MetaboLights
A trihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1, 4 and 5, a methoxy group at position 7 and a methyl group at position 2. It has been isolated from Chaetomium globosum and other fungal species.
Identification
1,4,5-trihydroxy-7-methoxy-2-methylanthracene-9,10-dione
Erythroglaucine
Europe PubMed Central results
Transcriptome analysis reveals the pheromone synthesis mechanism and mating response in Monochamus saltuarius (Coleoptera, Cerambycidae).
Author: Niu Y, Chi Y, Xu Y, Zhang S, Shi F, Zhao Y, Li M, Zong S, Tao J.
Abstract: The pinewood nematode Bursaphelenchus xylophilus (Steiner and Buhrer 1934) causes pine wilt disease, which severely affects the biodiversity and economy of Eurasian coniferous forests. Monochamus saltuarius (Coleoptera, Cerambycidae) was first identified as nematode vectors in Liaoning Province, China, in 2017. M. saltuarius has high mating efficiency and reproductive capabilities, pheromones are crucial in these processes. However, the mechanisms of pheromone synthesis in M. saltuarius are unclear. This study performed morphometric and transcriptomic analyses of the internal reproductive systems of males and females at different developmental stages and analyzed mate selection behavior. We found a significant difference in the morphology of internal reproductive systems between sexually immature and mature insects. A total of 58 and 64 pheromone biosynthesis genes were identified in females and males, respectively. The expression of the analyzed genes differed between males and females in the initial and subsequent synthesis processes. Interference experiment indicated that knocking down SDR1 gene in male M. saltuarius reduces the content of pheromones. Behavioral analyses found that males preferred virgin females. This study identified key pheromone genes and synthesis pathway that could serve as potential targets for disrupting mating in M. saltuarius through the development of novel biological agents using genetic engineering techniques.
Toxicity and mutagenicity of anthraquinones from Aspergillus chevalieri.
Author: Bachmann M, Blaser P, Lüthy J, Schlatter C.
Abstract: More than 100 strains of the Aspergillus glaucus group were cultivated on synthetic media for 11 days at 28 degrees C. Organic extracts of fungal material were screened by thin-layer chromatography (TLC) for the mycotoxins aflatoxins B1,2 and G1,2, sterigmatocystin, ochratoxin A, gliotoxin, patulin, and xanthocillin X. None of these toxins were produced in detectable amounts under experimental conditions. Nevertheless, organic extracts exhibited high toxicity after intraperitoneal (i.p.) administration in mice. Aspergillus chevalieri strain ZT 8268 was selected for further investigation of its toxic metabolites. The main toxic action was attributed to the four anthraquinone derivatives, physicion, physcionanthrone B, physciondianthrone, and erythroglaucin, which were isolated and identified. No toxic effects were found after oral administration. Using the Salmonella/mammalian microsome test, mutagenic activity (frame-shift) was detected in strain TA 1537 in the presence of S-9 liver microsome preparation.
4-benzyl-3-phenyl-5H-furan-2-one, a vasodilator isolated from Malbranchea filamentosa IFM 41300.
Author: Hosoe T, Iizuka T, Komai S, Wakana D, Itabashi T, Nozawa K, Fukushima K, Kawai K.
Abstract: Screening of Malbranchea filamentosa IFM 41300 for bioactive compounds led to the identification of 4-benzyl-3-phenyl-5H-furan-2-one (1) as a vasodilator and erythroglaucin (2). The structure of 1 was established on the basis of spectroscopic and chemical investigations. Compound 1 inhibited Ca2+-induced vasocintraction in aortic rings pretreated with high K+ (60mM) or norepinephrine. Finally, compound 1 did not exhibit activity against human pathogenic microorganisms.
Studies in the biochemistry of micro-organisms: The molecular constitutions of catenarin and erythroglaucin, metabolic products respectively of Helminthosporium catenarium Drechsler and of species in the Aspergillus glaucus series.
Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata.
Author: Wang S, Li XM, Teuscher F, Li DL, Diesel A, Ebel R, Proksch P, Wang BG.
Abstract: Cultivation of the endophytic fungus Chaetomium globosum, which was isolated from the inner tissue of the marine red alga Polysiphonia urceolata, resulted in the isolation of chaetopyranin (1), a new benzaldehyde secondary metabolite. Ten known compounds were also isolated, including two benzaldehyde congeners, 2-(2',3-epoxy-1',3'-heptadienyl)-6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde (2) and isotetrahydroauroglaucin (3), two anthraquinone derivatives, erythroglaucin (4) and parietin (5), five asperentin derivatives including asperentin (6, also known as cladosporin), 5'-hydroxy-asperentin-8-methylether (7), asperentin-8-methyl ether (8), 4'-hydroxyasperentin (9), and 5'-hydroxyasperentin (10), and the prenylated diketopiperazine congener neoechinulin A (11). The structures of these compounds were determined on the basis of their spectroscopic data analysis (1H, 13C, 1H-1H COSY, HMQC, and HMBC NMR, as well as low- and high-resolution mass experiments). To our knowledge, compound 1 represents the first example of a 2H-benzopyran derivative of marine algal-derived fungi as well as of the fungal genus Chaetomium. Each isolate was tested for its DPPH (1,1-diphenyl-2-picrylhydrazyl) radical-scavenging property. Compounds 1-4 were found to have moderate activity. Chaetopyranin (1) also exhibited moderate to weak cytotoxic activity toward several tumor cell lines.
DOI: 10.1021/np060248n
The improvement of quality of life in patients treated with bariatric surgery in Korea.
Author: Oh SH, Song HJ, Kwon JW, Park DJ, Lee YJ, Chun H, Kim S, Shim KW.
