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
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结构生物学
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皮肤病学
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DOI
PubMed
高影响因子
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
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昆虫学
·
天然产物研究
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DOI
高影响因子
Frontiers in Plant Science
·
2022
·
IF 6.627
Shi Xia,Fang Jiaxing,Du Huicong,Zhang Sufang,Liu Fu,Zhang Zhen,Kong Xiangbo
When Ips bark beetles invade and colonize the host plants, their associated pathogenic fungal partners are carried into the phloem of the host trees. Host trees are lethally attacked by the beetle-fungus complex and the collective damage severely limits forestry production worldwide. It is of great importance to verify whether bark beetles and their associated fungi show concordant performance in terms of biology, physiology, and biochemistry on host trees. In this study, the two Ips bark beetles Ips typographus and Ips subelongatus (Coleoptera: Curculionidae, Scolytinae), their respective associated pathogenic fungi Endoconidiophora polonica and Endoconidiophora fujiensis, and their respective host plants Picea jezoensis and Larix olgensis were selected as test material. Cross-inoculation experiments were conducted indoors and outdoors to investigate the differences in reproduction and development of two beetles and infectivity of two fungi on two plants, as well as the differences in physiological responses of two plants to two fungal infections. The results showed that I. typographus and E. polonica had excellent host performance on P. jezoensis; however, neither successfully colonized and infected L. olgensis. In contrast, I. subelongatus and E. fujiensis showed strong host suitability on L. olgensis and some degree of suitability on P. jezoensis, although the host suitability of P. jezoensis for E. polonica was significantly higher than that for E. fujiensis. In addition, we found that the absolute amount of ergosterol accumulated on the lesion was positively correlated with lesion area. The ergosterol amount and lesion area were both strongly correlated with the release of host monoterpenes, but had no obvious correlation with the concentration of fungi-induced phenols on the lesion area and the side-chain oxidation of lignin in the xylem of the infected sites. Based on these results, we confirmed that “I. typographus-E. polonica” and “I. subelongatus-E. fujiensis” complexes both showed the most suitable consistent performances on their own traditional hosts, establishing a stable species-specific association relationship in these two beetle-fungus complexes, with the “I. subelongatus-E. fujiensis” complex showing broader host suitability. From the perspective of physiological responses of plants to fungal infections, monoterpenes are an important indicator of host suitability.
研究领域:
昆虫学
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植物病理学
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森林生态学
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产品关联
DOI
PubMed
高影响因子
ACS Agricultural Science & Technology
·
2024
·
IF 2.3
Jian Zhang,Yi Zhang,Shan-shan Chen,Su-xia Zhang,Yun-hai Guo,Zhen-peng Kai
Slugs pose a significant threat to agriculture, causing substantial crop damage and economic losses. Traditional molluscicides harm nontarget organisms and endanger ecosystems. Environmentally friendly molluscicides that ensure safety for humans and animals and promote sustainable agriculture are urgently needed. This study is the first to explore the fumigant toxicity, contact toxicity, and repellent effects of four monoterpenoids (geraniol, citral, geranyl nitrile, and citronellal) against Philomycus bilineatus. Compared to metaldehyde, monoterpenoids exhibited stronger contact toxicity, leading to rapid slug elimination (within 4 h), while metaldehyde caused death in slugs over a longer period of 48 h. Among the monoterpenoids, citral has weaker contact toxicity compared with the other three compounds, and geranyl nitrile (GN) and citronellal have stronger fumigant toxicity than the other two compounds. In terms of repellence and antifeeding effects, citral has the weakest toxicity. GN and citronellal stand out with excellent molluscidal activity (LC50 values of 0.10 and 0.14 g/L, respectively). The computational results based on the density functional theory (DFT) indicate that appropriate energy gaps, electrophilicity indices, and molecular softness correlate with the high molluscidal activity of monoterpenoids. From the computational results of this study, GN and citronellal, which have a moderate energy gap (approximately 0.200 eV), show the best effectiveness in controlling the slugs. In addition, unlike metaldehydes, which have a long half-life and limited biodegradability, these monoterpenoids have low toxicity and are easily degradable in the environment, making them more environmentally friendly. These findings underscore the potential of monoterpenoid compounds as eco-friendly alternatives for managing slugs in agriculture and gardens, thereby reducing reliance on traditional chemical pesticides.
