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Ginkgo seeds can serve as not only food but also drugs, which benefit from their plenty of nutritional and functional components. However, the presence of 4'-O-methylpyridoxine (MPN) and its 5'-glucoside (MPNG), known as ginkgotoxin, prohibits people from daily consumption of Ginkgo seeds. People have traditionally believed that removing the plantule or heating Ginkgo seeds will detoxify them and that storing them at low temperatures will reduce the ginkgotoxin through their metabolism. This work aimed to confirm or falsify these traditional understandings. The results showed that the highest content of ginkgotoxin in plantule reached 2246.99 ± 8.19 µg/g. However, removing the plantule can only slightly reduce the toxicity of Ginkgo seeds, because the weight of plantule only accounts for about 1% of Ginkgo seeds. Storage with shells (-20 ℃) was determined to be the optimal storage method for Ginkgo seeds, however, which only led to 12.57% decrease in ginkgotoxin. Boiling treatment was effective in reducing the toxicity by dissolving ginkgotoxin from Ginkgo seeds to water. The content of TMPN (MPN and MPNG) decreased from 534.36 ± 12.99 µg/g to 331.83 ± 5.53 µg/g. Whereas frying, microwaving, and baking had little influence on the content of ginkgotoxin in the case of guaranteeing the edibility of Ginkgo seeds. Interestingly, the conversion of MPNG to MPN was largely reduced by storing under low temperatures and heating treatment, which can reduce the toxicity of Ginkgo seeds because MPNG was much less toxic than MPN. These results involving ginkgotoxin furnish information for safe utilization of Ginkgo seeds. [ABSTRACT FROM AUTHOR]

Ginkgo biloba seed (GBS) contains rich nutrients, such as starch, protein, oil, and trace components, such as flavonoids and terpene lactones. Due to its high protein content, it can be used as a raw material for fermentation and brewing. In this study, GBS was selected as the object of a fermentation process optimization test. Six kinds of fermentation starter were selected to brew ginkgo wine. The results showed that different fermentation starters have significant impacts on the composition of the wine. The yeast group had higher total sugar content and comprehensive evaluation scores than the Jiuqu group, while the total acid and total free amino acid contents showed the opposite result. The total flavonoid and total terpene lactone contents of the yeast group were 21.0% and 12.8% higher than those of the Jiuqu group, respectively. However, the 4′-O-methylpyridoxine (MPN) and 4′-O-methylpyridoxine-5′-glucoside (MPNG) contents of the yeast group were also 12.6% and 2.3% higher than those of the Jiuqu group, respectively. The common volatile components in the two groups of samples were isoamyl alcohol, phenethyl alcohol, ethyl octanoate, and phenethyl acetate. The antioxidant capacity of ginkgo wine fermented by yeast was significantly higher than that of the Jiuqu group sample. [ABSTRACT FROM AUTHOR]

There are some differences in the anti-inflammatory activities of four typical components in EGB (extracts of ginkgo biloba leaves), and there is also a synergistic relationship. The order of inhibiting the NO-release ability of single functional components is OA > GF > OPC > G. Ginkgolide (G), proanthocyanidins (OPC), and organic acids (OA) all have synergistic effects on ginkgo flavonoids (GF). GF:OA (1:9) is the lowest interaction index among all complexes, showing the strongest synergy. The anti-inflammatory mechanism of the compound affects the expression of p-JNK, p-P38, and p-ERK1/2 proteins by inhibiting the expression of iNOS and COX2 genes on NFKB and MAPK pathways. This also provides a research basis for the development of anti-inflammatory deep-processing products of EGB. [ABSTRACT FROM AUTHOR]

Ginkgo biloba L. is an ancient plant relic, which is known as a "living fossil", and is widely cultivated in China. This plant with medical potential and health benefits has drawn the attention of researchers. Ginkgo seeds are rich in protein. Ginkgo seed proteins (GSPs) have good functional properties over many other seed proteins, which have the potential to be utilized as food ingredients. Moreover, GSP contains no restricted amino acids and is easy to be separated. Several GSP isolate with various bioactivities, such as antimicrobial and antioxidative activities, have been purified and evaluated for their bioactive potential. In this review, the separation methods and bioactivities of GSP were summarized, physicochemical characteristics and functional properties were comprehensively reviewed and compared with other seed proteins. Some food applications of GSP were also briefly introduced. Besides, some suggestions and prospects were discussed in this review. [ABSTRACT FROM AUTHOR]

