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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2024 · IF 5.7

Identification and Characterization of a Fungal Monoterpene Synthase Responsible for the Biosynthesis of Geraniol

Haichun Zeng,Jiatong Zeng,Beilin Meng,Jianmei Peng,Li Rao

Geraniol, an acyclic monoterpenoid of substantial value extracted from the essential oils of various aromatic plants, holds significant commercial and industrial importance in the realms of food, cosmetics, medicine, and bioenergy. Geraniol synthase, which is responsible for geraniol production, has been identified in only several plant species to date. Here, we present the first cloning and characterization of a geraniol synthase (PgfTPS) from Penicillium griseofulvum. This enzyme demonstrates pronounced specificity in catalyzing the conversion of geranyl diphosphate into geraniol. Moreover, through protein modeling and site-directed mutagenesis, we have identified key active-site residues crucial for the catalytic function of PgfTPS. Finally, we utilized engineered Saccharomyces cerevisiae as a host for PgfTPS expression to facilitate geraniol production. Our findings not only advance the development of efficient biocatalysts for geraniol generation but also establish a fundamental basis for further exploration into fungal monoterpene biosynthesis.

CAS / MDL: 106-24-1
研究领域: 生物化学 · 微生物学 · 植物代谢工程
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PEST MANAGEMENT SCIENCE · 2024 · IF 3.8

Enhancing agrochemical delivery in citrus leaves with geraniol: a promising strategy for controlling huanglongbing (HLB)

Shuning Chen,Ao Yuan,Huafeng Wang,Daibin Yang,Li Cui,Fengjiao Hao,Xiaojing Yan,Huizhu Yuan

BACKGROUND Citrus huanglongbing (HLB) is a devastating disease in citrus, caused by Candidatus Liberibacter asiaticus (CLas), which primarily resides in the phloem where chemicals cannot effectively reach, posing a significant challenge in controlling HLB. To address these challenges, plant essential oils (EOs), widely used as transdermal enhancers and known for their benefits for plant tissues, were investigated for their potential to enhance chemical permeation. RESULTS In this study, seven EOs – eugenol, carvacrol, eucalyptol, geraniol, linalool, cinnamaldehyde, and d -limonene – were evaluated for their potential to enhance chemical penetration into citrus leaves. Preliminary screening with tracer methods revealed that geraniol provided the greatest enhancement of permeation, achieving the deepest and broadest distribution into the spongy tissue of the citrus leaf. The permeation levels of rhodamine B and crystal violet through the cuticular layer were elevated from 0.55 mg L −1 and 0.11 mg L −1 to 20.04 mg L −1 and 7.14 mg L −1 , respectively, by the addition of geraniol. Further validation through high-performance liquid chromatography–mass spectrometry (HPLC–MS) confirmed that the penetration of fludioxonil and tetracycline into citrus leaf tissues was enhanced by 15.07-fold and 20.43-fold, respectively. In planta experiments confirmed that adding geraniol to tetracycline and oxytetracycline via foliar application eliminated CLas bacteria in HLB-affected citrus more efficiently than controls. CONCLUSION Our study underscores the potential of geraniol as an effective EO-based permeation enhancer for combating HLB. By significantly improving the delivery and efficacy of bactericidal treatments, geraniol offers a promising strategy for managing this catastrophic citrus disease, potentially transforming the approach to controlling HLB. © 2024 Society of Chemical Industry.

研究领域: 植物病理学 · 农业化学 · 植物化学
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CARBOHYDRATE RESEARCH · 2026 · IF 3.4

Phenylboronic acid and geraniol co-modified chitosan oligosaccharide derivatives boost antibacterial efficacy by targeting bacteria

Wenting Shi,Rui Li,Yan Fang,Zhangqi Huang,Lin Yue,Imran Mahmood Khan,Zhouping Wang

