JPS5953427A - Extract of stalk and skin of sweet potato and antilipemic agent - Google Patents

Abstract

PURPOSE:An antilipemic agent especially capable of being administered safely for a long period, containing an extract of stalk and skin of sweet potato comprising straight-chain aliphatic aldehyde homologues as main components. CONSTITUTION:A fat-soluble substance showing a gas chromatography chart shown by the figure, comprising straight-chain aliphatic aldehyde homologues shown by the formula I , formula II and formula III as main components, is extracted from stalk and skin of sweet potato with an organic solvent (e.g., benzene, etc.), and isolated by silica gel chromatography. Sweet potato harvested in January is preferable as the sweet potato, and the yield is high when ripened part of stalk near to the root is used. The extract of stalk and skin of sweet potato has antilipemic action, especially lowering action on serum cholesterol, and is useful as an antilipemic agent. It can be administered by any method, and a dose of 50-1,000mg/day/person may be medicated every day in the case of oral administration.

Description

DETAILED DESCRIPTION OF THE INVENTION Various searches have been carried out for the purpose of providing the present invention, a sugarcane stem peel extract and its active ingredients.

As a result, we succeeded in extracting a new fat-soluble substance from the peel of old cane stalks, and learned that this substance has antilipidemic effects, especially serum cholesterol-lowering effects.

The present invention has now been completed.

Old sweet potato is a well-known plant, and is generally used as a raw material for producing brown sugar by squeezing the sugar solution from its stems, and it has been conventionally done to extract physiologically active substances from the brown sugar.However, iJ3 Prior to the present invention, it was not possible to selectively collect the epidermis of the stems of . It's something that didn't exist.

The substance of the present invention is extracted from 11'' tuber bark using a solvent such as benzene, and isolated by silica gel column chromatography. However, the substance of the present invention is not specified by a single chemical structural formula, and is carried out as described below. As shown in FIG. 1 of the example, several peaks appeared in the gas chromatography of the nine substances of the present invention.

It turns out that the substance of the present invention is a mixture consisting of a plurality of substances. Among these components, the main ones are linear aliphatic aldehyde analogues, specifically C25H51CHO and CIT H550HO.

C, g) I aa CHO. In other words, if we take a mass spectrum of the main peaks among the several peaks in Figure 9, we can see that the substances corresponding to each peak differ in their carbon chains by two methylene groups each, and are a series of aliphatic homologs. Something turns out to be true. Furthermore, nuclear magnetic resonance spectra and infrared absorption spectra of the substance of the present invention and the substance obtained by reducing the substance of the present invention show that the aliphatic homologue contains a -CIIO group as a functional group and that the carbon chain is linear. It turns out that this is the case. Furthermore, the molecular ion mass M of the substance corresponding to each peak is mHz 3
80+rn/z 40B, mHz 436, so the linear aliphatic aldehyde congeners are specifically identified as above.

In summary, the two substances of the present invention contain the series of linear aliphatic aldehyde homologues specified herein as main constituents, and also contain substances corresponding to the remaining peaks in Figure 1 as constituents. It can be defined as a mixture of

Regarding the physical and chemical properties of the substance of the present invention, it can be mentioned that the substance of the present invention exhibits a wax-like state at room temperature, for example, 25°C, and is soluble in benzene.

Next, in order to produce the substance of the present invention, the following method may be performed, for example. First, scrape off the outer skin of the cane stem with a razor. In this case, lIr,t! It is better to use the one harvested in January, but it is better to use the mature part of the stem near the roots for higher yields.

Next, about 20 times the volume of benzene is added to the collected stem skin, heated for 9, eg, 40''C for 130 minutes, and the P solution is concentrated under reduced pressure under a stream of nitrogen gas to obtain a lipid-like substance.

The obtained lipid-like substance is applied to a silica gel column and eluted with benzene. Both relatively early elution fractions and having an Rf value of 0.60 to 0.65 in the thin layer chromatography described below are collected. By recrystallizing the crystals obtained from both collected components from benzene, 9 substances of the present invention can be obtained.

