KR101280586B1 - Steviol or isosteviol derivatives and compositions for promoting animal and plant growth containing the same - Google Patents

Abstract

The present invention is a derivative of steviol and isosteviol, or a pharmaceutically acceptable salt thereof, a composition for promoting animal and plant growth containing them as an active ingredient, a method for promoting animal and plant growth using the composition and the composition It relates to a plant fertilizer and animal feed containing.

Description

Steviol or isosteviol derivatives and composition for promoting animal and plant growth containing same {Steviol or isosteviol derivatives and compositions for promoting animal and plant growth containing the same}

The present invention is a derivative of steviol and isosteviol, or a pharmaceutically acceptable salt thereof, a composition for promoting animal and plant growth containing them as an active ingredient, a method for promoting animal and plant growth using the composition and the composition It relates to a plant fertilizer and animal feed containing.

 6'carbamate esters of zealalanol (Korean Patent No. 128342) for promoting ruminant growth, and amide-based compound derivatives (Korean Patent No. 699404) are known as growth hormone secretion accelerators in animals. N-alkyl-N-acylamine derivatives (N-acylalanine derivatives) (Korean Patent No. 041827), which are plant growth promoters, are known to exhibit very excellent effects when used as fungicides for the protection of crops. It has excellent effects when used in cereals, rice, vegetables, sugar cane, soybeans, peanuts, fruit trees, hops, cucumbers (cucumbers, pumpkins, melons), eggplants (potatoes, tobacco, tomatoes), bananas, cocoa, etc. N-alkyl-N-acylamine derivatives are known in each country, but the yield is relatively low, and indirectly improves plant growth by preventing germ infection with excellent sterilizing power, rather than directly promoting plant growth. It is just to have an effect.

In addition, a solution containing two or more indoleacetic acid, gibberellin, benzylaminopurine, indolebutyric acid, etc., has been used as an agent for promoting the growth of plants. As alcohol must be used, there have been various problems such as alcohol penetrating into the plant and generating heat to wither the plant.

Growth regulators of animals and plants themselves undergo a series of processes that allow them to grow steadily under adverse conditions. These growth regulators stimulate growth hormone secretion, immune enhancement, cell division, seed germination, protein and RNA synthesis, chloroplast photosynthesis, and aging of flowers, fruits and leaves to inhibit protein and nucleus-related enzymes. Through it.

The present invention has been made in view of the above requirements, and the present invention has been derived to solve various problems of animal and plant growth promoters, which have been used in the prior art, and promotes the growth of animals and plants without side effects to harvest agricultural and livestock products. It is to develop a new compound that can increase.

In order to solve the above problems, the present invention provides a steviol derivative or a pharmaceutically acceptable salt thereof.

The present invention also provides isosteviol derivatives or pharmaceutically acceptable salts thereof.

The present invention also provides a composition for promoting animal and plant growth, containing the steviol derivative or a pharmaceutically acceptable salt thereof as an active ingredient.

The present invention also provides a method for promoting animal and plant growth, comprising the step of administering or treating the animal or plant growth promoting composition to a target animal or plant.

In addition, the present invention provides a plant fertilizer comprising the composition for promoting plant growth.

In addition, the present invention provides an animal feed comprising the composition for promoting animal growth.

The novel animal and plant growth promoting composition comprising a steviol or isosteviol derivative of the present invention can be applied to animals and plants in general, including vertebrates and tube plants. The composition has remarkable effects in promoting the growth of animals and plants, suppressing physiological disorders, alleviating serial disturbances, improving disease resistance, suppressing the occurrence of pests, increasing yields, improving color and maintaining freshness. It is also non-toxic and does not accumulate in organisms or pollute the soil environment.

1 shows the chemical structure of Dulcoside A extracted from stevia.
2 shows the chemical structure of Dulcoside B extracted from stevia.
3 shows the chemical structure of isosteviol extracted from stevia.
Figure 4 shows the chemical structure of Janol (Jhanol) extracted from stevia.
5 shows the chemical structure of Rebaudioside A extracted from Stevia.
Figure 6 shows the chemical structure of Rebaudioside B extracted from stevia.
7 shows the chemical structure of Rebaudioside D extracted from stevia.
8 shows the chemical structure of Rebaudioside E extracted from Stevia.
9 shows the chemical structure of Steviol extracted from Stevia.
10 shows the chemical structure of Steviolbioside extracted from Stevia.
11 shows the chemical structure of Steviolmonoside extracted from Stevia.
12 shows the chemical structure of Stevioside extracted from Stevia.
Figure 13 shows the chemical structure of stevioside sweetener (Stevioside sweetener) extracted from stevia.
Figure 14 shows the chemical structure of Steviol (Steviol).
Figure 15 shows the three-dimensional chemical structure of Steviol (Steviol).
Figure 16 shows the chemical structure of the Steviol salt.
17 shows the chemical structure of a steviol derivative.
Figure 18 shows the chemical structures of iso steviol, isosteviol salts and isostebiol derivatives.
19 shows the growth of soybeans.
20 shows the growth of corn.

In order to achieve the object of the present invention, the present invention provides a steviol derivative represented by the formula (1) or a pharmaceutically acceptable salt thereof:

[Wherein R and R 'are each

, 수소, C_{1 - 4}알킬, 1족 원소 또는 2족 원소이다.]

, Hydrogen, C _{1 - 4} is alkyl, 1 element or a Group 2 element.

, 수소 외에, 알킬기, 바람직하게는 C_{1 - 4}알킬기, 더욱 바람직하게는 메틸기 또는 에틸기일 수 있으나, 이에 제한되지 않는다. 또한, 상기 R 및 R'는 원소주기율표상의 1족 또는 2족 원소, 바람직하게는 나트륨, 칼륨 또는 칼슘일 수 있으나, 이에 제한되지 않는다.R and R 'are respectively

, In addition to hydrogen, an alkyl group, preferably a C _{1 - 4} alkyl group, but more preferably a methyl or ethyl group, but it is not limited thereto. In addition, the R and R 'may be a Group 1 or Group 2 element, preferably sodium, potassium or calcium on the periodic table, but is not limited thereto.

