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1.
J Nanobiotechnology ; 22(1): 206, 2024 Apr 24.
Article in English | MEDLINE | ID: mdl-38658950

ABSTRACT

The insufficient abundance and weak activity of tumour-infiltrating lymphocytes (TILs) are two important reasons for the poor efficacy of PD-1 inhibitors in hepatocellular carcinoma (HCC) treatment. The combined administration of tanshinone IIA (TSA) and astragaloside IV (As) can up-regulate the abundance and activity of TILs by normalising tumour blood vessels and reducing the levels of immunosuppressive factors respectively. For enhancing the efficacy of PD-1 antibody, a magnetic metal-organic framework (MOF) with a homologous tumour cell membrane (Hm) coating (Hm@TSA/As-MOF) is established to co-deliver TSA&As into the HCC microenvironment. Hm@TSA/As-MOF is a spherical nanoparticle and has a high total drug-loading capacity of 16.13 wt%. The Hm coating and magnetic responsiveness of Hm@TSA/As-MOF provide a homologous-magnetic dual-targeting, which enable Hm@TSA/As-MOF to counteract the interference posed by ascites tumour cells and enhance the precision of targeting solid tumours. Hm coating also enable Hm@TSA/As-MOF to evade immune clearance by macrophages. The release of TSA&As from Hm@TSA/As-MOF can be accelerated by HCC microenvironment, thereby up-regulating the abundance and activity of TILs to synergistic PD-1 antibody against HCC. This study presents a nanoplatform to improve the efficacy of PD-1 inhibitors in HCC, providing a novel approach for anti-tumour immunotherapy in clinical practice.


Subject(s)
Carcinoma, Hepatocellular , Liver Neoplasms , Metal-Organic Frameworks , Programmed Cell Death 1 Receptor , Metal-Organic Frameworks/chemistry , Metal-Organic Frameworks/pharmacology , Liver Neoplasms/drug therapy , Carcinoma, Hepatocellular/drug therapy , Animals , Mice , Humans , Programmed Cell Death 1 Receptor/antagonists & inhibitors , Cell Line, Tumor , Immune Checkpoint Inhibitors/pharmacology , Tumor Microenvironment/drug effects , Mice, Inbred BALB C , Saponins/pharmacology , Saponins/chemistry , Lymphocytes, Tumor-Infiltrating/drug effects , Lymphocytes, Tumor-Infiltrating/immunology
2.
World J Microbiol Biotechnol ; 40(5): 152, 2024 Mar 30.
Article in English | MEDLINE | ID: mdl-38553646

ABSTRACT

Saponins are a large group of compounds, produced mostly by plants as a side product of their metabolic activity. These compounds have attracted much attention over the years mostly because of their surface activity and antibacterial, anti-inflammatory and antifungal properties. On the other hand, most of the hitherto research has concerned the action of saponins against microbial cells as a whole. Therefore, knowing the possible interaction of saponins with biomembrane, we decided to check in-vitro the influence of saponin-rich extract of Saponaria officinalis on spheroplasts of two Candida sp. The obtained results show that 10 mg L- 1 of extract increased the permeability of spheroplasts up to 21.76% relative to that of the control sample. Moreover, the evaluation of surface potential has revealed a decrease by almost 10 mV relative to that of the untreated samples. Such results suggest its direct correlation to integration of saponins into the biomembrane structure. The obtained results have proved the antifungal potential of saponins and their ability of permeabilization of cells. This proves the high potential of saponins use as additives to antifungal pharmaceutics, which is expected to lead to improvement of their action or reduction of required dosage.


Subject(s)
Saponaria , Saponins , Antifungal Agents/pharmacology , Antifungal Agents/chemistry , Saponaria/chemistry , Saponins/pharmacology , Saponins/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Candida , Permeability
3.
Food Chem ; 448: 138959, 2024 Aug 01.
Article in English | MEDLINE | ID: mdl-38552464

ABSTRACT

This study aimed to investigate the interaction between L.casei and L.bulgaricus with Polygonatum sibiricum saponins (PSS) and to explore the co-microencapsulation to reduce their loss rate during storage and consumption. 1% PSS was added to the culture broth, and it was found that the growth and metabolism of the strains were accelerated, especially in the compound probiotic group, indicating that PSS has potential for prebiotics. LC-MS observed significant differences in the composition and content of saponins in PSS. The metabolomics results suggest that the addition of PSS resulted in significant changes in the metabolites of probiotics. In addition, it was found that the combination of probiotics and PSS may have stronger hypoglycemic ability (ɑ-glucosidase, HepG2). Finally, a co-microencapsulated delivery system was constructed using zein and isomaltooligosaccharide. This system can achieve more excellent resistance of probiotics and PSS in gastrointestinal fluids, effectively transporting both to the small intestine.


