Application and Evaluation of the Antifungal Activities of Glandular Trichome Secretions from Air/Sun-Cured Tobacco Germplasms against Botrytis cinerea.

The secretions of the glandular trichomes of tobacco leaves and flowers contain abundant secondary metabolites of different compounds, such as cebradanes, labdanes, and saccharide esters. These secondary metabolites have shown interesting biological properties, such as antimicrobial, insecticidal, and antioxidant activity. In this study, 81 air/sun-cured tobacco germplasms were used as experimental materials. Quantitative and qualitative analyses of the glandular secretion components were conducted using ultra-performance liquid chromatography-quadrupole-time of flight-mass spectrometry (UPLC-Q-TOF MS) and gas chromatography-mass spectrometry (GC-MS). The ethanol extracts of glandular trichomes from tobacco leaves and flowers were evaluated for antifungal activity against the fungus Botrytis cinerea using the mycelial growth rate method. Orthogonal Partial Least Squares (OPLS) analysis was then performed to determine the relationship between the trichome secretion components and their anti-fungal activity. The results showed significant differences among the antifungal activities of the tested ethanol extracts of tobacco glandular trichomes. The inhibition rates of the upper leaves and flower extracts against B. cinerea were significantly higher than those of the middle and lower leaves, and 59 germplasms (73.75% of the tested resources) showed antifungal rates higher than 50%, with four germplasms achieving a 95% antifungal rate at the same fresh weight concentration (10 mg/mL). The OPLS analysis revealed that the antifungal activity was primarily associated with alpha-cembratriene-diol (α-CBT-diol (Peak7)) and beta-cembratriene-diol (ß-CBT-diol (Peak8)), followed by sucrose esters III (SE(III)) and cembratriene-diol oxide. These findings help identify excellent tobacco germplasms for the development and utilization of botanical pesticides against fungi and provide a theoretical reference for the multipurpose utilization of tobacco germplasms.

Investigating the spatiotemporal expression of CBTS genes lead to the discovery of tobacco root as a cembranoid-producing organ.

Tobacco cembranoids, known for their anti-insect and antifungal properties, were shown to be mainly present on the surface of leaves and flowers, being biosynthesized by their trichomes. It remains unclear whether they could be biosynthesized in other organs without trichomes. Cembratrien-ol synthases (CBTSs) catalyze the conversion of GGPP to CBT-ols and thus play an important role in cembranoid biosynthesis. This study identified the CBTS family genes in tobacco and examined their spatiotemporal expression patterns. The CBTS genes showed diverse expression patterns in tobacco organs, with the majority highly expressed in leaves and a few highly expressed in flowers. The expression of CBTS genes were also correlated with the development of tobacco plants, and most of them showed the highest expression level at the budding stage. Furthermore, their expression is mediated by the JA (jasmonate) signaling in all tobacco organs. Several CBTS genes were found to be highly expressed in tobacco roots that have no trichomes, which prompted us to determine the cembranoid production in roots and other organs. GC-MS and UPLC assays revealed that cembranoids were produced in all tobacco organs, which was supported by the bioactivity assay results that almost all these CBTS enzymes could catalyze CBT-ol biosyntheis in yeast, and that the content ratio of CBT-ols and CBT-diols in tobacco roots was different to that in leaves. This work sheds insights into the expression profiles of tobacco CBTS genes and provides a feasibility to engineer tobacco roots for industrial production of cembranoids.

Chemical structures, biosynthesis, bioactivities, and utilisation values for the diterpenes produced in tobacco trichomes.

Cembranoids and labdanes are two important types of diterpenes in tobacco (Nicotiana genus) that are predominantly found in the leaf and flower glandular trichome secretions. This is the first systematic review of the biosynthesis, chemical structures, bioactivities, and utilisation values of cembranoid and labdane diterpenes in tobacco. A total of 131 natural cembranoid diterpenes have been reported in tobacco since 1962; these were summarised and classified according to their chemical structure characteristics as isopropyl cembranoids (1-88), seco-cembranoids (89-103), chain cembranoids (104-123), and polycyclic cembranoids (124-131). Forty natural labdane diterpenes reported since 1961 were also summarised and divided into epoxy side chain labdanes (132-150) and epoxy-free side chain labdanes (151-171). Tobacco cembranoid and labdane diterpenes are both formed via the methylerythritol 4-phosphate pathway and are synthesised from geranylgeranyl diphosphate. Their biosynthetic pathways and the four key enzymes (cembratrienol synthase, cytochrome P450 hydroxylase, copalyl diphosphate synthase, and Z-abienol cyclase) that affect their biosynthesis have been described in detail. A systematic summary of the bioactivity and utilisation values of the cembranoid and labdane diterpenes is also provided. The agricultural bioactivities associated with cembranoid and labdane diterpenes include antimicrobial and insecticidal activities as well as induced resistance, while the medical bioactivities include cytotoxic and neuroprotective activities. Further research into the cembranoid and labdane diterpenes will help to promote their development and utilisation as plant-derived pesticides and medicines.

