New Metabolites from the Marine-Derived Fungus Aspergillus Fumigatus

A new alkaloid, fumiquinazoline K (1), and a new nordammarane triterpenoid (2), together with three known diketopiperazines (3-5) and tryptoquivaline F (6) have been isolated from a marine strain of Aspergillus fumigatus KMM 4631 associated with the soft coral Sinularia sp. Their structures were determined by HR-MS and 1D and 2D NMR. Compounds 3-5 exhibit weak cytotoxicity against cytoplasm non-specific esterase in Ehrlich carcinoma cells. Compound 3 also induces early apoptosis of the same cells in a non-toxic range of concentrations.

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Pseurotin A1 and A2, two new 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-diones from the holothurian-derived fungus Aspergillus fumigatus WFZ-25

Canadian Journal of Chemistry ◽

10.1139/v10-157 ◽

2011 ◽

Vol 89 (1) ◽

pp. 72-76 ◽

Cited By ~ 26

Author(s):

Fa-Zuo Wang ◽

De-Hai Li ◽

Tian-Jiao Zhu ◽

Min Zhang ◽

Qian-Qun Gu

Keyword(s):

Circular Dichroism ◽

Aspergillus Fumigatus ◽

Spectroscopic Data ◽

2D Nmr ◽

Esi Ms ◽

Extensive Analysis ◽

Circular Dichroïsm ◽

New Metabolites

Two new metabolites containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione core, pseurotin A1 (1) and A2 (2), as well as pseurotin A (3), were isolated from the holothurian-derived fungus Aspergillus fumigatus WFZ-25. These compounds were determined using extensive analysis of their spectroscopic data, including 1D and 2D NMR, HR-ESI-MS, and circular dichroism (CD) experiments.

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Fallaxosides C1, C2, D1 and D2, Unusual Oligosulfated Triterpene Glycosides from the Sea Cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida, Holothurioidea) and Taxonomic Status of this Animal

Natural Product Communications ◽

10.1177/1934578x1601100718 ◽

2016 ◽

Vol 11 (7) ◽

pp. 1934578X1601100 ◽

Cited By ~ 1

Author(s):

Alexandra S. Silchenko ◽

Anatoly I. Kalinovsky ◽

Sergey A. Avilov ◽

Pelageya V. Andryjaschenko ◽

Pavel S. Dmitrenok ◽

...

Keyword(s):

Mass Spectrometry ◽

Hemolytic Activity ◽

Sea Cucumber ◽

Taxonomic Status ◽

2D Nmr ◽

Carcinoma Cells ◽

Triterpene Glycosides ◽

Ehrlich Carcinoma ◽

2D Nmr Spectroscopy ◽

Spleen Lymphocytes

Four new triterpene glycosides, fallaxosides C1 (1), C2 (2), D1 (3) and D2 (4) along with the known cucumarioside A3-2 (5) and koreoside A (6) have been isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). Structures of the glycosides have been elucidated by 2D NMR spectroscopy and mass spectrometry. All of the glycosides are rare non-holostane derivatives having shortened side chains and contain pentasaccharide carbohydrate moieties with two or three sulfate groups. Structures of these triterpene glycosides and their comparison with those earlier isolated from Cucumaria spp. and Pseudocnus dubiosus leoninus allow us to suggest that the present assignment of C. fallax to the genus Pseudocnus is not correct, and this species should be assigned to the genus Cucumaria. Cytotoxic activity of glycosides 1–5 against the ascite form of mouse Ehrlich carcinoma cells and mouse spleen lymphocytes and hemolytic activity against mouse erythrocytes have been studied. The glycosides were expectedly not active in all the tests due to the absence of an 18(20)-lactone in their aglycones and the presence of several sulfate groups. There was one exception, cucumarioside A3-2 (5), which demonstrated a weak cytotoxicity against lymphocytes and moderate hemolytic activity.

