CN112353844A - Rabdosia rubescens leaf aqueous extract powder, preparation thereof, radical scavenging action and use thereof - Google Patents
Rabdosia rubescens leaf aqueous extract powder, preparation thereof, radical scavenging action and use thereof Download PDFInfo
- Publication number
- CN112353844A CN112353844A CN202011233389.6A CN202011233389A CN112353844A CN 112353844 A CN112353844 A CN 112353844A CN 202011233389 A CN202011233389 A CN 202011233389A CN 112353844 A CN112353844 A CN 112353844A
- Authority
- CN
- China
- Prior art keywords
- carboxy
- quinic acid
- cinnamoyl
- hydroxy
- formyloxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation, decoction
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Alternative & Traditional Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Epidemiology (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention discloses rabdosia rubescens leaf aqueous extract powder, a preparation method thereof and application thereof in removing free radicals. The rabdosia rubescens leaf water extract powder prepared by the method contains 25 quinic acid compounds and 11 quercetin compounds. Experiments prove that the rabdosia rubescens leaf water extract powder has excellent free radical scavenging effect. Therefore, the invention provides an effective technical means for resisting oxidative stress.
Description
Technical Field
The invention relates to a method for preparing rabdosia rubescens leaf water extract powder, and relates to application of the rabdosia rubescens leaf water extract powder prepared by the method in preparation of a free radical removing medicine. The invention belongs to the field of biological medicine.
Background
Oxidative stress is a stress phenomenon that the balance of oxidation and antioxidation of the body inclines towards the oxidation direction, so that inflammatory infiltration of neutrophils is caused, secretion of protease is increased, and a large number of oxidation intermediate products are generated. In oxidative stress, free radicals accumulate in the body and have negative health effects. Freedom in vivoBasal accumulation is generally considered to be one of the important factors that lead to the deterioration of cell function, aging, and even death. Free radicals include reactive oxygen species free Radicals (ROS) and reactive nitrogen species free Radicals (RNS). The active oxygen radical being a superoxide anion (. O)2 -) Hydroxyl radical (. OH) and hydrogen peroxide (H)2O2) Is a general term for (1). The active nitrogen radical is nitrogen monoxide radical (NO.), nitrogen dioxide radical (NO.)2) And peroxynitrite radical (. ONO)2 -) Is a general term for (1). Free radical accumulation in the body refers to the accumulation of ROS and RNS. Free radicals are exceptionally reactive molecules that can react with all cellular components. Under normal conditions, organs in physiological response produce free radicals. Too high a concentration of free radicals causes a loss of balance in cell function and morphology. Primary radicals generated in the cell further expand into secondary radicals when the equilibrium moves in the direction of oxidation. Cellular proteins are ideal targets for secondary free radical attack. Secondary free radicals target cellular proteins and trigger biological damage to cells.
Numerous studies have demonstrated that free radicals are an important pathological indication in the pathogenesis of many human diseases. Free radicals randomly oxidize proteins or polypeptides to side chain carbonyl derivatives to inactivate them. The degree of protein carbonylation was used to quantify the degree of functional senescence in human dermal fibroblasts, lens and brain tissue. While there is no direct evidence to associate free radicals with the etiology of degenerative diseases of the central nervous system (e.g., motor neuron disease, cerebellar ataxia and parkinson's disease), indirect evidence leads to the hypothesis that free radicals contribute to the pathogenesis of these diseases.
Oxidative stress is involved in the pathological process of acute and chronic liver diseases by inducing hepatocyte dysfunction. Although free radicals are derived from the metabolism of normal cells, the metabolism of cells in liver diseases overproduces free radicals. The overproduced free radicals cross the antioxidant defenses and cause liver damage. Among liver diseases, the incidence of nonalcoholic fatty liver diseases characterized by developing oxidative stress and breaking redox balance is the highest. The pathology of nonalcoholic fatty liver disease belongs to a multifactorial pathology, including alterations in lipid metabolism, mitochondrial dysfunction, inflammation and oxidative stress.
Cardiovascular diseases including ischemic heart disease and cerebrovascular disease are the top among the morbidity and mortality of diseases on a global scale. Atherosclerosis is the major preferential causative agent of most cardiovascular diseases. It is well understood that oxidative stress and inflammation are the two main mechanisms responsible for atherosclerosis. Under oxidative stress conditions, higher unsaturated fatty acid-containing phospholipids and cholesterol esters in cell membranes and ester proteins are readily oxidized to complex mixed oxidation products in a free radical-induced peroxidation process of esters. Most evidence suggests that these oxidized lipids are active in the inflammatory response of atherosclerosis by interacting with immune cells (e.g., macrophages) and endothelial cells.
Sometimes tumor onset is broken down into three steps, initiation, acceleration and spread. In the priming step, the carcinogens modulate the genetic identity of the cells and allow the cells to divide rapidly. At the acceleration step, the genetically damaged cells fail to lock into the genetic lesion and contribute to unregulated cell growth. In the epidemic step, the cell system growing without control establishes a blood supply network through angiogenesis and causes tumor and carcinogenesis to grow. There is evidence that oxidative stress, chronic inflammation and tumors are closely associated. Free radical induced oxidative stress is prevalent in many types of tumor cells associated with altered redox signaling pathways. Unlike normal cells, oxidative stress induces a loss of balance in the redox of various tumor cells. In this sense, redox imbalance may be associated with an oncogenic stimulus. DNA mutation is a critical step in the carcinogenic process, while an increased level of oxidative DNA damage is observed in a variety of tumors. It can be seen that such lesions are strongly implicated in the etiology of tumors. Increased production of reactive oxygen radicals and altered redox status in tumor cells has been observed early, while tumor cells of advanced tumors often show multiple genetic variations and strong oxidative stress.
Primary radicals generated in cells and tissues under oxidative stress further expand to become secondary radicals. Proteins in cells and tissues are ideal reactants for secondary free radicals. Secondary free radicals target these proteins and initiate biological damage to cells and tissues. Oxidative stress-induced biological damage to cells and tissues has led to neonatal morbidity, particularly in premature infants for which antioxidant defense systems have not yet been established. Mitochondria are not only the subject of oxidative damage, but also tend to be involved in oxidative self-damage in the onset of neonatal lung disease. Similarly, both intrauterine growth restriction and giant fetuses are associated with mitochondrial dysfunction due to oxidative stress. In addition, the ability of the lamb to produce pro-inflammatory cytokines is significantly enhanced by the pure oxygen-dominated reoxygenation on hypoxic ischemic newborn lamb models.
In summary, oxidative stress, which is characterized by the accumulation of free radicals, is the cause of a number of major common diseases. The invention is safe and effective free radical scavenging medicine and can provide effective technical means for scavenging free radicals.
