Nigella Glandulifera Research Articles

Proposed total synthesis of the potential antidiabetic compound 5,7-dihydroxy-6-(3-methybut-2-enyl)-isobenzofuran-(13H)-one

Insulin analogs are currently the most often prescribed medications for treating type 2 diabetes mellitus (T2DM). However, because of the inherent flaws of the medications and the restrictions of the administration methods, there is no comprehensive plan for managing diabetes. As a result, its crucial to research comprehensive treatment plans based on the available medications and the traits of T2DM. Natural products play as key role in drug discovery. Although many articles have been published on the antidiabetic potential of natural products, few natural product-based molecules have been approved for the treatment of T2DM. It has been established that the compound 5,7-dihydroxy-6-(3-methybut-2-enyl)-isobenzofuran-(13H)-one from Nigella glandulifera Freyn et Sint (N. glandulifera) possesses antidiabetic activity, but little attention has been dedicated to its total synthesis. Herein, we attempt to reveal a new total synthesis of 5,7-dihydroxy-6-(3-methybut-2-enyl)-isobenzofuran-(13H)-one. The synthesis is simple, with few steps, and has potential for industrialization.

Ameliorative effect of scopolamine-induced cognitive dysfunction by Fufangmuniziqi formula: The roles of alkaloids, saponins, and flavonoids

Ethnopharmacological relevanceFufangmuniziqi formula (FFMN), a traditional Uyghur medicine used in China, is derived from an ancient Uyghur medical book and consists of 13 herbs. The herbs of FFMN, such as Peganum harmala L., Glycyrrhiza uralensis Fisch., and Nigella glandulifera, have been demonstrated to have acetylcholinesterase (AChE) inhibitory, anti-neuroinflammatory, or antioxidant effects. Therefore, FFMN may have a good anti-Alzheimer's disease (AD) effect, but its specific action and mechanism need to be further proven. Aim of the studyThis study aims to investigate the anti-AD effects of FFMN and the role played by alkaloids, flavonoids, and saponins in anti-AD. Materials and methodsThe alkaloids, flavonoids, and saponins fractions of FFMN were prepared by macroporous resin chromatography. The absorbed ingredients in the drug-containing serum were identified by UPLC⁃Q⁃TOF⁃MS. An AD mouse model was established by intraperitoneal injection of scopolamine (SCO). The role of different fractions of FFMN in the anti-AD process was examined by Morris water maze (MWM), in-vitro cell, and AChE inhibition assay. ResultsA total of 20 ingredients were identified in the serum samples collected after oral administration of FFMN, and seven compounds were selected as candidate active compounds. MWM experiments showed that different fractions of FFMN could significantly improve SCO-induced learning memory impairment in mice. The alkaloids fraction (ALK) regulated cholinergic function by inhibiting AChE activity, activating choline acetyltransferase activity, and protein expression. Flavonoids and saponins were more potent than the ALK in downregulating pro-inflammatory factors or inflammatory mediators, such as TNF-α, MPO, and nitric oxide. Western blot results further confirmed that flavonoids and saponins attenuated neuroinflammation by inhibiting the phosphorylation of IκB and NF-κB p65. This result was also verified by in-vitro cellular assays. FFMN enhanced antioxidant defense by increasing the activity of superoxide dismutase and reducing the production of MDA. Combined with cellular experiments, flavonoids and saponins were proven more protective against oxidative damage. ConclusionFFMN improved cognitive and memory impairment in the SCO-induced AD mouse model. ALK mainly enhanced the function of the cholinergic system. Flavonoid and saponin fractions mainly attenuated neuroinflammation and oxidative stress by modulating the NF-κB pathway. All these findings strongly suggested that the combination of alkaloid, flavonoid, and saponin fractions derived from FFMN is a promising anti-AD agent that deserves further development.

Total Saponins from Nigella glandulifera Seeds Ameliorate Adjuvant-Induced Rheumatoid Arthritis in Rats by Inhibition of an Inflammatory Response and Bone Erosion.