On the other hand, steviol derivatives or pharmaceutically acceptable salts thereof according to the present invention may include optically active carbon, in which case isomers may be present. Accordingly, the present invention may include cis or trans isomers of Formula 1 or mixtures of these isomers, which may exist in stereochemical form.

The present invention also provides an isostebiol derivative represented by Formula 2 or a pharmaceutically acceptable salt thereof:

[Wherein R is

, 수소, C_{1 - 4}알킬, 1족 원소 또는 2족 원소이다.]

, Hydrogen, C _{1 - 4} is alkyl, 1 element or a Group 2 element.

, 수소 외에, 알킬기, 바람직하게는 C_{1 - 4}알킬기, 더욱 바람직하게는 메틸기 또는 에틸기일 수 있으나, 이에 제한되지 않는다. 또한, 상기 R은 원소주기율표상의 1족 또는 2족 원소, 바람직하게는 나트륨, 칼륨 또는 칼슘일 수 있으나, 이에 제한되지 않는다.Wherein R is

, In addition to hydrogen, an alkyl group, preferably a C _{1 - 4} alkyl group, but more preferably a methyl or ethyl group, but it is not limited thereto. In addition, the R may be a Group 1 or Group 2 element, preferably sodium, potassium or calcium on the periodic table, but is not limited thereto.

On the other hand, isostevibiol derivatives or pharmaceutically acceptable salts thereof according to the present invention may include optically activated carbon, in which case isomers may be present. Accordingly, the present invention may include cis or trans isomers of Formula 2 or mixtures of these isomers, which may exist in stereochemical form.

In the present invention, the steviol may be prepared using a known prior art or commercially available and commercially available, and may also be extracted from stevia using a known prior art method, but It is not limited.

The present invention also provides a composition for promoting animal and plant growth, containing the steviol derivative or isostevibi derivative or pharmaceutically acceptable salt thereof as an active ingredient.

The composition for promoting animal and plant growth is not particularly limited in addition to containing the steviol derivative or isostevibiol derivative or pharmaceutically acceptable salt thereof as essential components in the indicated ratio. The active ingredient concentration of each salt or derivative of steviol or isosteviol in the composition may be 0.0001% (w / v) to 0.1% (w / v), preferably 0.001% (w / v) to 0.01 % (w / v), but is not limited thereto.

In the composition for promoting animal and plant growth, the animal may be preferably a vertebrate, but is not limited thereto, and the plant may be a tube plant, but is not limited thereto.

The plant growth promoting composition may be used in the form of an aqueous solution to facilitate the spraying of plants, but is not limited thereto.

The present invention also provides a method for promoting animal and plant growth, comprising the step of administering or treating the animal or plant growth promoting composition to a target animal or plant.

The method for promoting plant growth of the present invention includes treating the plant with a composition for promoting plant growth comprising any one or more selected from salts or derivatives of steviol or isosteviol in plant cultivation. The composition for promoting growth of a plant of the present invention may vary the period of treatment to the plant according to the type of plant. The treatment may be applied to plant seedlings, leaves, roots or soil around the roots, but is not limited thereto. The spraying may be applied before or after the application of the fertilizer or pesticide to the plant, or with the fertilizer or pesticide, but is not limited thereto. Preferably, after germinating the seed of the plant, the composition of the present invention having a concentration of 0.0001 to 0.1% for 1 to 3 weeks in seedlings grown for 1 to 3 weeks. Can be processed 2-4 times. More preferably, the composition of the present invention at a concentration of 0.001% to 0.01% by treatment for 2 weeks in seedlings grown for 2 weeks after germinating soybean or corn for 2 weeks Can be processed three times.

The method for promoting animal growth of the present invention includes feeding a composition for promoting growth of an animal comprising any one or more selected from the salts or derivatives of steviol or isosteviol in animal breeding. The salary may be oral administration, but is not limited thereto. The benefit may be, but is not limited to, before or after feeding the animal with the conventional feed or with the conventional feed.

The composition for promoting growth of an animal of the present invention may vary the period of feeding to the animal according to the type of animal. Preferably the animal can be fed the composition (0.01% to 1% aqueous solution) of the present invention from 0.005 ml / day to 0.5 ml / day per head of the animal. More preferably, the composition of the present invention (0.1% aqueous solution) from pigs to pigs (60 to 88 days of age: 28 days) and from the growth stage to sheds (from 147 to 182 days of age: 35 days) to 0.05 ml / pig of pig. You can pay by day.

In addition, the present invention provides a plant fertilizer comprising the composition for promoting plant growth. The plant fertilizer may include any one or more selected from salts or derivatives of steviol or isosteviol of the present invention.

Plant fertilizer comprising a composition for promoting plant growth of the present invention for promoting plant growth comprising any one or more selected from salts or derivatives of steviol or isosteviol of the present invention with respect to 100% (w / v) of conventional fertilizers The composition may comprise 0.0001% (w / v) to 0.1% (w / v), preferably 0.001% (w / v) to 0.01% (w / v), but is not limited thereto. The conventional fertilizers may be used inorganic or organic fertilizers commonly used in plant cultivation, preferably those containing nitrogen, phosphoric acid and potassium, more preferably nitrogen, phosphoric acid, potassium, minerals and trace elements As the plant cultivation can be used conventionally, but is not limited thereto. The inorganic material may be any one or more selected from calcium, magnesium, sulfur, iron, and the trace element may be any one or more selected from manganese, copper, zinc, boron, and molybdenum. In the cultivation of plants, the purpose of spraying fertilizers is to spray or inject nutrients necessary for plant growth and production into soil or plants. ), A phosphoric acid component (e.g., phosphorus pentoxide), a potassium component (e.g., potassium oxide), an inorganic substance (e.g., calcium, magnesium, sulfur, iron) and a trace element (e.g., manganese, copper, Zinc, boron, molybdenum), but is not limited thereto.

Plant fertilizer of the present invention can vary the period of treatment to the plant according to the type of plant.

In addition, the present invention provides an animal feed comprising the composition for promoting animal growth. The animal feed may include any one or more selected from salts or derivatives of steviol or isosteviol of the present invention.