Subject(s)
Drug Compounding , Polygonatum , Probiotics , Saponins , Saponins/chemistry , Saponins/metabolism , Saponins/pharmacology , Humans , Probiotics/metabolism , Probiotics/chemistry , Polygonatum/chemistry , Polygonatum/metabolism , Prebiotics/analysis , Lactobacillus/metabolism , Lactobacillus/chemistry , Lactobacillus/growth & development , Lactobacillales/metabolism , Lactobacillales/growth & development , Lactobacillales/chemistry
4.
Molecules ; 29(6)2024 Mar 14.
Article in English | MEDLINE | ID: mdl-38542930

ABSTRACT

Rhizoma Panacis Japonici (RPJ) is an ancient herbal medicine from China that has long been employed for its medicinal benefits in relieving arthritis physical debility and diverse afflictions. The primary bioactive constituents found in RPJ are triterpene saponins, which exhibit numerous pharmacological actions, including anti-inflammatory, antioxidant, and immunomodulating effects. The present study established a straightforward and effective approach for characterizing triterpene saponins in RPJ. An offline HILIC × RP LC/QTOF-MS method was developed, along with a self-constructed in-house database containing 612 saponins reported in the Panax genus and 228 predicted metabolites. The approach achieved good chromatographic performance in isolating triterpene saponins of RPJ, with the HILIC column as the first dimension (1D) and the BEH C18 column as the second dimension (2D). The developed two-dimensional liquid chromatography system exhibited an orthogonality of 0.61 and a peak capacity of 1249. Detection was performed using a QTOF mass spectrometer in a data-independent manner (MSE) in a negative ion mode. Using the in-house database, the collected MS data were processed by an automatic workflow on UNIFI 1.8.2 software, which included data correction, matching of precursor and product ions, and peak annotation. In this study, 307 saponins were characterized from RPJ and 76 saponins were identified for the first time in Panax japonicus. This research not only enhances our understanding of the chemical characteristics of RPJ but also offers a simple and efficient method for analyzing the complex composition of herbal medicine.


Subject(s)
Drugs, Chinese Herbal , Panax , Plants, Medicinal , Saponins , Triterpenes , Saponins/chemistry , Triterpenes/chemistry , Chromatography, High Pressure Liquid/methods , Plant Extracts/chemistry , Mass Spectrometry , Plants, Medicinal/chemistry
5.
Molecules ; 29(6)2024 Mar 15.
Article in English | MEDLINE | ID: mdl-38542951

ABSTRACT

The fruits of Solanum torvum Swartz, a wild relative of eggplant, are consumed as a wild vegetable in tropical regions of Africa, Asia, and South America. In traditional Chinese medicine, it is believed to have anti-inflammatory and sedative effects. In the Philippines, water decoction is used to treat hyperactivity disorder. Twenty-two steroidal saponins were isolated and purified from the fruits grown in Yunnan, China, including six new compounds: torvosides U-Z (1-6). During drying and cooking, the saponins may undergo transformation, resulting in small amounts of sapogenins. These transformations can include dehydration of hydroxyl groups at position C22, formation of double bonds at position 20, 22 or 22, 23, and even formation of peroxide products. Saponin compounds torvoside X (4), torvoside Y (5), torvoside A (7), and (25S)-3-oxo-5α-spirostan-6α-yl-O-ß-d-xylopyranoside (20), which are glycosylated at C-6, showed certain anti-epileptic activity in a pentylenetetrazole-induced zebrafish seizure model. No antiproliferative activity was detected when tested on the cancer cell line HepG2, and no hepatotoxic effect was noted on normal liver cell line LO2.