Rabdosia Rubescens (Hemsl.) Hara is whole plant of Rabdosia Rubescens (Hemsl.) Hara of Rabdosia of Labiatae. Rabdosia rubescens is a perennial herb, widely distributed in the Yangtze river basin of the yellow river of China, and mainly produced in the areas of the south Henan Jiyuan Taihang mountain and the Wang House mountain. Because of the functions of clearing away heat and toxic material, clearing and nourishing throat, and relieving swelling and pain, the rabdosia rubescens whole herb is boiled in water for drinking all the time in folk. In the past 30 years, the research on the chemical components and pharmacological action of rabdosia rubescens mainly focuses on the fat-soluble parts of leaves and stems, and the representative components are rubescensin A and rubescensin B. To date, there has been no study concerning the chemical composition and therapeutic effect of aqueous extracts of Rabdosia Rubescens (Hemsl.) Hara leaves.
The inventor has long conducted research on chemical components and therapeutic effects of the rabdosia rubescens leaf aqueous extract powder. The inventor carries out mass spectrometry on chemical components of rabdosia rubescens leaf water extract powder, and discovers 36 unreported components which mainly comprise cinnamoyl quinic acid and multi-substituted quercetin. Although the biological activity of the individual components of the aqueous extract powder of Rabdosia rubescens has been reported, the biological activity of the combination of all components is unknown. Through repeated studies, the inventors found that 28 of these components scavenged free radicals. Compared with the known invention of rabdosia rubescens, the invention of the rabdosia rubescens leaf water extract powder capable of removing free radicals achieves a brand new height. Based on these findings, the inventors have proposed the present invention.
Disclosure of Invention
The invention aims to provide a method for preparing rabdosia rubescens leaf water extract powder and the rabdosia rubescens leaf water extract powder prepared by the method. Experiments prove that the rabdosia rubescens leaf water extract powder prepared by the invention has the function of removing free radicals. In order to achieve the purpose, the invention adopts the following five technical means.
The first technical means is to provide rabdosia rubescens leaf water extract powder, the rabdosia rubescens leaf water extract powder contains 25 kinds of quinic acid compounds and 11 kinds of quercetin compounds, the 25 kinds of quinic acid compounds are 3-O- [ E-2- (3-carboxyl-1-propylene carbonyl oxygen) -3, 5-diformyl oxygen-4- (3-carboxyl-2-propylene carbonyl oxygen) -6- (6-carboxyl-1, 3-hexadiene carbonyl oxygen) cinnamoyl ] quinic acid, 3-O- [ E-2- (6-hydroxyl-1-hexene carbonyl oxygen) -3- (4-hydroxyl-1-butylene carbonyl oxygen) -4- (3-carboxyl-1-propylene carbonyl oxygen) -5-methoxy-6- (3-O- [ E-2- (6-hydroxyl-1-hexene carbonyl oxygen) -3- (4-hydroxyl-1-butylene carbonyl oxygen) 5-carboxy-1-pentenylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (3-carboxypropylcarbonyloxy) -3, 5-dimethoxy-4- (3-carboxypropylcarbonyloxy) -6- (6-carboxyhexylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (6-hydroxyhexylcarbonyloxy) -3, 5-dicarboxyloxy-4- (3-hydroxypropioncarbonyloxy) -6- (6-carboxyhexylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (7-carboxy-1, 3-heptadiencarbonyloxy) -3, 4-bis (3-carboxy-1-propenylcarbonyloxy) -5-formyloxy-6- (6-carboxy- 1, 3-hexadienecarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (7-carboxy-1-heptenecarbonyloxy) -3- (6-hydroxy-1-hexenecarbonyloxy) -4- (3-carboxy-1-propenylcarbonyloxy) -5-formyloxy-6- (6-carboxy-1-hexenecarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (4-hydroxybutanecarbonyloxy) -3, 4-bis (3-carboxypropylenecarbonyloxy) -5-formyloxy-6- (6-carboxy-1-hexenecarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (5-carboxy-1-pentenylcarbonyloxy) -3- Carboxyacetoxy-4, 6-bis (3-carboxypropenoxy) -5-carboxyoxocinnamoyl ] quinic acid, 3-O- [ E-2, 3-bis (3-carboxy-1-propenylcarbonyloxy) -4- (3-carboxyacryloyloxy) -5-carboxyacetoxy-6- (4-carboxy-1-butenylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2,3, 4-tris (4-hydroxybutenylcarbonyloxy) -5-formyloxy-6- (6-carboxy-1, 3-hexadienylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (4-hydroxy-1, 3-butadienecarbonyloxy) -3, 4-bis (3-carboxy-1-propenecarbonyloxy) -5-formyloxy-6- (6-carboxy-1, 3, 5-hexatrienylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (4-hydroxy-1, 3-butadienecarbonyloxy) -3-carboxyacetoxy-4- (3-carboxy-1-propenecarbonyloxy) -5-formyloxy-6- (4-carboxy-1, 3-butadienecarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 3-bis (3-carboxypropanecarbonyloxy) -4- (3-carboxypropanoyloxy) -5-formyloxy-6- (6-carboxy-1-propenoyloxy) -hexenecarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 3-bis (3-carboxypropylcarbonyloxy) -4- (3-hydroxypropionyloxy) -5-hydroxymethyl-6- (5-carboxypentylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 6-bis (5-carboxy-1-pentenylcarbonyloxy) -3- (3-carboxypropylcarbonyloxy) -4-carboxyacetoxy-5-methoxycinnamoyl ] quinic acid, 3-O- [ E-2- (8-carboxy-1-octenecarbonyloxy) -3- (3-carboxypropylcarbonyloxy) -4- (7-carboxy-1-heptenecarbonyloxy) -5-carboxyacetoxy-6- (4- Carboxy-1-butenylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (9-hydroxy-1-nonenecarbonyloxy) -3- (4-hydroxybutanecarbonyloxy) -4- (8-hydroxy-1-octenecarbonyloxy) -5-methoxy-6- (4-carboxy-1-butenylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (7-carboxy-1, 