Phytochemical study, antioxidant and tyrosinase inhibitory activities of Pentzia monodiana Maire.

Chemical investigation of the aerial parts of Pentzia monodiana Maire led to the isolation and identification of one sesquiterpene lactone glucoside of the guaianolide type (dihydropseudoivalin-4-O-ß-d-glucopyranoside), along with nine known compounds including one diterpenoid, two sesquiterpenoids, three lignanes and three flavonoids. Their structures were established on the basis of spectroscopic analysis. All these compounds were evaluated for their DPPH radical scavenging and tyrosinase inhibitory activities. Only lignanes and flavonoids showed good to moderate DPPH radical scavenging activity with EC50 ranging from 10.6 to 47.5 µM. The new sesquiterpene lactone glucoside showed low tyrosinase inhibitory activity whereas the isolated lignanes and flavonoids exhibited a moderate activity with IC50 ranging from 45.4 to 97.2 µM).

Phytochemical profiles and evaluation of the biological potential of ethyl acetate and n-butanol fractions of the aerial parts of Cistus albidus L.

The phytochemical profiles of the ethyl acetate (EAFCA) and n-butanol (BFCA) fractions of the aerial parts of Cistus albidus L., were characterised by a developed LC-ESI-MS/MS method, using 53 fingerprint phytochemicals, revealing the presence of 26 and 22 compounds, respectively with quinic acid, gallic acid, protocatechuic acid, catechin, gentisic acid, tannic acid, ellagic acid, quercitrin, astragalin as the major compounds of the EAFCA, in very higher amounts than in the BFCA. The antioxidant activity was evaluated using six methods (DPPH•, ABTS•+, GOR•, CUPRAC, FRAP and Phenanthroline). In agreement with its highest polyphenolic content (430.12 ± 1.02 µg GAE/mg of extract) and largest amounts of identified polyphenolics, the EAFCA exhibited a higher antioxidant activity than the BFCA. Additionally, the EAFCA showed the highest acetylcholinesterase (AChE) inhibition (IC50 of 25.1 ± 2.58 µg/mL). Moreover, both EAFCA and BFCA demonstrated high photoprotective activity, with sun protection factor (SPF) values of 36.49 and 36.52, respectively.

RP-UHPLC-ESI-QTOF-MSn analyses, antioxidant, antimicrobial, analgesic activities and toxicity of Achillea ligustica All.

Fourty five polyphenols were identified in the hydroethanol extract of Achillea ligustica All. by LC-HRMS/MS with caffeoyl-6-oleside (5.74%), eucommin A (4.03%), quercetin-3-O-ß-D-glucoside (3.13%) and cirsimaritin (2.95%) as the major compounds. A good antioxidant potential was shown in DPPH, ABTS and phenanthroline tests and the highest antioxidant activity (A0.5:36.23 ± 3.07 µg/mL), which was close to the standard α-tocopherol, was shown in Reducing power. The extract inhibited the growth of all tested microorganisms with MICs ranging between 10 and 190 µg/mL. In the acute toxicity test, no death was observed at doses of 100, 750 and 1500 mg/Kg with DL50 higher than 2000 mg/Kg. In analgesic in vivo assay, the extract showed a very important capacity to reduce pain, whether central or peripheral, with a certain dose-dependent relationship. For the three tests (tail flick, hot plate and acetic acid assay), the effective dose was 750 mg/kg.

Phytochemical profiling and antioxidant activity of Linum trigynum.

In this study, the total phenolic and flavonoid contents (TPC and TFC), secondary metabolite composition (LC-HRMS/MS analyses) and antioxidant potential (DPPH, ABTS, GOR, CUPRAC, and phenanthroline assays) of Linum trigynum L. (LT) extracts were determined. Our results showed for the first time that the extracts (PE, CHCl3, AcOEt, and n-BuOH) of LT exert antioxidant activity. The AcOEt and n-BuOH extracts were the most antioxidant compared to the standards, and had a higher amount of TPC (323.51 ± 0.62; 229.98 ± 6.80 µg GAE/mL) and TFC (183.75 ± 1.17 and 157.50 ± 1.77 µg QE/mL), resectively. The high antioxidant properties of these extracts may be due to their major compounds (phenolic compounds) detected by LC-HRMS/MS analyses including flavonoids (40 compounds) and phenolic acids and derivatives (18 and 19 compounds, respectively). AcOEt and n-BuOH extracts of LT can be used as an excellent source of antioxidant phytochemicals to prevent or treat various diseases.