Subject(s)
Saponins , Solanum melongena , Solanum , Animals , Solanum/chemistry , Fruit/chemistry , Zebrafish , Pentylenetetrazole , China , Saponins/chemistry , Anticonvulsants/pharmacology , Anticonvulsants/analysis , Seizures/chemically induced , Seizures/drug therapy
6.
J Ethnopharmacol ; 328: 118080, 2024 Jun 28.
Article in English | MEDLINE | ID: mdl-38521426

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: The use of antineoplastic drugs, such as cisplatin, in clinical practice can cause adverse effects in patients, such as liver injury, which limits their long-term use. Therefore, there is an urgent need to develop alternative therapeutic strategies or drugs to minimize cisplatin-induced liver injury. Huangqi, the root of Astragalus membranaceus, is extensively used in traditional Chinese medicine (TCM) and has been employed in treating diverse liver injuries. Astragalus membranaceus contains several bioactive constituents, including triterpenoid saponins, one of which, astragaloside IV (ASIV), has been reported to have anti-inflammatory and antioxidant stress properties. However, its potential in ameliorating cisplatin-induced liver injury has not been explored. AIM OF THE STUDY: The objective of this study was to examine the mechanism by which ASIV protects against cisplatin-induced liver injury. MATERIALS AND METHODS: This study established a model of cisplatin-induced liver injury in mice, followed by treatment with various doses of astragaloside IV (40 mg/kg, 80 mg/kg). In addition, a model of hepatocyte ferroptosis in AML-12 cells was established using RSL3. The mechanism of action of astragaloside IV was investigated using a range of methods, including Western blot assay, qPCR, immunofluorescence, histochemistry, molecular docking, and high-content imaging system. RESULTS: The findings suggested a significant improvement in hepatic injury, inflammation and oxidative stress phenotypes with the administration of ASIV. Furthermore, network pharmacological analyses provided evidence that a major pathway for ASIV to attenuate cisplatin-induced hepatic injury entailed the cell death cascade pathway. It was observed that ASIV effectively inhibited ferroptosis both in vivo and in vitro. Subsequent experimental outcomes provided further validation of ASIV's ability to hinder ferroptosis through the inhibition of PPARα/FSP1 signaling pathway. The current findings suggest that ASIV could function as a promising phytotherapy composition to alleviate cisplatin-induced liver injury. CONCLUSIONS: The current findings suggest that astragaloside IV could function as a promising phytotherapy composition to alleviate cisplatin-induced liver injury.


Subject(s)
Chemical and Drug Induced Liver Injury, Chronic , Ferroptosis , Saponins , Triterpenes , Humans , Mice , Animals , Cisplatin/toxicity , Molecular Docking Simulation , Chemical and Drug Induced Liver Injury, Chronic/drug therapy , Saponins/pharmacology , Saponins/therapeutic use , Saponins/chemistry , Triterpenes/pharmacology , Triterpenes/therapeutic use , Triterpenes/chemistry
7.
Se Pu ; 42(3): 234-244, 2024 Mar 08.
Article in Chinese | MEDLINE | ID: mdl-38503700

ABSTRACT

Ziziphi Spinosae Semen refers to the dried seed of Ziziphus jujuba Mill. var. spinosa (Bunge) Hu ex H. F. Chou. The seed is composed of a reddish brown coat and a yellow kernel. A comparative study was conducted to investigate differences in the chemical composition and their relative contents between the seed coat and kernel of Ziziphi Spinosae Semen. First, the chemical compounds found in the seed coat and kernel were characterized and identified using ultra performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF/MS). The analytical results tentatively identified 57 chemical compounds based on reference-compound comparison, literature retrieval, and chemical-database (e. g., MassBank) searches; these compounds included 14 triterpenes, 23 flavonoids, 7 alkaloids, 6 carboxylic acids, and 7 other types of compounds. The mass error of the identified compounds was within the mass deviation range of 5×10-6 (5 ppm). Next, two methods of multivariate statistical analysis, namely, principal component analysis (PCA) and orthogonal partial least squares-discriminant analysis (OPLS-DA), were used to compare the differential compounds between the two seed parts. A total of 17 differential compounds were screened out via OPLS-DA based on a variable importance in projection (VIP) value of >5. The results revealed that betulinic acid, betulonic acid, alphitolic acid, and jujuboside Ⅰ mainly existed in the seed coat whereas the 13 other compounds, such as spinosin, jujuboside A, and 6‴-feruloylspinosin, mainly existed in the seed kernel. Therefore, these 17 differential compounds can be used to distinguish between the two seed parts. Finally, a semiquantitative method was established using UPLC and a charged aerosol detector (CAD) with inverse gradient compensation in the mobile phase. Six representative compounds with different types were selected to examine the CAD response consistency: magnoflorine (alkaloid), spinosin (flavone), 6‴-feruloylspinosin (flavone), jujuboside A (triterpenoid saponin), jujuboside B (triterpenoid saponin), and betulinic acid (triterpenoid acid). The results showed that the relative standard deviation (RSD) of the average response factors at different levels of these six compounds was 7.04% and that their response intensities were similar. Moreover, each compound in the fingerprint demonstrated good response consistency, and the peak areas obtained directly reflected the contents of each compound. Based on the semiquantitative fingerprints obtained, betulinic acid and oleic acid were considered the main components of the seed coat. The betulinic acid content in the seed coat was approximately 7 times higher than that in the seed kernel. Spinosin, jujuboside A, linoleic acid, betulinic acid, and oleic acid were the main components of the seed kernel. The spinosin content in the seed kernel was 18 times higher than that in the seed coat. In addition, the jujuboside A content in the seed kernel was 24 times higher than that in the seed coat. The proposed method can accurately determine the main components and compare the relative contents of these components in different seed parts. In summary, this study identified the differences in chemical components between the seed coat and kernel of Ziziphi Spinosae Semen and clarified the main components and their relative contents in these parts. The findings can not only provide a basis for the identification of chemical compounds and quality research on different parts of Ziziphi Spinosae Semen but also promote the development and utilization of this traditional Chinese medicine.


