scholarly journals Metabolite Profiling and Transcriptome Analysis Explains Difference in Accumulation of Bioactive Constituents in Licorice (Glycyrrhiza uralensis) Under Salt Stress

2021 ◽  
Vol 12 ◽  
Author(s):  
Chengcheng Wang ◽  
Lihong Chen ◽  
Zhichen Cai ◽  
Cuihua Chen ◽  
Zixiu Liu ◽  
...  
Keyword(s):  
Salt Stress ◽  
Metabolite Profiling ◽  
Glycyrrhiza Uralensis ◽  
Flavonoid Glycosides ◽  
Bioactive Constituents ◽  
Triterpenoid Saponins ◽  
Helix Loop Helix ◽  
Saponin Biosynthesis ◽  
Coa Ligase ◽  
The Difference

Salinity stress significantly affects the contents of bioactive constituents in licorice Glycyrrhiza uralensis. To elucidate the molecular mechanism underlying the difference in the accumulation of these constituents under sodium chloride (NaCl, salt) stress, licorice seedlings were treated with NaCl and then subjected to an integrated transcriptomic and metabolite profiling analysis. The transcriptomic analysis results identified 3,664 differentially expressed genes (DEGs) including transcription factor family MYB and basic helix-loop-helix (bHLH). Most DEGs were involved in flavonoid and terpenoid biosynthesis pathways. In addition, 121 compounds including a triterpenoid and five classes of flavonoids (isoflavone, flavone, flavanone, isoflavan, and chalcone) were identified, and their relative levels were compared between the stressed and control groups using data from the ultrafast liquid chromatography (UFLC)–triple quadrupole–time of flight–tandem mass spectrometry (TOF–MS/MS) analysis. Putative biosynthesis networks of the flavonoids and triterpenoids were created and combined with structural DEGs such as phenylalanine ammonia-lyase (PAL), 4-coumarate-CoA ligase [4CL], cinnamate 4-hydroxylase [C4H], chalcone synthase [CHS], chalcone-flavanone isomerase [CHI], and flavonoid-3′,5′ hydroxylase (F3′,5′H) for flavonoids, and CYP88D6 and CYP72A154 for glycyrrhizin biosynthesis. Notably, significant upregulation of UDP-glycosyltransferase genes (UGT) in salt-stressed licorice indicated that postmodification of glycosyltransferase may participate in downstream biosynthesis of flavonoid glycosides and triterpenoid saponins. Accordingly, the expression trend of the DEGs is positively correlated with the accumulation of glycosides. Our study findings indicate that key DEGs and crucial UGT genes co-regulate flavonoid and saponin biosynthesis in licorice under salt stress.

scholarly journals A candidate gene identified in converting platycoside E to platycodin D from Platycodon grandiflorus by transcriptome and main metabolites analysis

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Xinglong Su ◽  
Yingying Liu ◽  
Lu Han ◽  
Zhaojian Wang ◽  
Mengyang Cao ◽  
...  
Keyword(s):  
Candidate Gene ◽  
Orthogonal Experiment ◽  
Triterpenoid Saponin ◽  
Gene Encoding ◽  
Triterpenoid Saponins ◽  
Platycodin D ◽  
Polysaccharide Content ◽  
Saponin Biosynthesis ◽  
Polysaccharide Synthesis ◽  
Experimental Use

AbstractPlatycodin D and platycoside E are two triterpenoid saponins in Platycodon grandiflorus, differing only by two glycosyl groups structurally. Studies have shown β-Glucosidase from bacteria can convert platycoside E to platycodin D, indicating the potential existence of similar enzymes in P. grandiflorus. An L9(34) orthogonal experiment was performed to establish a protocol for calli induction as follows: the optimal explant is stems with nodes and the optimum medium formula is MS + NAA 1.0 mg/L + 6-BA 0.5 mg/L to obtain callus for experimental use. The platycodin D, platycoside E and total polysaccharides content between callus and plant organs varied wildly. Platycodin D and total polysaccharide content of calli was found higher than that of leaves. While, platycoside E and total polysaccharide content of calli was found lower than that of leaves. Associating platycodin D and platycoside E content with the expression level of genes involved in triterpenoid saponin biosynthesis between calli and leaves, three contigs were screened as putative sequences of β-Glucosidase gene converting platycoside E to platycodin D. Besides, we inferred that some transcription factors can regulate the expression of key enzymes involved in triterpernoid saponins and polysaccharides biosynthesis pathway of P. grandiflorus. Totally, a candidate gene encoding enzyme involved in converting platycoside E to platycodin D, and putative genes involved in polysaccharide synthesis in P. grandiflorus had been identified. This study will help uncover the molecular mechanism of triterpenoid saponins biosynthesis in P. grandiflorus.

