PLANT JOURNAL
·
2024
·Vol. 120
·期 2
·658-673
·
IF 6.2
Yingmei Wu,Xueqing Chen,Fuhua Hao,Yu Liu,Wei Luo,Yaru Zhu,Li Li,Fei Han,Yunluo Zhang,Ying Jiang,Xingyao Xiong,Dae-Kyun Ro,Yi Shang,Sanwen Huang,Junbo Gou
SUMMARY Presilphiperfolane-type sesquiterpenes represent a unique group of atypical sesquiterpenoids characterized by their distinctive tricyclic structure. They have significant potential as lead compounds for pharmaceutical and agrochemical development. Herein, we utilized a transcriptomic approach to identify a terpene synthase (TPS) gene responsible for the biosynthesis of rare presilphiperfolane-type sesquiterpenes in Inula lineariifolia , designated as IlTPS1 . Through phylogenetic analysis, we have identified the evolutionary conservation of key motifs, including RR(x)8W, DDxxD, and NSE/DTE in IlTPS1, which are shared with other tricyclic sesquiterpene synthases in the TPS-a subfamily of Asteraceae plants. Subsequent biochemical characterization of recombinant IlTPS1 revealed it to be a multiproduct enzyme responsible for the synthesis of various tricyclic sesquiterpene alcohols from farnesyl diphosphate (FPP), resulting in production of seven distinct sesquiterpenes. Mass spectrometry and nuclear magnetic resonance (NMR) spectrometry identified presilphiperfolan-8β-ol and presilphiperfol-7-ene as predominant products. Furthermore, biological activity assays revealed that the products from IlTPS1 exhibited a potent antifungal activity against Nigrospora oryzae . Our study represents a significant advancement as it not only functionally identifies the first step enzyme in presilphiperfolane biosynthesis but also establishes the heterologous bioproduction of these unique sesquiterpenes.
研究领域:
植物生物化学
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系统发育学
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生物技术
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药理学
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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
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微生物学
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植物科学
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产品关联
DOI
PubMed
高影响因子
BIOORGANIC CHEMISTRY
·
2022
·
IF 5.307
Hanjing Liang,Qingmei Feng,Hui Guo,Jiangnan Lv,Lingxia Zhang,Qingxia Li,Jun Chi,Qiuyan Liu,Zhimin Wang,Liping Dai
Nine new cadinane-type sesquiterpenoids ( 1 – 9 ) and three new eucalyptane -type sesquiterpenes ( 10 – 12 ) were isolated from the ethyl acetate extract of Burdock leaves, which were commonly used for preventing or treating atherosclerosis in China. Their structures were confirmed by extensive spectroscopic analysis, single-crystal X-ray diffraction analysis and ECD calculations. Compound 1 possessed the rare large conjugated skeleton. All the isolates were evaluated for anti-inflammatory and cholesterol-lowering activities by the LPS- and oxidized-low-density-lipoprotein-stimulated RAW 264.7 cells, respectively. As the results, all isolates could decrease the productions of NO, and down-regulate the accumulation of cholesterol. Among them, 4 showed the most potent cholesterol-lowering effect. For the high content of 4 in the herb, mechanistic study of 4 was performed and the results showed that 4 markedly reduced the release of pro-inflammatory mediators which was probably associated with inhibition of the PI3K/Akt and 5-LOX signaling pathways. The findings of this study demonstrated the anti-inflammatory/cholesterol-lowering effects of the new sesquiterpenes from burdock leaves, which provides chemical basis and scientific evidence for the herb used as anti-atherosclerosis agents for the further study. The sesquiterpene lactones of burdock leaves are expected to become new small molecule inhibitors for the treatment of AS .