Animal feed comprising the animal growth promoting composition of the present invention for promoting animal growth comprising any one or more selected from salts or derivatives of steviol or isosteviol of the present invention with respect to conventional feed 100% (w / v) The composition may comprise 0.0001% (w / v) to 0.1% (w / v), preferably 0.001% (w / v) to 0.01% (w / v), but is not limited thereto. The conventional feed is not only known in the art as a feed to be fed according to the kind of breeding animal, etc. Anyone skilled in the art can manufacture or purchase it very easily. Specifically, the conventional feed includes a part or all of starch-containing material, protein-containing material, fat-containing material, vitamin-containing material, mineral-containing material, antioxidant material, antibiotics, etc., which are suitable according to the breeding animal as a component of the feed. It is configured to include.

The starch-containing material may be used in the animal feed of the present invention as long as it can sustain the growth of the breeding animal, and such starch-containing material is generally obtained from corn, soybean, wheat, sorghum, barley, oats and the like. Suitable starch-containing materials include corn grits or powders, oat grits or powders, soy grits or powders, wheat grits or powders and the like. Preferred starch containing materials are oat powder, corn grind, wheat grind, soy flour and the like.

If the starch-containing material can effectively maintain the growth of the breeding animal, the concentration contained in the animal feed of the present invention is not limited to a specific range. In general, starch-containing materials may be included in the animal feed of the present invention in the range of about 30 to about 80 weight percent, preferably about 40 to about 70 weight percent, most preferably 50 to 70 weight percent.

Protein-containing substances may also be included in the animal feed of the present invention as long as it can maintain the growth of the animal. For economic reasons, protein-containing substances such as fish meal and soybean powder are used. Others include soy protein concentrate, blood meal, plasma protein, skim milk dry matter, milk protein concentrate, corn gluten powder, wheat. Gluten powder, yeast, sunflower seed powder, and the like. Preferred protein-containing substances are fish meal, blood meal, plasma protein, soybean powder and the like.

The concentration contained in the animal feed of the present invention is not important as long as the protein-containing substance can effectively maintain the growth of the animal. Generally, the protein containing material may be included in the feed composition of the present invention in the range of about 10 to about 50% by weight, preferably about 15 to about 40% by weight, most preferably 18 to 30% by weight.

Animal feed of the present invention may also include a fat-containing material. Suitable fat-containing materials include, but are not limited to, lard, tallow, soybean oil, lecithin, coconut oil, and the like. Preferred fat-containing materials are soybean oil, coconut oil and lard.

The concentration contained in the animal feed of the present invention is not important as long as the fat-containing substance can maintain the growth of the breeding animal. Fat-containing materials may generally be included in the animal feed of the present invention in the range of about 2 to about 20 weight percent, preferably about 4 to about 15 weight percent, most preferably 6 to 12 weight percent.

The animal feed composition of the present invention may also contain water-soluble and fat-soluble vitamins and trace minerals. Suitable vitamins include vitamin A, vitamin D, vitamin E, vitamin K, riboflavin, pantothenic acid, niacin, vitamin B12, folic acid, biotin and vitamin C. Suitable trace minerals include copper, zinc, iodine, selenium, manganese, iron, cobalt and the like.

A trace amount in the present invention means that the amount of these components used in the composition is substantially less than the amount of other components. Generally, when trace amounts of vitamins or minerals are included in the animal feed of the present invention, they are present from about 0.0001 to about 5 weight percent based on the total weight of the composition.

Animal feed of the present invention may also contain traces of antioxidants such as BHT (Butylated Hydroxytoluene), BHA (Butylated Hydroxyanisole), vitamin E, ascorbic acid, and also antibiotics such as chlorotetracycline, sulfamethazine and penicillin. May be included. These antioxidants or antibiotics are preferably included in the feed composition of the present invention in very small amounts, ie from about 0.0001 to about 1% by weight.

Animal feed of the present invention may vary the period of feeding to the animal according to the type of animal. In the present invention, when the pig was fed the composition of the present invention with feed for a certain period, it was confirmed that the weight or weight gain of the pig is increased. Therefore, the growth promoting composition may be specifically understood as an animal feed composition for increasing weight or weight gain. In the present invention, the weight gain means the degree of increase in the weight of the animal for a predetermined period, and the increase in weight means that the degree of increase in the weight of the animal is increased for a predetermined period.

Animals and plants according to the present invention may be, but not limited to, vertebrates and tubular plants, preferably vegetable, poultry and fish in the field of animals, fruit vegetables, grains, flowers and grass in the field of plants. Most preferably pigs in the animal field, soybeans or corn in the plant field.

Hereinafter, the present invention will be described in detail by way of examples. However, the following examples are illustrative of the present invention, and the present invention is not limited to the following examples.

Example  One

Using a round bottom flask, dissolve 2 g of Steviol-glucoside (Figures 1-13) in 30.0 mL of liquid buffer (citrate or phosphate) and add 0.2 g of Pancreatin. Toluene (10 mL) or ethanol (50 mL) was added thereto, followed by reaction for 7 days, and then the mixture was extracted with ethyl acetate and butanol. Both ethyl acetate and butanol extract were dried to obtain the steviol derivative 4 of FIG. 17 as a powder.

<Molecular Formula> C ₂₀ H ₃₀ O ₃

<Molecular weight> 318.45

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.89 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 4.95 (1H, brs, vinylic ), 5.52 (1H, brs, vinylic)

< 13C- NMR > (C5D5N, 25 MHz) δ: 41.1 (C1), 19.8 (C2), 38.6 (C3), 43.9 (C4), 57.1 (C5), 22.6 (C6), 41.8 (C7), 41.8 ( C8), 54.3 (C9), 39.8 (C10), 20.8 (C11), 40.7 (C12), 79.8 (C13), 47.4 (C14), 48.1 (C15), 157.6 (C16), 102.9 (C17), 29.3 ( C18), 180.0 (C19), 15.9 (C20)

<Mass analysis> MS: M + = 318

Example  2

dried Stevia rebaudiana Bertoni) 100 kg of leaves or leaves and stems were placed in 100 L of purified water, and extracted with hot water at 90-100 ° C. for 10 hours, and then the used filtrate was concentrated to 50-60 briquettes after removing the used stevia leaves or leaves and stems. 500 g of the stevia extract concentrate was dissolved in 2N HCl, and reacted by applying heat at 90 ° C. for 90 minutes. The reaction was cooled and centrifuged at 3,000 rpm for 3 minutes to obtain a precipitate. The precipitate was washed with purified water twice or more to obtain isosteviol 1 (Iso steviol 1) of FIG. 18 as a powder.