研究领域:
农业科学
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环境科学
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植物保护
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DOI
高影响因子
EUROPEAN POLYMER JOURNAL
·
2019
·
IF 3.621
Longfeng Sun,Shuxi Gao,Xuefeng Gui,Lingli Liu,Kai Xu,Huan Liu
Polymer materials, with sulfur as the major part of the backbone structure, are gaining increasing importance because of the large abundance of sulfur and the unique features of polysulfide linkages for modifying material properties. Herein, we introduce polysulfides, which are synthesized from sulfur and monoterpenes, as poly-thiols platform for the crosslinking of epoxy, allowing flexible sulfur constituents incorporate into covalently linked networks. This synthesis can be conducted in a simple, mild, and practical one-pot procedure proceed smoothly in a solvent-free manner with high sulfur utilization to afford sulfur–monoterpene polysulfides (PST) with high sulfur content (up to 58%) and good solubility. The epoxy was cured with PST with imidazole as the catalyst, producing highly sulfur crosslinked thermosets, which is supposed to proceed via a thiol-epoxy reaction mechanism. The resulting thermoset perform good toughness, high transmittance and potential self-healing ability.
研究领域:
材料科学
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化学工程
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DOI
高影响因子
Foods
·
2021
·Vol. 10
·期 8
·1686
·
IF 4.35
Mostafa Gouda,Long Sheng,Rana Muhammad Aadil,Yuanyuan Liu,Meihu Ma,Xiaoli Li,Yong He,Paulo E. S. Munekata,José M. Lorenzo
Using natural multi-function phytochemicals could be one of the best solutions for clean-label production. In this study, dairy ice creams were prepared containing 14% egg yolk and 0.1% of thymol (THY), trans-cinnamaldehyde (TC), menthol (MEN), or vanillin (VAN). Then, the physical, chemical, and structural characteristics were evaluated. Magnetic resonance imaging (MRI) analysis (a rapid, chemical-free, and non-invasive tool) was carried out to evaluate the water distribution. A multivariate analysis was conducted among all studied variables. According to the results, the overrun of the MEN ice cream was significantly increased as compared to the control sample. The density was also reduced in the MEN sample. Meanwhile, the spreadability (%) of VAN was significantly increased after 6 min as compared to the control treatment. MRI analysis revealed that water distribution was significantly changed in the THY group. The firmness and viscosity of THY samples were significantly increased (p< 0.05). Multivariate analysis indicated that viscosity index and consistency were the top parameters affected by THY. The authors concluded that THY and VAN are promising stabilizers for ice-cream clean production.
研究领域:
食品科学
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生物化学
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DOI
高影响因子
Frontiers in Plant Science
·
2025
·
IF 4.8
Tingting Huang,Wenjin Men,Ariuntungalag Myanganbayar,Undarmaa Davaasambuu
Mentha arvensis L. (M. arvensis) is an aromatic plant of the Mentha genus, renowned for its medicinal and economic importance. The primary components of its essential oils (EOs) are monoterpenoids, synthesized and stored in peltate glandular trichomes (PGTs). In general, the EO content in M. arvensis is relatively low. Methyl jasmonate (MJ) has been reported as an effective elicitor of terpenoid biosynthesis in medicinal plants, but the specific mechanisms underlying MJ’s influence on M. arvensis remain unclear. In this study, exogenous application of MJ significantly increased the EO content, yield, and PGT density in a dose-dependent manner. At a 5 mM dose, the EO content and PGT density peaked, with increases of 71.20% and 53.69%, respectively. Gas chromatography-mass spectrometry (GC-MS) analysis indicated that, in general, MJ treatment did not significantly alter the types or relative proportions of EO components of M. arvensis. However, L-menthol content decreased slightly by 7.90% under 5 mM MJ treatment. Transcriptome analysis identified 4,659 differentially expressed genes (DEGs) in MJ-treated leaves. KEGG enrichment analysis revealed that “Monoterpenoid biosynthesis” was among the most significantly enriched metabolic pathways. Key genes involved in jasmonic acid (JA) signaling (JAZs and MYCs) and monoterpenoid biosynthesis (GPPSs, LSs, L3Hs, and IPRs) were significantly up-regulated. Co-expression analysis, promoter binding element analysis and weighted gene co-expression network analysis (WGCNA) indicated that transcription factors (TFs) such as AP2/ERF, WRKY, MYB, and bHLH play crucial roles in regulating MJ-mediated monoterpenoid biosynthesis. Several key candidate TFs potentially involved in regulating monoterpenoid biosynthesis in M. arvensis were identified. These findings provide valuable insights into the molecular mechanisms regulating monoterpenoid accumulation in the Mentha genus.