3, 5-heptatrienylcarbonyloxy) -3, 4-bis (5-carboxy-1, 3-pentadienylcarbonyloxy) -5-carboxyacetoxy-6- (6-carboxy-1, 3-hexadienylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (4-hydroxy-1-butenylcarbonyloxy) -3- (4-carboxy-1-butenylcarbonyloxy) -4- (3-carboxypropenyloxy) -5-carboxyacetyloxy-6- (4-carboxy-1, 3-butadienylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (7-carboxy-1, 3, 5-heptatrienylcarbonyloxy) -3- (8-hydroxy-1, 3,5, 7-octatetraenylcarbonyloxy) -4, 5-bis (4-carboxy-1, 3-butadienoyloxy) -6- (6-carboxy-1, 3, 5-hexatrienylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (4-hydroxybutylcarbonyloxy) -3, 4-bis (3-carboxypropylcarbonyloxy) -5- (3-hydroxypropionyloxy) -6- (4-carboxybutylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 6-bis (5-carboxy-1-pentenoyloxy) -3- (3-carboxypropylcarbonyloxy) -4- (3-carboxypropyloyloxy) -5-hydroxycinnamoyl ] quinic acid, 3-O- [ E-2, 5-bis (7-carboxy-1, 3-heptadienoyloxy) -3- (6-hydroxy-1, 3-hexadienecarbonyloxy) -4- (4-carboxy-1, 3-butadienecarbonyloxy) -6- (6-carboxy-1, 3-hexadienecarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (5-hydroxy-1-pentenecarbonyloxy) -3, 4-bis (4-carboxy-1-butenecarbonyloxy) -5-carboxyacetoxy-6- (4-carboxy-1, 3-butadienecarbonyloxy) cinnamoyl ] quinic acid and 3-O- [ E-2, 5-dicarboxyacetyloxy-3- (10-carboxy-1, 3,5, 7-decatetraenecarbonyloxy) -4- (8-carboxy-1, 3, 5-octatrienylcarbonyloxy) -6- (6-carboxy-1, 3-hexadienylcarbonyloxy) cinnamoyl ] quinic acid; the 11 kinds of quercetin compounds are 3-O-glucoside-2 '-formyloxy-3' - (3-carboxyl acryloyloxy) -4 '-carboxyl acetyloxy-5' - (3-carboxyl-1-propylene carbonyloxy) -6 '- (5-hydroxyl-1-pentene carbonyloxy) quercetin, 3-O-glucoside-2' -formyloxy-3 '- (10-carboxyl-1, 3-decadiene carbonyloxy) -4' - (5-carboxyl-2-pentene carbonyloxy) -5 '- (3-carboxyl-1-propylene carbonyloxy) -6' - (5-hydroxyl-1-pentene carbonyloxy) quercetin, 3-O-glucoside-2 '-formyloxy-3' - (6-carboxy-1-hexenecarbonyloxy) -4 '- (6-hydroxy-2-hexenecarbonyloxy) -5' - (3-carboxy-1-propenecarbonyloxy) -6 '- (5-hydroxy-1-pentenecarbonyloxy) quercetin, 3-O-glucoside-2' -formyloxy-3 '- (7-hydroxy-1, 3, 5-heptatrienylcarbonyloxy) -4' - (4-carboxy-2-butenecarbonyloxy) -5 '- (3-carboxy-1-propenecarbonyloxy) -6' - (7-carboxy-1, 3-heptadienylcarbonyloxy) quercetin, 3-O-glucoside-2 '-formyloxy-3' - (8-carboxy-1, 3, 5-octatrienylcarbonyloxy) -4 '- (5-carboxy-1-pentenylcarbonyloxy) -5' - (5-carboxy-1, 3-pentadienylcarbonyloxy) -6 '- (6-hydroxy-1, 3, 5-hexatrienylcarbonyloxy) quercetin, 3-O-glucoside-2' -formyloxy-3 '- (4-carboxybutylcarbonyloxy) -4' - (3-carboxypropylcarbonyloxy) -5 '- (4-hydroxybutylcarbonyloxy) -6' - (5-hydroxy-1-pentenylcarbonyloxy) quercetin, 3-O-glucoside-2 ' -formyloxy-3 ', 6 ' -bis (7-hydroxy-1-heptenecarbonyloxy) -4 ' - (4-carboxy-1-butenylcarbonyloxy) -5 ' - (3-carboxy-1-propenylcarbonyloxy) quercetin, 3-O-glucoside-2 ' -formyloxy-3 ' - (7-carboxy-1, 3, 5-heptatrienylcarbonyloxy) -4 ', 5 ', 6 ' -tris (5-carboxy-1, 3-butadienylcarbonyloxy) quercetin, 3-O-glucoside-2 ' -formyloxy-3 ' - (7-carboxy-1, 3, 5-heptatrienylcarbonyloxy) -4 ', 5 '-bis (5-carboxy-1, 3-pentadienoyloxy) -6' - (7-carboxy-1, 3-heptadienoyloxy) quercetin, 3-O-glucoside-2 '-formyloxy-3' - (4-carboxybutylcarbonyloxy) -4 '- (3-carboxypropylcarbonyloxy) -5' - (4-hydroxybutylcarbonyloxy) -6 '- (5-hydroxypentanoyloxy) quercetin and 3-O-glucoside-2' -methoxy-3 '- (7-hydroxy-1-heptenecarbonyloxy) -4', 5 '-bis (5-hydroxy-1-pentenoyloxy) -6' - (8-hydroxy-1, 3-octadienecarbonyloxy) quercetin.
The second technical means is to provide a method for preparing the rabdosia rubescens leaf water extract powder. Cleaning Rabdosia Rubescens (Hemsl.) Hara leaf with tap water, heating in distilled water at 50-100 deg.C for 0.5-4 hr, stirring at 200-400rpm, cooling to room temperature, filtering, washing filter cake with distilled water for 3 times, and concentrating the combined filtrate under reduced pressure to obtain powder of Rabdosia Rubescens (Hemsl.) Hara leaf water extract.
The third technical means is to provide a mass spectrum total ion current spectrum of the rabdosia rubescens leaf water extract powder.
The fourth technical means is to provide the chemical structures of 36 components corresponding to the peaks in the mass spectrum total ion flow spectrum of the rabdosia rubescens leaf aqueous extract powder.
The fifth technical means is to evaluate the free radical scavenging activity of the rabdosia rubescens leaf aqueous extract powder.
Drawings
FIG. 1 UPLC-Mass Spectroscopy Total ion flux spectra of Rabdosia Rubescens leaf aqueous extract powder.
FIG. 2 shows 3-O- [ E-2- (3-carboxy-1-acryloyloxy) -3, 5-diformyloxy-4- (3-carboxy-2-acryloyloxy) -6- (6-carboxy-1, 3-hexadienoyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 3 shows 3-O- [ E-2- (6-hydroxy-1-hexenecarbonyloxy) -3- (4-hydroxy-1-butenecarbonyloxy) -4- (3-carboxy-1-propenecarbonyloxy) -5-methoxy-6- (5-carboxy-1-pentenecarbonyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 4 shows 3-O- [ E-2- (3-carboxypropylcarbonyloxy) -3, 5-dimethoxy-4- (3-carboxypropylcarbonyloxy) -6- (6-carboxyhexylcarbonyloxy) cinnamoyl ] quinic acid in rabdosia rubescens leaf aqueous extract powder and cleavage products.
