Composition for enhancing physiological activity comprising ieodomycin compound

Abstract

A composition for enhancing physiological activity of the present invention comprises, as an active ingredient, ieodomycin, stereoisomers thereof, or a synthetic derivative thereof, and has at least one activity selected from the group consisting of whitening, moisturizing, anti-diabetes, and anti-hypertension.

Description

Composition for enhancing physiological activity comprising an erodomycin compound

[0001] Various embodiments of the present invention relate to a composition for enhancing physiological activity comprising an eodomycin compound. Specifically, the present invention relates to a composition for enhancing physiological activity comprising eodomycin, a stereoisomer thereof, or a synthetic derivative thereof as an active ingredient.

[0002] Marine organisms possess a rich biodiversity, which leads to chemical diversity. Therefore, marine organisms can serve as an excellent resource for new drug discovery. To date, considerable effort has been made to identify bioactive secondary metabolites with novel chemical structures and biological functions from marine organisms. In this regard, total synthetic methods are being developed to overcome the problem of material supply, a major challenge facing drug discovery from marine organisms.

[0003] Ieodomycin is known to exhibit broad antibacterial activity against Bacillus subtilis (KCTC 1021, Gram-negative), Escherichia coli (KCTC 1923, Gram-positive), and Saccharomyces cerevisiae (KCTC 7913, yeast). However, other biological activities have not yet been discovered. The present inventors have confirmed various physiological activities of eodomycin, its stereoisomers, and synthetic derivatives, thereby completing the present invention.

[0004] The purpose of the present invention is to provide a composition for enhancing physiological activity, which comprises Ieodomycin, its stereoisomers or its synthetic derivatives having various physiological activities as an active ingredient.

[0005] The composition for enhancing physiological activity of the present invention comprises Ieodomycin, stereoisomers thereof, or synthetic derivatives thereof as an active ingredient.

[0006] The composition for enhancing physiological activity of the present invention comprises ieodomycin, a stereoisomer thereof, or a synthetic derivative thereof as an active ingredient, and has at least one activity selected from the group consisting of whitening, moisturizing, antidiabetic, and antihypertensive activities. The present invention can synthesize ieodomycin, a stereoisomer thereof, or a synthetic derivative thereof in high yield and use it as an active ingredient.

[0007] Specifically, the composition for enhancing physiological activity of the present invention has excellent tyrosinase inhibition efficacy. The composition for enhancing physiological activity of the present invention has excellent hyaluronidase inhibition efficacy. The composition for enhancing physiological activity of the present invention has excellent α-glucosidase inhibition efficacy. The composition for enhancing physiological activity of the present invention has excellent ACE inhibition efficacy.

[0008] Figure 1 shows the results of a tyrosinase inhibition efficacy experiment.

[0009] Figure 2 shows the results of a hyaluronidase inhibition efficacy experiment.

[0010] Figure 3 shows the results of confirming cell viability in HDF cells for the compound of the example.

[0011] Figure 4 shows the results of confirming the procollagen content (PIP production) in HDF cells for the compound of the example.

[0012] Figure 5 shows the results of an α-glucosidase inhibition efficacy experiment.

[0013] Figures 6 and 7 show the results of an α-glucosidase inhibitory efficacy test for some of the compounds of the examples.

[0014] Figure 8 shows the results of an ACE inhibition efficacy experiment.

[0015] Hereinafter, various embodiments of this document are described with reference to the attached drawings. The embodiments and terminology used herein are not intended to limit the technology described in this document to specific embodiments, but should be understood to encompass various modifications, equivalents, and / or alternatives of the embodiments.

[0016]

[0017] The composition for enhancing physiological activity of the present invention comprises Ieodomycin, stereoisomers thereof, or synthetic derivatives thereof as an active ingredient.

[0018] Specifically, Ieodomycin may be (+)-Ieodomycin A represented by the following [chemical formula 1], or (+)-Ieodomycin B represented by the following [chemical formula 2].

[0019] [Chemical Formula 1]

[0020]

[0021] [Chemical Formula 2]

[0022]

[0023] Meanwhile, the stereoisomer may be a stereoisomer obtained from (+)-ieodomycin B. Specifically, the stereoisomer may be 3-epi-ieodomycin B represented by the following [chemical formula 3], 5-epi-ieodomycin B represented by the following [chemical formula 4], or (-)-ieodomycin B represented by the following [chemical formula 5].

