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Aims: A paper by Araújo et al. (2018) claims that a variety of compounds present in pyroligneous acid (guaiacol, phenols and furfural) are responsible for the observed antimicrobial activity. We show, on the other hand, that the low pH due to acetic acid present in pyroligneous acid is the real cause of the activity., Methods and Results: Pyroligneous acid (PA) was synthesized according to a previous method (Medeiros et al. 2019) with its inhibition activity tested on Escherichia coli and Staphylococcus aureus via the agar diffusion method. The activity of acetic acid at different concentrations was also evaluated for comparison. As expected, crude PA (pH 3.0) and acetic acid produced inhibition halos whose diameters varied according to their employed concentration. However, any PA inhibitory activity completely vanished upon neutralization (pH 7.0), a behaviour also observed for neutralized acetic acid., Conclusions: The claim that guaiacol, phenols and furfural are responsible for any inhibitory activity is unsubstantiated. The authors should have neutralized the pyroligneous acid if any activity was to be discovered., Significance and Impact of Study: To increase awareness that interfering species may play a detrimental role on the interpretation of results. In this case, the action of acetic acid is vastly more important for the inhibitory activity than any other compound present in PA., (© 2021 The Society for Applied Microbiology.)

Archival documents and artworks stored in libraries frequently undergo degradative processes promoted by the so-called "biodeteriogens" that inhabit these places. A renewed interest in plant-derived products has arisen in those research groups focusing on cultural heritage preservation and looking for new and safe disinfection techniques. In this view, essential oils (EOs) and their volatile organic constituents are very appealing thanks to their versatility of action. A literature survey of the scientific publications involving EOs and/or their major constituents related to the conservation of paper items of cultural heritage interest is presented here, aiming to reveal benefits and limitations of such peculiar plant-derived compounds. [ABSTRACT FROM AUTHOR]

Capitalizing on the late-stage diversification of an essential 1,3-diene intermediate, we describe herein a 9-step enantioselective total synthesis of (+)-hyperforin and (+)-pyrohyperforin, starting from commercially available allylacetone. Our convergent synthesis features a series of critical reactions: 1) an enantioselective deconjugative α-alkylation of α,β-unsaturated acid using chiral lithium amides as noncovalent stereodirecting auxiliaries; 2) a HfCl 4 -mediated carbonyl α-tert-alkylation to forge the intricate bicyclo[3.3.1]nonane framework; 3) an abiotic cascade pyran formation; and 4) a selective 1,4-semihydrogenation of polyenes. During the course of our synthesis, we also identified a 1,2-cyclopropanediol overbred intermediate which was responsible for the 1,3-diene precursor formation through a controlled fragmentation., (© 2022 Wiley-VCH GmbH.)

Gonystylus bancanus wood or ramin wood has been generally known as a source of agarwood (gaharu) bouya, a kind of agarwood inferior type, or under the exported trading name of aetoxylon oil. The massive exploitation of ramin wood is causing this plant's extinction and putting it on Appendix II CITES and IUCN Red List of Threatened Species. To date, no scientific publication concerns the chemical exploration of G. bancanus wood and preserving this germplasm through its metabolite profiling. Therefore, research focused on chemical components profiling of G. bancanus is promised. This research is aimed to explore metabolomics and analyze the influence of solvent polarities on the partitioning of metabolites in G. bancanus wood. A range of solvents in different polarities was applied to provide comprehensive extraction of metabolites in G. bancanus wood. Moreover, a hydrodistillation was also carried out to extract the volatile compounds despite the non-volatile ones. LCMS and GCMS analyses were performed to identify volatile and non-volatile components in the extracts and essential oil. Multivariate data analysis was processed using Principal Component Analysis (PCA) and agglomerative hierarchical clustering. 142 metabolites were identified by LCMS analysis, while 89 metabolites were identified by GCMS analysis. Terpenoids, flavonoids, phenyl propanoids, and saccharides are some major compound classes available from LCMS data. Oxygenated sesquiterpenes, especially 10-epi-γ-eudesmol, and β-eudesmol, are the major volatile components identified from GCMS analysis. PCA of LCMS analysis demonstrated that PC1 discriminated two clusters: essential oil, dichloromethane, and n-hexane extracts were in the positive quadrant, while methanol and ethyl acetate extracts were in the negative quadrant. Three-dimensional analysis of GCMS data revealed that n-hexane extract was in the superior quadrant, and its composition can be significantly distinguished from other extracts and essential oil. G. bancanus wood comprises valuable metabolites, i.e., terpenoids, which benefit the essential oil industry. Comprehensive extraction by performing solvents in different polarities on G. bancanus wood could allow exploration of fully extracted metabolites, supported by the exhibition of identified metabolites from LCMS and GCMS analysis., (© 2023. Springer Nature Limited.)

Many terpenoids with isoprene unit(s) demonstrating critical biological activities have been isolated and characterized. In this study, we have developed a robust chem-stamp strategy for the construction of the key isoprene unit, which consists of two steps: one-carbon extension of aldehydes to the alkenyl boronates by the boron-Wittig reaction and the rhodium-catalyzed reaction of alkenyl boronates with 2,3-allenols to yield enals. This chem-stamp could readily be applied repeatedly and separately, enabling the modular concise synthesis of many natural and pharmaceutically active terpenoids, including retinal, β-carotene, vitamin A, tretinoin, fenretinide, acitretin, ALRT1550, nigerapyrone C, peretinoin, and lycopene. Owing to the diversified availability of the starting materials, aldehydes and 2,3-allenols, creation of new non-natural terpenoids has been realized from four dimensions: the number of isoprene units, the side chain, and the two terminal groups., (© 2023 Wiley-VCH GmbH.)