BACKGROUND Ginkgo biloba seeds are well known for the significant curative effects on relieving cough and asthma. However, the development of products from ginkgo seeds still falls behind at present, resulting in a great waste of ginkgo seeds' resource. In this work, submerged fermentation of ginkgo seed powder using Eurotium cristatum was studied to investigate its feasibility as a new processing method. RESULTS: To promote the growth of E. cristatum, the optimum fermentation medium was 80.0 g L−1 of ginkgo seed powder with addition of 5.0 g L−1 calcium chloride (CaCl2), 4.0 g L−1 magnesium sulfate (MgSO4), 1.25 g L−1 zinc sulfate (ZnSO4) and 0.65 g L−1 iron(II) sulfate (FeSO4). The optimum fermentation conditions were pH 5.8 ± 0.1, inoculum size 5.1 × 106 CFU mL−1, liquid medium volume 100 mL in 250‐mL Erlenmeyer flask and fermentation 4 days. Through fermentation, the production of lovastatin in fermentation broth could reach up to 32.97 ± 0.17 μg mL−1 and the total antioxidant capacity was improved by more than two‐fold. In addition, 40.15% of the ginkgotoxin in ginkgo seed powder was degraded while the entire degradation of ginkgolic acids was obtained. Moreover, fermented ginkgo seed powder suspension presented pleasant fragrances, and the activities of amylase and protease were enhanced to 11.30 ± 0.10 U mL−1 and 23.01 ± 0.20 U mL−1, respectively. CONCLUSIONS: Submerged fermentation using E. cristatum could significantly enhance the functional value and safety of ginkgo seed powder, and had great potential to become a novel processing method for the development of ginkgo seeds fermented products. © 2020 Society of Chemical Industry [ABSTRACT FROM AUTHOR]

BACKGROUND Ginkgotoxin including 4′‐O‐methylpyridoxine (MPN) and MPN‐5′‐glucoside (MPNG) is responsible for Ginkgo seed food poisoning. The purpose of the work reported was to prepare detoxified Ginkgo seed powder and at the same time to retain the nutritional and functional components of Ginkgo seed powder to the maximum extent. RESULTS: Resin adsorption technology was firstly employed to remove ginkgotoxin from water extract of Ginkgo seed powder. Under optimal conditions, the adsorption efficiency of the optimal resin for MPN could reach 100%, and that for MPNG could only reach 85.4 ± 0.93%. Resin adsorption alone could not effectively remove MPN and MPNG simultaneously. Endogenous enzymatic hydrolysis was next attempted to transform MPNG to MPN. MPNG could be completely hydrolyzed to MPN by endogenous enzyme(s) at 40 °C and pH 5.0 in 180 min. Ginkgotoxin only in the form of MPN in the enzymatic hydrolysate was then adsorbed with resin and the conditions were statistically optimized. The adsorption efficiency of MPN reached 98.89 ± 0.99% under the optimized conditions. CONCLUSIONS: Removal of ginkgotoxin by combining endogenous enzymatic hydrolysis with resin adsorption could preserve the main nutritional and functional components of Ginkgo seed powder to the most extent, and did not change its main characteristics. The ginkgotoxin removal method developed in this work is a relatively simple and efficient approach. © 2020 Society of Chemical Industry [ABSTRACT FROM AUTHOR]

