Phenylhydrazone and Quinazoline Derivatives from the Cold-Seep-Derived Fungus Penicillium oxalicum

Three new phenylhydrazones, penoxahydrazones A–C (compounds 1–3), and two new quinazolines, penoxazolones A (compound 4) and B (compound 5), with unique linkages were isolated from the fungus Penicillium oxalicum obtained from the deep sea cold seep. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and mass spectroscopic data, and the absolute configurations of 1, 4, and 5 were established on the basis of X-ray crystallography or ECD calculations. Compound 1 represents the first natural phenylhydrazone-bearing steroid, while compounds 2 and 3 are rarely occurring phenylhydrazone tautomers. Compounds 4 and 5 are enantiomers that feature quinazoline and cinnamic acid units. Some isolates exhibited inhibition of several marine phytoplankton species and marine-derived bacteria.

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Anti-Food Allergic Compounds from Penicillium griseofulvum MCCC 3A00225, a Deep-Sea-Derived Fungus

Marine Drugs ◽

10.3390/md19040224 ◽

2021 ◽

Vol 19 (4) ◽

pp. 224

Author(s):

Cui-Ping Xing ◽

Dan Chen ◽

Chun-Lan Xie ◽

Qingmei Liu ◽

Tian-Hua Zhong ◽

...

Keyword(s):

Deep Sea ◽

Spectroscopic Data ◽

Positive Control ◽

X Ray ◽

X Ray Crystallography ◽

Ic50 Value ◽

Penicillium Griseofulvum ◽

New Compounds ◽

Basophilic Leukemia

Ten new (1–10) and 26 known (11–36) compounds were isolated from Penicillium griseofulvum MCCC 3A00225, a deep sea-derived fungus. The structures of the new compounds were determined by detailed analysis of the NMR and HRESIMS spectroscopic data. The absolute configurations were established by X-ray crystallography, Marfey’s method, and the ICD method. All isolates were tested for in vitro anti-food allergic bioactivities in immunoglobulin (Ig) E-mediated rat basophilic leukemia (RBL)-2H3 cells. Compound 13 significantly decreased the degranulation release with an IC50 value of 60.3 μM, compared to that of 91.6 μM of the positive control, loratadine.

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Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227

Marine Drugs ◽

10.3390/md19060305 ◽

2021 ◽

Vol 19 (6) ◽

pp. 305

Author(s):

Guangyuan Luo ◽

Li Zheng ◽

Qilin Wu ◽

Senhua Chen ◽

Jing Li ◽

...

Keyword(s):

Fusarium Solani ◽

2D Nmr ◽

Inflammatory Activity ◽

Raw264.7 Cells ◽

Spectroscopic Methods ◽

X Ray ◽

X Ray Crystallography ◽

Structure Activity ◽

Ic50 Values ◽

New Compounds

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.

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Crotaleschenine, an Alkaloid of Crotalaria leschenaultii

Australian Journal of Chemistry ◽

10.1071/ch9880429 ◽

1988 ◽

Vol 41 (4) ◽

pp. 429 ◽

Cited By ~ 6

Author(s):

LW Smith ◽

JA Edgar ◽

RI Willing ◽

RW Gable ◽

MF Mackay ◽

...

Keyword(s):

Spectroscopic Data ◽

X Ray ◽

X Ray Crystallography

An alkaloid of Crotalaria leschenaultii DC., previously reported as crispatine and now named crotaleschenine, has been re-investigated and shown to be (7β,8α-H,12α,13α,14α)-12β-hydroxy-1,2-didehydrocrotalane-11,15-dione.1 Spectroscopic data are presented and the stereochemistry determined by X-ray crystallography. The esterifying acid of crotaleschenine is identical with that of retusine , which is thereby determined as (1a,7β,8α-H,12α,13α,14α)-12β- hydroxycrotalane-11,15-dione.

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Secondary Metabolites with Nitric Oxide Inhibition from Marine-Derived Fungus Alternaria sp. 5102

Marine Drugs ◽

10.3390/md18080426 ◽

2020 ◽

Vol 18 (8) ◽

pp. 426 ◽

Cited By ~ 1

Author(s):

Senhua Chen ◽

Yanlian Deng ◽

Chong Yan ◽

Zhenger Wu ◽

Heng Guo ◽

...

Keyword(s):

Secondary Metabolites ◽

2D Nmr ◽

X Ray ◽

X Ray Crystallography ◽

Spectroscopic Analyses ◽

Structure Activity ◽

Ic50 Values ◽

Alternaria Sp ◽

Modified Mosher’S Method ◽

Oxide Inhibition

Two new benzofurans, alternabenzofurans A and B (1 and 2) and two new sesquiterpenoids, alternaterpenoids A and B (3 and 4), along with 18 known polyketides (5−22), were isolated from the marine-derived fungus Alternaria sp. 5102. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HR-ESIMS, and ECD) and X-ray crystallography, as well as the modified Mosher’s method. Compounds 2, 3, 5, 7, 9–18, and 20–22 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50 values in the range from 1.3 to 41.1 μM. Structure-activity relationships of the secondary metabolites were discussed.

