Cytotoxic polyketides from endophytic fungus Phoma bellidis harbored in Ttricyrtis maculate

The creeping weed, Chrysopogon aciculatus (Retz.) Trin., is widely known for its use as folk medicine, while its phytotoxic potential has not been examined. Therefore, we carried out an investigation into the phytotoxic potential of C. aciculatus to identify phytotoxic substances. C. aciculatus extracts showed inhibitory effects on shoot and root growth of cress, lettuce, rapeseed, and Italian ryegrass. Inhibition was both species-dependent and concentration-dependent. Two substances, (9S,10E,12Z)-9-hydroxyoctadeca-10,12-dienoic acid (9-HO-ODDEA) and rhizopycnin A, were isolated using chromatographies and characterized by spectral analysis. 9-HO-ODDEA retarded shoot and root growth of cress at concentrations higher than 1.0 and 0.3 mM, respectively, while on cress seedling by rhizopycnin A, the inhibition began from 1.0 mM. The concentrations needed for 50% inhibition of the shoot and root growth of test plants ranged from 1.71-2.31, and 0.71-0.72 mM for 9-HO-ODDEA and rhizopycnin A, respectively. These results indicate that these substances may contribute, to a certain extent, to the phytotoxic activity of C. aciculatus.

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“…; Wang et al . ). In the study, therefore, rhizopycnin A may be produced from the endophytic fungus obtained from the extract of C. aciculatus.…”

Section: Discussionmentioning

confidence: 97%

Phytotoxic potential of Chrysopogon aciculatus (Retz.) Trin. (Poaceae)

Islam

Zaman

Iwasaki

et al. 2019

Weed Biology and Management

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“…In line, using NMR spectroscopy very recently, four new polyketides, particularly bellidisin A (Fig. 11.1a) and bellidisins B-D, were isolated from Phoma bellidis (Wang et al 2019). The absolute configurations and structures of these polyketides were determined by 1D and 2D NMR.…”

Section: Bioanalytical Techniques To Determine Secondary Metabolites Of Phoma Speciesmentioning

confidence: 84%

“…The absolute configurations and structures of these polyketides were determined by 1D and 2D NMR. In their investigation, they noticed that bellidisin D exhibited stronger cytotoxicity against human cancer cell lines HL-60, A549, SMMC-7721, MCF-7, and SW480 in comparison to cisplatin-a standard cytotoxic drug (Wang et al 2019). In the same year, Liu et al (2019) also reported phomanolide (Fig.…”

Section: Bioanalytical Techniques To Determine Secondary Metabolites Of Phoma Speciesmentioning

confidence: 99%

Bioactive Secondary Metabolites from Endophytic Phoma spp.

Mahish¹,

Singh²,

Chauhan

2021

Phoma: Diversity, Taxonomy, Bioactivities, and Nanotechnology

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“…There are related natural products that possess this fragment in their structures, for example recently isolated ten-membered lactone from sponge-associated fungus Xylaria feejeenisis [43], diaportheolides A and B from Diaporthe sp. SXZ-19 [44] and others [45,46] (Figure 4). Unfortunately, none of these compounds were tested for phytotoxic activity.…”

Section: Discussionmentioning

confidence: 96%

Structure–Activity Relationship of Phytotoxic Natural 10-Membered Lactones and Their Semisynthetic Derivatives

Dalinova

Fedorov

Dubovik

et al. 2021

JoF

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Ten-membered lactones (nonenolides) demonstrate phytotoxic, antimicrobial, and fungicidal activity promising for the development of natural product-derived pesticides. The fungus Stagonospora cirsii is able to produce phytotoxic stagonolides A (1), J (2), K (3) and herbarumin I (4) with high yield. The aim of this study was to create a set of structurally related nonenolides and to reveal the structural features that affect their biological activity. Stagonolide A (1) and C-7 oxidized stagonolide K (11) showed the highest phytotoxicity in leaf puncture assay and agar seedlings assay. The oxidation of C-7 hydroxyl group (as in 1, acetylstagonolide A (10) and (11) led to the manifestation of toxicity to microalgae, Bacillus subtilis and Sf9 cells regardless of the configuration of C-9 propyl chains (R in 1 and 10, S in 11). C-7 non-oxidized nonenolides displayed none or little non-target activity. Notably, 7S compounds were more phytotoxic than their 7R analogues. Due to the high inhibitory activity against seedling growth and the lack of side toxicity, mono- and bis(acetyl)- derivatives of herbarumin I were shown to be potent for the development of pre-emergent herbicides. The identified structural features can be used for the rational design of new herbicides.

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Cytotoxic polyketides from endophytic fungus Phoma bellidis harbored in Ttricyrtis maculate

Cited by 26 publications

References 21 publications

Phytotoxic potential of Chrysopogon aciculatus (Retz.) Trin. (Poaceae)

Phytotoxic potential of Chrysopogon aciculatus (Retz.) Trin. (Poaceae)

Bioactive Secondary Metabolites from Endophytic Phoma spp.

Structure–Activity Relationship of Phytotoxic Natural 10-Membered Lactones and Their Semisynthetic Derivatives

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