Thin layer chromatography using a TLC plate of silica gel G (manufactured by Merck & Co.),
n-hexane:benzene (1:1.
v/v).

The substance of the present invention has the effect of lowering serum cholesterol as shown in the experimental examples below. Therefore 9
An antilipemic agent containing the substance of the present invention as a main medicinal ingredient is possible. In particular, it is safe even when administered over a long period of time, and a safe antilipidemia agent can be provided. Since ancient times, many people have lived long lives in the Amami Okinawa region.

There is a theory that the cause of this is ``long-term consumption of brown sugar extracted from sweet potato.Therefore, research has been conducted on the relationship between physiologically active substances contained in brown sugar and lipid metabolism.2For example, the following As seen in the report.

Wood '49 Row Hoka: '95 gg Vol, 102
(1982) 666-669H, Sho et a.
t, : J, Natr, Sci, Vitamin
ol, Vol, 27°Nα5 (1981) 462
~470 Hiroko is crab nutrition! :Food Vo1.25
Na6 (1972) 462-465 However, the present invention was the first to discover that a fat-soluble component extracted from 11 tuber peels, rather than a brown sugar component, has a serum cholesterol-lowering effect. The antilipemic agent of the present invention may be administered by any method.

It is usually administered orally. In the case of keirl throw 4, adult 1
Approximately 150-1,000 rng may be administered daily.

The present invention will be explained in detail using the experimental examples described below.

Example Samples A control feed and a test feed having the ingredients shown in Table 1 were prepared and used as trial 1 of the experiment. Note that in Table 9, Wax refers to the 1゛ potato stem peel extract obtained in Experimental Example 1 described later.

Table 1 Control feed Test sample 5ucrose 64.7 64
．． 2Casein” 20,0
20.0Cellulose 4.0
4.0M1neral rnlx 4
．． 0 4. OVitammrmx
1.0 1.0Lard 5
．． 0 5.0Cbolesterol
1.0 1. O8odium cbolat
e O,30,3Fatty alco)to
l -Wax -0.5 Method 4110 male Wistar rats with an initial weight of 140 to 180 g were divided into groups of 6 mice per group and raised in a breeding room at a room temperature of 23 to 25°C for 14 days.

During the on-site period, the animals were provided with 1 bottle of food and 1 bottle of water ad libitum, and their food intake and body weight were measured every 11 intervals. Experiment finished? table.

After 16 hours of incubation, blood was collected by decapitation at 1.1.1 mWk.
Centrifuge the serum at 8.00 rpm for 30 minutes.
;(It was used for lipid analysis.

In addition, the liver was removed and liver lipids were extracted and subjected to analysis. Note that one analysis was conducted as follows.

Determination of serum and liver lipids 11 Serum and liver lipids were determined using chloroform:methanol (2
: 1. v/v), extracted and purified by the method of FOIC II et al., and then dissolved in a certain volume of petroleum ether.

Regarding this extract, the cholesterol content is 5per・ry
& Webb method, triglyceride is Flet
CBER method and lipid phosphorus (phospholipid and L7 multiplied by 25) were determined by the Gomori method.

result The results are shown in Tables 2 to 4.

From Tables 2 to 4, it is clear that the two substances of the present invention have a lowering effect on serum lipids and especially serum cholesterol.

The present invention will be explained in more detail with reference to the following examples.

Example 1 The epidermis of the old stems harvested in January was scraped off with a razor,
Part 28. Add 600ml of benzene to.

Heated at 60°C for 30 minutes, filtered while hot, and concentrated the Fl solution to dryness under reduced pressure at 40°C under nitrogen gas to obtain a white lipid-like substance 6.
．． 5g was obtained. Next, silica gel (more than 100 mesh)
) was previously washed with benzene, a lipid-like substance dissolved in benzene was placed on the column, and the column was eluted with benzene. Both fractions were subjected to silica gel thin layer chromatography using n-hexane:benzene (1:1. v/v) as a developing solvent, and the 11f value was 0.
I collected 62 yoribu. Both collected fractions were concentrated to dryness under a stream of nitrogen gas and crystallized with benzene to obtain about 1.8 g of a waxy substance. The obtained substance (1) is a substance of the present invention, and the following analysis results were obtained.

