SCIENTIA HORTICULTURAE
·
2019
·
IF 1.961
Hu Zhao,Shanshan Feng,Wei Zhou,Guoyin Kai
Toon buds have been used in China as an important woody vegetable for its unique flavor. However, the changes of volatile terpenoids related to flavor and their biosynthesis in postharvest toon buds after cold storage remain largely unknown. Therefore, a transcriptomic database must be constructed to analyze the molecular mechanism of terpenoid biosynthesis in toon buds during cold storage. The chemical profiles of volatile terpenoids over postharvest storage periods were comparatively analyzed by gas chromatography–mass spectrometry. Results showed that the total content of volatile terpenoids and their oxidates, except for monoterpenes and a small portion of sesquiterpenes, increased significantly after cold storage. The transcriptome database derived from different cold storage times was established using BGIseq500 technology. Approximately 6.5 g of clean nucleotides were obtained and de novo assembled into 152 127 non-redundant unigenes, approximately 72.36% of which could be aligned to public databases. Many candidate genes involved in terpenoid biosynthesis were identified. Furthermore, 29 513 unigenes were demonstrated to be differentially expressed under different cold storage times. These differentially expressed genes were functionally annotated by gene ontology enrichment and Kyoto Encyclopedia of Genes and Genomes enrichment analyses. The expression of 20 putative unigenes involved in terpenoid pathways was confirmed by qRT-PCR, the results of which were consistent with the RNA-seq data. These genes with different expression patterns correlated well with the changes in the volatile terpenoids in the toon buds during low-temperature storage. In summary, our results showed that the high expression levels of terpenoid backbone biosynthesis pathways contributed to sesquiterpene biosynthesis after cold storage, which led to high sesquiterpene accumulation in toon buds during low-temperature storage.
研究领域:
植物学
·
分子生物学
·
食品科学
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DOI
高影响因子
Plant Communications
·
2021
·
IF 0
De-Sen Li,Juan Hua,Shi-Hong Luo,Yan-Chun Liu,Yue-Gui Chen,Yi Ling,Kai Guo,Yan Liu,Sheng-Hong Li
Terpenoids are the largest class of natural products with complex structures and extensive bioactivities; their scaffolds are generated by diverse terpenoid synthases (TPSs) from a limited number of isoprenoid diphosphate precursors. Promiscuous TPSs play important roles in the evolution of terpenoid chemodiversity, but they remain largely unappreciated. Here, an extremely promiscuous terpenoid synthase (CcTPS1) of the TPS-b subfamily was cloned and functionally characterized from a leaf-specific transcriptome of the Lamiaceae plant Colquhounia coccinea var. mollis . CcTPS1 is the first sester-/di-/sesqui-/mono-TPS identified from the plant kingdom, accepting C 25 /C 20 /C 15 /C 10 diphosphate substrates to generate a panel of sester-/di-/sesqui-/mono-terpenoids. Engineered Escherichia coli expressing CcTPS1 produced three previously unreported terpenoids (two sesterterpenoids and a diterpenoid) with rare cyclohexane-containing skeletons, along with four sesquiterpenoids and one monoterpenoid. Their structures were elucidated by extensive nuclear magnetic resonance spectroscopy. Nicotiana benthamiana transiently expressing CcTPS1 also produced the diterpenoid and sesquiterpenoids, demonstrating the enzyme’s promiscuity in planta . Its highly leaf-specific expression pattern combined with detectable terpenoid products in leaves of C . coccinea var. mollis and N. benthamiana expressing CcTPS1 suggested that CcTPS1 was mainly responsible for diterpenoid and sesquiterpenoid biosynthesis in plants. CcTPS1 expression and the terpenoid products could be induced by methyl jasmonate, suggesting their possible role in plant–environment interaction. CcTPS1 was localized to the cytosol and may differ from mono-TPSs in subcellular compartmentalization and substrate tolerance. These findings will greatly aid our understanding of plant TPS evolution and terpenoid chemodiversity; they also highlight the enormous potential of transcriptome mining and heterologous expression for the exploration of unique enzymes and natural products hidden in plants.