Chitosan oligosaccharide (COS) derivatives present significant potential as antimicrobial agents. Our previously developed geraniol (Ger) grafted Chitosan oligosaccharide (COS-Ger) has demonstrated commendable solubility and antibacterial activity. To further improve its effectiveness, exploring methods for bacterial targeting could be a beneficial approach. Therefore, we herein report a novel dual-functional derivative, phenylboronic acid (PBA) and Ger co-modified COS, by strategically integrating PBA into the COS-Ger framework. The molecular structure of the derivative has been validated through several characterization techniques. Biological evaluations demonstrated that PBA incorporation synergistically enhanced the compound's bacterial targeting, resulting in markedly improved antibacterial performance. PBA incorporation synergistically enhanced the compound's bacterial targeting. Specifically, at a low concentration of 0.2 mg/mL, the inhibition rate of PBA–COS–Ger against Staphylococcus aureus ( S. aureus ) reached 73.10%, significantly outperforming that of COS-Ger (30.61%). Moreover, it achieved nearly 100% inhibition against both S. aureus and Escherichia coli ( E. coli ) at 1.0 mg/mL. These results clearly indicate that the grafting of PBA greatly enhanced the antibacterial ability of COS-Ger. The practical potential of this derivative was preliminarily verified through a preservation experiment on cherry tomatoes. This approach establishes a conceptual platform for the rational design of highly efficient, bio-based antimicrobial agents.

CAS / MDL: 106-24-1
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FITOTERAPIA · 2019 · IF 2.431

Geraniol targets KV1.3 ion channel and exhibits anti-inflammatory activity in vitro and in vivo

Chen-Jun Ye,Sheng-An Li,Yun Zhang,Wen-Hui Lee

Naturally occurring monoterpenes are known for their various pharmacological activities including anti-inflammation. K V 1.3 ion channel is a voltage-gated potassium channel and has been validated as a drug target for autoimmune and chronic inflammatory diseases like psoriasis . Here we experimentally test the direct interaction between monoterpenes and K V 1.3 ion channel. Our electrophysiological analysis determined that monoterpenes (geraniol, nerol , β-citronellol, citral and linalool) have inhibitory effects on K V 1.3 ion channel. Representatively, geraniol reversibly blocked K V 1.3 currents in a voltage-dependent manner with an IC 50 of 490.50 ± 1.04 μM at +40 mV in HEK293T cells. At the effective concentrations, geraniol also inhibited cytokine secretion of activated human T cells, including IL-2, TNF-α and IFN-γ. In an imiquimod-induced psoriasis-like animal model, geraniol administration significantly reduced psoriasis area and severity index scores, ameliorated the deteriorating histopathology and decreased the degree of splenomegaly . Together, our findings not only suggest that monoterpenes may serve as lead molecules for the development of K V 1.3 inhibitors, but also indicate that geraniol could be considered as a promising therapeutic candidate to treat autoimmune diseases.

CAS / MDL: 106-22-9
研究领域: 药理学 · 免疫学 · 炎症研究 · 药物开发
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PACKAGING TECHNOLOGY AND SCIENCE · 2017 ·Vol. 30 ·期 9 ·587-600 · IF 1.32

EVOH Films Containing Antimicrobials Geraniol and α-Terpilenol Extend the Shelf Life of Snakehead Slices

Haili Wang,Chunxiang Yang,Jing Wang,Mo Chen,Donglei Luan,Li Li

Various studies have provided information on active packaging to prevent food putrefaction effectively . In this work, ethylene–vinyl alcohol copolymer (EVOH) films with geraniol (Ger) and α-terpilenol (Ter) were successfully prepared by extrusion. The mechanical, thermal, oxygen barrier and antimicrobial properties of the packaging films were characterized, and the application of the films in snakehead preservation was examined. Thermogravimetric analysis showed that the addition of Ger and Ter did not decrease the films properties but improved their oxygen barrier property and thermostability. Moreover, the incorporation of Ger and Ter inhibited the growth of Escherichia coli , Salmonella enterica and Listeria monocytogenes . Both of the films, EVOH/Ger (EVOH/Ger) and EVOH/Ter (EVOH/Ter), reduced Salmonella enterica by 2.36 ± 0.17 and 1.91 ± 0.06 log units, respectively. Meanwhile, the effects of EVOH/Ger and EVOH/Ter on quality assessment of snakehead slices were examined through sensory tests and analyses of biochemical indices during refrigerated storage (4°C ± 1°C) for 10 days. Sensory properties, total viable counts, total volatile basic nitrogen, thiobarbituric acid and pH values were evaluated. On eight day, compared with the control fish samples, the total viable counts and total volatile basic nitrogen values cut down 1.98 ± 0.02 log units and 11.3 ± 0.11 mgN/100 g, respectively, for fish samples packaged by EVOH/Ger. The active films containing 6% (wt) Ger and 6% (wt) Ter inhibited the growth of E. coli , S. enterica and L. monocytogenes and effectively extended shelf life by 4–5 days under cold-storage conditions compared with the control group. Copyright © 2017 John Wiley & Sons, Ltd.

