Multidrug resistance–reversal effects of resin glycosides from Dichondra repens

Song, Wenli; Wang, Wen-Qiong; Zhang, Shuwei; Liu, Xuan

doi:10.1016/j.bmcl.2014.12.083

Cited by 14 publications

(14 citation statements)

References 12 publications

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“…The jalapinolic acid moiety was found to be in an open structure instead of in a macrolactone ring. Previous RGs identified from Dichondra repens were also found to contain two rhamnoses and glucoses (Dichondrin A, B) or two rhamnoses and one glucose (Dichondrin C) [ 18 ], both with open hydroxyacyl chain instead of a macrolactone ring. We thus call this structure Dichondrin D. The MS/MS fragmentation pattern of Dichondrin D could be explained by the characterized structure ( Supplementary Fig.…”

Section: Resultsmentioning

confidence: 99%

Illuminating the lineage-specific diversification of resin glycoside acylsugars in the morning glory (Convolvulaceae) family using computational metabolomics

Kruse

Bennett

Mahood

et al. 2022

Horticulture Research

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Acylsugars are a class of plant defense compounds produced across many distantly related families. Members of the horticulturally important morning glory (Convolvulaceae) family produce a diverse sub-class of acylsugars called resin glycosides (RGs), which comprise oligosaccharide cores, hydroxyacyl chain(s), and decorating aliphatic and aromatic acyl chains. While many RG structures are characterized, the extent of structural diversity of this class in different genera and species is not known. In this study, we asked whether there has been lineage-specific diversification of RG structures in different Convolvulaceae species that may suggest diversification of the underlying biosynthetic pathways. Liquid chromatography coupled with tandem mass spectrometry (LC–MS/MS) was performed from root and leaf extracts of 26 species sampled in a phylogeny-guided manner. LC–MS/MS revealed thousands of peaks with signature RG fragmentation patterns with one species producing over 300 signals, mirroring the diversity in Solanaceae-type acylsugars. A novel RG from Dichondra argentea was characterized using Nuclear Magnetic Resonance spectroscopy, supporting previous observations of RGs with open hydroxyacyl chains instead of closed macrolactone ring structures. Substantial lineage-specific differentiation in utilization of sugars, hydroxyacyl chains, and decorating acyl chains was discovered, especially among Ipomoea and Convolvulus – the two largest genera in Convolvulaceae. Adopting a computational, knowledge-based strategy, we further developed a high-recall workflow that successfully explained ~72% of the MS/MS fragments, predicted the structural components of 11/13 previously characterized RGs, and partially annotated ~45% of the RGs. Overall, this study improves our understanding of phytochemical diversity and lays a foundation for characterizing the evolutionary mechanisms underlying RG diversification.

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Section: Resultsmentioning

confidence: 99%

Illuminating the lineage-specific diversification of resin glycoside acylsugars in the morning glory (Convolvulaceae) family using computational metabolomics

Kruse

Bennett

Mahood

et al. 2022

Horticulture Research

View full text Add to dashboard Cite

show abstract

“…The jalapinolic acid moiety was found to be in an open structure instead of in a macrolactone ring. Previous RGs identified from Dichondra repens were also found to contain two rhamnoses and glucoses (Dichondrin A, B) or two rhamnoses and one glucose (Dichondrin C) (Song et al, 2015), both with open hydroxyacyl chain instead of a macrolactone ring. We thus call this structure Dichondrin D. The MS/MS fragmentation pattern of Dichondrin D could be explained by the characterized structure (Supplementary Fig.…”

Section: Sampling and Identification Of Resin Glycosides From Convolvulaceae Species Using Ms/ms And Nmrmentioning

confidence: 94%

Computational metabolomics illuminates the lineage-specific diversification of resin glycoside acylsugars in the morning glory (Convolvulaceae) family