scholarly journals Variations in morphology, physiology, and multiple bioactive constituents of Lonicerae Japonicae Flos under salt stress

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Zhichen Cai ◽  
Xunhong Liu ◽  
Huan Chen ◽  
Rong Yang ◽  
Jiajia Chen ◽  
...  
Keyword(s):  
Lipid Peroxidation ◽  
Salt Stress ◽  
Phenolic Acids ◽  
Antioxidant Activities ◽  
Vital Role ◽  
Gray Relational Analysis ◽  
Bioactive Constituents ◽  
Multivariate Statistical ◽  
Medicinal Value ◽  
Quality Formation

AbstractLonicerae Japonicae Flos (LJF) is an important traditional Chinese medicine for the treatment of various ailments and plays a vital role in improving global human health. However, as unable to escape from adversity, the quality of sessile organisms is dramatically affected by salt stress. To systematically explore the quality formation of LJF in morphology, physiology, and bioactive constituents' response to multiple levels of salt stress, UFLC-QTRAP-MS/MS and multivariate statistical analysis were performed. Lonicera japonica Thunb. was planted in pots and placed in the field, then harvested after 35 days under salt stress. Indexes of growth, photosynthetic pigments, osmolytes, lipid peroxidation, and antioxidant enzymes were identified to evaluate the salt tolerance in LJF under different salt stresses (0, 100, 200, and 300 mM NaCl). Then, the total accumulation and dynamic variation of 47 bioactive constituents were quantitated. Finally, Partial least squares discrimination analysis and gray relational analysis were performed to systematically cluster, distinguish, and evaluate the samples, respectively. The results showed that 100 mM NaCl induced growth, photosynthetic, antioxidant activities, osmolytes, lipid peroxidation, and multiple bioactive constituents in LJF, which possessed the best quality. Additionally, a positive correlation was found between the accumulation of phenolic acids with antioxidant enzyme activity under salt stress, further confirming that phenolic acids could reduce oxidative damage. This study provides insight into the quality formation and valuable information to improve the LJF medicinal value under salt stress.

scholarly journals One-Pot Bi-Enzymatic Cascade Synthesis of Novel Ganoderma Triterpenoid Saponins

Catalysts ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 580
Author(s):  
Te-Sheng Chang ◽  
Chien-Min Chiang ◽  
Tzi-Yuan Wang ◽  
Yu-Li Tsai ◽  
Yu-Wei Wu ◽  
...  
Keyword(s):  
High Performance ◽  
Aqueous Solubility ◽  
Major Product ◽  
Cyclodextrin Glucanotransferase ◽  
Bioactive Constituents ◽  
Ganoderic Acid ◽  
One Pot ◽  
Triterpenoid Saponins ◽  
Medicinal Fungus ◽  
Triterpenoid Glycosides

Ganoderma lucidum is a medicinal fungus whose numerous triterpenoids are its main bioactive constituents. Although hundreds of Ganoderma triterpenoids have been identified, Ganoderma triterpenoid glycosides, also named triterpenoid saponins, have been rarely found. Ganoderic acid A (GAA), a major Ganoderma triterpenoid, was synthetically cascaded to form GAA-15-O-β-glucopyranoside (GAA-15-G) by glycosyltransferase (BtGT_16345) from Bacillus thuringiensis GA A07 and subsequently biotransformed into a series of GAA glucosides by cyclodextrin glucanotransferase (Toruzyme® 3.0 L) from Thermoanaerobacter sp. The optimal reaction conditions for the second-step biotransformation of GAA-15-G were found to be 20% of maltose; pH 5; 60 °C. A series of GAA glucosides (GAA-G2, GAA-G3, and GAA-G4) could be purified with preparative high-performance liquid chromatography (HPLC) and identified by mass and nucleic magnetic resonance (NMR) spectral analysis. The major product, GAA-15-O-[α-glucopyranosyl-(1→4)-β-glucopyranoside] (GAA-G2), showed over 4554-fold higher aqueous solubility than GAA. The present study demonstrated that multiple Ganoderma triterpenoid saponins could be produced by sequential actions of BtGT_16345 and Toruzyme®, and the synthetic strategy that we proposed might be applied to many other Ganoderma triterpenoids to produce numerous novel Ganoderma triterpenoid saponins in the future.