Engineering eco-friendly and biodegradable biomass-based multifunctional antibacterial packaging films for sustainable food preservation.

The study presents a new class of eco-friendly and biodegradable biomass-based multifunctional antibacterial packaging films (G-OCSI) based on oxidized corn starch-based nonionic biopolymer (OCSI) and gelatin (Gel), and investigates the effects of different OCSI contents on the properties of G-OCSI. The results demonstrated that G-OCSI 0.25 had good water vapor barrier properties, antioxidant activity (DPPH RSA: 85.84 %), UV resistance (UV blocking > 99.9 %), water resistance (WCA: 122.30°), and tensile properties. Based on the disk diffusion experiment, G-OCSI exhibited significant bactericidal and antibacterial effects against S. aureus and E. coli. Moreover, G-OCSI had good biodegradability in natural environments, and could obviously accelerate the crops growth. Finally, a banana preservation experiment confirmed that G-OCSI could significantly extend the shelf life of bananas at room temperature at least 3 days. The biodegradable packaging films not only realizes the sustainable utilization of biomass resources but also has the potential to replace traditional petroleum-based plastics.

Roles and Preliminary Mechanism of Tobacco cis-Abienol in Inducing Tomato Resistance against Bacterial Wilt.

Bacterial wilt negatively impacts the yield and quality of tomatoes. cis-Abienol, a labdane diterpenoid abundantly produced in the trichome secretion of Nicotiana spp., can induce bacterial wilt resistance in plants; however, study on its practical application and acting mechanism is very limited. This study established the application conditions of cis-abienol for inducing tomato bacterial wilt resistance by pot-inoculation experiments and investigated the underlying mechanism by determining the physio-biochemical indexes and transcriptomic changes. The results showed that applying cis-abienol to the roots was the most effective approach for inducing tomato bacterial wilt resistance. The optimal concentration was 60 µg/mL, and 2-3 consecutive applications with 3-6 days intervals were sufficient to induce the bacterial wilt resistance of tomato plants. cis-Abienol could enhance the antioxidant enzyme activity and stimulate the defensive signal transduction in tomato roots, leading to the upregulation of genes involved in the mitogen-activated protein kinase cascade. It also upregulated the expression of JAZ genes and increased the content of jasmonic acid (JA) and salicylic acid (SA), which control the expression of flavonoid biosynthetic genes and the content of phytoalexins in tomato roots. cis-Abienol-induced resistance mainly depends on the JA signalling pathway, and the SA signalling pathway is also involved in this process. This study established the feasibility of applying the plant-derived terpenoid cis-abienol to induce plant bacterial wilt resistance, which is of great value for developing eco-friendly bactericides.

New indoleacetic acid-functionalized soluble oxidized starch-based nonionic biopolymers as natural antibacterial materials.

This study aims to develop a new soluble oxidized starch-based nonionic antibacterial polymer (OCSI) featuring high antibacterial activity and non-leachability by grafting indoleacetic acid monomer (IAA) onto the oxidized corn starch (OCS). The synthesized OCSI was characterized analytically by Nuclear magnetic resonance H-spectrometer (1H NMR), Fourier transform infrared spectroscopy (FTIR), Ultraviolet-visible spectroscopy (UV-Vis), X-ray diffractometer (XRD), X-ray Photoelectron Spectroscopy (XPS), Scanning Electronic Microscopy (SEM), Thermogravimetric Analysis (TGA) and Differential Scanning Calorimetry (DSC). The results showed that the synthesized OCSI was endowed with high thermal stability and favorable solubility, and the substitution degree reached 0.6. Besides, the disk diffusion test revealed a lowest OCSI inhibitory concentration of 5 µg disk-1, and showed significant bactericidal activity against Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli). Moreover, the antibacterial films (OCSI-PCL), featuring their good compatibility, mechanical properties, antibacterial activity, non-leachability, and low water vapor permeability (WVP), were also successfully prepared by blending OCSI with biodegradable polycaprolactone (PCL). Finally, CCK-8 assay results confirmed the excellent biocompatibility of the OCSI-PCL films. Overall, this very study evidenced the applicability of the obtained oxidized starch-based biopolymers as an eco-friendly non-ionic antibacterial material and confirmed their promising applications in areas including biomedical materials, medical devices, and food packaging.

