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1.
Front Chem ; 10: 911543, 2022.
Article in English | MEDLINE | ID: mdl-35815214

ABSTRACT

One novel diterpenoid lactone named caesalpinbondin A (1) that possesses an unprecedented tetracyclic ring system in which a 6/6/5-fused tricyclic ring and a 4,5-dimethyldihydrofuran-2(3H)-one were connected by a C-C single bond comprising a 5-(naphtho [2,3-b]furan-7-yl)dihydrofuran-2(3H)-one moiety was isolated from the seeds of Caesalpinia bonduc. Its chemical structure was established by extensive spectroscopic methods, and its absolute configuration was further determined by single-crystal X-ray diffraction analysis and electronic circular dichroism calculation. The biological evaluation suggested that compound 1 demonstrated potent anti-Alzheimer's disease (AD) bioactivity, which could delay paralysis of transgenic AD Caenorhabditis elegans. A possible biogenetic pathway of 1 was also proposed.

2.
Parasitol Res ; 119(7): 2359-2362, 2020 Jul.
Article in English | MEDLINE | ID: mdl-32500368

ABSTRACT

Several Cryptosporidium species that infect reptiles, especially squamates, are well described, but there is limited data about Cryptosporidium species infecting crocodilians. In this study, we assess the occurrence of intestinal parasites using traditional microscopic examination and describe the prevalence and Cryptosporidium species in the captive-bred Chinese alligators (Alligator sinensis) in eastern China using molecular methods. The results of microscopic examination showed that no intestinal parasites were detected among the 491 fecal samples examined from the Chinese alligators. The overall prevalence for Cryptosporidium was 0.41% (2/491) by PCR detection using the SSU rRNA locus. Sequence and phylogenetic analysis of the SSU rRNA, COWP, and actin genes revealed the presence of Cryptosporidium testudinis, which has been isolated primarily from chelonians. This is the first detection of the specific DNA of C. testudinis in the feces of the Chinese alligator. This study expands our knowledge of the Cryptosporidium species involved in crocodiles, and more extensive studies are necessary to confirm the validity of C. testudinis in crocodiles.


Subject(s)
Alligators and Crocodiles/parasitology , Cryptosporidiosis/parasitology , Cryptosporidium/isolation & purification , Animals , China/epidemiology , Cryptosporidiosis/epidemiology , Cryptosporidium/classification , Cryptosporidium/genetics , DNA, Protozoan/genetics , DNA, Ribosomal/genetics , Feces/parasitology , Genes, Protozoan/genetics , Phylogeny
3.
Food Microbiol ; 82: 482-488, 2019 Sep.
Article in English | MEDLINE | ID: mdl-31027809

ABSTRACT

Shiga toxin-producing Escherichia coli (STEC) is one of the most common causal agents of foodborne illness linked to fresh leafy vegetables. Here, we investigated the impact of spinach-associated microorganisms on proliferation and biofilm formation of STEC O157:H7 on stainless steel surfaces at temperatures related to produce production and postharvest processing environments. Although a proliferation of inoculated pathogen cells in spinach leaf wash water was detected at all temperatures examined, the impact of spinach-associated microorganisms on the proliferation of E. coli O157:H7 was observed at 10 °C and 26 °C, but not at 4 °C. The inhibition of E. coli O157:H7 growth by spinach-associated microorganisms indicated a competition between the pathogen and spinach indigenous microflora. A significant decrease of the pathogen population in mixed biofilms was observed only at 26 °C for curli-deficient strain MQC43, but not for curli-expressing strain MQC57. Deletion of curli genes in a curli-expressing strain resulted in a phenotype similar to that of MQC43 in mixed biofilms; however, this deficiency was rescued when curli biogenesis was restored in the curli-deletion mutant strain. Our data support that curli confer E. coli O157:H7 a competitive trait in mixed biofilms, presumably through the interaction between STEC and the biofilm-proficient microorganisms associated with spinach leaves.


