Phytochemical investigation of aerial parts of Woodsia ilvensis and its plasmin-inhibitory activity in vitro.

The fern plant Woodsia ilvensis (L.) R. Br. belongs to the Woodsiaceae family and its leaves are used to treat diarrhea, soft-tissue injuries, and external injuries. Investigations of the compounds obtained from the plasmin-inhibitory-active extracts of W. ilvensis led to the isolation of two undescribed maleimide N-glycosides, an undescribed stilbenoid glycoside, and five undescribed acetylated flavonol bisdesmosides, together with 19 known compounds. The chemical structures of the isolated compounds were determined using spectroscopy. The absolute configurations of the sugar moieties were determined via HPLC after acid hydrolysis. Among the isolated compounds, some flavonoids and stilbenoid glycosides exhibited plasmin-inhibitory activity.

Evaluation of Mongolian compound library for potential antimalarial and anti-Toxoplasma agents.

179 compounds in a Mongolian compound library were investigated for their inhibitory effect on the in vitro growth of Plasmodium falciparum and Toxoplasma gondii. Among these compounds, brachangobinan A at a half-maximal inhibition concentration (IC50) of 2.62 µM and a selectivity index (SI) of 27.91; 2-(2'-hydroxy-5'-O-methylphenyl)-5-(2″,5″-dihydroxyphenyl)oxazole (IC50 3.58 µM and SI 24.66); chrysosplenetin (IC50 3.78 µM and SI 15.26); 4,11-di-O-galloylbergenin (IC50 3.87 µM and SI 13.38); and 2-(2',5'-dihydroxyphenyl)-5-(2″-hydroxyphenyl)oxazole (IC50 6.94 µM and SI 11.48) were identified as potential inhibitors of P. falciparum multiplication. Additionally, tricin (IC50 12.94 µM and SI > 23.40) was identified as a potential inhibitor of T. gondii multiplication. Our findings represent a good starting point for developing novel antimalarial and anti-Toxoplasma therapeutics from Mongolian compounds.

Biological activity evaluations of chemical constituents derived from Mongolian medicinal forage plants and their applications in combating infectious diseases and addressing health problems in humans and livestock.

Mongolian nomadic people possess traditional knowledge of wild plants that grow in their areas of habitation. Many of these are forage plants in nature and are consumed by livestock. However, these plants are known to have medicinal and/or toxic properties. To establish a scientific understanding of the plants, and in turn, offer sound knowledge on their applications and effective use, it is essential to collect data pertaining to the chemical constituents of each plant. Therefore, the first objective of this study was to identify and determine the structural constituents of the forage plants that were available to our research group. Furthermore, in an attempt to demonstrate the biological activities of the isolated chemical compounds, we focused on solving some of the social issues affecting Mongolian communities, including protozoan diseases affecting livestock, vectors of infectious diseases, and the general health of humans and their livestock. The results of the chemical constituents derived from Mongolian medicinal plants and their biological activities that were studied in the recent decade are also described herein.

Saxifraga spinulosa-Derived Components Rapidly Inactivate Multiple Viruses Including SARS-CoV-2.

Novel severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), influenza A virus (IAV), and norovirus (NV) are highly contagious pathogens that threaten human health. Here we focused on the antiviral potential of the medicinal herb, Saxifraga spinulosa (SS). Water-soluble extracts of SS were prepared, and their virus-inactivating activity was evaluated against the human virus pathogens SARS-CoV-2 and IAV; we also examined virucidal activity against feline calicivirus and murine norovirus, which are surrogates for human NV. Among our findings, we found that SS-derived gallocatechin gallate compounds were capable of inactivating all viruses tested. Interestingly, a pyrogallol-enriched fraction (Fr 1C) inactivated all viruses more rapidly and effectively than did any of the component compounds used alone. We found that 25 µg/mL of Fr 1C inactivated >99.6% of SARS-CoV-2 within 10 s (reduction of ≥2.33 log10 TCID50/mL). Fr 1C resulted in the disruption of viral genomes and proteins as determined by gel electrophoresis, electron microscopy, and reverse transcription-PCR. Taken together, our results reveal the potential of Fr 1C for development as a novel antiviral disinfectant.