Metabolomics and proteomics reveal the molecular basis of colour formation in the pericarp of Chinese wild rice (Zizania latifolia).

Chinese wild rice (Zizania latifolia) is rich in flavonoids and the characteristic colour of its pericarp is attributed to the flavonoids. In this study, the molecular basis of the colour change in the pericarp of Chinese wild rice was studied using metabolomics and proteomics. Whole seeds in three developmental stages (10, 20, and 30 days after flowering) were characterised based on phenolic contents, free amino acids (FAAs), and the expression level and activities of enzymes critical in flavonoid biosynthesis. The total phenolic and proanthocyanidin contents of Chinese wild rice increased gradually, whereas total flavonoid and FAA contents decreased during seed development. Metabolomic analysis revealed gradual upward trends for 57 flavonoids (sub classes 1, 3, and 10) related to colour change in the pericarp. Proteomic analysis showed that the phenylpropanoid biosynthesis metabolic pathway was enriched with differentially expressed proteins and was associated with flavonoid biosynthesis. Proteomic data suggested that leucoanthocyanidin reductase and WD40 repeat protein may be involved in flavonoid biosynthesis in Chinese wild rice, which was also verified by real-time quantitative PCR. Our results provide new insights into the understanding of the colour formation in the pericarp of Chinese wild rice.

Chromosome-level genome assembly of Zizania latifolia provides insights into its seed shattering and phytocassane biosynthesis.

Chinese wild rice (Zizania latifolia; family: Gramineae) is a valuable medicinal homologous grain in East and Southeast Asia. Here, using Nanopore sequencing and Hi-C scaffolding, we generated a 547.38 Mb chromosome-level genome assembly comprising 332 contigs and 164 scaffolds (contig N50 = 4.48 Mb; scaffold N50 = 32.79 Mb). The genome harbors 38,852 genes, with 52.89% of the genome comprising repetitive sequences. Phylogenetic analyses revealed close relation of Z. latifolia to Leersia perrieri and Oryza species, with a divergence time of 19.7-31.0 million years. Collinearity and transcriptome analyses revealed candidate genes related to seed shattering, providing basic information on abscission layer formation and degradation in Z. latifolia. Moreover, two genomic blocks in the Z. latifolia genome showed good synteny with the rice phytocassane biosynthetic gene cluster. The updated genome will support future studies on the genetic improvement of Chinese wild rice and comparative analyses between Z. latifolia and other plants.

NtMYB305a binds to the jasmonate-responsive GAG region of NtPMT1a promoter to regulate nicotine biosynthesis.

MYB transcription factors play essential roles in regulating plant secondary metabolism and jasmonate (JA) signaling. Putrescine N-methyltransferase is a key JA-regulated step in the biosynthesis of nicotine, an alkaloidal compound highly accumulated in Nicotiana spp. Here we report the identification of NtMYB305a in tobacco (Nicotiana tabacum) as a regulatory component of nicotine biosynthesis and demonstrate that it binds to the JA-responsive GAG region, which comprises a G-box, an AT-rich motif, and a GCC-box-like element, in the NtPMT1a promoter. Yeast one-hybrid analysis, electrophoretic mobility shift assay and chromatin immunoprecipitation assays showed that NtMYB305a binds to the GAG region in vitro and in vivo. Binding specifically occurs at the ∼30-bp AT-rich motif in a G/C-base-independent manner, thus defining the AT-rich motif as previously unknown MYB-binding element. NtMYB305a localized in the nucleus of tobacco cells where it is capable of activating the expression of a 4×GAG-driven GUS reporter in an AT-rich motif-dependent manner. NtMYB305a positively regulates nicotine biosynthesis and the expression of NtPMT and other nicotine pathway genes. NtMYB305a acts synergistically with NtMYC2a to regulate nicotine biosynthesis, but no interaction between these two proteins was detected. This identification of NtMYB305a provides insights into the regulation of nicotine biosynthesis and extends the roles played by MYB transcription factors in plant secondary metabolism.

Synthesis of cembratriene-ol and cembratriene-diol in yeast via the MVA pathway.

