Effect of Culture Conditions on Metabolite Production of Xylaria sp.

Zhang, Hongqi; Deng, Zhangshuang; Guo, Zhiyong; Peng, Yan; Huang, Nianyu; He, Hui; Tu, Xuan; Zou, Kun

doi:10.3390/molecules20057940

Cited by 17 publications

(13 citation statements)

References 25 publications

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“…Compound 1 had a molecular formula of C 35 H 44 O 7 as determined by high-resolution electrospray ionization mass spectrometry (HRESIMS). In the 1 H NMR spectrum, the characteristic signals at δ 14.30 (1H, s, 13-OH), 13.08 (1H, s, 7-OH), 6.79 (1H, s, H-8), 5.02 (2H, t, H-29), 4.84 (1H, t, H-21), 4.77 (1H, t, H-17), 3.86 (2H, s, H-33), 2.81 (3H, s, H-15), 2.52 (1H, d, H-16), 2.11 (3H, s, H-14), 1.58 (3H, s, H-31), 1.50 (3H, s, H-15), 1.36 (3H, s, H-34), 1.24 (3H, s, H-35) were clearly observed. Starting from these characteristic proton signals, the following key heteronuclear multiple bond correlations (HMBCs) of 13 spectrum of 1 presented a negative Cotton effect at 350 nm (Figure S1); thus the configuration of C-1 was considered to be S based on the empirical rule.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The biogenetic relationship suggested it should share the 4 R -configuration with 22 . The remaining compounds were identified as rosellichalasin ( 7 ), cytochalasin Z 17 ( 8 ), cytochalasin Z 9 ( 9 ), cytochalasin Z 8 ( 10 ), cytochalasin Z 7 ( 11 ), cytochalasin Z 13 ( 12 ), aspulvinone Q ( 14 ), aspulvinone P ( 15 ), aspulvinone E ( 16 ), 3′,4′,4-trihydroxypulvinone ( 17 ), 3,4,4′-trihydroxypulvinone ( 18 ), aspernolide H ( 19 ), aspernolide I ( 20 ), aspernolide K ( 21 ), butyrolactone II ( 24 ), 2- O -methyl butyrolactone II ( 25 ), epicocconigrone A ( 26 ), epicoccolide B ( 27 ), 1,3-dihydro-4,6-dihydroxy-7-methylisobenzofuran ( 28 ), monomethylosoic acid ( 29 ), , asterric acid ( 30 ), , methyl-dichloroasterrate ( 31 ), sulochrin ( 32 ), and dihydrogeodin ( 33 ) by comparing their NMR data with those reported.…”

Section: Resultsmentioning

confidence: 99%

“…While searching for HIV-1 inhibitors from plant endophytes, it was found that the EtOAc-soluble fraction of an extract from rice cultures of CPCC 400735 displayed significant HIV-1 inhibitory effect. Investigation of the chemical constituents of the bioactive fraction led us to obtain 33 metabolites, including five new phenalenone derivatives, asperphenalenones A−E (1−5), one new aspochalasin, aspochalasin R (6), one new aspulvinone, aspulvinone R (13) (Chart 1), and 26 known compounds (7− 12 and 14−33, Chart 2); all were tested for anti-HIV-1 activity.…”

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confidence: 99%

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Metabolites from the Plant Endophytic Fungus Aspergillus sp. CPCC 400735 and Their Anti-HIV Activities

et al. 2017

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Thirty-three metabolites including five phenalenone derivatives (1-5), seven cytochalasins (6-12), thirteen butenolides (13-25), and eight phenyl derivatives (26-33) were isolated from Aspergillus sp. CPCC 400735 cultured on rice. The structures of all compounds were elucidated by NMR, MS, and CD experiments, of which 1-5 (asperphenalenones A-E), 6 (aspochalasin R), and 13 (aspulvinone R) were identified as new compounds. Specifically, asperphenalenones A-E (1-5) represent an unusual structure composed of a linear diterpene derivative linked to a phenalenone derivative via a C-C bond. Compounds 1, 4, 10, and 26 exhibited anti-HIV activity with IC values of 4.5, 2.4, 9.2, and 6.6 μM, respectively (lamivudine 0.1 μM; efavirenz, 0.4 × 10 μM).

