Identification of a Unique Azaphilone Produced by <i>Chaetomium globosum</i> Isolated from <i>Polygonatum sibiricum</i>

Song, Chunyan; Ding, Gang; Wu, Gang; Yang, Jian; Zhang, Mingzhe; Wang, Haoyu; Wei, Dongsheng; Qin, Jianchun; Guo, Lan-Ping

doi:10.1002/cbdv.201900744

Cited by 15 publications

(14 citation statements)

References 21 publications

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“…The authors also claim that 3,7-dimethyl-2,6-octadienyl group attached to N-2 contributed to the potent cytotoxic activities against MGC803 and AGS gastric cancer cell lines what can induce new investigations with semisynthetic azaphilone derivatives possessing this group [11]. The azaphilones (39) and (40) showed moderate activity against leukemia HL-60 and human breast cancer. However, (39) exhibited potent apoptosis induction activity by mediating caspase-3 activation and PARP degradation at 3 µM in leukemic cells HL-60 [44].…”

Section: Biological Activities Of Azaphilonesmentioning

confidence: 97%

“…NA-S01-R1 with the same planar structure of 25 but with different stereochemistry, suggesting that its structure should be revised [ 38 ]. Two months after the report of chaephilone C ( 25 ), a new chlorinated azaphilone from C. globosum , endophytic of Polygonatum sibiricum , was reported and also called chaephilone C ( 27 ) [ 39 ]. However, this latter compound displayed a chemical structure similar to ( 26 ), but completely different from the former ( 25 ).…”

Section: Chemistry Biological Activities and Biosynthetic Pathways Of Recently (2020–2021) Reported Azaphilonesmentioning

confidence: 99%

“… Chemical structures of Chaetomium azaphilones: 25 : Chaephilone C (1R,7S,8R,8aR,9E,11S,4′R,5′R); 26 : chaephilone D; 27 : chaephilone C*; 28 : cochliodone J; 29 : N-(3,7-Dimethyl-2,6-octadienyl)-2-aza-2-deoxychaetoviridin A; 30 : 4′-epi-N-(3,7-Dimethyl-2,6-octadienyl)-2-aza-2-deoxychaetoviridin A; 31 : N-(3-Methyl-2-butenyl)-2-aza-2-deoxychaetoviridin A, 32 : 4′-epi-N-(3-Methyl-2-butenyl)-2-aza-2-deoxychaetoviridin A; 33 : N-(3,7-Dimethyl-2,6-octadienyl)-2-aza-2-deoxychaetoviridin E; 34 : N-(3-Methyl-2-butenyl)-2-aza-2-deoxychaetoviridin E; 35: 4′,5′-dinor-5′-Deoxy-N-(3,7-dimethyl-2,6-octadienyl)-2-aza-2- deoxychaetoviridin A; 36 : 4′,5′-dinor-5′-Deoxy-N-(3-methyl-2-butenyl)-2-aza-2-deoxy- chaetoviridin A; 37 : seco-chaetomugilin; 38 : chaetolactam A; 39 : 11-epi-chaetomugilide B; 40 : chaetomugilide D; 41 : globusumone [ 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 ]. …”

Section: Figurementioning

confidence: 99%

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Recent Findings in Azaphilone Pigments

Pimenta

Gomes

Cardoso

et al. 2021

JoF

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Filamentous fungi are known to biosynthesize an extraordinary range of azaphilones pigments with structural diversity and advantages over vegetal-derived colored natural products such agile and simple cultivation in the lab, acceptance of low-cost substrates, speed yield improvement, and ease of downstream processing. Modern genetic engineering allows industrial production, providing pigments with higher thermostability, water-solubility, and promising bioactivities combined with ecological functions. This review, covering the literature from 2020 onwards, focuses on the state-of-the-art of azaphilone dyes, the global market scenario, new compounds isolated in the period with respective biological activities, and biosynthetic pathways. Furthermore, we discussed the innovations of azaphilone cultivation and extraction techniques, as well as in yield improvement and scale-up. Potential applications in the food, cosmetic, pharmaceutical, and textile industries were also explored.