Two-phase systems developed with hydrophilic deep eutectic solvents (DESs) and hydrophobic DESs were prepared in this study for the first time. Ginkgo biloba leaves containing several bioactive compounds were chosen as the model plant material to evaluate the possibility of the two-phase DES system as a designer solvent for the simultaneous extraction of the various bioactive compounds with different polarities. After tailoring, a two-phase DES system prepared with two hydrophilic DESs and one hydrophobic DES at a volume ratio of 35 : 5 : 40 could effectively extract flavonoids, terpene trilactones (TTLs), procyanidine (PAC) and polyprenyl acetates (PPAs) simultaneously from the Ginkgo biloba leaves. The extraction conditions were further optimized using the response surface methodology. When the two-phase DES system was employed in the extraction under the optimal conditions, the PPAs moved into the hydrophobic phase, and the flavonoids, TTLs, and PAC were enriched into the hydrophilic phase. The first extraction rates for PAC, flavonoids, TTLs and PPAs were 86.07%, 77.72%, 93.29% and 94.63%, respectively. After extraction, the hydrophilic and hydrophobic phases containing different bioactive compounds could be easily separated for different preparations. Extraction with the two-phase DES system is a new application trial of DESs, which has the potential to be widely used for the extraction of bioactive compounds from plant materials or removal of different polar impurities from specific extracts. [ABSTRACT FROM AUTHOR]

Deep eutectic solvents (DESs)-based ultrasonic extraction of terpene trilactones (TTLs) fromGinkgo bilobaleaves was efficiently developed. Sixteen DESs were prepared, and DESs composed of choline chloride-urea (ChCl-U) and betaine-ethylene glycol (BE-EG) gave higher TTL extraction yields than the present, most efficient solvent 70% ethanol. The extraction conditions were further optimized, and the optimum conditions were as follows: taking BE-EG containing 40% (w/w) water as the extraction solvent, 1:10 ofG. bilobaleaves powder-to-solvent ratio, and ultrasonic treatment at 45°C and 100 W for 20 min. A total extraction yield of 1.94 ± 0.03 mg/g was obtained under the optimum conditions, which indicated that 99.37% of TTLs could be extracted from theG. bilobaleaves powder by a single extraction. Moreover, the polyamide resin was used to recover the TTLs in DES extracting solution, and recovery yield of 95.1% was attained. Therefore, BE-EG containing 40% (w/w) water was a potential alternative solvent for TTLs extraction fromG. bilobaleaves. [ABSTRACT FROM AUTHOR]

The predicted anti-oxidation is related to apoptosis, proliferation, lipid metabolism, cell differentiation, and immune response. There are some differences in the antioxidant capacity of the four typical components of ginkgo biloba extract (EGb) including ginkgo flavone (GF), ginkgolide (G), procyanidins (OPC), and organic acids (OA), and any two members of them can exhibit apparent synergistic effects. The order of DPPH scavenging ability was: OPC > GF > OA > G. The scavenging ability of procyanidins was close to that of VC; the scavenging capacity of ABTS was GF > OPC > OA > G. The GF:OPC (1:9) showed the best synergism in scavenging DPPH and ABTS radicals. The 193 kinds of small molecules reported in EGb were obtained by analyzing the properties of EGb. In order to construct a corresponding biological activity target set, molecular docking and the network pharmacology method were employed to build the molecular action mechanism network of a compound target, and the main biological functions and signaling pathways involved with their antioxidant activities were predicted. The results displayed that the top ten compounds which belonged to the two broad categories, ginkgo flavonoids and proanthocyanidins, could interact closely with several important target proteins (CASP3, SOD2, MAPK1, HSPA4, and NQO1). This would be expected to lay a theoretical foundation for the deep development of Ginkgo biloba extract. [ABSTRACT FROM AUTHOR]

