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Trichomes are specialized hair-like structures in the epidermal cells of the above-ground parts of plants and help to protect them from pests and pathogens, and produce valuable metabolites. Chrysanthemum morifolium , which is used in tea products, has both ornamental and medicinal value; however, it is susceptible to infection by the fungus Alternaria alternata , which can result in substantial economic losses. Increasing the density of glandular trichomes enhances disease resistance and improves the production of medicinal metabolites in chrysanthemums, and jasmonate (JA) is known to promote the formation of trichomes in various plants. However, it remains unclear whether glandular trichomes in chrysanthemums are regulated by JA. In addition, grafting, a technique that can improve plant resistance to biotic stresses, has been poorly examined for its impact on glandular trichomes, terpenoids, and disease resistance. In this study, we demonstrate that grafting with Artemisia vulgaris rootstocks improves the resistance of chrysanthemum scions to A. alternata. Heterografted chrysanthemums exhibited higher trichome density and terpenoid content compared to self-grafted counterparts. Transcriptome analysis highlighted the significant role of CmJAZ1-like in disease resistance in heterografted chrysanthemums. Lines overexpressing CmJAZ1-like exhibited sensitivity to A. alternata , and this was characterized by reduced glandular trichome density and limited terpenoid content. Conversely, CmJAZ1-like silenced lines exhibited resistance to A. alternata and showed increased glandular trichome density and terpenoid content. Higher JA content was found in the heterografted chrysanthemum scions compared to self-grafted ones. Furthermore, we established that JA promoted the development of glandular trichomes and the synthesis of terpenoids while also inducing the degradation of CmJAZ1-like proteins in chrysanthemums. Our findings suggest that higher JA increases trichome density and terpenoid content, thereby enhancing resistance to A. alternata by regulating CmJAZ1-like in heterografted chrysanthemums. [ABSTRACT FROM AUTHOR]

Background: Amomum tsao-ko is an important aromatic crop used in medicines and food. It can be categorized into three main types based on the fruit shape: long (L), oval (O), and round (R). However, limited information is available on the volatile substances present in differently shaped A. tsao-ko fruits. This study investigated the characteristics and biosynthesis of volatile organic compounds (VOCs) in fresh and dried A. tsao-ko fruits of different shapes using widely targeted volatilomics and transcriptome analyses. Results: In total, 978 VOCs, primarily terpenoids, esters, and heterocyclic compounds, were detected. The number of differentially accumulated volatile organic compounds (DAVOCs) in dried fruits of various shapes was significantly higher than that in fresh fruits, with terpenoids, esters, and heterocyclic compounds accounting for approximately 50% of the total DAVOCs. Notably, α-phellandrene, identified as a shared differential accumulated terpenoid across various fruit shapes, was detected in both fresh and dried fruits. Through transcriptome analysis, 40 candidate genes implicated in the terpenoid biosynthesis pathway were screened. An integrated analysis of the metabolome and transcriptome revealed that the structural genes HMGR-2, TPS7, TPS5-10, TPS21-3, TPS21-5, TPS21-6, TPS21-7, and TPS21-9, along with 81 transcription factors (including 17 NACs, 16 MYBs, 16 AP2/ERFs, 13 WRKYs, 13 bHLHs, and 6 bZIPs), co-regulate the biosynthesis of volatile terpenoids. Conclusions: This study expands our understanding of the volatile metabolism profile of A. tsao-ko and provides a solid foundation for future investigations of the mechanisms governing fruit quality. [ABSTRACT FROM AUTHOR]

Extractives, which naturally evolve as fundamental defense mechanisms in wood against environmental stresses, hold an essential place in the field of wood conservation science. Despite their low content in woody substrates, extractives are chemically complex and can be extracted accurately by solvents with different polarities, covering key components such as aliphatic, terpenoid, and phenolic compounds. The application of solvent extraction allows for the effective recovery of these extracts from forestry waste, thereby creating new opportunities for their reuse in wood modification and enhancing the economic value and potential applications of forestry waste. In the wood industry, extractives not only act as efficient preservatives and photo-stabilizers, significantly improving the decay resistance and photodegradation resistance of wood, but also serve as ideal dyes for fast-growing wood due to their abundant natural colors, which lend the product a distinct aesthetic appeal. The aim of this paper is to provide a comprehensive review of the origin and distribution characteristics of wood extractives and to examine the impact of solvent selection on extraction efficiency. At the same time, the mechanism of extractives in enhancing wood decay resistance and slowing down photodegradation is deeply analyzed. In addition, specific examples are presented to illustrate their wide utilization in the wood industry. This is intended to provide references for research and practice in related fields. [ABSTRACT FROM AUTHOR]

Background: Phalaenopsis bellina, an orchid native to Borneo, is renowned for its unique appearance. It releases distinct fragrances, which have been linked to the presence of terpenoids. However, the identification and study of sesquiterpene synthase in P. bellina remain limited. In this study, we examines the functional characterisation of terpene synthase (TPS) from P. bellina, known as PbTS, through recombinant protein expression and its manifestation in the flower. Methods and Results: Gene annotation of PbTS revealed that the inferred peptide sequence of PbTS comprises 1,680 bp nucleotides encoding 559 amino acids with an estimated molecular mass of 65.2 kDa and a pI value of 5.4. A similarity search against GenBank showed that PbTS shares similarities with the previously published partial sequence of P. bellina (ABW98504.1) and Phalaenopsis equestris (XP_020597359.1 and ABW98503.1). Intriguingly, the phylogenetic analysis places the PbTS gene within the TPS-a group. In silico analysis of PbTS demonstrated stable interactions with farnesyl pyrophosphate (FPP), geranyl pyrophosphate (GPP), and geranylgeranyl pyrophosphate (GGPP). To verify this activity, an in vitro enzyme assay was performed on the PbTS recombinant protein, which successfully converted FPP, GPP, and GGPP into acyclic sesquiterpene β-farnesene, yielding approximately 0.03 mg/L. Expressional analysis revealed that the PbTS transcript was highly expressed in P. bellina, but its level did not correlate with β-farnesene levels across various flowering time points and stages. Conclusion: The insights gained from this study will enhance the understanding of terpenoid production in P. bellina and aid in the discovery of novel fragrance-related genes in other orchid species. [ABSTRACT FROM AUTHOR]

Basil (Ocimum basilicum L.) is a widely used culinary herb. In this study, ethanol, dichloromethane, and sunflower oil were used separately as solvents with distinct polarities for the extraction of basil aerial parts to simulate the different polarity conditions in domestic food processing. The oil extract (OE) was re-extracted with acetonitrile, and the chemical composition, antioxidant potential, and antimicrobial activities of the ethanol (EE), dichloromethane (DCME), and acetonitrile (ACNE) extracts were determined. A total of 109 compounds were tentatively identified in EE, DCME, and ACNE by HPLC–DAD/ESI-ToF-MS. Fatty acids were present in all extracts. Phenolic acids and flavonoids dominated in EE. DCME was characterised by triterpenoid acids, while diterpenoids were mainly found in ACNE. The extracts were analysed for their antioxidant capacity using the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) assay. EE and DCME showed significant radical scavenging potential. Antimicrobial activity was explored in eight bacterial, two yeast, and one fungal species. All extracts exhibited high antifungal activity, comparable to or better than that of the commercial drug nistatin. Antibacterial activities were notable for EE and ACNE, while DCME showed no activity against bacteria in the applied concentration ranges. The different polarities of the solvents led to distinctive phytochemical compositions and bioactivities in the extracts. [ABSTRACT FROM AUTHOR]

Abstract Background Amomum tsao-ko is an important aromatic crop used in medicines and food. It can be categorized into three main types based on the fruit shape: long (L), oval (O), and round (R). However, limited information is available on the volatile substances present in differently shaped A. tsao-ko fruits. This study investigated the characteristics and biosynthesis of volatile organic compounds (VOCs) in fresh and dried A. tsao-ko fruits of different shapes using widely targeted volatilomics and transcriptome analyses. Results In total, 978 VOCs, primarily terpenoids, esters, and heterocyclic compounds, were detected. The number of differentially accumulated volatile organic compounds (DAVOCs) in dried fruits of various shapes was significantly higher than that in fresh fruits, with terpenoids, esters, and heterocyclic compounds accounting for approximately 50% of the total DAVOCs. Notably, α-phellandrene, identified as a shared differential accumulated terpenoid across various fruit shapes, was detected in both fresh and dried fruits. Through transcriptome analysis, 40 candidate genes implicated in the terpenoid biosynthesis pathway were screened. An integrated analysis of the metabolome and transcriptome revealed that the structural genes HMGR-2, TPS7, TPS5-10, TPS21-3, TPS21-5, TPS21-6, TPS21-7, and TPS21-9, along with 81 transcription factors (including 17 NACs, 16 MYBs, 16 AP2/ERFs, 13 WRKYs, 13 bHLHs, and 6 bZIPs), co-regulate the biosynthesis of volatile terpenoids. Conclusions This study expands our understanding of the volatile metabolism profile of A. tsao-ko and provides a solid foundation for future investigations of the mechanisms governing fruit quality.