[0024] [Chemical Formula 3]

[0025]

[0026] [Chemical Formula 4]

[0027]

[0028] [Chemical Formula 5]

[0029]

[0030] Meanwhile, the synthetic derivative may be a synthetic derivative obtained from (+)-ieodomycin B. Specifically, the synthetic derivative may be 3,5-epi-allyl-ieodomycin B represented by the following [chemical formula 6] or 3,5-epi-phenyl-ieodomycin B represented by the following [chemical formula 7].

[0031] [Chemical Formula 6]

[0032]

[0033] [Chemical Formula 7]

[0034]

[0035] Here, physiological activity may mean at least one activity selected from the group consisting of whitening, moisturizing, antidiabetic, and antihypertensive.

[0036] A whitening or moisturizing composition according to various embodiments of the present invention may include at least one compound selected from the group consisting of [Chemical Formula 1], [Chemical Formula 2], [Chemical Formula 3], [Chemical Formula 4], [Chemical Formula 6] and [Chemical Formula 7] as an active ingredient.

[0037] Specifically, the whitening composition according to various embodiments of the present invention may contain, as an active ingredient, at least one compound selected from the group consisting of [Chemical Formula 1], [Chemical Formula 2], [Chemical Formula 3], [Chemical Formula 4], and [Chemical Formula 6]. The compounds of [Chemical Formula 1], [Chemical Formula 2], [Chemical Formula 3], [Chemical Formula 4], and [Chemical Formula 6] may have excellent tyrosinase inhibitory efficacy. The whitening composition according to various embodiments of the present invention may be a cosmetic composition.

[0038] A moisturizing composition according to various embodiments of the present invention may include the compound of [Chemical Formula 7] as an active ingredient. The compound of [Chemical Formula 7] may have excellent hyaluronidase inhibitory efficacy. A moisturizing composition according to various embodiments of the present invention may be a cosmetic composition.

[0039] The cosmetic composition of the present invention may additionally contain one or more cosmetically acceptable additives. The one or more cosmetically acceptable additives are not particularly limited and may include conventional ingredients incorporated into general cosmetics, such as oil, water, surfactants, moisturizers, alcohols, thickeners, pigments, preservatives, fragrances, chelating agents, excipients, diluents, sunscreens, fatty acids, and the like.

[0040] The cosmetic composition of the present invention may be, without particular limitation, any one formulation selected from the group consisting of skin, lotion, cream, gel, essence, foundation, toner, patch, pack, soap, cleanser, and detergent.

[0041]

[0042] An antidiabetic or antihypertensive composition according to various embodiments of the present invention may include at least one compound selected from the group consisting of [Chemical Formula 3], [Chemical Formula 4], [Chemical Formula 5], and [Chemical Formula 6] as an active ingredient.

[0043] Specifically, the antidiabetic composition according to various embodiments of the present invention may include, as an active ingredient, at least one compound selected from the group consisting of [Chemical Formula 3] and [Chemical Formula 4]. The compounds of [Chemical Formula 3] and [Chemical Formula 4] may have excellent α-glucosidase inhibitory efficacy. The antidiabetic composition according to various embodiments of the present invention may be a pharmaceutical composition and / or food composition having excellent effects of improving, preventing, or treating diabetes.

[0044] The antihypertensive composition according to various embodiments of the present invention may include, as an active ingredient, at least one compound selected from the group consisting of [Chemical Formula 3], [Chemical Formula 5], and [Chemical Formula 6]. The compounds of [Chemical Formula 3], [Chemical Formula 5], and [Chemical Formula 6] may have excellent ACE inhibitory efficacy. The antihypertensive composition according to various embodiments of the present invention may be a pharmaceutical composition and / or food composition having excellent effects of improving, preventing, or treating hypertension.

[0045] The pharmaceutical composition of the present invention may include a pharmaceutically acceptable carrier. The composition including the pharmaceutically acceptable carrier may be in various oral or parenteral dosage forms. When formulated, it may be prepared using diluents or excipients such as commonly used fillers, bulking agents, binders, wetting agents, disintegrants, and surfactants. Solid preparations for oral administration include tablets, pills, powders, granules, capsules, etc., and such solid preparations may be prepared by mixing one or more compounds with at least one excipient, such as starch, calcium carbonate, sucrose, lactose, gelatin, etc. In addition to simple excipients, lubricants such as magnesium stearate and talc may also be used. Liquid preparations for oral administration include suspensions, solutions, emulsions, and syrups. In addition to commonly used simple diluents such as water and liquid paraffin, they may contain various excipients such as wetting agents, sweeteners, fragrances, and preservatives. Preparations for parenteral administration may include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, and suppositories. Non-aqueous solvents and suspensions may include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate.

