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Daldinone A Sale

目录号 : GC47169

A fungal metabolite

Daldinone A Chemical Structure

Cas No.:479669-74-4

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1 mg
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产品描述

Daldinone A is a fungal metabolite originally isolated from D. concentrica.1

1.Quang, D.N., Hashimoto, T., Tanaka, M., et al.Chemical constituents of the ascomycete Daldinia concentricaJ. Nat. Prod.65(12)1869-1874(2002)

Chemical Properties

Cas No. 479669-74-4 SDF
Canonical SMILES OC1=C(C2=CC=C1)C(C[C@]3([H])[C@@]2(O)C4=CC=C(O)C5=C4[C@]3([H])CCC5=O)=O
分子式 C20H16O5 分子量 336.3
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 2.9735 mL 14.8677 mL 29.7354 mL
5 mM 0.5947 mL 2.9735 mL 5.9471 mL
10 mM 0.2974 mL 1.4868 mL 2.9735 mL
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Research Update

TfOH catalysed domino-double annulation of arenes with propargylic alcohols: a unified approach to indene polycyclic systems

Chem Commun (Camb) 2021 Nov 30;57(95):12796-12799.PMID:34782905DOI:10.1039/d1cc05253e.

The design and development of a TfOH catalysed domino strategy for the double annulation of arenes with propargylic alcohols for the rapid generation of indene based polycyclic systems is reported. The dehydration, intramolecular 6-endo-dig hydroarylation, and cationic cyclization were consecutively promoted by TfOH. The key features of this strategy are the formation of two C-C bonds, unified access to indene polycyclic systems, excellent yields (up to 95%), high atom economy (>90%), an operationally simple procedure, and water being the only byproduct. By extending this strategy, a two-step synthesis of the pentacyclic systems of hypoxylonol A (43% overall yield from α-tetralone), Daldinone A (63% overall yield from β-tetralone) and spiro-tetracyclic framework of incarviatone A has also been achieved.

Cohaerins A and B, azaphilones from the fungus Hypoxylon cohaerens, and comparison of HPLC-based metabolite profiles in Hypoxylon sect. Annulata

Phytochemistry 2005 Apr;66(7):797-809.PMID:15797606DOI:10.1016/j.phytochem.2005.02.006.

Azaphilones, named cohaerins A and B were isolated from stromata of the xylariaceous ascomycete Hypoxylon cohaerens. Their absolute structures were determined by spectroscopic methods (2D NMR, MS, IR, UV CD), and subsequently confirmed by acetylation. Stromatal metabolite profiles of several taxa of Hypoxylon sect. Annulata were also generated using analytical HPLC with diode array and MS detection. The cohaerins were neither found in other Hypoxylon spp., nor in other Xylariaceae. However, they were present even in holotype material of H. cohaerens, collected over 200 years ago. The binaphthalene BNT was also omnipresent in sect Annulata, and its derivatives, the benzo[j]fluoranthenes Daldinone A and truncatone, as well as presumably related compounds. These fungi were found devoid of other types of azaphilone pigments of the Xylariaceae, such as mitorubrins and daldinins, the latter of which are widespread in certain groups of Hypoxylon sect. Hypoxylon. Hence, chemotaxonomic data largely support the current generic concept. The original source of truncatone was identified as Hypoxylon annulatum.

Antimicrobial metabolites produced by endophytic fungi associated with the leaves of Vochysia divergens

Nat Prod Res 2023 May 8;1-8.PMID:37154616DOI:10.1080/14786419.2023.2208723.

Investigation of the endophytic fungi Nigrospora sphaerica, Nigrospora oryzae, and Pseudofusicoccum stromaticum MeOH fractions isolated from the leaves of Vochysia divergens, a medicinal species from the Brazilian Pantanal, led to the identification of five compounds, namely a new compound (1E,8Z)-10,11-dihydroxy-5,5,8-trimethyl-4-oxocycloundeca-1,8-diene-1-carbaldehyde (1) and four known compounds: 5-methylmellein (2), sclerone (3), Daldinone A (4), and lasiodiplodin (5). All compounds were identified using spectroscopic methods, and 1 was corroborated with mass spectrometry, while the known compounds were compared with data in the literature. The relative configuration of compound 1 was determined based on theoretical conformational studies as well as the J experimental values between the hydroxymethyne hydrogens. The antimicrobial activity of the compounds was evaluated. Promising results were obtained for compounds 2, 4, and 5 since they inhibited the bacterium Pseudomonas aeruginosa, an opportunistic pathogen, suggesting the potential of these microorganisms as a source of new antibacterial agents.

Chemical constituents of the ascomycete Daldinia concentrica

J Nat Prod 2002 Dec;65(12):1869-74.PMID:12502330DOI:10.1021/np020301h.

Four compounds, Daldinone A (1), daldinone B (2), daldiniapyrone (4-methoxy-5-carbomethoxy-6-pentyl-2H-pyran-2-one, 3), and daldinialanone (22R-hydroxylanosta-7,9(11),24-trien-3-one, 4), were isolated from an ethyl acetate extract of fruit bodies of Daldinia concentrica collected in Europe. In addition, 11 known compounds, 4:5:4':5'-tetrahydroxy-1:1'-binaphthyl (5), 3,4,5-trihydroxy-1-tetralone (6), (+)-orthosporin (7), curuilignan D (8), (22E)-cholesta-4,6,8(14),22-tetraen-3-one (9), 3beta,22-dihydroxylanosta-7,9(11),24-triene (10), concentricol (11), concentricol B (12), concentricol C (13), concentricol D (14), and phenochalasin B (15), were obtained. The structures of the new compounds were elucidated by 2D NMR, MS, IR, and UV spectra and by X-ray crystallographic analysis. The absolute configurations of 1 and 4 were determined by CD spectroscopy and the modified Mosher's method, respectively. The chemotaxonomic relevance of the compounds obtained in this investigation is discussed.