JPS5872523A - Antitumor agent - Google Patents

Abstract

PURPOSE:An antitumor agent, consisting of saponin component in soybeans and an excipient, and effective for a wide range of tumors. CONSTITUTION:An antitumor agent consisting of at least one or more soya saponins of the formula (R1 is alpha-L-rhamnopyranosyl(1 2)-beta-D-galactopyranosyl (1 2)-beta-D-glucuronopyranosyl, etc.) which are saponin components in soybeans having the following properties: Yellowish white - brown and odorless powder having a slight bitterness; readily soluble in methanol, etc., soluble in water and ethanol and slightly soluble in chloroform; neutral in a 1% aqueous solution; glucuronic acid, galactose, etc. obtainable from the water-soluble part by the hydrolysis; soya sapogenol A (C20H50O4) which is a constituent main genin obtainable from the water-insoluble part; positive to the Liebermann and Salkowski reactions; and the formation of lasting small bubbles by shaking in water. The saponin components are obtained by extracting and separating from soybeans, and purifying the resultant extract with a solvent.

Description

[Detailed description of the invention] The present invention is directed to soybean (Glycine w@x merr).
The present invention relates to an anti-tumor agent containing as an active ingredient a saponin component that can be extracted from irriginum.

It is known that various saponin substances are contained in natural plants and animals, and soybeans also contain multiple saponin substances. The chemical structures of several types of soybean saponin components have been clarified. (ch-em, Pharm, B
ull, Vol. 24, 11), pp. 121-129 (197
8th grade)].

It has been known that saponins exhibit hemolytic, insecticidal, and piscicidal physiological activities. From the results of research conducted by the inventors of the present invention, it has been found that soybean saponin components have a lipid peroxide suppressing effect and an antithrombin effect. In addition, it is also known to have an effect of increasing pressor pulse rate (Japanese Patent Application Laid-open No. 83958/1983). However, it is not known that soybean saponin components have antitumor effects.

- This invention was made based on the discovery that soybean saponin components have antitumor effects, and provides an antitumor agent comprising a soybean saponin component and a pharmaceutically acceptable excipient.

The saponin component of this invention can be obtained by extracting and separating soybeans and purifying it with a solvent, or by selectively adsorbing saponin from the extract using a resin adsorbent and purifying it. In this invention, the term 1 saponin component 1 refers to a mixture obtained by these methods that consists essentially of saponins only. It is also believed that this soybean saponin component is also contained in plants other than soybeans.

Examples of methods for obtaining saponin components from soybeans include the following methods.

That is, the soybean grain powder used as a raw material is defatted using a normal fat-soluble organic solvent such as hexane, and then its active ingredients are extracted using water or a lower aliphatic alcohol such as methanol or a hydrous lower aliphatic alcohol. , evaporate and concentrate the extract to obtain an extract. This is water saturated n-
Dissolve in butanol, add water to the solution, shake and leave to stand, separate the n-butanol layer and evaporate to dryness. Alternatively, the extracted extract may be dissolved in a mixture of n-butanol and water (1:l), left to stand, and the n-butanol layer separated and evaporated to dryness. This evaporation residue is dissolved in a lower aliphatic alcohol, stirred and poured into ether, and the resulting precipitate is collected by F to obtain soybean saponin.

Another method is to defatte soybean powder, add water,
Extract with lower alcohol or hydrous lower alcohol,
The concentrate is dissolved in water or water containing less than about 30 liters of lower alcohol, and the solution is contacted with a macro-reticular, porous, cross-linked polystyrene resin adsorbent (e.g. Selvachrom XAD) to release soybean saponin. After adsorption, soybean saponin is obtained by elution treatment with lower alcohol or about 30 liters or more of lower alcohol-containing water.

The extract thus obtained substantially contains saponin components and can be used as is as an active ingredient in the present invention.

The saponin component according to the present invention contains compounds of formulas (I) and (2) as described below, although the types and amounts of the components differ slightly depending on the type of soybean used as a raw material.

The properties and properties of this saponin component (soybean saponin) are as follows.

B. It is a yellowish-white to brown powder with a slightly bitter taste and is odorless. It is easily soluble in methanol and dilute methanol, soluble in water and ethanol, and sparingly soluble in chloroform, ether, hexane, and carbon tetrachloride.

A 1% aqueous solution is neutral.

