Quassinoids from seeds of Brucea Javanica and their anticomplement activities

Abstract

An investigation on seeds of Brucea javanica led to the acquisition of a new quassinoid, 20-hydroxyyadanzigan (1), along with five known quassinoids (2–6). The structure of the new compound was elucidated on the basis of extensive spectral analysis. All of the compounds were assayed for their anticomplement activities through classical and alternative pathways. Compounds 1–6 exhibited potent anticomplement activity with CH₅₀ and AP₅₀ values of 0.032–0.075?mg/mL and 0.061–0.118?mg/mL, respectively. Moreover, the structure-activity relationships of these compounds are discussed.

     

A Novel Canthin-6-One Alkaloid Isolated from Cell Suspension Cultures of Brucea Javanica (L.) Merr

During investigation of cell suspension cultures of Brucea javanica (L.) Merr., the canthin-6-one alkaloid 5,11-dimethoxycanthin-6-one (1) was isolated. The structural determination is based on spectral analysis. Five other alkaloids, canthin-6-one-3-N-oxide (2), 11-hydroxycanthin-6-one (3), canthin-6-one (4), 5-methoxycanthin-6-one (5), and 11-methoxycanthin-6-one (6), were also identified.     

Medicinal Activities and Nanomedicine Delivery Strategies for Brucea javanica Oil and Its Molecular Components

Brucea javanica oil (BJO) is widely used in traditional Chinese medicine to treat various types of cancer and inflammatory diseases. There is significant interest in understanding the medicinal activities of BJO and its molecular components, especially quassinoids, and in exploring how they can be incorporated into nanomedicine delivery strategies for improved application prospects. Herein, we cover the latest progress in developing different classes of drug delivery vehicles, including nanoemulsions, liposomes, nanostructured lipid carriers, and spongosomes, to encapsulate BJO and purified quassinoids. An introduction to the composition and medicinal activities of BJO and its molecular components, including quassinoids and fatty acids, is first provided. Application examples involving each type of drug delivery vehicle are then critically presented. Future opportunities for nanomedicine delivery strategies in the field are also discussed and considered within the context of translational medicine needs and drug development processes.     

Coumarinolignans Isolated from the Seeds of Brucea javanica

A new coumarinolignan, cleomiscosin E ( 1 ), together with the known compound cleomiscosin A ( 2 ), has been isolated from the seeds of Brucea javanica (L.) Merr . Their structures were assigned on the basis of spectral studies. These two compounds exhibited potent anti‐inflammatory activities by inhibiting the nitric oxide (NO) production in lipopolysaccharide (LPS)‐activated RAW264.7 macrophages.     

Bioactive triterpenoids from Sambucus javanica Blume

Abstract

A new triterpene, javablumine A (1) along with six known ones were isolated from the aerial parts of Sambucus javanica Blume. They were identified as 3β,23-dihydroxy-11α,12α-epoxy-urs-20(30)-en-28,13β-olide (1), ursolic acid (2), pomolic acid (3), oleanic acid (4), 2α-hydroxy-oleanolic acid (5), α-amyrin (6), and lupeol palmitate (7), respectively. Compounds 1 and 3 exhibited inhibitory effect against nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW264.7 macrophage cell lines with IC₅₀ values of 17.4 and 26.2?μM, respectively.     

Herbicidal activity and bioactive components of Brucea javanica (L.) Merr. residue

There are many nutrients and active substances in the residue of traditional Chinese medicine, which can be processed into organic fertilizer and returned to the field to improve the soil fertility. In this study, we found that Brucea javanica (L.) Merr. residue has herbicidal activity and can be used for weed control in the field, this prompted us to investigate the active constituents in it. The herbicidal activities of extracts of B. javanica residue were evaluated by conducting bioassays against gramineous weed, Eleusine indica (L.) Gaertn. and broad-leaved weed, Bidens pilosa L., respectively. It confirmed that ethyl acetate and n-butanol extracts possessed potent biological activities on seed germination and seedling growth of E. indica at 5 mg/mL. This prompted us to investigate the active constituents in the seeds residue. By the activity-guided fractionation, eight known compounds were isolated, which were bruceines D?F (1–3), pityriacitrin (4), 4-(9H-β-carbolin-1-yl)-4-oxobut-2-enoic acid methyl ester (5), protocatechuic acid (6), vanillic acid (7) and carisphthalate (8). Then, three quassinoids (1–3) were evaluated for their potential herbicidal effects in bioassay. Results showed that bruceines D?F have potential herbicidal activity against the test weeds. In the range of experimental concentration, bruceine D had obvious herbicidal effect on the two tested weeds. At the concentration of 31.25 μg/mL, bruceine D could completely inhibit the root growth of E. indica; at the concentration of 125 μg/mL, bruceine D can inhibit the seed germination and shoot elongation of E. indica and the shoot growth of B. pilosa, with the inhibition reached 100%. In addition, at the same concentration (250 μg/mL), bruceines D?F could completely affected shoot elongation of B. pilosa. These results showed that B. javanica residue is a potential source of botanical herbicide development, which has great agricultural economic value, at the same time, the reuse of B. javanica residue realizes the transformation of waste into treasure, rational utilization of resources and sustainable development.     

