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Cholestasis refers to a physiological and pathological process caused by bile acid (BA) overaccumulation inside the circulatory system and liver, leading to systemic and hepatocellular damage. Activating the farnesol X receptor (FXR) to restore BA homeostasis is a promising strategy for treating cholestasis. The objective of this research is to reveal solid evidence for the fact that the total iridoid glycosides from Swertia mussotii Franch. (IGSM) alleviate cholestasis. In this research, the whole plant of S. mussotii was extracted with 70% ethanol and separated by macroporous adsorption resin. A rat cholestasis model was established by the injection of α-naphthyl isothiocyanate (ANIT) at a dose of 75 mg/kg. Biochemical and oxidative stress indicators were determined using commercial assay kits. The mRNA abundance of FXR and target proteins was assessed using RT-qPCR. In addition, the effects of main compounds with FXR were evaluated by molecular docking after IGSM analysis using UPLC. The results indicated that IGSM alleviated ANIT-induced cholestasis through reducing serum ALT, AST, AKP, and TBA levels; increasing the mRNA levels of Fxr, Besp, Ntcp, and Mep2; and reducing oxidative stress. The proportion of iridoid compounds in IGSM exceeded 50%, which may be the active substance basis of IGSM. This study provides a theoretical reference for IGSM in the treatment of cholestasis, and future studies may delve more deeply into the FXR regulatory pathway. [ABSTRACT FROM AUTHOR]

A phytochemical investigation on the 80% EtOH extract of the leaves of Paederia scandens (Lour.) Merr. resulted into the isolation of three undescribed iridoid glycosides, 10-O-trans-p-coumaroyl-(4R,6R)-3,4-dihydro-3α-methylthiopaederoside (1), 10-O-trans-feruloyl-(4S,6R)-3,4-dihydro-2′-O-3α-paederoside (2), and 10-O-trans-caffeoyl-paederosidic acid ethyl ester (3). The structures of the new compounds were elucidated by spectral methods such as 1D and 2D (1H-1H COSY, HMQC, and HMBC) NMR spectroscopy, as well as high resolution mass spectrometry. The isolated compounds were tested in vitro for cytotoxic activity against five endocrine tumor cell lines. As a result, compound 1 exhibited some cytotoxicities against all the tested tumor cell lines with IC50 value less than 20.0 μM. [ABSTRACT FROM AUTHOR]

Two new iridoid glycosides, maytenhoiridosides A (1) and maytenhoiridosides B (2), along with three known compounds (3 – 5), were isolated from the branches of Maytenus hookeri. Their chemical structures were elucidated by HR-ESI-MS, 1D and 2D-NMR spectra, acid hydrolysis analysis, and comparison with literature data. Among the isolated compounds, compound 5 exhibited significant cytotoxic activity against the HCT-116, SKOV3 and SK-Hep-1 cells, with IC 50 values of 9.49±1.40, 34.66±1.48 and 12.66±3.32 µM, respectively, while the others showed weak or no activity at 50 μM. [Display omitted] • Two new iridoid glycosides were isolated from Maytenus hookeri. • The structures were confirmed by extensive spectroscopic analyses. • Compound 5 exhibited significant cytotoxic activities. [ABSTRACT FROM AUTHOR]

Two previously undescribed iridoid glycosides, 6'-O-trans-feruloyl-(4S,6R)-3,4-dihydro-3β-ethoxypaederoside (1) and 6'-O-trans-caffeoyl-(4S,6R)-3,4-dihydro-2'-O-3α-paederoside (2), were isolated from the 90% EtOH extract of the air dried aerial parts of Paederia Foetida. Structural elucidation of all the compounds was performed by spectral methods such as 1D and 2D (1H-1H COSY, HMQC, and HMBC) NMR spectroscopy. The two isolated iridoid glycosides were tested in vivo for their antinociceptive properties. As a result, 2 showed potent antinociceptive effect and its ID50 value (53.4 μmol/kg) was 2-fold less than those of the positive control drugs aspirin and acetaminophen. [ABSTRACT FROM AUTHOR]

Two new iridoid glycosides, piasezkiiosides A (1) and B (2), were isolated from aqueous extract of the whole plant of Rehmannia piasezkii. Their structures were established from the spectroscopic data, chemical transformation, and X-ray diffraction analysis. Compound 1 exhibited weak hepatoprotective activity against APAP-induced HepG2 cell damage. [ABSTRACT FROM AUTHOR]

Quality control and clarifying ingredients are the foundation of pharmacodynamic material basis research. Pedicularis decora Franch. (P. decora) is clinically used to treat Alzheimer's disease and exerts significant antioxidative, anti-inflammatory and neuroprotective effects. However, there is little systematic research on the extraction and composition and the current research on P. decora focused on the quality control and extraction with aucubin as only quality marker. It reported that Iridoid glycosides (IGs) and phenylpropanoid glycosides (PeGs), which are characteristic components of the Pedicularis species, have been reported to have various anti-Alzheimer's activity. This study focused on the extraction and rapid qualitative analysis of IGs and PeGs in P. decora. First, HPLC-UV method was established to detect five IGs and PeGs analytes simultaneously and assess the effect of the extraction technology. Then, the G1-entropy method with the Box-Behnken response surface design methodology was used to optimized extraction technology. The optimum conditions were determined to be reflux with 55% methanol aqueous solutions, at 75 °C for 50 min. Finally, by establishing UPLC-Q/TOF-MS, 15 IGs and 15 PeGs in P. decora were rapidly identified and characterized for the first time. The results will provide a reverence of a higher quality standard and the pharmacodynamic material basis research. [ABSTRACT FROM AUTHOR]

Morinda officinalis is a traditional Chinese tonic herb, and have been used in the treatment of multiple diseases. Here, three iridoid glycosides isolated from M. officinalis were evaluated for their roles in the autophagy-lysosomal pathway. All three iridoid glycosides could induce TFEB/TFE3-mediated lysosomal biogenesis and trigger autophagy. Interestingly, they promoted the nuclear import of TFEB/TFE3 without affecting their nuclear export, suggesting their role in the maintenance of lysosomal homeostasis. The results from this study shed light on the identification of autophagy activators from M. officinalis and provide a basis for developing them in the treatment of oxidative stress-involved diseases. [ABSTRACT FROM AUTHOR]

