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A Novel Azaphilone Muyophilone A From the Endophytic Fungus 0307-2

Overview
Journal Front Chem
Specialty Chemistry
Date 2021 Sep 7
PMID 34490216
Citations 1
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Abstract

Two known azaphilone derivatives, 4,6-dimethylcurvulinic acid () and austdiol (), and their novel heterotrimer, muyophilone A (), were isolated and identified from an endophytic fungus, 0307-2. Their structures and stereochemistry were established by extensive spectroscopic analyses including HRMS, NMR spectroscopy, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopic methods, as well as single crystal X-ray diffraction. In the structure of , two compound -derived azaphilone units were connected through an unprecedented five-membered carbon bridge which was proposed to be originated from compound . Compound represents the first example of azaphilone heterotrimers.

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References
1.
Pracht P, Grimme S . Calculation of absolute molecular entropies and heat capacities made simple. Chem Sci. 2021; 12(19):6551-6568. PMC: 8139639. DOI: 10.1039/d1sc00621e. View

2.
Yin G, Wu Y, Yang M, Li T, Wang X, Zhou M . Citrifurans A-D, Four Dimeric Aromatic Polyketides with New Carbon Skeletons from the Fungus Aspergillus sp. Org Lett. 2017; 19(15):4058-4061. DOI: 10.1021/acs.orglett.7b01823. View

3.
Cao F, Meng Z, Mu X, Yue Y, Zhu H . Absolute Configuration of Bioactive Azaphilones from the Marine-Derived Fungus Pleosporales sp. CF09-1. J Nat Prod. 2019; 82(2):386-392. DOI: 10.1021/acs.jnatprod.8b01030. View

4.
Akihisa T, Tokuda H, Yasukawa K, Ukiya M, Kiyota A, Sakamoto N . Azaphilones, furanoisophthalides, and amino acids from the extracts of Monascus pilosus-fermented rice (red-mold rice) and their chemopreventive effects. J Agric Food Chem. 2005; 53(3):562-5. DOI: 10.1021/jf040199p. View

5.
Lo Presti L, Soave R, Destro R . The fungal metabolite austdiol. Acta Crystallogr C. 2003; 59(Pt 4):O199-201. DOI: 10.1107/s0108270103005031. View