Facile green in situ hemisynthesis of new chiral chromeno-pyrimidine derivatives: antibacterial, antioxidant activities and molecular docking study.

A hemisynthesis 'in situ' reaction of (thio)barbituric acids with an α,ß-unsaturated aldehyde using perillaldehyde from Ammodaucus leucotrichus essential oil, afforded chromeno-pyrimidine derivatives B-1 and B-2. The reaction was carried out in water and water/ethanol medium without a catalyst. The obtained pyrimidines were identified by their spectral 1H,13C, Dept-135, HMBC, HSQC, COSY, and NOESY 2D. The antioxidant activity of both compounds was evaluated using different in vitro methods (DPPH, ABTS, and CUPRAC). The hemisynthesized molecules exhibited a bacteriostatic effect against ten tested gram (+) and gram (-) strains. According to the molecular docking analysis, B-1 showed lower binding energies compared to B-2 against (PDB: 1HD2) and (PDB: 1KZN) targets, which is in agreement with the ABTS and E. Coli assays. Furthermore, a probable promising anti-HIV activity was noticed against reverse transcriptase (PDB: 2RKI), a key enzyme for HIV replication. The ADME properties calculations showed no Lipinski's rule violation for both compounds.

A new acylated flavonol triglycoside and evaluation of the antioxidant activity of Astragalus armatus subsp. numidicus (Murb.) Emb. & Maire.

A new acylated flavonol triglycoside, quercetin-3-O-(5'-p-hydroxybenzoyl)-ß-D-apiofuranosyl-(1→2)[α-L-rhamnopyranosyl-(1→6)]-ß-D-galactopyranoside (1), was isolated from the aerial parts of Astragalus armatus subsp. numidicus (Murb.) Emb. & Maire as well as ten known compounds, one phenolic compound, one flavonol-aglycone and eight flavonol-glycosides distributed into two monoglycosides, three diglycosides and three triosides. Their structures were mainly determined by 1D- and 2D-NMR experiments (1H,13C, COSY, HSQC, HMBC). The chloroform, ethyl acetate, n-butanol and hydroethanol extracts were tested for their antioxidant activity using five methods (DPPH, ABTS, Reducing power, CUPRAC and Phenanthroline). The ethyl acetate extract was the most active in CUPRAC (A0.5: 50.28 ± 2.16 µg/mL), ABTS (IC50: 49.73 ± 1.55 µg/mL) and Reducing power (A0.5: 58.13 ± 4.35 µg/mL) assays, whereas the hydroethanol and n-BuOH exhibited the highest activity in the Phenanthroline assay (A0.5: 9.93 ± 0.16) and (A0.5: 10.27 ± 0.44 µg/mL), respectively.

Biological activities and polyphenolic profile of Stachys arvensis (L.) L.

The n-butanol extract of Stachys arvensis (L.) L. aerial parts (BESA) was analysed by LC-HRMS/MS. 43 Polyphenols, including flavonoids, cinnamic acid derivatives, phenylethaoids, chromones, gallotannins, coumarins and chalcones with hyperoside (13.85%), panasenoside (10.31%), myricitrin (7.89%) and sayaendoside (7.16%), as the major compounds, were identified. High total phenolics (470.21 ± 1.22 mg GAE/g extract) and total flavonoids (189.05 ± 0.72 mg QE/g extract) contents were measured. In addition, the BESA exhibited a higher antioxidant effect in CUPRAC (A0.5:0.45 ± 0.03 µg/mL), DPPH (IC50:4.51 ± 0.16 µg/mL) and ABTS (IC50:7.10 ± 0.18 µg/mL) assays than the standards BHA and α-Tocopherol. Moreover the extract showed a good inhibitory effect against BChE (IC50: 145.02 ± 0.03 µg/mL) and α-amylase (IC50:2.66 ± 0.0024 mg/mL). The BESA exhibited an excellent anti-inflammatory activity (IC50:416 ± 0,056 µg/mL) which was close to that of acetylsalicylic acid, used as a control. The BESA was toxic towards T. molitor larvae and it possessed a good antibacterial activity against gram (+) and gram (-) tested strains.

A new triterpene saponin and known compounds from the polar extract of Salvia argentea L. and evaluation of their antioxidant activity.