Sessilifoliamides K and L: new alkaloids from Stemona sessilifolia

Two new alkaloids, sessilifoliamides K and L, having a pyrido[1,2-a]azonine skeleton were isolated from the roots of Stemona sessilifolia (Miq.) Miq. (Stemonaceae). Their structures were determined by interpretation of their spectroscopic data and computational methods.     

蒺藜果化学成分的分离和鉴定

分离鉴定了2个六糖呋甾皂苷, 其中化合物1为新化合物.     

鸦胆子化学成份的研究 II.鸦胆子苦素E-葡萄糖苷

A new quassinoid glucoside, yadanzigan (1a), has been isolated from Brucea javanica (L) Merr. 1a has formula C26H38O14(M+574), m.p. 243-245C, (α)D^2^3 60.0 (c. 1.70, H2O). The structure has been established as brucein E-2-β-D-glucopyranoside by enzymatic hydrolysis of 1a and elemental analyses, ^1H NMR, ^1^3C NMR and mass spectral analyses of 1a and its aglycone 2a.     

Optimized Green Extraction of Polyphenols from Cassia javanica L. Petals for Their Application in Sunflower Oil: Anticancer and Antioxidant Properties

The total phenolic content (TPC) from Cassia javanica L. petals were extracted using ethanolic solvent extraction at concentrations ranging from 0 to 90% and an SCF-CO₂ co-solvent at various pressures. Ultrasound-assisted extraction parameters were optimized using response surface methodology (RSM). Antioxidant and anticancer properties of total phenols were assessed. An SCF-CO₂ co-solvent extract was nano-encapsulated and applied to sunflower oil without the addition of an antioxidant. The results indicated that the best treatment for retaining TPC and total flavonoids content (TFC) was SCF-CO₂ co-solvent followed by the ultrasound and ethanolic extraction procedures. Additionally, the best antioxidant activity by β-carotene/linoleic acid and DPPH free radical-scavenging test systems was observed by SCF-CO₂ co-solvent then ultrasound and ethanolic extraction methods. SCF-CO₂ co-solvent recorded the highest inhibition % for PC3 (76.20%) and MCF7 (98.70%) and the lowest IC₅₀ value for PC3 (145 µ/mL) and MCF7 (96 µ/mL). It was discovered that fortifying sunflower oil with SCF-CO₂ co-solvent nanoparticles had a beneficial effect on free fatty acids and peroxide levels. The SCF-CO₂ method was finally found to be superior and could be used in large-scale processing.     

Comparative Analysis of the Phenolic Profile of Lycium barbarum L. Fruits from Different Regions in China

Lycium barbarum L. (LB) fruits have high nutritive values and therapeutic effects. The aim of this study was to comprehensively evaluate the differences in phenolic composition of LB fruits from different geographical regions. Different methods of characterization and statistical analysis of data showed that different geographic sources of China could be significantly separated from each other. The highest total phenolic compound (TPC) content was observed in LB fruits from Ningxia (LBN), followed by those from Gansu (LBG) and Qinghai (LBQ). The Fourier transform infrared (FTIR) spectra of LB fruits revealed that LBQ had a peak at 2972 cm⁻¹ whereas there was no similar peak in LBG and LBQ. A new HPLC method was established for the simultaneous determination of 8 phenolic compounds by quantitative analysis of multiple components by a single marker (QAMS), including 4 phenolic acids (chlorogenic acid, caffeic acid, 4-hydroxycinnamic acid, and ferulic acid), 1 coumarin (scopoletin), and 3 flavonoids (kaempferol-3-O-rutinoside, rutin, and narcissoside). It was showed that rutin was the most dominant phenolic compound in LBQ, although the average content of 4 phenolic acids was also high in LBQ, and scopoletin was the richest in LBG. UHPLC-Q-TOF-MS was used to qualitatively analyze the phenolics, which showed LBN was abundant in phenolic acids, LBQ was rich in flavonoids, and coumarins were the most plentiful in LBG. In conclusion, this study can provide references for the quality control and evaluation of phenolics in LB fruits and their by-products.     

Production of Bioactive Substances to Alleviates Hangover and Ethanol-Induced Liver Damage through Fermentation of Oenanthe javanica Using Lactiplantibacillus plantarum

The purpose of this study is to evaluate the effect of the bioconversion products of Oenanthe javanica extract fermented by Lactiplantibacillus plantarum (OEFL) on relieving hangovers and improving liver function. In addition, the bioactive substance of the OEFL, which alleviates hangover and ethanol-induced liver damage, was identified and its bioactive property was verified through in vivo experiments. In major substances analysis using high-performance liquid chromatography, OEFL produced 9.5-fold higher p-coumaric acid than the O. Javanica extract (OE). In addition, considering that quinic acid, which is not present in the OE, was produced in the OEFL it was confirmed that chlorogenic acid was decomposed into quinic acid by bioconversion. In the in vivo experiment using Sprague-Dawley rats, the OEFL and p-coumaric acid diets reduced blood ethanol, acetaldehyde, GPT, and ALP concentrations, increasing blood albumin concentrations compared to ethanol-administered groups, demonstrating that OEFL and p-coumaric acid, the main substance in the OEFL, improved ethanol-induced liver damage. Furthermore, the OEFL and its main bioactive substance, p-coumaric acid, alleviated liver fibrosis by downregulating TGF-β, SMAD-2, SMAD-4, α-SMA, and upregulating MMP-1. Therefore, OEFL is expected to be used as a functional food or pharmaceutical material as it has been confirmed to effectively relieve hangovers, prevent liver damage, and delay liver fibrosis in ethanol-induced liver damages.     