<Molecular Formula> C ₂₀ H ₃₀ O ₃

<Molecular weight> 318.45

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.89 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 2.17 (1H, d, vinylic ), 2.66 (1H, d, vinylic)

< 13C- NMR > (C5D5N, 25 MHz) δ: 40.0 (C1), 19.2 (C2), 37.3 (C3), 43.6 (C4), 57.0 (C5), 21.9 (C6), 41.6 (C7), 48.7 ( C8), 54.7 (C9), 38.2 (C10), 20.3 (C11), 38.2 (C12), 39.5 (C13), 54.3 (C14), 48.6 (C15), 222.7 (C16), 19.9 (C17), 29.3 ( C18), 180.5 (C19), 13.5 (C20)

<Mass analysis> MS: M + = 318

Example  3

0.5 g of steviol glycosides (Figs. 1-13) are dissolved in 2N HCl and reacted by heating at 90 ° C for 90 minutes. The reaction was cooled and centrifuged for 3 minutes at 3,000 rpm to obtain a precipitate. After washing the precipitate with purified water two or more times, the powder of isosteviol 1 of FIG. 18 was obtained.

<Molecular Formula> C ₂₀ H ₃₀ O ₃

<Molecular weight> 318.45

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.89 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 2.17 (1H, d, vinylic ), 2.66 (1H, d, vinylic)

< 13C- NMR > (C5D5N, 25 MHz) δ: 40.0 (C1), 19.2 (C2), 37.3 (C3), 43.6 (C4), 57.0 (C5), 21.9 (C6), 41.6 (C7), 48.7 ( C8), 54.7 (C9), 38.2 (C10), 20.3 (C11), 38.2 (C12), 39.5 (C13), 54.3 (C14), 48.6 (C15), 222.7 (C16), 19.9 (C17), 29.3 ( C18), 180.5 (C19), 13.5 (C20)

<Mass analysis> MS: M + = 318

Example  4

10 g of isostebiol 1 of FIG. 18 was added to 100 mL of purified water, and the aqueous NaOH solution was slowly dropped to pH 8.5 while stirring at room temperature, followed by stirring for 2 hours. The reaction solution was completely removed by using a rotary vacuum evaporator to obtain the isostebiol salt 2 of FIG. 18, which is in the form of a powder having excellent solubility in water.

<Molecular Formula> C ₂₀ H ₂₉ O ₃ Na

<Molecular weight> 340.43

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.89 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 2.17 (1H, d, vinylic ), 2.66 (1H, d, vinylic)

< 13C- NMR > (C5D5N, 25 MHz) δ: 40.0 (C1), 19.2 (C2), 37.3 (C3), 43.6 (C4), 57.0 (C5), 21.9 (C6), 41.6 (C7), 48.7 ( C8), 54.7 (C9), 38.2 (C10), 20.3 (C11), 38.2 (C12), 39.5 (C13), 54.3 (C14), 48.6 (C15), 222.7 (C16), 19.9 (C17), 29.3 ( C18), 180.5 (C19), 13.5 (C20)

<Mass analysis> MS: M-Na = 318

Example  5

10 g of isosteviol 1 of FIG. 18 was added to 100 mL of purified water, and stirred at room temperature, KOH aqueous solution was slowly dropped to pH 8.5, followed by stirring for 2 hours. The reaction solution was completely removed using a rotary vacuum evaporator to obtain the isostebiol salt 3 of FIG. 18 in the form of a powder having excellent solubility in water.

<Molecular formula> C ₂₀ H ₂₉ O ₃ K

<Molecular weight> 356.54

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.89 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 2.17 (1H, d, vinylic ), 2.66 (1H, d, vinylic)

< 13C- NMR > (C5D5N, 25 MHz) δ: 40.0 (C1), 19.2 (C2), 37.3 (C3), 43.6 (C4), 57.0 (C5), 21.9 (C6), 41.6 (C7), 48.7 ( C8), 54.7 (C9), 38.2 (C10), 20.3 (C11), 38.2 (C12), 39.5 (C13), 54.3 (C14), 48.6 (C15), 222.7 (C16), 19.9 (C17), 29.3 ( C18), 180.5 (C19), 13.5 (C20)

<Mass analysis> MS: MK = 318

Example  6

After dissolving 10 g of isosteviol 1 in FIG. 18 in 70% ethanol, 10 g of CaO was added thereto, followed by heating with stirring. After stirring for 1 hour at reflux, the precipitate formed by cooling to room temperature was filtered, washed with cold 70% ethanol, and dried at room temperature or reduced pressure to obtain isosteviol salt 4 of FIG. 18.

<Molecular Formula> C ₂₀ H ₂₉ O ₃ Ca

<Molecular weight> 357.52

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.89 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 2.17 (1H, d, vinylic ), 2.66 (1H, d, vinylic)

< 13C- NMR > (C5D5N, 25 MHz) δ: 40.0 (C1), 19.2 (C2), 37.3 (C3), 43.6 (C4), 57.0 (C5), 21.9 (C6), 41.6 (C7), 48.7 ( C8), 54.7 (C9), 38.2 (C10), 20.3 (C11), 38.2 (C12), 39.5 (C13), 54.3 (C14), 48.6 (C15), 222.7 (C16), 19.9 (C17), 29.3 ( C18), 180.5 (C19), 13.5 (C20)

<Mass Spectrometry> MS: M-Ca = 318

Example  7

10 g of isosteviol 1 in FIG. 18 was dissolved in diethyl ether, and an excess amount of CH ₂ N ₂ was added thereto, followed by stirring for 12 hours or more. The mixture was dried using a rotary evaporator. The dried mixture was separated by column chromatography to obtain isostebiol derivative 5 of FIG. 18.