FIG. 5 shows 3-O- [ E-2- (6-hydroxycaproyloxy) -3, 5-dicarboxyloxy-4- (3-hydroxypropionyloxy) -6- (6-carboxyhexylcarbonyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia Rubescens leaf aqueous extract powder.
FIG. 6 shows 3-O- [ E-2- (7-carboxy-1, 3-heptadienoyloxy) -3, 4-bis (3-carboxy-1-propenoyloxy) -5-formyloxy-6- (6-carboxy-1, 3-hexadienoyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 7 shows 3-O- [ E-2- (7-carboxy-1-heptenecarbonyloxy) -3- (6-hydroxy-1-hexenecarbonyloxy) -4- (3-carboxy-1-propenecarbonyloxy) -5-formyloxy-6- (6-carboxy-1-hexenecarbonyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 8 shows 3-O- [ E-2- (4-hydroxybutylcarbonyloxy) -3, 4-bis (3-carboxypropylcarbonyloxy) -5-formyloxy-6- (6-carboxy-1-hexenecarbonyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 9 shows 3-O- [ E-2- (5-carboxy-1-pentenoyloxy) -3-carboxyacetoxy-4, 6-bis (3-carboxyacryloyloxy) -5-formyloxy cinnamoyl ] quinic acid and cleavage products in Rabdosia Rubescens leaf aqueous extract powder.
FIG. 10 shows 3-O- [ E-2, 3-bis (3-carboxy-1-propenylcarbonyloxy) -4- (3-carboxy-propenoyloxy) -5-carboxy acetyloxy-6- (4-carboxy-1-butenylcarbonyloxy) cinnamoyl ] quinic acid and cleavage products from Rabdosia rubescens leaf aqueous extract powder.
FIG. 11 shows 3-O- [ E-2,3, 4-tris (4-hydroxybutylcarbonyloxy) -5-formyloxy-6- (6-carboxy-1, 3-hexadienoyloxy) cinnamoyl ] quinic acid in Rabdosia rubescens leaf aqueous extract powder and cleavage products.
FIG. 12 shows 3-O- [ E-2- (4-hydroxy-1, 3-butadienecarbonyloxy) -3, 4-bis (3-carboxy-1-propenecarbonyloxy) -5-formyloxy-6- (6-carboxy-1, 3, 5-hexatrienylcarbonyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 13 shows 3-O- [ E-2- (4-hydroxy-1, 3-butadienecarbonyloxy) -3-carboxyacetoxy-4- (3-carboxy-1-propenecarbonyloxy) -5-formyloxy-6- (4-carboxy-1, 3-butadienecarbonyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 14 shows 3-O- [ E-2, 3-bis (3-carboxypropylcarbonyloxy) -4- (3-carboxypropylcarbonyloxy) -5-formyloxy-6- (6-carboxy-1-hexencarbonyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 15 shows 3-O- [ E-2, 3-bis (3-carboxypropylcarbonyloxy) -4- (3-hydroxypropionyloxy) -5-hydroxymethyl-6- (5-carboxypentylcarbonyloxy) cinnamoyl ] quinic acid in Rabdosia rubescens leaf aqueous extract powder and its cleavage product.
FIG. 16 shows 3-O- [ E-2, 6-bis (5-carboxy-1-pentenoyloxy) -3- (3-carboxypropyleneoyloxy) -4-carboxyacetoxy-5-methoxycinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 17 shows 3-O- [ E-2- (8-carboxy-1-octenecarbonyloxy) -3- (3-carboxypropylenecarbonyloxy) -4- (7-carboxy-1-heptenecarbonyloxy) -5-carboxyacetoxy-6- (4-carboxy-1-butencarbonyloxy) cinnamoyl ] quinic acid and cleavage products in an aqueous extract powder of Rabdosia Rubescens (Hemsl.) Hara leaves.
FIG. 18 shows 3-O- [ E-2- (9-hydroxy-1-nonenecarbonyloxy) -3- (4-hydroxybutanecarbonyloxy) -4- (8-hydroxy-1-octenecarbonyloxy) -5-methoxy-6- (4-carboxy-1-butenylcarbonyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 19 shows 3-O- [ E-2- (7-carboxy-1, 3, 5-heptatrienylcarbonyloxy) -3, 4-bis (5-carboxy-1, 3-pentadienoyloxy) -5-carboxyacetoxy-6- (6-carboxy-1, 3-hexadienoyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 20 shows 3-O- [ E-2- (4-hydroxy-1-butenylcarbonyloxy) -3- (4-carboxy-1-butenylcarbonyloxy) -4- (3-carboxy acryloyloxy) -5-carboxyacetoxy-6- (4-carboxy-1, 3-butadienylcarbonyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 21 3-O- [ E-2- (7-carboxy-1, 3, 5-heptatrienylcarbonyloxy) -3- (8-hydroxy-1, 3,5, 7-octatetraenylcarbonyloxy) -4, 5-bis (4-carboxy-1, 3-butadienoyloxy) -6- (6-carboxy-1, 3, 5-hexatrienylcarbonyloxy) cinnamoyl ] quinic acid in Rabdosia rubescens leaf aqueous extract powder and cleavage products.
FIG. 22 shows 3-O- [ E-2- (4-hydroxybutylcarbonyloxy) -3, 4-bis (3-carboxypropylcarbonyloxy) -5- (3-hydroxypropionyloxy) -6- (4-carboxybutylcarbonyloxy) cinnamoyl ] quinic acid in Rabdosia rubescens leaf aqueous extract powder and cleavage products.
FIG. 23 shows 3-O- [ E-2, 6-bis (5-carboxy-1-pentenoyloxy) -3- (3-carboxypropanoyloxy) -4- (3-carboxypropanoyloxy) -5-hydroxycinnamoyl ] quinic acid and cleavage products from Rabdosia rubescens leaf aqueous extract powder.
FIG. 24 3-O- [ E-2, 5-bis (7-carboxy-1, 3-heptadienoyloxy) -3- (6-hydroxy-1, 3-hexadienoyloxy) -4- (4-carboxy-1, 3-butadienoyloxy) -6- (6-carboxy-1, 3-hexadienoyloxy) cinnamoyl ] quinic acid and cleavage products from Rabdosia rubescens leaf aqueous extract powder.