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Cyclonerane Derivatives from the Algicolous Endophytic Fungus Trichoderma asperellum A-YMD-9-2

Marine Drugs ◽

10.3390/md17050252 ◽

2019 ◽

Vol 17 (5) ◽

pp. 252 ◽

Cited By ~ 2

Author(s):

Yin-Ping Song ◽

Feng-Ping Miao ◽

Xiang-Hong Liu ◽

Xiu-Li Yin ◽

Nai-Yun Ji

Keyword(s):

Endophytic Fungus ◽

Structural Diversity ◽

2D Nmr ◽

Red Alga ◽

Gracilaria Verrucosa ◽

Marine Phytoplankton ◽

Spectroscopic Techniques ◽

Phytoplankton Species ◽

Trichoderma Asperellum ◽

Potent Inhibition

Seven previously unreported cyclonerane derivatives, namely, 3,7,11-trihydroxycycloneran-10-one, cycloneran-3,7,10,11-tetraol, cycloneran-3,7,11-triol, 11,12,15-trinorcycloneran-3,7,10-triol, 7,10S-epoxycycloneran-3,15-diol, 7,10R-epoxycycloneran-3,15-diol, and (10Z)-15-acetoxy-10-cycloneren-3,7-diol, were isolated in addition to the known (10Z)-cyclonerotriol, (10E)-cyclonerotriol, catenioblin C, and chokol E from the culture of Trichoderma asperellum A-YMD-9-2, an endophytic fungus obtained from the marine red alga Gracilaria verrucosa. The structures of previously unreported compounds were established by spectroscopic techniques, including 1D/2D NMR, MS, and IR. The isolation of these new cyclonerane derivatives greatly adds to the structural diversity of unusual cyclonerane sesquiterpenes, and several isolates exhibit potent inhibition against some marine phytoplankton species.

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Mononuclear and Binuclear Complexes of Platinum(0) Containing (Alkynyl)phenylsilanes

Australian Journal of Chemistry ◽

10.1071/c98135 ◽

1999 ◽

Vol 52 (1) ◽

pp. 51 ◽

Cited By ~ 4

Author(s):

Martin A. Bennett ◽

Christopher J. Cobley ◽

David C. R. Hockless ◽

Thomas Klettke

Keyword(s):

Spectroscopic Data ◽

Chair Conformation ◽

Membered Ring ◽

Binuclear Complexes ◽

Nickel Compound ◽

X Ray ◽

X Ray Crystallography

Reaction of bis(cycloocta-1,5-diene)platinum(0) with the (alkynyl)phenylsilanes Ph3SiC2But, Ph2Si(C2But)2 and PhSi(C2But)3 gives, respectively, [Pt (Ph3SiC2But)2] (1b), [Pt {Ph2Si(C2But)}]2 (2b), and [Pt {PhSi(C2But)3}]2 (4b), which contain zerovalent platinum atoms coordinated by two alkyne units. Spectroscopic data indicate that (2b) and (4b) contain two PtC4 and two SiC4 tetrahedra joined at the corners. X-Ray crystallography shows that complex (4b) is isostructural and isomorphous with the known nickel analogue, two of the alkyne units being uncoordinated; the central eight-membered ring comprising two silicon, four alkyne carbon and two platinum atoms has an approximate chair conformation. In contrast, the monomer (1b) is isostructural but not isomorphous with the analogous nickel compound (1a); in the crystal there is evidence for a weak intramolecular phenyl-phenyl interaction.

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Sesquiterpene Lactones from Inula oculus-christi

Natural Product Communications ◽

10.1177/1934578x1000500402 ◽

2010 ◽

Vol 5 (4) ◽

pp. 1934578X1000500 ◽

Cited By ~ 5

Author(s):

Mahmoud Mosaddegh ◽

Maryam Hamzeloo Moghadam ◽

Saeedeh Ghafari ◽

Farzaneh Naghibi ◽

Seyed Nasser Ostad ◽

...

Keyword(s):

Cytotoxic Activity ◽

Crystal Structures ◽

Spectroscopic Data ◽

Sesquiterpene Lactones ◽

X Ray ◽

X Ray Crystallography ◽

First Time

Inula oculus-christi L. (Compositae) extract was chromatographed and three sesquiterpene lactones ergolide, gaillardin and pulchellin C were isolated. The structures of these compounds were determined by analysis of their spectroscopic data, and their crystal structures were defined using X-ray crystallography; the isolation of ergolide and pulchellin C is reported for the first time from this species. These three compounds were evaluated for their in vitro cytotoxic activity against MDBK, MCF7 and WEHI164 cells; ergolide and gaillardin exhibited lower and significantly different IC50 values compared with pulchellin C ( p<0.001).