<Molecular Formula> C ₂₁ H ₃₂ O ₃

<Molecular weight> 332.24

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.89 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 2.17 (1H, d, vinylic ), 2.66 (1H, d, vinylic)

<13C- NMR > (CD ₃ OD, 150 MHz) δ 13.5, 19.2, 19.9, 20,3, 21.9, 29.3, 37.3, 38.2, 38.3, 39.6, 40.0, 41.6, 43.6, 48.6, 48.7, 54.3, 54.7, 57.0,74.9, 180.5, 222.6

<Mass analysis> MS: M + = 331

Example  8

Isosteviol 1 (0.2 g, 0.6 mmol), 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-hexynylbenzoate (2,3,4,6-tetra of FIG. 18) -O-benzoyl-D-glucopyranosyl ortho-hexynylbenzoate) (0.5 g, 0.63 mmol), DBU (1,8-diazabicyclo [5.4.0] undec-7-ene, 0.19 mL, 1.2 mmol) was added to dichloromethane. Dissolved in 10 ml, 4 Å (0.5 g) of activated molecular sieves was added and stirred at room temperature. BF ₃ OEt ₂ (0.2 mL, 1.8 mmol) was slowly added to the mixture, followed by adding PPh ₃ AuOTf (0.05 M, 0.5 mL) dissolved in dichloromethane. After stirring at room temperature for 18 hours or more, the mixture was filtered and the filtrate was concentrated under reduced pressure and dried. The mixture was subjected to column chromatography to obtain benzoyl glucoside coupled isostebiol derivative 6.

<Molecular Formula> C ₂₆ H ₄₀ O ₈

<Molecular weight> 480.5910

<1H- NMR > (DMSO-d ₆ , 600 MHz) δ 0.85 (3H, s), 0.86 (3H, m), 0.97 (3H, s), 1.05 (1H, m), 1.11 (1H, m), 1.21 (3H, s), 1.42 (1H, m), 1.48 (1H, m), 1.50 (2H, m), 1.60 (1H, m), 1.62 (1H, m), 1.66 (2H, m), 1.67 (1H, m), 1.71 (3H, s), 1.83 (1H, m), 1.84 (1H, m), 1.96 (1H, m), 2.13 (1H, d, 12), 2.22 (1H, d, 9 ), 3.143.18 (2H, m), 3.28 (1H, dd, 8), 3.46 (1H, dd, 2, 8), 4.09 (1H, d, 7), 4.23 (1H, dd, 2, 12) , 4.96 (1H, s), 5.32 (1H, d, 8), 5.51 (1H, s).

<13C- NMR > (DMSO-d ₆ , 150 MHz) δ 15.1, 19.0, 20.4, 21.8, 28.8, 36.1, 37.8, 39.5, 40.7, 41.5, 42.5, 43.6, 44.1, 47.2, 53.6, 56.9, 62.6 71.3, 77.7, 77.9, 84.1, 85.8, 97.1, 103.1, 153.8, 182.3.

<Mass analysis> MS: M + = 480

Example  9

0.5 g of steviol glycosides (Figs. 1 to 13) were added to 0.75 g sodium periodate / 50 mL DW and reacted at room temperature for 20 hours, and then 3.75 g of NaOH was added to the reaction and refluxed for 2 hours. The mixture was cooled on ice for 40 minutes and then slowly administered with glacial acetic acid to pH 5.5. The precipitate obtained after centrifugation or purification was extracted three times with 150 mL of ethyl acetate, and the organic layer was washed with water three times. After drying with 3 g of sodium sulfate, it was filtered and dried using a rotary evaporator to obtain a powder (Fig. 14). The powder was adjusted to pH 8.6 with NaOH to obtain steviol salts 1, 2 and 3 of FIG.

<Molecular Formula> C ₂₀ H ₂₈ Na ₂ O ₃ (1), C ₂₀ H ₂₉ NaO ₃ (2), C ₂₀ H ₂₉ NaO ₃ (3)

<Molecular weight> 362.42 (1), 341.43 (2), 341.43 (3)

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.89 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 2.17 (1H, d, vinylic ), 2.66 (1H, d, vinylic)

< 13C- NMR > (C5D5N, 25 MHz) δ: 40.0 (C1), 19.2 (C2), 37.3 (C3), 43.6 (C4), 57.0 (C5), 21.9 (C6), 41.6 (C7), 48.7 ( C8), 54.7 (C9), 38.2 (C10), 20.3 (C11), 38.2 (C12), 39.5 (C13), 54.3 (C14), 48.6 (C15), 222.7 (C16), 19.9 (C17), 29.3 ( C18), 180.5 (C19), 13.5 (C20)

<Mass analysis> MS: M-Na = 318

Example  10

0.5 g of steviol glycosides (Figs. 1 to 13) were added to 0.75 g sodium periodate / 50 mL DW and reacted at room temperature for 20 hours, followed by refluxing with 3.75 g of KOH. The mixture was cooled in ice for 40 minutes, and then slowly added glacial acetic acid to pH 5.5. The precipitate obtained after centrifugation or purification was extracted three times with 150 mL of ethyl acetate and the organic layer was washed with water three times. After drying with 3 g of sodium sulfate, it was filtered and dried using a rotary evaporator to obtain a powder (Fig. 14). The powder was adjusted to pH 8.6 using KOH to obtain steviol salts 4, 5 and 6 of FIG.

<Molecular Formula> C ₂₀ H ₂₈ K ₂ O ₃ (4), C ₂₀ H ₂₉ KO ₃ (5), C ₂₀ H ₂₉ KO ₃ (6)

<Molecular weight> 396.64 (4), 357.54 (5), 357.54 (6)

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.89 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 2.17 (1H, d, vinylic ), 2.66 (1H, d, vinylic)

< 13C- NMR > (C5D5N, 25 MHz) δ: 40.0 (C1), 19.2 (C2), 37.3 (C3), 43.6 (C4), 57.0 (C5), 21.9 (C6), 41.6 (C7), 48.7 ( C8), 54.7 (C9), 38.2 (C10), 20.3 (C11), 38.2 (C12), 39.5 (C13), 54.3 (C14), 48.6 (C15), 222.7 (C16), 19.9 (C17), 29.3 ( C18), 180.5 (C19), 13.5 (C20)

<Mass analysis> MS: MK = 318

Example  11

0.5 g of steviol glycosides (FIGS. 1-13) were dissolved in 70% ethanol, and 0.7 g of CaO was added thereto, followed by heating with stirring. After stirring for about 1 hour, the resultant precipitate was cooled to room temperature, filtered, washed with cold 70% ethanol, and dried at room temperature or reduced pressure to obtain steviol salt 7, 8, and 9 of FIG.