(1) Gas chromatography] Gas chromatography was performed on the substance (~) under the following conditions, and the results shown in Figure 1 were obtained.

Equipment: Hewle Packard, IIP
-5791A column: 3ni 1. D. X 17+1
．． lf Las column packing material: 3% 0V-1on
Cbromnsorb W/HP100-120 m
esh Temperature: Oven; 210°C → 260°C (5°C/book 0 riser!+A) Injection part; 260"C Detection part; 260°C Detector: FID carry Xp-=IIe, 40pSi (2) Gas chromatography/mass spectrometry! In Figure 1, the peak 2 with the most m, ill and its 0;
Gas chromatography/mass spectrometry was performed on the substances corresponding to peaks 1 and 3 located after i under the following conditions, and the results shown in FIGS. 2 to 7 were obtained.

2. Figures 2 and 3 show GC/EI/MS and GC/CI/Ms for the substance ① corresponding to peak 2 in Figure 1.
It is. FIGS. 4 and 5 show the GO/EI/ for the substance ■ corresponding to peak 1 in FIG.

J- and GC/CI/MS. Figures 6 and 7 show the QC/EI/
MS and GO/CI/'+1. , iS.

Equipment = II Hondenshi, JMS-DX300 & JM
A-3500 cysteno column: IIewleLL Packard, l;
'used silica capillary noram 0V-10
1,0,2mm 1. D-×12.5I split method temperature Ninonora lq; 150°C → 285°C (16
(°C/min temperature increase) Injection part; 260°C Separator; 280°C Ki4/Rear: ) I8. 2i)ll+L/min
(0,35/<47/c++, MS conditions: Ionization; Er&C [ (Reactant gas...isobutane) Ionization voltage; 30 eV Ionization current; 300 μA 1/11 speed voltage; 31τV From Figures 2 to 7 , 1:4 for matter ■, ■, ■
The main results are summarized in the table below.

In addition, when we measured the C height 5) resolution mass spectrum of the substance ■, m/z3! Jl) The molecular formula of (M-18') was C,,11,.

(3) Absorption Spectrum of Red 91#''; One-line absorption spectrum of red was taken under the following conditions for substance (1) and the results shown in FIG. 8 were obtained.

Equipment fi:, f: 11 spectroscopy, A-302 measurement range: 5000-330o++-' measurement method: Nuj
ol Paste Method 11111 Constant Temperature: Room Temperature (4) Nuclear Magnetic Resonance Spectrum A nuclear magnetic resonance spectrum was taken for material ① under the following conditions, and the results shown in Figure 2 were obtained.

Equipment: JEOL, JNM-FX 100 Measuring nucleus: 'II Internal standard: TMS Measuring solvent: C1) CI.

Measurement temperature: room temperature Next, dissolve substance ① in tetrahydrofuran.

An excess of NnBII was added, and the mixture was left at room temperature for 1 hour.

Thereafter, a large amount of water was added and the mixture was acidified with hydrochloric acid to perform chloroporum extraction. f; The filtered extract was recrystallized with acetate to obtain a colorless crystalline powder. The following analysis results were obtained for the crystalline powder (1) obtained with a melting point of 82° to 33°.

(5) Gas chromatography material (2) Gas chromatography (f-) was carried out under the same conditions as described above for substance (2), and the results shown in FIG. 10 were obtained.

(6) Infrared absorption spectrum The infrared absorption spectrum of material (2) was taken under the same conditions as described above, and the results shown in Figure 2 were obtained.

(7) Nuclear Magnetic Resonance Spectrum A nuclear magnetic resonance spectrum was taken under the same conditions as described above for the material (2), and the results shown in FIG. 12 were obtained.

From the results of Section 2, the following considerations can be made regarding substance ■.
jp will be posted.