研究领域:
植物学
·
生物化学
·
代谢工程
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DOI
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
·
2013
·
IF 2.947
Jin-Jun Hou,Wan-Ying Wu,Jian Liang,Zhou Yang,Hua-Li Long,Lu-Ying Cai,Lin Fang,Dan-Dan Wang,Shuai Yao,Xuan Liu,Bao-Hong Jiang,De-An Guo
Kansui radix is a famous poisonous traditional Chinese medicine. However, due to its different types of constituents with broad polarity, a variety of UV absorptions and lack of the reference standards, it was difficult to simultaneously determine the main component in kanui radix. A single, multi-faceted, enhanced strategy, exogenous reference standard – single standard to determine multi-components method (ERS-SSDMC), was proposed. Thirteen major components of kansui radix, including three jatrophane diterpenoids, eight ingenane diterpenoids and two triterpenes, among which there were three pairs of isomers, were simultaneously assayed. A C8 column, packed with 2.7 μm core–shell particles, was optimized to separate these constituents in 25 min on HPLC instrument detected at a program wavelength. Ethyl benzoate employed as single exogenous reference standard. The method was fully validated with respect to linearity ( r 2 > 0.9995), LOQs (0.1–0.4 μg/mL), precision, accuracy (92–114%, RSD < 4.4%) and stability. The robustness of the method was performed by Plackett–Burmantest tests which eight primary chromatographic parameters were investigated. It was found that the two factors, wavelength and flow rate, should be strictly controlled. A total of 75 batches of kansui radix and its three different processing products were successfully analyzed and discriminated by applying the proposed method. This work demonstrates an effective strategy for the SSDMC method making the simultaneous assay of complex multi-component TCM system achievable.
研究领域:
中药学
·
分析化学
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产品关联
DOI
PubMed
高影响因子
Phytochemistry Letters
·
2025
·
IF 1.4
Jiaxing Yu,Adila Abudurexiti,Guangmin Yao
Two new compounds, a norditerpenoid and a megastigmane sesquiterpenoid, were isolated from the ethyl acetate extract of Pieris formosa leaves collected in Yichang, Hubei, China, together with eight known megastigmane sesquiterpenoids. Their structures were elucidated by spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Pormoside A ( 1 ) represents the first example of a 17- β - D -glucopyranosyloxy-substituted 14,15-di- nor -cyclophytane diterpenoid. All isolates were evaluated for α -glucosidase inhibitory activity. Pormoside A ( 1 ) (IC 50 = 112.90 ± 3.98 μ M) showed significantly more potent inhibition than the positive control acarbose (IC 50 = 219.55 ± 3.95 μ M). Molecular docking studies of pormoside A and B further revealed their binding interactions with α -glucosidase.
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产品关联
DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2022
·
IF 5.895
Zhibo Hu,Yujiao Zhu,Jun Chen,Junjie Chen,Chunyuan Li,Zhizeng Gao,Jing Li,Lan Liu
Five new carotane sesquiterpenoids (asperalacids A–E (1–5)), one new tricyclic sesquiterpenoid (4-hydroxy-5(6)-dihydroterrecyclic acid A (6)), and two known analogues (7–8) were obtained from a seagrass-derived fungus Aspergillus alabamensis, which was speculated to be a phytopathogenic fungus, isolated from the necrotic leaves of Enhalus acoroides. The structures of 1–6 were established by a combination of spectroscopic methods, including comprehensive NMR analysis, mass spectrometry, conformational analysis, NMR computational methods, and ECD calculations. Compound 4, with higher inhibitory activity on wheat (Triticum aestivum L.) root and shoot elongation than the positive control terbutryn, a broad-spectrum systemic herbicide, is a new natural plant growth inhibitor. Compound 5, belonging to the rare glycosylated sesquiterpenoid class, represents the first example of glycosylated carotane sesquiterpenoid whose sugar moiety was identified as α-d-glucose. Compounds 1–4 and 6 displayed weak to potent antimicrobial activity against the plant pathogenic fungi Fusarium oxysporum, Fusarium graminearum, and Penicillium italicum and the Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus.
