Identification, Functional Characterization, and Evolution of Terpene Synthases from a Basal Dicot

Yahyaa, Mosaab; Matsuba, Yuki; Brandt, Wolfgang; Doron‐Faigenboim, Adi; Bar, Einat; McClain, Alan M.; Davidovich‐Rikanati, Rachel; Lewinsohn, Efraim; Pichersky, Eran; Ibdah, Mwafaq

doi:10.1104/pp.15.00930

Cited by 29 publications

(40 citation statements)

References 66 publications

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“…The data from this work also show that fresh dried ethanol extracts of Bay leaf (BL) ( Laurus nobilis ) contains anti-inflammatory properties [54, 55]. Previous work by others demonstrates the oil (not aqueous) extracts to contain antimicrobial/food preserving properties due to cineole, eugenol, pinene, eucalyptol, linalool, carvacrol and α-terpinenyl acetate all evidentially toxic to Gram-positive bacteria ( Staphylococcus aureus/pyogenes ) and fungi ( Candida albicans, Aspergillus fumigatus ) [56–59].…”

Section: Discussionmentioning

confidence: 87%

Natural product HTP screening for antibacterial (E.coli 0157:H7) and anti-inflammatory agents in (LPS from E. coli O111:B4) activated macrophages and microglial cells; focus on sepsis

Mazzio

Bauer

et al. 2016

BMC Complement Altern Med

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BackgroundAcute systemic inflammatory response syndrome arising from infection can lead to multiple organ failure and death, with greater susceptibility occurring in immunocompromised individuals. Moreover, sub-acute chronic inflammation is a contributor to the pathology of diverse degenerative diseases (Parkinson’s disease, Alzheimer’s disease and arthritis). Given the known limitations in Western medicine to treat a broad range of inflammatory related illness as well as the emergence of antibiotic resistance, there is a renewed interest in complementary and alternative medicines (CAMs) to achieve these means.MethodsA high throughput (HTP) screening of >1400 commonly sold natural products (bulk herbs, cooking spices, teas, leaves, supplement components, nutraceutical food components, fruit and vegetables, rinds, seeds, polyphenolics etc.) was conducted to elucidate anti-inflammatory substances in lipopolysaccharide (LPS) (E. coli serotype O111:B4) monocytes: RAW 264.7 macrophages [peripheral], BV-2 microglia [brain]) relative to hydrocortisone, dexamethasone and L-N6-(1Iminoethyl)lysine (L-NIL). HTP evaluation was also carried out for lethal kill curves against E.coli 0157:H7 1x106 CFU/mL relative to penicillin. Validation studies were performed to assess cytokine profiling using antibody arrays. Findings were corroborated by independent ELISAs and NO2–/iNOS expression quantified using the Griess Reagent and immunocytochemistry, respectively. For robust screening, we developed an in-vitro efficacy paradigm to ensure anti-inflammatory parameters were observed independent of cytotoxicity. This caution was taken given that many plants exert tumoricidal and anti-inflammatory effects at close range through similar signaling pathways, which could lead to false positives.ResultsThe data show that activated BV-2 microglia cells (+ LPS 1μg/ml) release >10-fold greater IL-6, MIP1/2, RANTES and nitric oxide (NO2–), where RAW 264.7 macrophages (+ LPS 1μg/ml) produced > 10-fold rise in sTNFR2, MCP-1, IL-6, GCSF, RANTES and NO2–. Data validation studies establish hydrocortisone and dexamethasone as suppressing multiple pro-inflammatory processes, where L-NIL suppressed NO2–, but had no effect on iNOS expression or IL-6. The screening results demonstrate relative few valid hits with anti-inflammatory effects at < 250μg/ml for the following: Bay Leaf (Laurus nobilis), Elecampagne Root (Inula helenium), Tansy (Tanacetum vulgare),Yerba (Eriodictyon californicum) and Centipeda (Centipeda minima), Ashwagandha (Withania somnifera), Feverfew (Tanacetum parthenium), Rosemary (Rosmarinus officinalis), Turmeric Root (Curcuma Longa), Osha Root (Ligusticum porteri), Green Tea (Camellia sinensis) and constituents: cardamonin, apigenin, quercetin, biochanin A, eupatorin, (-)-epigallocatechin gallate (EGCG) and butein. Natural products lethal against [E. coli 0157:H7] where the LC50 < 100 μg/ml included bioactive silver hydrosol-Argentyn 23, green tea (its constituents EGCG > Polyphenon 60 > (-)-Gallocatechin > Epicatechin > (+)-Catechin), G...

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Section: Discussionmentioning

confidence: 87%

Natural product HTP screening for antibacterial (E.coli 0157:H7) and anti-inflammatory agents in (LPS from E. coli O111:B4) activated macrophages and microglial cells; focus on sepsis

Mazzio

Bauer

et al. 2016

BMC Complement Altern Med

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“…The selected EOs mostly derived from leaves that had been collected during the May-June season. The GC data of EOs (Table S1) from male trees regarding relative contents in 1,8-cineole plus α-terpinyl acetate differed some way but the size of difference was affected mainly by seasonal changes, possibly because gender-related differences are not expected to be expressed in leaves to the same extent as in other dedicated organs (flowers) [28]. Such a hypothesis needs further examination.…”