Isolation and evaluation of trypanocidal activity of sesquiterpenoids, flavonoids, and lignans in Artemisia sieversiana collected in Mongolia.

Artemisia sieversiana is an annual herbaceous plant distributed throughout Central and East Eurasia and is regarded as an undesirable forage plant in Mongolia. It affects livestock, so information about its chemical composition is needed. We isolated three new sesquiterpenoids (1-3) and known compounds from A. sieversiana and investigated their activities. The absolute configuration of 1 was established using single-crystal X-ray diffraction crystallography, and its configuration differed from those of reported compounds with similar structures. Two additional new sesquiterpenoids (2 and 3) with similar structures were identified, and their configurations were determined. The trypanocidal activities of the isolated compounds (1-18) against Trypanosoma congolense and the pathogen responsible for fatal trypanosomosis in animals were estimated. Flavonoids and lignans were identified as active compounds with IC50 values ranging from 2.9 to 90.2 µM.

Biological Properties, Bioactive Constituents, and Pharmacokinetics of Some Capsicum spp. and Capsaicinoids.

Pepper originated from the Capsicum genus, which is recognized as one of the most predominant and globally distributed genera of the Solanaceae family. It is a diverse genus, consisting of more than 31 different species including five domesticated species, Capsicum baccatum, C. annuum, C. pubescen, C. frutescens, and C. chinense. Pepper is the most widely used spice in the world and is highly valued due to its pungency and unique flavor. Pepper is a good source of provitamin A; vitamins E and C; carotenoids; and phenolic compounds such as capsaicinoids, luteolin, and quercetin. All of these compounds are associated with their antioxidant as well as other biological activities. Interestingly, Capsicum fruits have been used as food additives in the treatment of toothache, parasitic infections, coughs, wound healing, sore throat, and rheumatism. Moreover, it possesses antimicrobial, antiseptic, anticancer, counterirritant, appetite stimulator, antioxidant, and immunomodulator activities. Capsaicin and Capsicum creams are accessible in numerous ways and have been utilized in HIV-linked neuropathy and intractable pain.

Bioactive Compounds, Pharmacological Actions, and Pharmacokinetics of Wormwood (Artemisia absinthium).

Plants have been used since ancient times to cure certain infectious diseases, and some of them are now standard treatments for several diseases. Due to the side effects and resistance of pathogenic microorganisms to antibiotics and most drugs on the market, a great deal of attention has been paid to extracts and biologically active compounds isolated from plant species used in herbal medicine. Artemisia absinthium is an important perennial shrubby plant that has been widely used for the treatment of several ailments. Traditionally, A. absinthium has always been of pharmaceutical and botanical importance and used to manage several disorders including hepatocyte enlargement, hepatitis, gastritis, jaundice, wound healing, splenomegaly, dyspepsia, indigestion, flatulence, gastric pain, anemia, and anorexia. It has also been documented to possess antioxidant, antifungal, antimicrobial, anthelmintic, anti-ulcer, anticarcinogenic, hepatoprotective, neuroprotective, antidepressant, analgesic, immunomodulatory, and cytotoxic activity. Long-term use of A. absinthium essential oil may cause toxic and mental disorders in humans with clinical manifestations including convulsions, sleeplessness, and hallucinations. Combination chemotherapies of artemisia extract or its isolated active constituents with the currently available antibabesial or anti-malarial drugs are now documented to relieve malaria and piroplasmosis infections. The current review examines the phytoconstituents, toxic and biological activities of A. absinthium.

Hyaluronidase inhibitory saponins and a trypanocidal isoflavonoid from the aerial parts of Oxytropis lanata.