Ginkgo biloba leaves are well known for their high content of nutrients and bioactive substances. However, unpleasant smell and a small number of ginkgolic acids greatly reduce the utilization of the leaves. In this work, solid-state fermentation of G. biloba leaves using Eurotium cristatum was studied by investigation of the nutrient changes and its feasibility as a functional feed. E. cristatum could grow on pure G. biloba leaves and the addition of excipients could significantly improve the growth of E. cristatum. The optimal medium was with 10% (w/w) of whole G. biloba seeds and the optimized water content, pH, inoculum size and fermentation time were 45% (w/w), 4.5, 4.76 × 107 CFU/100 g wet medium, and eight days, respectively. Under the optimal conditions, the spore number increased by about 40 times. The content of flavonoids was greatly increased by 118.6%, and the protein and polyprenyl acetates (PPAs) were increased by 64.9% and 10.6%, respectively. The ginkgolic acids, lignin, and cellulose were decreased by 52.4%, 38.5%, and 20.1% than before, respectively. Furthermore, the fermented G. biloba leaves showed higher antioxidant activity and held more aroma substances. Thus, G. biloba leaves fermented by E. cristatum have potential as s high value-added feed. This is the first investigation of E. cristatum fermentation on ginkgo leaves, which will facilitate the use of ginkgo leaves in the feed industry. [ABSTRACT FROM AUTHOR]

Ginkgo biloba leaves have various health benefits due to the presence of bioactive compounds such as polyprenyl acetates, flavonoids, and terpene trilactones. However, there is little literature reported on the aromatic acids in Ginkgo biloba leaves. In this work, five aromatic acids including shikimic acid (SA), 6-hydroxykynurenic acid (6-HKA), protocatechuic acid (PA), gallic acid (GAA), and p-hydroxybenzoic acid (PHBA) were simultaneously extracted from Ginkgo biloba leaves by employing the green deep eutectic solvents (DESs). A DES tailor-made from xylitol, glycolic acid and 1,5-pentanedioic acid at a molar ratio of 1:3:1 with 50% (w/w) water addition, named as NGG50, gave higher extraction yields for the five aromatic acids. Main factors affecting the extraction process were further optimized. The highest extraction yields of SA, GAA, 6-HKA, PA, and PHBA were 94.15 ± 0.96 mg/g, 332.69 ± 5.19 μg/g, 25.90 ± 0.61 μg/g, 429.89 ± 11.47 μg/g and 67.94 ± 0.37 μg/g, respectively. The NGG50-based extraction process developed here was a successful attempt of simultaneously extracting five aromatic acids from Ginkgo biloba leaves for the first time, which could provide a new exploitation direction of Ginkgo biloba leaves. [ABSTRACT FROM AUTHOR]

Ginkgo seeds are rich in nutrients and bioactive compounds, but they cause poisoning after excessive consumption, thus limiting their application. In this work, enzymatic degradation technology was employed to remove ginkgotoxins presented in ginkgo seeds, including 4'-O-methylpyridoxine (MPN) and MPN-5'-glucoside (MPNG). Through the screening of four oxidases and ten reaction mediators, the laccase-syringaldehyde system was successfully established. After optimizing the reaction conditions using response surface methodology (RSM), ginkgotoxins in both raw and boiled ginkgo seed powder was completely degraded at a temperature of 40 °C and a solvent to solid ratio (60 mL/g) of the ginkgo seed powder suspension within 3 h. Furthermore, the main nutritional components of detoxified ginkgo seed powder did not exhibit significant changes, but there was inevitably a decrease in the content of bioactive compounds. Finally, an acute oral toxicity assessment demonstrated that the detoxified ginkgo seed powder was virtually non-toxic. Therefore, enzymatic degradation using the laccase-syringaldehyde system has the potential to be a simple and effective approach for removing ginkgotoxins from ginkgo seed powder, thereby meeting the safety requirements for ginkgo products. [Display omitted] • A laccase-syringaldehyde system was established to degrade ginkgotoxins. • Both MPNG and MPN were completely degraded under the optimal enzymatic degradation conditions. • All ginkgotoxins present in both raw and boiled ginkgo seed powder could be effectively degraded. • Detoxified ginkgo seed powder prepared was proven to be non-toxic by an acute oral toxicity test. • The enzymatic removal technology is simple, efficient and suitable for the industrial use. [ABSTRACT FROM AUTHOR]