C, infrared absorption 11L: pmax (X diw-le) 3400 (b), 3350 (b), 1720 (b) and 171G (b)
r) cff”I R: y(ILBr)3400(br
), 3350 (br), 2918.1734 (br),
1385 (b, 1074 * and 1027 cm-") Thin layer chromatography carrier nibrate Kieselgel 60F254 (Merck & Co.) Developing solvent: chloroform/methanol/water (6:4:1
) When a 1% ceric sulfate-10% sulfuric acid mixture was sprayed and heated, distinct autumn leaf-colored saponin spots appeared.

E. By acid hydrolysis, glucuronic acid, galactose, glucose, arabinose, □ rhamnose, and kyjirose are obtained from the water-soluble part, and Soyasapogenol A (csons・O4, melting point 310
~312℃), Nyasapoge/-ru B (CwH, oO
s, melting point 260-261°C), and a trace amount of Sawyer sapogenol C1D%E was also observed.

Herri-Berman reaction and Zarkolaski reaction are positive.

When added to water and shaken, persistent small bubbles are generated.

The saponin component of Matato is an edible soybean saponin that has no hemolytic effect and is extremely safe.
I%o3. SP a on/”f (7 sea urchins X, oral),
-1, OP or more/M (mouse, intraperitoneal)], and can be manufactured at low cost.

The saponin component in this invention includes soya saponins (Soymsapo) represented by the following formula (I) or
Contains at least one type of nins).

Formula (■): In the formula, 1ri is α-L-rhamnopyranosyl (1→2)-β
-〇-galactopyranosyl (l→2)-β-D-glucuronopyranosyl group, a-L-rhamnopyranosyl (1→2
)-a-L-arabinopyranosyl (l→2)-β-D-
It represents a glucuronopyranosyl group or a β-D-galactopyranosyl (1→2)-β-〇-glucuronopyranosyl group.

Formula (2): In the formula, R1 is β-〇-glucopyranosyl (1→2)-β
-D-galactopyranosyl-(1-2)-I-〇-glucuronopyranosyl group, - represents β-ri-glucopyranosyl(l→3)-α-L-arabinopyranosyl group. or R1 is β-D-galactopyranosyl-(l→2)-
In /-D-glucuronopyranosyl group, - represents β-〇-glucopyranosyl (l→3)-α-L-arabinopyranosyl group.

The saponins of formula (I) and formula (2) are saponins belonging to oleanane-based glycosides of triterpenes. Formula (I)
As individual specific names of the compound represented by, 3-0-
(α-L-rhamnopyranosyl (l → 2)-β-〇-galactopyranosyl (1 → 2)-β-〇-f-lucuronoviranosyl) - Soyasapogenol B (Soyasapogenol, C
--0 intestine 2-0, melting point 238-240℃): 3-0
-[α-L-Rhamnopyranosyl (l→2)-g-L-arabinopyranosyl (1→2)-β-〇-glucuronopyranosyl]-Nyasapogenol B (Sawyasaponin 1[
, (4yHTa011.3H,0, melting point 212-215
°C); 3-0-(β-D-galactopyranosyl (l→2
-)-1-D-Glucuronopyranosyl Soyasapogenol B (Sawyasaponin 1. C411) 1@101
4e2H10, melting point 215-216°C).

As individual specific names of the compound represented by formula (6),
3-0-(/-D-glucopyranosyl(l→2)-do-
D-galactopyranosyl (l→2)-β-〇-glucuronopyranosyl)-21-0-(β-〇-glucopyranosyl (l→3)-7-L-arabinopyranosyl to soya support Genol A (Sawyasaponin A1, Cll-~・4
-0, melting point 240-242°C), 3-0-(/-D-galactopyranosyl-(l→2)-
Door〒D-glucuronopyranosyl)-21-0-()-D
- Glucopyranosyl (1 → 3) - α-L-arabinopyranosyl] - Soyasapogenol A (Sawyasaponin 4,
Cgl-Os4@3H1O1 melting point 231-233℃)
can be mentioned.

Among these, the content of Soya Saponinae is the highest.

In addition to the saponins having the structures of formulas (1) and (2) described above, soybeans also contain extremely small amounts of saponins whose structures are undetermined and whose skeletons are the following soya sapogenols C, D, and K. These substances are also included in the saponin component of this invention.

R,! H Soyasapogenol CR R,,,-0CH4 Soyasapogenol DR1-0 Soyasapogenol E The above-mentioned side compounds are the soyasaponin (soybean edge saponin) obtained by the above-mentioned , e.g. chloroform/
It can be obtained by separating and purifying each component saponin by silica gel column chromatography, high performance liquid chromatography, etc. using a methanol/water system or 11-phthanol/acetic acid/water system developing solvent. However, from an economical point of view, it is preferable to use the saponins as a mixture rather than separating them into the individual constituent saponins.

