Diphenyl ethers from Aspergillus sp. and their anti-Aβ42 aggregation activities

Zhao, Huan; Wang, Gao-Qian; Tong, Xupeng; Chen, Guodong; Huang, Yuan-Fan; Cui, Jia-Yu; Kong, Ming-Zhu; Guo, Liangdong; Zheng, Youliang; Yao, Xin‐Sheng; Gao, Hao

doi:10.1016/j.fitote.2014.07.007

Cited by 40 publications

(20 citation statements)

References 30 publications

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“…The 1 H and 13 C NMR spectroscopic data of 1 (Table 1) agreed with those of isolated N-0532A (8), 17 except that the double bond at C-3′ was saturated by a proton at C-3′ The 1 H and 13 C NMR spectroscopic data of 2 (Table 1) were similar to those of 1, except that the resonance of methyl protons of the acetoxy group at C-4′ of 2 (δ 1.69) appeared at a higher field than that of 1 (δ 2.11). The coupling constants between H-1′ and H-2′ (J = 6.0 Hz) and the NOESY correlations of the two protons of 1 and 2 revealed a cis ring fusion, the same as in the sterigmatocystin ( 5), 18,20,21 which allowed assignment of the absolute configurations at both C-1′ and C-2′ as S. The assignment of configurations at C-4′ of 1 and 2 as R and S were determined by comparing the 1 H NMR resonances of an acetoxy group to those reported for related analogues, dothistromin pentaacetate 22 and oxisterigmatocystin D. 23 The methyl protons of the 4′-acetoxy group of 2 appeared at a higher field (δ H 1.69) than in 1 (δ H 2.11), agreeing with that reported for endo dothistromin pentaacetate (δ H 1.67), 22 which was due to the strong shielding effect of xanthone (Figure 3). On the other hand, the 4′-acetoxy group of 1 showed a resonance at δ H 2.11, suggesting the exo arrangement (Figure 3), which corresponds to that of oxisterigmatocystin D (δ H 2.07).…”

Section: ■ Results and Discussionmentioning

confidence: 88%

Mycotoxins from the Fungus Botryotrichum piluliferum

Rajachan

Kanokmedhakul

Soytong³

et al. 2017

J. Agric. Food Chem.

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Two new sterigmatocystin derivatives, oxisterigmatocystins E and F (1 and 2, respectively), along with nine known compounds, oxisterigmatocystins G and H (3 and 4, respectively), sterigmatocystin (5), N-0532B (6), O-methylsterigmatocystin (7), N-0532A (8), 6-O-methylversicolorin A (9), 6,8-O-dimethylversicolorin A (10), and 8-O-methylaverufin (11), were isolated from the fungus Botryotrichum piluliferum. The structures of these mycotoxins were elucidated by spectroscopic evidence. Among these, compounds 3, 4, and 9 were discovered as natural products for the first time. Compounds 1, 3, and 4 displayed antimalarial activity toward Plasmodium falciparum (IC = 7.9-23.9 μM). In addition, compounds 1-6 and 8-11 exhibited cytotoxicity against KB, MCF-7, and NCI-H187 cell lines (IC = 0.38-78.6 μM). However, compounds 1-9 showed cytotoxic effects against the Vero cell line (IC = 0.65-12.3 μM). This finding should promote awareness of the contamination of B. piluliferum in the food chain and agricultural soil.

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Section: ■ Results and Discussionmentioning

confidence: 88%

Mycotoxins from the Fungus Botryotrichum piluliferum

Rajachan

Kanokmedhakul

Soytong³

et al. 2017

J. Agric. Food Chem.

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“…Besides the new compounds, ( S )-diorcinol B ( 3 ) [ 2 ], 9-acetyldiorcinol B ( 4 ) [ 14 ], diorcinol C ( 5 ) [ 2 ], diorcinol D ( 6 ) [ 2 ], diorcinol E ( 7 ) [ 2 ], diorcinol J ( 8 ) [ 15 ], and a dihydrobenzofuran derivative, 3-(2-(1-hydroxy-1-methyl-ethyl)-6-methyl-2,3-dihydrobenzofuran-4-yloxy)-5-methylphenol ( 9 ) [ 16 ] were also isolated from this fungus. Their structures were elucidated by spectroscopy and by comparison with previously reported data.…”

Section: Resultsmentioning

confidence: 99%

Prenylated Diphenyl Ethers from the Marine Algal-Derived Endophytic Fungus Aspergillus tennesseensis

Wang

Ren

et al. 2018

Molecules

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Considerable attention has been paid to marine derived endophytic fungi, owing to their capacity to produce novel secondary metabolites with potent bioactivities. In this study, two new compounds with a prenylated diphenyl ether structure—diorcinol L (1) and (R)-diorcinol B (2)—were isolated from the marine algal-derived endophytic fungus Aspergillus tennesseensis, along with seven known compounds: (S)-diorcinol B (3), 9-acetyldiorcinol B (4), diorcinol C (5), diorcinol D (6), diorcinol E (7), diorcinol J (8), and a dihydrobenzofuran derivative 9. Their structures were elucidated by extensive NMR spectroscopy studies. Compound 2 represents the first example of an R-configuration in the prenylated moiety. All these isolated compounds were examined for antimicrobial and cytotoxic activities. Compounds 1–9 exhibited antimicrobial activities against some human- and plant-pathogenic microbes with MIC values ranging from 2 to 64 μg/mL. Moreover, compound 9 displayed considerable inhibitory activity against the THP-1 cell line in vitro, with an IC50 value of 7.0 μg/mL.

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“…Our simple search strategy is illustrated in Figure 1. Our study resulted in the identification of varied bioactivities of ELF, and included but not limited to antibacterial [37,[44][45][46], antifungal [47][48][49][50], antioxidant [35,[51][52][53][54], cytotoxic [43,[55][56][57][58][59], anti-inflammatory [60][61][62], anti-Alzheimer's disease [63,64], antiviral [65], and anti-biofilm [66][67][68] (Figure 2, Table 1). From these studies, a total of 592 compounds was reported, with half of these metabolites identified as novel (Figure 3).…”

Section: Endolichenic Fungi (Elf) and Their Role In The Lichen Symbiosismentioning

confidence: 99%

In pursuit of promising microbes for drug discovery: tapping endolichenic fungi (ELF) from lichens

Cruz¹,

Santiago²

2021

actamanil

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The emergence of novel and re-emergence of latent infectious diseases coupled with rising cases of antimicrobial resistance necessitates the continuous search for new antibiotics. The Kingdom Fungi has been at the centerpiece of any drug discovery program ever since the beginning of the antibiotic era.The key strategy is to find novel taxa and/or ecologically defined fungal groups for the screening of bioactive secondary metabolites. In this paper, we presented the endolichenic fungi as promising fungi for bioprospecting. We searched for published papers on these fungi and presented reports of their biological activities. Through this paper, we hope to increase interest on these microorganisms among natural product researchers.

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Diphenyl ethers from Aspergillus sp. and their anti-Aβ42 aggregation activities

Cited by 40 publications

References 30 publications

Mycotoxins from the Fungus Botryotrichum piluliferum

Mycotoxins from the Fungus Botryotrichum piluliferum

Prenylated Diphenyl Ethers from the Marine Algal-Derived Endophytic Fungus Aspergillus tennesseensis

In pursuit of promising microbes for drug discovery: tapping endolichenic fungi (ELF) from lichens

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