In order to search for bio-rational and eco-friendly pest control agents to protect crops from insect infestation, while avoiding the toxic hazards of chemical pesticides, essential oils (EOs) were hydrodistilled from Juniperus procera and Thymus vulgaris and analyzed using gas chromatography–flame ionization detection (GC–FID), and gas chromatography–mass spectrometry (GC–MS). Eugenol (71.3%), β-caryophyllene (11.8%), and α-pinene (6.1%) were isolated as the major components of J. procera EO, whereas thymol (58.1%), p-cymen (10.3%), and carvacrol (8.3%) were the main terpenes in T. vulgaris EO. The EOs and terpenes exhibited considerable bioactivity against the khapra beetle using the contact and fumigation bioassays, where T. vulgaris EO was superior in bioactivity. Among the terpenes tested, carvacrol and eugenol were superior. Regarding contact toxicity using impregnated filter paper and after 24 h of exposure, the LC50 values ranged between 21.4 and 77.0 µL/cm2 against larvae and between 16.1 and 69.6 µL/cm2 against adults. After 48 h, these values decreased remarkably. Upon fumigation and after 48 h of exposure, the LC50 values ranged between 23.0 and 65.3 µL/L against larvae, and from 14.2 to 56.4 µL/L against adults. The botanicals effectively inhibited the acetylcholinesterase activity of the larvae; however, they were safe for the earthworm E. fetida and did not alter the viability of wheat grains. There is a potential for using these botanicals to control T. granarium. However, further investigations are needed to confirm the safety of these phytochemicals before use as grain protectants on a commercial scale. [ABSTRACT FROM AUTHOR]

Plant essential oils have been used for hundreds of years as natural medicines to combat a multitude of pathogens, including bacteria, fungi, and viruses. The paper reports the chemical compositions of essential oil hydrodistilled from the leaves and rhizomes of Amomum unifolium Gagnep. from Vietnam. The main classes of compounds present in the essential oils were monoterpene hydrocarbons (10.1% and 23.9%, respectively), oxygenated monoterpenes (14.5% and 4.9%, respectively), sesquiterpene hydrocarbons (40.9% and 21.9%, respectively), and oxygenated sesquiterpenes (20.1% and 26.8%, respectively). Diterpenes (16.1%) were identified in sizeable proportion in the rhizome essential oil. The constituents occurring in higher amounts in the leaf essential oil were aromadendrene (6.9%), occidenol (6.8%), β-phellandrene (6.2%), β-elemene (5.7%), and δ-elemene (5.0%). However, the main compounds of the rhizome essential oil were β-phellandrene (18.5%), torulosol (16.1%), germacrene D (5.7%), α-cadinol (5.5%) and (6S, 7R)-bisabolene (5.1%). The leaf essential oil of A. unifolium displayed higher antibacterial activity than the rhizome oil. The leaf oil showed activity towards S. aureus ATCC 6538, and B. pumilus ATCC 14884, with MIC values of 75.0 μg/mL and 37.5 μg/mL, respectively. On the other hand, the rhizome essential oil displayed activity against the organisms at MIC value of 150.0 μg/mL. Both essential oils exhibited antibacterial activity to E. coli ATCC 8739, with MIC value of 150.0 μg/mL. The antimicrobial activity of A. unifolium essential oils are being reported for the first time as a confirmation of the ethnomedical uses of A. unifolium in the treatment of diseases especially antimicrobial infections. Furthermore, the paper discusses the chemotaxonomy of Amomum oil samples. [ABSTRACT FROM AUTHOR]

Pyr4-family terpene cyclases are noncanonical transmembrane terpene cyclases involved in the biosynthesis of microbial meroterpenoids and catalyze diverse cyclization reactions. Despite the ubiquity of Pyr4-family terpene cyclases in microorganisms, their three-dimensional structures have never been experimentally determined. Herein, we focused on AdrI, the Pyr4-family enzyme for the andrastin A pathway, and its homologues, and performed a series of mutational experiments using their AlphaFold2-generated structures. Intriguingly, we found that AdrI and InsA7, which both accept the same substrate, use different amino acid residues for the initiation of the cyclization cascade. Furthermore, we obtained several AdrI variants with altered product selectivity, one of which dominantly yielded a new meroterpenoid species. Collectively, our study provides important insights into the catalytic functions of Pyr4-family terpene cyclases and will facilitate the engineering of these enzymes., (© 2023 Wiley-VCH GmbH.)

Herein, we describe the first total synthesis of cochlearol B, a meroterpenoid natural product featuring a 4/5/6/6/6-fused pentacyclic structure. Key steps, oxidative cyclization and subsequent intramolecular [2+2] photocycloaddition, which constructed the pentacyclic structure in highly stereoselective manner, allowed efficient access to cochlearol B with the longest linear sequence of 16 steps, and in 9 % overall yield. Single-crystal X-ray crystallographic analysis clearly confirmed the stereochemistry of cochlearol B., (© 2021 Wiley-VCH GmbH.)

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The fungal inhibitory and preservative effects of essential oils (EOs) on the dominant spoilage fungi of blue honeysuckle were investigated. First, the dominant spoilage fungi (CW1, CW3, and W53) were isolated from naturally infected blue honeysuckle and identified through morphological features, inoculation study, and rDNA-ITS analysis were matched to Alternaria alternata , Metuloidea reniformis , and Rhizopus microsporus , respectively. Next, the filter paper method determined the sensitivity of EOs to the dominant spoilage fungi, and four kinds with better antifungal effects were screened out. Two or three combinations of four EOs were evaluated using a checkerboard analysis method. The fractional inhibitory concentration index (FICI) was used to assess the interactions between the combinations. The combinations of cinnamon/oregano, cinnamon/clove, oregano/clove, and cinnamon/oregano/clove showed synergistic effects (FICI ≤0.5). The best three-oil combination had a volume ratio of 31:8:8 compared to a single oil. Finally, in vivo, experiments showed that combining triple groups of EOs could prevent the spoilage of postharvest honeysuckle. Compared with the control group, the triple groups of essential oil combination maintained the best color, quality, and flavor of blue honeysuckle berries. At the same time, the spoilage rate and the weight loss rate were reduced by 38.50% and 40.71%, respectively. Delayed spoilage time to 3–5 days and the preservation effect of blue honeysuckle was extended to 16 days. Therefore, this study provides a theoretical basis for substituting chemical preservatives and highlights the potential of using complex EOs to prolong the freshness of blue honeysuckle. [Display omitted] • The dominant spoilage fungi causing spoilage of blue honeysuckle were isolated and purified for the first time in China. • The inoculation study of blue honeysuckle showed that the spoilage rate reached 100%, which satisfied the Koch hypothesis. • The synergistic antifungal activity of essential oils on the dominant spoilage fungi was determined. • In vivo assay on blue honeysuckle confirmed the synergistic fresh-keeping effect of essential oils combination. [ABSTRACT FROM AUTHOR]