A new triterpene saponin, 2, 3, 21, 23-tetrahydroxyolean-12-en-28-oic-acid-28-O-ß-D- glucosyl-(2''→1')-ß-D-glucoside (1), was isolated from the n-butanol extract of dried aerial parts of Salvia argentea L. (Lamiaceae) in addition to two known flavonoids, apigenin 7-O-ß-D-glucoside (2), threo-guaiacylglycerol 3-O-[6-O-p-hydroxybenzoyl]-ß-D-glucoside (3), luteolin 7-O-ß-D-glucoside (4), verbascoside (5) and rosmarinic acid (6). The structure elucidation of these compounds was based on analyses of spectroscopic data including 1D-, 2D-NMR and HR-ESI-MS techniques and by comparing their NMR data with those reported in the literature. Compound 6 exhibited the highest antioxidant activity in DPPH assay (IC50<3.00 µg/mL) which was better than the standards BHA, BHT, Trolox and ascorbic acid.

Antioxidant, Anti-Inflammatory and Anti-Proliferative Properties of Stachys circinata on HepG2 and MCF7 Cells.

According to the WHO, the overall age-standardized cancer rate keeps declining, and the number of cases diagnosed each year increases, remaining among the leading causes of death in 91 out of 172 recorded countries. In this context, novel cancer prediction and therapeutic protocols are compulsory. The effect of a Stachys circinata L'Hér dichloromethane extract (ScDME) on cell redox homeostasis and tumor proliferation was investigated. HepG2 cell feedback mechanisms to oxidative stress exposure were evaluated by determining catalase (CAT) and reduced glutathione (GSH), following the supply with ScDME (0.0-5.7 µg/µL). Cytotoxicity of ScDME against the human umbilical vein endothelial cell (HUVEC) and two human cancer cell lines (breast: MCF7; liver: HepG2) was evaluated by the MTT assay. H2O2-stressed HepG2 cells supplied with the S. circinata extracts exhibited significantly increased CAT and GSH activity as compared to unsupplied ones. The anti-inflammatory activity of the extracts was evaluated by real time-qPCR on IL-1, IL-6 and TNF-α expression. As a result, this research points out that S. circinata dichloromethane extract owns anti-inflammatory and anti-proliferative properties against MCF7 and HepG2 cells and activates CAT and GSH of the HepG2 cells' antioxidant enzyme system.

Evaluation of antiproliferative activity, apoptotic induction and LC-HRMS/MS analyses of the VLC fractions of L. numidicum.

In this study, six vacuum liquid chromatography (VLC) fractions (F1-F6) of the n-BuOH extract of L. numidicum Murb. (BELN) were examined for their anticancer capacity. The composition of secondary metabolites was analyzed by LC-HRMS/MS. The antiproliferative effect against PC3 and MDA-MB-231 lines was evaluated by MTT assay. Apoptosis of PC3 cells was detected by annexin V-FITC/PI staining using a flow cytometer. The results showed that only fractions 1 and 6 inhibited PC3 and MDA-MB 231 cell proliferation in a dose-dependent manner and induced dose-dependent apoptosis of PC3 cells, evidenced by the accumulation of early and late apoptotic cells, and by the decrease in viable cells. LC-HRMS/MS profiling of fractions 1 and 6 revealed the presence of known compounds that may be responsible for the observed anticancer activity. F1 and F6 may be an excellent source of active phytochemicals for cancer treatment.

Low concentrations of Ambrosia maritima L. phenolic extract protect endothelial cells from oxidative cell death induced by H2O2 and sera from Crohn's disease patients.