Background: Despite the availability of chemotherapy drugs such as 5-fluorouracil (5-FU), the treatment of some cancers such as gastric cancer remains challenging due to drug resistance and side effects. This study aimed to investigate the effect of celastrol in combination with the chemotherapy drug 5-FU on proliferation and induction of apoptosis in human gastric cancer cell lines (AGS and EPG85-257). Materials and Methods: In this in vitro study, AGS and EPG85-257 cells were treated with different concentrations of celastrol, 5-FU, and their combination. Cell proliferation was assessed using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. The synergistic effect of 5-FU and celastrol was studied using Compusyn software. The DNA content at different phases of the cell cycle and apoptosis rate was measured using flow cytometry. Results: Co-treatment with low concentrations (10% inhibitory concentration (IC10)) of celastrol and 5-FU significantly reduced IC50 (p < 0.05) so that 48 h after treatment, IC50 was calculated at 3.77 and 6.9 μM for celastrol, 20.7 and 11.6 μM for 5-FU, and 5.03 and 4.57 μM for their combination for AGS and EPG85-257 cells, respectively. The mean percentage of apoptosis for AGS cells treated with celastrol, 5-FU, and their combination was obtained 23.9, 41.2, and 61.9, and for EPG85-257 cells 5.65, 46.9, and 55.7, respectively. In addition, the 5-FU and celastrol-5-FU combination induced cell cycle arrest in the synthesis phase. Conclusions: Although celastrol could decrease the concentration of 5-fluorouracil that sufficed to suppress gastric cancer cells, additional studies are required to arrive at conclusive evidence on the anticancer effects of celastrol. [ABSTRACT FROM AUTHOR]

Context: Interleukin-17 (IL-17) is a pro-inflammatory cytokine that plays a crucial role in immunity and inflammation. Aims: To evaluate the potential therapeutic effects of two compounds, magnosalicine and neotatarine, derived from the ethanolic extract of Acorus calamus L. rhizome, against IL-17. Methods: Utilizing LC/MS analysis combining molecular docking simulations, drug likeness, ADME and toxicity analysis. This study explored the molecular interactions and binding affinities of identified compounds from A. calamus with crucial residues of IL-17, including Tyr62, Pro63, Ile66, Gln94, Ile96, Leu97, and Leu99. Results: The results revealed that magnosalicine and neotatarine exhibited remarkable binding affinities of -10.16 kcal/mol and -9.53 kcal/mol, respectively, indicating their strong interactions with IL-17. Moreover, both compounds displayed superior binding energies compared to other extract constituents. Interestingly, this study highlighted that all terpenoid compounds from the A. calamus rhizome extract were capable of interacting with these key residues of IL-17, resembling the interactions observed with the natural ligand (RMK) and methotrexate. Meanwhile, the analysis results revealed a safer ADME and toxicity profile for neotatarine compared to magnolalicine. Conclusions: This research unveils the promising potential of neotatarine as candidates for further exploration in therapeutic interventions targeting IL-17-related pathways. These findings shed light on the molecular insights of Acorus calamus L. compounds, providing valuable information for developing novel treatments for IL-17-associated disorders.

Lycopene is a compound classified as carotenoid, also known as tetraterpenoids, and its high antioxidative capabilities make demand in pharmaceutical and nutrient fields. For these reasons, much research on microbial production of lycopene has been developed and reported for more than two decades. Nevertheless, a standardized in vitro biosynthesis method for lycopene synthesis has not been reported to date. The major reasons of the absence of this method lie on the poor solubility of hydrophobic intermediates (geranylgeranyl pyrophosphate [GGPP] and phytoene), and the difficulty of employing membrane-binding enzyme, phytoene desaturase (CrtI) into in vitro reactions. In this study, we developed a standard method of in vitro biosynthesis of lycopene from geranyl pyrophosphate using four enzymes, namely farnesyl pyrophosphate synthase (IspA), GGPP synthase (CrtE), phytoene synthase (CrtB), phytoene desaturase (CrtI), and liposome-the key material, which can provide both hydrophobic area and a lipid membrane for the membrane-binding enzyme CrtI. Moreover, we performed a screening of the in vitro lycopene synthetic pathway using cell-free protein synthesis system, which verifies the applicability of our system as a tool for screening the lycopene synthesis pathway. [ABSTRACT FROM AUTHOR]

Introduction: Croton crassifolius Geisel. (CCG) is a traditional Chinese medicine widely used in South China. It has various pharmacological effects and is often used in treating rheumatoid arthritis and gastric and duodenal ulcers. However, the chemical characteristics and its effective constituents are still scarcely studied. Objective: To determine the phytochemical profile of the CCG extract and to investigate the chemical characteristics of terpenoids extracted from rat plasma following oral administration of CCG extract based on UPLC‐Q/TOF‐MS. Moreover, six terpenoids in CCG were quantified, and in vivo pharmacokinetic behavior after oral CCG extract was further explored. Results: In total, 56 terpenoids were tentatively identified in the CCG extract and 16 terpenoids were detected in rat plasma after oral CCG extract. In addition, the contents of six terpenoids in CCG were clarified. The plasma quantification method of six terpenoids was further established, validated, and confirmed to have good sensitivity and specificity. The six analytes exhibited excellent linearity in respective concentration ranges (r ≥ 0.998). The intra‐day and inter‐day precisions relative standard deviation (RSD, %) were less than 11.27%, and the accuracies ranged from −7.06% to 9.91%. Stability, extraction recovery, and matrix effect in plasma were within the required limits (RSD < 15%). Conclusion: A total of 56 terpenoids were identified in CCG and 16 prototype components in plasma after oral CCG. The validated quantitative method was successfully applied to the simultaneous determination of six major terpenoids in plasma. The pharmacokinetic parameters are clarified, which can guide the clinical application of CCG. A total of 56 compounds in Croton crassifolius Geisel. (CCG) and 16 prototype components in plasma after oral CCG extract were identified by UPLC‐Q/TOF‐MS. In addition, the contents of six terpenoids in CCG were determined. The UPLC Q/TOF‐MS method was further developed and successfully applied to elucidate the pharmacokinetic characteristics of the six components in plasma after oral CCG extract. According to that, it can better guide the clinical application of CCG. [ABSTRACT FROM AUTHOR]

Introduction: Camphora longepaniculata, a crucial commercial crop and a fundamental component of traditional Chinese medicine, is renowned for its abundant production of volatile terpenoids. However, the lack of available genomic information has hindered pertinent research efforts in the past. Methods: To bridge this gap, the present study aimed to use PacBio HiFi, short-read, and high-throughput chromosome conformation capture sequencing to construct a chromosome-level assembly of the C. longepaniculata genome. Results and discussion: With twelve chromosomes accounting for 99.82% (766.69 Mb) of the final genome assembly, which covered 768.10 Mb, it was very complete. Remarkably, the assembly’s contig and scaffold N50 values are exceptional as well—41.12 and 63.78 Mb, respectively—highlighting its excellent quality and intact structure. Furthermore, a total of 39,173 protein-coding genes were predicted, with 38,766 (98.96%) of them being functionally annotated. The completeness of the genome was confirmed by the Benchmarking Universal Single-Copy Ortholog evaluation, which revealed 99.01% of highly conserved plant genes. As the first comprehensive assembly of the C. longepaniculata genome, it provides a crucial starting point for deciphering the complex pathways involved in terpenoid production. Furthermore, this excellent genome serves as a vital resource for upcoming research on the breeding and genetics of C. longepaniculata. [ABSTRACT FROM AUTHOR]