[0046] The above pharmaceutical composition may have any one dosage form selected from the group consisting of tablets, pills, powders, granules, capsules, suspensions, solutions, emulsions, syrups, sterilized aqueous solutions, non-aqueous solutions, suspensions, emulsions, lyophilized preparations, and suppositories.

[0047] The pharmaceutical composition of the present invention may be administered in a pharmaceutically effective amount. As used herein, the term "pharmaceutically effective amount" means an amount sufficient to treat a disease at a reasonable benefit / risk ratio applicable to medical treatment, and the effective dosage level may be determined based on factors including the type and severity of the individual, age, sex, activity of the drug, sensitivity to the drug, time of administration, route of administration and excretion rate, duration of treatment, concurrently used drugs, and other factors well known in the medical field.

[0048] The food composition of the present invention may further contain one or more additives acceptable for drinking or food use. The one or more additives acceptable for drinking or food use are not particularly limited and may be conventional ingredients that can be incorporated into beverages or foods, such as water, flavoring agents, flavoring agents, coloring agents, stabilizers, preservatives, alcohol, carbonating agents, fruit pulp, thickeners, vitamins, plant extracts, organic acids, minerals, nutrients, etc.

[0049] The form of the food composition of the present invention is not particularly limited, but may be any form selected from the group consisting of beverages, gum, tea, confectionery, vitamin complexes, and health supplements.

[0050]

[0051] Hereinafter, the present invention will be described in detail through specific embodiments.

[0052] However, the following examples are only intended to illustrate the present invention, and the present invention is not limited by the following examples.

[0053]

[0054] <Example 1> Synthesis of (+)-Ieodomycin A and (+)-Ieodomycin B

[0055] As shown in the schematic diagrams below, (+)-Ieodomycin A and (+)-Ieodomycin B were synthesized. First, referring to Scheme 1, the synthesis was started using commercially available 4-pentyn-1-ol (5). 4-pentyn-1-ol (5) was converted to aldehyde (6) by Swern oxidation using oxalyl chloride in CH2Cl2, TEA, and DMSO at -78 °C. The resulting aldehyde (6) was subjected to Keck asymmetric allylation using (S)-BINOL to form homoallyl alcohol (7a) with 98% ee, and homoallyl alcohol (7b) with 98% ee was formed by the same conversion using (R)-BINOL. Next, the required cis configuration of the side chain was successfully formed through carboalumination modification of Wipf using ZrCl2Cp2 and Me3Al, followed by iodination. The resulting cisvinyl iodide moiety should remain dormant until a Stille cross-coupling reaction is performed to form the conjugated diene at the end of the synthesis. Consequently, vinyl iodides (8a and 8b) were obtained in 59% and 74% yields, respectively, in three steps from 4-pentyn-1-ol (5).

[0056]

[0057] <Schematic diagram 1>

[0058]

[0059] Sharpless asymmetric dihydroxylation reaction was performed using the two major intermediates obtained previously, vinyl iodides (8a and 8b).

[0060] Specifically, referring to the schematic diagram 2 below, conversion was attempted using modified cinchona alkaloid ligands, (DHQ)2PYR and (DHQD)2PYR.

[0061] More specifically, when treated with an AD mixture containing (DHQ)2PYR, 8a produced triols 9a and 9b in yields of 52% and 20% (dr = 2.6:1), respectively. In contrast, under AD reaction conditions using (DHQD)2PYR, triols 9a and 9b were produced in yields of 5% and 71% (dr = 1:14.2), respectively. In contrast, dehydroxylation of 8b using (DHQ)2PYR produced 9c and 9d in yields of 65% and 8% (dr = 8:1:1), respectively. In contrast, the reaction using (DHQD)2PYR produced 9c and 9d in yields of 13% and 66% (dr = 1:5.1), respectively.

[0062] <Schematic diagram 2>

[0063]

[0064] Next, a reaction as shown in schematic diagram 3 below was performed to form a lactone core and a conjugated diene side chain.