Abstract: <h4>Purpose</h4>Bariatric surgery is considered an efficient treatment for severe obesity, but postoperative complications and psychosocial problems may impact quality of life (QoL). Although QoL is an important aspect of bariatric surgery, few studies have evaluated the changes in QoL. We examined whether severely obese patients who had undergone bariatric surgery had better QoL compared with severely obese adults who had not undergone bariatric surgery in Korea.<h4>Methods</h4>Data were obtained from 78 participants in two groups; bariatric surgery group (n = 53) and nonsurgery group (n = 25). EuroQoL-5D (EQ-5D), the impact of weight on quality of life-lite (IWQoL-lite) and the obesity-related psychosocial problem scale (OP-scale) were used to assess the improvement of QoL.<h4>Results</h4>A total of 78 patients completed the QoL forms as part of their surgical consultation. In the EQ-5D, the changes of EQ-5D 3 level and EQ-5D visual analogue scale in the surgery group was 0.174 and 24.6 versus 0.017 and 17.8 in the nonsurgery group (P = 0.197 and P = 0.179). The changes of IWQoL-lite and OP-scale were significantly improved after bariatric surgery. In the IWQoL-lite, the mean changes in the surgery group was 33.4 versus 14.3 points in the nonsurgery group (P = 0.000). In the OP-scale, the mean changes in the surgery group patients scored 39.3 versus 9.0 points in the nonsurgery group (P = 0.000).<h4>Conclusion</h4>We demonstrated significant improvement of QoL observed after bariatric surgery compared to nonsurgical procedure. The results of this comparative study favor bariatric surgery for the treatment of severe obesity.
A new <sup>68</sup>Ga-labeled somatostatin analog containing two iodo-amino acids for dual somatostatin receptor subtype 2 and 5 targeting.
Author: Mansi R, Abid K, Nicolas GP, Del Pozzo L, Grouzmann E, Fani M.
Abstract: <h4>Background</h4>Somatostatin receptor (SST) targeting, specifically of the subtype 2 (SST2), with radiolabeled somatostatin analogs, is established for imaging and treatment of neuroendocrine tumors. Owing to the concomitant and heterogeneous expression of several subtypes on the same tumor, analogs targeting more subtypes than SST2 potentially target a broader spectrum of tumors and/or increase the uptake of a given tumor. The analog ST8950 ((4-amino-3-iodo)-D-Phe-c[Cys-(3-iodo)-Tyr-D-Trp-Lys-Val-Cys]-Thr-NH<sub>2</sub>), bearing 2 iodo-amino acids, exhibits sub-nanomolar affinity to SST2 and SST5. We report herein the development and preclinical evaluation of DOTA-ST8950 labeled with <sup>68</sup>Ga, for imaging SST2- and SST5-expressing tumors. Comparative in vitro and in vivo studies were performed with the de-iodinated DOTA-ST8951 ((4-amino)-D-Phe-c[Cys-Tyr-D-Trp-Lys-Val-Cys]-Thr-NH<sub>2</sub>) and with the reference compounds DOTA-TATE (SST2 selective) and DOTA-NOC (for SST2 and SST5).<h4>Results</h4>Compared with <sup>nat</sup>Ga-DOTA-NOC, <sup>nat</sup>Ga-DOTA-ST8950 exhibited higher affinity to SST2 and SST5 (IC<sub>50</sub> (95%CI), nM = 0.32 (0.20-0.50) and 1.9 (1.1-3.1) vs 0.70 (0.50-0.96) and 3.4 (1.8-6.2), respectively), while <sup>nat</sup>Ga-DOTA-ST8951 lost affinity for both subtypes. <sup>nat</sup>Ga-DOTA-ST8950 had the same potency for inducing SST2-mediated cAMP accumulation as <sup>nat</sup>Ga-DOTA-TATE and slightly better than <sup>nat</sup>Ga-DOTA-NOC (EC<sub>50</sub>, nM = 0.46 (0.23-0.92) vs 0.47 (0.15-1.5) vs 0.59 (0.18-1.9), respectively). [<sup>67</sup>Ga]Ga-DOTA-ST8950 had a similar internalization rate as [<sup>67</sup>Ga]Ga-DOTA-NOC in SST2-expressing cells (12.4 ± 1.6% vs 16.6 ± 2.2%, at 4 h, p = 0.0586). In vivo, [<sup>68</sup>Ga]Ga-DOTA-ST8950 showed high and specific accumulation in SST2- and SST5-expressing tumors, comparable with [<sup>68</sup>Ga]Ga-DOTA-NOC (26 ± 8 vs 30 ± 8 %IA/g, p = 0.4630 for SST2 and 15 ± 6 vs 12 ± 5 %IA/g, p = 0.3282, for SST5, 1 h p.i.) and accumulation in the SST-positive tissues, the kidneys and the liver. PET/CT images of [<sup>68</sup>Ga]Ga-DOTA-ST8950, performed in a dual HEK-SST2 and HEK-SST5 tumor xenografted model, clearly visualized both tumors and illustrated high tumor-to-background contrast.<h4>Conclusions</h4>[<sup>68</sup>Ga]Ga-DOTA-ST8950 reveals its potential for PET imaging SST2- and SST5-expressing tumors. It compares favorably with the clinically used [<sup>68</sup>Ga]Ga-DOTA-NOC in terms of tumor uptake; however, its uptake in the liver remains a challenge for clinical translation. In addition, this study reveals the essential role of the iodo-substitutions in positions 1 and 3 of [<sup>68</sup>Ga]Ga-DOTA-ST8950 for maintaining affinity to SST2 and SST5, as the de-iodinated [<sup>68</sup>Ga]Ga-DOTA-ST8951 lost affinity for both receptor subtypes.