New phenylpyridone derivatives from the Penicillium sumatrense GZWMJZ-313, a fungal endophyte of Garcinia multiflora

Xu, Ya‐Qiong; Wang, Liping; Zhu, Guoliang; Zuo, Mingxing; Gong, Qianhong; He, Wenwen; Li, Mingpeng; Yuan, Chun‐Mao; Hao, Xiao‐Jiang; Zhu, Weiming

doi:10.1016/j.cclet.2018.08.015

Cited by 23 publications

(23 citation statements)

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“…The HMBC correlations from H-10 to C-8, H-7 to C-9, C-8a and C-5 along with the 1 H- 1 H COSY fragment of H-10/H-11/H-12/H-13/H-14 collectively pointed to the existence of the key phenylpyridone core. The comparison of the NMR spectroscopic profiles of compound 4 with those of citridone E [5], which was previously confirmed by single crystal X-ray diffraction, revealed close structure similarities with regard to the 6-6/6 ring systems and substituent patterns. The only difference was attributable to the trans double bond at C-3 and C-4 positions in 4 which was replaced by a carboxyl functional moiety in citridone E. This deduction was further confirmed by the chemical shifts of C-2′ [ δ C 133.9] and C-3′ [ δ C 126.2, δ H 5.61 (1H, q, J = 6.2 Hz,)] in conjunction with key HMBC correlations from the H 3 -1′ to C-2 and C-3′, H 3 -4′ to C-2′ and C-3′.…”

Section: Resultssupporting

confidence: 55%

“…However, the potential spontaneous retro 6π electrocyclization/6π electrocyclization cascaded reaction tended to make them as an unseparated enantiomers (as shown in Scheme 1). By comparing the 13 C NMR data of citridone E and citridone F in the literature [5], it was confirmed that the double bond at positions C-2′ of compound 4 was the E configuration. In order to unravel their absolute structures, efforts toward conclusive evidence by comparison of the experimental and calculated circular dichroism (CD) spectra using the time-dependent DFT were performed.…”

Section: Resultsmentioning

confidence: 93%

“…Pyridone analogues, a family of naturally occurring alkaloids, discovered from a variety of fungal sources have displayed a wide spectrum of fascinating biological activities, including cytotoxic [1,2], antibacterial [3,4,5] and antifungal [6,7] pharmacological actions, which has attracted broad attention from synthetic chemists and pharmacological communities in their search for discovering pharmaceutical drugs [8,9,10,11,12,13]. Regarding the known pyridine alkaloids, citridone A was first discovered as a potentiator for miconazole against Candida albicans with a unique 6-6/5/5-ring system containing a rare phenyl- R -furopyridone skeleton [6].…”

Section: Introductionmentioning

confidence: 99%

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Tersone A-G, New Pyridone Alkaloids from the Deep-Sea Fungus Phomopsis tersa

et al. 2019

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Four phenylfuropyridone racemates, (±)-tersones A-C and E (1–3, 5), one phenylpyridone racemate, (±)-tersone D (4), one new pyridine alkaloid, tersone F (6), single new phenylfuropyridone, tersone G (7) and two known analogs 8 and 9 were isolated from the deep-sea fungus Phomopsis tersa. Their structures and absolute configurations were characterized on the basis of comprehensive spectroscopic analyses, single-crystal X-ray diffraction experiments, and electronic circular dichroism (ECD) calculations. Moreover, compounds 1–9 were evaluated for in vitro antimicrobial and cytotoxic activity. Compounds 5b and 8b exhibited antibacterial activity against S. aureus with the MIC value of 31.5 μg/mL, while compound 5b showed cytoxic activities against SF-268, MCF-7, HepG-2 and A549 cell lines with IC50 values of 32.0, 29.5, 39.5 and 33.2 μM, respectively.