The composition of this invention may be administered orally or parenterally. Oral dosage forms usually include powders, tablets, emulsions, capsules, teas, granules, and liquids (including tinctures, liquid extracts, spirits, suspensions, lemonades, syrups, etc.). It will be done. In addition, parenteral dosage forms include injections, drops, ointments, plasters, liquids (including alcoholic preparations, tinctures, lotions, etc.), poultices (poultices, baths), liniments, sprays, Examples include dusting agents, liniments (rubbing agents), creams, emulsions, and bath agents.

The dosage varies depending on the medical condition, but for oral preparations,
The saponin component can be effective by administering 50 to 500 η per day for adults, preferably 200 to 400 η, divided into 2 to 3 doses.

As solid or liquid excipients used herein, those known in the art are used. However, 1 as described below
It may be desirable to formulate the compound to contain the required number of doses.

Excipients in powders and other powders for internal use include lactose, starch, dextrin, calcium phosphate, calcium carbonate, synthetic and natural aluminum silicate, magnesium oxide, dry aluminum hydroxide, stearin, to name a few. Examples include magnesium acid, sodium bicarbonate, and dried horse mackerel.

The antitumor agent of this invention is effective against a wide range of tumors, but
For example, it is effective against lung cancer, uterine cancer, stomach cancer, and liver muscle.

Next, an example of producing the soybean saponin of the present invention will be shown.

Production Example 1 Soybean seed powder (1.011 g) was heated and extracted twice with 100 g of n-hexane for 1 hour each to defatte, and then heated and extracted with 100 g of methanol 1 to 2 times for 3 hours each.

After distilling the extract under reduced pressure to remove the solvent, the residue was diluted with 10 g of water-saturated n-butanol for about 1 hour each.
Dissolved while stirring on a steam bath. The obtained solution was washed three times with 3 J of n-butanol saturated water to remove contaminating sugars and pigments, and the separated water-saturated n-butanol layer was distilled under reduced pressure at 80°C or less and dried. Hardened. The residue was dissolved in 31 g of methanol and poured into 60 g. of ether with stirring. After standing for one day, the precipitate was filtered and dried under reduced pressure at 60°C or lower to obtain soybean saponin 3 (H').

Production Example 2 Soybean seed powder 104 was mixed twice with 100) n-hexane.
The mixture was extracted by heating and defatted for several hours. The defatted and dried product was extracted with 10 g of 99 g methanol and heated at 60° C. for 1 hour. This operation was repeated three times, and the filtrates were combined and concentrated and dried under reduced pressure at a temperature of 60° C. or lower.

A solution of this residue dissolved in 10 G@l of water was added to the synthetic resin adsorbent Selvachrom X A D-1ype201.
Saponin was dispersed in water (3 Jf) and injected from the top of a Selvachrom X A D-t7pe 2 column packed in a column with an inner diameter of 8α, and passed through at a flow rate of 20 d1 min to adsorb saponin. Further, water was added to remove the impurities until the flowing material was no longer colored.

After the coloring disappears, add 99 liters of methanol at a flow rate of 10 d.
The saponin adsorbed on Selvachrome was eluted by flowing down at a rate of 1 minute. Completion of elution was confirmed by thin layer chromatography [Carrier 7: Keyil Gel F254. Solvent': Chloroform/methanol/water (65:35:1G lower layer),
Detection: l-cerium sulfate-10 after spraying with sulfuric acid 10
Heated at 5°C for 5 minutes]. Saponin was completely eluted with 5 streams of 99-methanol. The obtained eluate was evaporated to dryness at a temperature below 60°C, and the residue was dried at 60°C to obtain yellowish-brown-white soybean saponin component powder 32f! I got it.

Production Example 3 101 ft of soybean seed powder was heated and extracted twice with 100 g of n-hexane to defatte it. The defatted powder was extracted twice with 98 gallons of methanol and 100 gallons of methanol at boiling temperature for 3 hours each time. The extract was subjected to vacuum distillation to obtain a 1.4-yield extract. Add this extract to a mixture of butanol and water (1:1).
007, dispensed and left to stand. The n-butanol transfer portion was separated, and the solvent was distilled off under reduced pressure, then dissolved in 5 g of 98 liters of methanol, and added little by little to 1007 ml of ethyl ether.