Fekade Beshah Tessema,1,2 Yilma Hunde Gonfa,2,3 Tilahun Belayneh Asfaw,4 Mesfin Getachew Tadesse,2,5 Rakesh Kumar Bachheti2,6 1Department of Chemistry, College of Natural and Computational Science, Woldia University, Woldia, Ethiopia; 2Department of Industrial Chemistry, College of Natural and Applied Sciences, Addis Ababa Science and Technology University, Addis Ababa, Ethiopia; 3Department of Chemistry, College of Natural and Computational Science, Ambo University, Ambo, Ethiopia; 4Department of Chemistry, College of Natural and Computational Science, Gondar University, Gondar, Ethiopia; 5Centre of Excellence in Biotechnology and Bioprocess, Addis Ababa Science and Technology University, Addis Ababa, Ethiopia; 6Department of Allied Sciences, Graphic Era Hill University, Society Area, Clement Town, Dehradun, 248002, IndiaCorrespondence: Fekade Beshah Tessema, Tel +251913141754, Email fbms08@gmail.comBackground: Ajuga integrifolia (Armagusa) is used as a decoction to treat high blood pressure and diabetes, widely in Ethiopia. Specific compounds for anti-hypertension activity were not identified so far. This study aims to provide a scientific basis for the therapeutic use of A. integrifolia as an antihypertension agent.Methods: In silico studies were used to evaluate the antihypertensive components of A. integrifolia. Flavonoids identified using HPLC analysis and iridoid glycosides isolated from A. integrifolia in this study and those isolated from synonyms (A. remota and A. bractosa) were considered in the molecular docking study. Interactions were studied by using Autodock vina (1.2) on PyRx 0.8 and visualizing in 2D and 3D using ligPlot+ and Discovery studio software. Activities like vasoprotection and druglikeness properties were predicted using online servers.Results: Flavonoids such as quercetin, myricetin, and rutin were identified and quantified by HPLC analysis from different extracts of A. integrifolia. Reptoside and 8-O-acetylharpgide isolated from the aerial part of A. integrifolia. The binding energies of all 17 candidates considered in this study range from − 10.2 kcal/mol to − 7.5 kcal/mol and are lower than enalapril (reference drug: − 5.9 kcal/mol). The binding energies, in most case, constitute hydrogen bonding. Biological activity predicted using PASS test also showed that the flavonoids have more probability of activity than the iridoid glycosides. Druglikeness properties of the candidate molecules showed that most follow the Lipinski rule of five with few violations.Conclusion: Lower binding energies involving hydrogen bonding and predicted activities concerning hypertension confirm the traditional use of the aerial part of the medicinal plant concerned. Flavonoids: rutin, myricetin, quercetin, and kaempferol take the leading role in the antihypertensive activity of the aerial part of A. integrifolia. The iridoid glycosides studied are almost similar in their effect on their antihypertensive activity and still better than the reference drug.Keywords: A. integrifolia, antihypertension, flavonoids, iridoid glycosides

This study was set to study the anti-proliferative effects of secoxyloganin in MDA-MB-231 breast cancer cells. The MTT cell viability assay results demonstrated that secoxyloganin significantly (p

Plants growing outside their native range may be confronted by new regimes of herbivory, but how this affects plant chemical defence profiles has rarely been studied.Using Plantago lanceolata as a model species, we investigated whether introduced populations show significant differences from native populations in several growth and chemical defence traits. Plantago lanceolata (ribwort plantain) is an herbaceous plant species native to Europe and Western Asia that has been introduced to numerous countries worldwide.We sampled seeds from nine native and 10 introduced populations that covered a broad geographic and environmental range and performed a greenhouse experiment, in which we infested half of the plants in each population with caterpillars of the generalist herbivore Spodoptera littoralis. We then measured size‐related and resource‐allocation traits as well as the levels of constitutive and induced chemical defence compounds in roots and shoots of P. lanceolata.When we considered the environmental characteristics of the site of origin, our results revealed that populations from introduced ranges were characterized by an increase in chemical defence compounds without compromising plant biomass. The concentrations of iridoid glycosides and verbascoside, the major anti‐herbivore defence compounds of P. lanceolata, were higher in introduced populations than in native populations. In addition, introduced populations exhibited greater rates of herbivore‐induced volatile organic compound emission and diversity, and similar chemical diversity based on untargeted analyses of leaf methanol extracts.In conclusion, the geographic origin of the populations had a significant influence on morphological and chemical plant traits, suggesting that P. lanceolata populations are not only adapted to different environments in their native range, but also in their introduced range. Read the free Plain Language Summary for this article on the Journal blog. [ABSTRACT FROM AUTHOR]

Cholestasis refers to a physiological and pathological process caused by bile acid (BA) overaccumulation inside the circulatory system and liver, leading to systemic and hepatocellular damage. Activating the farnesol X receptor (FXR) to restore BA homeostasis is a promising strategy for treating cholestasis. The objective of this research is to reveal solid evidence for the fact that the total iridoid glycosides from Swertia mussotii Franch. (IGSM) alleviate cholestasis. In this research, the whole plant of S. mussotii was extracted with 70% ethanol and separated by macroporous adsorption resin. A rat cholestasis model was established by the injection of α-naphthyl isothiocyanate (ANIT) at a dose of 75 mg/kg. Biochemical and oxidative stress indicators were determined using commercial assay kits. The mRNA abundance of FXR and target proteins was assessed using RT-qPCR. In addition, the effects of main compounds with FXR were evaluated by molecular docking after IGSM analysis using UPLC. The results indicated that IGSM alleviated ANIT-induced cholestasis through reducing serum ALT, AST, AKP, and TBA levels; increasing the mRNA levels of Fxr, Besp, Ntcp, and Mep2; and reducing oxidative stress. The proportion of iridoid compounds in IGSM exceeded 50%, which may be the active substance basis of IGSM. This study provides a theoretical reference for IGSM in the treatment of cholestasis, and future studies may delve more deeply into the FXR regulatory pathway.

Six new iridoid glycosides were isolated from the ethyl acetate fraction of the whole plants of Hedyotis diffusa Willd. They were identified as E-6-O-p-methoxycinnamoyl-10-O-acetyl scandoside acid methyl ester (1), Z-6-O-p-methoxycinnamoyl-10-O-acetyl scandoside acid methyl ester (2), E-6-O-caffeoyl scandoside methyl ester (3), E-6-O-p-coumaroyl-6′-O-acetyl scandoside methyl ester (4), Z-6-O-p-coumaroyl-6′-O-acetyl scandoside methyl ester (5), and E-6-O-p-coumaroyl-4′-O-acetyl scandoside methyl ester (6). The structures of them were elucidated based on unambiguous spectroscopic data (UV, IR, HRESIMS, and NMR). They were screened for anti-inflammatory effect, antioxidant effect, antitumor effect, and neuroprotective effect and did not show potent activities. [ABSTRACT FROM AUTHOR]

Fresh Rehmanniae Radix, as well as its processed products, are widely used in the clinical practice of traditional Chinese medicine. It is mainly available in four forms: fresh Rehmanniae Radix, raw Rehmanniae Radix, prepared Rehmanniae Radix, and nine-steamed, nine-dried Rehmanniae Radix. Pharmacological studies have shown that all Rehmanniae Radix forms contain iridoid glycosides and sugar compounds with various effects, including hypoglycemic, anti-inflammatory, neuroprotective, immunological enhancement, and bone marrow hematopoiesis-promoting activities. Differences in the efficacy among these Rehmanniae Radix forms and their processed products have been attributed to variations in their chemical compositions, particularly in iridoid glycosides and sugar compounds; however, the specific compositional differences in glycosides and sugars among the four forms of Rehmanniae Radix have not been clarified. Therefore, this study aims to qualitatively characterize the iridoid glycosides and sugar compounds in fresh Rehmanniae Radix, raw Rehmanniae Radix, prepared Rehmanniae Radix, and nine-steamed, nine-dried Rehmanniae Radix. [ABSTRACT FROM AUTHOR]

