Oleanane-type Triterpene Glycosides Research Articles

Oleanane-Type Triterpene Glycosides from Camellia phanii and Their α-Glucosidase Inhibitory Activity.

Three new oleanane-type triterpene saponins, named camphanosides A-C (1-3), along with five known compounds, chikusetsusaponin IVa (4), spinasaponin A 28-O-glucoside (5), (-)-epicatechin (6), (-)-epicatechin 3-O-gallate (7), and (-)-epigallocatechin 3-O-gallate (8) were isolated from the leaves Camellia phanii Hakoda & Ninh. Their structures were established by 1D and 2D-NMR and mass spectral analysis and chemical methods. Moreover, compounds 1-5 were also evaluated for α-glucosidase inhibitory activity. Compounds 1-3 exhibited moderate α-glucosidase inhibitory activity with IC50 values of 230.7±18.0, 251.4±22.7, and 421.4±25.6 μM, respectively.

Two new saponins from Paronychia capitata

Two new oleanane-type triterpene glycosides, 3˗ O ˗β˗D˗glucopyranosyl˗28˗ O ˗[β˗D˗glucopyranosyl˗(1→2)˗β˗D˗xylopyranosyl˗(1→6)˗β˗D˗glucopyranosyl]medicagenic acid ( 1 ) and 3˗ O ˗β˗D˗glucopyranosyl˗28˗ O ˗[β˗D˗glucopyranosyl˗(1→6)˗β˗D˗glucopyranosyl˗(1→2)˗ β˗D˗xylopyranosyl]oleanolic acid ( 2 ), named capitatosides A and B respectively, were isolated from the butanol extract of Paronychia capitata (L.) Lam., along with seven known compounds. The structures of the isolated compounds were established by spectroscopic methods, mainly HRMS, 1D and 2D NMR ( 1 H, 13 C, COSY, HSQC, HMBC and NOESY) techniques, whereas those of the known compounds were identified by spectral comparison with reported literature data. • A phytochemical study of Paronychia capitata was carried out. • The butanol extract was investigated using chromatographic methods. • Two new oleanane-type triterpene glycosides along with seven known compounds were identified. • The structures of the isolates were established by spectroscopic methods. • The first characterization of saponosides from the genus Paronychia .

Two new triterpene glycosides with antiproliferative activities on HepG2 from Phytolacca acinosa fruit fermentation broth

Two new oleanane-type triterpene glycosides, phytolasides A (1) and B (2), and six known ones (3–8), were isolated from Phytolacca acinosa fruit fermentation broth. Their structures were elucidated by HR-ESI-MS and 1 D- and 2 D-NMR spectroscopic methods. Antiproliferation of compounds 1 and 2 against HepG2 cells was examined by using CCK8 assays.

Novel Oleanane-Type Triterpene Glycosides from the Saponaria officinalis L. Seeds and Apoptosis-Inducing Activity via Mitochondria

Saponaria officinalis L., commonly known as “Soapwort”, is a rich source of triterpene glycosides; however, the chemical constituents of S. officinalis seeds have not been fully identified. In this study, we conducted a systematic phytochemical investigation of the seeds of S. officinalis and obtained 17 oleanane-type triterpene glycosides (1–17), including seven new glycosides (1–7). The structures of 1–7 were determined based on a detailed analysis of NMR spectroscopic data and chromatographic and spectroscopic analyses following specific chemical transformation. The cytotoxicities of the isolated compounds were evaluated against HL-60 human promyelocytic leukemia cells, A549 human adenocarcinoma lung cancer cells, and SBC-3 human small-cell lung cancer cells. The cytotoxicities of 1, 4, and 10 toward HL-60 cells and SBC-3 cells were nearly as potent as that of cisplatin. Compound 1, a bisdesmosidic triterpene glycoside obtained in good yield, arrested the cell cycle of SBC-3 cells at the G2/M phase, and induced apoptosis through an intrinsic pathway, accompanied by ROS generation. As a result of the mitochondrial dysfunction induced by 1, mitochondria selective autophagy, termed mitophagy, occurred in SBC-3 cells.