Subject(s)
Alkaloids , Drugs, Chinese Herbal , Flavones , Saponins , Triterpenes , Ziziphus , Drugs, Chinese Herbal/chemistry , Betulinic Acid , Saponins/chemistry , Oleic Acids , Chromatography, High Pressure Liquid , Ziziphus/chemistry , Seeds
8.
Phytochemistry ; 221: 114049, 2024 May.
Article in English | MEDLINE | ID: mdl-38462214

ABSTRACT

Six undescribed triterpenoid saponins, namely aescuchinosides A-F, along with seven known triterpenoid saponins, were isolated from the seeds of Aesculus chinensis. Barrigenol-like triterpenoids (BATs) constitute these saponins. Protoaescigenin serves as their aglycone, with various oxygen-containing groups, including acetyl, isobutyryl, tigloyl, and angeloyl groups situated at C-21, C-22, and C-28. Various techniques, including 1D and 2D-NMR spectroscopy, high-resolution mass spectrometry, and acid hydrolysis, were employed to determine the structures of these compounds. The antihyperglycemic effects of the isolated compounds were examined in insulin -resistant HepG2 cells induced by palmitic acid treatment. At a concentration of 6 µM, aesculinoside F exhibited a significant increase in glucose consumption. In addition, aesculinoside F demonstrated the potential to improve insulin resistant by upregulating the PI3K/AKT pathway. These results indicate that the seeds of A.chinensis hold promising potential for preventing insulin resistant related disease.


Subject(s)
Aesculus , Saponins , Triterpenes , Aesculus/chemistry , Phosphatidylinositol 3-Kinases , Triterpenes/pharmacology , Triterpenes/chemistry , Seeds/chemistry , Saponins/pharmacology , Saponins/chemistry , Insulin , Hypoglycemic Agents/pharmacology
9.
J Chem Ecol ; 50(3-4): 168-184, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38443712

ABSTRACT

Many plant species, particularly legumes, protect themselves with saponins. Previously, a correlation was observed between levels of oleanolic acid-derived saponins, such as hederagenin-derived compounds, in the legume Medicago truncatula and caterpillar deterrence. Using concentrations that reflect the foliar levels of hederagenin-type saponins, the sapogenin hederagenin was not toxic to 4th instar caterpillars of the cabbage looper Trichoplusia ni nor did it act as a feeding deterrent. Female caterpillars consumed more diet than males, presumably to obtain the additional nutrients required for oogenesis, and are, thus, exposed to higher hederagenin levels. When fed the hederagenin diet, male caterpillars expressed genes encoding trypsin-like proteins (LOC113500509, LOC113501951, LOC113501953, LOC113501966, LOC113501965, LOC113499659, LOC113501950, LOC113501948, LOC113501957, LOC113501962, LOC113497819, LOC113501946, LOC113503910) as well as stress-responsive (LOC113503484, LOC113505107) proteins and cytochrome P450 6B2-like (LOC113493761) at higher levels than females. In comparison, female caterpillars expressed higher levels of cytochrome P450 6B7-like (LOC113492289). Bioinformatic tools predict that cytochrome P450s could catalyze the oxygenation of hederagenin which would increase the hydrophilicity of the compound. Expression of a Major Facilitator Subfamily (MFS) transporter (LOC113492899) showed a hederagenin dose-dependent increase in gene expression suggesting that this transporter may be involved in sapogenin efflux. These sex-related differences in feeding and detoxification should be taken into consideration in insecticide evaluations to minimize pesticide resistance.