Acute inflammation may develop into chronic, life-threatening inflammation-related diseases if left untreated or if there are persistent triggering factors. Cancer, diabetes mellitus, stroke, cardiovascular diseases, and neurodegenerative disorders are some of the inflammation-related diseases affecting millions of people worldwide. Despite that, conventional medical therapy such as non-steroidal anti-inflammatory drugs (NSAIDs) is associated with serious adverse effects; hence, there is an urgent need for a newer and safer therapeutic alternative from natural sources. Iridoids are naturally occurring heterocyclic monoterpenoids commonly found in Rubiaceae plants. Plant extracts from the Rubiaceae family were demonstrated to have medicinal benefits against neurodegeneration, inflammation, oxidative stress, hyperglycaemia, and cancer. However, the therapeutic effects of natural iridoids derived from Rubiaceae as well as their prospective impacts on inflammation in vitro and in vivo have not been thoroughly explored. The databases of PubMed, Scopus, and Web of Science were searched for pertinent articles in accordance with PRISMA-ScR guidelines. A total of 31 pertinent articles from in vitro and in vivo studies on the anti-inflammatory potentials of iridoids from Rubiaceae were identified. According to current research, genipin, geniposide, and monotropein are the most researched iridoids from Rubiaceae that reduce inflammation. These iridoids primarily act by attenuating inflammatory cytokines and mediators via inhibition of the NF-κB signalling pathway in various disease models. A comprehensive overview of the current research on the anti-inflammatory properties of iridoids from the Rubiaceae family is presented in this review, highlighting the characteristics of the experimental models used as well as the mechanisms of action of these iridoids. To develop an alternative therapeutic agent from iridoids, more studies are needed to elucidate the effects and mechanism of action of iridoids in a wide variety of experimental models as well as in clinical studies pertaining to inflammation-related diseases.

Background: Scrophularia oblongifolia belongs to the Scrophulariaceae family, commonly known as the water figwort in Iran. It has been known as a traditional medicinal plant in Iran. Objective: This study was designed to investigate the phytochemicals and antimicrobial activity of ethyl acetate, methanol, MeOH: H2O (50:50 v/v), and n-hexane extract of Scrophularia oblongifolia aerial parts, growing in the Kangavar region in the Kermanshah province of Iran. Methods: Compounds of ethyl acetate extract were isolated by chromatographic techniques (HPLC-PDA-MS/MS-Q-TOF) and their structures were elucidated by spectral methods (1D and 2D NMR). The antifungal and antibacterial activities of some new compounds and ethyl acetate, methanol, and n-hexane extract were evaluated. Results: Two new polyphenol iridoid glycosides with phenylpropanoid moiety namely scrophuloside A5 and scrophuloside A6; two known phenylpropanoid glycosides namely scrophuloside A3 and scrophuloside A4, and two known iridoid glycosides namely aucubin and harpagoside were isolated from S. oblongifolia. Pure compounds showed high antifungal activities with MIC values ranging from 0.35 to 0.74 µg/ml against C. albicans and high antibacterial activities with MIC values ranging from 0.70 to 1.48 µg/ml against G. vajinalis. n-Hexan extract showed moderate antibacterial and antifungal activity, while methanol and methanol:H2O (50:50 v/v) extract showed no antimicrobial activities. Conclusion: Based on these findings, compounds isolated from S. oblongifolia have demonstrated potential antibacterial and antifungal activities.

Premna fulva Craib, rich in iridoid glycosides, is widely used to treat periarthritis, osteoproliferation, pain, and other diseases. However, no studies have reported effective purification methods for obtaining iridoid glycosides as active materials. This paper describes an efficient strategy for separating iridoid glycosides from Premna fulva leaves using high‐speed counter‐current chromatography and preparative high‐performance liquid chromatography. A two‐phase solvent system, ethyl acetate/n‐butanol/water (7.5:2.5:10, v/v), was selected for high‐speed counter‐current chromatography separation. The proposed method effectively separated and purified four iridoid glycosides and four lignans, including three new iridoid glycosides (4–6) and five known compounds (1–3, 7, 8), from Premna fulva leaves, indicating that high‐speed counter‐current chromatography combined with prep‐HPLC can efficiently isolate catalpol derivatives from the genus Premna. Additionally, the in vitro anti‐inflammatory activities of all isolated compounds were analyzed using lipopolysaccharide‐stimulated RAW 264.7 cells, and the results indicated that six compounds (1 and 3–7) exhibited potential anti‐inflammatory activities. [ABSTRACT FROM AUTHOR]

Efficient strategies for the preparative separation of iridoid glycosides and flavonoid glycosides from Hedyotis diffusa using preparative high‐performance liquid chromatography combined with appropriate pretreatment technologies were developed. Four fractions (Fr.1‐1, Fr.1‐2, Fr.1‐3, and Fr.2‐1) were firstly isolated from the crude extract of Hedyotis diffusa by column chromatography with C18, resin, and silica gel materials, respectively. Then, corresponding separation strategies were developed according to the polarity and chemical constituents. High‐polar compounds of Fr.1‐1 were purified by hydrophilic reversed‐phase liquid chromatography and hydrophilic interaction liquid chromatography mode. The combination of C18 and phenyl columns realized the complementary separation of iridoid glycosides in Fr.1‐2. Meanwhile, the improved selectivity caused by the change of organic solvent in the mobile phase was utilized to realize the purification of flavonoid glycosides in Fr.1‐3 and Fr. 2‐1. Finally, 27 compounds (purity > 95%) mainly involving nine iridoid glycosides and five flavonoid glycosides were obtained. A complete strategy was established for the separation of a complex sample with a wide polarity range, to jointly solve the problems of enrichment of target components and separation of structural analogs. [ABSTRACT FROM AUTHOR]

Two new iridoid glycosides, named 3′-O-benzoyl-dolichocymboside D (1) and dolichocymboside E (2), along with ten known glycosides (3–12), were isolated from the ethanol extract of the whole plants of Odontites vulgaris Moench. The structures of the isolated compounds were elucidated by 1D and 2D NMR and HR-ESI-MS spectra and by comparison with those reported in the literature. This is the first report on compounds 11 and 12 isolated from the family Scrophulariaceae, and compounds 8–10 were isolated from the genus Odontites. [ABSTRACT FROM AUTHOR]

Monoterpenoids are C10 isoprenoid natural products with diverse functions as volatile and non-volatile secondary metabolites. Their biosynthesis from acyclic diphosphate precursors is often accompanied by one or more ring closures, which stabilize the linear, carbocationic intermediates generated during typical terpene synthase reaction sequences. The subset that remains uncyclized following the elimination of the diphosphate group correspondingly retains higher reactivity than their cyclized counterparts, a property that may explain the additional transformations that geraniol and other acyclics undergo to yield monoterpene aldehydes, acids, esters, glycosides, and iridoids, many of which possess allelochemical activity as pollinator attractants, feeding deterrents, or insect repellents. Essential oils of lemon grass (or citronella) (Cymbopogon), rose-scented geraniums (Pelargonium), and lemon-scented gums (Corymbia) are rich sources of the acyclic monoterpene alcohols we collectively refer to in this review as 'citronelloids'. Their formation from geranyl diphosphate may be brought about by the tps-g or tps-b subclade of terpene synthases or, alternatively, by a subclade of Nudix hydrolases which act preferentially on prenyl diphosphate substrates, yielding monoterpene alcohols in a two step process that involves a monophosphate intermediate. In some members of the Lamiid and Campanulid clades, further oxidation of geraniol and a non-classical, reductive cyclization leads to the iridoids, a group of mostly non-volatile, bicyclic monoterpenes with potent anti-herbivory and anti-inflammatory properties. Here we review the recent literature on acyclic monoterpene biosynthesis, their natural distribution across the plant kingdom, and their emerging roles in medicine as biologically active natural products. [ABSTRACT FROM AUTHOR]

