JPH05156247A - New benzopyrane derivative - Google Patents

Abstract

PURPOSE:To provide a new benzopyrane compound which can be used as a naturally occurring antioxidant instead of tocopherol and can be applied to food, beverage and medicines, too. CONSTITUTION:A new benzopyrane derivative of formula I (R is H, acyl), for example, the compound of formula II. The compound is obtained by culturing a kind of bread yeast, Saccharomyces-cerevisiae, crushing the dried cell bodies, extracting them with a chloroform-methanol (2:1) mixture, filtering the extract, combining the filtrate with distilled water, stirring and settling, separating the lower layer, than distilling off the solvent and subjecting the residue to silica-gel column chromatography and high-performance liquid chromatography to effect the purification.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel benzopyran derivative. More specifically, the present invention relates to a novel benzopyran derivative having antioxidant activity, which is useful for foods and drinks, pharmaceuticals and the like.

[0002]

2. Description of the Related Art Conventionally, various antioxidants have been developed and used for various purposes. However, many of these antioxidants are industrially produced by chemical synthesis, and their number is extremely small as a natural antioxidant substance. In fact, only tocopherols have been practically used as antioxidants for fats and oils.

For this reason, the search and practical development of natural antioxidant substances that can be used in foods and drinks have been pursued, but so far, promising ones have not been realized yet. .. In recent years, cancer, arteriosclerosis,
Furthermore, the relationship between phenomena such as aging and the oxidative reaction in the living body has been attracting attention, and expectations are high for antioxidant substances as drugs capable of controlling the oxidative mechanism in the living body.

The present invention has been made under such a background, is useful as a natural antioxidant substance replacing tocopherol, and is expected to be applied to foods and drinks and medical products. The aim is to provide new natural antioxidants.

[0005]

The present invention has the following formula (I) for solving the above problems.

[0006]

[Chemical 2]

A novel benzopyran derivative represented by the formula (wherein R represents a hydrogen atom or an acyl group) is provided. The compound represented by the above formula of the present invention has antioxidant activity as a novel substance derived from a natural product, and is useful as a raw material for foods and drinks, medical products, chemical products and the like. The benzopyran derivative represented by the above general formula is a typical yeast, and is used as baker's yeast, Saccharomyces cerevisi.
Those obtained separately from ae and ester compounds thereof are noted as novel substances derived from natural products. Of course, chemical synthesis is also possible.

When R in the above formula (I) is an acyl group, the acyl group is exemplified by an acyl group derived from an aliphatic carboxylic acid such as an acetyl group or a palmitoyl group. Chemical conversion can be carried out according to a conventional method. Examples are shown below to describe the novel benzopyran derivative of the present invention in more detail.

[0009]

EXAMPLES Example 1 500 g of dried Saccharomyces cerevisiae cells was treated with a ball mill overnight and crushed. 5 l of chloroform: methanol mixture (2: 1) was added thereto, and the mixture was stirred at room temperature for 2 hours and then filtered. 1.25 l of distilled water was added to the filtrate, and the mixture was stirred, allowed to stand until the lower layer became transparent, and then the lower layer was separated. The solvent was distilled off under reduced pressure to obtain 46.7 g of extract. Silica gel 60 (Nacalai Tesque, Inc.)
Column) (4 cm diameter × 27 cm length) packed with the product, and mixed with n-hexane: diethyl ether (90: 1).
It was developed in 0) and the fraction having an antioxidant effect was collected. The solvent was distilled off under reduced pressure to obtain 659 mg of an oily substance. This fraction was further added to a silica gel 60 column (2 cm diameter x 35 cm).
(cm length), the mixture was developed with an n-hexane: diethyl ether mixed solution (92: 8), and the fraction having an antioxidant action was collected to obtain 109 mg of an oily substance. Then, this was repeatedly injected into high performance liquid chromatography under the following operating conditions as a solution of a mixed solution of methanol: diethyl ether (1: 1), and a peak component with a retention time of about 18.6 minutes was collected.

<Operation conditions for high performance liquid chromatography> Column: ODS (Cosmo Seal 5C ₁₈ , 1 cmφ × 2)
5 cm, manufactured by Nacalai Tesque, Inc. ・ Eluent: Methanol ・ Flow rate: 4 ml / min ・ Detection: UV 283 nm By removing the solvent under reduced pressure, a slightly yellow oily substance,
16.0 mg was obtained. This purified product was a benzopyran derivative having the following chemical structure of C ₃₉ H ₅₈ O ₄ .

[0011]

[Chemical 3]

UV: (ethanol) λ _max = 274 nm · E _{1 cm} ^1%
= 165 λ _max = 330 nm, E _{1 cm} ^1% = 62.3 ¹ H-NMR: (500 MH _Z , CDCl ₃ : FIG. 1) Mass spectrum: (EI-MS, FIG. 2) Example 2 Example 2 Obtained in Example 1. Purified product (3.4 mg) and pyridine (0.8 ml)
Was dissolved in and the acetylation reaction was performed using acetic anhydride.

As a result, 3.4 mg of the compound of the following formula, C ₄₁ H ₆₀ O _5, was obtained.

[0014]

[Chemical 4]

¹ H-NMR: (500 MH _Z , CDCl ₃ : FIG. 3) Example 3 The antioxidant activity of the purified product obtained in Example 1 was evaluated. Sample concentration of 2 using α-tocopherol as a control
The activities were compared at 5 and 50 μg / ml. The results are shown in Table 1.

[0016]

[Table 1]

The product of the present invention comprises 50 parts of α-tocopherol.
It was confirmed to have an antioxidant effect of about%.

[Brief description of drawings]

1 is an NMR spectrum diagram of the compound of Example 1. FIG.

2 is a mass spectrometric spectrum diagram of the compound of Example 1. FIG.

3 is an NMR spectrum diagram of the compound of Example 2. FIG.

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[Procedure amendment]

[Submission date] June 5, 1992

[Procedure Amendment 1]

[Document name to be amended] Statement

[Name of item to be amended] Claims

[Correction method] Change

[Correction content]

[Claims]

[Chemical 1] (R in the formula represents a hydrogen atom or an acyl group.) A novel benzopyran derivative.

Claims (1)

[Claims] 1. The following formula (I): (R in the formula represents a hydrogen atom or an acyl group.) An antioxidant comprising a novel benzopyran derivative.