ETHNOPHARMACOLOGICAL RELEVANCE: A rising resort to herbal therapies in Crohn's disease (CD) alternative treatments has been recently observed due to their remarkable natural efficiency. In this context, the weed plant Ambrosia maritima L., traditionally known as Hachich el Aouinet in Algeria and as Damsissa in Egypt and Sudan, is widely used in North African folk medicine to treat infections, inflammatory diseases, gastrointestinal and urinary tract disturbances, rheumatic pain, respiratory problems, diabetes, hypertension and cancer. AIM OF THE STUDY: To assess an Ambrosia maritima L. phenolic extract for its phenolic profile composition, its potential antioxidant activity in vitro, and its cytoprotective effect on cultured primary human endothelial cells (ECs) stressed with H2O2 and sera from CD patients. MATERIALS AND METHODS: Phenolic compound extraction was performed with a low-temperature method. Extract chemical profile was attained by HPLC-DAD/ESI-MS. The extract in vitro antioxidant activity was assessed using several methods including cupric ion reducing power, DPPH radical scavenging assay, O-Phenanthroline free radical reducing activity, ABTS cation radical decolourisation assay, Galvinoxyl free radicals scavenging assay. Intracellular reactive oxygen species levels were evaluated in human endothelial cells by H2DCFDA, while cell viability was assessed by MTT. RESULTS: The phenolic compounds extraction showed a yield of 17.66% with three di-caffeoylquinic acid isomers detected for the first time in Ambrosia maritima L. Using different analytical methods, a significant in vitro antioxidant activity was reported for the Ambrosia maritima L. extract, with an IC50 value of 14.33 ± 3.86 µg/mL for the Galvinoxyl antioxidant activity method. Challenged with ECs the Ambrosia maritima L. extract showed a biphasic dose-dependent effect on H2O2-treated cells, cytoprotective and antioxidant at low doses, and cytotoxic and prooxidant at high doses, respectively. Viability and ROS levels data also demonstrated a prooxidant and cytotoxic effect of CD sera on cultured ECs. Interestingly, 10 µg/mL of Ambrosia maritima L. extract was able to counteract both CD sera-induced oxidative stress and ECs death. CONCLUSION: Our data indicated Ambrosia maritima L. as a source of bioactive phenolics potentially employable as a natural alternative for CD treatment.

Antiproliferative activity, cell-cycle arrest, apoptotic induction and LC-HRMS/MS analyses of extracts from two Linum species.

CONTEXT: Linum is the largest genus of the Linaceae family; the species of this genus are known to have anticancer activity. OBJECTIVE: In this study, ethyl acetate extracts of L. numidicum Murb. (EAELN) and L. trigynum L. (EAELT) were examined, for the first time, for their anticancer capacity. The secondary metabolites compositions were analysed by LC-HRMS/MS. MATERIALS AND METHODS: The antiproliferative effect of EAELN and EAELT (0-10.000 µg/mL) against PC3 and MDA-MB-231 cell lines were evaluated by the MTT assay after 72 h of treatment. Flow cytometer analysis of apoptosis (Annexin V-FITC/PI) and cell cycle (PI/RNase) was also performed after treatment with EAELN and EAELT at 250, 500, and 1000 µg/mL, for 24 h. RESULTS: EAELN had the highest antiproliferative activity against PC3 (IC50 133.2 ± 5.73 µg/mL) and MDA-MB-231 (IC50 156.9 ± 2.83 µg/mL) lines, EAELN had also shown better apoptotic activity with 19 ± 2.47% (250 µg/mL), 87.5 ± 0.21% (500 µg/mL), and 92 ± 0.07% (1000 µg/mL), respectively, causing cell cycle arrest of PC3 cells in G2/M phase, whereas arrest in G0/G1 and G2/M phases was observed after treatment with EAELT. LC-HRMS/MS profiling of the extracts revealed the presence of known compounds that might be responsible for the observed anticancer activity such as chicoric acid, vicenin-2, vitexin and podophyllotoxin-ß-d-glucoside. DISCUSSION AND CONCLUSIONS: We have shown, for the first time, that EAELN and EAELT exert anticancer activity through cell cycle arrest and induction of apoptosis. EAELN can be considered as a source to treat cancer. Further studies will be required to evaluate the effect of the active compounds, once identified, on other cancer cell lines.

Fisetin and Robinetin antiradical activity under solvent effect: density functional theory study.

The structural and antioxidant activity of two flavonols, namely, Fisetin and Robinetin, have been investigated employing the density functional theory (DFT) using B3LYP functional and 6-311++G (d, p) basis set. The calculations were performed in the gas phase and under the solvent effect of water, dimethylsulfoxide (DMSO), methanol, and benzene. The Hydrogen-Atom Transfer (HAT), single Electron Transfer Followed by Proton Transfer (SET-PT), and sequential Proton Loss Electron Transfer (SPLET) mechanisms were investigated to rationalize the radical scavenging capacities and to identify the favored antioxidant mechanism. Hence, the bond dissociation enthalpies (BDE) ionization potential (IP), IE, proton dissociation enthalpy (PDE), proton affinity (PA), and electron Transfer enthalpy (ETE) related to each mechanism were reported and discussed in function of the solvent effect. For both flavonols, the results showed that 4'-OH hydroxyl is the preferred active site following the trend 4'-OH > 3'-OH > 3-OH > (5'-OH) > 7-OH. Besides, the HAT mechanism is energetically the most favored pathway. The energetically favored solvents follow the trends water > DMSO > benzene > methanol and benzene > DMSO > methanol > water, for Fisetin and Robinetin, respectively.