Fresh Rehmanniae Radix, as well as its processed products, are widely used in the clinical practice of traditional Chinese medicine. It is mainly available in four forms: fresh Rehmanniae Radix, raw Rehmanniae Radix, prepared Rehmanniae Radix, and nine-steamed, nine-dried Rehmanniae Radix. Pharmacological studies have shown that all Rehmanniae Radix forms contain iridoid glycosides and sugar compounds with various effects, including hypoglycemic, anti-inflammatory, neuroprotective, immunological enhancement, and bone marrow hematopoiesis-promoting activities. Differences in the efficacy among these Rehmanniae Radix forms and their processed products have been attributed to variations in their chemical compositions, particularly in iridoid glycosides and sugar compounds; however, the specific compositional differences in glycosides and sugars among the four forms of Rehmanniae Radix have not been clarified. Therefore, this study aims to qualitatively characterize the iridoid glycosides and sugar compounds in fresh Rehmanniae Radix, raw Rehmanniae Radix, prepared Rehmanniae Radix, and nine-steamed, nine-dried Rehmanniae Radix.

Three undescribed iridoid glycosides, cyc(7 β - O -6′)-morroniside (1), 6′-methyl succinate-7 β - O -methylmorroniside (2), and 7 β - O -methyl phenyllactate morroniside (3) were isolated from 50% ethanol extract of Cornus officinalis fruits. The structures of the isolated compounds were determined by HRESIMS, 1D NMR, 2D NMR, UV and IR spectroscopic methods. Compounds 1 - 3 exhibited moderate anti-inflammatory activities in vivo in a CuSO 4 -induced zebrafish inflammation model (when evaluated at 50 μM). [Display omitted] • Three undescribed iridoid glycosides were isolated from Cornus officinalis fruits. • The structures were established by spectroscopic data. • All compounds showed anti-inflammatory activity on zebrafish inflammation model. [ABSTRACT FROM AUTHOR]

"Desert hyacinths" are a remarkable group of parasitic plants belonging to genus Cistanche, including more than 20 accepted species typically occurring in deserts or coastal dunes parasitizing roots of shrubs. Several Cistanche species have long been a source of traditional herbal medicine or food, being C. deserticola and C. tubulosa the most used in China. This manuscript reports the isolation and identification of some phenylethanoid and iridoid glycosides, obtained from the hydroalcoholic extract of C. phelypaea collected in Spain. The present study aims to characterize the antioxidant activity of C. phelypaea metabolites in the light of their application in nutraceutical and cosmeceutical industries and the effect of acetoside, the most abundant metabolite in C. phelypaea extract, on human keratinocyte and pluripotent stem cell proliferation and differentiation. Our study demonstrated that acetoside, besides its strong antioxidant potential, can preserve the proliferative potential of human basal keratinocytes and the stemness of mesenchymal progenitors necessary for tissue morphogenesis and renewal. Therefore, acetoside can be of practical relevance for the clinical application of human stem cell cultures in tissue engineering and regenerative medicine. [ABSTRACT FROM AUTHOR]

Gardenia jasminoides Ellis (Zhi-zi), which belongs to the Rubiaceae family, has been used mainly with its fry fruit for thousands of years, and it is an herb with the homology of medicine and food. In traditional Chinese medicine (TCM) theory, Zhi-zi can be used for "Quench Xiaoke", meaning for therapying diabetes in modern medicine. Based on numerous pharmacological studies, Gardenia jasminoides Ellis (Zhi-zi), and its ingredients, mainly including iridoid glycosides and carotenoids (crocins), possess potent antioxidant and anti-inflammatory properties, and can promote insulin secretion and sensitization, stimulate GLP-1 pathway activity, and protect islet β cells and the macro- and microvascular systems. These properties are the primary reasons why Zhi-zi and its ingredients are effective in reducing glucose levels, treating diabetes, and preventing its complications. This review aims to summarize the current situation and the advances of the studies on the mechanisms of Zhi-zi in improving diabetes and its complications, and it is expected to provide useful and systematic references for future research and clinical application of Zhi-zi and its active ingredients in the therapy of diabetes and complications. [Display omitted] [ABSTRACT FROM AUTHOR]

Iridoid glycosides (IGs) are secondary metabolites found in plants such as the noni plant (Morinda citrifolia L.), known for their diverse biological activities and potential health benefits. Herein, we screened fifteen natural deep eutectic solvents (NADES) and two conventional solvents (CS, 70% (V/V) methanol and 70% (V/V) ethanol) for extraction of IGs from noni fruit pomace. Our findings indicate that non-acidic NADES promote IG extraction. Glycerol/glycine combined with β-cyclodextrin was selected, and a molecular simulation was performed to elucidate the interaction between NADES components and IGs. Further, the structure-activity relationship and interaction mechanisms of IGs with α-glucosidase were investigated using multispectral and molecular docking tools. The results demonstrated that deacetylation of the B-ring's C-10 improved the inhibitory potential of IGs. Deacetylation produces hydrophobic contacts, which enhance the inhibitory effect of deacetylasperulosidic acid on α-glucosides. Additionally, hydrogen bonds and van der Waals forces drive the formation of non-covalent complexes between IGs and enzymes. [Display omitted] • Noni fruit pomace contains large amounts of iridoid glycosides (IGs). • Non-acid natural deep eutectic solvents (NADES) are favourable for IGs extraction. • NADES coupled with β-cyclodextrin is a greener option for the extraction of IGs. • Noni IGs have a good ability to inhibit α-glucosidase. • The inhibitory effect of noni IGs on α-glucosidase is increased by deacetylation. [ABSTRACT FROM AUTHOR]