CAS / MDL: 7440-27-9
研究领域: 食品科学 · 包装工程
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International Journal of Nanomedicine · 2024 · IF 6.6

Targeted Delivery of Geraniol via Hyaluronic Acid-Conjugation Enhances Its Anti-Tumor Activity Against Prostate Cancer

Han Yu,Na Ning,Fujin He,Jiao Xu,Han Zhao,Shaofeng Duan,Yunqi Zhao

Background Targeted delivery systems have been developed to improve cancer treatment by reducing side effects and enhancing drug efficacy. Geraniol, a natural product, has demonstrated promising anti-cancer effects in various cancer types, including prostate cancer, which is the most commonly diagnosed cancer in men. Hyaluronic acid (HA), a natural carrier targeting CD44-positive prostate cancer cells, can be utilized in a targeted delivery system.Purpose This study investigated the efficacy of a conjugate of HA and geraniol linked via a disulfide bond linker (HA-SS-Geraniol) in prostate cancer.Materials and Methods The cytotoxicity of HA-SS-Geraniol was evaluated on human PC-3 prostate cancer cells. Flow cytometry was used to assess its effects on mitochondrial membrane potential, apoptosis, and cell cycle arrest. Additionally, proteomic analysis was conducted to explore the underlying mechanism of action induced by HA-SS-Geraniol treatment. A subcutaneous xenograft tumor model was established in nude mice to evaluate the toxicity and efficacy of HA-SS-Geraniol in vivo.Results The results demonstrated that HA-SS-Geraniol exhibited potent cytotoxicity against PC-3 prostate cancer cells by inducing mitochondrial membrane potential loss and apoptosis in vitro. The proteomic analysis further supported the hypothesis that HA-SS-Geraniol induces cell death through mitochondria-mediated apoptosis, as evidenced by differential protein expression. The in vivo mouse model confirmed the safety of HA-SS-Geraniol and its ability to inhibit tumor growth.Conclusion HA-SS-Geraniol holds promise as a biologically safe and potentially effective therapeutic agent for prostate cancer treatment. Its targeted delivery system utilizing HA as a carrier shows potential for improving the efficacy of geraniol in cancer therapy.

CAS / MDL: 106-24-1
研究领域: 癌症研究 · 药学 · 分子生物学 · 药物递送系统
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ACS Food Science & Technology · 2024 · IF 2.6

Contactless and Biosafe Freshness Protection Package Consists of Geraniol@β-cyclodextrin MOF Complex for Emperor Banana Storage

Haoran Bai,Liying Yang,Zheng Li,Douxin Xiao,Alideertu Dong

The infestation of pathogenic microorganisms leads to a decline in fruit quality and reduces their storage time. The existing methods for contact preservation suffer from the issue of migration of harmful ingredients, thus necessitating the development of novel preservation techniques. The present study focuses on the development of a contactless and biosafe solid preservative (GR@β-CD-MOF) by incorporating geraniol (GR, essential oil) into the β-cyclodextrin MOF (β-CD-MOF). The loading rate of geraniol was 210.8 mg/g. The morphology and structure of GR@β-CD-MOF were characterized using SEM, XRD, XPS, and FTIR. Furthermore, we evaluated the in vitro antimicrobial activity of GR@β-CD-MOF against three common food-borne pathogens Escherichia coli (E. coli), Staphylococcus aureus (S. aureus), and Botrytis cinerea (B. cinerea). Subsequently, the GR@β-CD-MOF was placed into poly(lactic acid) bags to prepare a solid preservative for emperor bananas. In comparison with the control group, the emperor bananas treated with GR@β-CD-MOF exhibited lower decreases in relevant physicochemical parameters including color, weight loss, and soluble solids content. Moreover, the shelf life of emperor bananas was extended up to 8 days. These findings validate the efficacy of GR@β-CD-MOF as a solid preservative for fruit preservation.