In vitro and in vivo bioactivities of Ambrosia maritima and Bituminaria bituminosa organic extracts from Algeria.

INTRODUCTION: Two medicinal plants, Ambrosia maritima and Bituminaria bituminosa, growing in Algeria were investigated for their flavonoids content and their biological activities. METHODOLOGY: Different organic extracts were prepared from the aerial parts of each plant using maceration method followed by liquid/liquid type extractions. The anti-antioxidant activity was tested using the ß-carotene bleaching method. The anti-inflammatory activity was tested by performing the protein anti-denaturation assay. Acute toxicity and immunostimulatory effect were tested in mice, while the antimicrobial activity was tested according to the minimal inhibition concentration technique. RESULTS: In term of flavonoids content, ethyl acetate extract of B. bituminosa was the highest (193.39 ± 24.1 µg QE/mg). Ethyl acetate extract of A. maritima showed antioxidant activity with IC50 value of 11.72 ± 0.79 µg/mL. The hydroethanolic extract of A. maritima showed the best anti-denaturation effect in a dose-dependent manner with the IC50 value of 131.07 ± 0.027 µg/mL. The studied plants showed no toxicity or mortality in vivo. Both plants showed a significant immunostimulatory effect; while the Butanolic extract of B. bituminosa demonstrated the best antimicrobial activity against Staphylococcus aureus and Candida albicans strains. CONCLUSIONS: We recommend A. maritima and B. bituminosa as potent sources of antioxidants and as antimicrobial agents for further assays to better elucidate their actions on the immune system.

Triterpenoid saponins from Anagallis monelli ssp. linifolia (L.) Maire and their chemotaxonomic significance.

Thirteen undescribed triterpenoid saponins named monellosides A-M, were isolated from the aerial parts of Anagallis monelli ssp. linifolia (L.) Maire, together with ten known oleanane-type glycosides. Their structures were elucidated by 1D and 2D-NMR spectroscopy (COSY, TOCSY, HSQC, HMBC and ROESY) as well as high resolution mass spectrometry (HR-ESI-MS) and acid hydrolysis. Monellosides A-M have a carbohydrate chain linked on the C-3 of the aglycone with a common ß-d-glucopyranosyl-(1 â†’ 4)-α-l-arabinopyranosyl sequence which was further glycosylated by a glucose and/or a xylose. The sequence ß-d-xylopyranosyl-(1 â†’ 2)-ß-d-glucopyranosyl-(1 â†’ 4)-[ß-d-glucopyranosyl-(1 â†’ 2)-]α-l-arabinopyranosyl was common to all the 13,28-epoxy-oleanane core skeleton except one compound. In order to discuss the reclassification of Anagallis in Primulaceae, we compared saponins from species of Myrsinaceae and Primulaceae families and showed that these species were characterized by a pentacyclic triterpenoid saponin with a 13,28-epoxy bridge skeleton. Our phytochemical results increase the knowledge of saponins of the genus Anagallis, their chemotaxonomy and stimulate the evaluation of the biological activities of these saponins.

Chemical composition and biological potential of Thymus Willdenowii Boiss. & Reut. essential oil.

The fresh aerial parts of Thymus willdenowii Boiss. & Reut. (syn. Thymus hirtus Willd.) were hydrodistilled in a Clevenger type apparatus and analyzed by GC and GC-MS. 44 Components were identified representing 97.3%, with 1,8-cineole (34.62%), camphor (18.55%), α-pinene (9.46%) and camphene (5.38%) as the main components. T. willdenowii essential oil was not cytotoxic (CC50 = 97.65 µg/mL) towards Vero non-tumoural cells, exhibiting good antibacterial and antiproliferative (30.8 ± 3.1% inhibition) potentials against four tested pathogenic bacteria and Human colorectal cell line HT-29, respectively. The essential oil did not show a DPPH radical scavenging activity, by Electron Spin Resonance spectroscopy (ESR), and it lacks antiviral effect towards coxsackievirus B3.