Herbal medicines are still widely practiced in Kurdistan Region-Iraq, especially by people living in villages on mountainous regions. Among plants belonging to the genus Teucrium (family Lamiaceae), which are commonly employed in the Kurdish traditional medicine, we have analyzed, for the first time, the methanol and aqueous methanol extracts of T. parviflorum aerial parts. The plant is mainly used by Kurds to treat jaundice, liver disorders and stomachache. We aimed to determine the phytochemical profile of the extracts and the structures of the main components, so to provide a scientific rationale for the ancient use of the plant in the ethno-pharmacological field. TLC analysis of the two extracts on silica gel and reversed phase TLC plates, using different visualization systems, indicated similar contents and the presence of phenolics, flavonoids, terpenoids and sugars. The chlorophyll-free extracts exhibited weak/no antimicrobial activities against a panel of bacteria (MICs = 800–1600 µg/mL) and fungal strains (MICs ≥ 5 mg/mL). At the concentration of 600 µg/mL, the methanol extract showed moderate antiproliferative effects against A549 and MCF-7 cancer cell lines in the MTS assay. Moreover, both extracts exhibited a significant dose-dependent free radical scavenging action against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical (EC50 = 62.11 and 44.25 μg/mL, respectively). In a phytochemical study, a high phenolic content (77.08 and 81.47 mg GAE/g dry extract, respectively) was found in both extracts by the Folin–Ciocalteu assay. Medium pressure liquid chromatographic (MPLC) separation of the methanol extract on a reversed phase cartridge eluted with a gradient of MeOH in H2O, afforded two bioactive iridoid glucosides, harpagide (1) and 8-O-acetylharpagide (2). The structures of 1 and 2 were established by spectral data, chemical reactions, and comparison with the literature. Interestingly, significant amounts of hepatotoxic furano neo-clerodane diterpenoids, commonly occurring in Teucrium species, were not detected in the extract. The wide range of biological activities reported in the literature for compounds 1 and 2 and the significant antiradical effects of the extracts give scientific support to the traditional use in Iraqi Kurdistan of T. parviflorum aerial parts for the preparation of herbal remedies. [ABSTRACT FROM AUTHOR]

Four previously undescribed iridoid glycosides neocornuside A–D (1–4), along with six known ones (5–10), were isolated from Cornus officinalis fruit. Their structures were elucidated by extensive spectroscopic (NMR, UV, IR, and MS) analysis and comparison with data reported in the literature. All isolates were assessed for their antidiabetic activity on the relative glucose consumption in insulin-induced insulin-resistant HepG2 cells. The results showed that compounds 1, 3, and 7 exhibited significant antidiabetic activities with EC50 values of 0.582, 1.275, and 0.742 μM, respectively. Moreover, compounds 1, 3, and 7 could improve the ability of 2-NBDG uptake of insulin-induced HepG2 cells. [ABSTRACT FROM AUTHOR]

The tribe Antirrhineae of Plantaginaceae family is well known for various garden ornamentals (Antirrhinum L., Linaria Mill., Cymbalaria Hill.), numerous medicinal plants (Anarrhinum orientale Benth., Nanorrhinum ramosissimum (Wall.) Betsche, Linaria japonica Miq. etc.), besides, the Linaria genus is famous for the fact that it contains naturally-transgenic plants. Medicinal properties are caused by the presence of a certain spectrum of specialized metabolites. A major role among them in tribe Antirrhineae is played by iridoid glycosides, in particular antirrhinoside, antirrhide, linarioside and 6-O-acetylantirrinoside. This review summarizes the literature data on biosynthesis, methods of analysis, the diversity and distribution of these compounds in the representatives of the tribe, that makes it possible to use the obtained data for chemotaxonomy and pharmacology, and also indicates gaps in our knowledge regarding the biochemistry of such taxonomic groups as Anarrhinum, Maurandya, Gambelia, Chaenorhinum, Antirrhinum and Linaria. The general picture of the state of research indicates directions for future work. Despite the different degrees of study of the tribe representatives, we can conclude the presence of antirrhinoside as a marker of this group of plants. [ABSTRACT FROM AUTHOR]

Noni fruit has an unpleasant flavour but is highly bioactive. Therefore, it is necessary to clarify the effect of temperature regulation on quality of fermented noni fruit. In the present study, the formation of flavours, amino acid profiles, and iridoid glycosides during noni fruit fermentation at different temperatures were investigated. We initially found that different temperatures affected core microbial communities. The general evolutionary trends of Acetobacter and Gluconobacter were influenced by different temperatures. Furthermore, high temperature helped maintain low octanoic and hexanoic acids. Subsequently, we found that high temperature improved total amino acids and iridoid glycosides. The correlation network analysis revealed that bacterial communities impacted the quality (volatile flavours, amino acid profiles, and iridoid glycosides) of fermented noni fruit. Overall, altering the temperature induced variations in microbial communities and quality during the noni fruit fermentation process. These results are instrumental in the pursuit of quality control in natural fermentation processes. • Temperature affected microbial composition during noni fruit fermentation. • High temperature improved unpleasure odors, such as octanoic and hexanoic acid. • High temperature decreased the losses of amino acids and iridoid glycosides. • Correlation network showed the correlation of core bacteria and quality of noni. • Acetobacter could be potential microbial starters for noni fruit fermentation. [ABSTRACT FROM AUTHOR]

The phytochemical studies on the aerial parts of Sideritis dichotoma led to the isolation and identification of a new iridoid glycoside (1), along with four known iridoid glycosides (2 - 5), three phenylethanoid glycosides (6 – 8), two flavone glycosides (9 and 10), one neolignan (11) and a megastigmane glycoside (12). Their structures were elucidated by spectroscopic techniques. Compounds 2 , 3 and 12 have never been found in the Sideritis genus before. Furthermore, eleven compounds (1 – 5 , 7 – 12) were characterized for the first time from S. dichotoma. The chemotaxonomic importance of isolated compounds was discussed. This is the first phytochemical study on the polar constituents of S. dichotoma , an endemic species to Türkiye. [Display omitted] • A new iridoid glycoside (1) was obtained from Sideritis dichotoma. • Compounds 2 , 3 and 12 were isolated from the genus Sideritis for the first time. • First report on the existence of a megastigmane glycoside in the genus Sideritis. • All compounds are reported for the first time from S. dichotoma , but for 6. [ABSTRACT FROM AUTHOR]

Iridoids, an important active ingredient, are widely distributed in varieties of Chinese herbal medicines and have varieties of pharmacological activities, such as anti-tumor, hypoglycemic, anti-inflammatory and so on, most of which exist in the form of glycosides in nature. However, its clinical application is limited by poor lipid solubility, low bioavailability and short half-life. It is necessary to optimize the structure of iridoids. It is hard to modify the hydroxyl groups at specific sites because iridoid glycosides are polyhydroxy compounds and very complex. In this paper, the words of 'Iridoid glycosides' and 'Hydroxyl protection' were used as the keywords, more than 200 articles from 1965 to 2021 were obtained from databases, such as CNKI, PubMed, Scifinder and so on. Finally, 60 articles were selected to summarize the hydroxyl protection of iridoid glycosides, which will provide a theoretical basis for their structural modification and stimulate their application potential in the field of drug research and development. Iridoid glycosides are polyhydroxy compounds so it is challenging to modify the hydroxyl groups at their specific sites. In this paper, according to literature on hydroxyl protection and based on our practical research work on iridoid glycosides, the methods and applications of iridoid glycosides in hydroxyl protection were summarized and analyzed which laid a research foundation for the development of new iridoid glycosides. [ABSTRACT FROM AUTHOR]