The resulting precipitate was separated into P, and then water-saturated n-butanol 107 was added to the precipitate to separate it into an insoluble part and a soluble part.

The soluble portion was distilled under reduced pressure to completely remove the solvent, leaving a residue of 64
I got an F. This residue is n-butanol:water (1:2)
It was distributed using Mixture 107. The water transition part was distilled off under reduced pressure.
The obtained residue (32F) was subjected to silica gel column chromatography [Silica gel G (manufactured by Merck & Co., Ltd., 70-230 mesh), chloroform-methanol-water (chloroform-methanol-water (Merck) as eluent)]
The lower layer of 65:35:1G to 6:4:1)) was applied. The eluate was subjected to thin layer chromatography [support: silica gel]
254, Developing Solvent Co., Ltd. Chloroform-methanol-water (
6:4:1), color former -1 ceric sulfate -10%
sulfuric acid solution spray], R4 about 0. R5 and Rf approximately 0.3
Soya saponin A appears in each of 0.

Each fraction containing Soya saponin A and Soya saponin A was separated. The solvent of each fraction was removed under reduced pressure, and each residue was
The suspension was suspended in 100% water, and lf cation exchange resin (Dowex 56wxg) was added thereto, followed by thorough stirring. The suspension was clear and dissolved. The respective filtered aqueous solutions were evaporated to dryness under reduced pressure to obtain white powders of Soya Saponin At1.9F and Soya Saponin A81.2F.

Each product was purified by recrystallization from aqueous methanol.

Production Example 4 Soybean seed powder 2:00 was heat-extracted twice with 20% n-hexane and defatted, and the defatted dried product was prepared from 207:98.
The mixture was added to methanol and extracted by heating under boiling twice for 3 hours each. This extract was subjected to vacuum distillation to obtain a 160F extract. This extract was mixed with n-butanol:water (1:1).
It was dissolved in 20 g of a mixed solution, distributed, and left to stand. The n-butanol transfer portion was separated and the solvent was distilled off under reduced pressure. The resulting residue (50F) was dissolved in 98 liters of methanol and added little by little to 20 J of ethyl ether. The resulting precipitate was filtered (35F) and subjected to silica gel column chromatography [Merck's Silica Gel G (707230 mesh), the elution solvent was chloroformimethanol-water (65F).
: 35 : 10 lower layer)] and treated with activated carbon to obtain total soya saponin 12F. This was further subjected to centrifugal liquid chromatography (using IT gel, soo rp
m), Soya saponin IC2, S2f! >, Soya Saponin If (0,45P), Soya Saponin N
(0,21P), Soya saponin A1 (0,40F
) and soya saponin^ (0,48F) were isolated, respectively.

Next, the results of an antitumor pharmacological test using a powder of soybean saponin component produced in the same manner as in Production Example 1 will be shown.

Test method: Leibovitz's L-15 culture medium and RAM'5-FIQ medium were mixed in a ratio of 7:3, with the added concentration of fetal bovine serum adjusted in advance so that the cell proliferation rate was 50 μl. Add soybean saponin component to the mixed culture solution at 1ay/sz, 5
Voice f//l, lOμ9/d, and protection/- were added to the cells at respective concentrations, and 1X10' Morris liver cancer cells and 5XIO' Lewis lung cancer cells were transplanted to each. Separately, the same number of each cancer cell was added to a culture solution to which soybean saponin was not added to form a control group. These culture solutions were plated at 36℃ for 4 days (5 plates each), and the number of proliferated cancer cells in the control group and the number of proliferated cancer cells in the soybean saponin-added group were compared to determine whether cancer cell proliferation was inhibited by each concentration of soybean saponin. The ratio was calculated using the following formula.

Cancer cell proliferation inhibition rate 1) - ((average number of cancer cells in control group after culture - average number of cancer cells in soybean saponin added group after culture)/(average number of cancer cells in control after culture - cancer in control group at the start of culture) Cell count))X100b) Test results After 4 days of culture, the average number of cancer cells in the control group was 1x10 at the start of culture for Morris liver cancer cells, but increased to 0.54x10' for Lewis lung cancer cells, and 5x10 for Lewis lung cancer cells. 'The average number is 2.9X
It grew to 10''.

From the average number of cancer cells after culture for this control group and the average number of cells after culture for the soybean saponin-added group, the cancer cell growth inhibition rate (regret) of soybean saponin was calculated from the above calculation formula. The results are shown in Table 1.