A chemical examination of an extract from the aerial part of Oxytropis lanata led to the isolation and identification of 36 compounds, including saponins, isoflavonoids, oxazoles, and glycosides. The three among them were previously unreported oleanane-type saponins. In trypanocidal screening, 5,7,4'-trihydroxyisoflavone showed inhibitory activity against Trypanosoma congolense (IC50 = 10.5 µM), the causative agent of African trypanosomosis in animals; this activity was similar to that of active compounds from the roots of this plant. O. lanata is known to be a traditional medicinal plant in Mongolia for the treatment of inflammatory diseases. The anti-hyaluronidase effect of saponins 3, 5, 8, and 9, (IC50 = 0.15-0.22 mM) was stronger than that of sodium cromoglicate, which was used as a reference drug (IC50 = 0.37 mM). The chemical structures of the new saponins were determined based on HRFABMS, 1H and 13C NMR, 1H-1H COSY, HMQC, HMBC, and ROESY spectroscopic data along with chemical procedures.

Inhibitory activities of phenylpropanoids from Lycopus lucidus on amyloid aggregation related to Alzheimer's disease and type 2 diabetes.

The number of patients with Alzheimer's disease (AD) and type 2 diabetes (T2D) is increasing rapidly, and thus more research has been focused on the relationship between these two age-related chronic diseases. According to the amyloid hypothesis, prevention of the aggregation of amyloid ß (Aß) and human islet amyloid polypeptide (hIAPP) is a promising strategy for AD and T2D. In this study, thioflavin-T assay and transmission electron microscopy were performed to evaluate the inhibitory effect of three phenylpropanoids isolated from Lycopus lucidus-schizotenuin A and lycopic acids A and B-on both Aß and hIAPP fibrillization. All tested compounds exhibited similarly strong inhibitory activity toward amyloid aggregation. These results suggested that catechol moieties play important roles in the inhibition of amyloid plaque formation.

Indirubin promotes adipocyte differentiation and reduces lipid accumulation in 3T3­L1 cells via peroxisome proliferator­activated receptor γ activation.

The peroxisome proliferator­activated receptor Î³ (PPARγ) plays an important role in insulin sensitivity and adipocyte differentiation. It is known as ligand­receptor that improves insulin sensitivity in type 2 diabetes mellitus. Several kinds of indigo plant have been already used to treat diabetes in oriental traditional medicine, but its mechanism has not been clarified yet. To investigate the effect of indirubin, which is a component of Polygonum tinctorium on the cell differentiation and adipprocess in 3T3­L1 cells, 3T3­L1 cells were cultured to determine the effect of cell differentiation and glucose uptake with indirubin. As a result, Indirubin compound enhanced adipocyte differentiation in 3T3­L1 cells similar to rosiglitazone. This effect was terminated by cotreatment with GW9662, a PPARγ antagonist. In mature 3T3­L1 adipocytes, the lipid droplet size and accumulation were reduced by this compound. The basal and insulin­stimulated glucose uptakes were also significantly increased. In addition, indirubin treatment significantly enhanced estrogen level by 1.64­fold with mature adipocytes which can be attributed to its aromatase activity. Conclutionaly, this finding suggested that indirubin is a potential anti­diabetic compound for type 2 diabetes mellitus by promoting adipocyte differentiation and glucose uptake via PPARγ.

Flavonoids isolated from the flowers of Pulsatilla flavescens and their anti-piroplasm activity.

Pulsatilla species are known as "Yargui", and their flowers are traditionally used in Mongolia as a tonic and for the treatment of inflammatory diseases. By chemical investigation of P. flavescens flowers, 21 flavonoids, including a new chalcone C-glucoside, chalconaringenin 2'-O-ß-D-glucopyranosyl-5'-ß-D-glucopyranoside, and two new flavanone C-glucosides, (2R)- and (2S)-naringenin 8-ß-D-glucopyranosyl-4'-O-ß-D-glucopyranoside, were isolated. The absolute configurations of the seven flavanone glucosides were elucidated by ECD spectra. For the isolated compounds, inhibitory activity against Babesia caballi and Theileria equi, which cause fatal diseases in horses, was estimated. Although most of the isolated chalcone and flavanone derivatives did not show any anti-piroplasm activity, all the isolated flavone and flavonol derivatives showed moderate effects against B. caballi and/or T. equi.

