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目录号 : GC47046

A fungal metabolite with immunosuppressive and antitrypanosomal activities

Carviolin Chemical Structure

Cas No.:478-35-3

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1 mg
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产品描述

Carviolin is an anthraquinone fungal metabolite that has been found in Z. longicaudata with immunosuppressive and antitrypanosomal activities.1,2 It inhibits LPS- or concanavalin A-induced proliferation of mouse splenocytes (IC50s = 4 and 4.5 µg/ml, respectively).1 Carviolin is active against T. b. brucei (MIC = 41.66 µM).2

1.Fujimoto, H., Nakamura, E., Okuyama, E., et al.Six immunosuppressive features from an ascomycete, Zopfiella longicaudata, found in a screening study monitored by immunomodulatory activityChem. Pharm. Bull. (Tokyo)52(8)1005-1008(2004) 2.Aly, A.H., Debbab, A., Clements, C.M., et al.NF kappa B inhibitors and antitrypanosomal metabolites from endophytic fungus Penicillium sp. isolated from Limonium tubiflorumBioorg. Med. Chem.19(1)414-421(2011)

Chemical Properties

Cas No. 478-35-3 SDF
Canonical SMILES O=C1C2=C(C=C(CO)C=C2OC)C(C3=CC(O)=CC(O)=C31)=O
分子式 C16H12O6 分子量 300.3
溶解度 Dichloromethane: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 3.33 mL 16.65 mL 33.3 mL
5 mM 0.666 mL 3.33 mL 6.66 mL
10 mM 0.333 mL 1.665 mL 3.33 mL
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Research Update

Antifeedant and Antifungal Activities of Metabolites Isolated from the Coculture of Endophytic Fungus Aspergillus tubingensis S1120 with Red Ginseng

Chem Biodivers 2022 Jan;19(1):e202100608.PMID:34786852DOI:10.1002/cbdv.202100608.

A new globoscinic acid derivative, aspertubin A (1) along with four known compounds, were obtained from the co-culture of Aspergillus tubingensis S1120 with red ginseng. The chemical structures of compounds were characterized by using spectroscopic methods, the calculated and experimental electronic circular dichroism. Panaxytriol (2) from red ginseng, and asperic acid (4) showed significant antifeedant effect with the antifeedant rates of 75 % and 80 % at the concentrations of 50 μg/cm2 . Monomeric Carviolin (3) and asperazine (5) displayed weak attractant activity on silkworm. All compounds were assayed for antifungal activities against phytopathogens A. tubingensis, Nigrospora oryzae and Phoma herbarum and the results indicated that autotoxic aspertubin A (1) and panaxytriol (2) possessed selective inhibition against A. tubingensis with MIC values at 8 μg/mL. The co-culture extract showed higher antifeedant and antifungal activities against P. herbarum than those of monoculture of A. tubingensis in ordinary medium. So the medicinal plant and endophyte showed synergistic effect on the plant disease resistance by active compounds from the coculture of A. tubingensis S1120 and red ginseng.

Ultra-Large-Scale Screening of Natural Compounds and Free Energy Calculations Revealed Potential Inhibitors for the Receptor-Binding Domain (RBD) of SARS-CoV-2

Molecules 2022 Oct 28;27(21):7317.PMID:36364143DOI:10.3390/molecules27217317.

The emergence of immune-evading variants of SARS-CoV-2 further aggravated the ongoing pandemic. Despite the deployments of various vaccines, the acquired mutations are capable of escaping both natural and vaccine-induced immune responses. Therefore, further investigation is needed to design a decisive pharmacological treatment that could efficiently block the entry of this virus into cells. Hence, the current study used structure-based methods to target the RBD of the recombinant variant (Deltacron) of SARS-CoV-2, which was used as a model variant. From the virtual drug screenings of various databases, a total of four hits were identified as potential lead molecules. Key residues were blocked by these molecules with favorable structural dynamic features. The binding free energies further validated the potentials of these molecules. The TBE for MNP was calculated to be -32.86 ± 0.10 kcal/mol, for SANC00222 the TBE was -23.41 ± 0.15 kcal/mol, for Liriodenine the TBE was -34.29 ± 0.07 kcal/mol, while for Carviolin the TBE was calculated to be -27.67 ± 0.12 kcal/mol. Moreover, each complex demonstrated distinct internal motion and a free energy profile, indicating a different strategy for the interaction with and inhibition of the RBD. In conclusion, the current study demands further in vivo and in vitro validation for the possible usage of these compounds as potential drugs against SARS-CoV-2 and its variants.

Penicillium dravuni, a new marine-derived species from an alga in Fiji

Mycologia 2005 Mar-Apr;97(2):444-53.PMID:16396352DOI:10.3852/mycologia.97.2.444.

Penicillium dravuni is a new monoverticillate, sclerotium-forming species that was isolated from the alga Dictyosphaeria versluyii collected in Dravuni, Fiji. This species morphologically is similar to P. turbatum in the P. turbatum subseries of the P. thomii series of the Monoverticillata. The nuclear ribosomal internal transcribed spacer region exhibited 97% sequence similarity to known Penicillium spp. in the GenBank database. Phylogenetic analyses revealed that P. dravuni is related most closely to Eupenicillium brefeldianum, E. levitum, E. reticulosporum, E. javanicum, E. ehrlichii and PF simplicissimum. However this new species shares only a distant ancestor with this clade because it branches by itself early in the lineage. P. dravuni also is known to produce the secondary metabolites dictyosphaeric acids A and B and Carviolin.

Dictyosphaeric acids A and B: new decalactones from an undescribed Penicillium sp. obtained from the alga Dictyosphaeria versluyii

J Nat Prod 2004 Aug;67(8):1396-9.PMID:15332862DOI:10.1021/np049973t.

Fungal isolate F01V25 was obtained from the alga Dictyosphaeria versluyii collected near Dravuni, Fiji, in 2001 and represented a previously undescribed Penicillium sp. Fermentation of isolate F01V25 resulted in the production of two new polyketides, dictyosphaeric acids A and B, along with the known anthraquinone Carviolin. The relative stereochemistry of dictyosphaeric acids A and B was determined using the J-based configuration analysis method in conjunction with ROE and NOE correlations.

Six immunosuppressive features from an ascomycete, Zopfiella longicaudata, found in a screening study monitored by immunomodulatory activity

Chem Pharm Bull (Tokyo) 2004 Aug;52(8):1005-8.PMID:15305003DOI:10.1248/cpb.52.1005.

In a screening study on immunomodulatory fungal metabolites, three known anthraquinones, Carviolin (roseo-purpurin) (1), 1-O-methylemodin (2), omega-hydroxyemodin (citreorosein) (4), and a new anthraquinone, omega-acetylcarviolin (3), together with a known steroid, ergosta-4,6,8(14),22-tetraen-3-one (5) and a new steroid, 25-hydroxyergosta-4,6,8(14),22-tetraen-3-one (6) were isolated from an Ascomycete, Zopfiella longicaudata, and found to have moderate immunosuppressive activities. The structure-activity relationships of these metabolites are discussed.