Aramatosides C and D, 2 Previously Undescribed Triterpene Glycosides Isolated From the Roots of Aralia armata

The 2 new oleanane-type triterpene glycosides, 23-hydroxyoleanolic acid-[28- O- β-D-glucopyranosyl]-3- O-{ β-D-glucopyranosyl-(1→2)-[ β-D-glucopyranosyl-(1→3)]- β-D-galactopyranoside}, (1) and oleanolic acid-[28- O- β-D-glucopyranosyl]-3- O-{ β-D-glucopyranosyl-(1→2)-[ β-D-glucopyranosyl-(1→3)]- β-D-galactopyranoside} (2) were isolated from the roots of Aralia armata. Their chemical structures were elucidated by using a combination of high resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1 dimensional (1D), and 2 dimensional (2D) nuclear magnetic resonance spectral data, as well as by comparison with the previous literature. Compounds 1 and 2 displayed weak cytotoxic activity toward KB and HepG2 cell lines with IC50 values of 25.1 ± 1.2 and 23.7 ± 0.9 µM (for 1) and 29.5 ± 1.3 and 23.9 ± 0.7 µM (for 2), respectively, compared to that of the positive control compound, ellipticine (IC50: 1.3 ± 0.1 and 1.6 ± 0.1 µM, respectively) in in vitro assay.

Traditional uses, phytochemistry, pharmacology and other potential applications of Vitellaria paradoxa Gaertn. (Sapotaceae): A review

Vitellaria paradoxa Gaertn. is a multipurpose medicinal plant of the family Sapotaceae, and it has been widely used usually in the clinical traditional medicine as remedy for a wide range of diseases for several decades. In addition, the plant has also found applications in confectionery, cosmetics and soaps, and pharmaceuticals both locally and internationally. V. paradoxa, which has been identified with >150 phytoconstituents, is rich in oleanane-type triterpene acids and glycosides, such as paradoxosides A-E, tieghemelin A, parkiosides A-C, bassic acid, as well as flavonoids such as quercetin and catechin-type compounds. The extracts and the active constituents of V. paradoxa have been investigated for various pharmacological activities, including but not limited to anticancer, melanogenesis-inhibitory, antibacterial, anti-diabetic, antioxidant, anti-inflammatory, anti-diarrhoeal, and antifungal activities. Additionally, V. paradoxa has also been utilized in nanoparticles (NPs) synthesis. These NPs among other things have shown significant antinociceptive and antiedematogenic activities as well as environmental friendly adsorptive properties for the removal of pollutants from pharmaceutical effluents. Overall, this review comprehensively examines the traditional uses, phytochemistry, pharmacology, toxicology, clinical studies, and nanoparticles synthesized from V. paradoxa and their applications.

Araliachinoside A: A New Triterpene Glycoside From Aralia chinensis Leaves

From the leaves of Aralia chinensis, 3 oleanane-type triterpene glycosides have been isolated, including 1 new glycoside, 3β,23 -dihydroxyolean-12-ene-28-oic acid 3 -O-β-d-glucopyranosyl-(1→3)- α-l-arabinopyranosyl-(1→3)-β-d-glucuronopyranoside 28 -O-β-d-glucopyranosyl ester (named as araliachinoside A, 1), and 2 known ones, 3β,23 -dihydroxyolean-12-ene-28-oic acid 3 -O-α-l-arabinopyranosyl-(1→3)- β-d-glucuronopyranoside 28 -O-β-d-glucopyronosyl ester (2) and 3β-hydroxyolean-12-ene-28-oic acid 3 -O-β-d-glucurono pyranoside 28 -O-β-d-glucopyronosyl ester (3). Their chemical structures were elucidated by using a combination of high-resolution electrospray ionization-mass spectrometry, 1-dimensional and 2-dimensional nuclear magnetic resonance spectral data, and by comparison with previous literature. Compounds 1-3 displayed cytotoxic activity toward KB and HepG2 cell lines with half-maximal inhibitory concentration values ranging from 8.1 ± 0.1 to 15.7 ± 0.3 µM in in vitro assay.

Anti-Inflammatory and anti-proliferative oleanane-type triterpene glycosides from the vine of Momordica cochinchinensis

This research isolated two new oleanane-type triterpene glycosides, named mocochinosides A (1) and B (2), together with ten known compounds as chikusetsusaponin IVa ethyl ester (3), momordin Ib (4), momordin IIb (5), momordin II (6), calenduloside G (7), calenduloside H (8), elatoside A (9), elatoside C (10), calendulaglycoside C 6'-O-7-butyl ester (11), and hederagenin 3-O-β-D-glucuronopyranoside (12) and characterized them from the vines of Momordica cochinchinensis. The new structures of both glycosides 1-2 were elucidated by spectroscopic analysis including 2 D NMR and MS, followed by an analysis of their anti-inflammatory and cytotoxic activities. Compounds 1, 4, and 11 showed moderate inhibitions for NO production on RAW264.7 macrophages induced by LPS at IC50 5.41 ∼ 11.28 μM. Compounds 3, 4, and 7 (IC50 8.42 ∼ 19.74 μM) exhibited potential anti-proliferative activities against both of WiDr and MCF-7 human tumor cell lines.