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New Metabolites from the Algal Associated Marine-derived Fungus Aspergillus Carneus

Natural Product Communications ◽

10.1177/1934578x1300800809 ◽

2013 ◽

Vol 8 (8) ◽

pp. 1934578X1300800 ◽

Cited By ~ 4

Author(s):

Olesya I. Zhuravleva ◽

Shamil Sh. Afiyatullov ◽

Ekaterina A. Yurchenko ◽

Vladimir A. Denisenko ◽

Natalya N. Kirichuk ◽

...

Keyword(s):

2D Nmr ◽

Marine Strain ◽

New Metabolites

The new oxepin-containing (1) and quinazolinone (2) alkaloids and new dihydrobenzofuran derivative (3) have been isolated from a marine strain of Aspergillus carneus KMM 4638. The structures of these metabolites were determined by HR-MS and 1D and 2D NMR, along with Marfey's method.

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Colochirosides B1, B2, B3 and C, Novel Sulfated Triterpene Glycosides from the Sea Cucumber Colochirus robustus (Cucumariidae, Dendrochirotida)

Natural Product Communications ◽

10.1177/1934578x1501001014 ◽

2015 ◽

Vol 10 (10) ◽

pp. 1934578X1501001 ◽

Cited By ~ 3

Author(s):

Alexandra S. Silchenko ◽

Anatoly I. Kalinovsky ◽

Sergey A. Avilov ◽

Pelageya V. Andryjaschenko ◽

Pavel S. Dmitrenok ◽

...

Keyword(s):

Mass Spectrometry ◽

Hemolytic Activity ◽

Sea Cucumber ◽

2D Nmr ◽

Carcinoma Cells ◽

Triterpene Glycosides ◽

Ehrlich Carcinoma ◽

Cytotoxic Activities ◽

2D Nmr Spectroscopy ◽

Carbohydrate Chains

Four new triterpene glycosides, colochirosides B1 (1), B2 (2), B3 (3) and C (4) have been isolated from the sea cucumber Colochirus robustus (Cucumariidae, Dendrochirotida). Six known earlier glycosides from representatives of two families of the order Dendrochirotida have also been found in C. robustus. Structures of the glycosides have been elucidated by 2D NMR spectroscopy and mass spectrometry. All the glycosides belong to the holostane series and contain tetrasaccharide linear carbohydrate chains with one or two sulfate groups. Cytotoxic activities of glycosides 1-4 against the ascite form of mouse Ehrlich carcinoma cells and hemolytic activities against mouse erythrocytes have been studied. Hemolytic activity of the glycosides was higher than cytotoxic. Glycosides 3 and 4 demonstrated strong effects, whereas compounds 1 and 2 containing the hydroxy-group in the side chains showed moderate hemolytic activity and were not cytotoxic.

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Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral Lobophytum varium

Marine Drugs ◽

10.3390/md18040223 ◽

2020 ◽

Vol 18 (4) ◽

pp. 223

Author(s):

Chuan-Hsiang Chang ◽

Atallah F. Ahmed ◽

Tian-Sheng Yang ◽

You-Cheng Lin ◽

Chiung-Yao Huang ◽

...

Keyword(s):

Superoxide Anion ◽

Soft Coral ◽

2D Nmr ◽

Human Neutrophils ◽

Etoac Extract ◽

1H And 13C Nmr ◽

Spectroscopic Analyses ◽

Complete Assignment ◽

First Time ◽

New Metabolites

Further chemical investigation of the EtOAc extract of the soft coral Lobophytum varium resulted in the discovery of eleven new diterpenoids lobovarols F–P (1–11) of lobane– and prenyleudesmane–types, along with two known metabolites (12 and 13). The structures of the new metabolites were established by spectroscopic analyses, including 2D NMR experiments. The absolute configuration of 1 was determined using Mosher’s method. The complete assignment of 1H and 13C NMR spectroscopic data of 12 and 13 and the identification of pyran-derived moieties in the prenyleudesmanes were reported for the first time. Anti-inflammatory activities of the isolated compounds in suppressing elastase release and superoxide anion generation in human neutrophils were disclosed for 1, 2, 4, 12, and 13. A stereospecific biosynthesis for lobanes and prenyleudesmanes from the related prenylgermacranes could explain the coexistence of lobanes and prenylgermacranes in L. varium.