Defense against natural enemies constitutes an important driver of herbivore host range evolution in the wild. Populations of the Baltimore checkerspot butterfly, Euphydryas phaeton (Nymphalidae), have recently incorporated an exotic plant, Plantago lanceolata (Plantaginaceae), into their dietary range. To understand the tritrophic consequences of utilizing this exotic host plant, we examined immune performance, chemical defense, and interactions with a natural entomopathogen (Junonia coenia densovirus, Parvoviridae) across wild populations of this specialist herbivore. We measured three immune parameters, sequestration of defensive iridoid glycosides (IGs), and viral infection load in field‐collected caterpillars using either P. lanceolata or a native plant, Chelone glabra (Plantaginaceae). We found that larvae using the exotic plant exhibited reduced immunocompetence, compositional differences in IG sequestration, and higher in situ viral burdens compared to those using the native plant. On both host plants, high IG sequestration was associated with reduced hemocyte concentration in the larval hemolymph, providing the first evidence of incompatibility between sequestered chemical defenses and the immune response (i.e., the "vulnerable host" hypothesis) from a field‐based study. However, despite this negative relationship between IG sequestration and cellular immunity, caterpillars with greater sequestration harbored lower viral loads. While survival of virus‐infected individuals decreased with increasing viral burden, it ultimately did not differ between the exotic and native plants. These results provide evidence that: (1) phytochemical sequestration may contribute to defense against pathogens even when immunity is compromised and (2) herbivore persistence on exotic plant species may be facilitated by sequestration and its role in defense against natural enemies. [ABSTRACT FROM AUTHOR]

Background: Nyctanthes arbor-tristis (NAT) is an ornamental garden plant traditionally used for treating many diseases such as helminthiasis, arthritis, and malaria. Aims: The aim of this study was to validate the ethnobotanical uses of the antimalarial activity of leaves of NAT by in vivo tests. Materials and Methods: Leaves of NAT were identified and authenticated and phytoconstituents of NAT were identified. The antimalarial activity of NAT was studied in in vivo for its schizonticidal activity, repository activity, and curative tests in Swiss albino mice by using Plasmodium berghei (ANKA). Statistical Analysis Used: One-way ANOVA was done for comparison of different groups followed by post hoc analysis (Tukey-Kramer multiple comparison tests). Level of significance was at P < 0.05. Results: The mean schizonticidal activity of NAT increased from 14.21 to 46.15 (P < 0.01) with doses ranging from 100 to 200 mg/kg compared to 67.29 with that of chloroquine (CQ). The repository activity with NAT doses 100–200 mg/kg increased from 12.91 to 42.85 (P < 0.01) compared to 78.79 in pyrimethamine 1.2 mg/kg/day. In Rane's test, there was chemosuppression in range of 55.50–65.02 (P < 0.01) with NAT in doses of 100–200 mg/kg compared to 74.15 with that of CQ 5 mg/kg. Conclusions: The antiplasmodial activity of NAT might be like that of artemisinin by producing oxidative stress mostly due to the iridoid glycosides. The active phytoconstituent(s) responsible may be tested individually or in combination both by in vitro and in vivo studies to identify the active chemical ingredient.

The species belonging to Scrophularia genus grow mainly in Irano-Turanian and Mediterranean regions and have been used as folk remedy for inflammatory-related diseases since ancient times. The present study was aimed to evaluate the anti-inflammatory activity of the extracts of Scrophularia kotschyana as well as the isolated compounds. The aerial parts and the roots of the plant were separately extracted with methanol. Anti-inflammatory activities of both extracts were evaluated with formalin test in mice. As the methanolic extract of the aerial parts significantly (p <.05) inhibited inflammation, it was then submitted to successive solvent extractions with n -hexane, dichloromethane, ethyl acetate and n -butanol to yield subextracts. Anti-inflammatory activities of the subextracts were evaluated within the same test system. Among the subextracts tested, the n -butanol subextract produced a significant (p <.05) anti-inflammatory activity at all doses (5, 10, and 30 mg/kg, ip.). Sequential chromatographic separation of the n -butanol subextract yielded 8-O-acetyl-4′- O -(E)- p -coumaroylharpagide, 8- O -acetyl-4′- O -(Z)- p -coumaroylharpagide, β-sitosterol 3- O -β-glucopyranoside, apigenin 7- O -β-glucopyranoside, apigenin 7- O -rutinoside, luteolin 7- O -β-glucopyranoside and luteolin 7- O -rutinoside. The anti-inflammatory activities of the isolates were evaluated at 5 mg/kg dose. Luteolin 7- O -β-glucopyranoside and apigenin 7- O -rutinoside caused a significant (p <.05) inhibition of oedema formation. [ABSTRACT FROM AUTHOR]

Objective: The iridoid glycosides were extracted and separated from Osmanthus fragrans seeds, and the potential protective effect of Osmanthus fragrans seed extract on concanavalin A-induced immune liver injury in mice was studied. Methods: Osmanthus fragrans seeds were extracted by 95% ethanol reflux. Then, the iridoid glycosides were enriched by extraction refined through petroleum ether (60°C–90°C), ethyl acetate, and water-saturated n-butanol in sequence, so as to purify the n-butanol part (Osmanthus fragrans seed's n-butanol extraction, OFSN) by macroporous resin. Specnuezhenide and Nuezhenoside G13 were used as the reference substances to determine the concentration of iridoid glycosides by HPLC. On this basis, a mouse immune liver injury model was established by tail intravenous concanavalin A (20 mg/kg); the contents of serum ALT, AST, IFN-γ, and TNF-α and the contents of liver tissue MDA and SOD were determined; the pathological changes of the liver by HE staining were observed; and the expression levels of p38MAPK and p-p38mapk in liver tissue were detected by WB. Results: The linearity, precision, repeatability, recovery, and stability of HPLC all met the requirements by validating with the methodology. The contents of Specnuezhenide and Nuezhenoside G13 in the n-butanol extracts were 39.20% and 39.88%, respectively. Actually, their contents can reach up to 82.56% and 87.9% after being purified by macroporous resin. The results of animal experiments show that OFSN could significantly reduce the liver and spleen index, reduce the ALT and AST contents in plasma and the MDA content in liver tissue, and then increase the SOD content. Besides, OFSN could also reduce the plasma IFN-γ and TNF-α levels. The HE staining result indicates that the pathological changes in the liver tissues of mice treated with OFSN are alleviated to different degrees while the WB result suggests that OFSN could significantly inhibit the expression of p-p38mapk. Conclusion: Osmanthus fragrans seeds are rich in iridoid glycosides, which has a good protective effect on mouse immune liver injury caused by concanavalin A. The mechanism may be related to inhibiting the phosphorylation of p38MAPK, inhibiting the release of inflammatory mediators, improving the antioxidant capacity of liver cells, and weakening the occurrence of lipid peroxidation. [ABSTRACT FROM AUTHOR]

