Dahurelmusin A, a Hybrid Peptide–Polyketide from <i>Elymus dahuricus</i> Infected by the <i>Epichloë bromicola</i> Endophyte

Song, Qiu‐Yan; Yu, Hongwei; Zhang, Xingxu; Zhang, Nan; Gao, Kun

doi:10.1021/acs.orglett.6b03568

Cited by 8 publications

(6 citation statements)

References 8 publications

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“…avenae, and R. padi were evaluated by a leaf-dip method . The assay was repeated in an air-conditioned room at 25 ± 2 °C.…”

Section: Methodsmentioning

confidence: 99%

“…The insecticidal activities of compounds 1−6 against L. erysimi, A. craccivora, S. avenae, and R. padi were evaluated by a leaf-dip method. 25 The assay was repeated in an air-conditioned room at 25 ± 2 °C. Each tested sample was dissolved in acetone at a concentration of 10 000 μg/mL and diluted with distilled water containing 0.1% Tween-80 to obtain a required concentration.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Echingridimer A, an Oxaspiro Dimeric Sesquiterpenoid with a 6/6/5/6/6 Fused Ring System from Echinops grijsii and Aphicidal Activity Evaluation

Liu

Jiang

et al. 2019

J. Org. Chem.

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A new dimeric eudesmane sesquiterpenoid with an unreported 6/6/5/6/6 fused carbon skeleton, echingridimer A (1), and five monomers (2–6), including two new compounds (2 and 3), were isolated from the roots of Echinops grijsii. Their structures and absolute configurations were elucidated by comprehensive spectroscopic analyses and confirmed by X-ray crystallography or electronic circular dichroism spectra. Compound 1 represents the first example of a 3,15′-linked Michael-type adduct of two eudesmanes, which feature a unique 1-oxaspiro[4.5]decan moiety. The plausible biogenetic pathway for 1–6 was briefly discussed. The oxaspiro dimer (1) not only showed stronger aphicidal activity than closely related monomeric compounds (2–6) and the commercial aphicide pymetrozine but also exhibited remarkable insecticide activity against a broad range of aphids, thus could be used as a potential biobased insecticide to suppress aphids.

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“…avenae, and R. padi were evaluated by a leaf-dip method . The assay was repeated in an air-conditioned room at 25 ± 2 °C.…”

Section: Methodsmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Echingridimer A, an Oxaspiro Dimeric Sesquiterpenoid with a 6/6/5/6/6 Fused Ring System from Echinops grijsii and Aphicidal Activity Evaluation

Liu

Jiang

et al. 2019

J. Org. Chem.

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“…71 A novel hybrid peptide− polyketide, dahurelmusin A (88), was first isolated from E. dahuricus infected by E. bromicola endophyte. 75 Dahurelmusin A possesses a 5-hydroxy-2,2,4,6-tetramethyl-3-oxooctanoic acid residue and a novel 5-hydroxy-2,2,4,6-tetramethyl-3-oxooctanoic acid unit. This type of hybrid peptide−polyketide is derived from microorganisms.…”

Section: Secondary Metabolitesmentioning

confidence: 99%

“…dahuricus infected by E. bromicola endophyte . Dahurelmusin A possesses a 5-hydroxy-2,2,4,6-tetramethyl-3-oxooctanoic acid residue and a novel 5-hydroxy-2,2,4,6-tetramethyl-3-oxooctanoic acid unit.…”

Section: Secondary Metabolitesmentioning

confidence: 99%

Do Epichloë Endophytes and Their Grass Symbiosis Only Produce Toxic Alkaloids to Insects and Livestock?