Rheumatoid arthritis (RA) is a widespread inflammatory disease whose clinical manifestations are joint swelling, pain, and disability, affecting approximately 1% of individuals worldwide. Conventional anti-RA drugs currently used in clinic have severe side effects. The present study is aimed at investigating the antiarthritic effects of total saponins from Nigella glandulifera seeds (TSNGS) in rats with adjuvant-induced rheumatoid arthritis (AIA). Arthritis score, paw swelling, and body weight were monitored throughout the period of TSNGS treatment. The histopathological features and levels of cytokines, including IFN-γ, TNF-α, IL-1β, IL-4, IL-6, IL-10, and IL-17A, and OPG/RANKL signaling, were measured to determine the amelioration by TSNGS and its potential mechanisms on the inflammatory response and bone erosion. The differentiation of regulatory T cells (Tregs) in serum was assessed by flow cytometry. The results demonstrate that TSNGS at 10 mg/kg, 50 mg/kg, and 250 mg/kg inhibited AIA-induced clinical score, paw swelling, and histological changes. TSNGS reduced the immune-inflammatory reaction by restoring the secretion and expression of inflammatory cytokines and elevating the proportion of CD4+ CD25+ Tregs, accompanied by an increase in transcription factor Foxp3 levels. TSNGS also displayed bone protection by upregulation of the OPG/RANKL pathway. Collectively, TSNGS inhibited arthritis in AIA rats and so represents a potential novel treatment for RA.

Nigella A ameliorates inflammation and intestinal flora imbalance in DSS induced colitis mice

Nigella A, also named Sieboldianoside A, has been extracted from many kinds of Traditional Chinese Medicine (TCM), such as Nigella glandulifera, Stauntonia chinensis DC., and the leaves of Acanthopanax sieboldianus. Nigella A exhibited potential analgesic, anti-inflammatory, anti-tumor, and antioxidant activities. However, whether Nigella A could treat ulcerative colitis (UC) is still unknown. As saponins always be regarded as the kinds of ingredients that could regulate immunity and intestinal flora. This research aimed to investigate the therapeutic effect of Nigella A on UC and explore its effect on intestinal flora. We noted that Nigella A and Sulfasalazine (SASP) could significantly improve the signs and symptoms, alleviate colonic pathological injury in DSS-induced mice. The changing of many specific bacterial genus such as Lactobacillus, Porphyromonadaceae, Bacteroides and Escherichia might closely related to the recovery of intestinal inflammatory response. This study initially confirmed the therapeutic effect of Nigella A and SASP on DSS-induced colitis by improving the diversity of intestinal microbial composition. Nigella A has the potential to be developed for the treatment of UC and other disorders related to the imbalance of intestinal flora.

Optimization of microwave-assisted extraction using response surface methodology and the potential anti-diabetic efficacy of Nigella glandulifera Freyn determined using the spectrum–effect relationship

Nigella glandulifera Freyn belongs to the Ranunculaceae family of plants. It is an annual herbaceous plant widely distributed in the southwest and western regions of China. The seeds and oil of N. glandulifera have been used as a medicine to treat a variety of diseases. Unfortunately, the extraction of bioactive components and their inherent phytochemical characterization is rarely investigated using optimum condition of emerging extraction. In the study, we compared the microwave-assisted method to traditional extraction methods, which has the shortest time, highest yield and greatest biological activity. We performed single factor experiments with comprehensive assessments and used Box-Behnken design with a response surface methodology to assess the optimal conditions. The optimal extraction method was as follows; solid-to-liquid ratio of 1:20 g/mL, ethanol concentration of 70%, extraction time of 35.00 min, and extraction temperature of 66 °C. Using these conditions, we further analyzed the spectrum–effect relationship using gray correlation and chemical composition using ultra-high-performance liquid chromatography coupled with high resolution hybrid quadruple-orbitrap mass spectrometry (UHPLC-Q-Orbitrap-HRMS). Therefore, the gray relationship of 17 compounds was analyzed greater than 0.95 which may have synergistic effects on the inhibiting of aldose reductase. In addition, thirty compounds were identified, including alkaloids, flavonoid glucosides, triterpenoid saponins and phenolic compounds, all of which may have a therapeutic effect on diabetic complications. The results of this study may offer a time-saving and convenient method to acquire bioactive components to improve and treat diabetic complications.

Hydrolysis product of Nigella A obtained from Nigella glandulifera Freyn seeds promotes apoptosis and AMPK-mediated autophagy in human colon cancer SW620 cells

