ABSTRACT
Two new ursane triterpenoids along with twelve known compounds were isolated from 80% ethanol extract of Agastache rugosa (Fisch. et. Mey.) O. Kuntze by using silica gel column, MCI column, ODS column and HPLC. The structures of the new compounds were identified as 2α,3α-dihydroxy-24-nor-urs-4(23),12(13)-dien-28-oic acid (1) and 2α,3α-dihydroxy-24-nor-urs-4(23),12(13),20(30) -trien-28-oic acid (2) by HR-ESI-MS, NMR and ECD spectral data, named agasursacid A and agasursacid B. In addition, compounds 3, 4, 6, 8 showed anti-coxsackievirus B3 (CVB3) activities with a IC50 as 4.77, 1.59, 11.11 and 25.87 μmol·L-1, resepectively.
ABSTRACT
Seven new triterpenoid saponins, including five ursane-type saponins, ilexchinenosides R-V (1-5), and two oleanane-type saponins, ilexchinenosides W-X (6-7), with four known triterpenoid saponins (8-11) were isolated from the leaves of Ilex chinensis. Their structures were elucidated by comprehensive spectroscopic 1D and 2D NMR and HR-ESI-MS data. Their sugar moieties were determined by HPLC analysis compared with standards after hydrolysis and derivatization. Compounds 1, 2, 4, 9 and 10 exhibited potential hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell injury in vitro.
ABSTRACT
Protein tyrosine phosphatase 1B (PTP1B) has led to an intense interest in developing its inhibitors as anti-diabetes, anti-obesity and anti-cancer agents. The fruits of Rubus chingii (Chinese raspberry) were used as a kind of dietary traditional Chinese medicine. The methanolic extract of R. chingii fruits exhibited significant PTP1B inhibitory activity. Further bioactivity-guided fractionation resulted in the isolation of three PTP1B inhibitory ursane-type triterpenes: ursolic acid (1), 2-oxopomolic acid (2), and 2α, 19α-dihydroxy-3-oxo-urs-12-en-28-oic acid (3). Kinetics analyses revealed that 1 was a non-competitive PTP1B inhibitor, and 2 and 3 were mixed type PTP1B inhibitors. Compounds 1-3 and structurally related triterpenes (4-8) were further analyzed the structure-activity relationship, and were evaluated the inhibitory selectivity against four homologous protein tyrosine phosphatases (TCPTP, VHR, SHP-1 and SHP-2). Molecular docking simulations were also carried out, and the result indicated that 1, 3-acetoxy-urs-12-ene-28-oic acid (5), and pomolic acid-3β-acetate (6) bound at the allosteric site including α3, α6, and α7 helix of PTP1B.
Subject(s)
Humans , Enzyme Inhibitors , Chemistry , Metabolism , Fruit , Chemistry , Kinetics , Methanol , Chemistry , Molecular Docking Simulation , Molecular Structure , Plant Extracts , Chemistry , Protein Binding , Protein Tyrosine Phosphatase, Non-Receptor Type 1 , Metabolism , Protein Tyrosine Phosphatases , Rubus , Chemistry , Structure-Activity Relationship , Triterpenes , Chemistry , MetabolismABSTRACT
The flower buds of Lonicera macranthoides (Shan Yin-Hua), represent an important traditional Chinese medicine and food ingredient. A phytochemical investigation of the 70% EtOH extract of the flower buds of L. macranthoides resulted in the isolation of 12 triterpenoids (1-12), including two new ursane-type nortriterpenes, 2α, 24-dihydroxy-23-nor-ursolic acid (1) and 2α, 4α-dihydroxy-23-nor-ursolic acid (2). Their structures were established by multiple spectroscopic methods and comparison with literature data. All isolated compounds were evaluated for their anti-inflammatory effects in LPS-activated RAW264.7 cells. Compounds 1 and 2 exhibited inhibitory effects on iNOS at the concentration of 30 μmol·L.
Subject(s)
Animals , Mice , Anti-Inflammatory Agents , Chemistry , Pharmacology , Drugs, Chinese Herbal , Chemistry , Enzyme Inhibitors , Chemistry , Pharmacology , Ethanol , Chemistry , Flowers , Chemistry , Lonicera , Chemistry , Macrophages , Metabolism , Molecular Structure , Nitric Oxide , Metabolism , Nitric Oxide Synthase Type II , Plant Extracts , Chemistry , Plants, Edible , Chemistry , Triterpenes , Chemistry , PharmacologyABSTRACT
Cardiovascular and cerebrovascular diseases are the leading cause of death among adult populations in China. The incidence and mortality rate shows an upward trend, and age of onset is younger trend. It is necessary to treat cardiovascular and cerebrovascular diseases with Chinese materia medica. Natural products have been the important and productive source of leading compounds for the development of anti-cardiovascular and cerebrovascular drugs. Naturally occurring triterpenoid saponins are generally plant-derived secondary metabolites with various valuable pharmacological properties. Pentacyclic triterpenoids of which show obvious anti-inflammatory, antitumor and antiviral effects. In recent years, increasing researches focused on the anticardiovascular and cerebrovascular mechanisms and modifications to improve the pharmacological activity and druggability of pentacyclic triterpenes. Based on previous studies, the literatures and patents of nearly 10 years on pentacyclic triterpenoids and their derivatives have been consulted. The research progress of anti-cardio-cerebrovascular activities of four types of compounds, oleanane, ursane, lupane, and friedelane, related to pentacyclic triterpenoids is reviewed, which provides a basis and reference for its further development and utilization in the treatment of cardiovascular and cerebrovascular diseases.