Section: Exploratory Analysis Of Spectral Datamentioning

confidence: 98%

Diagnostic Potential of FT-IR Fingerprinting in Botanical Origin Evaluation of Laurus nobilis L. Essential Oil is Supported by GC-FID-MS Data

et al. 2020

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The last years, non-targeted fingerprinting by Fourier-transform infrared (FT-IR) spectroscopy has gained popularity as an alternative to classical gas chromatography (GC)-based methods because it may allow fast, green, non-destructive and cost-effective assessment of quality of essential oils (EOs) from single plant species. As the relevant studies for Laurus nobilis L. (bay laurel) EO are limited, the present one aimed at exploring the diagnostic potential of FT-IR fingerprinting for the identification of its botanical integrity. A reference spectroscopic dataset of 97 bay laurel EOs containing meaningful information about the intra-species variation was developed via principal component analysis (PCA). This dataset was used to train a one-class model via soft independent modelling class analogy (SIMCA). The model was challenged against commercial bay laurel and non-bay laurel EOs of non-traceable production history. Overall, the diagnostic importance of spectral bands at 3060, 1380–1360, 1150 and 1138 cm−1 was assessed using GC-FID-MS data. The findings support the introduction of FT-IR as a green analytical technique in the quality control of these often mislabeled and/or adulterated precious products. Continuous evaluation of the model performance against newly acquired authentic EOs from all producing regions is needed to ensure validity over time.

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“…Three TPS genes encoding monoterpene synthases were isolated in Litsea cubeba: LcTPS1, which converts geranyl diphosphate to trans-ocimene, LcTPS2, which converts geranyl diphosphate to α-thujene, and LcTPS3, a mutifunctional enzyme that converts geranyl diphosphate to α-thujene and (+)sabinene [44]. In Laurus nobilis, the formation of 1,8-cineole, cadinenes and geranyllinalool catalyzed by TPS enzymes was characterized [28]. Sixty-seven unigenes were isolated from the transcriptome of C. camphora, which might be involved in terpene biosynthesis.…”

Section: Discussionmentioning

confidence: 99%

“…Monoterpenes were important components of leaf essential oil in C. porrectum, and the study of monoterpenes biosynthesis was of great significance. Monoterpene synthase was the key enzyme in monoterpene biosynthesis, and now many monoterpene synthases have been isolated from plants [22][23][24][25][26][27][28][29]. Linalool synthase (LIS) gene was isolated from different source of Cinnamomum osmophloeum [26].…”

Section: Introductionmentioning

confidence: 99%

“…Bornyl diphosphate synthase (LaBPPS) was cloned from Lavandula angustifolia [27], which can catalyze the production of Bornyl or camphor. Through bioinformatics analysis, a monoterpene synthetase was identified from Laurus nobilis, and mainly catalyzes the formation of 1,8-cineole [28]. A monoterpene synthetase was cloned from Cinnamomum tenuipilum, which was specifically expressed in the geraniol chemotype.…”

Section: Introductionmentioning

confidence: 99%

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Full-Length Transcriptome Sequencing and Different Chemotype Expression Profile Analysis of Genes Related to Monoterpenoid Biosynthesis in Cinnamomum porrectum

Qiu

Wang

Zheng

et al. 2019

IJMS

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Leaves of C. porrectum are rich in essential oils containing monoterpenes, sesquiterpenes and aromatic compounds, but the molecular mechanism of terpenoid biosynthesis in C. porrectum is still unclear. In this paper, the differences in the contents and compositions of terpenoids among three chemotypes were analyzed using gas chromatography mass spectrometry (GC/MS). Furthermore, the differential expression of gene transcripts in the leaf tissues of the three C. porrectum chemotypes were analyzed through a comparison of full-length transcriptomes and expression profiles. The essential oil of the three C. porrectum chemotypes leaves was mainly composed of monoterpenes. In the full-length transcriptome of C. porrectum, 104,062 transcripts with 306,337,921 total bp, an average length of 2944 bp, and an N50 length of 5449 bp, were obtained and 94025 transcripts were annotated. In the eucalyptol and linalool chemotype, the camphor and eucalyptol chemotype, and the camphor and linalool chemotype comparison groups, 21, 22 and 18 terpene synthase (TPS) unigenes were identified respectively. Three monoterpene synthase genes, CpTPS3, CpTPS5 and CpTPS9, were upregulated in the eucalyptol chemotype compared to the linalool chemotype and camphor chemotype. CpTPS1 was upregulated in the camphor chemotype compared to the linalool chemotype and the eucalyptol chemotype. CpTPS4 was upregulated in the linalool chemotype compared to the camphor chemotype and the eucalyptol chemotype. Different unigenes had different expression levels among the three chemotypes, but the unigene expression levels of the 2-C-methyl-D-erythritol 4phosphate (MEP) pathway were generally higher than those of the mevalonate acid (MVA) pathway. Quantitative reverse transcription PCR(qRT-PCR) further validated these expression levels. The present study provides new clues for the functional exploration of the terpenoid synthesis mechanism and key genes in different chemotypes of C. porrectum.

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Identification, Functional Characterization, and Evolution of Terpene Synthases from a Basal Dicot

Cited by 29 publications

References 66 publications

Natural product HTP screening for antibacterial (E.coli 0157:H7) and anti-inflammatory agents in (LPS from E. coli O111:B4) activated macrophages and microglial cells; focus on sepsis

Natural product HTP screening for antibacterial (E.coli 0157:H7) and anti-inflammatory agents in (LPS from E. coli O111:B4) activated macrophages and microglial cells; focus on sepsis

Diagnostic Potential of FT-IR Fingerprinting in Botanical Origin Evaluation of Laurus nobilis L. Essential Oil is Supported by GC-FID-MS Data

Full-Length Transcriptome Sequencing and Different Chemotype Expression Profile Analysis of Genes Related to Monoterpenoid Biosynthesis in Cinnamomum porrectum

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