Kruse

Bennett

Mahood

et al. 2021

Preprint

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Acylsugars are a class of plant defense compounds produced across many distantly related families. Members of the horticulturally important morning glory (Convolvulaceae) family produce a diverse sub-class of acylsugars called resin glycosides (RGs), which comprise oligosaccharide cores, hydroxyacyl chain(s), and decorating aliphatic and aromatic acyl chains. While many RG structures are characterized, the extent of structural diversity of this class in different genera and species is not known. In this study, we asked whether there has been lineage-specific diversification of RG structures in different Convolvulaceae species that may suggest diversification of the underlying biosynthetic pathways. Liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) was performed from root and leaf extracts of 26 species sampled in a phylogeny-guided manner. LC-MS/MS revealed thousands of peaks with signature RG fragmentation patterns with one species producing over 300 signals, mirroring the diversity in Solanaceae-type acylsugars. A novel RG from Dichondra argentea was characterized using Nuclear Magnetic Resonance spectroscopy, supporting previous observations of RGs with open hydroxyacyl chains instead of closed macrolactone ring structures. Substantial lineage-specific differentiation in utilization of sugars, hydroxyacyl chains, and decorating acyl chains was discovered, especially among Ipomoea and Convolvulus - the two largest genera in Convolvulaceae. Adopting a computational, knowledge-based strategy, we further developed a high-recall workflow that successfully explained ~72% of the MS/MS fragments, predicted the structural components of 11/13 previously characterized RGs, and partially annotated ~45% of the RGs. Overall, this study improves our understanding of phytochemical diversity and lays a foundation for characterizing the evolutionary mechanisms underlying RG diversification.

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“…To solve the existing problem of tautomerism, the remanent resin glycoside fraction of C. chinensis was converted into aminoalditol derivatives with p ‐anisidine, and then eight new resin glycosides, including three trisaccharide derivatives cuses 5‐7 ( 7 – 9 ), were isolated 43 . In addition, Song et al also isolated an acylated trisaccharide dichondrin C ( 6 ), along with cus 3 ( 4 ), from Dichondra repens 50 …”

Section: Structures and Classification Of Resin Glycosidesmentioning

confidence: 99%

“…Two non‐macrocyclic resin glycosides dichondrins A ( 30 ) and B ( 31 ) were isolated from D. repens 50 . Their sugar core and acylated residues are similar except for the aglycone moiety, 11 S ‐hydroxyhexadecanoic acid for 30 and 3 S ,11 S ‐dihydroxyhexadecanoic acid for 31 .…”

Section: Structures and Classification Of Resin Glycosidesmentioning

confidence: 99%

“…Xuan's group have isolated a number of MDR reversal resin glycosides from D. repens , M. hederacea and I. muricata , which could also increase the cytotoxicity of vincristine by 1.03–407.1 fold at a concentration of 25 μM 50,55,73 . In additionl, some non‐macrolactone resin glycosides, such as calonyctin J ( 38 ) and merremin F ( 83 ), also showed MDR reversal activities, suggesting that the macrocyclic structure of resin glycosides was not essential for the anti‐MDR activity 55,73 …”

Section: Biological Activitiesmentioning

confidence: 99%

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Chemistry and biological activity of resin glycosides from Convolvulaceae species

Fan

Jiang

et al. 2022

Medicinal Research Reviews

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Carbohydrate-based drug discovery has gained more and more attention during the last few decades. Resin glycoside is a kind of novel and complex glycolipids mainly distributed in plants of the family Convolvulaceae. Over the last decade, a number of natural resin glycosides and derivatives have been isolated and identified, and exhibited a broad spectrum of biological activities, such as cytotoxic, multidrug-resistant reversal on both microbial pathogens and mammalian cancer cells, antivirus, anticonvulsant, antidepressant, sedative, vasorelaxant, laxative, and α-glucosidase inhibitory effects, indicating their potential as lead compounds for drug discovery. A systematic review of the literature studies was carried out to summarize the chemistry and biological activity of resin glycosides from Convolvulaceae species, based on various data sources such as PubMed, Web of Science, Scopus, and Google scholar. The keyword "Convolvulaceae" was paired with "resin glycoside," "glycosidic acid," "glycolipid," or "oligosaccharide," and the references published between 2009 and June 2021 were covered. In this article, we comprehensively reviewed the structures of 288 natural resin glycoside and derivatives newly reported in the last decade. Moreover, we summarized the biological activities and mechanisms of action of the resin

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Multidrug resistance–reversal effects of resin glycosides from Dichondra repens

Cited by 14 publications

References 12 publications

Illuminating the lineage-specific diversification of resin glycoside acylsugars in the morning glory (Convolvulaceae) family using computational metabolomics

Illuminating the lineage-specific diversification of resin glycoside acylsugars in the morning glory (Convolvulaceae) family using computational metabolomics

Computational metabolomics illuminates the lineage-specific diversification of resin glycoside acylsugars in the morning glory (Convolvulaceae) family

Chemistry and biological activity of resin glycosides from Convolvulaceae species

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