Nigella B (NB) is the hydrolysis product of Nigella A (NA), which is extracted from the seeds of Nigella glandulifera Freyn. NB has several beneficial characteristics, including antiproliferative activity against several cancer cell lines. In this study, we analyzed the in vitro and in vivo anticancer activity of both NA and NB as well as the potential molecular mechanisms behind the actions of NB. We found that NB treatment led to autophagy and soft apoptosis in colon cancer cells (SW620). NA treatment had no effect on either. Further study showed that NB treatment in SW620 cells led to inhibited phosphorylated mammalian target of rapamycin (p-mTOR) expression but increased phosphorylated-5? adenosine monophosphate protein kinase (AMPK) expression, a key regulator of autophagy. This suggests that the AMPK-mTOR pathway plays a crucial role in autophagy induction. Separate in vivo studies using NA (40 mg/kg, intragastric administration (i.g.)) and NB (40 mg/kg, i.g.) resulted in inhibited tumor growth in nude mice by 42.82% and 37.20% respectively, when compared with vehicle-administered animals. In vitro tumor protein expression was consistent with its expression in vitro. Taken together, our results reveal an anticancer function for NA and NB in colon cancer and support the use of NA as an antitumor prodrug, and NB as a novel therapeutic drug.

Pyrrolo-isoquinoline and glycosylated pyrrolidine alkaloids from Nigella glandulifera and their anti-PTP1B activity

Two new alkaloids, nigellisoquinomine (1) with a novel pyrrolo-isoquinoline skeleton, and nigellapyrrolidine (2) possessing a rare glycosylated pyrrolidine moiety, together with two known alkaloids, agrocybenine (3) and 4,6,6-trimethyl-3,4-epoxypiperidin-2-one (4), were isolated from the seeds of Nigella glandulifera Freyn. Their structures were identified by extensive NMR and HR-ESIMS analysis. Compound 1 exhibited potent protein tyrosine phosphatase 1B (PTP1B) inhibitory activity with an IC50 value of 3.65±0.08μM.

Anti-diabetic effect of three new norditerpenoid alkaloids in vitro and potential mechanism via PI3K/Akt signaling pathway.

Diabetes is a metabolic disease with the characteristic of high blood glucose (hyperglycemia). In our previous study, we found that nigelladines A-C (compounds A-C), three norditerpenoid alkaloids from the seeds of Nigella glandulifera Freyn (Ranunculaceae) exhibited protein of tyrosine phosphatase 1B (PTP1B) inhibitory activity in vitro. In the present study, we further investigated their anti-diabetes activities in L6 moytubes and illuminated the mechanisms of action of compounds A-C. Several parameters of glucose metabolism such as glucose consumption, glycogen content and hexokinase activity were increased by compounds A-C. The results suggested that compounds A-C improved glucose metabolism through promoting synthesis of glycogen. Expression of PTP1B protein was inhibited by compounds A-C in L6 moytubes. PI3K-dependent Akt phosphorylation was found to be activated by compounds A-C and completely blocked by wortmannin (a PI3K inhibitor). Moreover, the insulin-mediated induction of insulin receptor substrate-1 (IRS-1) and glycogen synthase kinase-3β (GSK-3β) were also suppressed by wortmannin. Western blot results indicated that compounds A-C-induced IRS-1/Akt activation was likely a consequence of PTP1B inhibition. Compounds A-C promoted glycogen synthesis through Akt-mediated GSK3 phosphorylation. Therefore, activation of PI3K/Akt insulin signaling pathway and suppression of PTP1B is the molecular mechanism that contributes to the anti-diabetic effect of compounds A-C in cellular models. The three alkaloids potentially serve as lead compounds for the development of antidiabetic drugs.

Development and validation of liquid chromatography-tandem mass spectrometry method for quantification of a potential anticancer triterpene saponin from seeds of Nigella glandulifera in rat plasma: application to a pharmacokinetic study.

Nigella glandulifera Freyn et Sit is a folk medicinal plant, whose seeds show significant anticancer activities attributed to triterpene saponins and volatile oil. In this study, an in vitro cytotoxicity assay demonstrated that Nigella A, the major component of triterpene saponins extracted from N. glandulifera, exhibited growth inhibition in the human lung carcinoma A-549 cell line. Due to this potential activity, a reliable liquid chromatography-tandem mass spectrometry (LC-MS/MS) method to quantify Nigella A in rat plasma for a pharmacokinetic study was developed. Nigella A and pravastatin, as internal standard (IS), were extracted from rat plasma using acetonitrile to precipitate protein. Separation was performed on an Agilent Zorbax SB-Aq (3.0 × 150 mm, 3.5 μm) column using a gradient elution method with acetonitrile-0.1% formic acid in water at a flow rate of 0.35 mL/min. Detection was performed using an electrospray ionization in a negative ion multiple reaction monitoring mode. The deprotonated precursor to product ion transitions monitored for Nigella A and IS was at m/z 1352.7→882.6 and m/z 423.1→321.0, respectively. The linear range was 0.240-120 μg/mL with a square regression coefficient (r=0.9996). The intra-day and inter-day precision was less than 6.93%. The simple extraction procedure provided recovery ranged from 92.32 to 95.44% for both analyte and IS. The method was proved to be reliable, precise, and accurate, and was successfully applied to a pharmacokinetic study of Nigella A in rats after i.v. administration via the tail vein at doses of 10, 20, and 30 mg/kg.