This study aimed to screen microorganisms capable of removing ginkgolic acids (GAs) from Ginkgo biloba leaf. Given the presence of long alkyl side chains in GAs, the study first focused on screening microorganisms that could utilize long-chain alkanes (n-tridecane, n-pentadecane, and n-heptadecane) and further studying their GAs degradation abilities. The results showed that the degradation rates of GAs by the two bacteria strains (identified as Pantoea sp.) were about 50 %, and the degradation rates of GAs by the nine fungal strains (identified as Fusarium sp.) were about 95 %. Meanwhile, Lactiplantibacillus plantarum was also found to exhibit a robust capacity for degrading GAs. Through further optimization of the medium components and fermentation conditions, Lactiplantibacillus plantarum achieved a degradation rate of 81.581 % for total GAs after 72 hours of cultivation. Notably, this process did not significantly impact flavonoids and terpene lactones present in Ginkgo biloba extract (EGb), which are essential for its therapeutic properties. Additionally, the results demonstrated that the hydrophobicity of GAs significantly influenced the degradation efficiency of GAs by Lactiplantibacillus plantarum. This study highlights the potential industrial application value of Lactiplantibacillus plantarum in the production of ginkgo products with low GAs content, thereby enhancing the safety and efficacy of this widely used medicinal plant. • Two strains of bacteria and nine strains of fungi screened from the soil could degrade GAs. • Lactiplantibacillus plantarum commonly used in food industry has good ability to degrade GAs. • Lactiplantibacillus plantarum has no significant effect on flavonoids and other active ingredients in EGb. • The structure of GAs had great influence on the degradation effect of GAs by Lactiplantibacillus plantarum. [ABSTRACT FROM AUTHOR]

Ginkgo biloba L. seeds are used for food and medicinal purposes in China, but excessive consumption of them can cause acute toxicity. Ginkgotoxin (MPN) and its-5'-glucoside (MPNG) are the main toxic substances in ginkgo seeds. Ginkgo biloba L. trees are widely cultivated in China, and there are fewer studies on total ginkgotoxin (TMPN, MPN and MPNG) in ginkgo from different regions, which is the main motivation for this work. We determined the levels of TMPN in ginkgo seed samples from different regions of China (24.44–41.19 °N, 98.68–124.43 °E), which ranged from 140.96 ± 4.19 μg/g to 537.14 ± 10.78 μg/g. We found that all 131 ginkgo seed samples contained TMPN. Pearson's correlation was performed to analyze the correlation between the TMPN, tree age, geographical location, and climatic factors. The study showed that for geographical factors, longitude was significantly positively correlated with TMPN, and altitude was significantly negatively correlated with TMPN. Regarding climatic factors, mean annual temperature (MAT) and mean warmest month temperature (MWMT) were significantly and positively correlated with TMPN. Our results contribute to a better understanding of the distribution of TMPN in ginkgo seeds in China and lay a scientific foundation for improving low toxicity and safe ginkgo food ingredients. [Display omitted] • Each Ginkgo biloba seed sample contained a certain amount of total ginkgotoxin (TMPN). • Longitude was significantly and positively correlated with TMPN. • Altitude was significantly and negatively correlated with TMPN. • The mean annual temperature and the mean warmest month temperature were both significantly and positively correlated with TMPN. [ABSTRACT FROM AUTHOR]

Ginkgo biloba seeds contain a variety of nutritional and functional components and have high edible and medicinal effects, making them one of the famous food and medicine homologous materials. But G. biloba seeds also contain some harmful ingredients, which have severely restricted the healthy development of the G. biloba seed food industry. Overconsumption of G. biloba seeds can lead to food poisoning. Ginkgotoxin (4′-O-methylpyridoxine, MPN) and ginkgotoxin-5′-glucoside (4′-O-methylpyridoxine-5′-glucoside, MPNG) are the main toxic ingredients of G. biloba seeds and have been studied intensively. This work tries to comprehensively summarize the research status of MPN and MPNG (collectively known as ginkgotoxins), building the scientific basis for further research on ginkgotoxins, with the aspiration to promote the healthy development of the G. biloba seed food industry. In this review, the isolation, identification, extraction, and detection of ginkgotoxins are first introduced. Then, the synthesis and distribution of ginkgotoxins are described and discussed. Finally, the methods used for removing ginkgotoxins and the effects of processing on the ginkgotoxins are analyzed and compared. Reducing ginkgotoxins while preserving the nutritional and functional components of G. biloba seed foods will undoubtedly be a pressing issue in further research. [Display omitted] • Ginkgo biloba seeds contain a variety of nutritional and functional components. • Overconsumption of Ginkgo biloba seeds leads to poisoning. • Ginkgotoxin and ginkgotoxin-5′-glucoside is responsible for Ginkgo biloba seeds poisoning. • MPN and MPNG can be completely removed by some physical and biotechnological methods. • Food processing techniques can only reduce toxicity to a limited extent. [ABSTRACT FROM AUTHOR]