In plants, secondary metabolites change in response to environmental conditions. These changes co-regulate resilience to stressful environmental conditions, plant growth and development, and interactions between plants and the wider ecosystem, while also affecting soil carbon storage and atmospheric and climatic conditions. The objective of this study was to determine the association between UV exposure and the contents of key metabolites, including amino acids, phenolics, flavonoids, terpenoids, carotenoids, tocopherols, and phytosterols. Mentha spicata plantlets were grown in tissue culture boxes for 30 days and then exposed to a low dose of broadband UV-B (291–315 nm; 2.8 kJm−2 biologically effective UV) enriched light for eight days. Metabolite contents were quantified either immediately after the final UV exposure, or after seven days of recovery under photosynthetically active radiation. It was found that UV promoted the production of flavonoids (1.8-fold) ahead of phenolic acids (unchanged). Furthermore, the majority of monoterpenes and sesquiterpenes, constituents of valuable mint essential oil, were significantly increased through UV treatment (up to 90-fold for α-linalool). In contrast, the contents of carotenoids and tocopherols did not increase following UV exposure. A comparison between plants sampled immediately after UV exposure and after seven days of recovery showed that there was an overall increase in the content of carotenoids, mono- and sesquiterpenes, phenolics, and amino acids following recovery, while the contents of sterols and tocopherols decreased. These UV-induced changes in metabolite profile may have important consequences for agriculture, ecology, and even the global climate, and they also provide an exciting opportunity to enhance crop value, facilitating the development of improved products with higher levels of essential oils and added benefits of enhanced flavour, colour, and bioactive content. [ABSTRACT FROM AUTHOR]

Hemerocallis citrina is an edible and medicinal homologous plant, which is rich in many nutrients and bioactive components. Terpenoids are a kind of important bioactive component in H. citrina. To understand the dominant terpenoid metabolites in H. citrina roots, stems, leaves, and flowers, respectively, this study analyzed the terpenoid metabolites in these 4 organs based on the ultra performance liquid chromatography-tandem mass spectrometry technology of widely targeted metabolomics. A total of 43 terpenoids were identified, including 7 kinds of monoterpenoids (16.2%), 18 kinds of ditepenoids (41.9%), 16 kinds of triterpene (37.2% ), and 2 kinds of triterpene saponin (4.7%). Principal component analysis and clustering analysis indicated that the mass spectrometry data were reliable, and the accumulation of terpenoids in different organs was significantly different. The dominant terpenoid metabolites in roots included isopimaradieneone, pimaradienone, abietic acid, scutebarbolide C, and isopimaric acid. The dominant terpenoid metabolites in stems included 3, 9-dihydroxy-13(14)-labden-16,15-olide and 9,19-cyclolanost-24-en-3-ol (cycloartenol). The dominant terpenoid metabolites in leaves included viteagnusin A and ent-3β-acetoxyisopimar-15-8β-ol. The dominant terpenoid metabolites in flowers included vitexilactone and 7-Ocoumaroyl- loganic acid. This study listed the relative contents of all terpenoids in roots, stems, leaves, and flowers of H. citrina in detail, which provided the foundation for further investigation of the different usages of various plant organs of H. citrina, and the information is important for the food industry and medical treatment. [ABSTRACT FROM AUTHOR]

• Increasing the potential of Adenostemma lavenia through some types of fertilizer. • Fertilizer application resulted in better growth of A. lavenia compared to control. • The secondary metabolite production is increased when fertilizer is added. • The PCA patterns in A. lavenia extract are clustered based on fertilizer types. • The combination of fertilizers leads to improved growth and chemical compounds. Adenostemma lavenia , a member of the Asteraceae family, possesses numerous medicinal properties, although it is not extensively cultivated. The objective of this research initiative is to determine the optimal fertilizer dosages that result in the optimal productivity of 11α-OH KA, a diterpenoid, phenolic, flavonoid, and terpenoid compounds, as well as growth, in A. lavenia. A one-factor randomized block design was employed with five fertilizer doses: without fertilizer (control), cow manure (20 tons ha−1) (F1), NPK (urea, SP-36, and KCl: 135, 100, 135 kg ha−1, respectively) (F2), the first combination consisting of cow manure (10 tons ha−1) + NPK (urea, SP-36, and KCl: 67.5, 50, 67.5 kg ha−1, respectively) (F3), and the second combination consisting of cow manure (20 tons ha−1) + NPK (urea, SP-36, and KCl: 135, 100, 135 kg ha−1, respectively) (F4). The application of fertilizers stimulates plant development. LC-MS/MS analysis of the methanol extract of A. lavenia revealed the presence of the following compounds: 2 additional compounds, 7 terpenoids, 3 alkaloids, 3 phenolics, 2 fatty acids, 1 flavonoid, and 1 steroid. Combining F2, F3, and F4 makes it possible to produce plants with the highest leaf number, number of branches, and height. The combination of F4 generated the highest phenolic and flavonoid yields (409.88 μmol Gallic Acid Equivalent/plant) and 69.71 μmol Quercetin Equivalent/plant. These yields were not significantly different from those obtained when F2 and F3 were applied. Additionally, F4 produced the highest terpenoids and 11α-OH KA yields (61.48 mmol Nerol Equivalent/plant) and 29.81 mM 11α-OH KA/plant. The medical potential of A. lavenia can be enhanced by applying a mixture consisting of NPK (urea, SP-36, and KCl in a ratio of 135 kg ha−1, respectively) and cow manure (20 tons ha−1). [ABSTRACT FROM AUTHOR]

Numerous herbal products have been the subject of research regarding their potential role in cancer prevention or adjuvant therapy. Pistacia atlantica and its main phytochemicals have garnered significant attention for their potential anti-cancer effects. The study aimed to assess the growth inhibitory effects of P. atlantica essential oil (PAEO) on MKN-45 and AGS cells. This study quantified the volatile compounds in PAEO using Gas Chromatography–Mass Spectrometry (GC–MS). Subsequently, MKN-45 and AGS cells were treated with varying concentrations of PAEO (5%, 2.5%, 1.25%, 0.625%, 0.3125%, 0.156%, 0.0781%, 0.0391%, 0.0195%) for 24 h. Cell viability was evaluated through the MTT assay. The impact of PAEO on gene expression was investigated by quantifying the mRNA levels of Bax and Bcl2 in the various experimental groups using quantitative Real-Time PCR (qRT-PCR) analysis. Additionally, flow cytometry was utilized to evaluate apoptosis in the treated cells. The analysis of PAEO revealed that α-pinene was the predominant monoterpene, constituting 87.9% of the oil composition. The cytotoxic effects of PAEO were evaluated, and it was found that the oil significantly reduced the viability of MKN-45 and AGS cells. The IC50 for MKN-45 cells was determined to be 1.94 × 10–3% after 24 h of treatment, while for AGS cells the IC50 was 2.8 × 10–3% after 24 h. Additionally, the research revealed that PAEO triggered a notable rise in apoptotic cells in both AGS and MKN-45 cell lines. Moreover, at the molecular level, the findings indicated an increase in Bax expression and a decrease in Bcl2 mRNA expression, providing further evidence of the induction of apoptosis in both MKN-45 and AGS cell lines following PAEO treatment. The findings of this study offer evidence supporting the cytotoxic effects of PAEO on gastric cancer cell lines by promoting apoptosis. The findings suggest that PAEO may offer potential as a therapeutic candidate in managing and treating gastric cancer. [ABSTRACT FROM AUTHOR]

Following COVID-19 pandemic, functional foods and beverages continue to develop, especially those with high antioxidant activity. The functional beverage from corn silk can be processed into brewed tea. The critical points in the making process of corn silk tea are the drying equipment, drying temperature, and drying time. With efficient method, corn silk tea can produce high antioxidant activity. The present work optimised the temperature and drying method based on antioxidant activity. The results of the present work are expected to be used in micro/small/medium enterprises (MSMEs) to produce corn silk herbal tea. The present work used Randomised Block Design (RBD) with two factors; drying temperatures (45, 55, and 65°C) and drying equipment (cabinet and oven) for 5 h. The analysis carried out was antioxidant activity and profiling using LC-HRMS (liquid chromatography high-resolution mass spectrometry) that ran in a positive (+) mode. The processing of corn silk tea using cabinet drying at 65°C for 5 h produced antioxidant activity of 82.00 ± 0.75%. This was higher than commercial black tea (81.71 ± 0.15%) and commercial green tea (78.37 ± 0.43%). The analysis using LC-HRMS showed that the corn silk tea contained betaine (N,N,N-trimethylglycine) (RT 0.928), 6-methylquinoline (RT 4.741), hesperidin (3’,5,7-trihydroxy-4’-methoxyflavanone) (RT 302.07817), luvangetin (10-methoxy-2,2-dimethylpyrano[3,2-g]chromen-8-one) (RT 258.08837), embelin (2,5-dihydroxy-3-undecyl-1,4-benzoquinone) (RT 13.074), and eucalyptol (1,8- cineole) (RT 13.325). [ABSTRACT FROM AUTHOR]