Melanogenesis-Inhibitory and Cytotoxic Activities of Triterpene Glycoside Constituents from the Bark of Albizia procera.

Five oleanane-type triterpene glycosides including three new ones, proceraosides E-G (1-3), were isolated from a MeOH-soluble extract of Albizia procera bark. The structures of 1-3 were determined by use of NMR spectra, HRESIMS, and chemical methods. Compounds 1-5 exhibited inhibitory activities against the proliferation of the A549, SKBR3, AZ521, and HL60 human cancer cell lines (IC50 0.28-1.8 μM). Additionally, the apoptosis-inducing activity of compound 2 was evaluated by Hoechst 33342 staining and flow cytometry, while the effects of 2 on the activation of caspases-9, -8, and -3 in HL60 cells were revealed by Western blot analysis.

Compositions and melanogenesis-inhibitory activities of the extracts of defatted shea (Vitellaria paradoxa) kernels from seven African countries

Constituents of shea (Vitellaria paradoxa; Sapotaceae) kernels are commonly used as functional food and for skin care by indigenous peoples in Africa. Twenty-six MeOH extract samples of defatted shea kernels from seven sub-Saharan countries, i.e., Côte d'Ivoire, Ghana, Nigeria, Cameroon, Chad, Sudan, and Uganda, were investigated in this study. HPLC coupled to an evaporative light-scattering detector and LC-QTOF (time-of-flight)-MS revealed that the extracts contained sugars (25.6–80.2%) as the most predominant constituents, followed by oleanane-type triterpene glycosides (4.9–35.2%), accompanied by minor amounts of cucurbates (1.0–21.0%) and phenolic compounds (0.3–16.0%). Principal component analysis and hierarchical clustering analysis classified the twenty-six samples into three groups. Upon evaluation of the melanogenesis-inhibitory activities of all samples in B16 melanoma cells induced by α-melanocyte-stimulating hormone, it was found that samples S2, S3, and S21 were lower-risk melanogenesis inhibitors (39.4–42.5% melanin content, 78.6–91.6% cell viability) with a small activity-to-cytotoxicity ratio (0.18–0.94), and were superior to reference arbutin at a concentration of 100 μg/mL. These results suggest that the extracts of defatted shea kernels and their constituents can be regarded as skin-whitening agents.

Novel saponins from Nigella arvensis var. involucrata

Four new oleanane-type triterpene glycosides namely 3-O-[β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)-α-l-arabinopyranosyl] oleanolic acid, 3-O-[β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)-α-l-arabinopyranosyl]-28-O-[α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl] oleanolic acid, 3-O-[β-d-quinovopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl]-28-O-[β-d-glucopyranosyl] oleanolic acid, 3-O-[β-d-quinovopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl]-28-O-[α-l-rhamnopyranosyl(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl] oleanolic acid, were isolated from methanol extract of the roots of Nigella arvensis var. involucrata along with five known oleanane-type triterpene glycosides and a steroid glucoside. Structures of the new compounds were established as by using 1D and 2D NMR techniques and mass spectrometry.

Triterpene glycosides and other polar constituents of shea (Vitellaria paradoxa) kernels and their bioactivities

The MeOH extract of defatted shea (Vitellaria paradoxa; Sapotaceae) kernels was investigated for its constituents, and fifteen oleanane-type triterpene acids and glycosides, two steroid glucosides, two pentane-2,4-diol glucosides, seven phenolic compounds, and three sugars, were isolated. The structures of five triterpene glycosides were elucidated on the basis of spectroscopic and chemical methods. Upon evaluation of the bioactivity of the isolated compounds, it was found that some or most of the compounds have potent or moderate inhibitory activities against the following: melanogenesis in B16 melanoma cells induced by α-melanocyte-stimulating hormone (α-MSH); generation of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, against Epstein–Barr virus early antigen (EBV-EA) activation induced by 12-O-teradecanoylphorbol 13-acetate (TPA) in Raji cells; t TPA-induced inflammation in mice, and proliferation of one or more of HL-60, A549, AZ521, and SK-BR-3 human cancer cell lines, respectively. Western blot analysis established that paradoxoside E inhibits melanogenesis by regulation of expression of microphthalmia-associated transcription factor (MITF), tyrosinase, and tyrosinase-related protein-1 (TRP-1) and TRP-2. In addition, tieghemelin A was demonstrated to exhibit cytotoxic activity against A549 cells (IC50 13.5μM) mainly due to induction of apoptosis by flow cytometry. The extract of defatted shea kernels and its constituents may be, therefore, valuable as potential antioxidant, anti-inflammatory, skin-whitening, chemopreventive, and anticancer agents.