Highly Conjugated Norditerpenoid and Pyrroloquinoline Alkaloids with Potent PTP1B Inhibitory Activity fromNigella glandulifera

Three norditerpenoid alkaloids, nigelladines A-C (1-3), and one pyrroloquinoline alkaloid, nigellaquinomine (4), all possessing new skeletons with highly conjugated systems, were isolated from Nigella glandulifera. The 8aS-configuration for 1 and 2 was determined by comparison of the experimental and calculated electronic circular dichroism spectra. These alkaloids exhibited potent protein tyrosine phosphatase 1B (PTP1B) inhibitory activity but are devoid of cytotoxicity against the A431 cell line at 100 μM.

Anti‐Inflammatory Effects of 81 Chinese Herb Extracts and Their Correlation with the Characteristics of Traditional Chinese Medicine

Inducible nitrogen oxide synthase (iNOS) is the primary contributor of the overproduction of nitric oxide and its inhibitors have been actively sought as effective anti-inflammatory agents. In this study, we prepared 70% ethanol extracts from 81 Chinese herbs. These extracts were subsequently evaluated for their effect on nitrogen oxide (NO) production and cell growth in LPS/IFNγ-costimulated and unstimulated murine macrophage RAW264.7 cells by Griess reaction and MTT assay. Extracts of Daphne genkwa Sieb.et Zucc, Caesalpinia sappan L., Iles pubescens Hook.et Arn, Forsythia suspensa (Thunb.) Vahl, Zingiber officinale Rosc, Inula japonica Thunb., and Ligusticum chuanxiong Hort markedly inhibited NO production (inhibition > 90% at 100 μg/mL). Among active extracts (inhibition > 50% at 100 μg/mL), Rubia cordifolia L., Glycyrrhiza glabra L., Iles pubescens Hook.et Arn, Nigella glandulifera Freyn et Sint, Pueraria lobata (Willd.) Ohwi, and Scutellaria barbata D. Don displayed no cytotoxicity to unstimulated RAW246.7 cells while increasing the growth of LPS/IFNγ-costimulated cells. By analyzing the correlation between their activities and their Traditional Chinese Medicine (TCM) characteristics, herbs with pungent flavor displayed potent anti-inflammatory capability. Our study provides a series of potential anti-inflammatory herbs and suggests that herbs with pungent flavor are candidates of effective anti-inflammatory agents.