研究领域:
药理学
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化学
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分子生物学
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植物科学
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产品关联
DOI
PubMed
高影响因子
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
·
2024
·
IF 3.8
Shufen Wang,Jinrou Wei,Hongzhao Xie,Xiaopeng Chen,Jie zhen Liang,Xiaojie Wei,Jie Huang,Linlin Wang
The phase equilibrium relationships of resin systems are indispensable for resin tapping, distillation, and investigating the release of terpenes in biogenic volatile organic compounds (BVOCs). Herein, we obtained the vapor–liquid equilibrium (VLE) data of monoterpene-sesquiterpene systems that contain resin acid by a headspace gas chromatography (HS-GC). There is no azeotropic behavior between terpenes, and abietic acid was found to inhibit the volatilization and separation of terpenes. Furthermore, the saturated vapor pressure of the systems almost triples when the experimental temperature increases from 313.15 to 333.15 K, which may exacerbate terpene emissions in ecosystems. Additionally, the thermodynamic consistency of the VLE values was confirmed by van Ness test, and the experimental data were correlated using NRTL, UNIQUAC, and Wilson activity coefficient models, while the Conductor-like Screening Model for Real Solvents (COSMO-RS) model was utilized for predictions. All of the data satisfy thermodynamic consistency, and the correlation results and prediction results demonstrate good adherence of the activity coefficient models to experimental values and the positive capacity of COSMO-RS in predicting the VLE relationship for the pine resin systems, respectively.
研究领域:
生态学
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化学工程
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植物学
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产品关联
DOI
高影响因子
Journal of Essential Oil Bearing Plants
·
2019
·
IF 0.688
Fengying Qiu,Haikuan Yang,Ting Zhang,Xindong Wang,Shifang Wen,Xiaohua Su
Cinnamomum porrectum (Roxb.) Kosterm is an important plant which produces natural essential oil. In this study, essential oil was hydro-distilled from leaves of five different samples of C. porrectum which were randomly selected in a C. porrectum forest in Guangdong Province of China, and identified by Gas Chromatography Mass Spectrometry (GC/MS). The results revealed that the average yield of essential oil was 1.12 % (v/w). A total of 65 compounds were identified from five samples, and 31 of which were reported for the first time in leaf essential oil of C. porrectum. High contents of monoterpenes and sesquiterpenes were found in the leaves of C. porrectum. The main components of essential oil were linalool (79.4 %), elemol (38.1 %), eucalyptol (35.6 %), β-caryophyllene (34.6 %), camphor (33.2 %), α-eudesmol (26.5 %), citral (23.5 %) and L-α- Terpineol (22.0 %). Different types of high-value compounds were found to be present in the five selected samples of C. porrectum oil, and the difference of essential oil components in individual leaves was remarkable. The various breeding techniques can be utilization based on different chemical types of leaf essential oil to exploit the plant to its full potential.
研究领域:
植物学
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化学生态学
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药用植物研究
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DOI
高影响因子
Frontiers in Bioengineering and Biotechnology
·
2021
·
IF 5.89
Fu Xueqing,Zhang Fangyuan,Ma Yanan,Hassani Danial,Peng Bowen,Pan Qifang,Zhang Yuhua,Deng Zhongxiang,Liu Wenbo,Zhang Jixiu,Han Lei,Chen Dongfang,Zhao Jingya,Li Ling,Sun Xiaofen,Tang Kexuan
Terpenes constitute the largest class of secondary metabolites in plants. Some terpenes are essential for plant growth and development, membrane components, and photosynthesis. Terpenes are also economically useful for industry, agriculture, and pharmaceuticals. However, there is very low content of most terpenes in microbes and plants. Chemical or microbial synthesis of terpenes are often costly. Plants have the elaborate and economic biosynthetic way of producing high-value terpenes through photosynthesis. Here we engineered the heterogenous sesquiterpenoid patchoulol production in A. annua. When using a strong promoter such as 35S to over express the avian farnesyl diphosphate synthase gene and patchoulol synthase gene, the highest content of patchoulol was 52.58 μg/g DW in transgenic plants. When altering the subcellular location of the introduced sesquiterpene synthetase via a signal peptide, the accumulation of patchoulol was observably increased to 273 μg/g DW. This case demonstrates that A. annua plant with glandular trichomes is a useful platform for synthetic biology studies.