<Molecular Formula> C ₂₀ H ₂₈ Ca ₂ O ₃ (7), C ₂₀ H ₂₉ CaO ₃ (8), C ₂₀ H ₂₉ CaO ₃ (9)

Molecular weight 396.59 (7), 357.52 (8), 357.52 (9)

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.89 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 2.17 (1H, d, vinylic ), 2.66 (1H, d, vinylic)

< 13C- NMR > (C5D5N, 25 MHz) δ: 40.0 (C1), 19.2 (C2), 37.3 (C3), 43.6 (C4), 57.0 (C5), 21.9 (C6), 41.6 (C7), 48.7 ( C8), 54.7 (C9), 38.2 (C10), 20.3 (C11), 38.2 (C12), 39.5 (C13), 54.3 (C14), 48.6 (C15), 222.7 (C16), 19.9 (C17), 29.3 ( C18), 180.5 (C19), 13.5 (C20)

<Mass Spectrometry> MS: M-Ca = 318

Example  12

Steviol (derivative 4, 0.1 g) was dissolved in diethyl ether, and excess CH ₂ N ₂ was added and stirred for at least 12 hours. The mixture was dried using a rotary evaporator. The dried mixture was separated by column chromatography to obtain derivatives 5, 6 and 7 of FIG.

Derivative 5

<Molecular Formula> C ₂₁ H ₃₂ O ₃

<Molecular weight> 332.4770

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.89 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 4.95 (1H, brs, vinylic ), 5.52 (1H, brs, vinylic)

<13C- NMR > (CD ₃ OD, 150 MHz) δ 15.2, 19.0, 20.5, 21.8, 28.8, 37.8, 38.1, 39.5, 40.6, 41.3, 41.7, 43.6, 46.5, 47.0, 53.8, 55.3, 56.9, 74.9, 103.0, 155.9, 182.3.

<Mass analysis> MS: M + = 331

Derivative 6

<Molecular Formula> C ₂₁ H ₃₂ O ₃

<Molecular weight> 332.4770

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.91 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 2.20 (3H, s, OAc ), 4.95 (1H, brs, vinylic), 5.51 (1H, brs, vinylic)

<13C- NMR > (CD ₃ OD, 150 MHz) δ 15.5, 19.1, 20.5, 21.8, 28.8, 37.8, 39.3, 39.5, 40.6, 41.3, 41.7, 43.6, 47.0, 47.4, 53.8, 56.9, 75.1, 80.4, 103.0, 155.9, 182.3.

<Mass analysis> MS: M + = 331

Derivative 7

<Molecular Formula> C ₂₂ H ₃₄ O ₃

<Molecular weight> 346.5

<1H- NMR > (CD3OD, 600 MHz) δ: 0.77 (2H, s), 0.89 (3H, s), 0.93-2.15 (20H, m), 1.19 (3H, s), 3.42 (3H, s), 4.51 (3H, s) 4.95 (1H, brs, vinylic), 5.52 (1H, brs, vinylic)

<13C- NMR > (CD ₃ OD, 150 MHz) δ 15.4, 19.0, 21.5, 21.9, 28.7, 37.5, 39.3, 39.2, 40.5, 41.2, 41.5, 43.4, 47.1, 47.4, 52.5, 56.9, 74.8, 80.4, 81.3, 103.5, 154.9, 182.1.

<Mass analysis> MS: M + = 346

Example  13

Steviol (1.0 g, 3.1 mmol) was dissolved in dichlororomethane, and 3 ((1.0 g) of molecular sieves activated at 350 ° C. were added and stirred at room temperature for 30 minutes. After 30 minutes, HgO (3.4 g, 15.5 mmol) / HgBr ₂ (1.7 g, 4.7 mmol) was added and bromo acethoxyglucopyranose (1.9 g, 4.7 mmol) was added thereto for 18 hours at room temperature. Stirred. The reaction mixture was filtered through a celite bed and washed twice with dichloromethane. The filtrate was washed with 30% KI, saturated NaHCO ₃ and then with distilled water, dried over MgSO ₄ and dried under reduced pressure. The reaction mixture was purified by column chromatography to obtain acetoxyglucopyranose coupled steviol derivative 1. Acetyl glucopyranose is dissolved in 30 ml MeOH / H ₂ O / THF (5/2/1, v / v) mixed solution, and 30 ml of 0.1N LiOH / H ₂ O solution is added at 0 ° C. After addition it was stirred for 2 hours. After 2 hours, 1.5 g of amberlite cation exchange resin was added to the reaction mixture, mixed well, and the cation exchange resin was filtered off. MeOH and THF were removed by concentration under reduced pressure, and the aqueous solution was purified by reverse phase column chromatography to obtain Steviol Derivative 1 of FIG.

Derivative 1

<Molecular Formula> C ₂₆ H ₃₉ O ₈

<Molecular weight> 479.58

<1H- NMR > (DMSO-d ₆ , 600 MHz) δ 0.85 (3H, m), 0.86 (3H, m), 0.97 (3H, s), 1.05 (1H, m), 1.11 (1H, m), 1.21 (3H, s), 1.42 (1H, m), 1.48 (1H, m), 1.50 (2H, m), 1.60 (1H, m), 1.62 (1H, m), 1.66 (2H, m), 1.67 (1H, m), 1.71 (3H, s), 1.83 (1H, m), 1.84 (1H, m), 1.96 (1H, m), 2.13 (1H, d, 12), 2.22 (1H, d, 9 ), 3.27 (1H, m), 3.35 (1H, m), 3.38 (2H, m), 3.46 (1H, m,), 3.61 (1H, m), 4.64 (1H, d, 8), 4.80 (1H , d, 8), 4.95 (1H, s), 5.12 (1H, s), 5.52 (1H, s).

<13C- NMR > (DMSO-d ₆ , 150 MHz) δ 15.1, 19.0, 20.4, 21.8, 28.8, 36.1, 37.8, 39.5, 40.7, 41.5, 42.5, 43.6, 44.1, 47.2, 53.6, 56.9, 62.6 71.3, 77.7, 77.9, 84.1, 85.8, 97.1, 103.1, 153.8, 182.3.