[0065] Specifically, 9a was converted to acetonide (13a) in a two-step process by sulfonylation with TPSCl to give the sulfonate (10a) in 98% yield, which was then protected with 2,2-dimethoxypropane (97% yield). Cyanation of the acetonide (13a) using NaCN gave the desired cyanide (14a) in 88% yield, which was subsequently deprotected to give the intermediate (15a) in 95% yield. Subsequently, basic hydrolysis of the cyanide (15a) gave the corresponding carboxylic acid (16a), which was then Mukaiyama lactonised with 2-chloro-methylpyridinium iodide without purification to give the lactone (17a) in two steps in 76% yield. To complete the synthesis, Stille cross-coupling of lactone (17a) was performed using tributyl(vinyl)tin and DIPEA in NMP in the presence of 10 mol% Pd2dba3 at room temperature to obtain (+)-iodomycin B(2) in 67% yield. In addition, the lactone ring of (+)-iodomycin B(2) was successfully opened using K2CO3 in MeOH to obtain (+)-iodomycin A(1) in 93% yield.

[0066] <Schematic diagram 3>

[0067]

[0068] <Example 2> Synthesis of stereoisomers

[0069] In the preceding Example 1, after successfully synthesizing (+)-erodomycin A and B, stereoisomers were synthesized.

[0070] Specifically, referring to the following schematic diagram 4, three stereoisomers of iedomycin B (18-20) were obtained following the same synthetic route used to obtain (+)-iedomycin B. Accordingly, intermediates (15b-15d) were prepared via sequential reactions including sulfonylation of triols (9b-9d) (77-98% yield), protection of diols (10b-10d) (94-98% yield), cyanation of sulfonates (13b-13d) (87-93% yield), and deprotection of acetonides (14b-14d) (94-98% yield). These intermediates were then subjected to two steps of basic hydrolysis followed by Mukaiyama lactonization to obtain the lactones (17b-17d) in 56-84% yield. Finally, the corresponding erudomycin B stereoisomers (18 to 20) were obtained in 64-93% yields through Stille cross-coupling reactions of 17b to 17d.

[0071] <Schematic diagram 4>

[0072]

[0073] Meanwhile, the synthesis of (+)-erodomycin A, (+)-erodomycin B and three stereoisomers described in Examples 1 and 2 is summarized in Scheme 5 below.

[0074] <Schematic Diagram 5>

[0075]

[0076] <Example 3> Synthesis of synthetic derivatives

[0077] Referring to the following schematic diagram 6, to lactone 17d ((4R,6S)-4-hydroxy-6-((E)-4-iodo-3-methylbut-3-en-1-yl)tetrahydro-2H-pyran-2-one) (32.0 mg, 0.1 mmol, 1.0 equiv) dissolved in NMP (0.1 M, 1 mL) were added allyltributylstannane (62 μL, 0.2 mmol, 2.0 equiv), Pd2dba3 (18.2 mg, 0.02 mmol, 0.2 equiv), and DIPEA (87.0 μL, 0.5 mmol, 5.0 equiv). The reaction was stirred at room temperature under N2 for 6 h. NH4Cl(aq.) was added to quench the reaction, and the mixture was extracted three times with ether. The organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The crude was purified by flash column chromatography to obtain the product ((4R,6S)-4-hydroxy-6-((E)-3-methylhepta-3,6-dien-1-yl)tetrahydro-2H-pyran-2-one) (5.5 mg, 0.024 mmol, 24%) of formula 6.

[0078] <Schematic diagram 6>

[0079]

[0080] Referring to the following schematic diagram 7, tributylphenylstannane (47.1 μL, 0.16 mmol, 2.0 equiv), Pd2dba3 (14.6 mg, 0.016 mmol, 0.2 equiv) and DIPEA (70.0 μL, 0.4 mmol, 5.0 equiv) were added to lactone 17d ((4R,6S)-4-hydroxy-6-((E)-4-iodo-3-methylbut-3-en-1-yl)tetrahydro-2H-pyran-2-one (24.4 mg, 0.08 mmol, 1.0 equiv) dissolved in NMP (0.1 M, 0.8 mL). The reaction was heated to 50 °C and stirred under N2 for 18 h. NH4Cl (aq.) was added to quench the reaction and the mixture The mixture was extracted three times with ether. The organic layer was dried over Na2SO4, filtered, and evaporated in vacuo. The crude was purified by flash column chromatography to obtain the product ((4R,6S)-4-hydroxy-6-((E)-3-methyl-4-phenylbut-3-en-1-yl)tetrahydro-2H-pyran-2-one) (4.7 mg, 0.018 mmol, 23%) of the chemical formula 7.

[0081] <Schematic diagram 7>

[0082]

[0083] <Experimental Example 1> Evaluation of whitening efficacy

[0084] The compounds synthesized through the above Examples 1 to 3 are as follows.

