Honey fraction

Patent metadata

Field	Value
Publication number	US-11020439-B2
Application number	US-201615577305-A
Country	US
Kind code	B2
Filing date	May 19, 2016
Priority date	May 29, 2015
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

The present invention provides a honey fraction obtainable by a method comprising (a) obtaining an absorbed component by causing honey to be brought into contact with an adsorbent, (b) obtaining an organic solvent fraction by eluting the absorbed component with an organic solvent that is acetone, ethyl acetate, or ethanol, and (c) obtaining a honey fraction from the organic solvent fraction.

First claim

The invention claimed is:

1. A dosage form comprising a honey fraction, where the honey fraction is obtainable by a method comprising:
(a) obtaining an absorbed component by causing honey to be brought into contact with an adsorbent,
(b) obtaining an organic solvent fraction by eluting the absorbed component with an organic solvent that is acetone, ethyl acetate, or ethanol, and
(c) obtaining a honey fraction from the organic solvent fraction, wherein the dosage form is selected from the group consisting of an uncoated tablet, a sugar-coated tablet, an effervescent tablet, a film-coated tablet, a chewable tablet, a lozenge, a capsule, a pill, fine granule, granule, emulsion, and injection,

wherein Step (b) further comprises at least one step selected from the group consisting of Step (b-1), Step (b-2), and Step (b-3),
(b-1) obtaining, as the organic solvent fraction, a fraction which has a spot at a Rf value in a range of 0.49 to 0.55, which is colored with an anisaldehyde sulfuric acid reagent and a spot at a Rf value in a range of 0.56 to 0.62, which is less colored than the aforementioned spot, when the absorbed component eluted with the organic solvent is fractionated by an elution time, and is developed with a solvent in which a mixing ratio of hexane/ethyl acetate is 4/1 in a thin layer chromatography using silica gel,
(b-2) obtaining, as the organic solvent fraction, a fraction which has spots at a Rf value 0 and in a range of 0.54 to 0.94, which are colored with a doragendorf reagent when the absorbed component eluted with the organic solvent is fractionated by the elution time, and is developed with a solvent in which the mixing ratio of chloroform/methanol/acetate is 9/1/1 in the thin layer chromatography using silica gel,
(b-3) obtaining, as the organic solvent fraction, a fraction which is detected with a retention time in a range of 2.0 to 4.0 minutes, and has a peak which has molecular ion peaks of m/z438 [M+H] and m/z436 [M−H] in a case where the absorbed component eluted with the organic solvent is fractionated by the elution time, and is measured under the following conditions in liquid chromatography mass spectrometry;

(Measuring Conditions)
Column: Acquity UPLC BFH C18 (φ2.1×100 mm, manufactured by Waters Corporation)
Flow rate: 0.4 mL/min
Column temperature: 40° C.
Solvent: 5% B (0 to 0.25 min), 5 to 100% B (0.25 to 10 min, linear gradient), 100% B (10 to 12 min), 5% B (12 to 15 min)
A: 0.05% of formic acid aqueous solution, B: 100% of acetonitrile
Injection volume: 2 μl.

2. The honey fraction according to claim 1 , wherein the absorbed component eluted in Step (b) is a component which is not eluted with water or methanol.

3. The honey fraction according to claim 1 , wherein the organic solvent is acetone.

4. The honey fraction according to claim 1 , wherein the method further comprises removing a component which is elutable with water from the absorbed component before Step (b).

5. The honey fraction according to claim 1 , wherein the method further comprises removing a component which is elutable with methanol, a methanol aqueous solution, or an ethanol aqueous solution from the absorbed component before Step (b).

6. The honey fraction according to claim 1 , wherein Step (b) further comprises Step (b-4) obtaining, as the organic solvent fraction, a fraction which satisfies at least one condition of the following conditions (1) and (2) by further fractioning the fraction obtained in Step (b-2) with a reverse phase adsorbent,
(1) Having a spot at a Rf value in a range of 0 to 0.22, which is colored with a doragendorf reagent when the development is performed with a solvent in which the mixing ratio of chloroform/methanol/acetate is 9/1/0.3 in the thin layer chromatography using silica gel,
(2) Having at least one spot selected from the group consisting of the spots at Rf values in a range of 0.02 to 0.09, 0.10 to 0.20, and 0.30 to 0.53, which is colored with a ninhydrin reagent when the development is performed with a solvent in which the mixing ratio of chloroform/methanol/water is 1/1/0.3 in the thin layer chromatography using silica gel.

7. A method of activing an opioid comprising administering an effective amount of the honey fraction according to claim 1 to a subject in need thereof.

8. A method of suppressing cough or relieving pain comprising administering an effective amount of the honey fraction according to claim 1 to a subject in need thereof.

Assignees

• Yamada Bee Co Inc
• Univ Tokyo Science Found

Inventors

• Isohama Yoichiro
• Horie Ichiro
• Tani Hiroko
• Kimura Yuka
• Yoshimatsu Maiko
• NAKATSUKA Tae

Classifications

• A61P11/14

  Antitussive agents · CPC title

• A61P25/04

  Centrally acting analgesics, e.g. opioids · CPC title

• A61K35/63

  Arthropods (aquatic crustaceans A61K35/612) · CPC title

• B01J20/286

  Phases chemically bonded to a substrate, e.g. to silica or to polymers · CPC title

• A61K35/644 Primary

  Beeswax; Propolis; Royal jelly; Honey · CPC title