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Übergangsmetall-Carben-Komplexe, CXXXIV [1]. Synthese neuer Mono- und Biscarben-Komplexe der VI. Nebengruppe; Röntgenstruktur des ersten Bis[amino(alkoxy)carben]-Komplexes / Transition Metal Carbene Complexes, CXXXIV [1]. Synthesis of New Mono- and Bis-Carbene Complexes of Group VIb Elements; Structure of the First Bis[amino(alkoxy)carbene]-Complex

Zeitschrift für Naturforschung B ◽

10.1515/znb-1984-0522 ◽

1984 ◽

Vol 39 (5) ◽

pp. 668-674 ◽

Cited By ~ 13

Author(s):

Ernst Otto Fischer ◽

Rudolf Reitmeier ◽

Klaus Ackermann

Keyword(s):

Molecular Structure ◽

Transition Metal ◽

Spectroscopic Data ◽

The Novel ◽

Nucleophilic Agent ◽

Reaction Conditions ◽

Carbene Complexes ◽

X Ray ◽

X Ray Crystallography ◽

New Compounds

The hexacarbonyl compounds of chromium, molybdenum and tungsten react with the highly nucleophilic agent Li NiPr2 and in a subsequent alkylation with (Et3O)BF4 to give the carbene complexes (CO)5M[C(N′Pr2)OEt] (1, 3, 4). In case of W(CO)6 and Mo(CO)6 the novel biscarbene complexes cis(CO)4M[C(NiPr2)OEt]2 (2, 5) are additionally obtained. Reaction conditions, properties and spectroscopic data of the new compounds are reported. The molecular structure of cis(CO)4W[C(NiPr2)OEt]2 (4) was determined by X-ray crystallography

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Functionalized 1,3-Thiazolidin-4-Ones from 2-Oxo-Acenaphthoquinylidene- and [2.2]Paracyclophanylidene-Thiosemicarbazones

Molecules ◽

10.3390/molecules24173069 ◽

2019 ◽

Vol 24 (17) ◽

pp. 3069 ◽

Cited By ~ 3

Author(s):

Ashraf A. Aly ◽

Nasr K. Mohamed ◽

Alaa A. Hassan ◽

Kamal M. El-Shaieb ◽

Maysa M. Makhlouf ◽

...

Keyword(s):

Mass Spectrometry ◽

Elemental Analysis ◽

13C Nmr ◽

Spectroscopic Data ◽

Complex Structure ◽

2D Nmr ◽

Efficient Tool ◽

X Ray ◽

Dialkyl Acetylenedicarboxylates ◽

Allyl Derivative

The reactions of dialkyl acetylenedicarboxylates with various 2-oxo-acenaphthoquinylidene- and 4-acetyl[2.2]paracyclophanylidene-thiosemicarbazones were investigated. Using simple experimental procedures, 1,3-Thiazolidin-4-ones derived from acenaphthequinone or [2.2]paracyclophane were obtained as major products in good yields. In the case of allyl derivative of acenaphthoquinylidene-thiosemicarbazones, a complex structure of tetramethyl 5-(2-(((Z,E)-N-allyl-N′-(2-oxoacenaphthylen-1(2H)-ylidene)carbamohydrazonoyl)thio)-1,2,3-tris-(methoxycarbonyl)-cyclopropyl)-4-methoxy-7-oxabicyclo[2.2.1]hepta-2,5-diene-1,2,3,6-tetracarboxylate was formed. Single crystal X-ray analysis was used as an efficient tool to confirm the structure of the synthesized compounds as well as different spectroscopic data (1H-NMR, 13C-NMR, 2D-NMR, mass spectrometry and elemental analysis). The mechanism of the obtained products was discussed.

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Analysis of structural MtrC models based on homology with the crystal structure of MtrF

Biochemical Society Transactions ◽

10.1042/bst20120132 ◽

2012 ◽

Vol 40 (6) ◽

pp. 1181-1185 ◽

Cited By ~ 18

Author(s):

Marcus J. Edwards ◽

James K. Fredrickson ◽

John M. Zachara ◽

David J. Richardson ◽

Thomas A. Clarke

Keyword(s):

Crystal Structure ◽

Outer Membrane ◽

Domain Structure ◽

Spectroscopic Data ◽

Sequence Similarity ◽

Shewanella Oneidensis ◽

Significant Sequence Similarity ◽

X Ray ◽

X Ray Crystallography ◽

Homology Models

The outer-membrane decahaem cytochrome MtrC is part of the transmembrane MtrCAB complex required for mineral respiration by Shewanella oneidensis. MtrC has significant sequence similarity to the paralogous decahaem cytochrome MtrF, which has been structurally solved through X-ray crystallography. This now allows for homology-based models of MtrC to be generated. The structure of these MtrC homology models contain ten bis-histidine-co-ordinated c-type haems arranged in a staggered cross through a four-domain structure. This model is consistent with current spectroscopic data and shows that the areas around haem 5 and haem 10, at the termini of an octahaem chain, are likely to have functions similar to those of the corresponding haems in MtrF. The electrostatic surfaces around haem 7, close to the β-barrels, are different in MtrF and MtrC, indicating that these haems may have different potentials and interact with substrates differently.

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