Oleanane type glycosides from Paronychia anatolica subsp. balansae

Four new oleanane-type triterpene glycosides were isolated from the methanol extract of the roots of Paronychia anatolica subsp. balansae along with three known oleanane-type triterpene glycosides. Structures of the new compounds were established as 3-O-β-d-glucuronopyranosyl-28-O-[α-l-rhamnopyranosyl-(1→2)-β-d-quinovopyranoside] zahnic acid, 3-O-β-d-glucuronopyranosyl-28-O-[β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-β-d-quinovopyranoside] zahnic acid, 3-O-β-d-glucuronopyranosyl-28-O-[α-l-arabinofuranosyl-(1→2)-β-d-quinovopyranoside] zahnic acid, 28-O-[α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl]-medicagenic acid, by using 1D and 2D-NMR techniques and mass spectrometry. The cytotoxic activity of the isolated compounds was evaluated against a small panel of cancer cell lines including human breast cancer (MCF-7), human lung adenocarcinoma (A549) and human leukemia (U937) cell lines.

Oleanane glycosides from Astragalus tauricolus: Isolation and structural elucidation based on a preliminary liquid chromatography-electrospray ionization tandem mass spectrometry profiling

As a part of our ongoing research for bioactive compounds from Turkish Astragalus species, the investigation of Astragalus tauricolus has been carried out. An approach based on HPLC-ESIMS(n) experiments has been used to profile the triterpene glycosides occurring in the butanol extract of the whole plant. On the basis of the results of the online screening by HPLC-ESIMS(n), 22 oleanane-type triterpene glycosides, including ten compounds never reported before, were isolated, and their structures were established by the extensive use of 1D and 2D-NMR experiments along with ESIMS and HRMS analysis. Noteworthy, cycloartane-type triterpene glycosides, the main constituents of Astragalus spp., were not found. This peculiar feature characterizes a very limited group of Astragalus spp. The antiproliferative activity of the isolated compounds 1-12, 15, 17-19 was evaluated against a small panel of cancer cell lines. Only compound 11 showed an IC(50) of 22 μM against human leukemia cell line (U937). The other tested compounds, in a range of concentrations between 1 and 50 μM, did not cause any significant reduction of the cell number.

Oleanane glycosides from the roots of Alhagi maurorum

Three new oleanane-type triterpene glycosides (1–3), along with four known compounds (4–7) glycosides, were isolated from the roots of Alhagi maurorum. Their structures were elucidated by 1D and 2D-NMR experiments as well as ESI-MS analysis. The antiproliferative activity of the isolated compounds was evaluated against a small panel of cancer cell lines including human breast cancer (MCF-7), human lung adenocarcinoma (A549), human prostate cancer (PC-3) and human leukemia (U937) cell lines. None of the tested compounds, in a range of concentrations between 1 and 50μM, caused a significant reduction of the cell number.

Pot marigold (Calendula officinalis) medicinal usage and cultivation

Calendula pot marigold, is a genus of about 12 to 20 species of annual or perennial herbaceous plants in the daisy family Asteraceae, native to the area from Macaronesia East through the Mediterranean region to Iran. Calendula should not be confused with other plants that are also known as marigolds, such as corn marigold, desert marigold, or marsh marigold or plants of the genus Tagetes. The name Calendula stems from the Latin word kalendae, means first day of the month, presumably because pot marigolds are in bloom at the start of most months of the year. The common name marigold probably refers to the Virgin Mary, or its Old Saxon name 'ymbglidegold', which means 'it turns with the sun’. The most commonly cultivated and used member of the genus is the pot marigold (Calendula officinalis). The flowers of C. officinalis contain flavonol glycosides, triterpene oligoglycosides, oleanane-type triterpene glycosides, saponins, and a sesquiterpene glucoside Plant pharmacological study have suggested that Calendula extracts have anti-viral, anti-genotoxic and anti-inflammatory properties. Calendula in suspension or in tincture is used topically to treat acne, reducing inflammation, controlling bleeding and soothing irritated tissue. There is limited evidence that calendula cream or ointment is effective in treating radiation dermatitis. In a randomized study of 254 radiation patients, topical application of 4% calendula ointment resulted in far fewer occurrences of Grade 2 or higher dermatitis than occurred in the group using trolamine. Calendula has been used traditionally for abdominal cramps and constipation. Key words: Calendula officinalis, saponins, ornamental plant, candolin.