Lanostane triterpenoids from Fomitopsis officinalis and their trypanocidal activity.

Fomitopsis officinalis is a medicinal fungus, known as 'Agarikon', and is used traditionally in the treatment of asthma and rheumatism in Mongolia. The investigation of the chemical constituents of F. officinalis led to the isolation of 4 new lanostane triterpenoids together with 4 known triterpenoids. Inhibitory activity against Trypanosoma congolense, which causes fatal diseases in animals including livestock, was estimated for the isolated compounds. Compounds 2-5 and 8 exhibited moderate inhibition activities with IC50 values ranging from 7.0-27.1 µM.

An antibacterial ortho-quinone diterpenoid and its derivatives from Caryopteris mongolica.

To identify antibacterial components in traditional Mongolian medicinal plant Caryopteris mongolica, an ortho-quinone abietane caryopteron A (1) and three its derivatives caryopteron B-D (2-4) were isolated from the roots of the plant together with three known abietanes demethylcryptojaponol (5), 6α-hydroxydemethyl cryptojaponol (6), and 14-deoxycoleon U (7). The chemical structures of these abietane derivatives were elucidated on the basis of spectroscopic data. Compounds 1-4 had C-13 methylcyclopropane substructures, and 2-4 had a hexanedioic anhydride ring C instead of ortho-quinone in 1. The stereochemistry of these compound was assumed from NOE spectra and ECD Cotton effects. Compounds 1 and 5-7 showed antibacterial activities against the Gram-positive bacteria Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, and Micrococcus luteus, being 1 the more potent.

Cholinesterase-inhibitory diterpenoids and chemical constituents from aerial parts of Caryopteris mongolica.

A diterpenoid diglucoside (12,19-di-O-ß-D-glucopyranosyl-11-hydroxyabieta-8,11,13-triene-19-one), isoscutellarein 7-O-[ß-D-xylopyranosyl-(1→2)]-ß-D-glucopyranoside, isoscutellarein 7-O-[α-L-rhamnopyranosyl-(1→2)]-ß-D-glucopyranoside, hypolaetin 7-O-[6″-O-(p-E-coumaroyl)]-ß-D-glucopyranoside, hypolaetin 7-O-[6″-O-(E-caffeoyl)]-ß-D-glucopyranoside, and 15 known compounds were isolated from aerial parts of the Mongolian medicinal plant Caryopteris mongolica. The cholinesterase-inhibitory activities of the constituents were estimated. The abietane diterpenoids (12-O-demethylcryptojaponol and 6α-hydroxydemethylcryptojaponol) showed potent inhibitory activity against acetylcholinesterase from human erythrocytes and electric eel, and against butyrylcholinesterase from horse serum.

Chemical constituents of aerial parts and roots of Pycnanthemum flexuosum.

An extract of whole plants of Pycnanthemum flexuosum showed an inhibitory effect on hyaluronidase activity. From an 80% acetone extract of aerial parts, 3-[(3E)-4-phenylbut-3-enoylamino]propionic acid, 3-O-ß-D-glucuronopyranosyl-echinocystic acid 28-O-ß-D-xylopyranosyl-(1→3)-[3,4-diacetyl-ß-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl ester, vanillic acid 1-O-[(5-O-syringoyl)-ß-D-apiofuranosyl]-(1→2)-ß-D-glucopyranoside, and (4S,5R)-4-hydroxy-5-phenyl-tetrahydrofuran-2-one were isolated together with 30 known compounds. Six known compounds were isolated from an 80% acetone extract of roots, and eritrichin was revealed as a hyaluronidase inhibitor in P. flexuosum.

Monoterpene glycosides, phenylpropanoids, and acacetin glycosides from Dracocephalum foetidum.

Chemical investigation of the acetone extract from the aerial parts of the Mongolian medicinal plant Dracocephalum foetidum resulted in the isolation of three limonene glycosides, a caffeic acid trimer, four rosmarinic acid glucosides, and five acacetin acyl glycosides, together with 13 known natural products. The chemical structures of all of the compounds were determined by spectroscopic analyses. Among these compounds three showed hyaluronidase inhibitory activity. In addition, one other compound showed stronger 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity than the positive control Trolox, whereas three other compounds demonstrated a similar activity to that of Trolox.

