Cytotoxic cochlioquinone derivatives from the endophytic fungus Bipolaris sorokiniana derived from Pogostemon cablin

Wang, Mo; Sun, Zhang‐Hua; Chen, Yuchan; Liu, Hongxin; Li, Haohua; Tan, Genjia; Li, Saini; Guo, X. L.; Zhang, Weiyang

doi:10.1016/j.fitote.2016.02.005

Cited by 54 publications

(26 citation statements)

References 20 publications

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“…Further LC-MS analysis of crude extracts revealed that both strains produced an array of compounds with similar UV absorbance and molecular weights (ca. [13,14] Structurally,c ompounds 1-10 share a6 /6/6/6-tetracyclic ring system consisting of as esquiterpenoid part and ap olyketide part. To further correlate whether these compounds were putative meroterpenoids, atnG,aN R-PKS gene in the atn gene cluster,w as inactivated.…”

mentioning

confidence: 55%

“…Compounds 1-8 have not be reported yet, whereas, 9 and 10 were determined to be cochliquninone Da nd isocochliquninone E, respectively. [13,14] Structurally,c ompounds 1-10 share a6 /6/6/6-tetracyclic ring system consisting of as esquiterpenoid part and ap olyketide part. Furthermore,t he polyketide subunit in 1-10 consists of an aromatic ring and aside chain, thus suggesting that its biosynthetic origin could be derived from an HR-PKS/ NR-PKS pair, [12] which is consistent with the presence of AtnH/NtnH and AtnG/NtnG in the respective gene clusters.…”

mentioning

confidence: 99%

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Genome Mining and Comparative Biosynthesis of Meroterpenoids from Two Phylogenetically Distinct Fungi

Zhang

Wang

et al. 2018

Angew Chem Int Ed

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Two homologous meroterpenoid gene clusters consisting of contiguous genes encoding polyketide synthase (PKS), prenyltransferase (PT), terpenoid cyclase (TC) and other tailoring enzymes were identified from two phylogenetically distinct fungi through computational analysis. Media optimization guided by reverse-transcription PCR (RT-PCR) enabled two strains to produce eight new and two known meroterpenoids (1-10). Using gene inactivation, heterologous expression, and biochemical analyses, we revealed a new polyketide-terpenoid assembly line that utilizes a pair of PKSs to synthesize 2,4-dihydroxy-6-alkylbenzoic acid, followed by oxidative decarboxylation, farnesyl transfer, and terpene cyclization to construct the meroterpenoid scaffold. In addition, two of the isolated meroterpenoids (3 and 17 d) showed immunosuppressive bioactivity. Our work reveals a new strategy for meroterpenoid natural products discovery, and reveals the biosynthetic pathway for compounds 1-10.

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confidence: 55%

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confidence: 99%

Genome Mining and Comparative Biosynthesis of Meroterpenoids from Two Phylogenetically Distinct Fungi

Zhang

Wang

et al. 2018

Angew Chem Int Ed

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“…Sample surface sterilization was conducted by immersing the tissues in 75 % ethanol for 1-3 min and rinsing thrice with sterile water and 0.1 % HgCl for 2-3 min. Then, the samples were rinsed 5 times in sterile water, thoroughly dried on sterile filter paper in a laminar flow chamber, and stored at − 80°C [30].…”

Section: Sample Collectionmentioning

confidence: 99%

Endophytic Microbiota Comparison of Dendrobium huoshanense Root and Stem in Different Growth Years

et al. 2019

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The endophytic microbiome in medicinal plants is rich and diverse, but few studies have followed the endophytic microbiome of medicinal plants in different tissues with their growth. In this study, we examined the endophytic bacterial and fungal community structures associated with both the stem and root compartments of Dendrobium huoshanense at different growth years via high-throughput sequencing of 16S rRNA genes and nrDNA fragments of internal transcribed spacer regions. Results indicated that more diverse prokaryotic and fungal operational taxonomic units were detected in roots than in stems, and the alpha diversity of endophytic prokaryotic significantly differed among the 1-, 2-, and 3-year-old roots. The dominant bacterial phyla Proteobacteria Firmicutes, Actinobacteria, Bacteroidetes, and Acidobacteria, and fungal phyla Ascomycota, Basidiomycota, and Ascomycota were detected in the stems and roots with 3 growth years. Moreover, linear discriminant effect size analysis revealed 138 differentially abundant taxonomic clades in the bacterial level, and 197 in the fungal level in six groups. Our results provide evidence for endophytic microbiota communities depending on the tissues and growth years of D. huoshanense. The results from this study should be useful to better understand medicinal plant-microbe interactions.

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“…Z14‐w, were isolated and characterized by HRMS, X‐ray diffraction (Figure S4), and NMR (Table S5–S12 and Figure S5). Compounds 1 – 8 have not be reported yet, whereas, 9 and 10 were determined to be cochliquninone D and isocochliquninone E, respectively …”

Section: Methodsmentioning

confidence: 99%

Genome Mining and Comparative Biosynthesis of Meroterpenoids from Two Phylogenetically Distinct Fungi

Zhang

Wang

et al. 2018

Angewandte Chemie

View full text Add to dashboard Cite

Two homologous meroterpenoid gene clusters consisting of contiguous genes encoding polyketide synthase (PKS), prenyltransferase (PT), terpenoid cyclase (TC) and other tailoring enzymes were identified from two phylogenetically distinct fungi through computational analysis. Media optimization guided by reverse‐transcription PCR (RT‐PCR) enabled two strains to produce eight new and two known meroterpenoids (1–10). Using gene inactivation, heterologous expression, and biochemical analyses, we revealed a new polyketide‐terpenoid assembly line that utilizes a pair of PKSs to synthesize 2,4‐dihydroxy‐6‐alkylbenzoic acid, followed by oxidative decarboxylation, farnesyl transfer, and terpene cyclization to construct the meroterpenoid scaffold. In addition, two of the isolated meroterpenoids (3 and 17 d) showed immunosuppressive bioactivity. Our work reveals a new strategy for meroterpenoid natural products discovery, and reveals the biosynthetic pathway for compounds 1–10.

show abstract

Cytotoxic cochlioquinone derivatives from the endophytic fungus Bipolaris sorokiniana derived from Pogostemon cablin

Cited by 54 publications

References 20 publications

Genome Mining and Comparative Biosynthesis of Meroterpenoids from Two Phylogenetically Distinct Fungi

Genome Mining and Comparative Biosynthesis of Meroterpenoids from Two Phylogenetically Distinct Fungi

Endophytic Microbiota Comparison of Dendrobium huoshanense Root and Stem in Different Growth Years

Genome Mining and Comparative Biosynthesis of Meroterpenoids from Two Phylogenetically Distinct Fungi

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