CAS / MDL: 7585-39-9 106-24-1
研究领域: 食品科学 · 微生物学 · 材料科学
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DRUG DELIVERY · 2026 · IF 8

A macrophage-mimetic nanocarrier co-loaded with geraniol and FK13-a1 for MRSA-induced acute lung injury

Haonan Li,Binghong Xu,Junguang Liang,Tao Hu,Tingting Wu,Liqin Lai,Xuan Zou,Ziquan Lv,Xiangjie Yao,Xiaobao Jin,Yinghua Xu,Shuiqing Gui,Xuemei Lu

Current clinical strategies for Methicillin-resistant Staphylococcus aureus (MRSA)-induced acute lung injury (ALI) predominantly focus on single-approach interventions such as anti-inflammatory therapy. However, due to the complex, multi-pathway pathological network underlying the disease, targeting a single pathway often yields suboptimal therapeutic outcomes. Consequently, there is a pressing need to develop innovative drug delivery systems capable of systematically addressing this intricate pathological process. Geraniol, a naturally derived monoterpene alcohol, exhibits multiple pharmacological activities including antimicrobial, antioxidant, and organ-protective effects, while the antimicrobial peptide (AMP) FK13-a1 demonstrates broad-spectrum antibacterial, anti-inflammatory, and immunomodulatory functions. Recognizing their complementary mechanisms of action, we innovatively propose a synergistic therapeutic strategy combining geraniol with FK13-a1. To enhance targeting precision, we engineered a biomimetic delivery system by coating nanomaterials with macrophage membranes via tyramine linkage, enabling specific homing to pulmonary inflammatory sites. Guided by this design concept, we successfully fabricated the biomimetic nanodrug Tyr-MM@PLGA/G+F and conducted systematic characterization using multiple analytical techniques. Through established in vitro and in vivo infection models, we evaluated the therapeutic efficacy of this nanosystem. Results demonstrated that Tyr-MM@PLGA/G+F actively targets ALI lesion sites, achieving precise co-delivery and synergistic action of geraniol and FK13-a1 at the pathological foci, thereby significantly enhancing treatment outcomes. This study not only validates the remarkable efficacy of this composite nanosystem against ALI but also provides novel insights and experimental evidence for targeted therapy of this condition.

CAS / MDL: 9002-89-5 75-09-2
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COLLOIDS AND SURFACES B-BIOINTERFACES · 2024 · IF 5.4

Covalent modification of γ-cyclodextrin with geraniol: An antibacterial agent with good thermal stability, solubility and biocompatibility

Xiaowei Ding,Xuerong Luo,Imran Mahmood Khan,Lin Yue,Yin Zhang,Zhouping Wang

Geraniol (Ger) is an essential oil molecule with excellent biological activity. High hydrophobicity and volatility limit its practical application. Cyclodextrins (CDs) are water-soluble cyclic oligosaccharides with hydrophobic cavities. Physical encapsulation of CDs to improve the solubility and stability of essential oil molecules is not satisfactory. Therefore, this study synthesized the γ-CD derivative (γ-CD-Ger) by grafting Ger onto γ-CD using a bromide-mediated method. Compared to the inclusion complexes (γ-CD/Ger) formed by both, the derivatives exhibit better solubility and thermal stability. The derivative has better antibacterial activity when the ratio of γ-CD to Ger was 1:2. In addition, the derivatives did not exhibit cytotoxic and hemolytic properties. These results indicate that this research provides a water-soluble antibacterial agent with a wide range of promising applications and offers new ideas for the application of alcohol hydrophobic molecules in aqueous systems.

研究领域: 食品科学 · 药物化学 · 微生物学
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JOURNAL OF CHEMICAL THERMODYNAMICS · 2016 · IF 2.196

Influence of the temperature on the (liquid + liquid) phase equilibria of (water + 1-propanl + linalool or geraniol)

Li Wan,Hengde Li,Cheng Huang,Yuqing Feng,Guoqiang Chu,Yuying Zheng,Wei Tan,Yanlin Qin,Dalei Sun,Yanxiong Fang