Botanicals in Dietary Supplements

Botanicals are accepted worldwide as medicinal agents and nutraceuticals. Extensive scientific investigations have been performed over the past 200 years which have resulted in the evolution of botanical utilization. This special issue highlights some of this research in 7 review articles and in 24 original research articles. Review Articles. W. Jiratchariyakul and G. B. Mahady wrote about the botanical status and popular herbs in EU, US, and Thailand. M. Miroddi et al. updated the market and the regulatory of botanical products in EU and US. Traditional Chinese and Indian Medicines (TCM and TIM) play an important role in Asian countries. Z. Wang et al. presented and discussed the role of TCM in the treatment of epidemic type II diabetes mellitus. M. M. Pandey et al. reported the use of TIM as a nutritional supplement in malnutrition. Y. Kamisah et al. presented the chemoprevention and antioxidation of Parkia speciosa. A. P. Bartolome et al. reviewed laboratory evidence of Bidens pilosa. T.-P. Huynh et al. discussed the promising botanical compounds for prevention and treatment of eye diseases. Research Articles. New biological and pharmacological activities of botanicals are reported. They included the enhancement of learning, memory and antistress of Acanthopanax trifoliatus (P. Sithisarn et al.), the sedative effect of Ziziphus mauritiana (A. M. M. San et al.), the cardioprotective effect of Phyllanthus emblica (L. Chularojmontri et al.), the cytoprotection and antioxidative stress of Citrus maxima (L. Chularojmontri et al.), anti-influenza viral activity of Momordica charantia (V. Pongthanapisith et al.), antioxidation from Nypa fruticans (N. Prasad et al.), Nigella glandulifera (J. Zhao et al.), TIM (M. M. Pandey et al.), Herba Cynomorii (J. Chen et al.). The alleviation of metabolic disorder of Citrus ichangensis (X. Ding et al.), and anticancer activity of Vitex agnus-castus (S. Li et al.). The mechanisms of anticancer action are deeply investigated with the botanical compounds, zerumbone from Zingiber zerumbet (N. M. Nadzri et al.), phenyl butenoid dimmer from Zingiber cassumunar (T. Anasamy et al.), and girinimbine from Murraya koenigii (S. Mohan et al.). Biochanin A, the major isoflavone from Trifolium pratense, prevented the bone loss in the ovariectomized rat (S.-J. Su et al.). Quercetin isolated from Caesalpinia mimosoides had neuroprotective effect (N. Tangsaengvit et al.) and inhibited eosinophile (M. K. Asano Sakai-Kashiwahara). C. Li et al. reported new anti-inflammatory triterpenoids from Illicium difengpi. Besides the herbal activities, the cohort study of TCM, Si-Wu-Tang, in postpartum women was performed to evaluate the health benefits. The effectiveness of the modern herbal drug was carried out using the double-blind randomized controlled clinical trial, as shown under the title “Antiherpetic effects of Gynura procumbens” (S. Jarikasem et al.). The research on the quality assessment of the botanicals was also presented in this issue. It included the HPLC analysis of Moringa oleifera (B. Vongsak et al.) and Pueraria tuberosa (S. Rastogi et al.). In addition, the arsenic accumulation in Zingiberaceous rhizomes was reported (C. Ubonnuch et al.). Weena Jiratchariyakul Ludger Beerhues Gail B. Mahady Tanawan Kummalue Molvibha Vongsakul

Immunomodulatory and anti-tumor effects ofNigella glanduliferafreyn and sint seeds on ehrlich ascites carcinoma in mouse model

Aim:This study investigated the immunomodulatory and anti-tumor effects of Nigella glandulifera Freyn and Sint seeds (NGS) on Ehrlich ascites carcinoma in a mouse model.Materials and Methods:Kunming mice with transplanted Ehrlich ascites tumor cells (EAC) were treated with NGS by oral administration. On the 11th day after the EAC implant, mouse thymus, liver, spleen and kidney tumors were removed for histopathological analysis. Blood samples were taken for hematological and biochemical analyses.Results:The results indicate that NGS treatment leads to an increase in TNF-α, IL-1β, and IL-2 blood serum levels. Absence of viable EAC and presence of necrotic cells were observed in the tumor tissue of the NGS-treated animals.Conclusions:The study results indicated that a water extract of NGS had the highest anti-tumor effect. Moreover, NGS treatment also showed an increase in the immune system activity.

A Spotlight on Chemical Constituents and Pharmacological Activities of Nigella glandulifera Freyn et Sint Seeds

Plants belonging to the Ranunculaceae family, and particularly their seeds, have been a hot research topic in numerous pharmacognosy laboratories. Nigella glandulifera Freyn et Sint (NG) is one of the promising, but relatively insufficiently studied, plants from this family. In this review, we summarize the recently isolated chemical constituents from the seeds of this plant including alkaloids, flavonol glycosides, isobenzofuranone derivatives, saponins, terpenes, terpenoids, and fatty acids. We put also a spotlight on the recently studied therapeutic potentials of such amazing herb seeds as antidiabetes, melanogenesis inhibition, anticancer, anti‐inflammatory, antithrombosis, and antiplatelet aggregation effects. Herein, we illustrate certain properties and potentials via selected examples, and thus we suggest more studies to confirm the therapeutic hypotheses, find out new compounds, and eventually to discover novel properties.

Response Surface Optimization of Nigella glandulifera Freyn Seed Oil Yield by Supercritical Carbon Dioxide Extraction

Supercritical carbon dioxide (SC-CO2) extraction was employed to extract oil from Nigella glandulifera Freyn seed in this study. Response surface methodology (RSM) was applied to evaluate the effects of the process parameters (pressure, temperature, and CO2 flow rate) on oil yield of N. glandulifera seed. A Box-Behnken design was used to optimize the extraction parameters. The analysis of variance indicated that the linear coefficients of pressure and CO2 flow rate, the quadratic term coefficients of pressure and temperature and the interactions between pressure and temperature, as well as temperature and CO2 flow rate, had significant effects on the oil yield (P<0.05). The optimal conditions to obtain the maximum oil yield from N. glandulifera seed were pressure 30.84 MPa, temperature 40.57°C, and CO2 flow rate 22.00 L h−1. Under these optimal conditions, the yield of oil was predicted to be 38.19%. The validation experiment results agreed with the predicted values. The fatty acid composition of N. glandulifera seed oil extracted using SC-CO2 was compared with that of oil obtained by Soxhlet method. The results showed that the fatty acid compositions of oil extracted by the two methods were similar. Identification of oil compounds with gas chromatography-mass spectrometry (GC-MS) showed that the contents of unsaturated fatty acids linoleic acid (48.30%), oleic acid (22.28%) and saturated fatty acids palmitic acid (16.65%), stearic acid (4.17%) were the most abundant fatty acids in seed oil from N. glandulifera

