A Botryane Metabolite with a New Hexacyclic Skeleton from an Entomogenous Fungus <i>Hypocrea</i> sp.

Yuan, Yunbin; Yu, Feng; Ren, Fengxia; Niu, Shubin; Liu, Xingzhong; Che, Yongsheng

doi:10.1021/ol402953k

Cited by 31 publications

(30 citation statements)

References 24 publications

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“…The absolute configurations for C-16, C-26, and C-24 were deduced by comparison of the experimental CD spectrum of 4 with the simulated ECD spectra for the 16S,24S,26R (4Aa) and 16R,24R,26S (4Ab) enantiomers of the simplified structure 4A (Figures 5 and S41). 4,6,7,8,9,12 59.0, CH 1.75,d (10.9) 1,3,4,6,7,8,9,12 58.8,CH 1.82,d (10.5) 1,4,6,7,8,9,12 6 46 . 5,6,8,12,13,14,15 49.9,CH 2 2.19,d (11.2) 5,6,8,12,13,14,15 7b 1.15,d (11.6) 5,6,8,9,13,14 1.07,d (10.3) 5, 6, 8, 9, 13, 14 1...…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Full-scan spectra were acquired over a scan range of m/z 100−1000 at 1.03 spectra/s. HPLC separations were performed on an 1.40,dd (11.1,2.9) 2,8,9,10,11 2 34.7,CH 1.77,m 1,3,4,10,11 3a 40.8, CH 2 1.83,ddd (12.2,3.4,3.4) 1,2,4,5,11 3b 1.12,dd (12.2,10.7) 1,2,4,5,11 4 73.4,CH 5.12,ddd (11.0,10.7,3.4) 2,3,5,6,31 5 58.8,CH 1.80,d (11.0) 3,4,6,7,8,9,12,13 6 46.6, qC 7a 50.4, CH 2 2.30, d (11.5) 6, 8, 12, 13, 14, 15 7b 1.24, d (11.5) 5, 6, 8, 9, 13, 14, 15 8 58 . The isolate was identified based on morphology and sequence (GenBank accession no. KF724627) analysis of the ITS region of the rDNA.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…(EC1-35), isolated from a Septobasidiuminfected Serrataspis sp., was chemically investigated, leading to the discovery of hypocrolide A, the first botrydiol−coumarin hybrid compound possessing a unique 5/6/6/5/6/6 skeleton. 6 Since the HPLC fingerprint of the crude extract showed the presence of other minor, active components that could not be identified due to sample limitations, the fungus was refermented on a larger scale using the same solid fermentation culture technique from which hypocrolide A was first isolated. The resulting EtOAc extract showed significant inhibitory effects on the proliferation of four human tumor cell lines, HeLa (cervical carcinoma), HCT116 (colorectal carcinoma), A549 (lung adenocarcinoma), and MCF-7 (breast cancer).…”

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confidence: 99%

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Hypocriols A–F, Heterodimeric Botryane Ethers from Hypocrea sp., an Insect-Associated Fungus

Ren¹,

Zhu²,

Wang³

et al. 2016

J. Nat. Prod.

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The new heterodimeric botryane ethers hypocriols A-F (1-6) and the known compounds 4β-acetoxy-9β,10β,15α-trihydroxyprobotrydial (7), dihydrobotrydial (8), 10-oxodehydrodihydrobotrydial (9), and dehydrobotrydienol (10) were isolated from the solid cultures of an insect-associated fungus Hypocrea sp. The structures of 1-6 were elucidated primarily by NMR experiments. The absolute configuration of 1 was assigned using the modified Mosher method and electronic circular dichroism (ECD) calculations, whereas those for 3-5, and 2 and 6 were deduced via ECD calculations and circular dichroism data, respectively. Compounds 1-6 appear to be the first heterodimeric botryane ethers and showed antiproliferative effects against a small panel of four human tumor cell lines.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

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confidence: 99%

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Hypocriols A–F, Heterodimeric Botryane Ethers from Hypocrea sp., an Insect-Associated Fungus

Ren¹,

Zhu²,

Wang³

et al. 2016

J. Nat. Prod.

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“…Many derivatives are known to have phytotoxic effects and therefore are regarded as pathogenicity factors (Deighton et al, 2001). Meanwhile, similar metabolites were obtained from the genera Hypocrea (an ascospore isolate of a wood-degrading member of the Hypocreaceae; see Yuan et al, 2013), as well as from the xylariaceous genera Geniculosporium (an endophyte, see Krohn et al, 2005) and a strain of an ascospore-derived isolate of Daldinia (Qin et al, 2008). None of these genera is regarded to be pathogenic, even though the Xylariaceae have sometimes been reported to cause disease symptoms in stressed and weakened host plants.…”