Linalool and geraniol are the primary components of rose oil, palmarosa oil, and citronella oil and many other essential oils, and two important compounds used in the flavour and fragrance, cosmetic or pharmaceutical industries. Phase equilibria (LLE, VLE, solubility, etc. ) and related thermodynamic properties of a mixture are essential in the processes design and control of mass transfer process. In this work, experimental (liquid   +   liquid) equilibria data of the systems (water   +   1-propanl   +   linalool) and (water   +   1-propanl   +   geraniol) are presented. The (liquid   +   liquid) equilibria of both systems were determined with a tie-line method at T   =   (283.15, 298.15 and 313.15)   K under atmospheric pressure. The well-known Hand, Bachman and Othmer–Tobias equations were used to test the reliability of the experimental values. The influence of the temperature on the (liquid   +   liquid) phase equilibria of the mixtures, the binodal curves and distribution ratios of 1-propanl are shown and discussed. Moreover, the NRTL and UNIQUAC models were applied to fit the data for both ternary systems. The interaction parameters obtained from both models successfully correlated the equilibrium compositions. Furthermore, the ternary systems could be represented using the binary parameters of the thermodynamic model with a function of temperature.

研究领域: 化学工程 · 热力学
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ACS Synthetic Biology · 2025 · IF 3.9

Peroxisomal Compartmentalization of the Methylerythritol-4-phosphate Pathway Alleviates Cellular Stress and Enhances Geraniol Production in Saccharomyces cerevisiae

Jerome R. Lon,Xuemei Zhao,Gulkiz Mamatrixat,Zhoukang Zhuang,Zhehao Jin,Tao Yu,Jufang Wang,Hongting Tang

Terpenoids are a diverse class of compounds with significant application potential. While prokaryotic bacteria synthesize terpenoids via the methylerythritol-4-phosphate (MEP) pathway, fungi utilize the mevalonate (MVA) pathway. The MVA pathway has been widely employed for efficient terpenoid production in bacteria such as Escherichia coli, but the MEP pathway performs poorly for biosynthesis in yeast. In this study, we constructed a compartmentalized MEP pathway to enhance monoterpenoid production in Saccharomyces cerevisiae. By introducing a geraniol synthase, we initially achieved the production of geraniol from glucose. Further effective incorporation of a cytosolic MEP pathway with nine enzymes increased geraniol production by 174.5%. However, this also significantly inhibited cell growth. Overexpression analysis revealed that flavodoxin and flavodoxin reductase were major contributors to growth inhibition, which could also be a factor limiting the application of the MEP pathway. To address these issues, we employed peroxisomal compartmentalization to isolate the MEP pathway from cytosolic metabolism. This strategy alleviated growth inhibition and improved geraniol production by 93.18% compared to that of cytosolic expression. Through additional metabolic engineering, we optimized peroxisomal geraniol production, achieving a yield of 30.64 mg/L. Our findings demonstrate the potential of compartmentalized MEP pathway expression as a viable approach for enhancing terpenoid biosynthesis in yeast, offering valuable insights for future metabolic engineering efforts.

研究领域: 合成生物学 · 代谢工程 · 微生物生物技术 · 系统生物学 · 生物制造
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JOURNAL OF MOLECULAR HISTOLOGY · 2023 · IF 3.2

Intra-articular delivery of geraniol encapsulated by pH/redox-responsive nanogel ameliorates osteoarthritis by regulating oxidative stress and inflammation

Pan Jun,Cai Youzhi,Zhang Chi,Xu Sanzhong

Osteoarthritis (OA) remains a challenging condition due to limited drug bioavailability within the avascular and dense cartilage matrix. This study introduces a pH/redox-responsive nanogel for enhanced delivery of geraniol in OA therapy. We investigated geraniol's role in preventing chondrocyte matrix degradation and designed a pH/redox-responsive nanogel as a delivery platform. Our methods included Western blot, histological staining, and immunohistochemistry. Geraniol treatment reduced Keap1 expression while elevating Nrf2 and HO-1 levels, effectively inhibiting cartilage matrix degradation. The pH/redox-responsive nanogel further enhanced geraniol’s therapeutic impact. Our study demonstrates that geraniol encapsulated within a pH/redox-responsive nanogel mitigates OA by regulating oxidative stress and inflammation. This innovative approach holds potential as an effective OA therapeutic strategy.

CAS / MDL: 79-10-7 56-85-9 106-24-1
研究领域: 药理学 · 纳米技术 · 骨科 · 风湿病学
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