Identification of depigmenting components from Nigella glandulifera Freyn

To develop a novel skin depigmenting agent from natural sources, the inhibition of melanogenesis by Chinese plants, N. glandulifrea, was evaluated. The methanol extract of this plant showed significantly down-regulated melanin synthesis in a dose-dependent manner at a non-toxic concentration in cultured B16F10 mouse melanoma cells. This extract was further fractionated by using solvent-solvent partition and silica open column chromatography to identify the active components. From GC-MS data, oleic acid methyl ester was found as one of the depigmenting agents. In conclusion, we suggest that this fraction may be a safe and effective depigmentation agent.

ANTIDIABETES PROPERTIES OF n-HEXANE AND PETROLEUM ETHER EXTRACTS FROM SEEDS OF NIGELLA GLANDULIFERA FREYN

Nigella glandulifera Freyn, an annual plant species of the family Ranunculaceae, served as a traditional Uigur medicine and food. Many researchers have reported that Nigella sativa L., which is the same genus with it, has an antidiabetic effect, the seeds oil was an activity component used as a kind of function food. In the present study, the difference of oil extract between n-hexane and petroleum ether respectively from the seeds of Nigella glandulifera Freyn were analyzed by gas chromatography-mass spectrometry, all of them can inhibit protein tyrosine phosphatase 1B (PTP1B) with half maximal inhibitory concentration values of 33.15 ± 0.77 and 18.50 ± 0.52 μg/mL, respectively. They have different binding sites with PTP1B. Lastly, inhibited ability of PTP1B and that of TCPTP were compared; all of them have shown some selectivity.

Preparative isolation and purification of isobenzofuranone derivatives and saponins from seeds of Nigella glandulifera Freyn by high-speed counter-current chromatography combined with gel filtration

Although the medicinal plant and food Nigella glandulifera Freyn has been researched for decades, isobenzofuranones have never been isolated before. Two isobenzofuranone derivatives and two saponins were successfully separated and purified from seeds of N. glandulifera Freyn by high-speed counter-current chromatography (HSCCC) with the optimized two-phase solvent system, n-hexane-ethyl acetate–methanol–water (7:3:5:5, v/v). Salfredin B 11 (22.1 mg, HPLC purity 95.3%), 5, 7-dihydroxy-6-(3-methybut-2-enyl) isobenzofuran-1(3H)-one (18.9 mg, HPLC purity 97.3%) and crude sample 2 (555 mg) were separated from 600 mg of ethyl acetate extract of N. glandulifera Freyn. Following a cleaning-up step by chromatography on Sephadex LH-20, hederagenin (12 mg) and 3-O-[β- d-xylopyranosyl-(1 → 3)-α- l-rhamnopyranosyl-(1 → 2)-α- l-arabinopyranosyl]-hederagenin (45 mg) were separated from sample 2. All of the fractions before peak II were collected and subjected to a Sephadex LH-20 column and eluted by methanol, two of triterpene saponins (12 mg of hederagenin and 45 mg of 3-O-[β- d-xylopyranosyl-(1 → 3)-α- l-rhamnopyranosyl-(1 → 2)-α- l-arabinopyranosyl]-hederagenin) were isolated. The structures of peak fractions were identified by IR, electron ionization MS, 1H NMR and 13C NMR. 5, 7-Dihydroxy-6-(3-methybut-2-enyl) isobenzofuran-1(3H)-one was isolated for the first time from higher plant and salfredin B11 was isolated for the first time in this plant.

Flavonoids and phenolic compounds from seeds of the Chinese plant Nigella glandulifera

Flavonoids and phenolic compounds from seeds of the Chinese plant Nigella glandulifera

Triterpene saponins from seeds of the Chinese plant Nigella glandulifera

Triterpene saponins from seeds of the Chinese plant Nigella glandulifera