Separation and Determination of Chemical Constituents in the Roots of Rhus Javanica L. Var. Roxburghiana

From the roots of Rhus javanica L. var. roxburghiana, totally thirty‐seven known compounds have been isolated and identified. Their structures were elucidated based on their spectral analysis as well as comparison with authentic samples. These compounds were grouped to be fifteen triterpenoids, five steroids, two lignans, two flavonoids, nine phenolics, and four other aromatic derivatives. Their cytotoxicities toward two cell lines NUGC‐3 and HONE‐1 were also evaluated.     

超高分辨质谱技术用于鸦胆子油及其口服制剂特征谱的高通量快速分析

采用直接进样－电喷雾电离超高分辨质谱技术（DI－ESI－UHRMS）结合统计学数据分析策略,建立了鸦胆子油及其口服制剂的特征图谱高通量快速分析方法。基于DI－ESI－UHRMS高分辨率、高通量和非靶向的特点,对鸦胆子油和大豆磷脂软胶囊正离子模式下的数据进行分析,利用分子离子峰精确质量数和精细同位素峰信息,解析出69种准确分子式（与理论值的误差均小于1 ppm）。结合二级质谱、文献和Lipid Maps网站中数据,对69种分子式进行半鉴定。结果显示,其主要为糖类、磷脂类、油酸类和油脂类成分。主成分分析、正交偏最小二乘判别分析和层次聚类分析结果显示,鸦胆子油、橄榄油和菜籽油中不存在磷脂类成分,文中半鉴定的69种分子式对应的母峰（m/z）可作为鸦胆子油掺伪鉴别和不同鸦胆子油口服制剂差异分析的指标成分。该研究为进一步完善鸦胆子及其制剂的质量标准提供了理论支撑。     

Anti-Aging Effect of Momordica charantia L. on d-Galactose-Induced Subacute Aging in Mice by Activating PI3K/AKT Signaling Pathway

Anti-aging is a challenging and necessary research topic. Momordica charantia L. is a common edible medicinal plant that has various pharmacological activities and is often employed in daily health care. However, its anti-aging effect on mice and the underlying mechanism thereof remain unclear. Our current study mainly focused on the effect of Momordica charantia L. on d-galactose-induced subacute aging in mice and explored the underlying mechanism. UHPLC-Q-Exactive Orbitrap MS was applied to qualitatively analyze the chemical components of Momordica charantia L. ethanol extract (MCE). A subacute aging mice model induced by d-galactose (d-gal) was established to investigate the anti-aging effect and potential mechanism of MCE. The learning and memory ability of aging mice was evaluated using behavioral tests. The biochemical parameters, including antioxidant enzyme activity and the accumulation of lipid peroxides in serum, were measured to explore the effect of MCE on the redox imbalance caused by aging. Pathological changes in the hippocampus were observed using hematoxylin and eosin (H&E) staining, and the levels of aging-related proteins in the PI3K/AKT signaling pathway were assessed using Western blotting. The experimental results demonstrated that a total of 14 triterpenoids were simultaneously identified in MCE. The behavioral assessments results showed that MCE can improve the learning and memory ability of subacute mice. The biochemical parameters determination results showed that MCE can improve the activity of antioxidant enzymes and decrease the accumulation of lipid peroxides in aging mice significantly. Furthermore, aging and injury in the hippocampus were ameliorated. Mechanistically, the results showed a significant upregulation in the protein expression of P-PI3K/PI3K and P-AKT/AKT (p < 0.01), as well as a significant reduction in cleaved caspase-3/caspase-3, Bax and P-mTOR/mTOR (p < 0.01). Our results confirm that MCE could restore the antioxidant status and improve cognitive impairment in aging mice, inhibit d-gal-induced apoptosis by regulating the PI3K/AKT signaling pathway, and rescue the impaired autophagy caused by mTOR overexpression, thereby exerting an anti-aging effect.     

Two New Flavonoids from the Rhizomes of Abacopteris penangiana

A new flavan‐4‐ol glycoside, abacopterin K ( 1 ), and a new dihydrochalcone glycoside, abacopterin L ( 2 ), were isolated from the rhizomes of Abacopteris penangiana. Their structures were elucidated on the basis of various spectroscopic analyses and chemical evidences. The novel glucosylation pattern of abacopterin K consisting of two ‘glucose‐fused’ dioxepine ring moieties is found for the first time within natural flavonoids.