研究领域:
植物学
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合成生物学
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药用植物遗传工程
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产品关联
DOI
PubMed
高影响因子
Organic Chemistry Frontiers
·
2021
·Vol. 8
·期 6
·1249-1256
·
IF 5.281
Li-Hua Su,Tian-Ze Li,Chang-An Geng,Yun-Bao Ma,Xiao-Yan Huang,Jin-Ping Wang,Xue-Mei Zhang,Ji-Jun Chen
Two sesquiterpenoid trimers, artematrotrimers A (1) and B (2), and two sesquiterpenoid dimers, artematrodimers A (3) and B (4), possessing unprecedented scaffolds with a methylene-bridged connection were identified from Artemisia atrovirens. Their structures and absolute stereochemistry were determined by comprehensive spectroscopic data, single-crystal X-ray diffraction analyses, and ECD calculations. Compounds 1–4 represent a new type of sesquiterpenoid oligomers featuring the connections between hetero sesquiterpenoid units via one or two C–C bonds. A possible biosynthetic pathway for 1–4 was also proposed. Compound 3 showed obvious cytotoxicity against HepG2 and Huh7 cell lines with IC50 values of 21.9 and 22.6 μM, respectively.
研究领域:
植物化学
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药理学
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肿瘤学
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DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2025
·
IF 6.2
Haichun Zeng,Beilin Meng,Jiatong Zeng,Li Rao
Sesquiterpenes, a structurally diverse class of natural products, play pivotal roles in the pharmaceutical, fragrance, and flavor industries. In this study, we first identified and functionally characterized a multifunctional sesquiterpene synthase, ChTPS6, from the plant-pathogenic fungus Cochliobolus heterostrophus. When incubated with FPP, ChTPS6 primarily catalyzed the formation of cubebol as the main product, which is widely used as a sustained cooling and refreshing agent in the food industry. Remarkably, ChTPS6 exhibited substrate promiscuity, efficiently utilizing GPP and GGPP as alternative substrates. Moreover, through protein modeling and site-directed mutagenesis, we pinpointed key amino acid residues essential for the catalytic activity of ChTPS6, and successfully re-engineered the enzyme to alter its product specificity. These findings provide novel insights into the catalytic mechanism and functional versatility of ChTPS6 while broadening its potential applications in the biosynthesis of valuable sesquiterpenes.
研究领域:
生物化学
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分子生物学
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真菌学
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产品关联
DOI
PubMed
高影响因子
FITOTERAPIA
·
2019
·
IF 2.431
Fenqin Zhao,Qianqian Zhang,Yan Yan,Haiyan Jia,Xinran Zhao,Xiying Li,Lihua Zheng,Guang Han
Dendranthema morifolium cv. ‘jinsidaju’, cultivated only in Kaifeng, has been eaten for more than 1000 years. During the antioxidant-activity-guided studies on its chemistry and health care function, two new bisabolane-type sesquiterpenes , (6 R ,7 R )-7-hydroxybisabol-2,9 E ,11-triene-4-one (jinsidajuol A, 1 ) and (6 R ,7 R )-7-hydroxy-11-methoxybisabol-2,9 E -diene-4-one (jinsidajuol B, 2 ), and thirteen known compounds ( 3 – 15 ) were isolated from the flowers. Their structures were elucidated by 1D and 2D NMR spectroscopy and HRMS. 1 and 2 are the first example of bisabolane-type sesquiterpenes isolated from the genus Dendranthema. Compounds 6 – 8 , 12 and 13 exhibited strong scavenging activities on the ABTS radical cation with IC 50 3.33, 5.67, 2.00, 2.50, 5.33 μg/mL, respectively. The IC 50 values of all compounds on HepG2 human hepatoma tumor cell line were higher than 50 μM.