Terpenoids are a large class of natural secondary plant metabolites which are highly diverse in structure, formed from isoprene units (C-5), associated with a wide range of biological properties, including antioxidant, antimicrobial, anti-inflammatory, antiallergic, anticancer, antimetastatic, antiangiogenesis, and apoptosis induction, and are considered for potential application in the food, cosmetics, pharmaceutical, and medical industries. In plants, terpenoids exert a variety of basic functions in growth and development. This review gives an overview, highlighting the current knowledge of terpenoids and recent advances in our understanding of the organization, regulation, and diversification of core and specialized terpenoid metabolic pathways and addressing the most important functions of volatile and non-volatile specialized terpenoid metabolites in plants. A comprehensive description of different aspects of plant-derived terpenoids as a sustainable source of bioactive compounds, their biosynthetic pathway, the several biological properties attributed to these secondary metabolites associated with health-promoting effects, and their potential industrial applications in several fields will be provided, and emerging and green extraction methods will also be discussed. In addition, future research perspectives within this framework will be highlighted. Literature selection was carried out using the National Library of Medicine, PubMed, and international reference data for the period from 2010 to 2024 using the keyword "terpenoids". A total of 177,633 published papers were found, of which 196 original and review papers were included in this review according to the criteria of their scientific reliability, their completeness, and their relevance to the theme considered. [ABSTRACT FROM AUTHOR]

Terpene-based eutectic mixtures (EMs) are attractive platforms for transdermal delivery due to their solubilizing potential and ability to alter the barrier function of the stratum corneum (SC). Despite this, little is known about the effect of diluting EMs with co-solvents (CSs) on their solubility- and permeation-enhancing properties. Furthermore, insufficient attention has been paid to comparing these platforms with traditional solvents, such as propylene glycol (PG) or ethanol (EtOH). To address this gap, the present study investigates the impact of the CS content in EM:CS blends on the transdermal delivery of clotrimazole (CLOT). Two CSs, PG and EtOH, and two terpene-based EMs, menthol:thymol and thymol:β-citronellol, were used. Each of the EMs was investigated at two different molar ratios between the terpenes, with one being their eutectic point, to explore its potential benefit for skin permeation. At each step, properties of the blends were compared with those of pure CSs. The EM:CS blends showed a better solubilizing potential for CLOT than EMs or CSs on their own. A higher content of CSs in the blends resulted in a higher skin permeation and retention of CLOT, and a lower degree of disarrangement of the SC structure. Furthermore, the blends of EMs at their EPs led to overall poorer permeation profiles, implying that the permeation rate is more affected by the properties of the individual terpenes than by the specific ratio at the eutectic point between them. In conclusion, addition of CSs to the EMs promotes permeation and retention of CLOT, while reducing the skin impairment caused by the terpenes., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 The Author(s). Published by Elsevier B.V. All rights reserved.)

Aspergillus carbonarius, a common food-contaminating fungus, produces ochratoxin A (OTA) and poses a risk to human health. This study aimed to assess the inhibitory activity of tea tree essential oil and its main components, Terpene-4-ol (T4), α-terpineol (αS), and 3-carene (3C) against A. carbonarius. The study showed αS and T4 were the main antifungal components of tea tree essential oil, which primarily inhibit A. carbonarius growth through cell membrane disruption, reducing antioxidant enzyme activities (catalase, peroxidase, superoxide dismutase) and interrupting the tricarboxylic acid cycle. Furthermore, αS and T4 interacted with enzymes related to OTA biosynthesis. Molecular docking and molecular dynamics show that they bound mainly to P450 with a minimum binding energy of -7.232 kcal/mol, we infered that blocking the synthesis of OTA precursor OTβ. Our hypothesis was preliminarily verified by the detection of key substances in the OTA synthesis pathway. The results of UHPLC-QTOF-MS 2 analysis demonstrated that T4 achieved a degradation rate of 43 % for OTA, while αS reached 29.6 %, resulting in final breakdown products such as OTα and phenylalanine. These results indicated that α-terpinol and Terpene-4-ol have the potential to be used as naturally safe and efficient preservatives or active packaging to prevent OTA contamination., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 The Author(s). Published by Elsevier Ltd.. All rights reserved.)

Terpenoids are ubiquitous to all kingdoms of life and are one of the most diverse groups of compounds, both structurally and functionally. Despite being derived from common precursors, isopentenyl diphosphate and dimethylallyl diphosphate, their exceptional diversity is partly driven by the substrate and product promiscuity of terpene synthases that produce a wide array of terpene skeletons. Plant terpene synthases can be subdivided into different subfamilies based on sequence homology and function. However, in many cases, structural architecture of the enzyme is more essential to product specificity than primary sequence alone, and distantly related terpene synthases can often mediate similar reactions. As such, the focus of this brief review is on some of the recent progress in understanding terpene synthase function and diversity., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

Garcinia indica, known as kokum, has been extensively researched for its therapeutic potential. Among the wide variety of phytoconstituents, garcinol is the most efficacious, holding anti-inflammatory, anti-cancer, and anti-diabetic properties. Hydrophobicity and a certain level of toxicity have constrained the drug's application and necessitated a modified dosage form design. The drug has been well explored in the form of extracts but bears very limited application in dosage forms. These prompted in implementation of protein polymers, due to non-toxicity, biocompatibility, and biodegradability. BSA encapsulates the drug, by the desolvation method. The unavailability of past exploration of garcinol with protein polymer accelerated the novelty of this study, to improve the solubility and bioavailability of the drug, modify the drug release kinetics, and ascertain the effectiveness of the NPs to combat inflammation in-vitro. NPs were characterized and satisfactory outcomes were retrieved in terms of all characterizations. The drug release studies depicted a sustained release of up to 85 % over 16 h, ensuring that garcinol can be modulated to give a desired scale of modified release. In vitro cellular uptake studies suggested a substantial uptake of NPs in cell lines and its effectiveness to mitigate inflammation was affirmed by in-vitro anti-inflammatory studies, using ELISA., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Three new sesquiterpenes, 4S-1-(3-hydroxybutyl)-7-(11-hydroxypropyl)-10-methyl- cyclohepta-7,5,10-trien-8-one (1), 8R-hydroxy-7-(4S-4,10-dimethyl-5-oxooct-1-en-7-yl)-11- methylfuran-12-one (2), (1S,5R,7S,10R)-1-hydroxy-7-(11-hydroxypropyl)-10-methyl-4- methyleneoctahydronaphthalen-8-one (3), along with 30 known terpenoids (4-33) were obtained from the rhizomes of Curcuma kwangsiensis S.G. Lee et C.F. Ling. Through comprehensive analysis of chemical evidence and spectral data including UV, ECD, IR, 1D and 2D NMR and HR-ESI-MS, as well as quantum chemical calculation, the structures of these novel compounds were successfully determined. Additionally, the inhibitory effects of compounds 1-2, 4-33 on NO production were evaluated in lipopolysaccharide (LPS)-induced RAW264.7 cells. Notably, compound 33 exhibited the most significant inhibitory effect with an IC 50 value of 3.55 ± 0.55 μM., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Isoprene chemoenzymatic cascades (ICCs) overcome the complexity of natural pathways by leveraging a streamlined two-enzyme cascade, facilitating efficient synthesis of C5-isoprene diphosphate precursors from readily available alcohol derivatives. Despite the documented promiscuity of enzymes in ICCs, exploration of their potential for accessing novel compounds remains limited, and existing methods require additional enzymes for generating longer-chain diphosphates. In this study, we present the utility of Streptococcus mutans undecaprenol kinase (SmUdpK) for the chemoenzymatic synthesis of diverse non-natural isoprenoids. Using a library of 50 synthetic alcohols, we demonstrate that SmUdpK's promiscuity extends to allylic chains as small as four carbons and benzylic alcohols with various substituents. Subsequently, SmUdpK is utilized in an ICC with isopentenyl phosphate kinase and aromatic prenyltransferase to generate multiple non-natural isoprenoids. This work provides evidence that, with proper optimization, SmUdpK can act as the first enzyme in these ICCs, enhancing access to both valuable and novel compounds., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Inc. All rights reserved.)