研究领域:
药理学
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化学
·
微生物学
·
植物科学
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产品关联
DOI
PubMed
高影响因子
WORLD JOURNAL OF MICROBIOLOGY & BIOTECHNOLOGY
·
2017
·Vol. 33
·期 2
·1-14
·
IF 1.658
Guan Jian,Shen Songdong,Wu Hao,Liu Xin,Shen Weijie,He Yuan,Duan R.
The filamentous Cyanobacterium Arthrospira is commercially produced and is a functional, high-value, health food. We identified 5 low temperature and low light intensity tolerant strains of Arthrospira sp. (GMPA1, GMPA7, GMPB1, GMPC1, and GMPC3) using ethyl methanesulfonate mutagenesis and low temperature screening. The 5 Arthrospira strains grew rapidly below 14 °C, 43.75 μmol photons m −2 s −1 and performed breed conservation at 2.5 °C, 8.75 μmol photons m −2 s −1 . We used morphological identification and molecular genetic analysis to identify GMPA1, GMPA7, GMPB1 and GMPC1 as Arthrospira platensis , while GMPC3 was identified as Arthrospira maxima . Growth at different culture temperatures was determined at regular intervals using dry biomass. At 16 °C and 43.75 μmol photons m −2 s −1 , the maximum dry biomass production and the mean dry biomass productivity of GMPA1, GMPB1, and GMPC1 were 2057 ± 80 mg l −1 , 68.7 ± 2.5 mg l −1 day −1 , 1839 ± 44 mg l −1 , 60.6 ± 1.8 mg l −1 day −1 , and 2113 ± 64 mg l −1 , 77.7 ± 2.5 mg l −1 day −1 respectively. GMPB1 was chosen for additional low temperature tolerance studies and growth temperature preference. In winter, GMPB1 grew well at mean temperatures <10 °C, achieving 3258 mg dry biomass from a starting 68 mg. In summer, GMPB1 grew rapidly at mean temperatures more than 28 °C, achieving 1140 mg l −1 dry biomass from a starting 240 mg. Phytonutrient analysis of GMPB1 showed high levels of C-phycocyanin and carotenoids. Arthrospira metabolism relates to terpenoids, and the methyl- d -erythritol 4-phosphate pathway is the only terpenoid biosynthetic pathway in Cyanobacteria. The 1-deoxy- d -xylulose 5-phosphate reductoisomerase (DXR) gene from GMPB1 was cloned and phylogenetic analysis showed that GMPB1 is closest to the Cyanobacterium Oscillatoria nigro-viridis PCC711. Low temperature tolerant Arthrospira strains could broaden the areas suitable for cultivation, extend the seasonal cultivation time, and lower production costs.
研究领域:
微生物学
·
生物化学
·
遗传学
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DOI
PubMed
高影响因子
INDUSTRIAL CROPS AND PRODUCTS
·
2022
·
IF 6.449
Shu Diao,Yini Zhang,Qifu Luan,Xianyin Ding,Jiaming Sun,Jingmin Jiang
Oleoresin terpenoids have been widely used in the food , pharmaceutical, and chemical industries. A thorough understanding of oleoresin terpenoid biosynthesis is important for the metabolic engineering of high-valued terpenoid products in plants and microbes and the improvement of oleoresin traits using molecular breeding strategies. TPS-d subfamily members, specific to conifers, determine the oleoresin terpenoid compound diversity. Here, we aimed to identify the TPS-d genes in slash pine ( Pinus elliottii ) and characterize their function and expression patterns in population. Our study reveals two main results: (1) A total of 52 terpene synthase (TPS) candidate genes were identified based on long-read transcripts of slash pine, 12 of which were successfully cloned from the secondary developing xylem RNA. Two levopimaradiene/abietadiene synthases (LAS), one monofunctional isopimaradiene synthase (mISO1)-like, and two α-pinene synthases were identified by comparing with previously known TPS. Next, the two α-pinene synthases and one β-pinene synthase producing multiple products were validated through heterologous expression and in vitro enzyme activity assays, which showed different product profiles from previously identified TPS. (2) The expression status of the cloned TPS genes in 240 slash pine individuals were analyzed. Four exhibited very low expression levels, including those identical to copalyl diphosphate synthases, hemiterpene synthases, diterpene synthases without activity, and one obtained without soluble protein in the heterologous expression. The expression levels of eight TPS genes participating in slash pine oleoresin biosynthesis varied in different individuals and were highly correlated with multiple transcriptional regulators, namely, MYB and MYC. The expression of two α-pinene synthase genes was significantly higher than that of the other TPS genes. Some TPS gene expression levels were positively correlated with the corresponding oleoresin component content. Our results provide an essential reference for exploring the mechanisms of terpene biosynthesis and regulation.