BACKGROUND: Cembranoids are one kind of diterpenoids with multiple biological activities. The tobacco cembratriene-ol (CBT-ol) and cembratriene-diol (CBT-diol) have high anti-insect and anti-fungal activities, which is attracting great attentions for their potential usage in sustainable agriculture. Cembranoids were supposed to be formed through the 2-C-methyl-D-erythritol-4-phosphate (MEP) pathway, yet the involvement of mevalonate (MVA) pathway in their synthesis remains unclear. Exploring the roles of MVA pathway in cembranoid synthesis could contribute not only to the technical approach but also to the molecular mechanism for cembranoid biosynthesis. RESULTS: We constructed vectors to express cembratriene-ol synthase (CBTS1) and its fusion protein (AD-CBTS1) containing an N-terminal GAL4 AD domain as a translation leader in yeast. Eventually, the modified enzyme AD-CBTS1 was successfully expressed, which further resulted in the production of CBT-ol in the yeast strain BY-T20 with enhanced MVA pathway for geranylgeranyl diphosphate (GGPP) production but not in other yeast strains with low GGPP supply. Subsequently, CBT-diol was also synthesized by co-expression of the modified enzyme AD-CBTS1 and BD-CYP450 in the yeast strain BY-T20. CONCLUSIONS: We demonstrated that yeast is insensitive to the tobacco anti-fungal compound CBT-ol or CBT-diol and could be applied to their biosynthesis. This study further established a feasibility for cembranoid production via the MVA pathway and provided an alternative bio-approach for cembranoid biosynthesis in microbes.

Comparison of the contents of phenolic compounds including flavonoids and antioxidant activity of rice (Oryza sativa) and Chinese wild rice (Zizania latifolia).

The contents of phenolic compounds, especially flavonoids, and antioxidant activity of rice (Oryza sativa, Os) and Chinese wild rice (Zizania latifolia, Zl) harvested in China were compared. Zl possessed significantly higher contents of total phenolics, flavonoids, and proanthocyanidins and exhibited higher antioxidant activity than in the Os Xian group, the Os Geng group, and red rice. The flavonoid contents of Os and Zl were compared using a UHPLC-QqQ-MS-based metabolomics approach. A total of 159 flavonoids were identified, among which 78 showed differential expression (72 up-regulated and six down-regulated in the Zl group). The Kyoto Encyclopaedia of Genes and Genomes annotation and classification indicated that the differentially expressed flavonoids were mainly related to anthocyanin biosynthesis. Moreover, candidate genes for flavonoid biosynthesis in Os and Zl were identified in this study. Compared with non-pigmented and red rice, Zl may be more nutritious and is thus considered a better source of natural antioxidants.

Consumption of Wild Rice (Zizania latifolia) Prevents Metabolic Associated Fatty Liver Disease through the Modulation of the Gut Microbiota in Mice Model.

Metabolic associated fatty liver disease (MAFLD) due to excess weight and obesity threatens public health worldwide. Gut microbiota dysbiosis contributes to obesity and related diseases. The cholesterol-lowering, anti-inflammatory, and antioxidant effects of wild rice have been reported in several studies; however, whether it has beneficial effects on the gut microbiota is unknown. Here, we show that wild rice reduces body weight, liver steatosis, and low-grade inflammation, and improves insulin resistance in high-fat diet (HFD)-fed mice. High-throughput 16S rRNA pyrosequencing demonstrated that wild rice treatment significantly changed the gut microbiota composition in mice fed an HFD. The richness and diversity of the gut microbiota were notably decreased upon wild rice consumption. Compared with a normal chow diet (NCD), HFD feeding altered 117 operational taxonomic units (OTUs), and wild rice supplementation reversed 90 OTUs to the configuration in the NCD group. Overall, our results suggest that wild rice may be used as a probiotic agent to reverse HFD-induced MAFLD through the modulation of the gut microbiota.

Wild rice (Zizania spp.): A review of its nutritional constituents, phytochemicals, antioxidant activities, and health-promoting effects.

