New α-pyrone and phthalide from the Xylariaceae fungus

Zou, Jian; Li, Jun; Zhao, Qing; Wang, Gao-Qian; Zhao, Huan; Chen, Guodong; Sun, Xiang; Guo, Liangdong; Gao, Hao

doi:10.1080/10286020.2015.1054816

Cited by 7 publications

(1 citation statement)

References 25 publications

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“…Among our recent discoveries [11,12,13,14,15,16,17,18,19,20,21], we recently reported that a strain of Streptomyces sp. HK-2006-1 produced both aldgamycins and chalcomycins, which are 16-membered macrolides [11,21].…”

Section: Introductionmentioning

confidence: 99%

Chalcomycins from Marine-Derived Streptomyces sp. and Their Antimicrobial Activities

et al. 2017

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Dihydrochalcomycin (1) and chalcomycin (2), two known chalcomycins, and chalcomycin E (3), a new compound, were isolated from marine-derived Streptomyces sp. HK-2006-1. Their structures were elucidated by detailed spectroscopic and X-ray crystallographic analysis. The antimicrobial activities against Staphylococcus aureus, Escherichia coli, Candida albicans, and Aspergillus niger of 1-3 were evaluated. Compounds 1-2 exhibited activities against S. aureus with minimal inhibitory concentrations (MICs) of 32 µg/mL and 4 µg/mL, respectively. The fact that 1-2 showed stronger activity against S. aureus 209P than 3 indicated that the epoxy unit was important for antimicrobial activity. This structure-activity tendency of chalcomycins against S. aureus is different from that of aldgamycins reported in our previous research, which provide a valuable example for the phenomenon that 16-membered macrolides with different sugars do not have parallel structure-activity relationships.

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Section: Introductionmentioning

confidence: 99%

Chalcomycins from Marine-Derived Streptomyces sp. and Their Antimicrobial Activities

et al. 2017

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Phthalides: Distribution in Nature, Chemical Reactivity, Synthesis, and Biological Activity

León

Del-Ángel

Ávila

et al. 2017

Progress in the Chemistry of Organic Natural Products

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Phthalides are a relatively small group of natural compounds confined to several plant families and some genera of fungi and liverworts. They are divided into two structural groups, the monomeric and dimeric phthalides, and known mainly as bioactive constituents of different plant species used traditionally for medicinal purposes in Asia, Europe, and North America.The first reports on the chemistry of phthalides appeared at the end of the nineteenth century, in which they were identified as the odor constituents of the essential oil of celery (Apium graveolens) by Ciamician and Silber (1897). In the first half of the last century, phthalides were isolated from Cnidium officinale and Ligusticum acutilobum, species widely used in Asian traditional medicine, and from Levisticum officinale, a species used as food and condiment. Throughout the second part of the twentieth century, phthalides have been characterized from several plant families, namely Asteraceae, Leguminosae, Orchidaceae and Rutaceae, among others, but mainly from the Umbelliferae (syn Apiaceae) family, and the major contributors have been the following species used in traditional medicine: Ligusticum chuanxiong (Chinese name: Chuanxiong), Angelica sinensis (Chinese name: Danggui), Cnidium officinale (Japanese name: Senkyu), Angelica acutiloba (Japanese name: Toki), and Ligusticum porteri (Hispanic name: Oshá). Phthalides are also constituents of several genera of fungi, such as Penicillium, Alternaria and Pestalotiopsis, and some liverworts.Different chromatographic, spectrometric, and two-dimensional nuclear magnetic resonance (NMR) techniques have been used for the isolation and structural characterization of phthalides in extracts, and for assessing the quality of plant material containing this type of compound. Isotopic labeling has established the biosynthesis of phthalides via linkage of acetate units forming polyketide intermediates.Chemical transformations of monomeric phthalides have included oxidation, reduction, addition, elimination, and cycloaddition reactions, and treatments with Lewis acids of (Z)-ligustilide have afforded linear dimers. Some intramolecular condensations and differentiated cyclizations of the dimeric phthalides have been carried out, providing evidences for the particular chemical reactivity of these compounds.Several structural modifications of phthalides have been carried out subjecting them to microbial transformations by different species of bacteria, fungi and algae, and these included resolutions of racemic mixtures and oxidations, among others.The [π4s + π2s] and [π2s + π2s] cycloadditions of (Z)-ligustilide for the synthesis of dimeric phthalides have been reported, and different approaches involving cyclizations, Alder-Rickert reactions, Sharpless asymmetric hydroxylations, or Grignard additions have been used for the synthesis of monomeric phthalides. The use of phthalides as building blocks for divergent oriented synthesis has been proven.Many of the naturally occurring phthalides display different biological...

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New phthalide derivatives from the Biscogniauxia sp. and their activities

Zhao²,

Xie

et al. 2019

Fitoterapia

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New α-pyrone and phthalide from the Xylariaceae fungus

Cited by 7 publications

References 25 publications

Chalcomycins from Marine-Derived Streptomyces sp. and Their Antimicrobial Activities

Chalcomycins from Marine-Derived Streptomyces sp. and Their Antimicrobial Activities

Phthalides: Distribution in Nature, Chemical Reactivity, Synthesis, and Biological Activity

New phthalide derivatives from the Biscogniauxia sp. and their activities

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