FIG. 25 shows 3-O- [ E-2- (5-hydroxy-1-pentenylcarbonyloxy) -3, 4-bis (4-carboxy-1-butenylcarbonyloxy) -5-carboxyacetoxy-6- (4-carboxy-1, 3-butadienylcarbonyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 26 shows 3-O- [ E-2, 5-dicarboxyacetyloxy-3- (10-carboxy-1, 3,5, 7-decatetraenylcarbonyloxy) -4- (8-carboxy-1, 3, 5-octatrienylcarbonyloxy) -6- (6-carboxy-1, 3-hexadienylcarbonyloxy) cinnamoyl ] quinic acid and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 27 shows 3-O-glucoside-2 ' -formyloxy-3 ' - (3-carboxyacryloyloxy) -4 ' -carboxyacetoxy-5 ' - (3-carboxy-1-propenylcarbonyloxy) -6 ' - (5-hydroxy-1-pentenylcarbonyloxy) quercetin and cleavage products in Rabdosia Rubescens leaf aqueous extract powder.
FIG. 28 shows 3-O-glucoside-2 ' -formyloxy-3 ' - (10-carboxy-1, 3-decadienylcarbonyloxy) -4 ' - (5-carboxy-2-pentenylcarbonyloxy) -5 ' - (3-carboxy-1-propenylcarbonyloxy) -6 ' - (5-hydroxy-1-pentenylcarbonyloxy) quercetin and cleavage products in an aqueous extract powder of Rabdosia rubescens leaves.
FIG. 29 shows 3-O-glucoside-2 ' -formyloxy-3 ' - (6-carboxy-1-hexenecarbonyloxy) -4 ' - (6-hydroxy-2-hexenecarbonyloxy) -5 ' - (3-carboxy-1-propenecarbonyloxy) -6 ' - (5-hydroxy-1-pentenecarbonyloxy) quercetin and cleavage products in an aqueous extract powder of Rabdosia Rubescens leaf.
FIG. 30 shows 3-O-glucoside-2 ' -formyloxy-3 ' - (7-hydroxy-1, 3, 5-heptatrienylcarbonyloxy) -4 ' - (4-carboxy-2-butenylcarbonyloxy) -5 ' - (3-carboxy-1-propenylcarbonyloxy) -6 ' - (7-carboxy-1, 3-heptadienylcarbonyloxy) quercetin and cleavage products in an aqueous extract powder of Rabdosia Rubescens (Hemsl.) Hara leaves.
FIG. 31 shows 3-O-glucoside-2 ' -formyloxy-3 ' - (8-carboxy-1, 3, 5-octatrienylcarbonyloxy) -4 ' - (5-carboxy-1-pentenylcarbonyloxy) -5 ' - (5-carboxy-1, 3-pentadienylcarbonyloxy) -6 ' - (6-hydroxy-1, 3, 5-hexatrienylcarbonyloxy) quercetin and its cleavage products in rabdosia rubescens leaf aqueous extract powder.
FIG. 32 shows 3-O-glucoside-2 ' -formyloxy-3 ' - (4-carboxybutylcarbonyloxy) -4 ' - (3-carboxypropylcarbonyloxy) -5 ' - (4-hydroxybutylcarbonyloxy) -6 ' - (5-hydroxy-1-pentenylcarbonyloxy) quercetin and cleavage products in an aqueous extract powder of Rabdosia Rubescens leaf.
FIG. 33 shows 3-O-glucoside-2 ' -formyloxy-3 ', 6 ' -bis (7-hydroxy-1-heptenecarbonyloxy) -4 ' - (4-carboxy-1-butenylcarbonyloxy) -5 ' - (3-carboxy-1-propenylcarbonyloxy) quercetin and cleavage products in an aqueous extract powder of Rabdosia rubescens leaves.
FIG. 34 3-O-glucoside-2 ' -formyloxy-3 ' - (7-carboxy-1, 3, 5-heptatrienylcarbonyloxy) -4 ', 5 ', 6 ' -tris (5-carboxy-1, 3-butadienylcarbonyloxy) quercetin and cleavage products in an aqueous extract powder of Rabdosia Rubescens leaf.
FIG. 35 3-O-glucoside-2 ' -formyloxy-3 ' - (7-carboxy-1, 3, 5-heptatrienylcarbonyloxy) -4 ', 5 ' -bis (5-carboxy-1, 3-pentadienylcarbonyloxy) -6 ' - (7-carboxy-1, 3-heptadienylcarbonyloxy) quercetin and cleavage products in Rabdosia rubescens leaf aqueous extract powder.
FIG. 36 shows 3-O-glucoside-2 ' -formyloxy-3 ' - (4-carboxybutylcarbonyloxy) -4 ' - (3-carboxypropylcarbonyloxy) -5 ' - (4-hydroxybutylcarbonyloxy) -6 ' - (5-hydroxypentylcarbonyloxy) quercetin and cleavage products in an aqueous extract powder of Rabdosia Rubescens leaf.
FIG. 37 shows 3-O-glucoside-2 ' -methoxy-3 ' - (7-hydroxy-1-heptenecarbonyloxy) -4 ', 5 ' -bis (5-hydroxy-1-pentenecarbonyloxy) -6 ' - (8-hydroxy-1, 3-octadienecarbonyloxy) quercetin and cleavage products in an aqueous extract powder of Rabdosia rubescens leaves.
FIG. 38 concentration dependent inhibition of nitrogen radical peak intensity for an aqueous extract of Rabdosia Rubescens (Hemsl.) Hara leaves.
Detailed Description
To further illustrate the invention, a series of examples are given below. These examples are purely illustrative and are intended to be a detailed description of the invention only and should not be taken as limiting the invention.
Example 1 preparation of Rabdosia Rubescens leaf aqueous extract powder
Washing dry Rabdosia Rubescens (Hemsl.) Hara leaves with tap water, heating 300g of the washed leaves in 1200mL of 700-1200mL distilled water at 50-100 deg.C for 0.5-4 h while stirring (200-400 rpm). Cooling to room temperature, filtering, and concentrating the filtrate under reduced pressure to obtain 90g Rabdosia Rubescens leaf water extract powder. Or washing fresh Rabdosia Rubescens (Hemsl.) Hara leaves with tap water, heating 1350g of the washed leaves in 2500mL of 1500-. Cooling to room temperature, filtering, and concentrating the filtrate under reduced pressure to obtain 90g Rabdosia Rubescens leaf water extract powder.