Subject(s)
Moths , Oleanolic Acid , Oleanolic Acid/analogs & derivatives , Saponins , Transcriptome , Animals , Female , Male , Saponins/metabolism , Saponins/chemistry , Oleanolic Acid/metabolism , Oleanolic Acid/pharmacology , Oleanolic Acid/chemistry , Moths/drug effects , Moths/physiology , Moths/genetics , Transcriptome/drug effects , Larva/drug effects , Larva/genetics , Sex Characteristics
10.
Zhongguo Zhong Yao Za Zhi ; 49(2): 304-314, 2024 Jan.
Article in Chinese | MEDLINE | ID: mdl-38403306

ABSTRACT

Minor ginsenosides are a class of processed saponins with minor natural content, high bioavailability, and outstanding bio-logical activity, which are usually obtained by biological or chemical transformation of prototype saponins directly extracted from Panax plants. In recent years, with the clarification of the biosynthetic pathway of saponins and the development of synthetic biology, it has become possible to use synthetic metabolic engineering methods with microorganisms as hosts to produce saponins. Minor ginsenosides have received widespread attention because of their remarkable biological activities in enhancing the immune function of the body and antitumor property. At present, most of the reviews on minor ginsenosides focus on transformation preparation, process optimization, and pharmacological activity, but there are some deficiencies in industrial analysis. This study summarized structural types, pharmacological activities, sources of acquisition, and transformation pathways of minor ginsenosides based on the relevant literature in China and abroad, proposed problems in the preparation of existing minor ginsenosides, and discussed the future research and utilization prospects, to provide a theoretical basis for improving the basic research of minor ginsenosides and promoting their industrialization.


Subject(s)
Ginsenosides , Panax , Saponins , Ginsenosides/chemistry , Saponins/chemistry , Panax/chemistry , Biosynthetic Pathways , Synthetic Biology
11.
J Agric Food Chem ; 72(9): 4596-4609, 2024 Mar 06.
Article in English | MEDLINE | ID: mdl-38385330

ABSTRACT

To discover new botanical products-based insecticide candidates, 14 triterpenoid saponins (1-14) including four new ones, obscurosides A-D (1-4), were isolated from Clematis obscura Maxim as potential agrochemicals against Acyrthosiphon pisum Harris and Plutella xylostella (L.). Compounds 1-3 were characterized by a rare ribose substitution at C-3, and 4 was a bidesmoside glycosylated at the rare C-23 and C-28 positions of the oleanane aglycone. Compounds 10 (median antifeeding concentration, AFC50 = 1.10 mg/mL; half-lethal concentration, LC50 = 1.21 mg/mL) and 13 (AFC50 = 1.09 mg/mL, LC50 = 1.37 mg/mL) showed significant insecticidal activities against third larvae of P. xylostella at 72 h. All saponins displayed antifeedant activities against A. pisum with the deterrence index of 0.20-1.00 at 400 µg/mL. Compound 8 showed optimal oral toxicity (LC50 = 50.09 µg/mL) against A. pisum, followed by compounds 1, 5-7, 9, and 14 (LC50 = 90.21-179.25 µg/mL) at 72 h. The shrinkage of the cuticle and the destruction of intestinal structures of microvilli, nucleus, endoplasmic reticulum, and mitochondria were toxic symptoms of 8-treated A. pisum. The significantly declined Chitinase activity in 8-treated A. pisum with an inhibition rate of 79.1% at LC70 (70% lethal concentration) could be the main reason for its significant oral toxicities. Molecular docking revealed favorable affinities of compounds 1 and 8 with group I Chitinase OfChtI (Group I Chitinase from Ostrinia furnacalis) through conventional hydrogen bonds and alkey/π-alkey interactions by different patterns. These results will provide valuable information for the development of novel botanical pesticides for the management of insect pests, especially against A. pisum.