研究领域:
植物学
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分子生物学
·
药用植物研究
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产品关联
DOI
PubMed
高影响因子
BIORESOURCE TECHNOLOGY
·
2025
·
IF 9
Yapeng Zhang,Zhidong Ma,Wenqiang Li,Chenwen Liu,Huipeng Gao,Meng Wang,Lanpeng Li,Quan Zhang,Bo Lv,Lei Qin,Chun Li
Pinene is a plant volatile monoterpenoid which is used in the fragrance, pesticide, and biofuel industries. Although α-pinene has been synthesized in microbial cell factories, the low synthesis efficiency has thus far limited its production. In this study, the cell growth and α-pinene production of the engineered yeast were decoupled by a dynamic regulation strategy, resulting in a 101.1-fold increase in α-pinene production compared to the control. By enhancing the mevalonate pathway and expanding the cytosolic acetyl-CoA pool, α-pinene production was further increased. Overexpression of the transporter Sge1 resulted in a redistribution of global gene transcription, leading to an increased flux of α-pinene synthesis. By optimizing the aeration flow rate in 3-L bioreactors, the α-pinene production reached 1.8 g/L, which is the highest reported α-pinene production in cell factories. Our research provides insights and fundamentals for the efficient synthesis of monoterpenoids in microbial cell factories.
研究领域:
生物工程
·
代谢工程
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产品关联
DOI
PubMed
高影响因子
CHEMISTRY-A EUROPEAN JOURNAL
·
2023
·Vol. 30
·期 10
·e202302936
·
IF 4.3
Feiyan Yuan,Jing Ding,Yiyang Sun,Jianhua Liang,Yunzi Luo,Yang Yu
Graphical The carbene transfer reaction was realized in the biosynthetic pathway. Using L-limonene as the precursor, L-carveol was biotransformed by P411-PFA to generate unnatural terpenoid derivatives with trifluoromethyl group. Protein engineering of cytochrome P450s has enabled these biocatalysts to promote a variety of abiotic reactions beyond nature‘s repertoire. Integrating such non-natural transformations with microbial biosynthetic pathways could allow sustainable enzymatic production of modified natural product derivatives. In particular, trifluoromethylation is a highly desirable modification in pharmaceutical research due to the positive effects of the trifluoromethyl group on drug potency, bioavailability, and metabolic stability. This study demonstrates the biosynthesis of non-natural trifluoromethyl-substituted cyclopropane derivatives of natural monoterpene scaffolds using an engineered cytochrome P450 variant, P411-PFA. P411-PFA successfully catalyzed the transfer of a trifluoromethyl carbene from 2-diazo-1,1,1-trifluoroethane to the terminal alkenes of several monoterpenes, including L-carveol, carvone, perilla alcohol, and perillartine, to generate the corresponding trifluoromethylated cyclopropane products. Furthermore, integration of this abiotic cyclopropanation reaction with a reconstructed metabolic pathway for L-carveol production in Escherichia coli enabled one-step biosynthesis of a trifluoromethylated L-carveol derivative from limonene precursor. Overall, amalgamating synthetic enzymatic chemistry with established metabolic pathways represents a promising approach to sustainably produce bioactive natural product analogs.