Terpenoids are one of the largest class of natural products with diverse structures and activities. This enormous diversity is embedded in enzymes called terpene synthases (TSs), which generate diverse terpene skeletons via sophisticated cyclization cascades. In addition to the many highly selective TSs, there are many promiscuous TSs that accept multiple prenyl substrates, or even noncanonical ones, with 6, 7, 8, 11, and 16 carbon atoms, synthesized via chemical approaches, C-methyltransferases, or engineered lepidopteran mevalonate pathways. The substrate promiscuity of TSs not only expands the structural diversity of terpenes but also highlights their potential for the discovery of novel terpenoids via combinatorial biosynthesis. In this review, we focus on the current knowledge on multisubstrate terpene synthases (MSTSs) and highlight their potential applications.

As an important spice species in Rutaceae, the Sichuan pepper (Zanthoxylum armatum) can provide pungent and numbing taste, as well as aroma in its mature fruit. Here we assembled a chromosome-level genome of green prickly ash which was widely cultivated in a major production area including Chongqing and Sichuan province, China. We generated 712 Gb (∼112 × ) PacBio long reads and 511 Gb (∼82 × ) Hi-C data, and yielded an assembly of 99 pseudochromosomes with total size of 5.32 Gb and contig N50 of 796 kb. The genomic analyses and cytogenetic experiments both indicated that the cultivar ‘Zhuye Huajiao’ was a triploid. We identified a Zanthoxylum-specific whole genome duplication event emerging about 24.8 million years ago (Mya). We also detected a transposition burst event (0.3–0.4 Mya) responsible for the large genome size of Z. armatum. Metabolomic analysis of the Zanthoxylum fruits during development stages revealed profiles of 39 volatile aroma compounds and 528 secondary metabolites, from which six types of sanshools were identified. Based on metabolomic and transcriptomic network analysis, we screened candidate genes encoding long chain acyl-CoA synthetase, fatty acid desaturase, branched-chain amino acid aminotransferase involved in sanshool biosynthesis and three genes encoding terpene synthase during fruit development. The multi-omics data provide insights into the evolution of Zanthoxylum and molecular basis of numbing and aroma flavor of Sichuan pepper.

The study investigated the impact of intraspecific plant chemodiversity on plant growth and reproductive traits at both the plant and plot levels. It also aimed to understand how chemodiversity at stand level affects ecosystem functioning and plant–plant interactions. We describe a biodiversity experiment in which we manipulated intraspecific plant chemodiversity at the plot level using six different chemotypes of common tansy (Tanacetum vulgare L., Asteraceae). We tested the effects of chemotype identity and plot‐level chemotype richness on plant growth and reproductive traits and plot‐level headspace emissions. The study found that plant chemotypes differed in growth and reproductive traits and that traits were affected by the chemotype richness of the plots. Although morphological differences among chemotypes became less pronounced over time, reproductive phenology patterns persisted. Plot‐level trait means were also affected by the presence or absence of certain chemotypes in a plot, and the direction of the effect depended on the specific chemotype. However, chemotype richness did not lead to overyielding effects. Lastly, chemotype blends released from plant communities were neither richer nor more diverse with increasing plot‐level chemotype richness, but became more dissimilar as they became more dissimilar in their leaf terpenoid profiles. We found that intraspecific plant chemodiversity is crucial in plant–plant interactions. We also found that the effects of chemodiversity on plant growth and reproductive traits were complex and varied depending on the chemotype richness of the plots. This long‐term field experiment will allow further investigation into plant–insect interactions and insect community assembly in response to intraspecific chemodiversity. [ABSTRACT FROM AUTHOR]

Protein modeling, carbocation docking, and molecular dynamics along with structure-based mutability landscapes provided insight into taxadiene synthase catalysis (first step of the anticancer Taxol biosynthesis), protein structure-function correlations, and promiscuity. Plant terpenes belong to one of the largest and most diverse classes of natural products. This diversity is driven by the terpene synthase enzyme family which comprises numerous different synthases, several of which are promiscuous. Taxadiene synthase (TXS) is a class I diterpene synthase that catalyzes the first step in the biosynthesis pathway of the diterpene Taxol, an anticancer natural product produced by the Taxus plant. Exploring the molecular basis of TXS catalysis and its promiscuous potential garnered interest as a necessary means for understanding enzyme evolution and engineering possibilities to improve Taxol biosynthesis. A catalytically active closed conformation TXS model was designed using the artificial intelligence system, AlphaFold, accompanied by docking and molecular dynamics simulations. In addition, a mutability landscape of TXS including 14 residues was created to probe for structure-function relations. The mutability landscape revealed no mutants with improved catalytic activity compared to wild-type TXS. However, mutations of residues V584, Q609, V610, and Y688 showed high degree of promiscuity producing cembranoid-type and/or verticillene-type major products instead of taxanes. Mechanistic insights into V610F, V584M, Q609A, and Y688C mutants compared to the wild type revealed the trigger(s) for product profile change. Several mutants spanning residues V584, Q609, Y688, Y762, Q770, and F834 increased production of taxa-4(20),11(12)-diene which is a more favorable substrate for Taxol production compared to taxa-4(5),11(12)-diene. Finally, molecular dynamics simulations of the TXS reaction cascade revealed residues involved in ionization, carbocation stabilization, and cyclization ushering deeper understanding of the enzyme catalysis mechanism. [ABSTRACT FROM AUTHOR]

Seaweeds are a treasure trove of natural secondary metabolites. Terpenoids extracted from seaweeds are shown to possess a variety of antitumor cellular activities. However, due to the complex and diverse structures of terpenoids, their therapeutic targets and complex mechanisms of action have not been clarified. The present study summarises the research on terpenoids from seaweeds in oncological diseases over the last 20 years. Terpenoids show different degrees of inhibitory effects on different types of tumor cells, suggesting that terpenoids in seaweeds may have potential antitumor disease potential. Terpenoids with potential antitumor activity and their mechanism of action are investigated using network pharmacology. A total of 125 terpenoids and 286 targets are obtained. Proto‐oncogene tyrosine‐protein kinase Src(SRC), Signal transducer and activator of transcription 3 (STAT3), Mitogen‐activated protein kinase (MAPK3, MAPK1), Heat shock protein HSP 90‐alpha (HSP90AA1), Phosphatidylinositol‐4,5‐bisphosphate 3‐kinase catalytic subunit alpha (PIK3CA), and RAC‐alpha serine/threonine‐protein kinase (AKT1) are defined as core targets. According to GO function and Kyoto encyclopedia of genes and genomes(KEGG) enrichment analysis, terpenoids may affect the Phoshatidylinositol 3'‐kinase (PI3K)‐Akt signaling pathway, Epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor resistance, Prostate cancer, MAPK signaling pathway, and Proteoglycans in cancer. In addition, the molecular docking results show that the selected terpenoids are all able to bind strongly to the active protein. Terpenoids may slow down the progression of cancer by controlling apoptosis, proliferation, and protein and enzyme binding. [ABSTRACT FROM AUTHOR]