Section: Resultsmentioning

confidence: 99%

Botryane, noreudesmane and abietane terpenoids from the ascomycete Hypoxylon rickii

et al. 2015

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In the course of our screening for new bioactive natural products, a culture of Hypoxylon rickii, a xylariaceous ascomycete collected from the Caribbean island Martinique, was identified as extraordinary prolific producer of secondary metabolites. Ten metabolites of terpenoid origin were isolated from submerged cultures of this species by preparative HPLC. Their structures were elucidated using spectral techniques including 2D NMR and HRESIMS. Three of the compounds were elucidated as new botryanes (1-3) along with three known ones, i.e. (3aS)-3a,5,5,8-tetramethyl-3,3a,4,5-tetrahydro-1H-cyclopenta[de]isochromen-1-one (4), (3aS,8R)-3a,5,5,8-tetramethyl-3,3a,4,5,7,8-hexahydro-1H-cyclopenta[de]isochromen-1-one (5) and botryenanol (6). Further three new sesquiterpenoids featured a 14-noreudesmane-type skeleton and were named hypoxylan A-C (7-9); the diterpenoid rickitin A (10) contains an abietane-type backbone. Compounds 1, 2, 3, 7, and 10 showed cytotoxic effects against murine cells.

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“…and cytotoxic activities [5]. Even though sesquiterpenes form the largest group of terpenes and include commercially important compounds, they are difficult to chemically synthesize because of the complex structure that often leads to low yield [6].…”

Section: -2506mentioning

confidence: 99%

ISOLATION OF TWO BOTRYANES FROM Hypoxylon rickii AND IDENTIFICATION OF THE ENCODING GENES

Alwi

Rosandy

Bakar³

et al. 2017

MJAS

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10-oxodehydrobotrydial (1) and 4β-Acetoxy-9β,10β,15α-trihydroxyprobotrydial (2) have been isolated from Hypoxylon rickii mycelia extract. Compound 2 is probably an intermediate of botrydial, which is a known sesquiterpene phytotoxin. Cluster Omega and Artemis software analysis suggested that HRT6, a possible botrydial-like gene cluster with four genes shows more than 50% similarities compared to Botrytis cinerea botrydial gene cluster, BcBOT. A comparison between proposed 4β-Acetoxy-9β,10β,15α-trihydroxyprobotrydial (2) producing pathway and BcBOT proposed pathway shows compatible function of each gene prediction. Further confirmation using RNA gene knock-outs is on-going. Keywords:Hypoxylon rickii, botryane, terpene synthase Abstrak 10-oksodehidrobotridial (1) dan 4β-Asetoksi-9β,10β,15α-trihidroksiprobotridial (2) telah dipencilkan dari ekstrak miselia Hypoxylon rickii. Sebatian 2 dijangkakan sebagai sebatian perantara dalam pembentukkan botridial iaitu sejenis fitotoksin sesquiterpena. Penggunaan dua perisian Cluster Omega dan Artemis telah berjaya mengenalpasti gen kelompok yang berkemungkinan dari H. rickii sebagai HRT6 dengan empat gen menunjukkan persamaan lebih daripada 50% berbanding gen kelompok Botrytis cinerea, BcBOT. Perbandingan antara dengan cadangan laluan biosintesis 4β-Asetoksi-9β,10β,15α-trihidroksiprobotridial (2) dengan BcBOT menunjukkan persamaan fungsi -fungsi gen. Pengesahan lanjut menggunakan RNA (mendiamkan gen) sedang dijalankan.

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A Botryane Metabolite with a New Hexacyclic Skeleton from an Entomogenous Fungus Hypocrea sp.

Cited by 31 publications

References 24 publications

Hypocriols A–F, Heterodimeric Botryane Ethers from Hypocrea sp., an Insect-Associated Fungus

Hypocriols A–F, Heterodimeric Botryane Ethers from Hypocrea sp., an Insect-Associated Fungus

Botryane, noreudesmane and abietane terpenoids from the ascomycete Hypoxylon rickii

ISOLATION OF TWO BOTRYANES FROM Hypoxylon rickii AND IDENTIFICATION OF THE ENCODING GENES

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