Acautalides A–C, Neuroprotective Diels–Alder Adducts from Solid-State Cultivated <i>Acaulium</i> sp. H-JQSF

Tong, Zhi Wu; Xie, Xia Hong; Wang, Ting Ting; Lu, Ming; Jiao, Rui Hua; Ge, Hui; Hu, Gang; Tan, Ren Xiang

doi:10.1021/acs.orglett.1c02089

Cited by 13 publications

(11 citation statements)

References 26 publications

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“…Microechmycin D ( 4 ) and E ( 5 ) can be synthesized through the actions of esterification between glycerol and two molecules of 1 . This glycerol esterification has been observed in acautalides C discovery from Acaulium sp H-JQSF [ 33 ]. The discovery of microechmycins adds to the inventory of secondary metabolites that can be biosynthesized by Micromonospora sp.…”

Section: Discussionsupporting

confidence: 57%

Genomics-Driven Discovery of Benzoxazole Alkaloids from the Marine-Derived Micromonospora sp. SCSIO 07395

et al. 2023

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Benzoxazole alkaloids exhibit a diverse array of structures and interesting biological activities. Herein we report the identification of a benzoxazole alkaloid-encoding biosynthetic gene cluster (mich BGC) in the marine-derived actinomycete Micromonospora sp. SCSIO 07395 and the heterologous expression of this BGC in Streptomyces albus. This approach led to the discovery of five new benzoxazole alkaloids microechmycin A–E (1–5), and a previously synthesized compound 6. Their structures were elucidated by HRESIMS and 1D and 2D NMR data. Microechmycin A (1) showed moderate antibacterial activity against Micrococcus luteus SCSIO ML01 with the minimal inhibitory concentration (MIC) value of 8 μg mL−1.

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Section: Discussionsupporting

confidence: 57%

Genomics-Driven Discovery of Benzoxazole Alkaloids from the Marine-Derived Micromonospora sp. SCSIO 07395

et al. 2023

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“…Microbial community is extensive among insects. As a special kind of microbial community, insect-associated fungi have been a source of new microbial resources [ 29 , 30 ] and biologically active natural products [ 16 , 31 , 32 ]. While fungi were present in A. mellifera ligustica , the leading research mainly focused on the honeycomb, honeybee gut, pollen, and bread [ 23 , 33 – 36 ].…”

Section: Discussionmentioning

confidence: 99%

Community composition, bacterial symbionts, antibacterial and antioxidant activities of honeybee-associated fungi

et al. 2022

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Background Fungi associated with insects represent one potentially rich source for the discovery of novel metabolites. However, a comprehensive understanding of the fungal communities of Apis mellifera ligustica remains elusive. Results Here, we investigated the phylogenetic diversity and community composition of honeybee-associated fungi using combination of culture-dependent and culture-independent approaches. A total of forty-five fungi were isolated and purified from the Apis mellifera ligustica, royal jelly, and honeycomb, which belonged to four classes and eleven different genera. Furthermore, 28 bacterial 16S rRNA gene sequences were obtained by PCR from the fungal metagenome. High-throughput sequencing analyses revealed that the fungal communities were more diverse, a total of 62 fungal genera were detected in the honeybee gut by culture-independent method, whereas only 4 genera were isolated by culture-dependent method. Similarly, 247 fungal genera were detected in the honeycomb, whereas only 4 genera were isolated. In addition, we assessed the antibacterial and antioxidant activities of fungal isolates. Most fungal crude extracts obtained from the cultivation supernatant exhibited antioxidant activities. Only two fungal crude extracts displayed moderate activity against Escherichia coli and Staphylococcus aureus. Chemical analysis of Chaetomium subaffine MFFC22 led to the discovery of three known compounds, including cochliodinol (1), emodin (2), chrysophanol (3). Among them, cochliodinol (1) showed intense DPPH radical scavenging activity with the 50% inhibitory concentration (IC50) of 3.06 μg/mL, which was comparable to that of the positive ascorbic acid (IC50 = 2.25 μg/mL). Compound 2 displayed weak inhibitory activities against Micrococcus tetragenus and S. aureus. Conclusions This research provided a fundamental clue for the complex interactions among honeybees, fungi, bacterial symbionts, and the effects on the honeybee. Furthermore, the diversity of honeybee-associated fungi had great potential in finding the resource of new species and antioxidants.

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“…The fungal polyketide acautalide A ( 43 ) is produced from the solid-state cultivation of isopod Armadillidium vulgare -associated Acaulium sp. H-JQSF on rice medium, and exhibits neuroprotective bioactivity with antiparkinsonic potential in the 1-methyl-4-phenylpyridinium-challenged nematode model [ 63 ]. The architectural features of 43 indicated that two biosynthetic precursors 10-keto-acaudiol and octadeca-9,11,13-trienoic acid intertwined together through intermolecular Diels–Alder cycloaddition ( Figure 10 ).…”

Section: Representative Fungal Nps Might Be Biosynthesized By Two Sep...mentioning

confidence: 99%

“…Interestingly, the obtained 43 was in enantiomerically pure form, thus the Diels–Alder cycloaddition might be truly enzymatic. A fungal Diels–Alderase could be expected to catalyze the intermolecular [4 + 2]-cycloaddition in the assembly line of 43 [ 63 ].…”

Section: Representative Fungal Nps Might Be Biosynthesized By Two Sep...mentioning

confidence: 99%

Biosynthesis of Fungal Natural Products Involving Two Separate Pathway Crosstalk

Dai

Shen

Zhang

et al. 2022

JoF

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Fungal natural products (NPs) usually possess complicated structures, exhibit satisfactory bioactivities, and are an outstanding source of drug leads, such as the cholesterol-lowering drug lovastatin and the immunosuppressive drug mycophenolic acid. The fungal NPs biosynthetic genes are always arranged within one single biosynthetic gene cluster (BGC). However, a rare but fascinating phenomenon that a crosstalk between two separate BGCs is indispensable to some fungal dimeric NPs biosynthesis has attracted increasing attention. The hybridization of two separate BGCs not only increases the structural complexity and chemical diversity of fungal NPs, but also expands the scope of bioactivities. More importantly, the underlying mechanism for this hybridization process is poorly understood and needs further exploration, especially the determination of BGCs for each building block construction and the identification of enzyme(s) catalyzing the two biosynthetic precursors coupling processes such as Diels–Alder cycloaddition and Michael addition. In this review, we summarized the fungal NPs produced by functional crosstalk of two discrete BGCs, and highlighted their biosynthetic processes, which might shed new light on genome mining for fungal NPs with unprecedented frameworks, and provide valuable insights into the investigation of mysterious biosynthetic mechanisms of fungal dimeric NPs which are constructed by collaboration of two separate BGCs.

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Acautalides A–C, Neuroprotective Diels–Alder Adducts from Solid-State Cultivated Acaulium sp. H-JQSF

Cited by 13 publications

References 26 publications

Genomics-Driven Discovery of Benzoxazole Alkaloids from the Marine-Derived Micromonospora sp. SCSIO 07395

Genomics-Driven Discovery of Benzoxazole Alkaloids from the Marine-Derived Micromonospora sp. SCSIO 07395

Community composition, bacterial symbionts, antibacterial and antioxidant activities of honeybee-associated fungi

Biosynthesis of Fungal Natural Products Involving Two Separate Pathway Crosstalk

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