The aim of this research was to explore the chemical composition and antioxidant activities of etheric extracts of Abies marocana. A Soxhlet apparatus was used to extract bioactive molecules from the various parts of the plant. Furthermore, the levels of antioxidant compounds were quantified, while the Gas chromatography was utilized to determine the chemical constituents of the extracted molecules. The extracts were evaluated for their antioxidant properties using the DPPH radical scavenging method and the total antioxidant capacity test. The levels of polyphenols varied across different parts of the plant, ranging from 2.474 ± 0.029 mg.g-1 DM in needles to 4.207 ± 0.008 mg.g-1 DM in twigs. Flavonoids were most abundant in needles 0.140 ± 0.001 mg.g-1 DM and least abundant in cones 0.069 ± 0.007 mg.g-1 DM. Tannins had the highest concentration in twigs 2.608 ± 0.114 mg.g-1 DM, followed by cones 1.948 ± 0.037 mg.g-1 DM and needles 1.512 ± 0.09 mg.g-1 DM. A chromatographic analysis revealed that 56 components were in the samples, with terpene compounds being the most abundant in the different organs. In terms of antioxidant activity, the extract derived from twigs exhibited the strongest antioxidant capacity 49.377 ± 0.371 mg EAA.g-1 DM, followed by cones 35.129 ± 0.084 mg EAA.g-1 DM and needles 13.663 ± 0.084 mg EAA.g-1 DM. Alternatively, the IC50 values for the three organs were found to be in the range of 3844 to 5047.67 µg.mL-1. The results highlight the potential phytopharmaceutical value of A. marocana due to the presence of diverse phyto-components. [ABSTRACT FROM AUTHOR]

Ferula L. plants are of great importance in a number of fields such as agriculture, veterinary, medicine and food industry. Medicinal properties of Ferula L. species are explained by the variety of secondary metabolites they produce, in which the activity of root rhizobacteria occupies a special place. This article presents the research-based analysis of some biological properties, agrotechnology, secondary metabolites (ferulin A,D; diversolid A,D,F,G; kuhistanicaol A,B,C,D,G; kuhistanol (A-H); fucanefuromarin (A-G); fucanemarin A,B; fesumtuorin (A-H); ferulagol A,B; pallidon (A-F); sinkiangenorin D and others) of the species of genus Ferula L., the influence of the microbial communities (new species belonging to the genera Porphyrobacter, Paracoccus and Amycolatopsis, as well as Actinobacteria, Acidobacteria, Proteobacteria, Gemmatimonadet and Bacteroides) living in the roots of Ferula L. on the synthesis of some secondary metabolites of the plant, based on scientific sources.

Abstract Plant secondary metabolites can protect organisms against oxidative stress caused by adverse environmental conditions. Cinnamomum camphora (L.) J. Presl contains plentiful terpenoids and is subdivided into 5 chemotypes. To develop natural antioxidants using the plant terpenoids, the terpenoid composition and antioxidant abilities of methanol, ethyl acetate, n-hexane and petroleum ether extracts from linalool and eucalyptol chemotypes were investigated, and the solvent effects on in vitro antioxidant activity of 8 main terpenoids were analyzed. Meanwhile, the in vivo effects of two strong antioxidant terpenoids were evaluated. For the two chemotypes, the 4 solvents exhibited the same extracting effects on the terpenoid types, but methanol extracts contained the highest content of terpenoids, which should contribute to their strongest scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) free radicals. In linalool and eucalyptol chemotype extracts, linalool, eucalyptol, ocimene, α-pinene, D-limonene, terpinene, β-pinene and longifolene were the 8 main terpenoids. Among the 4 solvents, the 8 terpenoids showed the strongest free radical-scavenging activity with methanol as the reaction medium, which might result from strong-polarity methanol easily activating C = C unsaturated bonds in these compounds. This might also contribute to the strongest scavenging activity of methanol extracts against free radicals. Among these main components, ocimene and longifolene separately showed the strongest activity in scavenging DPPH and ABTS free radical. In in vivo assay, the two compounds significantly lowered the reactive oxygen species (ROS) levels in Chlamydomonas reinhardtii, a single-celled model organism, under H2O2 stress, and the lowering effects gradually enhanced with increasing the compound concentration, resulting in the corresponding promoting effect on the algal growth. At the same concentration, longifolene showed the strongest effect on protecting the algal cells against oxidative stress. Therefore, methanol was suitable for extracting terpenoids in natural antioxidant development, and ocimene and longifolene were two strong antioxidant terpenoids without cell toxicity, with the latter having stronger in vivo antioxidant activity. Graphical Abstract

Abstract Background Cannabis sativa, a dioecious plant that has been cultivated worldwide for thousands of years, is known for its secondary metabolites, especially cannabinoids, which possess several medicinal effects. In this study, we investigated the autopolyploidization effects on the biosynthesis and accumulation of these metabolites, transcriptomic and metabolomic analyses were performed to explore the gene expression and metabolic variations in industrial hemp autotetraploids and their diploid progenitors. Results Through these analyses, we obtained 1,663 differentially expressed metabolites and 1,103 differentially expressed genes. Integrative analysis revealed that phenylpropanoid and terpenoid biosynthesis were regulated by polyploidization. No substantial differences were found in the cannabidiol or tetrahydrocannabinol content between tetraploids and diploids. Following polyploidization, some transcription factors, including nine bHLH and eight MYB transcription factors, affected the metabolic biosynthesis as regulators. Additionally, several pivotal catalytic genes, such as flavonol synthase/flavanone 3-hydroxylase, related to the phenylpropanoid metabolic pathway, were identified as being modulated by polyploidization. Conclusions This study enhances the overall understanding of the impact of autopolyploidization in C. sativa and the findings may encourage the application of polyploid breeding for increasing the content of important secondary metabolites in industrial hemp.

Basil (Ocimum basilicum L.) is a widely used culinary herb. In this study, ethanol, dichloromethane, and sunflower oil were used separately as solvents with distinct polarities for the extraction of basil aerial parts to simulate the different polarity conditions in domestic food processing. The oil extract (OE) was re-extracted with acetonitrile, and the chemical composition, antioxidant potential, and antimicrobial activities of the ethanol (EE), dichloromethane (DCME), and acetonitrile (ACNE) extracts were determined. A total of 109 compounds were tentatively identified in EE, DCME, and ACNE by HPLC–DAD/ESI-ToF-MS. Fatty acids were present in all extracts. Phenolic acids and flavonoids dominated in EE. DCME was characterised by triterpenoid acids, while diterpenoids were mainly found in ACNE. The extracts were analysed for their antioxidant capacity using the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) assay. EE and DCME showed significant radical scavenging potential. Antimicrobial activity was explored in eight bacterial, two yeast, and one fungal species. All extracts exhibited high antifungal activity, comparable to or better than that of the commercial drug nistatin. Antibacterial activities were notable for EE and ACNE, while DCME showed no activity against bacteria in the applied concentration ranges. The different polarities of the solvents led to distinctive phytochemical compositions and bioactivities in the extracts.

A 1,2:3,4:9,10:9,19-tetraseco-cycloartane triterpene spiroketal lactone, pseudoamaolide P (1), two new labdane-type diterpenoids, pseudoamains A and B (2-3), and four known cembrane-type diterpenoids (4–7) were isolated from the seeds of Pseudolarix amabilis. The structures of these compounds were elucidated by spectroscopic analyses, including HRESIMS, 1D-, and 2D-NMR. The anti-inflammatory activities of the compounds were evaluated by suppressing the transcription of the NF-κB-dependent reporter gene in LPS-induced 293 T/NF-κB-luc cells. All compounds do not show potent activity. [ABSTRACT FROM AUTHOR]

Adenostemma madurense is one of the Asteraceae with many medical properties but has not been widely cultivated. This study aims to determine the different fertilizer doses that can produce the best growth, phenolic, flavonoid, terpenoid, and the 11α-OH KA (a diterpenoid found in A. madurense productivity), resulting in the high antioxidant capacity of A. madurense. A one-factor randomized block design was employed in five fertilizer doses, control/without fertilizer, 100 % cow manure (20 tons/ha), 100 % NPK (in the form of urea, SP-36, and KCl:135, 100, 135 kg/ha, respectively), a combination of 50 % cow manure + 50 % NPK, and a combination of 100 % cow manure + 100 % NPK. Fertilizers increase plant growth. Applying the combination of 100 % cow manure + 100 % NPK was the best fertilizer composition, which produced the highest plant height, leaf, and branch number. This fertilizer combination produced total phenolic, flavonoid productivity of 739.50 μmol Gallic Acid Equivalent/plant, 97.37 μmol Quercetin Equivalent/plant, not significantly different from applying 100 % NPK and the combination of 50 % cow manure + 50 % NPK, and terpenoid productivity of 77.51 mmol Nerol Equivalent/plant. The 11α-OH KA productivity and antioxidant capacity of this fertilizer is 18.00 mM 11α-OH KA/plant and 601.76 μmol Ascorbic Acid Equivalent/g dry sample, not significantly different from applying 100 % NPK. Applying 100 % cow manure + 100 % NPK may enhance the medicinal plant A. madurense 's efficacy, especially for antioxidants. [ABSTRACT FROM AUTHOR]

