Chrysamides A–C, Three Dimeric Nitrophenyl <i>trans</i>-Epoxyamides Produced by the Deep-Sea-Derived Fungus <i>Penicillium chrysogenum</i> SCSIO41001

Chen, Shengtian; Wang, Junfeng; Lin, Xiuping; Zhao, Bing-Xin; Wei, Xiaoyi; Li, Guangqiang; Kaliaperumal, Kumaravel; Liao, Shengrong; Yang, Bin; Zhou, Xuefeng; Liu, Juan; Xu, Shi‐Hai; Liu, Yonghong

doi:10.1021/acs.orglett.6b01699

Cited by 60 publications

(30 citation statements)

References 25 publications

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“…A variety of metabolites containing nitro functional groups have been detected in fungal genera known to harbor denitrifying representatives (63), yet mechanistic explanations for nitration reactions in fungi remain elusive. The addition of a nitro functional group to a metabolite represents a potential mechanism for enhancing its toxicity or functional specificity (64).…”

Section: Discussionmentioning

confidence: 99%

Phylogenomics reveals dynamic evolution of fungal nitric oxide reductases and their relationship to secondary metabolism

Higgins

Schadt

Matheny

et al. 2018

Preprint

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Fungi expressing P450nor, an unconventional nitric oxide (NO) reducing cytochrome P450, are thought to be significant contributors to soil nitrous oxide (N2O) emissions. However, fungal contributions to N2O emissions remain uncertain due to inconsistencies in measurements of N2O formation by fungi. Much of the N2O emitted from antibiotic-amended soil microcosms is attributed to fungal activity, yet fungal isolates examined in pure culture are poor N2O producers. To assist in reconciling these conflicting observations and produce a benchmark genomic analysis of fungal denitrifiers, genes underlying fungal denitrification were examined in >700 fungal genomes. Of 167 p450nor–containing genomes identified, 0, 30, and 48 also harbored the denitrification genes narG, napA or nirK, respectively. Compared to napA and nirK, p450nor was twice as abundant and exhibited two to five-fold more gene duplications, losses, and transfers, indicating a disconnect between p450nor presence and denitrification potential. Furthermore, co-occurrence of p450nor with genes encoding NO-detoxifying flavohemoglobins (Spearman r = 0.87, p = 1.6e−10) confounds hypotheses regarding P450nor’s primary role in NO detoxification. Instead, ancestral state reconstruction united P450nor with actinobacterial cytochrome P450s (CYP105) involved in secondary metabolism (SM) and 19 (11 %) p450nor-containing genomic regions were predicted to be SM clusters. Another 40 (24 %) genomes harbored genes nearby p450nor predicted to encode hallmark SM functions, providing additional contextual evidence linking p450nor to SM. These findings underscore the potential physiological implications of widespread p450nor gene transfer, support the novel affiliation of p450nor with fungal SM, and challenge the hypothesis of p450nor’s primary role in denitrification.

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Section: Discussionmentioning

confidence: 99%

Phylogenomics reveals dynamic evolution of fungal nitric oxide reductases and their relationship to secondary metabolism

Higgins

Schadt

Matheny

et al. 2018

Preprint

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“…During our continuous study in exploring new bioactive natural products from marine microorganisms [ 15 , 16 , 17 , 18 ], the deep-sea-derived fungus Leptosphaeria sp. SCSIO 41005, isolated from a marine sediment sample collected from the Indian Ocean at a depth of 3614 m, was investigated.…”

Section: Introductionmentioning

confidence: 99%

Isobenzofuranones and Isochromenones from the Deep-Sea Derived Fungus Leptosphaeria sp. SCSIO 41005

et al. 2017

Self Cite

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Four new isobenzofuranones, leptosphaerins J–M (1–4), including an unusual naturally-occurring centrosymmetric dimer skeleton (1), and two new isochromenones, clearanols I–J (9–10), were obtained from a culture of a deep-sea sediment-derived fungus Leptosphaeria sp. SCSIO 41005, together with four known isobenzofuranones (5–8) and six known isochromenones (11–16). These structures were elucidated by extensive spectroscopic analyses, and absolute configurations were assigned on the basis of electronic circular dichroism and optical rotations data comparison. Additionally, the absolute configurations of the new compounds 1 and 9, together with the known one 7 with stereochemistry undetermined, were further confirmed by single crystal X-ray diffraction experiments. A plausible biosynthetic pathway of these isobenzofuranones and isochromenones was also proposed.

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“…A variety of metabolites containing nitro functional groups have been detected in fungal genera known to harbor denitrifying representatives ( Chen et al. 2016 ), yet mechanistic explanations for nitration reactions in fungi remain elusive.…”

Section: Discussionmentioning

confidence: 99%

Phylogenomics Reveal the Dynamic Evolution of Fungal Nitric Oxide Reductases and Their Relationship to Secondary Metabolism

Higgins

Schadt

Matheny

et al. 2018

Genome Biology and Evolution

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Fungi expressing P450nor, an unconventional nitric oxide (NO) reducing cytochrome P450, are considered significant contributors to environmental nitrous oxide (N2O) emissions. Despite extensive efforts, fungal contributions to N2O emissions remain uncertain. For example, the majority of N2O emitted from antibiotic-amended soil microcosms is attributed to fungal activity, yet axenic fungal cultures do not couple N-oxyanion respiration to growth and these fungi produce only minor quantities of N2O. To assist in reconciling these conflicting observations and produce a benchmark genomic analysis of fungal denitrifiers, genes underlying denitrification were examined in >700 fungal genomes. Of 167 p450nor—containing genomes identified, 0, 30, and 48 also harbored the denitrification genes narG, napA, or nirK, respectively. Compared with napA and nirK, p450nor was twice as abundant and exhibited 2–5-fold more gene duplications, losses, and transfers, indicating a disconnect between p450nor presence and denitrification potential. Furthermore, cooccurrence of p450nor with genes encoding NO-detoxifying flavohemoglobins (Spearman r = 0.87, p = 1.6e−10) confounds hypotheses regarding P450nor’s primary role in NO detoxification. Instead, ancestral state reconstruction united P450nor with actinobacterial cytochrome P450s (CYP105) involved in secondary metabolism (SM) and 19 (11%) p450nor-containing genomic regions were predicted to be SM clusters. Another 40 (24%) genomes harbored genes nearby p450nor predicted to encode hallmark SM functions, providing additional contextual evidence linking p450nor to SM. These findings underscore the potential physiological implications of widespread p450nor gene transfer, support the undiscovered affiliation of p450nor with fungal SM, and challenge the hypothesis of p450nor’s primary role in denitrification.

show abstract

Chrysamides A–C, Three Dimeric Nitrophenyl trans-Epoxyamides Produced by the Deep-Sea-Derived Fungus Penicillium chrysogenum SCSIO41001

Cited by 60 publications

References 25 publications

Phylogenomics reveals dynamic evolution of fungal nitric oxide reductases and their relationship to secondary metabolism

Phylogenomics reveals dynamic evolution of fungal nitric oxide reductases and their relationship to secondary metabolism

Isobenzofuranones and Isochromenones from the Deep-Sea Derived Fungus Leptosphaeria sp. SCSIO 41005

Phylogenomics Reveal the Dynamic Evolution of Fungal Nitric Oxide Reductases and Their Relationship to Secondary Metabolism

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