Wild rice (Zizania spp.), an important aquatic cereal grain in North America and East Asia, has attracted interest worldwide because of its antioxidant activities and health-promoting effects. Wild rice is high in protein, minerals, and vitamins but is low in fat. The phytochemical content (phytosterols, γ-oryzanol, γ-aminobutyric acid, phenolic acids, and flavonoids) of wild rice warrants its development as a functional food. Phenolic acids, flavonoids, and other phytochemicals from Zizania plants have pronounced antioxidant properties, which are associated with prevention of chronic diseases. The health-promoting effects of Zizania plants include alleviation of insulin resistance and lipotoxicity, atherosclerosis prevention, and anti-inflammatory, anti-allergic, anti-hypertensive, and immunomodulatory effects. Here, we provide an overview of Zizania research up to April 2020, focusing on the nutritional constituents, phytochemicals, antioxidant activities, and health-promoting effects of Zizania plants. This review has important implications for further investigations and applications of Zizania plants in medicine and as functional foods.

Effects of NtSPS1 Overexpression on Solanesol Content, Plant Growth, Photosynthesis, and Metabolome of Nicotiana tabacum.

Nicotiana tabacum solanesyl diphosphate synthase 1 (NtSPS1) is the key enzyme in solanesol biosynthesis. However, changes in the solanesol content, plant growth, photosynthesis, and metabolome of tobacco plants after NtSPS1 overexpression (OE) have not been previously reported. In the present study, these parameters, as well as photosynthetic gas exchange, chlorophyll content, and chlorophyll fluorescence parameters, were compared between NtSPS1 OE and wild type (WT) lines of tobacco. As expected, NtSPS1 OE significantly increased solanesol content in tobacco leaves. Although NtSPS1 OE significantly increased leaf growth, photosynthesis, and chlorophyll content, the chlorophyll fluorescence parameters in the leaves of the NtSPS1 OE lines were only slightly higher than those in the WT leaves. Furthermore, NtSPS1 OE resulted in 64 differential metabolites, including 30 up-regulated and 34 down-regulated metabolites, between the OE and WT leaves. Pathway enrichment analysis of these differential metabolites identified differentially enriched pathways between the OE and WT leaves, e.g., carbon fixation in photosynthetic organisms. The maximum carboxylation rate of RuBisCO and the maximum rate of RuBP regeneration were also elevated in the NtSPS1 OE line. To our knowledge, this is the first study to confirm the role of NtSPS1 in solanesol biosynthesis and its possible functional mechanisms in tobacco.

Characterization of Nuclear and Mitochondrial Genomes of Two Tobacco Endophytic Fungi Leptosphaerulina chartarum and Curvularia trifolii and Their Contributions to Phylogenetic Implications in the Pleosporales.

The symbiont endophytic fungi in tobacco are highly diverse and difficult to classify. Here, we sequenced the genomes of Curvularia trifolii and Leptosphaerulina chartarum isolated from tobacco plants. Finally, 41.68 Mb and 37.95 Mb nuclear genomes were sequenced for C. trifolii and L. chartarum with the scaffold N50, accounting for 638.94 Kb and 284.12 Kb, respectively. Meanwhile, we obtained 68,926 bp and 59,100 bp for their mitochondrial genomes. To more accurately classify C. trifolii and L. chartarum, we extracted seven nuclear genes and 12 mitochondrial genes from these two genomes and their closely related species. The genes were then used for calculation of evolutionary rates and for phylogenetic analysis. Results showed that it was difficult to achieve consistent results using a single gene due to their different evolutionary rates, while the phylogenetic trees obtained by combining datasets showed stable topologies. It is, therefore, more accurate to construct phylogenetic relationships for endophytic fungi based on multi-gene datasets. This study provides new insights into the distribution and characteristics of endophytic fungi in tobacco.

Dynamics of antioxidant activities, metabolites, phenolic acids, flavonoids, and phenolic biosynthetic genes in germinating Chinese wild rice (Zizania latifolia).

In this study, the antioxidant activity of germinating Chinese wild rice was found to decline initially, after which it increased. The largest difference in antioxidant activity was observed between the 36-h (G36) and the 120-h germination (G120) stage. We further assessed the dynamic changes in metabolites, phenolic acids, flavonoids, and phenolic biosynthetic genes in germinating Chinese wild rice. Ultra-high performance liquid chromatography-triple quadrupole mass spectrometry revealed that 315 metabolites were up-regulated and 28 were down-regulated between G36 and G120. Levels of p-hydroxybenzoic acid, p-hydroxybenzaldehyde, vanillin, p-coumaric acid, ferulic acid, and epigallocatechin increased significantly during germination. Gene expression of four phenylalanine ammonia-lyases, one 4-coumarate-CoA ligase, one cinnamoyl-CoA reductase, two cinnamyl alcohol dehydrogenases, one chalcone synthase, and one chalcone isomerase was significantly higher at G120 than at G36 and promoted phenolics accumulation. This study elucidated the biochemical mechanisms involved in antioxidant activity and phenolic profile changes during Chinese wild rice germination.