Subject(s)
Biofilms , Escherichia coli Proteins/physiology , Food Microbiology , Shiga-Toxigenic Escherichia coli/physiology , Spinacia oleracea/microbiology , Bacterial Adhesion/genetics , Biofilms/growth & development , Colony Count, Microbial , Escherichia coli O157/genetics , Escherichia coli O157/growth & development , Escherichia coli O157/physiology , Escherichia coli Proteins/genetics , Genetic Complementation Test , Microbial Interactions , Microbiota/physiology , Mutation , Shiga-Toxigenic Escherichia coli/genetics , Shiga-Toxigenic Escherichia coli/growth & development , Stainless Steel , Temperature
4.
Org Biomol Chem ; 16(10): 1745-1750, 2018 03 07.
Article in English | MEDLINE | ID: mdl-29460936

ABSTRACT

A novel C16 tetranorditerpenoid, norcrassin A (1), and an unusual dimeric labdane-type diterpenoid, bicrotonol A (2), were isolated from the roots of Croton crassifolius. Norcrassin A (1) featured a new carbon skeleton with an unprecedented 5/5/5/6 tetracyclic system. Bicrotonol A (2) possessed an unusual tetrahydroxypyran ring linkage connecting two labdane diterpenoid monomers. The structures of all compounds, including the absolute configuration, were elucidated by the interpretation of their NMR spectroscopic data, high resolution mass spectrometry, and single-crystal X-ray diffraction. A plausible biosynthetic pathway of 1 is proposed. The anti-Alzheimer's Disease (AD) activities of 1 and 2 are also evaluated using the AD pathological model.


Subject(s)
Alzheimer Disease/drug therapy , Croton/chemistry , Diterpenes/chemistry , Diterpenes/therapeutic use , Plant Roots/chemistry , Animals , Animals, Genetically Modified , Caenorhabditis elegans/genetics , Crystallography, X-Ray , Disease Models, Animal , Diterpenes/isolation & purification , Humans , Magnetic Resonance Spectroscopy , Models, Molecular
5.
Org Lett ; 18(12): 2844-7, 2016 06 17.
Article in English | MEDLINE | ID: mdl-27230557

ABSTRACT

Euphorikanin A (1), an unprecedented diterpenoid lactone which possesses a novel 5/6/7/3-fused tetracyclic ring skeleton, was isolated from the roots of Euphorbia kansui. The chemical structure and absolute stereochemistry were elucidated on the basis of extensive spectroscopic methods and single-crystal X-ray diffraction analysis. Compound 1 exhibited moderate cytotoxicity against two human tumor cell lines HeLa and NCI-446. A proposed biosynthetic pathway of compound 1 is also described.

6.
J Asian Nat Prod Res ; 17(4): 415-9, 2015.
Article in English | MEDLINE | ID: mdl-25363682

ABSTRACT

A new eremophilane norsesquiterpenoid (1), together with a known eremophilane sesquiterpenoid (2), was isolated from the leaves of Ligularia virgaurea. The structure of 1 was elucidated by a combination of spectroscopic analysis (IR, 1D NMR, 2D NMR, and HR-ESI-MS), and its absolute configuration was determined by a single-crystal X-ray diffraction experiment (with copper radiation). The known compound 2 was identified by comparison of its physical and spectral data with those reported in the literature. Compound 1 was assayed for its cytotoxic activities against human cervical carcinoma cell (HeLa) and human small cell lung cancer cell (NCI-446) lines.


Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Asteraceae/chemistry , Sesquiterpenes/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Crystallography, X-Ray , Drug Screening Assays, Antitumor , HeLa Cells , Humans , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology
7.
Nat Prod Commun ; 10(11): 1917-8, 2015 Nov.
Article in English | MEDLINE | ID: mdl-26749826

ABSTRACT

A chemical investigation of Croton crassifolius afforded a novel norclerodane diterpenoid (1) with an unprecedented six-membered oxygen ring between C-1 and C-12, together with three known compounds. The structure of the new compound was elucidated based on spectroscopic (IR, 1D, and 2D NMR) and HR-ESI-MS techniques. This report describes the first example of a natural norclerodane with a 4H-chromene ring system.


Subject(s)
Croton/chemistry , Diterpenes/chemistry , Plant Extracts/chemistry , Diterpenes/isolation & purification , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Extracts/isolation & purification , Plant Roots/chemistry , Spectrometry, Mass, Electrospray Ionization
8.
Article in English | MEDLINE | ID: mdl-24046650

ABSTRACT

The title compound, C17H20O5, an eremophilane sesquiternoid, was isolated from the roots of Ligularia lapathifolia. The mol-ecule contains four fused rings of which the six-membered ring A adopts a half-chair conformation, the six-membered ring B adopts a chair conformation, the five-membered ring C is almost planar (r.m.s. deviation = 0.015 Å) and the five-membered ring D adopts an envelope conformation with the quaternary C atom as the flap. The methyl and the eth-oxy groups adopt a syn conformation and the A/B ring junction is cis-fused. No directional inter-molecular inter-actions could be identified in the crystal.

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