# US 8,465,757 B2 · Nanoemulsion of resveratrol-phospholipid complex and method for preparing the same and applications thereof

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- Number: US 8,465,757 B2
- Document ID: US8465757B2
- Status: Granted
- Kind: B2
- Application number: 12/569,740
- Filed: 2009-09-29
- Published: 2010-11-25
- Granted: 2013-06-18
- Earliest claimed: 2009-05-20
- Assignees: Tsinghua University; Jiangsu Longliqi Bioscience Co. Ltd.
- Applicants: Mingxing Duan; Huafeng Zhou; Zemin Yan
- Inventors: Mingxing Duan; Huafeng Zhou; Zemin Yan
- Web page: https://patentgrep.com/patent/US8465757B2

## CPC

- A61K 31/05: Phenols {(cannabinoids A61K31/658)}
- A61K 8/06: Emulsions
- A61K 8/347: {Phenols}
- A61K 8/553: {Phospholipids, e.g. lecithin}
- A61K 9/1075: {Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers (A61K9/0026 takes precedence)}
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/24: containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
- A61P 3/06: Antihyperlipidemics
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 35/00: Antineoplastic agents
- A61P 39/06: Free radical scavengers or antioxidants
- A61Q 19/00: Preparations for care of the skin
- A61K 2800/21: Emulsions characterized by droplet sizes below 1 micron
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## Abstract

The present invention relates to a nanoemulsion of resveratrol-phospholipid complex, method for preparing the same and applications thereof. The nanoemulsion comprises: 1 part by weight of resveratrol, 2˜30 parts by weight of phospholipid, and 30˜490 parts by weight of an aqueous solution of polyol with the polyol concentration being 30˜99 percent by weight. The method comprises the steps of: a resveratrol-phospholipid complex being prepared, then the complex being dispersed into the aqueous solution of polyol to form a dispersion, and a nanoemulsion with particle size less than 200 nm being formed by homogenization of the dispersion with a high pressure homogenizer or Microfluidizer homogenizer. The nanoemulsion is miscible with water at any ratio, has high stability and high bioavailability, and thus can be widely used for preparation of cosmetics, pharmaceuticals or healthcare products.

## Claims

### Claim 1

A nanoemulsion of resveratrol-phospholipid complex comprising: 1 part by weight of resveratrol, 10-20 parts by weight of phospholipids, and 30-490 parts by weight of an aqueous solution of a polyol, the concentration of the polyol in the aqueous solution being 30-99 percent by weight of the aqueous solution; wherein the nanoemulsion is miscible with water at any ratio, and the particle diameter of the resveratrol-phospholipid complex in the nanoemulsion is less than 200 nm.

### Claim 2 (depends on 1)

The nanoemulsion according to claim 1, wherein the resveratrol is cis-resveratrol or trans-resveratrol; the phospholipid is at least one member selected from the group consisting of soybean lecithin, egg lecithin, cephalin, sphingomyelin, cardiolipin, lipositol; and the polyol is at least one member selected from the group consisting of glycerine, propylene glycol, 1,3-butanediol, oligosaccharides (n≦10), and polyethylene glycol 200-800.

### Claim 3 (depends on 1)

The nanoemulsion according to claim 1, wherein the particle diameter of the resveratrol-phospholipid complex is less than 100 nm.

### Claim 4 (depends on 1)

The nanoemulsion according to claim 1, wherein the particle diameter of the resveratrol-phospholipid complex is less than 50 nm.

### Claim 5 (depends on 1)

The nanoemulsion according to claim 1, wherein the amount of the aqueous solution is 50-400 parts by weight; and the polyol concentration of the aqueous solution is 50-99 percent by weight of the aqueous solution.

### Claim 6 (depends on 1)

The nanoemulsion according to claim 1, wherein the 1 part by weight of resveratrol and the 10-20 parts by weight of phospholipid firstly form a resveratrol-phospholipid complex; then the obtained resveratrol-phospholipid complex is mixed with the 30-490 parts by weight of the aqueous solution of polyol.

### Claim 7

A method for preparing a nanoemulsion comprising the following steps:
(1) stirring a mixture of 1 part by weight of resveratrol, 10-20 parts by weight of phospholipid and 0.5-5 parts by weight of a solvent at 20-60° C. until a transparent oily homogeneous liquid is obtained, wherein the solvent is at least one member selected from a group consisting of ethanol, acetone, ethyl acetate, methanol, and ethyl ether;
(2) removing the solvent from the homogeneous liquid obtained in step (1) by vacuum distillation at 20-50° C. to form a resveratrol-phospholipid complex;
(3) adding the resveratrol-phospholipid complex obtained in step (2) into 30-490 parts by weight of an aqueous solution of polyol at 20-60° C. temperature, and mixing by stirring in the meantime of the addition of the resveratrol-phospholipid complex into the aqueous solution, thereby forming a crude dispersion of resveratrol-phospholipid complex;
(4) homogenizing the crude dispersion obtained in step (3) with a high-pressure homogenizer or a Microfluidizer homogenizer for 2-10 times under a pressure of 200 bar to 1500 bar, thereby making the particle diameter of the resveratrol-phospholipid complex less than 200 nm.

### Claim 8 (depends on 7)

The method according to claim 7, wherein in step (4) the dispersion is homogenized for 3-8 times, under a pressure of 500 bar to 1500 bar.