the Starfish Anthenoides laevigatus, Collected off the Coastal Waters of Vietnam

Molecules ◽

10.3390/molecules25061440 ◽

2020 ◽

Vol 25 (6) ◽

pp. 1440

Author(s):

Alla A. Kicha ◽

Dinh T. Ha ◽

Timofey V. Malyarenko ◽

Anatoly I. Kalinovsky ◽

Roman S. Popov ◽

...

Keyword(s):

Coastal Waters ◽

2D Nmr ◽

2D Nmr Spectroscopy ◽

Cytotoxic Effects ◽

One Dimensional ◽

The Common ◽

Polyhydroxylated Steroids ◽

New Compounds ◽

Ht 29 ◽

Inhibit Cell Proliferation

Four new polyhydroxylated steroids 1–4 were isolated along with two previously known related steroids 5 and 6 from the methanolic extract of the starfish Anthenoides laevigatus collected off the coastal waters of Vietnam. Structures of new compounds were substantially elucidated by one-dimensional (1D) and two-dimensional (2D) NMR spectroscopy and HRESIMS techniques. Heptaol 1 and hexaol 2 contain the common 5α-cholestane skeleton, while hexaol 3 and heptaol 4 have the rare among starfish steroid compounds 5β-cholestane skeleton. Compounds 1, 5, and 6 do not show cytotoxic effects against normal JB6 Cl41 and cancer HT-29 and MDA-MB-231 cells, however they inhibit cell proliferation and colony formation of cancer HT-29 and MDA-MB-231 cells.

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Cytotoxic Activity of Dihydrochalcones Isolated from Corema Album Leaves against HT-29 Colon Cancer Cells

Natural Product Communications ◽

10.1177/1934578x1300800918 ◽

2013 ◽

Vol 8 (9) ◽

pp. 1934578X1300800 ◽

Cited By ~ 2

Author(s):

Antonio J. León-González ◽

Miguel López-Lázaro ◽

José L. Espartero ◽

Carmen Martín-Cordero

Keyword(s):

Cytotoxic Activity ◽

Reactive Oxygen Species Generation ◽

Colon Adenocarcinoma ◽

Human Colon ◽

2D Nmr ◽

Positive Control ◽

H Nmr ◽

Cytotoxic Compounds ◽

Ht 29 ◽

Human Colon Adenocarcinoma

During our search for cytotoxic compounds from Andalusian vascular plants, the ethyl acetate extract from the leaves of Corema album (L.) D. Don (Ericaceae) was selected for its cytotoxic activity against the HT-29 human colon adenocarcinoma cell line. Two dihydrochalcones, 2′,4′-dihydroxydihydrochalcone (1) and 2′-methoxy-4′-hydroxydihydrochalcone (2), have been isolated from the leaves of C. album. Their structural identification was based on 1H NMR and 13C NMR data, including 2D NMR, and mass spectrometry. These compounds were subjected to the sulfhorhodamine B (SRB) cytotoxic assay against human colon adenocarcinoma cells (HT-29). Compounds 1 and 2 showed higher cytotoxicity than the positive control 5-fluorouracil (5-FU); the IC50 values (μM ± SEM) were 1.8 ± 0.4 for compound 1, 8.5 ± 2.1 μM for compound 2, and 8.7 ± 4.0 for 5-FU. The cytotoxic activity of 1 and 2 was reduced in the presence of the antioxidants N-acetylcysteine (NAC) and Mn(III) Tetrakis(1-methyl-4-pyridyl) porphyrin pentachloride (MnTMPyP), therefore suggesting that reactive oxygen species generation participates in the cytotoxic activity of these dihydrochalcones.

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A New Glucuronolactone Glycoside Phoenixoside B from the Seeds of Phoenix Dactylifera

Natural Product Communications ◽

10.1177/1934578x1300800926 ◽

2013 ◽

Vol 8 (9) ◽

pp. 1934578X1300800

Author(s):

Sumbul Azmat ◽

Rehana Ifzal ◽

Faryal Vali Mohammad ◽

Viqar Uddin Ahmad ◽

Aqib Zahoor

Keyword(s):

Mass Spectrometry ◽

Nmr Spectroscopy ◽

High Resolution ◽

High Resolution Mass Spectrometry ◽

Soluble Fraction ◽

2D Nmr ◽

Phoenix Dactylifera ◽

2D Nmr Spectroscopy ◽

High Resolution Mass ◽

Resolution Mass

A new glucuronolactone glycoside, phoenixoside B (1), has been isolated from the n-butanol soluble fraction of seeds of Phoenix dactylifera. The structure was characterized as 1-(1-ethyl-β-D-glucosyl)-4,5-diethyl-[α-D-glucofuranourono-6,3-lactone] on the basis of 1D and 2D-NMR spectroscopy and high-resolution mass spectrometry.

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New depsidones and isoindolinones from the mangrove endophytic fungus Meyerozyma guilliermondii (HZ-Y2) isolated from the South China Sea

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.11.133 ◽

2015 ◽

Vol 11 ◽

pp. 1187-1193 ◽

Cited By ~ 19

Author(s):

Senhua Chen ◽

Zhaoming Liu ◽

Yayue Liu ◽

Yongjun Lu ◽

Lei He ◽

...

