Gentiana
210167067
Seven new chemical constituents from the roots of Gentiana macrophylla pall.
Gentimilegenins A, B (1, 2) (6R, 8R) 6 hydroxy swerimuslactone A (3) (6R, 8S) 6 hydroxy swerimuslactone A (4) 4 hydroxy roburic acid methyl ester (5) 3' hydroxy gentioxepine (6) N heptacosanoyl anthranilic acid (7a) N nonacosanoyl anthranilic acid (7b) together with 40 known compounds were isolated from the roots of Gentiana macrophylla Pall. Their structures were elucidated on the basis of comprehensive analysis of HRESIMS, IR, 1D 2D NMR and X ray diffraction. The anti inflammatory effects of selected compounds were also evaluated through the detection of their inhibitory effects on NO production in LPS induced RAW264.7 macrophage cells.
Fitoterapia
Shu-Bing Hou Xin Wang Rong Huang Huan Liu Hai-Min Hu Wen-Yi Hu Si-Tong Lv Huan Zhao Guang Chen
214644480
Discrimination of Gentiana and Its Related Species Using IR Spectroscopy Combined with Feature Selection and Stacked Generalization
Gentiana, which is one of the largest genera of Gentianoideae, most of which had potential pharmaceutical value, and applied to local traditional medical treatment. Because of the phytochemical diversity and difference of bioactive compounds among species, which makes it crucial to accurately identify authentic Gentiana species. In this paper, the feasibility of using the infrared spectroscopy technique combined with chemometrics analysis to identify Gentiana and its related species was studied. A total of 180 batches of raw spectral fingerprints were obtained from 18 species of Gentiana and Tripterospermum by near infrared (NIR: 10,000 4000 cm 1) and Fourier transform mid infrared (MIR: 4000 600 cm 1) spectrum. Firstly, principal component analysis (PCA) was utilized to explore the natural grouping of the 180 samples. Secondly, random forests (RF) support vector machine (SVM) and K nearest neighbors (KNN) models were built while using full spectra (including 1487 NIR variables and 1214 FT MIR variables, respectively) The MIR SVM model had a higher classification accuracy rate than the other models that were based on the results of the calibration sets and prediction sets. The five feature selection strategies, VIP (variable importance in the projection) Boruta, GARF (genetic algorithm combined with random forest) GASVM (genetic algorithm combined with support vector machine) and Venn diagram calculation, were used to reduce the dimensions of the data variable in order to further reduce numbers of variables for modeling. Finally, 101 NIR and 73 FT MIR bands were selected as the feature variables, respectively. Thirdly, stacking models were built based on the optimal spectral dataset. Most of the stacking models performed better than the full spectra based models. RF and SVM (as base learners) combined with the SVM meta classifier, was the optimal stacked generalization strategy. For the SG Ven MIR SVM model, the accuracy (ACC) of the calibration set and validation set were both 100% Sensitivity (SE) specificity (SP) efficiency (EFF) Matthews correlation coefficient (MCC) and Cohen's kappa coefficient (K) were all 1, which showed that the model had the optimal authenticity identification performance. Those parameters indicated that stacked generalization combined with feature selection is probably an important technique for improving the classification model predictive accuracy and avoid overfitting. The study result can provide a valuable reference for the safety and effectiveness of the clinical application of medicinal Gentiana.
Molecules
Tao Shen Hong Yu
225800985
Variability of six secondary metabolites in plant parts and developmental stages in natural populations of rare Gentiana pneumonanthe
Abstract Variability in the contents of representative secondary metabolites in Gentiana pneumonanthe individuals was investigated in relation to population origin, plant parts and developmental stage. Chemical analyses (HPLC) of six secondary metabolites (swertiamarin (SWM) gentiopicrin (GP) sweroside (SWZ) mangiferin (MGF) isoorientin (ISOOR) and isovitexin (ISOV) were performed for individuals from six populations located within a 3 x 3 km area at Maljen Mt. and separately for below and above ground plant parts in three developmental stages. Different plant parts showed pronounced differences in the contents of the six secondary metabolites and a high level of variability during the plant ontogeny. The highest contents of three dominant compounds (SWM, GP, and MGF) were detected in different developmental stages. Both below and above ground plant parts contained GP, MGF, SWZ, and SWM at some developmental stages, whereas ISOOR and ISOV were registered in above ground parts. The full flowering stage was characterized by the highest contents of MGF, GP, and ISOOR in aboveground and GP in belowground parts. In the post flowering stage, a high content of MF was detected in below ground parts. The results of this study contribute to a better understanding of interpopulation, ontogenetic and between organ variability in rare and threatened G. pneumonanthe.