Example 2 determination of chromatography and Mass Spectrometry ion mobility Spectroscopy of Rabdosia Rubescens leaf aqueous extract powder
2-1 preparation of sample solution (10mg/mL)
26.7mg of Rabdosia Rubescens leaf aqueous extract powder was weighed and dissolved in 2.67mL of ultrapure water. The resulting solution was sonicated for 1 minute, followed by centrifugation at 13000r/min for 10 minutes. The supernatant was taken, filtered through a 0.22 μm filter and placed in a sample vial for chromatographic and mass spectrometric determination.
2-2 chromatographic conditions
Chromatographic column Waters, Acquity
A HSS T3 column (2.1 × 100mm i.d.,1.7 μm); the sample injection volume is 2 mu L; 190-400nm of PDA detector; mobile phase water (0.1% formic acid), acetonitrile; the mobile phase was used and the column was washed with the gradient of table 1.
TABLE 1 mobile phase gradiometer
2-3 measuring chromatogram
UPLC chromatogram of Rabdosia Rubescens leaf aqueous extract powder was determined and recorded according to the above chromatographic assay conditions (see FIG. 1 of the specification).
2-4. conditions for measuring ion flow spectrum and mass spectrum
Electrospray ionization modes are Positive (PI) and Negative (NI) modes. The ion mode parameters comprise that the capillary tube voltage is 1000V, the desolvation air flow rate is 800L/h, the temperature is 450 ℃, the source temperature is 120 ℃, the taper hole air flow rate is 50L/h, the spraying air pressure is 6bar, the fragmentation voltage is 20-45V, the sampling cone voltage is 6V, the acquisition mode is an MSE continuum resolution mode, the data acquisition range of the ratio (m/z) of the mass number of the charged particles to the charge number is 100-1500, the Trap fragmentation voltage of the low-energy channel is 6V, the gradient voltage of the Trap fragmentation voltage of the high-energy channel is 20-60V, LE (leucine enkephalin) is selected as a mass lock to acquire m/z, and the range is 100-1500.
2-5, recording ion flow spectrum and mass spectrum
Ion flow spectra of the Rabdosia Rubescens leaf aqueous extract powder were determined and recorded according to the above conditions (see figure 1 of the specification).
Example 3 specifying the structure of 36 Components in Rabdosia Rubescens leaf aqueous extract powder
The UPLC chromatogram of example 2 was coupled to a mass spectrum and the UPLC-mass spectrum of the rabdosia rubescens leaf aqueous extract powder was determined. The mass spectrometry conditions are two modes of electrospray ionization, positive and negative ions. The ion mode parameters comprise that the capillary tube voltage is 1000V, the desolvation air flow rate is 800L/h, the temperature is 450 ℃, the source temperature is 120 ℃, the taper hole air flow rate is 50L/h, the spraying air pressure is 6bar, the fragmentation voltage is 20-45V, the sampling cone voltage is 6V, the acquisition mode is an MSE continuum resolution mode, the data acquisition range of the ratio (m/z) of the mass number of the charged particles to the charge number is 100-1500, the Trap fragmentation voltage of the low-energy channel is 6V, the gradient voltage of the Trap fragmentation voltage of the high-energy channel is 20-60V, LE (leucine enkephalin) is selected as a mass lock to acquire m/z, and the range is 100-1500. 36 independent peaks separated over 45 minutes. The structural assignment of these peaks (in order of peaks from left to right in the total ion current spectrum) according to the mass spectrometry fragmentation law is given in table 2.
Table 2 shows the retention time of the peak-corresponding component, the mass number of the negative ion, the structure and the name of the negative ion in the total ion current spectrum
Example 4 evaluation of DPPH radical scavenging Activity of Rabdosia Rubescens leaf aqueous extract powder
DPPH is a stable nitrogenous radical that can be rapidly scavenged by protic radical scavengers. The activity of the proton radical scavenger DPPH in food and biological systems can be measured on a paramagnetic resonance apparatus. Antioxidant scavenging activity from natural sources can also be measured by DPPH on a paramagnetic resonance spectrometer. According to the third peak in the paramagnetic resonance spectrum, the concentration-dependent removal of nitrogen radicals from the powder of an aqueous extract of Rabdosia Rubescens (Hemsl.) Hara leaves is disclosed. The results are shown in FIG. 38. From FIG. 38, it can be seen that the peak intensity of nitrogen radicals is gradually decreased when the concentration of the aqueous extract powder of Rabdosia Rubescens (Hemsl.) Hara leaf is gradually increased from 0.00mg/mL,0.20mg/mL,0.39mg/mL, 0.78mg/mL,1.56mg/mL,3.13 mg/mL. It can be seen that the aqueous extract powder of Rabdosia rubescens leaves is an excellent therapeutic agent for DPPH-induced oxidative stress.
Claims (5)
1. A Rabdosia rubescens leaf water extract powder is characterized in that the Rabdosia rubescens leaf water extract powder contains 25 quinic acid compounds; wherein the 25 kinds of quinic acid compounds are 3-O- [ E-2- (3-carboxyl-1-propylene carbonyl oxygen) -3, 5-diformyl oxygen-4- (3-carboxyl-2-propylene carbonyl oxygen) -6- (6-carboxyl-1, 3-hexadiene carbonyl oxygen) cinnamoyl ] quinic acid, 3-O- [ E-2- (6-hydroxyl-1-hexene carbonyl oxygen) -3- (4-hydroxyl-1-butylene carbonyl oxygen) -4- (3-carboxyl-1-propylene carbonyl oxygen) -5-methoxy-6- (5-carboxyl-1-pentene carbonyl oxygen) cinnamoyl ] quinic acid, 3-O- [ E-2- (3-carboxypropylcarbonyloxy) -3, 5-dimethoxy-4- (3-carboxypropylcarbonyloxy) -6- (6-carboxyhexylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (6-hydroxyhexylcarbonyloxy) -3, 5-dicarboxyloxy-4- (3-hydroxypropionyloxy) -6- (6-carboxyhexylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (7-carboxy-1, 