Table 1 Cancer cell proliferation inhibition rate (%) of soybean saponin As shown above,
At a concentration of 2 opP/yd, the saponin component of the soybean of this invention exhibited a remarkable cancer cell proliferation suppressing effect of 66 ml against Morris liver cancer cells and 52 ml against Lewis lung cancer cells.

Test Method The effect of soybean saponin obtained in Production Example 1 on methylcholanthrene meat 11 (hereinafter abbreviated as Meth-A) was examined based on its survival effect. BALM weighing 18-222
A group of 20/C strain mice (male) was implanted with lXl0' Meth-A cells intraperitoneally, and from the next day, the mice were challenged with 0.85% saline and 0.00% soybean saponin.
Support soybean with 1 scoop of dissolved solution once a day NOW/Yf
Continuous intrathecal injections were administered at a ratio of .

Separately, 1X10' Meth-A cells were intraperitoneally transplanted, and from the next day, only o, s s % physiological saline (0.2af) was administered every day as a control group.

b) Test results The results are shown in Table 2. After inoculation with Meth-A cells, the survival rate of the 20 mice in the control group was 50% on day 11.
On the other hand, in the soybean saponin-administered group, all mice survived on the 18th day and the survival rate was xoooo, and the survival rate on the 21st day was 55. Met. All mice died on the 27th day. As described above, soybean saponin clearly has a survival effect on transplanted cancers and can be said to have an antitumor effect.

The anti-tumor effect of the soybean saponin component of the present invention is explained by clinical examples in Table 2: Mouse survival rate test results after inoculation of Meth-A cells. Clinical Example 1 Patients: 0 to 100 patients were administered tablets containing 5 osy of soybean saponin components obtained in the same manner as in Production Example 1 and using lactose as an excipient. A, 55-year-old male office worker Family history: Nothing special Past medical history: Nothing special Current medical history: One year ago, the patient had chest pain, bloody sputum, and fever, and was diagnosed with lung cancer by X-ray diagnosis. Even after treatment with mitomycin C, cyclophosphamite, and chromomycin As, the general weakness did not significantly improve, so we switched to soybean saponin administration.

At this point, the red blood cell count was 3,400,700, and the white blood cell count was 1,080.
The patient's erythrocyte sedimentation rate was 42 per hour. An X-ray revealed a mass-like shape on his chest, and his skin was dull due to malnutrition (his entire body was weak).

Treatment progress: Soybean saponin 200"# was administered twice daily in the morning and evening. After one month, the pain in the chest disappeared, and after three months, the cough, fever, and bloody sputum all disappeared, and the red blood cell count decreased. 3,600,000,000,000 1, white blood cell count was 9.100/s♂, 1-hour erythrocyte sedimentation rate was 22, and no mass-like shape was observed on chest X-ray.The patient continued to take the same dose, and after 1 year. Currently, the number of red blood cells is 3,700,000/1, and the number of white blood cells is 8,000/I♂.
The 1-hour erythrocyte sedimentation rate was 1 G, and no recurrence was observed on chest X-ray, and the patient was progressing very well.

Clinical Case 2 Patient: T, 353 years old, female, housewife, housewife Family history: Nothing special Past medical history: # History of present illness: Part of the stomach was removed 2 years ago due to gastric cancer. One year ago, the patient had a feeling of abdominal distension and frequent nausea, and three months ago, ascites appeared, and he visited the hospital again and again. The left supraclavicular fossa and left axillary fossa felt heavy, and a mass the size of an index finger head and a red bean hole was palpable. red blood cell count 2
300,000^1, white blood cell count 3300/■1, erythrocyte sedimentation rate 1 hour value 34.2 hour value 46, and no shine was observed on the skin.

Treatment progress: After continuous administration of Soybean Su'bone 20G'IP twice a day, ascites decreased, abdominal bulge was no longer observed, and red blood cell count was 2807J/ws after 1 month.
``White blood cell count 4500/m'' improvement gtL? =. Five months later, the ascites had completely disappeared, the mass had become small enough to be felt by palpation, and the red blood cell count was 3907J/
m'', white blood cell count 6,400/m'', erythrocyte sedimentation rate 1
The time value was 16.2 and the time value was 33. He is currently continuing to take the drug and is doing very well.