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Section: Biological Activities Of Azaphilonesmentioning

confidence: 97%

Section: Chemistry Biological Activities and Biosynthetic Pathways Of Recently (2020–2021) Reported Azaphilonesmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

See 1 more Smart Citation

Recent Findings in Azaphilone Pigments

Pimenta

Gomes

Cardoso

et al. 2021

JoF

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“…(2020) SW1990 11.7 μM PANC-1 9.80 μM (+)-Asperteretone E (111) AsPC-1 9.90 μM SW1990 10.3 μM PANC-1 15.6 μM Hispidulactone F (112) HepG2 61.05 μM Chaetosphaeronema hispidulum (TS-8-1) Dessert plant (T) China Zheng et al. (2020) Azaphilones Chaephilone C (113) HepG2 38.6 μM Chaetomium globosum TY-2 Polygonatum Sibiricum (T) China Song et al. (2020) Isochromophilone A (114) ACHN 27 μM Diaporthe sp.…”

Section: Cytotoxic Secondary Metabolites From Endophytic Fungimentioning

confidence: 99%

“…Chaephilone C (113) is an unprecedented azaphilone, which was obtained from EtOAc extract of endophytic fungi Chaetomium globosum TY-2 isolated from the plant Polygonatum sibiricum . It showed moderate antiproliferative activity towards HepG2 tumor cell line with IC 50 value of 38.6 μM ( Song et al., 2020 ). Isochromophilone A (114), Isochromophilone D (115), Isochromophilone F (116) and Isochromophilone C (117) are cytotoxic chloroazaphilone derivatives, which were separated from the fermented culture of Diaporthe sp.…”

Section: Cytotoxic Secondary Metabolites From Endophytic Fungimentioning

confidence: 99%

Endophytic fungi: A treasure trove of novel anticancer compounds

Prajapati

Goswami

Rawal

2021

Current Research in Pharmacology and Drug Discovery

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Cancer is a multifactorial disease with a convoluted genesis and progression. The emergence of multidrug resistance to presently be offered drug and relapse is by far, the most critical concern to tackle this deteriorating disease. Henceforth, there is undeniably an inflated necessity for safe, promising, and less harmful new anticancer drugs. Natural compounds from various sources like plants, animals, and microorganisms have occupied a center stage in drug discovery due to their tremendous chemical diversity and potential as therapeutic agents. Endophytic microbes are symbiotically associated with plants and have been proven to produce novel or analogues of host bioactive metabolites exhibiting a variety of biological activities including anticancer activity. This review emphasizes on structurally diverse unprecedented anticancer natural compounds that have been reported exclusively from endophytic fungi from 2016 to 2020. It covers chemical nature of metabolites, its fungal source associated with terrestrial, as well as marine plants and anticancer activity based on their cytotoxicity profile against various cancer cell lines. Many of these fungal metabolites with promising anticancer activity can be used as lead molecules for in silico experiments and deserve special attention from scientists for further in vitro and clinical research.

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Key insights into secondary metabolites from various Chaetomium species

Dwibedi

Rath

Jain

et al. 2023

Appl Microbiol Biotechnol

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Endophytic fungi have proved to be a major source of secondary metabolites, wherein the genus Chaetomium has emerged as a source of multifarious bioactive natural compounds belonging to diverse classes such as chaetoglobosins, epipolythiodioxopiperazines, azaphilones, xanthones, anthraquinone, chromones, depsidones, terpenoids, and steroids. The objective of this review is to encapsulate recent findings on various Chaetomium strains, such as C. globosum , C. cupreum , C. elatum , C. subspirale , C. olivaceum , C. indicum , and C. nigricolor known for production of beneficial secondary metabolites, with an insight into their origin and function. A thorough literature survey was conducted for obtaining Chaetomium -derived secondary metabolites, with a scope of future application into drug development efforts. More than 100 secondary metabolites, with various beneficial properties such as antitumor, cytotoxic, antimalarial, and enzyme inhibitory activities, were enlisted. We believe this review will enhance the understanding of beneficial effects conferred by various Chaetomium -derived secondary metabolites and emphasize their potential in serving novel drug development efforts. Key points • Identified Chaetomium - derived metabolites with potential for drug development. • More than 100 beneficial metabolites are enlisted. • Benefits include anti-cancerous, antimalarial, and anti-enzymatic properties . Graphical Abstract

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Identification of a Unique Azaphilone Produced by Chaetomium globosum Isolated from Polygonatum sibiricum

Cited by 15 publications

References 21 publications

Recent Findings in Azaphilone Pigments

Recent Findings in Azaphilone Pigments

Endophytic fungi: A treasure trove of novel anticancer compounds

Key insights into secondary metabolites from various Chaetomium species

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