Substance ■ is a mixture containing substances (j), <2), ■, etc., and the M ion substance M1 of each of substances θ), <2), ■ is mHz 380. mHz 408. mHz
It is 435. Next, when we compare the mass spectra of the substances γ'j (1) and (can) with the mass spectra of the substance (2), we find that they differ only in the M ions, and the fragmentation patterns themselves show the same pattern. Typical spectrum of chain hydrocarbon → homologue]
It is similar to the 4th quality 5 (separated by 1 liter, its strength increases as the number of molecules decreases). Therefore, it is supported that the substance α1 is a mixture of Chozhen Fatty Intestine Shimomotozan (2), ■, etc., which have the same functional group.

Regarding this functional group, there is a signal at around 9.8 ppm in the nuclear magnetic resonance spectrum, and there is a signal at around 1720r:+n' in the infrared absorption spectrum.

-CI-
It is suggested that there are 10 groups.

Also, from the results of high-resolution mass spectra, the mHz of substance (2) is 390. That is, 'tJln M −1
The molecular formula corresponding to 8 is C2AH5,1. Therefore, the actual f+ of ~1 ion is ITI/Z 40
The molecular formula corresponding to B is C, H,. 0 is supported.

Putting all the above together, substance ■ has C2□H,,0fIO as its main component, sono et al.
It is supported that it is a mixture containing Ll, oCIfO, etc. The hydrocarbon chain portion is presumed to be linear based on the fragmentation patterns of the nuclear magnetic resonance spectrum and mass spectrum.

Next, the substance (A) is subjected to an expletive source, and when looking at the nuclear magnetic resonance spectrum and infrared absorption spectrum of the resulting substance (■), the peak derived from the -CfIO group decreases, and the peak derived from the -CfIO group decreases and is replaced by an OH group. A new peak that appears to be derived from this is observed. From this, it can be seen that the substance ■ is C1) I.

. , it can be seen from the bottom 4-1 that it is a mixture of CHO homologs 1t.

Fruit b (I phrase 2 It'i+o of the waxy substance obtained in Example I, 7 g of 7° corn starch, and 90 g of mannitol rM
Combined L/, ] ]0%-Hydroxypropyl 7 Ruleau ethanol solution 2f] Knead with u + l, 11 times 0
Cylindrical granulation is performed using a No. 511111 screen and dried. The dried J and i+q products were sized and used as internal granules for antilipidemic agents.

[Brief explanation of drawings]

FIG. 1 corresponds to FIG. 1 described in the section (1) Gas chromatography of Example 1, and is a gas chromatograph of substance G). 2 to 7 are (2) gas chromatographs of Example 1. These correspond to FIGS. 2 to 7 described in the mass spectrometry section, and are mass spectra of substances (1), (g), and (2). FIG. 8 corresponds to FIG. 8 described in the section (3) Infrared absorption spectrum of Example 1, and is the infrared absorption spectrum of substance (1). FIG. 9 corresponds to FIG. 9 described in the section (4) Nuclear magnetic resonance spectrum of Example 1, and is a nuclear magnetic resonance spectrum of substance (A). FIG. 10 corresponds to FIG. 10 of Example 1 (5) Gas chromatograph, described in section f-, and shows that the substance (...)

[Substance CB treated with iii)] is a chromatograph. FIG. 11 corresponds to FIG. 11 described in the section (6) Infrared absorption spectrum of Example 1, and is the infrared absorption spectrum of the same two materials (Co., Ltd.). Corresponds to Figure 12 described in the section on resonance spectra, and in the same substance) O) fl Magnetism
1. Sound spectrum. Patent application Artificial Ichizai Co., Ltd. 11 Peak 3 □□□□□□□□□□□□ ') ICI 15 し15 I2 [6 Ekyo ``Garrison'',
= 0δ
Figure By 1, (. 1]9a, Rashi l 10 0ko1lr115:ノC] f+n1.n) Shi[11- 1 1:a12

Claims (1)

[Claims] (1) A licorice stem peel extract (2, patent claim 1. The antilipemic agent according to claim 1, wherein the antilipidemic agent (3) is a serum cholesterol lowering agent. blood drug