Zorica Popovic Dijana Krstic Milosevic Milena Stefanovic Vera Vidakovic Rada Matic Jovana Jankovic Srdjan Bojovic
58950687
Isoorientin derived from Gentiana veitchiorum Hemsl. flowers inhibits melanogenesis by down regulating MITF induced tyrosinase expression.
BACKGROUND Gentiana is a genus of flowering plants in Gentianaceae family, which comprises of 1,600 species. The roots of few species of Gentiana, also known as Long Dan Cao in Chinese, are traditionally used in herbal remedies for a wide variety of liver associated diseases. The medicinal part of Gentiana is root; however, the trumpet shaped flowers are seldom being used. PURPOSE We investigated the anti melanogenesis effect of water extract of Gentiana veitchiorum Hemsl. flowers, and isoorientin was identified to be the active compound. STUDY DESIGN We tested the anti melanogenesis effects of extracts deriving from different parts of G. veitchiorum, followed by identification of active ingredients within the extracts. The mechanism of inhibitory effect on melanogenesis, triggered by isoorientin, was elucidated by in vitro analyses. METHODS HPLC was applied to identify the components in water extracts from different parts of G. veitchiorum. The cytotoxicity of extracts and pure compounds in cultured B16F10 murine melanoma cells was determined by MTT and trypan blue assays. Melanin assay, tyrosinase assay, RT PCR, luciferase assay and western blot were used to analyze the effect of isoorientin in melanin content, tyrosinase activity, as well as the expressions of those related genes and proteins. RESULTS We identified an inhibitory effect on melanogenesis from water extract of G. veitchiorum flowers in B16F10 cells. Isoorientin, a major flavone in the extract, was identified to be an active ingredient causing reduction in melanin content in a dose dependent manner. Such reduction was suggested to be a result of suppressed expression of tyrosinase (TYR) tyrosinase related protein 1 (TRP1) and DOPA chrome tautomerase (DCT) Isoorientin also suppressed the expression of microphthalmia associated transcription factor (MITF) through the phosphorylation of cAMP response element binding protein (CREB) CONCLUSION These findings indicate that isoorientin derived from G. veitchiorum flowers may be a potential skin lightening agent for the treatment of skin pigmentary disorders.
Phytomedicine international journal of phytotherapy and phytopharmacology
Qiyun Wu Zack C F Wong Cheng Wang Aster Hei Yiu Fung Emily Wong Gallant Kar-Lun Chan Tina T X Dong Yicun Chen Karl Wah-Keung Tsim
207940105
Caucasian Gentiana Species: Untargeted LC MS Metabolic Profiling, Antioxidant and Digestive Enzyme Inhibiting Activity of Six Plants
The members of Gentiana genus are widely distributed in the Caucasus region where they are used as phytoremedies, but they still have not been studied for their chemical composition and bioactivity. High performance liquid chromatography with diode array and electrospray triple quadrupole mass detection (HPLC DAD ESI QQQ MS) was used to investigate metabolites of herb and roots of six gentians (Gentiana asclepiadea, G. cruciata, G. gelida, G. paradoxa, G. pneumonanthe, G. septemfida) grown in the Caucasus. In total, 137 compounds were found including three carbohydrates, 71 iridoid glycosides (mostly loganic acid) loganin, swertiamarin, gentiopicroside and sweroside derivatives, 40 flavones C O C,O glycosides (such as luteolin, apigenin, chrysoeriol, and acacetin derivatives) two phenolic O glycosides, five hydroxycinnamates, eight xanthones, and seven triterpene glycosides. Most of these compounds were identified in gentian samples for the first time. Quantitative differences were found in levels of seven iridoid glycosides, nine glycosylflavones, and two xanthones obtained by HPLC DAD assay. The gentian extracts were evaluated for their radical scavenging properties against DPPH and superoxide anion radicals, lipid peroxidation inhibition, and a amylase/a glycosidase inhibition. The herb extracts showed higher activity than root extracts. Positive correlations were found between the content of quantified phenolics and antioxidant and digestive enzymes inhibiting activity. The findings presented in our work suggest that the Caucasian gentians are a good source of bioactive phytocompounds with antioxidant and antidiabetic potential.