<Mass analysis> MS: M + = 480

Example  14

Steviol (0.2 g, 0.6 mmol), or steviol derivative 1 (0.6 mmol) and 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-hexynylbenzoate (2,3, 4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-hexynylbenzoate) (0.5 g, 0.63 mmol), DBU (1,8-diazabicyclo [5.4.0] undec-7-ene, 0.19 mL, 1.2 mmol) It was dissolved in dichloromethane (10 mL), and 4 Å (0.5 g) of activated molecular sieve was added and stirred at room temperature. BF ₃ OEt ₂ (0.2 mL, 1.8 mmol) was slowly added to the mixture, followed by PPh ₃ AuOTf (0.05 M, 0.5 mL) dissolved in dichloromethane. After stirring at room temperature for 18 hours or more, the mixture was filtered, and the filtrate was concentrated under reduced pressure and dried. The mixture was column chromatographed to obtain benzoyl glucoside coupled steviol derivatives 2 or 3. The benzoyl group was removed through hydrogenation to obtain derivatives 2 or 3 of FIG. 17.

Derivative 2

<Molecular Formula> C ₂₆ H ₃₉ O ₈

<Molecular weight> 479.58

<1H- NMR > (DMSO-d ₆ , 600 MHz) δ 0.85 (3H, s), 0.86 (3H, m), 0.97 (3H, s), 1.05 (1H, m), 1.11 (1H, m), 1.21 (3H, s), 1.42 (1H, m), 1.48 (1H, m), 1.50 (2H, m), 1.60 (1H, m), 1.62 (1H, m), 1.66 (2H, m), 1.67 (1H, m), 1.71 (3H, s), 1.83 (1H, m), 1.84 (1H, m), 1.96 (1H, m), 2.13 (1H, d, 12), 2.22 (1H, d, 9 ), 3.143.18 (2H, m), 3.28 (1H, dd, 8), 3.46 (1H, dd, 2, 8), 4.09 (1H, d, 7), 4.23 (1H, dd, 2, 12) , 4.96 (1H, s), 5.32 (1H, d, 8), 5.51 (1H, s).

<13C- NMR > (DMSO-d ₆ , 150 MHz) δ 15.1, 19.0, 20.4, 21.8, 28.8, 36.1, 37.8, 39.5, 40.7, 41.5, 42.5, 43.6, 44.1, 47.2, 53.6, 56.9, 62.6 71.3, 77.7, 77.9, 84.1, 85.8, 97.1, 103.1, 153.8, 182.3.

<Mass analysis> MS: M + = 480

Derivative 3

<Molecular Formula> C ₃₂ H ₅₀ O ₁₃

<Molecular weight> 642.7316

<1H- NMR > (DMSO-d ₆ , 600 MHz) δ 0.85 (3H, m), 0.86 (3H, m), 0.97 (3H, s), 1.05 (1H, m), 1.11 (1H, m), 1.21 (3H, s), 1.42 (1H, m), 1.48 (1H, m), 1.50 (2H, m), 1.60 (1H, m), 1.62 (1H, m), 1.66 (2H, m), 1.67 (1H, m), 1.71 (3H, s), 1.83 (1H, m), 1.84 (1H, m), 1.96 (1H, m), 2.13 (1H, d, 12), 2.22 (1H, d, 9 ), 3.05 (1H, t, 8), 3.153.19 (2H, m), 3.26-3.31 (3H, m), 3.38 (1H, t, 8), 3.46 (1H, dd, 2, 8), 3.99 (1H, d, 12), 4.09 (1H, d, 7), 4.25 (2H, m), 4.47 (1H, d, 8), 4.96 (1H, s), 5.31 (1H, d, 8), 5.51 (1H, s).

<13C- NMR > (DMSO-d ₆ , 150 MHz) δ 15.1, 19.0, 20.4, 21.8, 28.1, 36.1, 38.1, 39.6, 40.7, 41.5, 42.5, 44.1, 47.2, 53.6, 57.2, 61.8, 62.6, 70.4 , 71.3, 73.2, 74.1, 77.7, 77.9, 78.0, 78.3, 85.8, 94.9, 97.1, 153.8, 104.2, 176.8.

<Mass analysis> MS: M + = 642

Example  15

In order to test the effects of plant growth using the results of the present invention, growth experiments were conducted on soybeans and corn as representative crops. In the present invention, the growth conditions of the crops were compared after three treatments for two weeks using the representative compounds of FIGS. 16 to 18.

-Experimental materials: 1. Soybean 10 plates (36 objects / plate), Corn 10 plates (36 objects / plate)

              -Seedlings grown 2 weeks after germination

             2. 0.01-0.001% solution of compounds of FIGS. 16-18

Experimental method: The seedlings grown for 2 weeks after germinating soybeans and corn were treated with the compounds of the present invention (specified in FIGS. 16 to 18) for 2 weeks. After three treatments, growth-related items were examined.

-Measurement items: height, leaf length, leaf width, fresh weight

Compounds used to test the effects of animal and plant growth compound Processing times The number of processing objects Control (no treatment) 2 36 Steviol Salt 1 / Fig 16 2 36 Steviol Salt 4 / Fig 16 2 36 Steviol Salt 7 / Fig 16 2 36 Steviol derivative 4 / Fig 17 2 36 Steviol derivative 2 / Fig 17 2 36 Steviol Salt 3 / Figure 16 2 36 Steviol salt 6/16 2 36 Steviol Salt 9 / Fig 16 2 36 Steviol derivative 3 / Fig 17 2 36 Steviol derivative 5 / Fig 17 2 36 Steviol derivative 7 / Fig 17 2 36 Isosteviol 1 / Fig. 18 2 36 Isosteviol salt 2 / Fig 18 2 36 Isosteviol salt 3 / Fig. 18 2 36 Isosteviol salt 4 / Fig 18 2 36 Isostebiol derivative 5 / Fig. 18 2 36 Isostebiol derivative 6 / Figure 18 2 36