研究领域:
植物生物化学
·
分子生物学
·
遗传学
·
代谢工程
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产品关联
DOI
高影响因子
Journal of Analytical Methods in Chemistry
·
2018
·
IF 1.262
Hui Zhang,Huijie Jiang,Xiaojing Zhang,Shengqiang Tong,Jizhong Yan
Triterpenoids are the major secondary metabolites and active substances in Ganoderma, considered as the “marker compounds” for the chemical evaluation or standardization of Ganoderma. A response surface methodology was used to optimize the ultrasonic-assisted extraction of triterpenoids. The extraction rate was 7.338 ± 0.150 mg/g under the optimum conditions: 87% ethanol, ratio of solid to liquid (w : v) 1 : 28, and ultrasound extraction time 36 min. Based on the high sensitivity and selectivity of HPLC-LTQ-Orbitrap-MSn, 24 components of triterpenoids were tentatively identified in the negative mode. Then, the global chemical profiling consisting of HPLC and TLC fingerprints generated by ChemPattern™ software was developed for evaluation of Ganoderma species. For fingerprint analysis, 11 peaks of triterpenoids were selected as the characteristic peaks to evaluate the similarities of different samples. The correlation coefficients of similarity were greater than 0.830. The cluster analysis showed a clear separation of three groups, and 11 peaks played key roles in differentiating these samples. The developed global chemical profiling method could be applied for rapid evaluation, quality control, and authenticity identification of Ganoderma and other herbal medicines.
研究领域:
药用植物学
·
分析化学
✓ 已验证
DOI
高影响因子
Nature Communications
·
2025
·Vol. 16
·期 1
·1-16
·
IF 15.7
Li Yang,Lu Xuteng,Cheng Xufeng,Xia Keyu,Hu Junyan,Wang Peiyu,Pang Peiyuan,Gao Bomin,Sun Demeng,Zhang Zhuzhen,Li Dongdong,Deng Zengqin,Tian Changlin,Xie Chang,Yao Jing
Our skin safeguards the body homeostasis for health and also provides psychological consolation in social life. Natural essential oils are widely used for skin maintenance, while the molecular target and mechanism of action remain largely unknown. Here, we report that citronellal, a plant-derived acyclic monoterpene commonly used for personal care, stimulates skin renewal by promoting keratinocyte proliferation through the activation of TRPV3. We further present cryo-EM structures of human TRPV3 in complex with acyclic monoterpenes, including citronellal, citral, linalool and isodihydrolavandulal, determined at resolutions of 3.1-3.6 Å. Our structural and functional analysis unmasks consistent yet subtly different binding modes within the TRPV3 vanilloid site. Our results elucidate that essential oil ligands activate TRPV3 channels by competitively displacing endogenous lipids from the vanilloid site. Together, these findings identify TRPV3 as the molecular target of natural acyclic monoterpenes for skin renewal, and delineate the structural basis of action, thus being instrumental for moving forward skin healthcare.