Metabolites
Daniil N Olennikov Aydan I Gadimli Javanshir I Isaev Nina I Kashchenko Alexey S Prokopyev Tatyana Nikolaevna Kataeva Nadezhda K Chirikova Cecile Vennos
67856858
Differential accumulation of pelargonidin glycosides in petals at three different developmental stages of the orange flowered gentian (Gentiana lutea L. var. aurantiaca)
Corolla color in Gentiana lutea L. exhibits a yellow/orange variation. We previously demonstrated that the orange petal color of G. lutea L. var. aurantiaca is predominantly caused by newly synthesized pelargonidin glycosides that confer a reddish hue to the yellow background color, derived from the carotenoids. However, the anthocyanin molecules of these pelargonidin glycosides are not yet fully identified and characterized. Here, we investigated the regulation, content and type of anthocyanins determining the petal coloration of the orange flowered G. lutea L. var. aurantiaca. Anthocyanins from the petals of G. lutea L. var. aurantiaca were characterized and quantified by HPLC ESI MS/MS (High performance liquid chromatography electrospray ionization tandem mass spectrometry) coupled with a diode array detector in flowers at three different stages of development (S1, S3 and S5) Eleven pelargonidin derivatives were identified in the petals of G. lutea L. var. aurantiaca for the first time, but quantitative and qualitative differences were observed at each developmental stage. The highest levels of these pelargonidin derivatives were reached at the fully open flower stage (S5) where all anthocyanins were detected. In contrast, not all the anthocyanins were detected at the budlet stage (S1) and mature bud stage (S3) and those corresponded to more complex pelargonidin derivatives. The major pelargonidin derivatives found at all the stages were pelargonidin 3 O glucoside, pelargonidin 3,5 O diglucoside and pelargonidin 3 O rutinoside. Furthermore, the expression of DFR (dihydroflavonol 4 reductase) ANS (anthocyanidin synthase) 3GT (UDP glucose:flavonoid 3 O glucosyltransferase) 5GT (UDP glucose:flavonoid 5 O glucosyltransferase) and 5AT (anthocyanin 5 aromatic acyltransferase) genes was analyzed in the petals of three developmental stages, showing that the expression level of DFR, ANS and 3GT parallels the accumulation of the pelargonidin glucosides. Overall, this study enhances the knowledge of the biochemical basis of flower coloration in Gentiana species, and lays a foundation for breeding of flower color and genetic variation studies on Gentiana varieties.
PloS one
Gianfranco Diretto Xin Jin Teresa Capell Changfu Zhu Lourdes Gomez-Gomez
58537649
Gentiana scabra Bunge roots alleviates skin lesions of contact dermatitis in mice.
ETHNOPHARMACOLOGICAL RELEVANCE The roots and rhizomes of Gentiana scabra Bunge in the family Gentianaceae comprise a major herbal medicine for skin diseases caused by wind heat or dampness heat in China, Japan and Korea. This treatment can clear away heat and dry dampness and purge fire from the liver and gallbladder. AIM OF THE STUDY This study was designed to investigate the therapeutic potential and anti inflammatory effects of G. scabra, roots and rhizomes. MATERIALS AND METHODS Thin layer chromatography (TLC) and high performance liquid chromatography (HPLC) revealed the presence of gentiopicrin in the roots and rhizomes of G. scabra. We then investigated the effects of ethanol extract of G. scabra, roots and rhizomes (EEGS) on skin lesions and thickness, erythema and melanin index, histopathological abnormalities, and cytokine and chemokine production in mice with contact dermatitis (CD) induced by 1 fluoro 2,4 dinitrofluorobenzene (DNFB) Moreover, the effects of EEGS on body weights and spleen body weight ratio were evaluated. RESULTS Topical application of EEGS alleviated skin lesions such as surface roughness, excoriations and scabs on the skin of CD mice, as well as prevented skin enlargement, and lowered the erythema and melanin index. In addition, EEGS prevented hyperkeratosis, epidermal hyperplasia and immune cell infiltration, and inhibited TNF a, IFN g, IL 6 and MCP 1 production in inflamed tissues. EEGS did not affect changes in body weights and spleen body weight ratio in contrast to dexamethasone. CONCLUSIONS These data indicate that the roots and rhizomes of G. scabra can be used as anti inflammatory agents for CD with relative safety and that its therapeutic mechanisms are related to regulation of pro inflammatory cytokines such as TNF a and IFN g.