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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Metabolites from the Plant Endophytic Fungus Aspergillus sp. CPCC 400735 and Their Anti-HIV Activities

et al. 2017

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“…Xylapyrone C ( 23) is a pyrone compound isolated from a fungus and has a hydroxy group in its side chain. 18 First, we synthesized this compound via the iteration cycle (Scheme 4). The loading of ω-hydroxythioester 14 onto carboxy-functionalized resin 1 and hydrolysis of the resulting thioester 15 were performed.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Solid-Phase Biomimetic Synthesis of Polyketide

2021

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Solid-phase biomimetic polyketide synthesis has been developed. This method is composed of (i) carbon chain elongation of resin-bound carboxylic acid via decarboxylative Claisen condensation with malonic acid half thioester, (ii) stepwise transformation of the resulting β-ketothioester, and (iii) hydrolysis of thioester to regenerate the carboxylic acid for the next iteration cycle. Colorimetric tests were available for convenient monitoring of the solid-phase reactions; malachite green (basic dye) and iron(III) chloride successfully detected the carboxylic acid and the β-ketothioester, respectively. In addition, gel-phase 13 C NMR could be utilized to confirm the progress of substrate immobilization. The established method was applied to the synthesis of the natural products, xylapyrone C and kavain. The present method could be further extended to the synthesis of (R)-kavain with catalytic diastereoselective asymmetric transfer hydrogenation as a key step.

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“…In another study by Zhang et al79 reported that plant-derived fungus Xylaria sp. suppressed the production of known cytochalasin-type metabolites to express new α-pyrone derivatives, xylapyrones A-F (1.53-1.58), when the culture medium change from solid to liquid shaking.…”

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confidence: 99%

Fungal biodiscovery: Strategies to explore fungal secondary metabolite potential

Gedara¹,

Pradeep²

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Fungi have been an inspiring source of diverse secondary metabolites, with a number of metabolites developed as pharmaceuticals and agrochemicals. Despite the past success, fungal biodiscovery has been challenged with the excessive rediscovery of known metabolites. This thesis is focused on investigating four selected strategies to explore fungal secondary metabolite potential to discover novel and bioactive metabolites. This includes, bioactivity-guided isolation, varying cultivation conditions, application of advance analytical techniques and microbial co-cultivation. A library of ×185 microbes, including fungi (×132) and Streptomyces (×53), was constructed from a total of ×28 samples collected from terrestrial and marine samples. High-throughput miniaturized 24-well microbioreactor culture approach was used to generate extracts from solid (agar) and liquid (broth shaken) cultures to prepare a crude extract library, which was subjected to chemical and bioactivity profiling using HPLC-DAD-MS and UHPLC-QTOF. Two innovative bioassays to discover bioactive metabolites in the extracts were employed; (i) The larval development assay (LDA), used to detect anti-parasitic metabolites against drug (monepantel) resistant sheep intestinal parasite Haemonchus contortus and (ii) GABA (β-aminobutyric acid) receptor inhibitory activity, to detect molecules that may have application as anti-anxiety drugs. Selected strains were subjected to a program of analytical miniaturized cultivation, supported by UHPLC-DAD-MS and UHPLC-QTOF profiling to explore the wider secondary metabolite potential of fungi. The metabolite production was visualised using the Global Natural Product Social (GNPS) molecular networking analysis. Based on the chemical and bioactivity profiling, a total of ×6 fungi were selected for further investigation, and the isolation and characterization of metabolites from these strains are discussed in this PhD thesis.Chapter 1 highlights the importance of understanding, and exploring silent fungal secondary metabolism. This chapter also reviews different strategies reported in the literature for the discovery of novel and bioactive metabolites from fungi, with main focus on (i) bioactivity guided isolation, (ii) varying cultivation condition, (iii) application of advance analytical techniques and (iv) microbial cocultivation.Chapter 2 focuses on investigating bioactivity-guided isolation as a prioritizing tool for microbial extracts to isolate biologically active metabolites. Anthelmintic metabolites identified from Penicillium sp. CMB-TS015 and Purpureocillium sp. CMB-F551 are discussed in this chapter.Chapter 3 discusses continued chemical and bioactivity investigation on Penicillium sp. CMB-TS015.Isolation, characterization and bioactivity profiling of three new fungal metabolites (+)spiroquinazoline B, (+)-fumiquinazoline J and the tetramic acid chaunolidine D, are described in this chapter.

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Effect of Culture Conditions on Metabolite Production of Xylaria sp.

Cited by 17 publications

References 25 publications

Metabolites from the Plant Endophytic Fungus Aspergillus sp. CPCC 400735 and Their Anti-HIV Activities

Metabolites from the Plant Endophytic Fungus Aspergillus sp. CPCC 400735 and Their Anti-HIV Activities

Solid-Phase Biomimetic Synthesis of Polyketide

Fungal biodiscovery: Strategies to explore fungal secondary metabolite potential

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