Triterpene Glycosides fromAstragalus angustifolius

Six new cycloartane-type (1- 6) and four new oleanane-type (7- 10) triterpene glycosides were isolated from Astragalus angustifolius Lam., together with five known triterpene glycosides. Their structures were established by the extensive use of 1D and 2D-NMR experiments along with ESIMS and HRMS analysis. Compounds 1- 3 are glycosides of cycloastragenol, while compounds 4- 6 show the C-24 epimer of cycloastragenol as aglycone, encountered for the first time in nature. All compounds were evaluated for their antiproliferative activity in Hela, H-446, HT-29, and U937 cell lines. Only compound 8 displayed a weak activity with IC (50) values of 36 and 50 µM against Hela and HT-29 cell lines, respectively.

Triterpene glycosides from Astragalus icmadophilus

Six cycloartane-type triterpene glycosides were isolated from Astragalus icmadophilus along with two known cycloartane-type glycosides, five known oleanane-type triterpene glycosides and one known flavonol glycoside. The structures of the six compounds were established as 3- O-[α-L-arabinopyranosyl-(1 → 2)- O-3-acetoxy -α-L-arabinopyranosyl]-6- O-β-D-glucopyranosyl-3β,6α,16β,24( S),25-pentahydroxycycloartane, 3- O-[α-L-rhamnopyranosyl-(1 → 2)- O-α-L-arabinopyranosyl-(1 → 2)- O-β-D-xylopyranosyl]-6- O-β-D-glucopyranosyl-3β,6α,16β,24( S),25-pentahydroxy cycloartane, 3- O-[α-L-arabinopyranosyl-(1 → 2)- O-3,4-diacetoxy-α-L-arabinopyranosyl]-6- O-β-D-glucopyranosyl-3β,6α,16β,24( S),25-pentahydroxycycloartane, 3- O-[α-L-arabinopyranosyl-(1 → 2)- O-3-acetoxy-α-L-arabinopyranosyl]-6- O-β-D-glucopyranosyl-3β,6α,16β,25-tetrahydroxy-20( R),24( S)-epoxycycloartane, 3- O-[α-L-arabinopyranosyl-(1 → 2)- O-β-D-xylopyranosyl]-6- O-β-D-glucopyranosyl-3β,6α,16β,24α-tetrahydroxy-20( R),25-epoxycycloartane, 3- O-[α-L-rhamnopyranosyl-(1 → 2)- O-α-L-arabinopyranosyl-(1 → 2)- O-β-D-xylopyranosyl]-6- O-β-D-glucopyranosyl-3β,6α,16β,24α-tetrahydroxy-20( R),25-epoxycycloartane by the extensive use of 1D- and 2D-NMR experiments along with ESIMS and HRMS analysis. The first four compounds are cyclocanthogenin and cycloastragenol glycosides, whereas the last two are based on cyclocephalogenin as aglycone, more unusual in the plant kingdom, so far reported only from Astragalus spp.

Two new bioactive oleanane triterpene glycosides from Terminalia arjuna

Two new oleanane-type triterpene glycosides designated as Termiarjunoside I and Termiarjunoside II were isolated from stem bark of Terminalia arjuna (Combretaceae) and characterized as olean-1α,3β,9α,22α-tetraol-12-en-28-oic acid-3β-D-glucopyranoside (1) and olean-3α,5α,25-triol-12-en-23,28-dioic acid-3α-D-glucopyranoside (2) based on chemical and spectral data evidences. Both compounds 1 and 2 potently suppressed the release of nitric oxide and superoxide from macrophages and also inhibited aggregation of platelets.

Triterpene Glycosides from the Flower Petals of Sunflower (Helianthus annuus) and Their Anti-inflammatory Activity

Two new oleanane-type triterpene glycosides, named helianthosides 4 (4) and 5 (5), along with four known triterpene glycosides, helianthosides 1 (1), 2 (2), 3 (3), and B (6), were isolated from an n-butanol-soluble fraction of a methanol extract of sunflower (Helianthus annuus) petals. The structures of the two new compounds were determined on the basis of spectroscopic and chemical methods. Upon evaluation of compounds 1-6 for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1.7 nmol/ear) in mice, all of the compounds tested exhibited marked anti-inflammatory activity, with ID50 values in the range 65-262 nmol per ear.