Two new diketopiperazines and a new glucosyl sesterterpene from Alternaria alternata, an endophytic fungi from Ceratostigma griffithii

Guo, Da‐Le; Zhao, Min; Xiao, Shiji; Xia, Bing; Wan, Bo; Gu, Yu‐Cheng; Ding, Li‐Sheng; Zhou, Yan

doi:10.1016/j.phytol.2015.10.024

Cited by 14 publications

(8 citation statements)

References 17 publications

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“…It should be noted that frequent occurrence of terpestacin in more than 20 fungal strains ( Arthrinium , Cleistothelebolus , Neogymnomyces , Drechslera , Ulocladium , and various Fusarium ) have been reported in the literature and that homologous gene clusters with tpc have been found in terpestacin/fusaproliferin producers such as A. alternata , B. sorokiniana , and F. proliferatum (Figure ). The wide distribution of the tpc gene cluster across species suggested the importance of terpestacin/fusaproliferin for those fungi.…”

Section: Results and Discussionmentioning

confidence: 99%

Total Biosynthesis of Antiangiogenic Agent (−)-Terpestacin by Artificial Reconstitution of the Biosynthetic Machinery in Aspergillus oryzae

et al. 2018

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The total biosynthesis of (-)-terpestacin was achieved by heterologous expression of four biosynthetic enzyme genes ( tpcA- D) in Aspergillus oryzae. After construction of preterpestacin I by the action of bifunctional terpene synthase (TpcA), two cytochrome P450s (TpcBC) activate inert C-H bond to install three hydroxyl groups on the A-ring in stereo- and regioselective manners. Subsequently, a flavin-dependent oxidase (TpcD) catalyzes oxidation of the vicinal diol moiety to give a α-diketone, which undergoes an enolization to furnish terpestacin. The successful synthesis of structurally elaborated terpestacin showed that a reconstitution approach that harnesses several biosynthetic enzyme genes in A. oryzae could be a promising alternative to the current chemical synthesis of natural terpenoids.

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Section: Results and Discussionmentioning

confidence: 99%

Total Biosynthesis of Antiangiogenic Agent (−)-Terpestacin by Artificial Reconstitution of the Biosynthetic Machinery in Aspergillus oryzae

et al. 2018

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“…The 1 H NMR (400 MHz, DMSO) spectrum (Supporting Information Figure 7 The 13 C NMR (Supporting Information Figure 7) and distortionless enhancement by polarization transfer (DEPT) spectra showed about 12 and 7 peaks, respectively, where the missing peaks in DEPT indicate the deprotonated carbons (Supporting Information Figure 8). Since the isolated fraction 2 was symmetry in nature, we got 12 carbon signals for 13 C NMR and 7 carbon signals 16,18,11,13,19,15,10,14,1,3,17,12,22,20,24,21, and 23rd carbon, while the rest of the carbons were deprotonated.…”

Section: Structure Elucidation Of Fractionmentioning

confidence: 99%

“…FITR, Fourier-transform infrared; GC-MS, gas chromatography-mass spectrometry for DEBT-135 spectra. The peaks observed in DEBT-135 spectra include δ C 129.42, 129.31, 128.97, 128.73, 128.44, 127.53, and 126.46 with respective to the carbons at positions16,18,11,13,19,15,10,14,1,3,17,12,22,20,24,21, and 23rd carbon, while the rest of the carbons were deprotonated.…”

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confidence: 99%

Secondary metabolite as therapeutic agent from endophytic fungi Alternaria longipes strain VITN14G of mangrove plant Avicennia officinalis

Ranganathan

Gayathri

2018

J of Cellular Biochemistry

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Endophytic fungi, especially from mangrove plants, are rich source of secondary metabolites, which plays a major role in various pharmacological actions preferably in cancer and bacterial infections. To perceive its role in antidiabetic activity we isolated and tested the metabolites derived from a novel strain Alternaria longipes strain VITN14G obtained from mangrove plant Avicennia officinalis. The crude extract was analyzed for antidiabetic activity and subjected to column chromatography. The isolated fractions were screened in vitro for α-glucosidase and α-amylase inhibitory activities. The cytotoxicity of the isolated fractions was studied on L929 cell lines. Following which, the screened fraction 2 was allowed for structure elucidation using gas chromatography-mass spectrometry, one-dimensional, two-dimensional nuclear magnetic resonance spectroscopy, ultraviolet, and Fourier-transform infrared analysis. The binding energies of the isolated fraction 2 with glycolytic enzymes were calculated by molecular docking studies using AutoDock Vina. The isolated fraction 2 identified as 2,4,6-triphenylaniline, showed no significant difference in α-amylase inhibition rates and a significant difference of 10% in α-glucosidase inhibition rates than that of the standard drug acarbose. Further, the cytotoxicity assay of the isolated fraction 2 resulted in a cell viability of 73.96%. Supportingly, in silico studies showed 2,4,6-triphenylaniline to produce a stronger binding affinity toward the glycolytic enzyme targets. The compound 2,4,6-triphenylaniline isolated from A. longipes strain VITN14G exhibited satisfactory antidiabetic activity for type 2 diabetes in vitro, which will further be confirmed by in vivo studies. Successful outcome of the study will result in a natural substitute for existing synthetic antidiabetic drugs. K E Y W O R D Santidiabetic, endophytic fungi, type 2 diabetes, α-glucosidase, 2,4,6-triphenylaniline

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“…HM166, which was isolated from the small quinoa in the Inner Mongolia Autonomous Region of Western China. As a result, eight terpenoids, including seven undescribed sesquiterpenes ( 1–7 ), and three known compounds, (+)-schisanwilsonene A ( 8 ), 14 (−)-terpestacin ( 9 ), and fusaproliferin ( 10 ), 15 were isolated and identified (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Carotane sesquiterpenoids A–G from the desert endophytic fungus Fusarium sp. HM 166

Zhang

Jiang

et al. 2022

RSC Adv.

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Two new diketopiperazines and a new glucosyl sesterterpene from Alternaria alternata, an endophytic fungi from Ceratostigma griffithii

Cited by 14 publications

References 17 publications

Total Biosynthesis of Antiangiogenic Agent (−)-Terpestacin by Artificial Reconstitution of the Biosynthetic Machinery in Aspergillus oryzae

Total Biosynthesis of Antiangiogenic Agent (−)-Terpestacin by Artificial Reconstitution of the Biosynthetic Machinery in Aspergillus oryzae

Secondary metabolite as therapeutic agent from endophytic fungi Alternaria longipes strain VITN14G of mangrove plant Avicennia officinalis

Carotane sesquiterpenoids A–G from the desert endophytic fungus Fusarium sp. HM 166

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