The continual increase in global diabetic statistics portends decreased productivity and life spans, thus making it a disease of concern requiring more effective and safe therapeutic options. While several reports on antidiabetic plants, including Hura crepitans, are available, there is still a dearth of information on the holistic antidiabetic properties of H. crepitans and its associated complications. This study evaluated the antidiabetic potential of methanolic extract of Hura crepitans using in vitro, in vivo, and in silico approaches. The extract revealed a dose-dependent in vitro effect, with a 47.97 % and 65.34 % decrease in the fasting blood sugar levels of streptozotocin (STZ) induced diabetic rats at 150 and 300 mg/kg BW, respectively. Likewise, the extract increased serum and pancreatic insulin levels, and significantly ameliorated neuronal oxidative stress and inflammation by reducing the expression levels of cholinesterase, NF-κB, and COX-2 in the brain of hyperglycemic rats. Serum dyslipidemia, liver, and kidney biomarker indices, and hematological alterations in diabetic rats were also significantly attenuated by the extract. Several constituents, mainly terpenes, were identified in the extract. To further predict the drug-likeness, pharmacokinetics, and binding properties of the compounds, in silico analysis was conducted. Ergosta-2,24-dien-26-oicacid,18-(acetyloxy)-5,6-epoxy-4, 22-dihydroxy-1-oxo-,delta.-lactone-4.beta., displayed the highest docking scores for acetylcholinesterase, butyrylcholinesterases, alpha-amylase, and nuclear factor-kB with values of -12.4, -10.9, -10.3, and -9.4 kcal/mol, while ergost-25-ene-6,12-dione,3,5-dihydroxy-, (3.beta.,5.alpha.) topped for cyclooxygenase-2 (-9.0 kcal/mol). The top-ranked compounds also presented significant oral drug-likeness, pharmacokinetics, and safety properties. Altogether, our data provide preclinical evidence of the potential of Hura crepitans in ameliorating diabetes and its associated complications., Competing Interests: Declaration of Competing Interest The authors declare no competing financial interest or personal relationship that could influence the work reported in this paper., (Copyright © 2024 The Authors. Published by Elsevier Masson SAS.. All rights reserved.)

Terpenes in essential oils (EOs) have recently received significant attention due to their potential to improve brain and whole-body health. A deeper understanding of the terpene composition of edible EOs is important for fully exploring their possible applications. In our study, we employed a comprehensive study using four different methods to analyze EO samples, including GC-MS with solid phase microextraction (SPME), liquid injection (LI), derivatization to trimethylsilyl ethers (TMSE), and LC-MS. Our findings revealed that relying on a single analytical method may be insufficient for detecting all terpenes in EOs. Despite identifying a total of 156 terpenes in the samples, only 58 were detectable across all 4 methods. To obtain a more accurate terpene profile of EOs, we advocate for the combined use of LI-GC and TMSE-GC. The terpenes detected by these two methods are complementary, enabling the detection of all terpenes with high VIP in the samples., Competing Interests: Declaration of competing interest The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Raymond Thomas reports financial support was provided by Natural Sciences and Engineering Research Council of Canada. Raymond Thomas reports financial support was provided by Atlantic Canada Opportunities Agency. Raymond Thomas reports financial support was provided by Western Research Chairs in Leadership (Western University). If there are other authors, they declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 The Authors. Published by Elsevier Ltd.. All rights reserved.)

Ten new B-ring aromatized 6/6/6-tricyclic dearomatized benzocogeijerene-based meroterpenoids with unusual methyl 1,2-shift or demethylation (2-9b), and two new geranylquinol derivatives (1 and 10), together with two known compounds (11 and 12), were isolated from the roots of Arnebia euchroma. Their structures were elucidated by extensive spectroscopic methods, X-ray diffraction crystallography, and ECD calculations. The plausible biosynthetic pathways including the unusual methyl 1,2-shfit and demethylation for B-ring aromatized 6/6/6-tricyclic meroterpenoids were discussed. Compounds 1, 2, 5, 6, 11, and 12 showed significant cardioprotective activities comparable to diltiazem against isoprenaline (ISO)-induced H9C2 cell damage in vitro. Compound 11 probably exerted heart-protective effect on ISO-induced H9C2 cells by modulating the PI3K-AKT-mTOR pathway, reducing excessive autophagy, and decreasing myocardial apoptosis., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Inc. All rights reserved.)

Dehydration is an effective method for the long-term storage and aroma retention of gonggan (Citrus sinensis Osb. 'Deqing Gonggan'), which is a Chinese variety of citrus, with unique and characteristic floral, fruity, and citrus flavors. However, the aroma profiles of gonggans prepared using oven- and freeze-drying, the most widely-used drying methods, remain unclear. In this study, a total of 911 volatile organic compounds (VOCs) were detected in dried gonggan. These were primarily composed of alcohols (7.69%), aldehydes (7.03%), esters (15.38%), ketones (7.58%), and terpenoids (23.19%). A total of 67 odorants contributed significantly to the overall aroma of dried gonggans, with the major odor qualities being detected as green, citrus, fruity, floral, and sweet. These were mainly attributed to the presence of aldehydes, esters, and terpenoids. Freeze-drying was more effective in maintaining the unique citrus and mandarin-like aromas attributed to compounds such as limonene, citrial, β-myrcene, β-pinene, and γ-terpinene. Moreover, (E,E)-2,4-decadienal had the highest relative odor activity value (rOAV) in freeze-dried gonggans, followed by (E)-2-nonenal, furaneol, (E, E)-2, 4-nonadienal, and E-2-undecenal. Oven-drying promoted the accumulation of terpenes such as octatriene, trans-β-ocimene, cyclohexanone, copaene, and ɑ-irone, imparting a soft aroma of flowers, fruits, and sweet. Increasing the temperature led to an increase in existing VOCs or the generation of new VOCs through phenylpropanoid, terpenoid, and fatty acid metabolism. The findings of this study offer insights into an optimized procedure for producing high-quality dried gonggans. These insights can be valuable for the fruit-drying industry, particularly for enhancing the quality of dried fruits., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024. Published by Elsevier Ltd.)