Clinical case 3 Patient: S0M. 49-year-old male office worker Family history: Nothing special Past medical history: # Current history = One month ago, he had pain and discomfort in the right hypochondrium and was diagnosed with liver cancer.Recently, he has been feeling sluggish, has no appetite, and is gradually losing weight. It's here. At the time of the initial examination, the patient was malnourished, the skin was yellow due to yellow scars, and the liver was palpable to about 3 finger widths wide, with a hard and uneven surface, and 3 toga fingertip-sized masses were palpable. . Ascites was also observed. Red blood cell count is 2.2 million/■1, white blood cell count is 110,007 wa, blood sedimentation is 50 m (1 hour value), platelet count is 50,000/m, urinary bilirubin is (→, fecal occult blood anti-15 is (+), GOT /G"4i5
．． 0% A/G is 0.50. g-fetoprotein is 2
It was 00071P/dj.

In addition, a shadow defect was observed on liver scintigram.

Treatment progress: Soybean saponin component AOOQ was administered orally twice a day in divided doses. One month after administration, the general malaise and anorexia were improved, the jaundice disappeared, the swelling of the liver became as wide as a finger's width, the tumor size decreased, and ascites decreased. Red blood cell count is 30
07j/m", white blood cell count 110007m", blood sedimentation 3
5m (1 hour value), platelet count 81200/m'', urinary bilirubin disappeared, fecal occult blood reaction (→, GOT/m).
GPT is 4.0. A/G was improved to 0.8, and α-fetoprotein was improved to 150xp/d4.

Six months later, all subjective and objective symptoms disappeared, and although slight swelling in the lateral fingertip of the liver was palpable, the surface unevenness disappeared and the mass could not be palpated. Also, the ascites completely disappeared. Red blood cell count was 4,500,041, white blood cell count was 7,900/m'', and blood sedimentation was 2.
2 kana (1 hour value), platelet count 150,000/kaku 1, GOT/
Gpr was 1.5, A/G was 1.2, and α-fetoprotein was significantly improved to 1000 βP/d.

Since then, oral administration has been continued, and the patient is progressing very well.

Agent Patent Attorney Shinta Nogawa 1

Claims (1)

[Claims] 1. An antitumor agent comprising a soybean saponin component and a pharmaceutically acceptable excipient. 2. The saponin component of soybeans has the following properties: 1. It is a yellowish-white to brown powder with a slightly bitter taste and is odorless. It is easily soluble in methanol and diluted methanol, soluble in water and ethanol, chloroform, ether, hexane, Slightly soluble in carbon tetrachloride, 0.1 water attack solution is neutral, 'no 1 Infrared absorption 11L: j/ma+j (X di: i-le) 340
0 (br), 3a50(bsu, 1720(br) and 171O(br)aI-111L: y(KBr)
340G (br), 3350 (bsu, 2918.173
4 (btsu, 1385 (br), 1074 edict and 102
7cx. 2. Thin layer chromatography carrier Nibrate Kieselgel 60 F 254 (Merck & Co.) Developing solvent: Chloroform/methanol/water (6:4:1
) When x% ceric sulfate - 10% sulfuric acid mixture is sprayed and heated, distinct autumn leaf-colored saponin spots appear; (e) By acid hydrolysis, glucuronic acid, galactose, glucose, arabinose, rhamnose,
Kyjirose was obtained, and the main genin form, Soyasapogenol A (C--04, melting point 310-31) was extracted from the water-insoluble part.
2°C), Soyasapogenol B (CseHsoOn,
Melting point 260-261℃) was obtained, and there was no mold! Sawyer sapogenol C% D, Et - positive for Hellie-Berman reaction, Zarkowski reaction, T, When added to water and shaken, persistent small bubbles are generated. represents the formula (1): (wherein, R1 is α-L-rhamnopyranosyl (l → 2)-
β-〇-galactopyranosyl (l→2)-β-〇-glucuronopyranosyl group, α-L-rhamnopyranosyl (l→
2)-α-L-arabinopyranosyl (1→2)-β-D
-Glucuronopyranosyl group or β-D-galactopyranosyl (l→2)-β-D-glucuronopyranosyl group. or in the formula order (wherein - is β-D-groupyranosyl (1→2)-β
-D-galactopyranosyl (1→2)-β-〇-glucuronopyranosyl group, -β-D-glucopyranosyl (1-=3)-α-L-arabinopyranosyl group ,
or R1 is β-〇-galactopyranosyl-(1→2)
-β-〇-glucuronopyranosyl group, - represents β-D-glucopyranosyl (1→3)-α-L-arabinopyranosyl group) Patent containing at least one compound represented by The antitumor agent according to claim 1.