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Magnumosides B3, B4 and C3, Mono- and Disulfated Triterpene Tetraosides from the Vietnamese Sea Cucumber Neothyonidium (= Massinium) magnum

Natural Product Communications ◽

10.1177/1934578x1701201013 ◽

2017 ◽

Vol 12 (10) ◽

pp. 1934578X1701201 ◽

Cited By ~ 3

Author(s):

Alexandra S. Silchenko ◽

Anatoly I. Kalinovsky ◽

Sergey A. Avilov ◽

Vladimir I Kalinin ◽

Pelageya V. Andrijaschenko ◽

...

Keyword(s):

Sea Cucumber ◽

2D Nmr ◽

Carcinoma Cells ◽

Ehrlich Carcinoma ◽

Shallow Waters ◽

2D Nmr Spectroscopy ◽

Human Colorectal Carcinoma ◽

Spleen Lymphocytes ◽

Effects Of Radiation ◽

Carbohydrate Chains

Two new monosulfated triterpene glycosides, magnumosides B3 (1) and B4 (2) and one new disulfated triterpene glycoside, magnumoside C3 (3) have been isolated from the tropical Indo-West Pacific sea cucumber Neothynidium (=Massinium) magnum (Phyllophoridae, Dendrochirotida) collected in the Vietnamese shallow waters. The structures of the glycosides were elucidated by 2D NMR spectroscopy and mass-spectrometry. All the isolated glycosides are characterized by the non-holostane type aglycones having 18(16)-lactone and 7(8)-double bond and differing from each other by the side chains structures and the quantity of sulfate groups in the carbohydrate chains. The cytotoxic activity of the compounds 1–3 against mouse spleen lymphocytes and ascite form of mouse Ehrlich carcinoma cells, human colorectal carcinoma DLD-1 as well as their hemolytic effects have been studied. Magnumoside B4 (2) greatly suppressed the colony formation and decreased the size of colonies of DLD-1 cancer cells at non-cytotoxic concentrations. The study on synergism of effects of radiation and compounds 1–3 on proliferation of DLD-1 cells showed that the tested compounds almost equally enhanced antiproliferative effect of radioactive irradiation.

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Targeted Isolation of Xenicane Diterpenoids from Taiwanese Soft Coral Asterospicularia laurae

Marine Drugs ◽

10.3390/md19030123 ◽

2021 ◽

Vol 19 (3) ◽

pp. 123

Author(s):

Yu-Chi Lin ◽

Yi-Jen Chen ◽

Shu-Rong Chen ◽

Wan-Ju Lien ◽

Hsueh-Wei Chang ◽

...

Keyword(s):

Cytotoxic Effect ◽

Soft Coral ◽

Ethanol Extract ◽

2D Nmr ◽

Ionization Mass ◽

Spectroscopic Analyses ◽

Potential Source ◽

First Case ◽

The Family ◽

Mcf 7

Application of LC-MS/MS-based molecular networking indicated the ethanol extract of octocoral Asterospicularia laurae is a potential source for the discovery of new xenicane derivatives. A natural product investigation of this soft coral resulted in the isolation of four new xenicane diterpenoids, asterolaurins O‒R (1‒4), together with six known compounds, xeniolide-A (5), isoxeniolide-A (6), xeniolide-B (7), 7,8-epoxyxeniolide-B (8), 7,8-oxido-isoxeniolide-A (9), and 9-hydroxyxeniolide-F (10). The structures of isolated compounds were characterized by employing spectroscopic analyses, including 2D-NMR (COSY, HMQC, HMBC, and NOESY) and high-resolution electrospray ionization mass spectrometry (HRESIMS). Asterolaurin O is the first case of brominated tricarbocyclic type floridicin in the family Xeniidae. Concerning bioactivity, the cytotoxic activity of those isolates was evaluated. As a result, compounds 1 and 2 demonstrated a selective cytotoxic effect against the MCF-7 cell line at IC50 of 14.7 and 25.1 μM, respectively.

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