The genus Penicillium has provided us with the household antibiotic penicillin and the well-known lipid-lowering agent mevastatin. The strain Penicillium sp. SZ-1 was found to grow vigorously in an intact Pinus koraiensis seed, it is inferred that the strain may develop unique mechanisms associated with the biosynthesis of rare metabolites. Further fermentation of the strain on solid rice medium yielded thirteen undescribed compounds, including three andrastin-type meroterpenoids (1-3), two α-pyrone polyketides (4 and 5), and eight sesquicarane derivatives (6-13), along with seven known compounds (14-20). Their structures were determined by detailed analysis of the spectroscopic and spectrometric data (NMR and HRESIMS), in addition to comparisons of the experimental and calculated ECD data for absolute configurational assignments. The hemiacetal moiety in compounds 1 and 2 and the 3α-hydroxy group in compound 3 were rarely found in the andrastin-type meroterpenoid family. The sesquicaranes belong to a small group of sesquiterpenoid that are rarely reported. Bioassay study showed that compound 1 exhibited inhibitory effects against Staphylococcus aureus ATCC 29213 and Escherichia coli ATCC 25922 with MIC values of 64 and 32 μg/mL, respectively. In addition, compounds 1 and 3 displayed weak DPPH radical scavenging activities. The andrastins and sesquicaranes in this study enriched the structural diversity of these classes of terpenoids. Of note, this study is the first report on the metabolites of a fungus isolated from P. koraiensis seed., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

Rhododendron dauricum L. is a perennial herb belonging to the genus Rhododendron, commonly utilized in formulations for treating coughs and bronchitis, as well as in herbal teas for enhancing immunity and preventing tracheitis. In this study, fifteen previously undescribed chromene meroterpenoids (1a/1b-4a/4b, 5-8, 9b, 10a, 11b), along with twenty-one known compounds were isolated from the dried twigs and leaves of Rhododendron dauricum L. Of these, (-)-rhodonoid E (9b), (+)-confluentin (10a), and (-)-rubiginosin D (11b) were separated for the first time by chiral HPLC separation. The elucidation of their structures, including absolute configurations, was achieved through a combination of techniques such as NMR, HRESIMS, modified Mosher's method and quantum-chemical calculation of electronic circular dichroism (ECD) spectra. Seven pairs of enantiomers, compounds 1a/1b-4a/4b and 9a/9b-11a/11b, were initially obtained in a racemic manner and were further separated by chiral HPLC preparation. The biological assessment of these compounds against NO production was conducted in the LPS-induced RAW264.7 macrophage cells model. Compounds 9a, 9b, and 11a displayed inhibitory rates exceeding 80%, with IC 50 values ranging from 8.69 ± 0.94 to 13.01 ± 1.11 μM. A preliminary examination of the structure-activity relationship (SAR) for these isolates indicated that chromene meroterpenoids with α, β-unsaturated ketone carbonyl and Δ 12(13) double bond functionalities exhibited enhanced anti-inflammatory properties., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

Herpetospermum pedunculosum seeds also known as Herpetospermum caudigerum Wall. is the mature seed of the Herpetospermum pedunculosum(Ser.) C. B. Clarke,Cucurbitaceae. Modern pharmacological studies have shown that H. pedunculosum has hepatoprotective, anti-inflammatory, anti-gout and antibacterial pharmacological activities. The biologically active chemical components include lignin compounds such as Herpetin, Herpetetrone, Herpetoriol and so on. The natural product displays considerable skeletal diversity and structural complexity, offering significant opportunities for novel drug discovery. Based on the multi-omics research strategy and the 'gene-protein-metabolite' research framework, the biosynthetic pathway of terpenoids and lignans in H. pedunculosum has has been elucidated at multiple levels. These approaches provide comprehensive genetic information for cloning and identification of pertinent enzyme genes. Furthermore, the application of multi-omics integrative approaches provides a scientific means to elucidate entire secondary metabolic pathways. We investigated the biosynthetic pathways of lignin and terpene components in H. pedunculosum and conducted bioinformatics analysis of the crucial enzyme genes involved in the biosynthetic process using genomic and transcriptomic data. We identified candidate genes for six key enzymes in the biosynthetic pathway. This review reports on the current literature on pharmacological investigations of H. pedunculosum, proposing its potential as an antidiabetic agent. Moreover, we conclude, for the first time, the identification of key enzyme genes potentially involved in the biosynthesis of active compounds in H. pedunculosum. This review provides a scientific foundation for the discovery of novel therapeutic agents from natural sources., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023. Published by Elsevier B.V.)

Trypsin is a serine protease, an important digestive enzyme that digests the proteins in the small intestine. In the present study, we have investigated the interaction of safranal, a major saffron metabolite, with trypsin using spectroscopic and molecular docking analyses. Fluorescence emission spectra of trypsin were largely affected by the inner filter effect from safranal; that's why these were corrected using the standard procedure. The corrected fluorescence spectra have shown that the safranal quenched the intrinsic fluorescence of trypsin with a blue shift in the wavelength of emission maximum, which revealed that the microenvironment of the fluorophore became more hydrophobic. There was approximately 1: 1 fair binding between them, which increased with a rise in temperature. The interaction was favored, principally, by hydrophobic forces, and there was an efficient energy transfer from the fluorophore to the safranal. Synchronous fluorescence spectra suggested that the tryptophan residues were the major ones taking part in the fluorescence quenching of trypsin. Safranal also influenced the secondary structure of trypsin and caused partial unfolding. Molecular Docking and the Molecular Dynamics simulation of the free and complexed trypsin was also carried out. Safranal formed a stable, non-covalent complex within the S2'-S5' subsite. Moreover, two nearby tyrosine residues (Tyr39 and Tyr151) stabilized safranal through π-π interactions. Additionally, the presence of safranal led to changes in the protein flexibility and compactness, which could indicate changes in the surrounding of tryptophan residues, impacting their fluorescence. Furthermore, a loss in compactness is in line with the partial unfolding observed experimentally. Thus, both experimental and computational studies were in good agreement with each other., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Essential oils (EOs) are concentrated hydrophobic liquids that originate from plants and contain different bioactive chemicals and volatile substances. Several plant essential oils (PEOs) are obtained from a variety of medicinal plants and have been utilized in folk medicine and traditional pharmacopoeia. They have a long history of usage as antibacterial medicines to treat various human, animal, and plant diseases. The extraction of essential oils frequently involves fractional distillation with a variety of organic solvents. EOs can be used successfully in the food and cosmetics industries in addition to their traditional use as antimicrobial agents. This Special Issue covers various significant PEOs and their individual chemical constituents and biological-pharmaceutical functions. Further information focused on the chemical characterizations, modes of action, and biopharmaceutical properties of PEOs. This Special Issue includes seventeen research papers from different geographical zones. [ABSTRACT FROM AUTHOR]