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Terpenoids are widely used in the food, beverage, cosmetics, and pharmaceutical industries. Microorganisms have been extensively studied for terpenoid production. In yeast, the introduction of the mevalonate (MVA) pathway in organelles in addition to the augmentation of its own MVA pathway have been challenging. Introduction of the MVA pathway into mitochondria is considered a promising approach for terpenoid production because acetyl-CoA, the starting molecule of the MVA pathway, is abundant in mitochondria. However, mitochondria comprise only a small percentage of the entire cell. Therefore, we hypothesized that increasing the total mitochondrial volume per cell would increase terpenoid production. First, we ascertained that the amounts of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), the final molecules of the MVA pathway, were 15-fold higher of the strain expressing the MVA pathway in mitochondria than in the wild-type yeast strain. Second, we found that different deletion mutants induced different mitochondrial volumes by measuring the mitochondrial volume in various deletion mutants affecting mitochondrial morphology; for example,Δmdm32 increased mitochondrial volume, and Δfzo1 decreased it. Finally, the effects of mitochondrial volume on amounts of IPP/DMAPP and terpenoids (squalene or β-carotene) were investigated using mutants harboring large or small mitochondria expressing the MVA pathway in mitochondria. Amounts of IPP/DMAPP and terpenoids (squalene or β-carotene) increased when the mitochondrial volume expanded. Introducing the MVA pathway into mitochondria for terpenoid production in yeast may become more attractive by enlarging the mitochondrial volume. Key points: • IPP/DMAPP content increased in the strain expressing the MVA pathway in mitochondria • IPP/DMAPP and terpenoid contents are positively correlated with mitochondrial volume • Enlarging the mitochondria may improve mitochondria-mediated terpenoid production [ABSTRACT FROM AUTHOR]

Plant secondary metabolites can protect organisms against oxidative stress caused by adverse environmental conditions. Cinnamomum camphora (L.) J. Presl contains plentiful terpenoids and is subdivided into 5 chemotypes. To develop natural antioxidants using the plant terpenoids, the terpenoid composition and antioxidant abilities of methanol, ethyl acetate, n-hexane and petroleum ether extracts from linalool and eucalyptol chemotypes were investigated, and the solvent effects on in vitro antioxidant activity of 8 main terpenoids were analyzed. Meanwhile, the in vivo effects of two strong antioxidant terpenoids were evaluated. For the two chemotypes, the 4 solvents exhibited the same extracting effects on the terpenoid types, but methanol extracts contained the highest content of terpenoids, which should contribute to their strongest scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) free radicals. In linalool and eucalyptol chemotype extracts, linalool, eucalyptol, ocimene, α-pinene, D-limonene, terpinene, β-pinene and longifolene were the 8 main terpenoids. Among the 4 solvents, the 8 terpenoids showed the strongest free radical-scavenging activity with methanol as the reaction medium, which might result from strong-polarity methanol easily activating C = C unsaturated bonds in these compounds. This might also contribute to the strongest scavenging activity of methanol extracts against free radicals. Among these main components, ocimene and longifolene separately showed the strongest activity in scavenging DPPH and ABTS free radical. In in vivo assay, the two compounds significantly lowered the reactive oxygen species (ROS) levels in Chlamydomonas reinhardtii, a single-celled model organism, under H2O2 stress, and the lowering effects gradually enhanced with increasing the compound concentration, resulting in the corresponding promoting effect on the algal growth. At the same concentration, longifolene showed the strongest effect on protecting the algal cells against oxidative stress. Therefore, methanol was suitable for extracting terpenoids in natural antioxidant development, and ocimene and longifolene were two strong antioxidant terpenoids without cell toxicity, with the latter having stronger in vivo antioxidant activity. [ABSTRACT FROM AUTHOR]

The present study aims to publicize the chemical composition and possible medicinal potential of varieties of non-psychoactive cannabis grown in the department of Cauca. Cannabinoids were identified and quantified by high-performance liquid chromatography coupled to an ultraviolet detector (HPLC/UV) for the analysis of the flower, and gas chromatography coupled to a mass spectrometer (GC-MS) for the analysis of the ethanolic extracts and content terpenes. Phenols were quantified by reaction with the Folin & Ciocalteau reagent; for the determination of flavonoids and anthraquinones, the extracts were treated with A1C13. Finally, to determine the antioxidant activity, three methods were used: DPPH, ABTS and FRAP. It was possible to determine that varieties A and B contained percentages of total tetrahydrocannabinol (THC) less than 1 % and percentages of total cannabidiol (CBD) between 9-15 %. In the ethanolic extracts concentrations (w/w) of CBD were reached in varieties A and B, of 10% and 13.7 %, respectively. Nine terpenes from sample A and seven from sample B were identified and quantified, with β--caryophyllene being the most abundant in both. Considering that there is evidence in the literature that the CBD/THC ratio influences biological activity, ethanolic extracts of varieties A and B are expected to have moderate to low antioxidant activity, which, according to some researchers, it may be associated with the neuroprotective effect, which may be favored by the presence of β--caryophyllene. [ABSTRACT FROM AUTHOR]

Long non-coding RNAs (lncRNAs) have emerged as curial regulators of diverse biological processes in plants. Jasmine (Jasminum sambac) is a world-renowned ornamental plant for its attractive and exceptional flower fragrance. However, to date, no systematic screening of lncRNAs and their regulatory roles in the production of the floral fragrance of jasmine flowers has been reported. In this study, we identified a total of 31,079 novel lncRNAs based on an analysis of strand-specific RNA-Seq data from J. sambac flowers at different stages. The lncRNAs identified in jasmine flowers exhibited distinct characteristics compared with protein-coding genes (PCGs), including lower expression levels, shorter transcript lengths, and fewer exons. Certain jasmine lncRNAs possess detectable sequence conservation with other species. Expression analysis identified 2752 differentially expressed lncRNAs (DE_lncRNAs) and 8002 DE_PCGs in flowers at the full-blooming stage. DE_lncRNAs could potentially cis- and trans-regulate PCGs, among which DE_lincRNAs and their targets showed significant opposite expression patterns. The flowers at the full-blooming stage are specifically enriched with abundant phenylpropanoids and terpenoids potentially contributed by DE_lncRNA cis-regulated PCGs. Notably, we found that many cis-regulated DE_lncRNAs may be involved in terpenoid and phenylpropanoid/benzenoid biosynthesis pathways, which potentially contribute to the production of jasmine floral scents. Our study reports numerous jasmine lncRNAs and identifies floral-scent-biosynthesis-related lncRNAs, which highlights their potential functions in regulating the floral scent formation of jasmine and lays the foundations for future molecular breeding. [ABSTRACT FROM AUTHOR]

With the gradual deepening of the concept of sustainable development, the world is transitioning from an energy economy driven by fossil fuels to one that is supplied by more renewable and sustainable materials. Consequently, scientists, engineers, the public, and government agencies have increased their focus on the sustainable and renewable materials derived from natural resources. Terpenoids, a category of natural products existed in plants, microorganisms and marine animals, have numerous modification sites and diverse functions. It can be used to create sustainable materials, which is able to simplify the synthesis process of materials while also giving them a distinctive stereoscopic configuration, superior bioactivity, and biocompatibility, allowing for greater application in tissue engineering, surface coating, flexible electronic devices, and other applications. Depending on the different application fields of terpenoids, the focus of this review is to shed light on the recent advances in the preparation, properties, and development directions of sustainable and multifunctional materials from terpenoids, including 1) terpenoid-derived thermoplastics, 2) terpenoid-derived cross-linked polymers, and 3) terpenoid-derived supramolecular materials. This review aims to raise attention to natural terpenoids, promote their exploitation and utilization, and provide more alternatives for the advancement of sustainable functional materials. [ABSTRACT FROM AUTHOR]