scholarly journals Lignan Glycosides and Flavonoid Glycosides from the Aerial Portion of Lespedeza cuneata and Their Biological Evaluations

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1920 ◽  
Author(s):  
Jiwon Baek ◽  
Tae Lee ◽  
Jae-Hyoung Song ◽  
Eunyong Choi ◽  
Hyun-Jeong Ko ◽  
...  
Keyword(s):  
Negative Control ◽  
Breast Cancer Cell Lines ◽  
Flavonoid Glycosides ◽  
Phytochemical Analysis ◽  
Bioactive Constituents ◽  
Lespedeza Cuneata ◽  
2D Nmr Spectroscopy ◽  
Aerial Portion ◽  
Alkaline Phosphatase Staining ◽  
Lignan Glycosides

Lespedeza cuneata (Fabaceae), known as Chinese bushclover, has been used in traditional medicines for the treatment of diseases including diabetes, hematuria, and insomnia. As part of a continuing search for bioactive constituents from Korean medicinal plant sources, phytochemical analysis of the aerial portion of L. cuneata led to the isolation of two new lignan glycosides (1,2) along with three known lignan glycosides (3–7) and nine known flavonoid glycosides (8–14). Numerous analysis techniques, including 1D and 2D NMR spectroscopy, CD spectroscopy, HR-MS, and chemical reactions, were utilized for structural elucidation of the new compounds (1,2). The isolated compounds were evaluated for their applicability in medicinal use using cell-based assays. Compounds 1 and 4–6 exhibited weak cytotoxicity against four human breast cancer cell lines (Bt549, MCF7, MDA-MB-231, and HCC70) (IC50 < 30.0 μM). However, none of the isolated compounds showed significant antiviral activity against PR8, HRV1B, or CVB3. In addition, compound 10 produced fewer lipid droplets in Oil Red O staining of mouse mesenchymal stem cells compared to the untreated negative control without altering the amount of alkaline phosphatase staining.

scholarly journals Full-Length Transcriptome Sequences by A Combination of Sequencing Platforms Applied to Isoflavonoid and Triterpenoid Saponin Biosynthesis of Astragalus Mongholicus Bunge

2020 ◽  
Author(s):  
Minzhen Yin ◽  
Shanshan Chu ◽  
Tingyu Shan ◽  
Liangping Zha ◽  
Huasheng Peng
Keyword(s):  
Single Molecule ◽  
Molecular Genetic ◽  
Gene Families ◽  
Triterpenoid Saponin ◽  
Smrt Sequencing ◽  
Triterpenoid Saponins ◽  
Saponin Biosynthesis ◽  
Medicinal Value ◽  
Long Time ◽  
Sequencing Platforms

Abstract Background: Astragalus mongholicus Bunge is an important medicinal plant and has been used in traditional Chinese medicine for a long history, which is rich in isoflavonoids and triterpenoid saponins. Although these active constituents in A. mongholicus have been discovered for a long time, the molecular genetic basis of the isoflavonoid and triterpenoid saponin biosynthesis pathways is virtually unknown due to the lack of a reference genome. The combination of next-generation sequencing (NGS) and single-molecule real-time (SMRT) sequencing to analyze genes involved in the biosynthetic pathways of secondary metabolites in medicinal plants has been widely recognized.Results: In this study, NGS, SMRT sequencing, and targeted compounds were combined to investigate the association between isoflavonoids and triterpenoid saponins and gene expression in roots, stems and leaves of A. mongholicus. A total of four main isoflavonoids and four astragalosides (belong to triterpenoid saponins) were measured, and 44 differentially expressed genes (DEGs) of nine gene families, 44 DEGs of 16 gene families that encode for enzymes involved in isoflavonoid and triterpenoid saponin biosynthesis were identified, separately. Additionally, transcription factors (TFs) associated with isoflavonoid and triterpenoid saponin biosynthesis were analyzed, including 72 MYBs, 53 bHLHs, 64 AP2-EREBPs and 11 bZIPs. The above transcripts exhibit different expression trends in different organs.Conclusions: Our study provides important genetic information for the essential genes of isoflavonoid and triterpenoid saponin biosynthesis in A. mongholicus, and provides a basis for developing its medicinal value.

scholarly journals GuUGT, a glycosyltransferase from Glycyrrhiza uralensis , exhibits glycyrrhetinic acid 3- and 30-O-glycosylation