At a time when food safety awareness is increasing, attention is paid not only to food and additives but also to packaging materials. Most current food packaging is usually made of traditional petroleum-based polymeric materials, which are not biodegradable and have adverse effects on the environment and health. In this context, the development of new non-toxic and biodegradable materials for extending the best-before date of food is receiving increasing attention. In addition, additives in packaging materials may migrate outward, resulting in contact with food. For this reason, additives are also seen as a transition from synthetic additives to natural extracts. Active extracts from animals and plants having good antioxidant and antibacterial properties are also beneficial for human health. It is indisputable that active extracts are ideal substitutes for synthetic additives. Polymer packaging materials combined with active extracts not only maintain their original mechanical and optical properties and thermal stability but also endow polymers with new functions to extend the shelf life of food. This review paper provides an overview of this promising natural extract-containing polymer-based active packaging, with a focus on plant essential oils (containing phenolics, monoterpenes, terpene alcohols, terpene ketones, and aldehydes), pigments (procyanidins), vitamins (vitamin B), and peptides (nisin). In particular, this paper covers the research progress of such active extracts, in single or compound forms, combined with diverse polymers (mostly biopolymers) for food packaging applications with particular focus on the antioxidant and antibacterial properties of packaging materials. [ABSTRACT FROM AUTHOR]

Simple Summary: The old-world sand fly, Phlebotomus papatasi (Scopoli 1786), is a major vector of Leishmania major, the predominant pathogen responsible for zoonotic cutaneous leishmaniasis in the Middle East, North Africa, Southern Europe, and Central Asia. DEET and other synthetic insect repellents have been used for personal protection against sand fly bites. However, the frequent use of DEET repellent raised concerns in regards to skin sensitivity, toxicity, and unpleasant odor. There are increasing efforts to evaluate natural products for use in developing more effective organic sand fly repellents. This paper reports the results of a laboratory study on several plant essential oils and saturated fatty acids concerning their repellency against female sand flies. A static air repellency assay was used to measure the responses of sand flies to test materials. The sand fly repellency of each test material was compared with those achieved by commercial repellent DEET and IR35353 at the same test concentration. The study identified two of the tested essential oils as effective spatial repellents at reduced concentrations compared to those of DEET, and two saturated fatty acids were found to produce significant sand fly mortality. The results from this study establish the foundation for developing more effective natural sand fly repellent products. The sand fly, Phlebotomus papatasi (Scopoli, 1786), is a major vector for Leishmania major in the Middle East, which has impacted human health and US military operations in the area, demonstrating the need to develop effective sand fly control and repellent options. Here, we report the results of spatial repellency and avoidance experiments in a static air olfactometer using the female P. papatasi testing essential oils of Lippia graveolens (Mexican oregano), Pimenta dioica (allspice), Amyris balsamifera (amyris), Nepeta cataria (catnip), Mentha piperita (peppermint), and Melaleuca alternifolia (tea tree); the 9–12 carbon saturated fatty acids (nonanoic acid, decanoic acid, undecanoic acid, and dodecanoic acid); and the synthetic repellents DEET and IR3535. The materials applied at 1% exhibited varying activity levels but were not significantly different in mean repellency and avoidance from DEET and IR3535, except in regards to nonanoic acid. Some materials, particularly nonanoic and undecanoic acids, produced sand fly mortality. The observed trends in mean repellency over exposure time included the following: (1) P. dioica oil, M. alternifolia oil, decanoic acid, undecanoic acid, DEET, and IR3535 exhibited increasing mean repellency over time; (2) oils of N. cataria, A. balsamifera, M. piperita, and dodecanoic acid exhibited relatively constant mean repellency over time; and (3) L. graveolens oil and nonanoic acid exhibited a general decrease in mean repellent activity over time. These studies identified the essential oils of N. cataria and A. balsamifera as effective spatial repellents at reduced concentrations compared to those of DEET. Additional research is required to elucidate the modes of action and potential synergism of repellents and essential oil components for enhanced repellency activity. [ABSTRACT FROM AUTHOR]

Isoprenoid metabolism and its derivatives took part in photosynthesis, growth regulation, signal transduction, and plant defense to biotic and abiotic stresses. However, how aluminum (Al) stress affects the isoprenoid metabolism and whether isoprenoid metabolism plays a vital role in the Citrus plants in coping with Al stress remain unclear. In this study, we reported that Al-treatment-induced alternation in the volatilization rate of monoterpenes (α-pinene, β-pinene, limonene, α-terpinene, γ-terpinene and 3-carene) and isoprene were different between Citrus sinensis (Al-tolerant) and C. grandis (Al-sensitive) leaves. The Al-induced decrease of CO 2 assimilation, maximum quantum yield of primary PSII photochemistry (F v /F m ), the lower contents of glucose and starch, and the lowered activities of enzymes involved in the mevalonic acid (MVA) pathway and 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway might account for the different volatilization rate of isoprenoids. Furthermore, the altered transcript levels of genes related to isoprenoid precursors and/or derivatives metabolism, such as geranyl diphosphate (GPP) synthase (GPPS) in GPP biosynthesis, geranylgeranyl diphosphate synthase (GGPPS), chlorophyll synthase (CHS) and GGPP reductase (GGPPR) in chlorophyll biosynthesis, limonene synthase (LS) and α-pinene synthase (APS) in limonene and α-pinene synthesis, respectively, might be responsible for the different contents of corresponding products in C. grandis and C. sinensis. Our data suggested that isoprenoid metabolism was involved in Al tolerance response in Citrus, and the alternation of some branches of isoprenoid metabolism could confer different Al-tolerance to Citrus species., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 The Authors. Published by Elsevier Inc. All rights reserved.)