[0085] Example Name Chemical Formula Example 1 (+)-Ieodomycin A [Chemical Formula 1] (+)-Ieodomycin B [chemical formula 2] Example 23-epi-ieodomycin B [chemical formula 3] 5-epi-ieodomycin B [chemical formula 4] (-)-ieodomycin B [chemical formula 5] Example 33,5-epi-allyl-ieodomycin B [chemical formula 6] 3,5-epi-phenyl-ieodomycin B [chemical formula 7]

[0086] The whitening efficacy was evaluated using compounds of chemical formulas 1 to 7 according to Table 1 above. To confirm the whitening efficacy, a tyrosinase inhibition assay, a major enzyme involved in melanin biosynthesis, was performed.

[0087] Specifically, 110 μL of potassium phosphate buffer (0.1 M, pH 6.5) and 10 μL of tyrosinase (2,000 units / mL) in potassium phosphate buffer were mixed with 25, 50, 100, and 200 μM compounds of chemical formulas 1 to 7, respectively, in a 96-well plate. Then, 20 μL of L-tyrosine (1.5 mM) was added to the mixture and incubated at 37°C for 15 minutes. After incubation, the absorbance was measured at 490 nm using a Synergy HT microplate reader. As a positive control, 25, 50, 100, and 200 μM arbutin were prepared by treating in the same manner.

[0088]

[0089] Meanwhile, IC according to the treatment concentration of the sample 50 The values ​​are calculated and shown below in Figure 1.

[0090] Referring to Figure 1, the results of the tyrosinase inhibition efficacy experiment confirmed that the compounds of chemical formulas 1, 2, 3, 4, and 6 had enzyme inhibition efficacy similar to that of the positive control, Arbutin.

[0091] Therefore, it was confirmed that compounds of chemical formulas 1, 2, 3, 4 and 6 have whitening effects.

[0092] <Experimental Example 2> Evaluation of moisturizing efficacy

[0093] Hyaluronic acid, a component that provides moisture to the skin, is broken down by hyaluronidase, an enzyme synthesized in the body. Therefore, to confirm the moisturizing effect, hyaluronidase inhibition activity was evaluated.

[0094] Specifically, a solution containing hyaluronidase (8 mg / mL) and hyaluronic acid (2.4 mg / mL) dissolved in 0.1 M acetic acid buffer (pH 3.6) was prepared. 12.5 μL of compounds of formulae 1 to 7 and the hyaluronidase solution were mixed in an e-tube at 37°C for 20 minutes. 25 μL of calcium chloride (12.5 mM) was added and incubated at 37°C for another 20 minutes. Thereafter, 62.5 μL of hyaluronic acid was added to the mixture and incubated at 37°C for 40 minutes. After incubation, the reaction was stopped by adding 2.5 μL of sodium hydroxide (0.4 N) and 25 μL of potassium tetraborate (0.4 N), and incubated at 100°C for 3 minutes. Finally, the mixed solution was cooled to room temperature, treated with 750 μL of DMAB solution (4 g of DMAB in 35 mL of acetic acid and 5 mL of hydrochloric acid), and incubated at 37°C for 20 minutes. Each mixture was transferred to a 96-well plate, and the absorbance was measured at 585 nm using a Synergy HT microplate reader. EGCG (Epigallro Catechine Gallate) was prepared as a positive control using the same method.

[0095]

[0096] As a result, referring to Fig. 2, the hyaluronidase inhibition efficacy test results confirmed that the compound of chemical formula 7 had excellent enzyme inhibition efficacy.

[0097] In addition, referring to FIGS. 3 and 4, the procollagen content in HDF cells was confirmed for the compound of chemical formula 7, and as the concentration increased, the procollagen content increased, confirming the moisturizing effect.

[0098]

[0099] <Experimental Example 3> Evaluation of antidiabetic efficacy

[0100] The inhibitory effect of α-glucosidase, an enzyme related to antidiabetes, was confirmed.

[0101] Specifically, α-glucosidase inhibition was measured using an α-glucosidase inhibitor screening kit (Abcam, Cambridge, UK). Briefly, 10 μL of compounds of formulas 1 to 7 were mixed with 10 μL of α-glucosidase solution and 60 μL of assay buffer in a 96-well plate. After incubation at room temperature for 20 minutes in the dark, 20 μL of substrate solution was added to the wells. The absorbance at 410 nm was measured in kinetic mode for 60 minutes using a Synergy HT microplate reader. Acarbose served as the positive control.