Background: Nyctanthes arbor-tristis (NAT) is an ornamental garden plant traditionally used for treating many diseases such as helminthiasis, arthritis, and malaria. Aims: The aim of this study was to validate the ethnobotanical uses of the antimalarial activity of leaves of NAT by in vivo tests. Materials and Methods: Leaves of NAT were identified and authenticated and phytoconstituents of NAT were identified. The antimalarial activity of NAT was studied in in vivo for its schizonticidal activity, repository activity, and curative tests in Swiss albino mice by using Plasmodium berghei (ANKA). Statistical Analysis Used: One-way ANOVA was done for comparison of different groups followed by post hoc analysis (Tukey-Kramer multiple comparison tests). Level of significance was at P < 0.05. Results: The mean schizonticidal activity of NAT increased from 14.21 to 46.15 (P < 0.01) with doses ranging from 100 to 200 mg/kg compared to 67.29 with that of chloroquine (CQ). The repository activity with NAT doses 100–200 mg/kg increased from 12.91 to 42.85 (P < 0.01) compared to 78.79 in pyrimethamine 1.2 mg/kg/day. In Rane's test, there was chemosuppression in range of 55.50–65.02 (P < 0.01) with NAT in doses of 100–200 mg/kg compared to 74.15 with that of CQ 5 mg/kg. Conclusions: The antiplasmodial activity of NAT might be like that of artemisinin by producing oxidative stress mostly due to the iridoid glycosides. The active phytoconstituent(s) responsible may be tested individually or in combination both by in vitro and in vivo studies to identify the active chemical ingredient. [ABSTRACT FROM AUTHOR]

Morindae officinalis Radix (MOR) is a famous traditional Chinese medicine (TCM) and functional food material for invigorating kidneys and tonifying yang. Processed Morindae officinalis Radix (PMOR) is obtained by steaming MOR. Traditionally, the clinical effects are discrepant between processing and nonprocessing herbal medicines. MOR and PMOR are commonly used in both clinical practice and dietary supplements, and the effect of invigorating kidneys and tonifying yang of PMOR is stronger than MOR. To clarify the overall chemical composition and the difference of MOR and PMOR, a method was developed with an ultrahigh-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UHPLC-Q-TOF/MS). Among the 110 identified components shared by MOR and PMOR, 55 compounds showed significant differences in contents. Among them, the contents of 29 components, including fructooligosaccharides, monotropein, deacetylasperulosidic acid, geniposide, and anthraquinone glycosides, were higher in MOR than in PMOR; the contents of 26 components, including difructose anhydride sucrose, and iridoid glycoside derivatives, were higher in PMOR than in MOR. Difructose anhydrides and iridoid glycoside derivatives were first discovered in PMOR. These results provided a scientific basis for research on the therapeutic material basis of MOR. It would provide a method for the comparison of processing and nonprocessing in Chinese medicines.

Objective: The iridoid glycosides were extracted and separated from Osmanthus fragrans seeds, and the potential protective effect of Osmanthus fragrans seed extract on concanavalin A-induced immune liver injury in mice was studied.Methods:Osmanthus fragrans seeds were extracted by 95% ethanol reflux. Then, the iridoid glycosides were enriched by extraction refined through petroleum ether (60°C–90°C), ethyl acetate, and water-saturated n-butanol in sequence, so as to purify the n-butanol part (Osmanthus fragrans seed’s n-butanol extraction, OFSN) by macroporous resin. Specnuezhenide and Nuezhenoside G13 were used as the reference substances to determine the concentration of iridoid glycosides by HPLC. On this basis, a mouse immune liver injury model was established by tail intravenous concanavalin A (20 mg/kg); the contents of serum ALT, AST, IFN-γ, and TNF-α and the contents of liver tissue MDA and SOD were determined; the pathological changes of the liver by HE staining were observed; and the expression levels of p38MAPK and p-p38mapk in liver tissue were detected by WB.Results: The linearity, precision, repeatability, recovery, and stability of HPLC all met the requirements by validating with the methodology. The contents of Specnuezhenide and Nuezhenoside G13 in the n-butanol extracts were 39.20% and 39.88%, respectively. Actually, their contents can reach up to 82.56% and 87.9% after being purified by macroporous resin. The results of animal experiments show that OFSN could significantly reduce the liver and spleen index, reduce the ALT and AST contents in plasma and the MDA content in liver tissue, and then increase the SOD content. Besides, OFSN could also reduce the plasma IFN-γ and TNF-α levels. The HE staining result indicates that the pathological changes in the liver tissues of mice treated with OFSN are alleviated to different degrees while the WB result suggests that OFSN could significantly inhibit the expression of p-p38mapk.Conclusion:Osmanthus fragrans seeds are rich in iridoid glycosides, which has a good protective effect on mouse immune liver injury caused by concanavalin A. The mechanism may be related to inhibiting the phosphorylation of p38MAPK, inhibiting the release of inflammatory mediators, improving the antioxidant capacity of liver cells, and weakening the occurrence of lipid peroxidation.

Since Tang dynasty in China, the fresh leaves of Vaccinium bracteatum (VBL) have been applied as natural pigment to produce black rice. However, detailed information on its biosynthetic mechanism still remained unclear. Following rice dyeing capacity assay, vaccinoside, one of iridoid glycosides, was identified as the key active compound. Increased methodical research demonstrated vaccinoside as a distinct bifunctional precursor, which could be catalyzed by polyphenol oxidase or β-glucosidase independently, followed by reaction with 15 amino acids to give blue pigments (VBPs; λmax 581-590 nm) of different hues. Two synthetic pathways of VBPs were proposed, using multiple techniques such as HPLC, HPSEC, UV-Vis spectrum and colorimeter as analysis tools. Black rice was interpreted to be prepared by cooking, using vaccinoside, intrinsic enzymes from fresh VBL and rice protein in combination. These findings promote the understanding of VBP formation mechanisms and provide an efficient method of producing novel Vaccinium blue pigments., 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 Elsevier Ltd. All rights reserved.)

Herbal medicines are still widely practiced in Kurdistan Region-Iraq, especially by people living in villages on mountainous regions. Among plants belonging to the genus Teucrium (family Lamiaceae), which are commonly employed in the Kurdish traditional medicine, we have analyzed, for the first time, the methanol and aqueous methanol extracts of T. parviflorum aerial parts. The plant is mainly used by Kurds to treat jaundice, liver disorders and stomachache. We aimed to determine the phytochemical profile of the extracts and the structures of the main components, so to provide a scientific rationale for the ancient use of the plant in the ethno-pharmacological field. TLC analysis of the two extracts on silica gel and reversed phase TLC plates, using different visualization systems, indicated similar contents and the presence of phenolics, flavonoids, terpenoids and sugars. The chlorophyll-free extracts exhibited weak/no antimicrobial activities against a panel of bacteria (MICs = 800–1600 µg/mL) and fungal strains (MICs ≥ 5 mg/mL). At the concentration of 600 µg/mL, the methanol extract showed moderate antiproliferative effects against A549 and MCF-7 cancer cell lines in the MTS assay. Moreover, both extracts exhibited a significant dose-dependent free radical scavenging action against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical (EC50 = 62.11 and 44.25 μg/mL, respectively). In a phytochemical study, a high phenolic content (77.08 and 81.47 mg GAE/g dry extract, respectively) was found in both extracts by the Folin–Ciocalteu assay. Medium pressure liquid chromatographic (MPLC) separation of the methanol extract on a reversed phase cartridge eluted with a gradient of MeOH in H2O, afforded two bioactive iridoid glucosides, harpagide (1) and 8-O-acetylharpagide (2). The structures of 1 and 2 were established by spectral data, chemical reactions, and comparison with the literature. Interestingly, significant amounts of hepatotoxic furano neo-clerodane diterpenoids, commonly occurring in Teucrium species, were not detected in the extract. The wide range of biological activities reported in the literature for compounds 1 and 2 and the significant antiradical effects of the extracts give scientific support to the traditional use in Iraqi Kurdistan of T. parviflorum aerial parts for the preparation of herbal remedies.