Angularly Prenylated Indole Alkaloids with Antimicrobial and Insecticidal Activities from an Endophytic Fungus Fusarium sambucinum TE-6L.

Bioactivity-guided isolation of the endophytic fungus Fusarium sambucinum TE-6L residing in Nicotiana tabacum L. led to the discovery of two new angularly prenylated indole alkaloids (PIAs) with pyrano[2,3-g]indole moieties, amoenamide C (1) and sclerotiamide B (2), and four known biosynthetic congeners (3-6). Their structures were determined by comprehensive spectroscopic techniques, electronic circular dichroism (ECD), and X-ray diffraction. Compound 1 containing the bicyclo[2.2.2]diazaoctane core and indoxyl unit is rarely reported. All the compounds were evaluated for their antimicrobial and insecticidal activities. Notably, compounds 1-3 showed potent inhibitory effects against three human- and one plant-pathogenic bacterium, and seven plant-pathogenic fungi. Compounds 2-4 also exhibited remarkable larvicidal activity against first instar larvae of the cotton bollworm Helicoverpa armigera with mortality rates of 70.2%, 83.2%, and 70.5%, respectively. Further toxicity tests on zebrafish embryos were performed to evaluate the potential toxicity of PIAs. Of significance was that compound 3 in particular exhibited the highest activities but the lowest effects on the hatching of embryos among all the compounds. This study provides a basis for understanding developmental toxicity of PIAs exposure to zebrafish embryos, and also indicates the potential environmental risks of other natural compounds exposure in the aquatic ecosystem.

Rh-Catalyzed Regioselective Dialkylation of Cage B-H bonds in o-Carboranes: Oxidative Heck Reactions via an Enol Isomerization.

In the presence of a carboxylic acid directing group, Rh-catalyzed regioselective directed dialkylation of B(4,5)-H bonds in o-carboranes and oxidative coupling with allylic alcohols is reported. This strategy constructs a series of 4,5-dialkylated o-carboranes in good yields with excellent regioselectivity. A possible catalytic cycle is proposed that involves a tandem sequence of Rh-catalyzed cage B-H activation, alkene insertion, selective ß-H elimination, enol isomerization, and decarboxylation.

Bioactivities and Medicinal Value of Solanesol and Its Accumulation, Extraction Technology, and Determination Methods.

Solanesol, an aliphatic terpene alcohol composed of nine isoprene units, is mainly found in solanaceous plants. Particularly, tobacco (Nicotiana tabacum), belonging to the Solanaceae family, is the richest plant source of solanesol, and its leaves have been regarded as the ideal material for solanesol extraction. Since the discovery of solanesol in tobacco, significant progress has been achieved in research on solanesol's bioactivities, medicinal value, accumulation, extraction technology, and determination methods. Solanesol possesses strong free radical absorption ability and antioxidant activity owing to the presence of several non-conjugated double bonds. Notably, solanesol's anti-inflammatory, neuroprotective, and antimicrobial activities have been previously demonstrated. Solanesol is a key intermediate in the synthesis of coenzyme Q10, vitamin K2, and the anticancer agent synergiser N-solanesyl-N,N'-bis(3,4-dimethoxybenzyl) ethylenediamine. Other applications of solanesol include solanesol derivative micelles for hydrophobic drug delivery, solanesol-derived scaffolds for bioactive peptide multimerization, and solanesol-anchored DNA for mediating vesicle fusion. Solanesol accumulation in plants is influenced by genetic and environmental factors, including biotic stresses caused by pathogen infections, temperature, illumination, and agronomic measures. Seven extraction technologies and seven determination methods of solanesol are also systematically summarized in the present review. This review can serve as a reference for solanesol's comprehensive application.

Transition-metal-free direct nucleophilic substitution of carboranyllithium and 2-halopyridines.

A practical and efficient C(cage)-heteroarylation of carborane is presented, via direct nucleophilic substitution of carboranyllithium with 2-halopyridines. This reaction does not need the aid of any transition metal and utilizes readily available carboranyllithium nucleophiles, thereby avoiding transmetalation of carboranyllithium. The process exhibits a broad scope, and a vast array of 2-halopyridines have proven to be suitable substrates. The method serves as a complement to C(cage)-arylation reactions and may find wide applications in materials science and medicinal and coordination chemistry.