Keyword(s):

Endophytic Fungus ◽

High Resolution Mass Spectrometry ◽

Kinetic Studies ◽

2D Nmr ◽

Kandelia Obovata ◽

2D Nmr Spectroscopy ◽

Mangrove Plant ◽

Meyerozyma Guilliermondii ◽

Mangrove Endophytic Fungus ◽

Noncompetitive Inhibitors

Three new depsidones, botryorhodines E–G (1–3), and two new isoindolinones, meyeroguillines A and B (7 and 9), along with five known compounds were isolated from an endophytic fungus Meyerozyma guilliermondii, derived from the mangrove plant Kandelia obovata. Their structures were elucidated by 1D and 2D NMR spectroscopy and high resolution mass spectrometry (HREIMS). Compounds 1–6 exhibited strong α-glucosidase inhibitory activity with IC50 values ranging from 2.1 to 13.3 μM. Moreover, kinetic studies of compounds 2 and 6 showed that both of them were noncompetitive inhibitors of α-glucosidase.

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A New Sesquiterpene Lactone Sulfate from Reichardia gaditana (Asteraceae)

Zeitschrift für Naturforschung B ◽

10.1515/znb-2007-0121 ◽

2007 ◽

Vol 62 (1) ◽

pp. 132-134 ◽

Cited By ~ 8

Author(s):

Christian Zidorn ◽

Ernst-Peter Ellmerer ◽

Werner Heller ◽

Richard Greil ◽

Manuela Guggenberger ◽

...

Keyword(s):

Mass Spectrometry ◽

Nmr Spectroscopy ◽

High Resolution ◽

Structure Elucidation ◽

Methanolic Extract ◽

High Resolution Mass Spectrometry ◽

2D Nmr ◽

2D Nmr Spectroscopy ◽

Asteraceae Family ◽

Resolution Mass

The new sesquiterpenoid 8-deoxy-15-(3′-hydroxy-2′-methyl-propanoyl)-lactucin 3′-sulfate (1) was isolated from the methanolic extract of roots of Reichardia gaditana L. The compound was isolated by silica gel column chromatography (CC) and repeated Sephadex LH-20 CC. Structure elucidation was accomplished by high-resolution mass spectrometry and by 1D- and 2D-NMR spectroscopy. The chemosystematic significance of the new compound is discussed in the context of sesquiterpenoids from other members of the Lactuceae tribe of the Asteraceae family.

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A New Megastigmane Glycoside, Phoenixoside A, from Phoenix Dactylifera

Natural Product Communications ◽

10.1177/1934578x1200700103 ◽

2012 ◽

Vol 7 (1) ◽

pp. 1934578X1200700

Author(s):

Sumbul Azmat ◽

Aqib Zahoor ◽

Rehana Ifzal ◽

Viqar Uddin Ahmad ◽

Faryal Vali Mohammed

Keyword(s):

Mass Spectrometry ◽

Nmr Spectroscopy ◽

High Resolution ◽

High Resolution Mass Spectrometry ◽

Soluble Fraction ◽

2D Nmr ◽

Phoenix Dactylifera ◽

Cd Spectroscopy ◽

2D Nmr Spectroscopy ◽

Resolution Mass

A new megastigmane glycoside, phoenixoside A (1), has been isolated from the n-butanol - soluble fraction of seeds of Phoenix dactylifera. The structure was characterized as (6S,7Z,9R)-hydroxy-3-oxo-ionol-9- O-β-D-glucopyranosyl-(1″→6′)-β-D–glucopyranoside on the basis of 1D and 2D NMR spectroscopy, high-resolution mass spectrometry, and CD spectroscopy.

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Targeted Isolation of a Cytotoxic Cyclic Hexadepsipeptide from the Mesophotic Zone Sponge-Associated Fungus Cymostachys sp. NBUF082

Marine Drugs ◽

10.3390/md19100565 ◽

2021 ◽

Vol 19 (10) ◽

pp. 565

Author(s):

Ye Yuan ◽

Te Li ◽

Tingting Wang ◽

C. Benjamin Naman ◽

Jing Ye ◽

...

Keyword(s):

Acute Lymphocytic Leukemia ◽

High Resolution Mass Spectrometry ◽

2D Nmr ◽

Lymphocytic Leukemia ◽

Leukemia Cells ◽

Chiral Hplc ◽

2D Nmr Spectroscopy ◽

Ic50 Value ◽

Resolution Mass

LC-MS/MS-based molecular networking facilitated the targeted isolation of a new cyclic hexadepsipeptide, cymodepsipeptide (1), and two known analogues, RF–2691A (2) and RF–2691B (3), from the fungus Cymostachys sp. NBUF082 that was derived from a mesophotic zone Aaptos sponge collected near Apo Island. The constitution and configuration of 1 was elucidated through 1D and 2D NMR-spectroscopy, high resolution mass-spectrometry, and chemical degradations including Marfey’s analysis and chiral HPLC. It was observed that 1 was moderately cytotoxic against CCRF-CEM human acute lymphocytic leukemia cells in vitro with the IC50 value of 9.2 ± 1.1 μM.

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