Soybean Growth Treatment Compound (0.01-0.001%) Total treatment Population Extra long (cm) Gross weight (g) Total dry weight (g) Control (no treatment) 72 98 508 86 Steviol Derivatives 4 72 102 518 90 Steviol Derivatives 2 72 100 512 88 Steviol salt 1 72 112 521 93 Steviol Salt 7 72 118 525 95 Steviol Salt 4 72 125 537 102 Steviol salt 3 72 113 522 89 Steviol Salt 6 72 126 538 103 Steviol Salt 9 72 119 526 96 Steviol Derivatives 3 72 102 512 89 Steviol Derivatives 5 72 105 520 90 Steviol Derivatives 7 72 104 521 91 Isosteviol 1 72 103 518 90 Isosteviol salt 2 72 110 519 91 Isosteviol salt 3 72 123 535 100 Isosteviol salt 4 72 116 523 93 Isosteviol Derivatives 5 72 106 519 89 Isosteviol Derivatives 6 72 101 511 87

Growth of Corn Treatment Compound (0.01-0.001%) Total treatment Population Extra long (cm) Gross weight (g) Total dry weight (g) Control (no treatment) 72 120 842 180 Steviol Derivatives 4 72 131 848 183 Steviol Derivatives 2 72 126 843 180 Steviol salt 1 72 142 851 186 Steviol Salt 7 72 146 853 189 Steviol Salt 4 72 152 862 190 Steviol salt 3 72 143 852 187 Steviol Salt 6 72 153 863 191 Steviol Salt 9 72 147 854 190 Steviol Derivatives 3 72 126 844 181 Steviol Derivatives 5 72 129 846 188 Steviol Derivatives 7 72 128 845 184 Isosteviol 1 72 130 837 182 Isosteviol salt 2 72 140 849 184 Isosteviol salt 3 72 150 860 188 Isosteviol salt 4 72 144 851 187 Isosteviol Derivatives 5 72 130 847 186 Isosteviol Derivatives 6 72 125 843 180

Example  16

In order to test the growth-related effects of animals using the results of the present invention, growth experiments were conducted on pigs as representative animals. In this experiment, each compound (0.1% aqueous solution) was used from the piglet section (60 to 88 days of age: 28 days) and the growth period (147 to 182 days of age: 35 days) using the representative compounds of FIGS. Were compared after growth of 0.05 ml / day per pig.

Daily gain in piglets (60-88 days of age: 28 days) Treatment compound Treatment head Final weight (kg) / weight gain (kg) Throughput (two / day, 0.1% solution) Control group 100 33.4 No treatment Steviol Salt 7 100 37.2 / + 3.8 0.05 ml Steviol salt 1 100 36.8 / + 3.4 0.05 ml Steviol Salt 4 100 36.5 / + 3.1 0.05 ml Steviol Derivatives 4 100 36.3 / + 2.9 0.05 ml Steviol Derivatives 2 100 35.9 / + 2.5 0.05 ml Steviol salt 3 100 36.9 / + 3.2 0.05 ml Steviol Salt 6 100 36.6 / + 2.8 0.05 ml Steviol Salt 9 100 37.0 / + 3.3 0.05 ml Steviol Derivatives 3 100 35.6 / + 2.9 0.05 ml Steviol Derivatives 5 100 35.2 / + 3.3 0.05 ml Steviol Derivatives 7 100 35.4 / + 2.5 0.05 ml Isosteviol 1 100 36.4 / + 2.5 0.05 ml Isosteviol salt 2 100 36.2 / + 3.2 0.05 ml Isosteviol salt 3 100 35.9 / + 3.1 0.05 ml Isosteviol salt 4 100 36.8 / + 3.6 0.05 ml Isosteviol Derivatives 5 100 35.5 / + 3.1 0.05 ml Isosteviol Derivatives 6 100 35.7 / + 2.7 0.05 ml

Daily weight gain from growing period (147 ~ 182 days old: 35 days) Treatment compound Treatment head Final weight (kg) / weight gain (kg) Throughput (two / day, 0.1% solution) Control group 100 112.3 No treatment Steviol Salt 7 100 116.5 / + 4.2 0.05 ml Steviol salt 1 100 115.4 / + 3.1 0.05 ml Steviol Salt 4 100 115.2 / + 2.9 0.05 ml Steviol Derivatives 4 100 115.0 / + 2.7 0.05 ml Steviol Derivatives 2 100 115.1 / + 2.9 0.05 ml Steviol salt 3 100 115.5 / + 2.8 0.05 ml Steviol Salt 6 100 115.3 / + 3.3 0.05 ml Steviol Salt 9 100 116.6 / + 3.9 0.05 ml Steviol Derivatives 3 100 115.1 / + 2.8 0.05 ml Steviol Derivatives 5 100 115.1 / + 2.7 0.05 ml Steviol Derivatives 7 100 114.9 / + 3.4 0.05 ml Isosteviol 1 100 114.9 / + 3.1 0.05 ml Isosteviol salt 2 100 114.9 / + 3.3 0.05 ml Isosteviol salt 3 100 114.6 / + 3.0 0.05 ml Isosteviol salt 4 100 115.8 / + 4.0 0.05 ml Isosteviol Derivatives 5 100 115.3 / + 2.7 0.05 ml Isosteviol Derivatives 6 100 115.0 / + 2.5 0.05 ml

Claims (11)

delete delete delete delete A steviol derivative represented by the following formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient, composition for promoting animal growth.
[Formula 1]

[Wherein R and R 'are each

, Hydrogen, C _1-4 alkyl, group 1 element or group 2 element.] An isostebiol derivative represented by the following formula (2) or a pharmaceutically acceptable salt thereof as an active ingredient, animal growth promoting composition.
(2)

[Wherein R is

, Hydrogen, C _1-4 alkyl, group 1 element or group 2 element.] The method according to claim 5 or 6, wherein the active ingredient concentration of each of the salt or derivative of steviol or isosteviol is promoted animal growth, characterized in that 0.0001% (w / v) to 0.1% (w / v) Composition. The composition for promoting animal growth according to claim 5 or 6, wherein the animal is a vertebrate. An animal growth promoting method comprising the step of administering or treating the animal growth promoting composition of claim 5 or claim 6 to a subject animal. delete Animal feed comprising the composition for promoting animal growth of claim 5 or 6.

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