研究领域:
生物化学
·
结构生物学
·
皮肤病学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2024
·
IF 5.7
Jiao Li,Ruiyang Li,Na Shang,Yan Men,Yi Cai,Yan Zeng,Weidong Liu,Jiangang Yang,Yuanxia Sun
The addition of the O-linked N-acetylglucosamine (O-GlcNAc) is a significant modification for active molecules, such as proteins, carbohydrates, and natural products. However, the synthesis of terpenoid glycoside derivatives decorated with GlcNAc remains a challenging task due to the absence of glycosyltransferases, key enzymes for catalyzing the transfer of GlcNAc to terpenoids. In this study, we demonstrated that the enzyme mutant UGT74AC1T79Y/L48M/R28H/L109I/S15A/M76L/H47R efficiently transferred GlcNAc from uridine diphosphate (UDP)-GlcNAc to a variety of terpenoids. This powerful enzyme was employed to synthesize GlcNAc-decorated derivatives of terpenoids, including mogrol, steviol, andrographolide, protopanaxadiol, glycyrrhetinic acid, ursolic acid, and betulinic acid for the first time. To unravel the mechanism of UDP-GlcNAc recognition, we determined the X-ray crystal structure of the inactivated mutant UGT74AC1His18A/Asp111A in complex with UDP-GlcNAc at a resolution of 1.66 Å. Through molecular dynamic simulation and activity analysis, we revealed the molecular mechanism and catalytically important amino acids directly involved in the recognition of UDP-GlcNAc. Overall, this study not only provided a potent biocatalyst capable of glycodiversifying natural products but also elucidated the structural basis for UDP-GlcNAc recognition by glycosyltransferases.
研究领域:
生物化学
·
结构生物学
·
合成生物学
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产品关联
DOI
PubMed
高影响因子
Natural Products and Bioprospecting
·
2018
·Vol. 8
·期 6
·413-418
·
IF 0
Wang Xia,Peng Xing-Rong,Lu Jing,Hu Gui-Lin,Qiu Ming-Hua
Abstract In present study, four new dammarane-type triterpenoids, namely caffruones A–D ( 1 – 4 ), were isolated from the cherries of Coffea arabica . Their structures were elucidated by extensive spectroscopic analysis including 1D, 2D NMR (HSQC, HMBC, 1 H– 1 H COSY, and ROESY), HRMS and IR spectra. This is the first time that tetracyclic triterpenes have been reported in genus Coffea . Graphical Abstract
研究领域:
植物化学
·
天然产物研究
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产品关联
DOI
PubMed
HELVETICA CHIMICA ACTA
·
2016
·Vol. 99
·期 1
·90-94
·
IF 1.087
Mei Ping Zhao,Xin Chao Liu,Daowan Lai,Ligang Zhou,Zhi Long Liu
Water-distilled essential oil from Elsholtzia ciliate (Labiatae) aerial parts at flowering stage was analyzed by gas chromatography/mass spectrometry (GC/MS). Thirty-six compounds, accounting for 98.3% of the total oil content, were identified, and the main components of the essential oil were dehydroelsholtzia ketone (26.5%), ( R )-carvone (16.6%), elsholtzia ketone (14.6%), and D -limonene (4.1%). The essential oil contained higher amounts of monoterpenoids (83.4%) than of sesquiternoids (8.3%). Bioactivity-directed chromatographic separation of the essential oil on repeated silica gel columns led to the isolation of three monoterpenoids. The essential oil possessed fumigant toxicity against the booklice ( Liposcelis bostrychophila ) with an LC 50 value of 475.2 μg/l, while the isolated constituents, ( R )-carvone, dehydroelsholtzia ketone, and elsholtzia ketone had LC 50 values of 417.4, 658.2, and 547.3 μg/l, respectively. The essential oil also exhibited contact toxicity against L. bostrychophila with an LC 50 value of 145.5 μg/cm 2 . ( R )-Carvone, dehydroelsholtzia ketone, and elsholtzia ketone exhibited acute toxicity against the booklice with LC 50 values of 57.0, 151.5, and 194.1 μg/cm 2 , respectively. The results indicated that the essential oil and the isolated constituents have potential for the development into natural insecticides/fumigants for the control of insects in stored grains.
研究领域:
植物化学
·
昆虫学
·
天然产物研究
✓ 已验证
产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）