Terpenoids are used in various industries, and Saccharomyces cerevisiae is a promising microorganism for terpenoid production. Introducing the mevalonate (MVA) pathway into the mitochondria of a strain with an augmented inherent cytosolic MVA pathway increased terpenoid production but also led to the accumulation of toxic pyrophosphate intermediates that negatively affected terpenoid production. We first engineered the inherent MVA pathway in the cytosol and then introduced the MVA pathway into the mitochondria using several promoter combinations, considering the toxicity of pyrophosphate intermediates. However, the highest titer, 183 mg/L, tends to be only 5% higher than that of the strain that only augmented the inherent MVA pathway (SYCM1; 174 mg/L). Next, we hypothesized that, in addition to the toxicity of pyrophosphate, other compounds in the MVA pathway could affect the squalene titer. Thus, we constructed a combinatorial strain library expressing MVA pathway enzymes in the mitochondria with various promoter combinations. The highest squalene titer (230 mg/L) was 32% higher than that of SYCM1. The promoter set revealed that mitigation of mono- and pyrophosphate compound accumulation was important for mitochondrial usage. This study demonstrated that a combinatorial strain library is useful for discovering the optimal gene expression balance in engineering yeast. [ABSTRACT FROM AUTHOR]

This study was conducted to investigate the effects of auxin and gibberellin on Euphorbia trigona Mill. in a randomized complete block design in greenhouse conditions in 2020. One minute pretreatments including auxin regulators of NAA, IBA and IAA at a concentration of 500 mg / l and treatments containing GA, IAA, IBA and NAA, 250 mg / l were applied and compared with each other and with control plants. Fresh and dry weights of stems and roots, dry weight percentage, total photosynthetic pigments content, and total terpenoids were measured. Fresh and dry weight and the percentage of dry weight of stem did not show sensitivity to the treatments and pretreatments, and the effects were not significant. NAA treatment had the most positive effect on root fresh and dry weight, although the percentage of root dry weight was not significantly affected by the treatments. The highest significant increase in terpenoid content was observed in NAA treatment and NAA and IBA pretreatments. GA treatment had the most positive effects on the content of chlorophylls a, b, total and carotenoid content. In terms of effects on photosynthetic antenna composition, the most positive effects on the ratio of total chlorophyll to carotenoids were observed in GA, NAA, IAA treatments and IAA pretreatment. IAA treatment also showed a significant increase in chlorophyll a to b ratio. The correlation between growth parameters with each other and also the correlation of chlorophyll content with each other and with carotenoids were positive and significant. However, the correlation of terpenoid content with none of the other traits was significant. On the other hand and from an application point of view, based on gas chromatography-mass spectrometry measurements, naphthalene-acetic-acid treatment was effective in severely increasing the content of valuable medicinal compound, bis-2-ethylhexyl phthalate, compared to the control. [ABSTRACT FROM AUTHOR]

Key message: This review summarized how TFs function independently or in response to environmental factors to regulate terpenoid biosynthesis via fine-tuning the expression of rate-limiting enzymes. Terpenoids are derived from various species and sources. They are essential for interacting with the environment and defense mechanisms, such as antimicrobial, antifungal, antiviral, and antiparasitic properties. Almost all terpenoids have high medicinal value and economic performance. Recently, the control of enzyme genes on terpenoid biosynthesis has received a great deal of attention, but transcriptional factors regulatory network on terpenoid biosynthesis and accumulation has yet to get a thorough review. Transcription factors function as activators or suppressors independently or in response to environmental stimuli, fine-tuning terpenoid accumulation through regulating rate-limiting enzyme expression. This study investigates the advancements in transcription factors related to terpenoid biosynthesis and systematically summarizes previous works on the specific mechanisms of transcription factors that regulate terpenoid biosynthesis via hormone signal–transcription regulatory networks in plants. This will help us to better comprehend the regulatory network of terpenoid biosynthesis and build the groundwork for terpenoid development and effective utilization. [ABSTRACT FROM AUTHOR]

Background: Cannabis sativa, a dioecious plant that has been cultivated worldwide for thousands of years, is known for its secondary metabolites, especially cannabinoids, which possess several medicinal effects. In this study, we investigated the autopolyploidization effects on the biosynthesis and accumulation of these metabolites, transcriptomic and metabolomic analyses were performed to explore the gene expression and metabolic variations in industrial hemp autotetraploids and their diploid progenitors. Results: Through these analyses, we obtained 1,663 differentially expressed metabolites and 1,103 differentially expressed genes. Integrative analysis revealed that phenylpropanoid and terpenoid biosynthesis were regulated by polyploidization. No substantial differences were found in the cannabidiol or tetrahydrocannabinol content between tetraploids and diploids. Following polyploidization, some transcription factors, including nine bHLH and eight MYB transcription factors, affected the metabolic biosynthesis as regulators. Additionally, several pivotal catalytic genes, such as flavonol synthase/flavanone 3-hydroxylase, related to the phenylpropanoid metabolic pathway, were identified as being modulated by polyploidization. Conclusions: This study enhances the overall understanding of the impact of autopolyploidization in C. sativa and the findings may encourage the application of polyploid breeding for increasing the content of important secondary metabolites in industrial hemp. [ABSTRACT FROM AUTHOR]

Little is known concerning terpenoids produced by members of the fungal order Ophiostomales, with the member Harringtonia lauricola having the unique lifestyle of being a beetle symbiont but potentially devastating tree pathogen. Nine known terpenoids, including six labdane diterpenoids (1–6) and three hopane triterpenes (7–9), were isolated from H. lauricola ethyl acetate (EtOAc) extracts for the first time. All compounds were tested for various in vitro bioactivities. Six compounds, 2, 4, 5, 6, 7, and 9, are described functionally. Compounds 2, 4, 5, and 9 expressed potent antiproliferative activity against the MCF-7, HepG2 and A549 cancer cell lines, with half-maximal inhibitory concentrations (IC50s) ~12.54–26.06 μM. Antimicrobial activity bioassays revealed that compounds 4, 5, and 9 exhibited substantial effects against Gram-negative bacteria (Escherichia coli and Ralstonia solanacearum) with minimum inhibitory concentration (MIC) values between 3.13 and 12.50 μg/mL. Little activity was seen towards Gram-positive bacteria for any of the compounds, whereas compounds 2, 4, 7, and 9 expressed antifungal activities (Fusarium oxysporum) with MIC values ranging from 6.25 to 25.00 μg/mL. Compounds 4, 5, and 9 also displayed free radical scavenging abilities towards 2,2-diphenyl-1-picrylhydrazyl (DPPH) and superoxide (O2−), with IC50 values of compounds 2, 4, and 6 ~3.45–14.04 μg/mL and 22.87–53.31 μg/mL towards DPPH and O2−, respectively. These data provide an insight into the biopharmaceutical potential of terpenoids from this group of fungal insect symbionts and plant pathogens. [ABSTRACT FROM AUTHOR]

Nanoscale three-dimensional (3D) network morphologies, such as those represented by gyroids accessed by the self-assembly of block copolymers, are highly attractive platforms for the fabrication of nanostructured materials. However, it remains challenging to access such morphologies, especially in the sub-10 nm domain spacing region. Herein, we systematically investigated the microphase separation behaviors of biobased sugar–terpenoid hybrid block co-oligomers (BCOs) with different molecular parameters, including their volume fractions, the linker structures between the blocks, and the stereochemistries of the terpenoid blocks. The BCOs were synthesized using the azido–alkyne click reaction of propargyl-β-d-glucopyranoside with azido-functionalized farnesol, phytol, DL-α-tocopherol, and d-α-tocopherol, to ensure a well-defined molecular structure without any molecular weight distribution. Through X-ray scattering screening, we found that tocopherols, when combined with a glucose unit, yield BCOs capable of forming gyroid and hexagonally perforated lamellar (HPL) 3D network morphologies with ultrasmall domain spacings of ∼10 nm. Remarkably, HPL, which is known as a metastable phase in block copolymers, was obtained in both the bulk and film states. The nature of the linker structure and the stereochemistry of the tocopherol hydrocarbon chain were found to influence the resulting morphology and the long-range order of the nanostructures. We expect this study to contribute to the molecular design of precise block copolymers and the construction of intricate nanostructural templates with ultrasmall feature sizes.