Proanthocyanidin (PAC) holds strong free radicals scavenging ability and is widely used as oxygen free radical scavenger. Huge demand, safety and economic aspect are forcing the PAC extraction to explore new resource and greener solvent. An efficient extraction method of PAC from Ginkgo biloba leaves was established by employing deep eutectic solvent (DES)-water mixture. After a rational design, a DES-water mixture (named as Ch-M 55 ) was chosen as the extraction solvent, which was prepared from choline chloride and malonic acid at a molar ratio of 1:2 with water addition of 55% (w/w). The main factors affecting the extraction yield were statistically optimized using a central composite design combined with response surface methodology (RSM). The optimal conditions were obtained as follows: extraction temperature of 65 °C, extraction time of 53 min and Ch-M 55 to solid ratio of 10.57:1 (v/w, mL/g). The PAC extraction yield was 22.19 ± 0.71 mg/g under the optimized conditions, which was much higher than those of conventional organic solvents. The antioxidant activity of PAC extracted by Ch-M 55 was similar to that of 70% acetone, but a little less than 70% methanol and 70% ethanol. The differences in constituent and polymerization degree of PAC extracted by different solvents might account for the difference in antioxidant activity. In consideration of biodegradability and pharmaceutical acceptability, the Ch-M 55 -based extraction method is obviously efficient, green and ecofriendly. Extraction of PAC from Ginkgo biloba leaves also provides a new PAC resource. [ABSTRACT FROM AUTHOR]

Deep eutectic solvents (DESs), especially hydrophilic DESs, have been considered green substitutes to conventional organic solvents for bioactive compounds extraction. This study provided a practical example demonstrating the efficiency of hydrophobic DESs as designer solvent to extract polyprenyl acetates from Ginkgo biloba leaves. A hydrophobic ternary DES named as MCO gave the highest extraction yield for polyprenyl acetates during the initial screening. It was tailor-made from methyl trioctyl ammonium chloride, capryl alcohol and octylic acid at a molar ratio of 1:2:3 by systematically optimizing the DES component type, molar ratio and number. With MCO-based extraction, the operational factors influencing the extraction yield were further optimized by statistical method. The model for the extraction of polyprenyl acetates was well established and verified. Extraction yield of 84.11 ± 0.7366 was obtained at the optimal conditions, which was much higher than those of conventional hydrophobic organic solvents (petroleum ether and n -hexane). Moreover, excellent recovery of polyprenyl acetates from MCO extraction solution was obtained by macroporous resin AB-8 or DM130 adsorption. This study demonstrated that not only hydrophilic DESs but also hydrophobic DESs can be adopted as solvents for bioactive compounds extraction from biomass. [ABSTRACT FROM AUTHOR]

[Display omitted] • An HDES-based microextraction method was developed for the determination of GAs. • The developed method had better efficiency than traditional methods. • The method could be applied for the determination of GAs in different samples. For the quantification of ginkgolic acids (GAs) within ginkgo products, a very effective liquid–liquid microextraction pretreatment method based on hydrophobic deep eutectic solvent (HDES) was created. The HPLC detection conditions for GAs were optimized before establishing the pretreatment method. Then, the DES composition, DES volume, sample amount, extraction temperature and time were investigated to obtain the optimal pretreatment conditions. This developed method had satisfactory analytical performance, the linearity was r2 = 0.9997, and its low limit of detection (LOD) was 0.81 mg/kg. The recovery value ranged from 95.10 % to 98.75 %. When compared with the Ch.P.2010 and EP10.0 recommended methods, this developed method gave a higher efficiency and showed obvious advantages. Furthermore, the developed method was effectively used to identify GAs in a variety of Ginkgo biloba medications, Ginkgo biloba leaves from various cultivars and collection times. These results highlighted the superiorities of the HDES-based liquid–liquid microextraction pretreatment technique for the measurement of GAs, providing insights for future development of efficient methods in active ingredients analysis. [ABSTRACT FROM AUTHOR]