Kaffir lime juice, often treated as production waste, can be a good source of terpenes. These compounds undergo various decomposition processes under the influence of external factors, especially during transportation and storage. In this paper, it was possible to monitor changes in the terpene profile of kaffir lime juice under different storage conditions, namely, 4 °C, 20 °C, and 35 °C. The identification of key decomposition products was achieved using gas chromatography-mass spectrometry (GC-MS) and a data mining protocol. It was followed by tracing those products in different storage conditions using a high-throughput proton transfer reaction mass spectrometry (PTR-MS) approach. Based on our findings, degradation pathways were presented, showing that the main products resulting from storage are p -cymene, p -cymenene, terpinene-4-ol, and α-terpineol. It was shown that conversion to p -cymenene occurs after 5 days of storage. Terpinene-4-ol and α-terpineol were found to be the final products of the conversion at all temperatures. Changes in the composition of terpenes are important from the point of view of their bioactive properties.

Ginkgo biloba L. is a relict plant endemic to China that is commonly considered a "living fossil". It contains unique medicinal compounds that play important roles in its response to various stresses and help maintain human health. Ginkgo terpenoids are known to be important active ingredients but have received less attention than flavonoids. Hence, this review focuses on recent progress in research on the pharmacological effects of ginkgo terpenoid and the bioactivities of different terpenoid monomers. Many key structural genes, enzyme-encoding genes, transcription factors, and noncoding RNAs involved in the ginkgo terpenoid pathway were identified. Finally, many external factors (ecological factors, hormones, etc.) that regulate the biosynthesis and metabolism of terpenoids were proposed. All these findings improve the understanding of the biosynthesis, accumulation, and medicinal functions of terpenoids. Finally, this review includes an in-depth discussion regarding the limitations of terpenoid-related studies and potential future research directions., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024. Published by Elsevier Masson SAS.)

Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. We wish to confirm that there are no known conflicts of interest associated with this publication and there has been no significant financial support for this work that could have influenced its outcome. RIFM staff are employees of the Research Institute for Fragrance Materials, Inc. (RIFM). The Expert Panel receives a small honorarium for time spent reviewing the subject work.

Owing to their extensive biological potential, essential oils (EOs) and their bioactive phytochemicals have gained attention from the scientific community. Within this domain, Terpinen-4-ol (T-4-ol), a bioactive monoterpene alcohol and the major constituent of tea tree oil (TTO), has made its way into translational research. Recent literature on T-4-ol strongly indicates its diverse pharmacological properties, including but not limited to antimicrobial, antivirulent, anti-oxidant, anti-inflammatory, anti-hypertensive, and anti-cancer effects. Hence, this review is the first to provide a comprehensive overview of the sources, bioavailability, safety, pharmaceutical delivery systems, and multifaceted biological properties of T-4-ol, emphasizing its medicinal potential for widescale application. The antibacterial and antifungal effectiveness of T-4-ol has been discussed, encompassing its role in combating a broad spectrum of bacterial and fungal pathogens. The review delves into the antivirulent prospects of T-4-ol, shedding light on its ability to attenuate virulence and mitigate bacterial pathogenesis. Scientific literature on the anti-oxidant and anti-inflammatory activity of T-4-ol highlighting its role in neutralizing reactive oxygen species and modulating inflammatory pathways has also been collated. Furthermore, the review elaborates on the cardioprotective and anti-hypertensive properties of T-4-ol and augments literature on its anti-cancer mechanism against various cancer cell lines. The review also provides in-depth knowledge of the pharmaceutical formulations of T-4-ol and recent knowledge about its application in clinical/field trials. The exploration of these diverse attributes positions T-4-ol as a promising candidate for further research and therapeutic repurposing in various biomedical applications., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2023. Published by Elsevier B.V.)

Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. We wish to confirm that there are no known conflicts of interest associated with this publication and there has been no significant financial support for this work that could have influenced its outcome. RIFM staff are employees of the Research Institute for Fragrance Materials, Inc. (RIFM). The Expert Panel receives a small honorarium for time spent reviewing the subject work.

Terpenoids are the one of most abundant natural products. With diverse varieties and biological activities, they are widely used in the food, medicine, chemical industry, and novel fuels. However, the conventional methods such as plant extraction and chemical synthesis cannot meet the current market demand for terpenoids. Efficient microbial cell factories, especially engineered Saccharomyces cerevisiae strains, have been constructed for the industrial production of terpenoids. In recent years, researchers have constructed multiple S . cerevisiae strains with increased yield and productivity via approaches of synthetic biology and metabolic engineering. This paper reviews the recent progress in the biosynthesis of terpenoids in S . cerevisiae cells and summarizes a variety of metabolic engineering strategies for the production of terpenoids in S . cerevisiae . These strategies include the construction and optimization of metabolic pathways, the mining and modification of key enzymes, the regeneration of cofactors, the engineering of cell localization and cell efflux, and the improvement of cell tolerance. Our review will provide information and strategies for the effective biosynthesis of terpenoids in S . cerevisiae .

Isoprenoids (including isoprene (ISO) and monoterpenes (MTs)) are the majority of biogenic volatile organic compounds (BVOCs) which are important carbon-containing secondary metabolites biosynthesized by organisms, especially plant in terrestrial ecosystem. Results of the warming effects on isoprenoid emissions vary within species and warming facilities, and thus conclusions remain controversial. In this study, two typical subtropical tree species seedlings of Schima superba and Cunninghamia lanceolata were cultivated under three conditions, namely no warming (CK) and two warming facilities (with infrared radiators (IR) and heating wires (HW)) in open top chamber (OTC), and the isoprenoid emissions were measured with preconcentor-GC-MS system after warming for one, two and four months. The results showed that the isoprenoid emissions from S. superba and C. lanceolata exhibited uniformity in response to two warming facilities. IR and HW both stimulated isoprenoid emissions in two plants after one month of treatment, with increased ratios of 16.3 % and 72.5 % for S. superba, and 2.47 and 5.96 times for C. lanceolata. However, the emissions were suppressed after four months, with more pronounced effect for HW. The variation in isoprenoid emissions was primarily associated with the levels of Pn, Tr, monoterpene synthase (MTPS) activity. C. lanceolata predominantly released MTs (mainly α-pinene, α-terpene, γ-terpene, and limonene), with 39.7 % to 99.6 % of the total isoprenoid but ISO was only a very minor constituent. For S. superba, MTs constituted 24.7 % to 96.1 % of total isoprenoid. It is noteworthy that HW generated a greater disturbance to physiology activity in plants. Our study provided more comprehensive and more convincing support for integrating temperature-elevation experiments of different ecosystems and assessing response and adaptation of forest carbon cycle to global warming., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024. Published by Elsevier B.V.)