Subject(s)
Aphids , Chitinases , Clematis , Insecticides , Moths , Saponins , Animals , Insecticides/chemistry , Saponins/chemistry , Clematis/chemistry , Peas , Molecular Docking Simulation , Larva
12.
J Agric Food Chem ; 72(9): 4574-4586, 2024 Mar 06.
Article in English | MEDLINE | ID: mdl-38385335

ABSTRACT

Extensive research has been conducted on Camellia oleifera Abel., a cultivar predominantly distributed in China, to investigate its phytochemical composition, owning to its potential as an edible oil crop. Pentacyclic triterpene saponins, as essential active constituents, play a significant role in contributing to the pharmacological effects of this cultivar. The saponins derived from C. oleifera (CoS) offer a diverse array of bioactivity benefits, including antineoplastic/bactericidal/inflammatory properties, cardiovascular protection, neuroprotection, as well as hypoglycemic and hypolipidemic effects. This review presents a comprehensive analysis of the isolation and pharmacological properties of CoS. Specially, we attempt to reveal the antitumor structure-activity relationship (SAR) of CoS-derived triterpenoids. The active substitution sites of CoS, namely, C-3, C-15, C-16, C-21, C-22, C-23, and C-28 pentacyclic triterpenoids, make it a unique and highly valuable substance with significant medicinal and culinary applications. As such, CoS can play a critical role in transforming people's lives, providing unique medicinal benefits, and contributing to the advancement of both medicine and cuisine.


Subject(s)
Camellia , Saponins , Triterpenes , Humans , Triterpenes/chemistry , Camellia/chemistry , Structure-Activity Relationship , Seeds/chemistry , Saponins/pharmacology , Saponins/chemistry
13.
Bioorg Chem ; 145: 107230, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38387397

ABSTRACT

Historically, Astragalus membranaceus Bunge has been used as a beneficial medicinal plant, particularly in the Asian traditional medical systems, for the treatment of various human diseases such as stomach ulcers, diarrhea, and respiratory issues associated with phlegm. In this study, a phytochemical characterization of the aerial parts of A. membranaceusled to the isolation of 29 oleanane-type triterpenoid saponins, including 11 new compounds named astraoleanosides E-P (6-9, 13, 14, 18-22), as well as 18 known ones. The structures of these compounds were elucidated using nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry. Among them, astraoleanoside H (9) and cloversaponin III (15) demonstrated the most potent ß-glucuronidase inhibitory activities, with IC50 values of 21.20 ± 0.75 and 9.05 ± 0.47 µM, respectively, compared to the positive control d-saccharic acid 1,4-lactone (IC50 = 20.62 ± 1.61 µM). Enzyme kinetics studies were then conducted to investigate the type of inhibition exhibited by these active compounds. In addition, the binding mechanism, key interactions, binding stability, and dynamic behavior of protein-ligand complexes were investigated through in silico approaches, such as molecular docking and molecular dynamics simulations. These findings highlight the promising potential of triterpenoid saponins from A. membranaceus as lead compounds for ß-glucuronidase inhibitors, offering new possibilities for the development of therapeutic agents targeting various diseases where ß-glucuronidase plays a crucial role.


Subject(s)
Oleanolic Acid , Oleanolic Acid/analogs & derivatives , Saponins , Triterpenes , Humans , Molecular Structure , Astragalus propinquus/chemistry , Molecular Docking Simulation , Saponins/chemistry , Oleanolic Acid/chemistry , Plant Components, Aerial/chemistry , Triterpenes/pharmacology , Triterpenes/chemistry
14.
Planta Med ; 90(5): 397-410, 2024 May.
Article in English | MEDLINE | ID: mdl-38365219