Diastereomers of lithospermic acid and lithospermic acid B from Monarda fistulosa and Lithospermum erythrorhizon.

Monardic acids A (1) and B (2), which are (7R,8R) diastereomers of lithospermic acid (LA) and lithospermic acid B, respectively, were isolated from Monarda fistulosa. A (7S,8R) isomer (3) of LA was also isolated from this plant, and a (7R,8S) isomer (7) of LA was obtained from Lithospermum erythrorhizon. The absolute configuration of 1 was confirmed by analysis of its hydrolysates, 7-epiblechnic acid and 2R-3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid. The configuration in the dihydrobenzofuran moieties of 2, 3, and 7 was extrapolated by using the phenylglycine methyl ester method and a Cotton effect at approximately 250-260 nm in their electronic circular dichroism spectra. Diastereomers (1-3 and 7) displayed moderate hyaluronidase inhibitory and histamine release inhibitory activities.

Phytochemical constituents of Mongolian traditional medicinal plants, Chamaerhodos erecta and C. altaica, and its constituents prevents the extracellular matrix degradation factors.

Activity-guided isolation of the n-butanol fraction of Chamaerhodos erecta and water soluble fraction of C. altaica resulted in the isolation of 39 compounds, including new compounds identified as 4,5-dihydroxybenzaldehyde-3-O-ß-D-glucopyranoside (1) from C. erecta and quercetin-3-O-ß-D-glucuronopyranosyl-4'-O-ß-D-glucopyranoside (2) from C. altaica. A total of 37 other compounds were identified based on physico-chemical properties and spectroscopic data. Antioxidative activity was evaluated using a DPPH radical-scavenging method, hyaluronidase inhibitory activity, and advanced glycation end products production inhibitory activity of isolated compounds. Some flavonols (4, 6, 9-11, 14, 15), catechins (18, 19), an amino acid (20), a lignan glucoside (23), and tannins (29-39) exhibited potential a free radical scavenging activity while the new compound (1) showed weak activity. A catechin (18) and some of the tannins (32, 33, 35, 36, 38) had moderate hyaluronidase inhibitory activity. Some of flavonoids and tannins prevented advanced glycation end products production, and the IC50 of compounds 3, 9, 14-16, 33, 34, 36, 38, and 39 were determined.

Flavone tetraglycosides and benzyl alcohol glycosides from the Mongolian medicinal plant Dracocephalum ruyschiana.

From an extract of the aerial parts of Dracocephalum ruyschiana, five new flavone tetraglycosides, five new benzyl alcohol glycosides, and 19 known compounds were isolated. The tetraglycosides contain a 7-O-ß-d-glucopyranosyl-(1→2)-ß-d-glucopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-ß-d-glucopyranosyl moiety. The benzyl alcohol glycosides had acyl groups on their glycosyl or aglycone moieties. The compounds were tested for antioxidant activity using DPPH. Although the new compounds were not active, phenylpropanoylquinic acid derivatives were revealed as radical scavengers in D. ruyschiana.

Lipase inhibitory and LDL anti-oxidative triterpenes from Abies sibirica.

A methanol extract of Abies sibirica Ladeb, a Mongolian medicinal plant, had an inhibitory effect on both lipase activity in mouse plasma and LDL anti-oxidative activity, which are preventative factors for arteriosclerosis. The extract was fractionated by silica gel column chromatography and its active constituents were sought. From lipid soluble fractions, 20 terpenoids including seven hitherto unknown triterpenes were isolated. The latter triterpenes had either a γ-lactone ring with a lactol or a derivative thereof. Their chemical structures were determined by spectroscopic methods. The lipase inhibitory activity and LDL anti-oxidative activity of these compounds were evaluated. Some constituents (either lipase inhibitory or LDL anti-oxidative activities) had moderate inhibitory activities.