Plant volatile organic compounds (PVOCs) have gained increasing attention for their role in preventing fungal spoilage and insect contamination in postharvest agro-products owing to their effectiveness and sustainability. In this study, the essential oil was extracted from fresh M. alternifolia (tea tree) leaves, and the fumigation vapor of tea tree oil (TTO) completely inhibited the growth of Aspergillus flavus on agar plates at a concentration of 1.714 μL/mL. Terpinen-4-ol was identified as the major component (40.76 %) of TTO volatiles analyzed using headspace gas chromatography-mass spectrometry. Terpinen-4-ol vapor completely inhibited the A. flavus growth on agar plates and 20 % moisture wheat grain at 0.556 and 1.579 μL/mL, respectively, indicating that terpinen-4-ol serves as the main antifungal constituent in TTO volatiles. The minimum inhibitory concentration of terpinen-4-ol in liquid-contact culture was 1.6 μL/mL. Terpinen-4-ol treatment caused depressed, wrinkled, and punctured mycelial morphology and destroyed the plasma membrane integrity of A. flavus. Metabolomics analysis identified significant alterations in 93 metabolites, with 79 upregulated and 14 downregulated in A. flavus mycelia exposed to 1.6 μL/mL terpinen-4-ol for 6 h, involved in multiple cellular processes including cell membrane permeability and integrity, the ABC transport system, pentose phosphate pathway, and the tricarboxylic acid cycle. Biochemical analysis and 2,7-dichlorofluorescein diacetate staining showed that terpinen-4-ol induced oxidative stress and mitochondrial dysfunction in A. flavus mycelia. This study provides new insights into the antifungal effects of the main TTO volatile compounds terpinen-4-ol on the growth of A. flavus., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier B.V. All rights reserved.)

Meroterpenoids discovered in Rhododendrons species possess unique chemical structures and biological activities and are expected to become new drug targets for Alzheimer's disease, metabolic disorders, and chronic kidney disease, and these compounds have attracted increasing attention in recent years. In this study, Rhododendron meroterpenoids and their structures, classifications, racemate distribution, biosynthetic pathways, chemical synthesis, and bioactivities are reviewed prior to 2023., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

Seven new meroterpenoids, paraphaeones A-G (1-7), and two new polyketides, paraphaeones H-I (8-9), along with eight known compounds (10-17), were isolated from the endophytic fungus Paraphaeosphaeria sp. C-XB-J-1. The structures of 1-9 were identified through the analysis of 1 H, 13 C, and 2D NMR spectra, assisted by HR-ESI-MS data. Compounds 1 and 7 exhibited a dose-dependent decrease in lactate dehydrogenase levels, with IC 50 values of 1.78 μM and 1.54 μM, respectively. Moreover, they inhibited the secretion of IL-1β and CASP-1, resulting in a reduction in the activity levels of NLRP3 inflammasomes. Fluorescence microscopy results indicated that compound 7 concentration-dependently attenuated cell pyroptosis. Additionally, compounds 4 and 7 showed potential inhibitory effects on the severe acute respiratory syndrome coronavirus-2 main protease (SARS-CoV-2 M pro ), with IC 50 values of 10.8 ± 0.9 μM and 12.9 ± 0.7 μM, respectively., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Inc. All rights reserved.)

Natural products play a pivotal role in drug discovery, and the richness of natural products, albeit significantly influenced by various environmental factors, is predominantly determined by intrinsic genetics of a series of enzymatic reactions and produced as secondary metabolites of organisms. Heretofore, few natural product-related databases take the chemical content into consideration as a prominent property. To gain unique insights into the quantitative diversity of natural products, we have developed the first TerPenoids database embedded with Content information (TPCN) with features such as compound browsing, structural search, scaffold analysis, similarity analysis and data download. This database can be accessed through a web-based computational toolkit available at http://www.tpcn.pro/. By conducting meticulous manual searches and analyzing over 10 000 reference papers, the TPCN database has successfully integrated 6383 terpenoids obtained from 1254 distinct plant species. The database encompasses exhaustive details including isolation parts, comprehensive molecule structures, chemical abstracts service registry number (CAS number) and 7508 content descriptions. The TPCN database accentuates both the qualitative and quantitative dimensions as invaluable phenotypic characteristics of natural products that have undergone genetic evolution. By acting as an indispensable criterion, the TPCN database facilitates the discovery of drug alternatives with high content and the selection of high-yield medicinal plant species or phylogenetic alternatives, thereby fostering sustainable, cost-effective and environmentally friendly drug discovery in pharmaceutical farming. Database URL: http://www.tpcn.pro/., (© The Author(s) 2024. Published by Oxford University Press.)

The essential oil of Pelargonium graveolens (rose-scented geranium), an important aromatic plant, comprising mainly mono- and sesqui-terpenes, has applications in food and cosmetic industries. This study reports the characterization of isoprenyl disphosphate synthases (IDSs) involved in P. graveolens terpene biosynthesis. The six identified PgIDSs belonged to different classes of IDSs, comprising homomeric geranyl diphosphate synthases (GPPSs; PgGPPS1 and PgGPPS2), the large subunit of heteromeric GPPS or geranylgeranyl diphosphate synthases (GGPPSs; PgGGPPS), the small subunit of heteromeric GPPS (PgGPPS.SSUI and PgGPPS.SSUII), and farnesyl diphosphate synthases (FPPS; PgFPPS).All IDSs exhibited maximal expression in glandular trichomes (GTs), the site of aroma formation, and their expression except PgGPPS.SSUII was induced upon treatment with MeJA. Functional characterization of recombinant proteins revealed that PgGPPS1, PgGGPPS and PgFPPS were active enzymes producing GPP, GGPP/GPP, and FPP respectively, whereas both PgGPPS.SSUs and PgGPPS2 were inactive. Co-expression of PgGGPPS (that exhibited bifunctional G(G)PPS activity) with PgGPPS.SSUs in bacterial expression system showed lack of interaction between the two proteins, however, PgGGPPS interacted with a phylogenetically distant Antirrhinum majus GPPS.SSU. Further, transient expression of AmGPPS.SSU in P. graveolens leaf led to a significant increase in monoterpene levels. These findings provide insight into the types of IDSs and their role in providing precursors for different terpenoid components of P. graveolens essential oil., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Masson SAS. All rights reserved.)