研究领域:
生物化学
·
合成生物学
·
药物化学
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DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2025
·
IF 6.2
Haowen Huang,Cong Huang,Qingwen Fang,Yuhan Wu,Yuhuan Kuang,Ji Zhang,Guorong Fan,Zongde Wang,Shangxing Chen,Dayong Peng
In the fields of agriculture and forestry, there are major unknown risks associated with the toxicity of chemical pesticide residues and pathogen resistance. To address this issue, in this study, 52 novel pyrazole monoterpene compounds were obtained by organic synthesis of highly active monoterpene natural products and evaluated for their in vitro and in vivo antifungal activities and crystal structure analysis of compound 5b. The results showed that compounds 4g and 8f exhibited remarkable antifungal activities against Rhizoctonia solani, with the corresponding EC50 values reaching 4.27 and 4.81 mg/L. At the same time, the results of in vivo and in vitro experiments showed that both compounds 4g and 8f had good control effects against rice sheath blight. The antifungal activity of these compounds was preliminarily explored by scanning electron microscopy, molecular docking, enzyme activity determination, and cytotoxicity, indicating that these compounds have the potential for development into low-toxic antifungal drugs.
研究领域:
植物保护
·
药物化学
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DOI
PubMed
高影响因子
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS
·
2024
·
IF 2.5
Yiyang Sun,Yinian Tang,Jing Zhou,Bingchen Guo,Feiyan Yuan,Bo Yao,Yang Yu,Chun Li
Carbene transfer reactions have emerged as pivotal methodologies for the synthesis of complex molecular architectures. Heme protein-catalyzed carbene transfer reactions have shown promising results on model compounds. However, their limited substrate scope has hindered their application in natural product functionalization. Building upon the foundation of previously published work on a carbene transferase-myoglobin variant, this study employs computer-aided protein engineering to design myoglobin variants, using either docking or the deep learning-based LigandMPNN method. These variants were utilized as catalysts in carbene transfer reactions with a selection of monoterpene substrates featuring C–C double bonds , leading to seven target products. This cost-effective methodology broadens the substrate scope for heme protein-catalyzed reactions, thereby opening novel pathways for research in heme protein functionalities and offering fresh perspectives in the synthesis of bioactive molecules.
研究领域:
生物化学
·
蛋白质工程
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DOI
PubMed
高影响因子
JOURNAL OF MOLECULAR STRUCTURE
·
2024
·
IF 4
Yuan Zhong,Cong Huang,Jing Zhang,Liang Zhong,Rong Zeng,Yuhuan Kuang,Xinyan Ye,Ziyin Xie,Ji Zhang,Zongde Wang,Shangxing Chen,Dayong Peng
Succinate dehydrogenase inhibitors (SDHI) are widely used in plant antifungal agents. To break the barrier of resistance, a series of new coumarin-quinolinamide SDHI derivatives containing monocyclic monoterpenes were designed and synthesized using natural camphor or natural menthol as lead compounds, and their structures were characterized by FT-IR, 1 H NMR, 13 C NMR and HRMS. In vitro antifungal activity test results showed that the target compounds had inhibitory activity against most plant pathogenic fungi, especially against Rhizoctonia solani and Phytophthora nicotianae var. nicotianae , which was superior to other fungi. Among them, compounds 11t and 12t showed better inhibitory effects on Rhizoctonia solani than the commercial fungicide tricyclazole, with EC 50 of 16.90 mg/L and 27.09 mg/L, respectively. Based on this, the detached leaf assay was used to further explore the in vivo therapeutic and preventive effects of compounds 11t and 12t on rice sheath blight in plants. The results of the antifungal activity test in vivo showed that compound 11t was slightly better than the positive control, while compound 12t was close to the control effect of azoxystrobin. More importantly, the more bioactive compounds 11t and 12t did not affect the germination of cowpea seeds and also did not affect the growth of normal human hepatocytes and kidney cells. Molecular docking experiments showed that the introduction of the diethylamino group could promote the formation of hydrogen bonds between the hydrogen atom on the amide bond of the target compound and residue Tyr91, and compounds 11t and 12t had smaller free energy between the amino acid residue, which would enhance the antifungal activity of the compounds. These studies proved the potential value of this series of compounds for the study of novel amide-based SDHI fungicides.
研究领域:
植物学
·
药理学
·
分子生物学
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DOI
高影响因子
危险品化学品经营许可证（带存储）