2019 ◽  
Vol 6 (10) ◽  
pp. 191121 ◽  
Author(s):  
Ying Huang ◽  
Da Li ◽  
Jinhe Wang ◽  
Yi Cai ◽  
Zhubo Dai ◽  
...  
Keyword(s):  
Biosynthetic Pathway ◽  
Glycyrrhetinic Acid ◽  
Glycyrrhiza Uralensis ◽  
Transcriptome Data ◽  
Bioactive Components ◽  
Triterpenoid Saponins ◽  
Genes Encoding ◽  
Engineered Yeast ◽  
Biochemical Analyses

Glycyrrhiza uralensis is a well-known herbal medicine that contains triterpenoid saponins as the predominant bioactive components, and these compounds include glycyrrhetinic acid (GA)-glycoside derivatives. Although two genes encoding UDP-glycosyltransferases (UGTs) that glycosylate these derivates have been functionally characterized in G. uralensis , the mechanisms of glycosylation by other UGTs remain unknown. Based on the available transcriptome data, we isolated a UGT with expression in the roots of G. uralensis . This UGT gene possibly encodes a glucosyltransferase that glycosylates GA derivatives at the 3-OH site. Biochemical analyses revealed that the recombinant UGT enzyme could transfer a glucosyl moiety to the free 3-OH or 30-COOH groups of GA. Furthermore, engineered yeast harbouring genes involved in the biosynthetic pathway for GA-glycoside derivates produced GA-3- O -β-D-glucoside, implying that the enzyme has GA 3-O-glucosyltransferase activity in vivo . Our results could provide a frame for understand the function of the UGT gene family, and also is important for further studies of triterpenoids biosynthesis in G. uralensis .

Flavonoid glycosides of the roots of Glycyrrhiza uralensis

1985 ◽  
Vol 24 (2) ◽  
pp. 339-341 ◽  
Author(s):  
Tsutomu Nakanishi ◽  
Akira Inada ◽  
Kazuko Kambayashi ◽  
Kaisuke Yoneda
Keyword(s):  
Glycyrrhiza Uralensis ◽  
Flavonoid Glycosides

scholarly journals Metabolite Profiling and Classification of Developing Styrax tonkinensis Kernels

Metabolites ◽  
2020 ◽  
Vol 10 (1) ◽  
pp. 21
Author(s):  
Qikui Wu ◽  
Xue Zhao ◽  
Chen Chen ◽  
Zihan Zhang ◽  
Fangyuan Yu
Keyword(s):  
Mass Spectrometry ◽  
Amino Acids ◽  
Metabolite Profiling ◽  
Gas Chromatography Mass Spectrometry ◽  
Flavonoid Glycosides ◽  
Kernel Development ◽  
Time Points ◽  
Pathway Enrichment ◽  
Chromatography Mass Spectrometry ◽  
Biochemical Compositions

Background: Styrax tonkinensis is an economic tree species with high timber, medicine, oil, and ornamental value. Its seed, containing a particularly high oil content, are widely studied for their biodiesel properties by nutritional components and oil body ultrastructure. However, their comprehensive biochemical compositions have not been studied. Methods: During S. tonkinensis kernel development, we collected samples from four time points for metabolite profiling and classification through gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry. Results: A total of 187 and 1556 metabolites were obtained, respectively. All of the metabolites were grouped into 19 and 21 classes by their chemical properties and into 8 clusters based on their change trends, respectively. Among all the metabolites, carboxylic acids and derivatives, flavonoids, fatty acyls, glycerophospholipids, organooxygen compounds, prenol lipids, and steroids and steroid derivatives were the main components. Alanine, glutamine, tryptophan, tyrosine and valine were the five most abundant amino acids. Palmitic acid, stearic acid, oleic acid and linoleic acid were the four major free fatty acids. Flavans, flavonoid glycosides and o-methylated flavonoids were the three major flavonoids. The differential metabolites distributions between different time points were identified. A pathway enrichment was performed, which was mainly focused on three groups, amino acids metabolism, carbon flow from sucrose to lipid and secondary metabolites biosynthesis. Conclusions: It’s the first time to analyze the metabolite fingerprinting for developing S. tonkinensis kernels and identify varied kinds of flavonoids. We performed metabolite profiling, classification and pathway enrichment to assess the comprehensive biochemical compositions. Our results described the change in major metabolites and main metabolic processes during S. tonkinensis kernel development and provided a variety of bases for seed applications as biofuel or medicine.

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