Antioxidant activity and characterization of flavonoids and phenolic acids of Ammoides atlantica by RP-UHPLC-ESI-QTOF-MSn.

In this study, phytochemical profiling of hydro-alcoholic extract of Ammoides atlantica aerial parts has been carried out using RP-UHPLC-ESI-QTOF-MS in negative ionization mode Chemical characterization was established according to the MS and MS/MS spectra. A total of 66 chemical compounds were detected. Among these, 45 compounds were identified: hydroxycinnamic acid and derivatives (26), hydroxybenzoic acids (4), flavones (11), flavonols (3), and a lignan. Total phenolics (371.57 mg/g) and total flavonoids (41.02 mg/g) contents were also determined. Moreover, the antioxidant activity of A. atlantica extract was also studied by six methods: DPPH (IC50: 23.31 µg/mL), ABTS+ (IC50: 11.31 µg/mL), O2- DMSO alkaline (IC50: 3.19 µg/mL), ferrous ions chelating assays (IC50: 102.35 µg/mL), reducing power (A0.50: 92.70 µg/mL) and CUPRAC (A0.50: 13.56 µg/mL) assays. These results suggest that the antioxidant activity of the hydroalcoholic extract was comparable to common antioxidant additives in most of the tests, representing a good alternative.

Behavioral and neurological improvement by Cydonia oblonga fruit extract in chronic immobilization stress rats.

It is known that chronic stress is a contributing factor to several physical and mental diseases. In this study, we examined the effect of hydroethanolic extract of Cydonia oblonga fruit (HECO, 300 mg/kg) in chronically immobilized rats on physiological and behavioral parameters by the open field test (OFT), sucrose preference test (SPT), and forced swimming test (FST) and on neurological alterations by analysis of the hippocampal neurogenesis. A daily 6 hr exposure to chronic immobilization stress (CIS) for 21 consecutive days induced anxiety- and depressive-like behaviors in rats' concomitant with decreased weight gain and increased plasma corticosterone (CORT) levels, rats also showed atrophy in the CA3 subregion of the hippocampus and a decreased number of Ki67 and DCX positive cells in the dentate gyrus (DG). Treatment with HECO successfully suppressed the physiological and behavioral markers of the CIS and prevents the structural abnormality and the impaired cell proliferation in the hippocampus. Moreover, the daily administration of HECO improved the mood function in normal rats. Taking together, our findings demonstrate, for the first time, the anti-depressive effect of C. oblonga fruit by enhancing the hippocampal neurogenesis in the rat model of depression.

Semipapposides A-M, triterpenoid bidesmosides saponins from the roots of Scabiosa semipapposa.

Phytochemical investigations of the roots of Scabiosa semipapposa Salzem ex D.C. have led to the isolation of 12 undescribed triterpenoid saponins named semipapposides A-L, one undescribed saponin semipapposide M obtained as an inseparable mixture, together with three known oleanolic acid glycosides. Their structures were elucidated by analysis of 1D and 2D-NMR (1H-1H COSY, TOCSY, HSQC-TOCSY, HSQC, ROESY or NOESY, and HMBC) spectroscopic data and mass spectrometry (HR-ESI-MS), and by comparison with those of related metabolites. All saponins possess a partial sequence rhamnopyranosyl-(1 â†’ 2)-xylopyranosyl or rhamnopyranosyl-(1 â†’ 2)-arabinopyranosyl- at C-3 of the aglycon and a gentiobiose unit at C-28. These results represent a contribution to the knowledge of the saponins of Scabiosa species and their chemotaxonomy.

Triterpene saponins from Silene gallica collected in North-Eastern Algeria.

Eleven previously undescribed triterpene saponins, named silenegallisaponin A-K (1-11), were isolated from the aerial parts of Silene gallica L. Their structures were elucidated by analysis of 1D and 2D-NMR spectroscopic data and mass spectrometry (HR-ESI-MS). The saponins comprised caulophyllogenin, echinocystic acid, or quillaic acid substituted at C-3 by a ß-d-glucuronic acid or ß-d-galactopyranosyl-(1 â†’ 3)-ß-d-glucuronopyranoside and at C-28 by a ß-d-fucopyranose substituted at C-2 by a ß-d-glucose and at C-3 by a ß-d-glucose or a ß-d-quinovose.