研究领域:
药用植物学
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生物化学
·
植物化学
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产品关联
DOI
PubMed
高影响因子
PHYTOCHEMISTRY
·
2023
·
IF 3.8
Song Ang,Chun Liu,Peng Hong,Lei Yang,Gui'e Hu,Xi Zheng,Jingwei Jin,Rihui Wu,Wing-Leung Wong,Kun Zhang,Lishe Gan,Dongli Li
Four previously undescribed hirsutinolide-type sesquiterpenoids , cyanolides A-D ( 1 – 4 ), along with twelve known analogues ( 5 – 16 ), were isolated from the aerial parts of Cyanthillium cinereum . Their structures were determined by comprehensive analysis of NMR, HRESIMS, and ECD spectra. Compound 1 is a rarely occurring hirsutinolide-type sesquiterpenoid with 1,4-ether ring ruptured and containing a chlorine atom , and compounds 13 – 16 were reported from this plant for the first time. All compounds were tested for their inhibiting effects on prostate cancer cells. As a result, compounds 1 , 3 , and 8 – 14 exhibited significant anti-prostate cancer activity against PC-3 and LNCaP cells with IC 50 values ranging from 2.2 ± 0.4 to 8.5 ± 0.7 μM and 3.0 ± 0.7 to 10.5 ± 1.1 μM, respectively. The preliminary structure-activity relationship was discussed. Further investigation showed that compound 1 induced apoptosis in PC-3 cells.
研究领域:
植物化学
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肿瘤学
·
药理学
✓ 已验证
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2021
·
IF 5.279
Lin Li-Bin,Jian Xiao,Qiang Zhang,Rui Han,Biao Xu,Sheng-Xiang Yang,Wen-Bo Han,Jiang-Jiang Tang,Jin-Ming Gao
Fourteen eremophilane sesquiterpenoids (1–14), including nine new congeners, septoreremophilanes A–I (1–9), together with three known sesquiterpenes (15–17), two known tetralone derivatives (18, 19), and two known cholesterol analogues (20, 21), were isolated from the endophytic fungus Septoria rudbeckiae. Compounds 1–6 and 7a belong to the family of the highly oxygenated eremophilane sesquiterpenoids with a 6/6/5 tricyclic system and bearing a hemiacetal moiety. The inhibitions of all metabolites against eight bacteria were estimated in vitro, and nine new metabolites (1–9) were tested for antineuroinflammatory activity. Notably, the effects of 4 against Pseudomonas syringae pv. actinidae and 20 against Bacillus cereus displayed potent inhibitory, with the MIC values of 6.25 and 6.25 μM, respectively. Further, scanning electron microscopy analyses indicated that 4 and 20 were to change the outer configuration of bacterial cells, respectively, and the investigations demonstrated that 4 and 20 may act as potential structure templates for the development of the agrochemical bactericides. Additionally, compound 6 displayed potent inhibition of NO generation in lipopolysaccharide-induced BV-2 microglial cells (IC50 = 12.0 ± 0.32 μM), and the conceivable anti-inflammatory mechanisms implicated were also investigated by molecular docking. Thus, the bioactive metabolites of the strain S. rudbeckiae may serve as a novel resource to be developed.
研究领域:
微生物学
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天然产物化学
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药理学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2014
·
IF 3.107
Dong-Mei Wang,Cheng-Chen Zhang,Qiang Zhang,Nusrat Shafiq,Gennaro Pescitelli,Deng-Wu Li,Jin-Ming Gao
Five new sesquiterpene polyol esters with a dihydro-β-agarofuran skeleton, designated as wightianines A–E (1–5), besides two known compounds, were isolated from the methanolic extract of the whole plant of the traditional herbal medicine Parnassia wightiana Wall. The structures of the isolated compounds were elucidated on the basis of spectroscopic analyses, including two-dimensional nuclear magnetic resonance techniques (correlation spectroscopy, heteronuclear multiple-quantum coherence, nuclear Overhauser effect spectrometry, and heteronuclear multiple-bond correlation) and electronic circular dichroism studies. The antifungal and insecticidal activities of five compounds were evaluated against several plant pathogenic fungi and armyworm larvae (Mythimna separata Walker). Among the test metabolites, compounds 2 and 7 both exhibited potent antifungal activity against the phytopathogenic fungus Cytospora sp. with minimum inhibitory concentration values of 0.78 μg/mL, which are equal to the two positive controls, hymexazol and carbendazim. However, no insecticidal activity of the test compounds was observed in the present study. Compounds 2 and 7 could be promising leads for developing new fungicides against agriculturally important fungus Cytospora sp.
研究领域:
植物化学
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药理学
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农业科学
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产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）