Five new iridoid glycosides were isolated by chromatographic separation of extracts from the roots of three Gentiana species (Gentianaceae) growing in Eastern Siberia. Their structures were elucidated by spectral methods as 2′-O-(2′′-hydroxy-3′′ -O-β-D-glucopyranosyloxybenzoyl)swertiamarin (gentiridoid A), 2′-O-(2′′-hydroxy-3′′-O-β-D-glucopyranosyloxybenzoyl)gentiopicroside (gentiridoid B), and 3′,6′-di-Oacetyl-4′-O-(2′′,3′′-dihydroxybenzoyl)swertiamarin (gentiridoid C) from G. decumbens L. f.; 2′,3′,6′-tri-Oacetyl-4′-O-[2′′-hydroxy-3′′-O-(6′′′-O-β-D-glucopyranosyl)-β-D-glucopyranosyloxybenzoyl]swertiamarin (gentiridoid D) from G. dahurica Fisch.; and loganic acid 6′-O-(6′′ -O-β-D-glucopyranosyl)-β-Dglucopyranoside (gentiridoid E) from G. macrophylla Pall. [ABSTRACT FROM AUTHOR]

Four previously undescribed iridoid glycosides neocornuside A–D (1–4), along with six known ones (5–10), were isolated from Cornus officinalis fruit. Their structures were elucidated by extensive spectroscopic (NMR, UV, IR, and MS) analysis and comparison with data reported in the literature. All isolates were assessed for their antidiabetic activity on the relative glucose consumption in insulin-induced insulin-resistant HepG2 cells. The results showed that compounds 1, 3, and 7 exhibited significant antidiabetic activities with EC50 values of 0.582, 1.275, and 0.742 μM, respectively. Moreover, compounds 1, 3, and 7 could improve the ability of 2-NBDG uptake of insulin-induced HepG2 cells.

In this study, simultaneous optimization of ultrasound-assistant extraction (UAE) of four representative groups of Osmanthus fragrans (OF) fruit was firstly performed using the response surface methodology (RSM). Subsequently, qualitative and quantitative analysis of irioid glycosides from the optimized OF fruit extract was performed using UPLC-ESI-Orbitrap-MS/MS. A total of 13 irioid glycosides were tentatively identified, of which six compounds were identified for the first time. Finally, the anti-inflammatory activity of the optimized OF var. aurantiacus Makino (OFA) fruit extract was evaluated based on a CuSO4-induced zebra fish model. The biological results demonstrated that OFA fruit extract at a concentration of 5 μg/mL could significantly reduce the number of macrophages, but no significant activities were observed at high concentrations (10 and 50 μg/mL). These results suggest that OF fruit has the promise as a functional additive in food for health promotion.

Increasing demands to reduce fertilizer and pesticide input in agriculture has triggered interest in arbuscular mycorrhizal fungi (AMF) that can enhance plant growth and confer mycorrhiza-induced resistance (MIR). MIR can be based on a variety of mechanisms, including induction of defense compounds, and sensitization of the plant’s immune system (priming) for enhanced defense against later arriving pests or pathogens signaled through jasmonic acid (JA). However, growth and resistance benefits of AMF highly depend on environmental conditions. Low soil P and non-limiting light conditions are expected to enhance MIR, as these conditions favor AMF colonization and because of observed positive cross-talk between the plant’s phosphate starvation response (PSR) and JA-dependent immunity. We therefore tested growth and resistance benefits of the AMF Funneliformis mosseae in Plantago lanceolata plants grown under different levels of soil P and light intensity. Resistance benefits were assessed in bioassays with the leaf chewing herbivore Mamestra brassicae. Half of the plants were induced by jasmonic acid prior to the bioassays to specifically test whether AMF primed plants for JA-signaled defense under different abiotic conditions. AMF reduced biomass production but contrary to prediction, this reduction was not strongest under conditions considered least optimal for carbon-for-nutrient trade (low light, high soil P). JA application induced resistance to M. brassicae, but its extent was independent of soil P and light conditions. Strikingly, in younger plants, JA-induced resistance was annulled by AMF under high resource conditions (high soil P, ample light), indicating that AMF did not prime but repressed JA-induced defense responses. In older plants, low soil P and light enhanced susceptibility to M. brassicae due to enhanced leaf nitrogen levels and reduced leaf levels of the defense metabolite catalpol. By contrast, in younger plants, low soil P enhanced resistance. Our results highlight that defense priming by AMF is not ubiquitous and calls for studies revealing the causes of the increasingly observed repression of JA-mediated defense by AMF. Our study further shows that in our system abiotic factors are significant modulators of defense responses, but more strongly so by directly modulating leaf quality than by modulating the effects of beneficial microbes on resistance.

Gardeniae Fructus, the dry fruit of Gardenia jasminoides Ellis, has been widely used for the treatment of different diseases. Although four types of processed Gardeniae Fructus products, characterized by differing effects, are available for clinical use, little is known regarding the respective processing mechanisms. In this study, ultra‐high‐performance liquid chromatography quadrupole time‐of‐flight mass spectrometry combined with multivariate statistical analysis was applied to characterize the chemical profiles of the differently processed Gardeniae Fructus products and to determine differences in their chemical compositions, thereby enabling us to identify those active compounds associated with the observed clinical effects. A total of 125 compounds were accordingly identified, among which, 56 were established as primary contributors to the significant differences (P < 0.01) between crude and processed Gardeniae Fructus, based on t‐test analysis. Furthermore, the potential mechanisms underlying the chemical transformations that occurred during processing were discussed. The findings of this study may not only contribute to the more effective quality control of Gardeniae Fructus but also provide basic information for elucidating the mechanisms underlying the changes in chemical constituents in response to processing, and provide a basis for further investigations of Gardeniae Fructus processing mechanisms. [ABSTRACT FROM AUTHOR]

Three iridoid glycosides, 5-allosyloxy-aucubine (1), melittoside (2), ajugol (3), five phenylethanoid glycosides, verbascoside (4), martynoside (5), leucoseptoside A (6), lamalboside (7), decaffeoylverbascoside (8), four flavonoids, xanthomicrol (9), isoscutellarein 7-O-[6'''-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (10), 4'-O-methylisoscutellarein 7-O-[6'''-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (11), 3'-hydroxy-4'-O-methylisoscutellarein 7-O-[6'''-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (12), and two lignan glycosides dehydrodiconiferylalcohol 4-O-β-D-glucopyranose (13) and pinoresinol 4'-O-β-glucopyranoside (14) were isolated from the aerial parts of Sideritis germanicopolitana. Their structures were determined on the basis of detailed NMR and HRESIMS analyses. To our knowledge, all compounds are being reported for the first time from S. germanicopolitana, while the isolated lignans (13 and 14) are new for the genus Sideritis. In vitro evaluation of AChE, BChE and LOX inhibitory effects of all the tested compounds (1–14) resulted in low to moderate activities. [ABSTRACT FROM AUTHOR]