3-heptadienoyloxy) -3, 4-bis (3-carboxy-1-propenoyloxy) -5-formyloxy-6- (6-carboxy-1, 3-hexadienecarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (7-carboxy-1-heptenecarbonyloxy) -3- (6-hydroxy-1-hexenecarbonyloxy) -4- (3-carboxy-1-propenylcarbonyloxy) -5-formyloxy-6- (6-carboxy-1-hexenylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (4-hydroxybutylcarbonyloxy) -3, 4-bis (3-carboxypropylcarbonyloxy) -5-formyloxy-6- (6-carboxy-1-hexenylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (5-carboxy-1-pentenylcarbonyloxy) -3-carboxyethylcarbonyloxy) Acyloxy-4, 6-bis (3-carboxypropenoyloxy) -5-formyloxy cinnamoyl ] quinic acid, 3-O- [ E-2, 3-bis (3-carboxy-1-propenylcarbonyloxy) -4- (3-carboxypropenoyloxy) -5-carboxyacetoxy-6- (4-carboxy-1-butenylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2,3, 4-tris (4-hydroxybutenylcarbonyloxy) -5-formyloxy-6- (6-carboxy-1, 3-hexadienylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (4-hydroxy-1, 3-butadienylcarbonyloxy) -3, 4-bis (3-carboxy-1-propenecarbonyloxy) -5-formyloxy-6- (6-carboxy-1, 3, 5-hexatrienylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (4-hydroxy-1, 3-butadienecarbonyloxy) -3-carbonoyloxy-4- (3-carboxy-1-propenecarbonyloxy) -5-formyloxy-6- (4-carboxy-1, 3-butadienecarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 3-bis (3-carboxypropylcarbonyloxy) -4- (3-carboxypropyloxy) -5-formyloxy-6- (6-carboxy-1-hexenylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 3-bis (3-carboxypropylcarbonyloxy) -4- (3-hydroxypropionyloxy) -5-hydroxymethyl-6- (5-carboxypentylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 6-bis (5-carboxy-1-pentenoyloxy) -3- (3-carboxypropylcarbonyloxy) -4-carboxyacetoxy-5-methoxycinnamoyl ] quinic acid, 3-O- [ E-2- (8-carboxy-1-octenecarbonyloxy) -3- (3-carboxypropylcarbonyloxy) -4- (7-carboxy-1-heptenecarbonyloxy) -5-carboxyacetoxy-6- (4-carboxy-1-butenylcarbonyloxy) Cinnamoyl ] quinic acid, 3-O- [ E-2- (9-hydroxy-1-nonenecarbonyloxy) -3- (4-hydroxybutanecarbonyloxy) -4- (8-hydroxy-1-octenecarbonyloxy) -5-methoxy-6- (4-carboxy-1-butenylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (7-carboxy-1, 3, 5-heptatrienylcarbonyloxy) -3, 4-bis (5-carboxy-1, 3-pentadienylcarbonyloxy) -5-carboxyacetoxy-6- (6-carboxy-1, 3-hexadienylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (4-hydroxy-1-butenylcarbonyloxy) -3- (4-carboxy-1-butenoyloxy) -4- (3-carboxypropenyloxy) -5-carboxyacetoxy-6- (4-carboxy-1, 3-butadienoyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (7-carboxy-1, 3, 5-heptatrienylcarbonyloxy) -3- (8-hydroxy-1, 3,5, 7-octatetraenylcarbonyloxy) -4, 5-bis (4-carboxy-1, 3-butadienoyloxy) -6- (6-carboxy-1, 3, 5-hexatrienylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (4-hydroxybutanecarbonyloxy) -3, 4-bis (3-carboxypropylcarbonyloxy) -5- (3-hydroxypropionyloxy) -6- (4-carboxybutylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 6-bis (5-carboxy-1-pentenoyloxy) -3- (3-carboxypropylcarbonyloxy) -4- (3-carboxypropylcarbonyloxy) -5-hydroxycinnamoyl ] quinic acid, 3-O- [ E-2, 5-bis (7-carboxy-1, 3-heptadienoyloxy) -3- (6-hydroxy-1, 3-hexadienoyloxy) -4- (4-carboxy-1, 3-butadienoyloxy) -6- (6-carboxy-1, 3-hexadienecarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2- (5-hydroxy-1-pentenecarbonyloxy) -3, 4-bis (4-carboxy-1-butenecarbonyloxy) -5-carboxyacetoxy-6- (4-carboxy-1, 3-butadienecarbonyloxy) cinnamoyl ] quinic acid and 3-O- [ E-2, 5-dicarboxyacetoxy-3- (10-carboxy-1, 3,5, 7-decatetraenecarbonyloxy) -4- (8-carboxy-1, 3, 5-octatrienecarbonyloxy) -6- (6-carboxy-1, 3-hexadienecarbonyloxy) cinnamoyl ] quinic acid.
2. The rabdosia rubescens leaf aqueous extract powder of claim 1 further comprising 11 quercetin-based compounds; wherein the 11 kinds of quercetin compounds are 3-O-glucoside-2 '-formyloxy-3' - (3-carboxyl acryloyloxy) -4 '-carboxyl acetyloxy-5' - (3-carboxyl-1-propylene carbonyloxy) -6 '- (5-hydroxyl-1-pentene carbonyloxy) quercetin, 3-O-glucoside-2' -formyloxy-3 '- (10-carboxyl-1, 3-decadiene carbonyloxy) -4' - (5-carboxyl-2-pentene carbonyloxy) -5 '- (3-carboxyl-1-propylene carbonyloxy) -6' - (5-hydroxyl-1-pentene carbonyloxy) quercetin, 3-O-glucoside-2 '-formyloxy-3' - (6-carboxy-1-hexenecarbonyloxy) -4 '- (6-hydroxy-2-hexenecarbonyloxy) -5' - (3-carboxy-1-propenecarbonyloxy) -6 '- (5-hydroxy-1-pentenecarbonyloxy) quercetin, 3-O-glucoside-2' -formyloxy-3 '- (7-hydroxy-1, 3, 5-heptatrienylcarbonyloxy) -4' - (4-carboxy-2-butenecarbonyloxy) -5 '- (3-carboxy-1-propenecarbonyloxy) -6' - (7-carboxy-1, 3-heptadienylcarbonyloxy) quercetin, 3-O-glucoside-2 '-formyloxy-3' - (8-carboxy-1, 3, 5-octatrienylcarbonyloxy) -4 '- (5-carboxy-1-pentenylcarbonyloxy) -5' - (5-carboxy-1, 3-pentadienylcarbonyloxy) -6 '- (6-hydroxy-1, 3, 5-hexatrienylcarbonyloxy) quercetin, 3-O-glucoside-2' -formyloxy-3 '- (4-carboxybutylcarbonyloxy) -4' - (3-carboxypropylcarbonyloxy) -5 '- (4-hydroxybutylcarbonyloxy) -6' - (5-hydroxy-1-pentenylcarbonyloxy) quercetin, 3-O-glucoside-2 ' -formyloxy-3 ', 6 ' -bis (7-hydroxy-1-heptenecarbonyloxy) -4 ' - (4-carboxy-1-butenylcarbonyloxy) -5 ' - (3-carboxy-1-propenylcarbonyloxy) quercetin, 3-O-glucoside-2 ' -formyloxy-3 ' - (7-carboxy-1, 3, 5-heptatrienylcarbonyloxy) -4 ', 5 ', 6 ' -tris (5-carboxy-1, 3-butadienylcarbonyloxy) quercetin, 3-O-glucoside-2 ' -formyloxy-3 ' - (7-carboxy-1, 3, 5-heptatrienylcarbonyloxy) -4 ', 5 '-bis (5-carboxy-1, 3-pentadienoyloxy) -6' - (7-carboxy-1, 3-heptadienoyloxy) quercetin, 3-O-glucoside-2 '-formyloxy-3' - (4-carboxybutylcarbonyloxy) -4 '- (3-carboxypropylcarbonyloxy) -5' - (4-hydroxybutylcarbonyloxy) -6 '- (5-hydroxypentanoyloxy) quercetin and 3-O-glucoside-2' -methoxy-3 '- (7-hydroxy-1-heptenecarbonyloxy) -4', 5 '-bis (5-hydroxy-1-pentenoyloxy) -6' - (8-hydroxy-1, 3-octadienecarbonyloxy) quercetin.