Journal of ethnopharmacology
Beodeul Yang Sura Kim Jung-Hoon Kim Chiyeon Lim Hyungwoo Kim Suin Cho
208534155
Intra individual heteroplasmy in the Gentiana tongolensis plastid genome (Gentianaceae)
Chloroplasts are typically inherited from the female parent and are haploid in most angiosperms, but rare intra individual heteroplasmy in plastid genomes has been reported in plants. Here, we report an example of plastome heteroplasmy and its characteristics in Gentiana tongolensis (Gentianaceae) The plastid genome of G. tongolensis is 145,757 bp in size and is missing parts of petD gene when compared with other Gentiana species. A total of 112 single nucleotide polymorphisms (SNPs) and 31 indels with frequencies of more than 2% were detected in the plastid genome, and most were located in protein coding regions. Most sites with SNP frequencies of more than 10% were located in six genes in the LSC region. After verification via cloning and Sanger sequencing at three loci, heteroplasmy was identified in different individuals. The cause of heteroplasmy at the nucleotide level in plastome of G. tongolensis is unclear from the present data, although biparental plastid inheritance and transfer of plastid DNA seem to be most likely. This study implies that botanists should reconsider the heredity and evolution of chloroplasts and be cautious with using chloroplasts as genetic markers, especially in Gentiana.
PeerJ
Shan-Shan Sun Xiao-Jun Zhou Zhi-Zhong Li Hong-Yang Song Zhi-Cheng Long Peng-Cheng Fu
54522477
Chemical and Morphological Inter and Intrapopulation Variability in Natural Populations of Gentiana pneumonanthe L.
Inter and intrapopulation variability in six natural populations of the rare species Gentiana pneumonanthe was examined based on morphological and chemical data. Population size and linear morphometric parameters differed significantly among populations, but without a clear connection to habitat conditions, i. e. water supply and light availability. Leaf shape varied from ovate to lanceolate in all populations, and one population was distinctive in having the largest number of leaves of transitional shape. HPLC analyses of six secondary metabolites were performed separately for belowground parts, and aboveground vegetative and reproductive parts of individual plants (6 populations x7 individuals x3 plant parts, n=126) in order to examine differences at the population and individual levels. Three secoiridoids (swertiamarin (SWM) sweroside (SWZ) and gentiopicrin (GP) one xanthone (mangiferin (MGF) and two flavones (isoorientin (IO) and isovitexin (IV) were detected and quantified in the analyzed samples: sweroside dominated in the aboveground reproductive part, mangiferin in the aboveground vegetative part, and gentiopicrin in the belowground part. At the population level, differences in contents of the analyzed chemicals among populations were significant only for a few metabolites. At the individual level, a pronounced organ dependent distribution of secondary metabolites was revealed. The results of this study contribute to a better understanding of natural variability within populations of the rare and threatened G. pneumonanthe, and provide data on the contents and within plant distribution of secondary metabolites, which are important as pharmacologically active compounds and may be useful for further biotechnological procedures regarding this species.
Chemistry biodiversity
Zorica Popovic Dijana Krstic-Milosevic Milena Stefanovic Rada Matic Vera Vidakovic Srdan Bojovic
201202229
Complete plastid genome of Gentiana trichotoma (Gentianaceae) and phylogenetic analysis
Abstract The complete plastid genome of Gentiana trichotoma was determined and analyzed in this work. It had a circular mapping molecular with the length of 144,759 bp, has similar gene composition with G. section Cruciata but contains 10 more genes than G. section Kudoa. Phylogenetic analysis showed that G. trichotoma clustered together with section Kudoa rather than section Cruciata. The plastome provided in this work would be useful for elucidation of Gentiana evolution.
Mitochondrial DNA. Part B, Resources
Shan-shan Sun Hui Wang Pengcheng Fu