[Display omitted] • The research status of the bioactive components in Ginkgo biloba seed exocarp was reviewed. • A summary on the other components in Ginkgo biloba seed exocarp was made. • The bioactivities Current researches on the application of Ginkgo biloba seed exocarp were discussed. • The development direction of Ginkgo biloba seed exocarp was suggested. Ginkgo biloba seed exocarp contains a variety of bioactive components, such as polysaccharides, flavonoids, terpenoid trilactones, and ginkgolic acids, which have a high value of utilization. However, Ginkgo biloba seed exocarp is always treated as waste of ginkgo seeds processing. To maximize the utilization of Ginkgo biloba seed exocarp, it is necessary to deliberate and arouse researchers' attention. This review demonstrated the extraction method, purification method, and determination method of bioactive components in Ginkgo biloba seed exocarp and summarized its composition and bioactivities. Moreover, the future study of Ginkgo biloba seed exocarp resource is prospected, hoping to provide a theoretical basis and direction for its further development and utilization. [ABSTRACT FROM AUTHOR]

Botanical natural bioactive ingredients are difficult to purify due to their complicated composition and structure, and are usually utilized in the form of phytocomplex, which refers to a mixture of multiple bioactive ingredients. Using biocompatible solvents as delivery solvents is a simple, versatile, and scalable method to improve the solubility of phytocomplex. In this work, the extract of Ginkgo biloba leaves (EGb) was chosen as the model of the phytocomplex to systematically investigate the potential of natural deep eutectic solvents (NADESs) as solubilizers. After initial screening, the solubilities of EGb in different NADESs were 29–1500 folds higher than those in water. Several solvatochromic parameters of NADESs were employed to tentatively study the solvation between bioactive compounds and NADESs. The high solubility of EGb in NADESs could be interpreted by the hydrogen bond interactions. Additionally, further investigation on the stability and bioactivity of EGb dissolved in NADESs helped to validate the feasibility of using NADESs as solubilizers. The results suggested that not only the stability but also the bioactivity of EGb kept at high levels after dissolving in NADESs. The findings of this study showed the bright application prospect of NADESs as solubilizers, which offers a new avenue for improving the solubility of insoluble phytocomplex. [Display omitted] • Extract of Ginkgo biloba leaves (EGb) is a typical model of phytocomplex. • Natural deep eutectic solvents (NADESs) were firstly used to improve the solubility of phytocomplex. • The structure of EGb did not change after being dissolved in NADESs. • The stability and biological activity of EGb maintained after being dissolved in NADESs. • NADESs can be used as solubilizers to prepare liquid formulations. [ABSTRACT FROM AUTHOR]

[Display omitted] • An l -menthol based hydrophobic ternary deep eutectic solvent was tailor-made. • The hydrophobic ternary deep eutectic solvent was employed for removing ginkgolic acids. • Ginkgolic acids can be removed by simple oscillation and centrifugation. • The residual ginkgolic acids can be lower than 5.00 mg/kg after only one-time removal. • Scale up to 100 times can still hold satisfactory removal efficiency. Extract of Ginkgo biloba leaves (EGb) is a widely used phytotherapy drug, while ginkgolic acids (GAs) are considered as potentially hazardous constituents in EGb. In this work, a liquid-liquid microextraction method for removing ginkgolic acids from Ginkgo biloba leaves crude extract using hydrophobic deep eutectic solvent (DES) was reported. After screening and designing, a ternary hydrophobic DES composed of l -menthol, 1-hexanol and lauric acid at a molar ratio of 1:0.8:0.2, named as MHL, gave the highest removal rate of GAs. The removal conditions were optimized based on the removal rate of GAs, and the optimal conditions were 27.5 % (v/v) of ethanol solution used as the aqueous phase for dissolving the Ginkgo biloba leaves crude extract, 180 μL of the hydrophobic DES, removal temperature of 40 °C, and removal time of 24 min, respectively. Under these conditions, the removal rate of GAs in the model EGb solution reached 74.35 ± 1.56 %. Only one step removal could reduce the GAs content in the real Ginkgo biloba leaves crude extract to 4.02 μg/g (below 5.00 mg/kg). Scaling up the removal operation volume by 100 times, the removal rate of GAs did not decrease, but even improved. The retention rates of total flavonoids and ginkgolides always kept at high levels. This work provides the basic for further considering hydrophobic DESs as green media for efficiently removing the GAs in the standardized EGb production. [ABSTRACT FROM AUTHOR]