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Section: Resultssupporting

confidence: 55%

Section: Resultsmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

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Tersone A-G, New Pyridone Alkaloids from the Deep-Sea Fungus Phomopsis tersa

et al. 2019

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“…Extrolites : Penicillium sumatraense produces curvularins such as curvularin, dehydrocurvularin, sumalactone A-D, sumalarins and citridones E-G ( Vesonder et al., 1976 , Malmstrom et al., 2000 , Meng et al., 2013 , de Castro et al., 2016 , Ha et al., 2017 , Wu et al., 2017 , Xu et al., 2019b ). This species has been reported to produce a blue mould rot of Vitus vinifera and Sparassis crispa ( Mahdian and Zafari, 2016 , Liu et al., 2018b ).…”

Section: Resultsmentioning

confidence: 99%

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Houbraken¹,

Kocsubé²,

Visagie³

et al. 2020

Studies in Mycology

406

458

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The Eurotiales is a relatively large order of Ascomycetes with members frequently having positive and negative impact on human activities. Species within this order gain attention from various research fields such as food, indoor and medical mycology and biotechnology. In this article we give an overview of families and genera present in the Eurotiales and introduce an updated subgeneric, sectional and series classification for Aspergillus and Penicillium . Finally, a comprehensive list of accepted species in the Eurotiales is given. The classification of the Eurotiales at family and genus level is traditionally based on phenotypic characters, and this classification has since been challenged using sequence-based approaches. Here, we re-evaluated the relationships between families and genera of the Eurotiales using a nine-gene sequence dataset. Based on this analysis, the new family Penicillaginaceae is introduced and four known families are accepted: Aspergillaceae , Elaphomycetaceae , Thermoascaceae and Trichocomaceae . The Eurotiales includes 28 genera: 15 genera are accommodated in the Aspergillaceae ( Aspergillago , Aspergillus , Evansstolkia , Hamigera , Leiothecium , Monascus , Penicilliopsis , Penicillium , Phialomyces , Pseudohamigera , Pseudopenicillium , Sclerocleista , Warcupiella , Xerochrysium and Xeromyces ), eight in the Trichocomaceae ( Acidotalaromyces , Ascospirella , Dendrosphaera , Rasamsonia , Sagenomella , Talaromyces , Thermomyces , Trichocoma ), two in the Thermoascaceae ( Paecilomyces , Thermoascus ) and one in the Penicillaginaceae ( Penicillago ). The classification of the Elaphomycetaceae was not part of this study, but according to literature two genera are present in this family ( Elaphomyces and Pseudotulostoma ). The use of an infrageneric classification system has a long tradition in Aspergillus and Penicillium . Most recent taxonomic studies focused on the sectional l...

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“…Compound 8 was recently isolated as (AE)-citridone E from Penicillium sumatrense GZWMJZ-313, and was characterized by X-ray diffraction and electronic circular dichroism (ECD). [16] We propose 8 is formed through the non-enzymatic 1,4-conjugated addition between the C4-hydroxyl and C9-olefin of 6 (for a similar example of fused pyran formation at the tetramic acid stage, see ref. [17]).…”

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confidence: 99%

Concise Biosynthesis of Phenylfuropyridones in Fungi

et al. 2020

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Phenylfuropyridone natural products from fungi exhibit a range of antibacterial and cytotoxicity activities, and can potentiate azole antifungal compounds. We elucidated the biosynthetic pathway of compounds in the citridone family through heterologous reconstitution of the pfp pathway. We demonstrate that multiple members of this family can be accessed from a reactive ortho-quinone methide (o-QM) intermediate through electrocyclization, cycloisomerization, or conjugate addition. Formation of the quaternary carbon center in citridone B is catalyzed by an epoxide-forming P450 enzyme, followed by carbon skeletal rearrangement. Our results showcase how nature harvests the reactivities of an o-QM intermediate to biosynthesize complex natural products.

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New phenylpyridone derivatives from the Penicillium sumatrense GZWMJZ-313, a fungal endophyte of Garcinia multiflora

Cited by 23 publications

References 13 publications

Tersone A-G, New Pyridone Alkaloids from the Deep-Sea Fungus Phomopsis tersa

Tersone A-G, New Pyridone Alkaloids from the Deep-Sea Fungus Phomopsis tersa

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Concise Biosynthesis of Phenylfuropyridones in Fungi

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