Seven New Sesquiterpene Glycosides from the Root Bark of <i>Dictamnus dasycarpus</i>

Chang, Jun; Liu, Xuan; Xu, Yaming; Zhang, Jinsheng

doi:10.1021/np000567t

Cited by 37 publications

(26 citation statements)

References 11 publications

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“…Other SNP loci like B440 may encode regulatory proteins (Fan et al., 2016; Sawaki et al., 2009), which similarly respond to stress by regulating transcription of genes involved in pathways such as immunity response. Biomarker M435T576 and its related metabolites belong to a class of terpenoid derivatives that have known antimicrobial and antifungal properties (Bartsch et al., 2010; Chang, Xuan, Xu, & Zhang, 2001; Meng, Lu, Li, Yang, & Tan, 1999; Whitehead, Tiramani, & Bowers, 2016) and are likely sensitive to disease‐mediated signaling processes (Caplan, Padmanabhan, & Dinesh‐Kumar, 2008). For instance, M227T630 was identified as Cornolactone C, an iridoid isolated previously from C. florida (He et al., 2014), which belongs to a compound class known to accumulate in response to infection and has documented antimicrobial properties (Marak, Biere, & Van Damme, 2002).…”

Section: Discussionmentioning

confidence: 99%

Discovering variation of secondary metabolite diversity and its relationship with disease resistance inCornus floridaL.

Pais

Xiang

2018

Ecology and Evolution

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Understanding intraspecific relationships between genetic and functional diversity is a major goal in the field of evolutionary biology and is important for conserving biodiversity. Linking intraspecific molecular patterns of plants to ecological pressures and trait variation remains difficult due to environment‐driven plasticity. Next‐generation sequencing, untargeted liquid chromatography–mass spectrometry (LC‐MS) profiling, and interdisciplinary approaches integrating population genomics, metabolomics, and community ecology permit novel strategies to tackle this problem. We analyzed six natural populations of the disease‐threatened Cornus florida L. from distinct ecological regions using genotype‐by‐sequencing markers and LC‐MS‐based untargeted metabolite profiling. We tested the hypothesis that higher genetic diversity in C. florida yielded higher chemical diversity and less disease susceptibility (screening hypothesis), and we also determined whether genetically similar subpopulations were similar in chemical composition. Most importantly, we identified metabolites that were associated with candidate loci or were predictive biomarkers of healthy or diseased plants after controlling for environment. Subpopulation clustering patterns based on genetic or chemical distances were largely congruent. While differences in genetic diversity were small among subpopulations, we did observe notable similarities in patterns between subpopulation averages of rarefied‐allelic and chemical richness. More specifically, we found that the most abundant compound of a correlated group of putative terpenoid glycosides and derivatives was correlated with tree health when considering chemodiversity. Random forest biomarker and genomewide association tests suggested that this putative iridoid glucoside and other closely associated chemical features were correlated to SNPs under selection.

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Section: Discussionmentioning

confidence: 99%

Discovering variation of secondary metabolite diversity and its relationship with disease resistance inCornus floridaL.

Pais

Xiang

2018

Ecology and Evolution

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“…The root bark of Dictamnus dasycarpus Turcz is known to contain alkaloids, lactones and sesquiterpene glycosides, known as dictamnosides, such as eudesmane-type sesquiterpene glycosides and trinorguaiane-type sesquiterpene glycosides (Zhao et al, 1997(Zhao et al, , 1999(Zhao et al, , 2001Chang et al, 2001;Du et al, 2005). Obviously, Dictamnus dasycarpus Turcz is one of the medicinal plants with potential toxicity.…”

Section: Introductionmentioning

confidence: 99%

Acute and sub-chronic oral toxicity profiles of the aqueous extract of Cortex Dictamni in mice and rats

Wang

et al. 2014

Journal of Ethnopharmacology

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“…5,6) The 60% aqueous acetone extract of the whole herb of P. rotundifolia was subjected to column chromatography on MCI gel CHP 20P, Cosmosil 75 C 18 -OPN and TSK gel Toyopearl HW-40F to yield one novel phenolic glycoside dimer, pyrolaside A (1), and one novel phenolic glycoside trimer, pyrolaside B (2), together with two known phenolic glycosides homoarbutin (3) and isohomoarbutin (4).…”