ABSTRACT

Agave applanata is a Mexican agave whose fresh leaves are employed to prepare an ethanol tonic used to relieve diabetes. It is also applied to skin to relieve varicose and diabetic foot ulcers, including wounds, inflammation, and infections. In this study, the chemical composition of this ethanol tonic is established and its association with antihyperglycemic, anti-inflammatory, antimicrobial, and wound healing activities is discussed. The fresh leaves of A. applanata were extracted with ethanol : H2O (85 : 15). A fraction of this extract was lyophilized, and the remainder was partitioned into CH2Cl2, n-BuOH, and water. CH2Cl2 and n-BuOH fractions were subjected to a successive open column chromatography process. The structure of the isolated compounds was established using nuclear magnetic resonance and mass spectrometry spectra. The antihyperglycemic activity was evaluated through in vivo sucrose and glucose tolerance experiments, as well as ex vivo intestinal absorption and hepatic production of glucose. Wound healing and edema inhibition were assayed in mice. The minimum inhibitory concentrations (MICs) of the hydroalcoholic extract, its fractions, and pure compounds were determined through agar microdilution against the most isolated pathogens from diabetic foot ulcers. Fatty acids, ß-sitosterol, stigmasterol, hecogenin (1: ), N-oleyl-D-glucosamine, ß-daucosterol, sucrose, myo-inositol, and hecogenin-3-O-α-L-rhamnopyranosyl-(1 → 3)-ß-D-xylopyranosyl-(1 → 2)-[ß-D-xylopyranosyl-(1 → 3)-ß-D-glucopyranosyl-(1 → 3)]-ß-D-glucopyranosyl-(1 → 4)-ß-D-galactopyranoside (2: ) were characterized. This research provides evidence for the pharmacological importance of A. applanata in maintaining normoglycemia, showing anti-inflammatory activity and antimicrobial effects against the microorganisms frequently found in diabetic foot ulcers. This plant plays an important role in wound healing and accelerated tissue reparation.


Subject(s)
Agave , Diabetic Foot , Sapogenins , Saponins , Mice , Animals , Agave/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Saponins/chemistry , Hypoglycemic Agents/pharmacology , Anti-Inflammatory Agents/pharmacology , Ethanol , Wound Healing , Glucose , Sucrose
15.
Fitoterapia ; 174: 105858, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38365071

ABSTRACT

The abundance of saponin-rich plants across different ecosystems indicates their great potential as a replacement for harmful synthetic surfactants in modern commercial products. These organic saponins have remarkable biological and surface-active properties and align with sustainable and eco-friendly practices. This article examines and discusses the structure and properties of plant saponins with high yield of saponin concentrations and their exploitable applications. This highlights the potential of saponins as ethical substitutes for traditional synthetic surfactants and pharmacological agents, with favorable effects on the economy and environment. For this purpose, studies on the relevant capabilities, structure, and yield of selected plants were thoroughly examined. Studies on the possible uses of the selected saponins have also been conducted. This in-depth analysis highlights the potential of saponins as workable and ethical replacements for traditional synthetic medications and surfactants, thus emphasizing their favorable effects on human health and the environment.


Subject(s)
Ecosystem , Saponins , Humans , Molecular Structure , Plant Extracts , Saponins/chemistry , Surface-Active Agents/chemistry
16.
Org Biomol Chem ; 22(10): 2081-2090, 2024 03 06.
Article in English | MEDLINE | ID: mdl-38363172

ABSTRACT

The spirostanol saponin gitonin was efficiently synthesized in 12 steps (longest linear sequence) in 18.5% overall yield from the commercially available isopropyl ß-D-1-thiogalactopyranoside (IPTG) and tigogenin. A cascade two-step glycosylation and Schmidt's inverse procedure significantly facilitated the synthesis of gitonin and its derivatives. The cytotoxic activities of gitonin and its structural analogues were evaluated against A549, HepG2, and MCF-7, and most of them exhibited moderate to excellent inhibitory activity. Our study demonstrates that the removal of the ß-D-galactopyranosyl residue (attached at C-2 of the glucose unit) from gitonin would not decrease the inhibition activities; however, further cleavage of sugar units could seriously reduce the activities. A bioassay on these cancer cell lines also suggested that the presence of 2α-hydroxy on the aglycone weakened the cytotoxicity of the designed saponin.


Subject(s)
Antineoplastic Agents , Saponins , Spirostans , Saponins/chemistry , Molecular Structure , Digitalis Glycosides , Antineoplastic Agents/pharmacology , Spirostans/pharmacology , Cell Line, Tumor
17.
Int J Mol Sci ; 25(3)2024 Feb 05.
Article in English | MEDLINE | ID: mdl-38339223

ABSTRACT

Aralia elata (Miq.) Seem is a medicinal plant that shares a common pathway for the biosynthesis of triterpenoid saponins with Panax ginseng. Here, we transferred the dammarenediol-II synthase gene from P. ginseng (PgDDS; GenBank: AB122080.1) to A. elata. The growth of 2-year-old transgenic plants (L27; 9.63 cm) was significantly decreased compared with wild-type plants (WT; 74.97 cm), and the leaflet shapes and sizes of the transgenic plants differed from those of the WT plants. Based on a terpene metabolome analysis of leaf extracts from WT, L13, and L27 plants, a new structural skeleton for ursane-type triterpenoid saponins was identified. Six upregulated differentially accumulated metabolites (DAMs) were detected, and the average levels of Rg3 and Re in the leaves of the L27 plants were 42.64 and 386.81 µg/g, respectively, increased significantly compared with the WT plants (15.48 and 316.96 µg/g, respectively). Thus, the expression of PgDDS in A. elata improved its medicinal value.