Song

Nan

et al. 2020

J. Agric. Food Chem.

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Epichloë endophytes in forage grasses have attracted widespread attention and interest of chemistry researchers as a result of the various unique chemical structures and interesting biological activities of their secondary metabolites. This review describes the diversity of unique chemical structures of taxa from Epichloë endophytes and grass infected with Epichloë endophytes and demonstrates their reported biological activities. Until now, nearly 160 secondary metabolites (alkaloids, peptides, indole derivatives, pyrimidines, sesquiterpenoids, flavonoids, phenol and phenolic acid derivatives, aliphatic metabolites, sterols, amines and amides, and others) have been reported from Epichloë endophytes and grass infected with Epichloë endophytes. Among these, non-alkaloids account for half of the population of total metabolites, indicating that they also play an important role in Epichloë endophytes and grass infected with Epichloë endophytes. Also, a diverse array of secondary metabolites isolated from Epichloë endophytes and symbionts is a rich source for developing new pesticides and drugs. Bioassays disclose that, in addition to toxic alkaloids, the other metabolites isolated from Epichloë endophytes and symbionts have notable biological activities, such as antifungal, anti-insect, and phytotoxic activities. Accordingly, the biological functions of non-alkaloids should not be neglected in the future investigation of Epichloë endophytes and symbionts.

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“…The unique macrocyclic structure of stereocalpin A consists of an unprecedented polyketide part (5-hydroxy-2,4-dimethyl-3-oxooctanoic acid, HDMOO) and a Phe-MePhe dipeptide segment. This 12-membered hybrid peptide-polyketide scaffold is shared with several natural products such as taumycins A and B, tausalarin C, and dahurelmusin A, which have been identified. The polyketide substructure of these macrocycles contains the α-unsubstituted or α,α-disubstituted β-keto carboxamide moiety, whereas stereocalpin A solely possesses a potentially labile α-methyl β-keto carboxamide, in which the 2-methyl group in 1a could be subjected to configuration change and be converted into the 2- epi form 1b via the enol (enolate) forms E1 and/or E2 during synthetic and/or purification processes (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis and Stereochemical Revision of Stereocalpin A: Mirror-Image Approach for Stereochemical Assignments of the Peptide–Polyketide Macrocycle

et al. 2018

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Stereocalpin A is a cyclic depsipeptide with cytotoxic activity isolated from the Antarctic lichen Stereocaulon alpinum. Although a number of synthetic investigations of the unprecedented 12-membered macrocycle of stereocalpin A with a dipeptide segment and a polyketide substructure have been conducted, the configurational assignment has not been completed. In this study, we achieved the first total synthesis and stereochemical revision of stereocalpin A. To facilitate the comprehensive assessment of eight possible stereocalpin A isomers, four stereoisomers of polyketide precursors were conjugated with l-Phe-l-MePhe and d-Phe-d-MePhe dipeptides (MePhe: N-methylphenylalanine) to provide four possible isomers and four mirror-image structures of the remaining isomers, respectively. The comparative NMR analysis of a series of stereoisomers revealed that stereocalpin A possesses 2 R,4 S,5 R-configurations, which is unique among the related 12-membered hybrid peptide-polyketide natural products reported recently. The NOE correlations in the polyketide substructure of stereocalpin A were also retrospectively analyzed among the eight possible stereoisomers.

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Dahurelmusin A, a Hybrid Peptide–Polyketide from Elymus dahuricus Infected by the Epichloë bromicola Endophyte

Cited by 8 publications

References 8 publications

Echingridimer A, an Oxaspiro Dimeric Sesquiterpenoid with a 6/6/5/6/6 Fused Ring System from Echinops grijsii and Aphicidal Activity Evaluation

Echingridimer A, an Oxaspiro Dimeric Sesquiterpenoid with a 6/6/5/6/6 Fused Ring System from Echinops grijsii and Aphicidal Activity Evaluation

Do Epichloë Endophytes and Their Grass Symbiosis Only Produce Toxic Alkaloids to Insects and Livestock?

Total Synthesis and Stereochemical Revision of Stereocalpin A: Mirror-Image Approach for Stereochemical Assignments of the Peptide–Polyketide Macrocycle

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