Context: Curcuma xanthorrhiza, a native to Indonesia, has been recognized as a potential medicinal plant. Xanthorrhizol (XTZ), curcumin (Cur), bisdemethoxycurcumin (BDMC), and demethoxycurcumin (DMC) are the main major metabolites with different bioactivities. Thus, the selective extraction of these markers is required. Aims: To characterize and use natural deep eutectic solvents (NADES) for the extraction of XTZ and curcuminoids (CURS) from C. xanthorrhiza. Methods: Four NADES, comprising of glucose:lactic acid (Glu:LA, 1:3), choline chloride: malic acid (ChCl:MA, 1:1), choline chloride: glycerol (ChCl:Gly, 1:1), and choline chloride: sucrose (ChCl:Suc, 3:1) were synthesized and subjected to FTIR. The physicochemical properties of NADES were characterized, including polarity, viscosity, and density. Their antioxidant profiles were evaluated. The toxicity of NADES was assessed towards Escherichia coli by real-time growth monitoring. Tested NADES were employed to extract marker compounds from the rhizome of C. xanthorrhiza. A validated high-performance liquid chromatography (HPLC) method was applied to simultaneously quantify XTZ and CURS in NADES extracts. Results: FTIR spectra confirmed the formation of hydrogen bonds between components. Using the DPPH and FRAP methods, all NADES and NADES extracts displayed antioxidative activity, suggesting the contribution of NADES to the activity. Of the tested NADES, Glu:LA (1:3) obtained the highest content of XTZ over Cur, BDMC, and DMC, comparable to that of ethanol maceration. All tested NADES were harmless to E. coli, except for ChCl:MA (1:1). However, NADES extracts of Glu:LA (1:3) and ChCl:MA (1:1) suppressed the growth of the bacterium. Scanning electron micrographs demonstrated the destruction of the surface structure of the rhizome powder by NADES-ultrasonication. Conclusions: The study recommended the use of Glu:LA (1:3) to selectively extract XTZ to promote environmentally friendly and sustainable extraction.

Sorbitol is an important source of abiotic stress that is used to increase osmolality in cell cultures. It increases the antioxidant enzymes of defense catalase (CAT), peroxidase (POD), and superoxide dismutase (SOD) in the stress state of cells. Sorbitol plays an important role in stimulating these enzymes in cells and increasing phenylalanine ammonium lyase (PAL) activity. The aim of this study was to apply increasing doses of sorbitol elicitor to cell suspension cultures to determine the changes in cell number, viability, dry weight, and camphor content. In vitro plantlets were obtained from plant seeds and stem segments of these plants were used as explant source. Cell cultures were established after callus formation. Then, 0 (control), 5, 25, and 50 g L-1 sorbitol was dissolved in distilled water and cultured. Samples were taken three times in total, starting from day 1 to day 3. The content of camphor was detected by gas chromatography-mass spectrometry (GC-MS). Cell number, viability,dry weight, and camphor content increased significantly with increasing doses of sorbitol compared to sampling times. Compared to the initial culture, the amount of camphor increased by 40% at the 5 g L-1 dose, 82% at the 25 g L-1 dose, and 154% at the 50 g L-1 dose. In A. gypsicola cell cultures, increasing doses of sorbitol have clearly demonstrated the secondary metabolite accumulation and its positive effect on cell growth.

Cadmium (Cd) contamination poses a substantial threat the environment, necessitating effective remediation strategies. Phytoremediation emerges as a cost-efficient and eco-friendly approach for reducing Cd levels in the soil. In this study, the suitability of A. venetum for ameliorating Cd-contaminated soils was evaluated. Mild Cd stress promoted seedling and root growth, with the root being identified as the primary tissue for Cd accumulation. The Cd content of roots ranged from 0.35 to 0.55 mg/g under treatment with 10–50 µM CdCl2·2.5 H2O, and the bioaccumulation factor ranged from 28.78 to 84.43. Transcriptome sequencing revealed 20,292 unigenes, and 7507 nonredundant differentially expressed genes (DEGs) were identified across five comparison groups. DEGs belonging to the “MAPK signaling pathway-plant,” “monoterpenoid biosynthesis,” and “flavonoid biosynthesis pathway” exhibited higher expression levels in roots compared to stems and leaves. In addition, cytokinin-related DEGs, ROS scavenger genes, such as P450, glutathione-S-transferase (GST), and superoxide dismutase (SOD), and the cell wall biosynthesis-related genes, CSLG and D-GRL, were also upregulated in the root tissue, suggesting that Cd promotes root development. Conversely, certain ABC transporter genes, (e.g, NRAMP5), and some vacuolar iron transporters, predominantly expressed in the roots, displayed a strong correlation with Cd content, revealing the mechanism underlying the compartmentalized storage of Cd in the roots. KEGG enrichment analysis of DEGs showed that the pathways associated with the biosynthesis of flavonoids, lignin, and some terpenoids were significantly enriched in the roots under Cd stress, underscoring the pivotal role of these pathways in Cd detoxification. Our study suggests A. venetum as a potential Cd-contaminated phytoremediation plant and provides insights into the molecular-level mechanisms of root development promotion and accumulation mechanism in response to Cd stress.

Enzyme spatial organization is an evolved mechanism for facilitating multi‐step biocatalysis and can play an important role in the regulation of promiscuous enzymes. The latter function suggests that artificial spatial organization can be an untapped avenue for controlling the specificity of bioengineered metabolic pathways. A promiscuous terpene synthase (nerolidol synthase) is co‐localized and spatially organized with the preceding enzyme (farnesyl diphosphate synthase) in a heterologous production pathway, via translational protein fusion and/or co‐encapsulation in a self‐assembling protein cage. Spatial organization enhances nerolidol production by ≈11‐ to ≈62‐fold relative to unorganized enzymes. More interestingly, striking differences in the ratio of end products (nerolidol and linalool) are observed with each spatial organization approach. This demonstrates that artificial spatial organization approaches can be harnessed to modulate the product profiles of promiscuous enzymes in engineered pathways in vivo. This extends the application of spatial organization beyond situations where multiple enzymes compete for a single substrate to cases where there is competition among multiple substrates for a single enzyme. [ABSTRACT FROM AUTHOR]

Cannabinoids are important therapeutical molecules for human ailments, cancer treatment, and SARS-CoV-2. The central cannabinoid, cannabigerolic acid (CBGA), is generated from geranyl pyrophosphate and olivetolic acid by Cannabis sativa prenyltransferase (CsPT4). Despite efforts to engineer microorganisms such as Saccharomyces cerevisiae (S. cerevisiae) for CBGA production, their titers remain suboptimal because of the low conversion of hexanoate into olivetolic acid and the limited activity and stability of the CsPT4. To address the low hexanoate conversion, we eliminated hexanoate consumption by the beta-oxidation pathway and reduced its incorporation into fatty acids. To address CsPT4 limitations, we expanded the endoplasmic reticulum and fused an auxiliary protein to CsPT4. Consequently, the engineered S. cerevisiae chassis showed a marked improvement of 78.64-fold in CBGA production, reaching a titer of 510.32 ± 10.70 mg l−1 from glucose and hexanoate. • Commercial production of cannabigerolic acid (CBGA) in S. cerevisiae presents challenges. • Blocking hexanoate degradation and optimizing pathway enzyme expression resulted in improved CBGA titers. • Fatty acid synthase confirmed cryptical utilization of hexanoyl-CoA. • Compartmentalization expansion and auxiliary partner fusion elevated activity and stability of prenyltransferase CsPT4. • Engineered CBGA-producing yeast yielded in 510 mg l−1 CBGA from cost-effective carbon source glucose and hexanoate. [ABSTRACT FROM AUTHOR]

Coconut haustorium (CH) is formed inside coconut shell during coconut germination. This study aimed to investigate the compositions and contents of CH phytochemicals. Phytochemical compositions and contents in CH were analyzed by ultra-high performance liquid chromatography–tandem mass spectrometry (UHPLC–MS/MS) and spectrophotometrical method. Five phenolic acids and four flavonoids were identified in CH. Ferulic acid and myricetin were the most abundant among phenolic acids and flavonoids identified in CH, respectively. Nepetariaside and 1-methylene-5α-androstan-3α-ol-17-one glucuronide were the most abundant terpenoids and steroid derivatives identified in CH, respectively. To our knowledge, this study screened several classes of phytochemicals in CH for the first. Terpenoids and steroid derivatives were likely to be more major phytochemicals than phenolic acids and flavonoids in CH. The functionality of CH itself and the compounds found in CH might be utilized in functional foods or cosmetics. [ABSTRACT FROM AUTHOR]