Subject(s)
Aralia , Plants, Medicinal , Saponins , Triterpenes , Aralia/genetics , Aralia/chemistry , Saponins/chemistry , Triterpenes/chemistry , Plants, Medicinal/metabolism , Plants, Genetically Modified/genetics , Plants, Genetically Modified/metabolism , Plant Leaves/metabolism
18.
Fitoterapia ; 174: 105833, 2024 Apr.
Article in English | MEDLINE | ID: mdl-38301935

ABSTRACT

Five new steroidal saponins, paripolins D-H (1-5), and 6 known compounds (6-11) were isolated from the aerial parts of Paris polyphylla var. yunnanensis. The structures of 1-5 were determined using spectroscopic analyses in conjunction with acid hydrolysis. It is for the first time to report the 12-hydroxysteroidal saponins from the genus Paris. The effect of all isolated compounds on blood coagulation was determined in vitro using the plasma recalcification time method. Compounds 1 and 2 showed potent procoagulant activity, and 5-11 exhibited significant anticoagulant activity.


Subject(s)
Liliaceae , Saponins , Liliaceae/chemistry , Rhizome/chemistry , Molecular Structure , Saponins/pharmacology , Saponins/chemistry , Blood Coagulation
19.
Phytochemistry ; 219: 113994, 2024 Mar.
Article in English | MEDLINE | ID: mdl-38244959

ABSTRACT

Five undescribed compounds, including two cholestane glycosides parispolyosides A and E, and three spirostanol glycosides parispolyosides B-D, were isolated from rhizome of Paris polyphylla var. chinensis (Franch.) Hara, together with twenty-one known steroidal saponins. Their chemical structures were elucidated on the basis of comprehensive analysis of 1D and 2D NMR, as well as HR-ESI-MS spectroscopic data. Two of these compounds demonstrated potent inhibitory effect on NO production stimulated by lipopolysaccharide in raw 264.7 cells with IC50 values of 61.35 µM and 37.23 µM. Four compounds exhibited moderate inhibitory activity against HepG2 cells with IC50 values ranging from 9.43 to 24.54 µM. Molecular docking analysis revealed that the potential mechanism of NO inhibition by the active compounds was associated with the interactions with iNOS protein.


Subject(s)
Antineoplastic Agents , Liliaceae , Saponins , Rhizome/chemistry , Molecular Docking Simulation , Saponins/chemistry , Liliaceae/chemistry , Anti-Inflammatory Agents/pharmacology
20.
Int J Biol Macromol ; 260(Pt 2): 129511, 2024 Mar.
Article in English | MEDLINE | ID: mdl-38242391

ABSTRACT

Since ancient times, Polygonatum Mill. (Asparagaceae) has been utilized as a medicinal and culinary resource in China. Its efficacy in treating various illnesses has been well documented. Traditional processing involves the Nine-Steam-Nine-Bask method, which results in a reduction of toxicity and enhanced effectiveness of Polygonatum. Many substances, such as polysaccharides, lignins, saponins, homoisoflavones, alkaloids, and others, have been successfully isolated from Polygonatum. This review presents the research progress on the chemical composition of three crude and processed Polygonatum, including Polygonatum sibiricum Redouté (P. sibiricum), Polygonatum kingianum Collett & Hemsl (P. kingianum), and Polygonatum cyrtonema Hua (P. cyrtonema). The review also includes the pharmacology of Polygonatum, specifically on the pharmacology of polysaccharides both before and after processing. Its objective is to provide a foundation for uncovering the significance of the processing procedure, and to facilitate the development and utilization of Polygonatum in clinical practice.


Subject(s)
Asparagaceae , Polygonatum , Saponins , Polygonatum/chemistry , Lignin , Polysaccharides/chemistry , Saponins/chemistry
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