Membrane separation technology was tried to remove the ginkgotoxin (4′-O-methylpyridoxine and 4′-O-methylpyridoxine-5′-glucoside) from Ginkgo seeds powder for the first time in this work. 99.88 ± 0.99% of the ginkgotoxin could transfer to the extraction solvent from the Ginkgo seeds powder when the water was used as the extraction solvent for extracting twice at 25 °C and solid to solvent ratio of 1:40 (g/mL) for 20 min. The conditions of ginkgotoxin removal by membrane separation were next studied as: ultrafiltration membrane with cut-off molecular weight of 10000 Da was operated at 0.2–0.3 MPa with a permeate volume of 4.7 L, and nanofiltration membrane with cut-off molecular weight of 600 Da was operated at 0.4–0.5 MPa with a permeate volume of 3.0 L. All the ginkgotoxin could be removed under the selected membrane operation conditions. The main nutritional and functional components of Ginkgo seeds powder were well preserved after detoxification. The main characteristics or structure of the detoxified Ginkgo seeds powder were not obviously changed. The membrane separation technology could be used as an effective method for removing ginkgotoxin from Ginkgo seeds powder. Image 1 • Overconsumption of Ginkgo biloba seeds leads to poisoning. • MPN and MPNG collectively called as ginkgotoxin are responsible for poisoning. • 99.88 ± 0.99% of the ginkgotoxin could be extracted out with water. • All the ginkgotoxin could be removed under the optimal membrane separation conditions. • Main components and characteristics were well preserved after detoxification. [ABSTRACT FROM AUTHOR]

• Overconsumption of Ginkgo biloba seeds leads to poisoning. • 4'-O-methylpyridoxine (MPN) and MPN-5'-glucoside (MPNG) are responsible for poisoning. • Heat treatment could increase the MPNG content but decrease the MPN content. • Non-enzymatic and enzymatic glycosylation could not explain the transformation. • Enzymatic hydrolysis could explain the dynamic relationship between the MPN and MPNG. Overconsumption of Ginkgo biloba seeds leads to poisoning. 4'-O-methylpyridoxine (MPN) and 4'-O-methylpyridoxine-5'-glucoside (MPNG) are responsible for poisoning by intaking ginkgo seeds. It had been reported that heat treatment could increase the MPNG content but decrease the MPN content in ginkgo seeds. However, the definite mechanism for the transformation of MPN and MPNG in ginkgo seeds undergoing heat treatment has not been elucidated to this day. In this work, a Chinese ginkgo cultivar was firstly employed to investigate the effect of heat treatment on the levels of MPN and MPNG. Similar syngenetic succession between the MPN and MPNG contents was also found. Several groups of experiments were further designed to explore the interconversion mechanism between MPN and MPNG under heat treatment. The results showed that non-enzymatic and enzymatic glycosylation mechanisms could not explain the transformation between MPN and MPNG. Enzymatic hydrolysis mechanism could better explain the dynamic relationship between the MPN and MPNG. Therefore, inactivating the endogenous enzymatic hydrolysis before HPLC analysis is needed to accurately determine the contents of MPN and MPNG in the ginkgo seeds. [ABSTRACT FROM AUTHOR]