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Novel Phenolic Glycoside Dimer and Trimer from the Whole Herb of Pyrola rotundifolia

Chang

Inui

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Pyrola rotundifolia (Pyrolaceae) has been used for the treatment for neuralgia, gastric hemorrhage, pulmonary hemorrhage, and arthritic diseases as a traditional Chinese medicine. The water extract of the plant was reported to inhibit the growth of many kinds of human pathogenic bacilli in vitro.1) Thus far only nine compounds, i.e. arbutin, homoarbutin, isohomoarbutin, N-benzyl-2-naphthylamine, chimaphilin, quercetin, gallic acid, protocatechuic acid, and ursolic acid have been isolated from P. rotundifolia.2-4) Wang et al. reported that chimaphilin, N-benzyl-2-naphthylamine, and gallic acid inhibited the growth of the leukemia cell line P388.3) Kosuge et al. reported that anti-inflammatory and analgesic principles of P. rotundifolia were identified as ursolic acid and chimaphilin by in vivo models.4) The focus was set on poplar constituents of P. rotundifolia in this report, as a part of the studies on the hydrophilic bioactive constituents from Chinese medicines. 5,6) The 60% aqueous acetone extract of the whole herb of P. rotundifolia was subjected to column chromatography on MCI gel CHP 20P, Cosmosil 75 C 18 -OPN and TSK gel Toyopearl HW-40F to yield one novel phenolic glycoside dimer, pyrolaside A (1), and one novel phenolic glycoside trimer, pyrolaside B (2), together with two known phenolic glycosides homoarbutin (3) and isohomoarbutin (4). Results and DiscussionCompound 1 for an aromatic ring suggested that compound 1 was a phenolic compound, and the UV absorption also indicated the presence of an aromatic moiety (201.1, 292.7 nm). In the 1 H-NMR spectrum (Table 1), the meta-correlated signals at d 6.96 (1H, d, Jϭ2.7 Hz, H-2) and d 6.91 (1H, d, Jϭ2.7 Hz, H-6) defined a 1,3,4,5-tetrasubstituted aromatic ring, which was confirmed in the 13 C-NMR spectrum by four quaternary aromatic carbon peaks at d 153.1 (C-1), 129.0 (C-3), 148.4 (C-4), and 129.2 (C-5) and two methine peaks at d 120.6 (C-2), and 119.0 (C-6). The high field of 1 H-NMR spectrum showed one aromatic methyl at d 2.25 (3H, s, H-7). The linkage between the methyl group and aromatic ring, established unambiguously by an HMBC experiment, concluded that 1 was the analogue of homoarbutin. The molecular formula showed that 1 was the dehydro homoarbutin dimer. The signals in the NMR spectra indicated the symmetry of the two homoarbutin units in the molecule. The linkage between homoarbutin units must be located on C-5 and C-5Ј according to the 13 C-NMR spectrum. The glucosyl moiety was identified by acid hydrolysis of 1 and comparison with authentic sample. The b-stereochemistry of anomeric carbon was determined by the coupling constant (Jϭ7.4 Hz) of anomeric proton.7) With all of these evidence, compound 1 was identified as 5-5Ј-dehydro-di(3-methyl-4-hydroxy-phenyl-1-O-b-Dglucopyranoside), and given the trivial name pyrolaside A.Compound 2 was obtained as a white amorphous powder. The positive and negative ESI-MS showed quasimolecular ion peaks at m/z 877 [MϩNa] ϩ and 853 [MϪH] ϩ , respectively, indicating a molecular weight of 854. The molecu...

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Seven New Sesquiterpene Glycosides from the Root Bark of Dictamnus dasycarpus

Cited by 37 publications

References 11 publications

Discovering variation of secondary metabolite diversity and its relationship with disease resistance inCornus floridaL.

Discovering variation of secondary metabolite diversity and its relationship with disease resistance inCornus floridaL.

Acute and sub-chronic oral toxicity profiles of the aqueous extract of Cortex Dictamni in mice and rats

Novel Phenolic Glycoside Dimer and Trimer from the Whole Herb of Pyrola rotundifolia

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