ABSTRACT
ABSTRACT A new ursane-type triterpene ester, plectraterpene [3β-(decanoyloxy)-19-hydroxy-urs-12-ene] and four known steroidal compounds have been isolated from the aerial parts of Plectranthus montanus Benth. (syn. Plectranthus cylindraceus Hochst. ex Benth.), Lamiaceae. The known compounds were stigmasterol, sitosteryl ferulate, cholest-5-en-3-O-β-D-glucopyranoside and stigmasterol-3-O-β-D-glucopyranoside. Compounds plectraterpene, sitosteryl ferulate and stigmasterol-3-O-β-D-glucopyranoside are reported for the first time from this plant whereas compound cholest-5-en-3-O-β-D-glucopyranoside first time from the genus. The structures of these compounds were determined through spectral analysis, including extensive 2D NMR data as well as chemical methods and comparison with literature.
ABSTRACT
To investigated the chemical constituents of the roots of Psidium guajava,we isolated seven compounds by silica gel column chromatography.These include oleanane derivatives,2 α,3β,6β,23-tetrahydroxylurs-12,20(30)-dien-28-oic acid β-D-glucopyranoside (1),2α,3β,6β,23-tetrahydroxylurs-12,18-dien-28-oic acid β-D-glucopyranoside (2),2α,3β,23-trihydroxylurs-12,18-dien-28-oic acid β-D-glucopyranoside (3), nigaichigoside F1(4),asiaticoside C (5),2α,3β,6β,19α,23-pentahydroxylurs-12,18-dien-28-oic acid β-Dglucopyranoside (6) and 2α,3β,19α,23-tetrahydroxylurs-12-en-28-oic acid (7).Their structures were elucidated on the basis of spectral analysis with reference to the published data.Compound 1 is brand new,compounds 2-6 were first isolated from this plant.The new compound was evaluated for their cytotoxic activity against human hepatoma Bel 7402 in vitro.The results were expressed as the ratio of inhibiting Bel 7402 cells growth by comparing to untreated cells.The new compound (concentration:25 μmol·L-1) showed the ratio values of 52.5%.
ABSTRACT
Nor-ursane triterpenes are formed by the reduction of one or several methyl groups on the ursane triterpene carbon skeleton. According to the position of vacant methyl, they can be divided into eight types, including 23-nor, 24-nor, 28-nor, 29-nor, 30-nor, 2-nor, 3-nor, and 3,24-nor. Moreover, nor-ursane triterpenes have several pharmacological effects such as anti-cancer, anti-inflammatory, anti-bacterial, inhibition of acyl cholesterol acyl transferase (ACAT) and so on. In this study, more than 30 relevant literatures of nor-ursane triterpenoid compounds at home and abroad were reviewed. The plant distribution, pharmacological activity and structural characteristics of nor-ursane triterpenes were studied. Therefore, this review may provide the basis for further study of this type of compound.
ABSTRACT
Objective: To study the chemical constituents of the acid hydrolysis products, in order to find some new aglycones from the hydrolysate of the saponin of Centella asiatica. Methods: The acid hydrolytic product was separated by repeated silica gel, Sephadex LH-20 chromatography. The cytotoxic activities in vitro of some compounds isolated were evaluated. Their structures isolated were identified by analysis of their spectral data of NMR, MS, IR, and UV. Results: Four aglycones, 2α,3β,23-trihydroxyurs-6,12-dien-28-oic acid (1), asiatic acid (2), 6β-hydroxy asiatic acid (3), terminolic acid (4), were isolated from the hydrolysis product. Conclusions: Compound 1, named centella-6-ene, was a new ursane-type aglycone and it showed no cytotoxic activities against the tested cancer cell lines.
ABSTRACT
A new ursane-type triterpenoid saponin, 2α,3α,24-trihydroxyurs-12,20(30)-dien-28-oic acid β-D-glucopyranosyl ester (1), together with six known triterpenoid saponins, was isolated and characterized from the aerial parts of Clematoclethra scandens subsp. actinidioides.