3. A method of preparing an aqueous extract powder of rabdosia rubescens leaf of claim 1 or 2, comprising: cleaning Rabdosia Rubescens (Hemsl.) Hara leaf with water, soaking in distilled water under heating while stirring slowly, filtering, and concentrating the filtrate under reduced pressure to obtain powder which is Rabdosia Rubescens (Hemsl.) Hara leaf water extract powder.
4. The preparation method as claimed in claim 3, wherein the Rabdosia Rubescens (Hemsl.) Hara leaves are washed with tap water, preferably distilled water at 50-100 deg.C for 0.5-4 hours and stirred at 200-400rpm/min, cooled to room temperature, filtered, the filter cake is washed with distilled water 3 times, the combined filtrate is concentrated under reduced pressure to obtain powder of Rabdosia Rubescens (Hemsl.) Hara leaf water extract powder.
5. Use of the powder of aqueous extract of Rabdosia Rubescens (Hemsl.) Hara leaf of claim 1 or 2 for the preparation of a medicament against oxidative stress.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011233389.6A CN112353844A (en) | 2020-11-06 | 2020-11-06 | Rabdosia rubescens leaf aqueous extract powder, preparation thereof, radical scavenging action and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011233389.6A CN112353844A (en) | 2020-11-06 | 2020-11-06 | Rabdosia rubescens leaf aqueous extract powder, preparation thereof, radical scavenging action and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112353844A true CN112353844A (en) | 2021-02-12 |
Family
ID=74509655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011233389.6A Withdrawn CN112353844A (en) | 2020-11-06 | 2020-11-06 | Rabdosia rubescens leaf aqueous extract powder, preparation thereof, radical scavenging action and use thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112353844A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115124499A (en) * | 2022-07-29 | 2022-09-30 | 中国中医科学院中药研究所 | Compound for targeted killing of aged cells and application thereof |
-
2020
- 2020-11-06 CN CN202011233389.6A patent/CN112353844A/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115124499A (en) * | 2022-07-29 | 2022-09-30 | 中国中医科学院中药研究所 | Compound for targeted killing of aged cells and application thereof |
| CN115124499B (en) * | 2022-07-29 | 2023-12-26 | 中国中医科学院中药研究所 | Compound for targeted killing of aged cells and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Li et al. | HPLC fingerprint analysis of Phyllanthus emblica ethanol extract and their antioxidant and anti-inflammatory properties | |
| US6440468B1 (en) | Method for obtaining apolar and polar extracts of curcuma and applications thereof | |
| Chakraborty et al. | Cytotoxicity and antimicrobial activity of Colocasia esculenta | |
| Joseph | Enhanced neuroprotective effect of fish oil in combination with quercetin against 3‐nitropropionic acid induced oxidative stress in rat brain | |
| Hsu et al. | Anti-inflammatory effects of phenolic compounds isolated from the flowers of Nymphaea mexicana Zucc. | |
| EP2779845B1 (en) | Chicory extract and method of preparing | |
| Xia et al. | Antioxidant activity of Chinese mei (Prunus mume) and its active phytochemicals | |
| Liao et al. | Chemical compositions, anti-inflammatory, antiproliferative and radical-scavenging activities of Actinidia callosa var. ephippioides | |
| de Souza et al. | Radical scavenger capacity of jabuticaba fruit (Myrciaria cauliflora) and its biological effects in hypertensive rats | |
| JP6210142B2 (en) | Composition for preventing and / or treating cognitive impairment | |
| Adewusi et al. | Isolation of cycloeucalenol from Boophone disticha and evaluation of its cytotoxicity | |
| CN112353844A (en) | Rabdosia rubescens leaf aqueous extract powder, preparation thereof, radical scavenging action and use thereof | |
| Shi et al. | Screening of radical-scavenging natural neuroprotective antioxidants from Swertia chirayita | |
| Dai et al. | High value-added application of two renewable sources as healthy food: the nutritional properties, chemical compositions, antioxidant, and antiinflammatory activities of the stalks of Rheum officinale Baill. and Rheum tanguticum Maxim. ex Regel | |
| KR101717889B1 (en) | Composition comprising scirpusin a and scirpusin b and anti-obesity potential thereof | |
| Park et al. | Phytochemical profiles and in vitro anti-inflammatory properties of Perilla frutescens cv. Chookyoupjaso mutants induced by mutagenesis with γ-ray | |
| Ghorbani et al. | Effect of Long-term Administration of Ferula Gummosa Root Extract on Serum Oxidant-antioxidant Status: Effect of long-term administration of Ferula gummosa root extract on serum oxidant-antioxidant status | |
| CN112353842A (en) | Rabdosia rubescens stem water extract powder, preparation thereof, free radical scavenging effect and application | |
| Mohadjerani et al. | Evaluation of total phenolic content and antioxidant activity of Nelumbo nucifera seed from north of Iran | |
| CN101824021A (en) | Method for extracting catechin small molecules in lotus root and application thereof | |
| KR20160141463A (en) | Anti-oxidation and anti-inflammatory composition comprising the extract of aralia continentalis | |
| Atun et al. | Identification and antioxidant activity test of bioactive compound produced from ethanol extract of temukunci (Boesenbergia rotunda) | |
| KR100635451B1 (en) | ROSA LAEVIGATA MICHX EXTRACT HAVING AN ACTIVITY OF INHIBITING AMYLOID beta;-INDUCED BRAIN CELL DAMAGES | |
| KR20080103321A (en) | Pharaceutical composition containing extracts from polygonatum falcatum for the preventing or treating dementia and method of production thereof | |
| RU2366445C1 (en) | Method for making hepatoprotector |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20210212 |