[0102] As a result, referring to Figure 5, it was confirmed that the compounds of chemical formulas 3 and 4 specifically exhibited excellent α-glucosidase inhibition efficacy, and in particular, the compound of chemical formula 3 exhibited better efficacy than the positive control, Acarbose.

[0103] The α-glucosidase inhibitory efficacy of compounds of chemical formulae 3 and 4 was confirmed once again, and as a result, referring to Figure 6, it was confirmed that both compounds of chemical formulae 3 and 4 showed better efficacy than the positive control, Acarbose, at 0.25 mM or higher.

[0104] Referring to Figure 7, it was confirmed that the compound of chemical formula 3 had excellent α-glucosidase inhibitory efficacy as the concentration increased.

[0105] <Experimental Example 4> Evaluation of antihypertensive efficacy

[0106] Inactivated angiotensin I present in the body is converted into angiotensin II, which has a vascular wall constriction effect, by the cleavage of the C-terminal His-Leu by angiotensin I converting enzyme (ACE), which constricts blood vessels and increases the secretion of aldosterone in the kidney, thereby increasing body fluid volume and raising blood pressure. Therefore, by inhibiting the activity of ACE, blood pressure can be suppressed by reducing the production of angiotensin II, which is the cause of increased blood pressure. Therefore, the ACE inhibition effect was confirmed.

[0107] Specifically, ACE inhibition was measured colorimetrically using the ACE kit-WST (Dojindo Laboratories, Kumamoto, Japan), which measures the amount of 3-hydroxybutyric acid generated from 3-hydroxybutyryl-Gly-Gly-Gly by the enzyme. Substrate buffers were prepared with or without compounds of formulas 1 to 7 in a 96-well plate, and enzyme solutions were added to the wells. After incubation, indicator solutions were added to all wells. The amount of 3-hydroxybutyric acid was assessed by measuring the absorbance at 450 nm using a Synergy HT microplate reader.

[0108]

[0109] As a result, referring to Figure 8, the ACE inhibitory effect was confirmed in the compounds of chemical formulas 3, 5, and 6.

[0110]

[0111] The features, structures, effects, etc. described in the above-described embodiments are included in at least one embodiment of the present invention, and are not necessarily limited to just one embodiment. Furthermore, the features, structures, effects, etc. exemplified in each embodiment can be combined or modified in other embodiments by those skilled in the art to which the embodiments pertain. Therefore, the contents related to such combinations and modifications should be construed as falling within the scope of the present invention.

[0112] In addition, although the above description focuses on embodiments, these are merely examples and do not limit the present invention. Those skilled in the art to which the present invention pertains will appreciate that various modifications and applications not exemplified above are possible without departing from the essential characteristics of the present embodiments. For example, each component specifically shown in the embodiments can be modified and implemented. In addition, differences related to such modifications and applications should be interpreted as being included within the scope of the present invention defined in the appended claims.

[0113] The composition for enhancing physiological activity of the present invention contains Ieodomycin, its stereoisomers or its synthetic derivatives as an active ingredient, and has whitening, moisturizing, antidiabetic or antihypertensive activities, and thus can be used as a cosmetic composition, pharmaceutical composition or food composition.

Claims

1. A composition for enhancing physiological activity comprising iodomycin, its stereoisomers or its synthetic derivatives as an active ingredient.

2. In paragraph 1, The above edematous medicament is, A composition for enhancing physiological activity, characterized in that it is (+)-Ieodomycin A represented by the following [chemical formula 1] or (+)-Ieodomycin B represented by the following [chemical formula 2]. [Chemical Formula 1] [Chemical Formula 2] 3. In paragraph 1, The above stereoisomers are, A composition for enhancing physiological activity, characterized in that it is 3-epi-ieodomycin B represented by the following [chemical formula 3], 5-epi-ieodomycin B represented by the following [chemical formula 4], or (-)-ieodomycin B represented by the following [chemical formula 5]. [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] 4. In paragraph 1, Synthetic derivatives are, A composition for enhancing physiological activity, characterized in that it is 3,5-epi-allyl-ieodomycin B represented by the following [chemical formula 6] or 3,5-epi-phenyl-ieodomycin B represented by the following [chemical formula 7]. [Chemical Formula 6] [Chemical Formula 7] 5. In paragraph 1, A composition for enhancing physiological activity, characterized in that the physiological activity is at least one activity selected from the group consisting of whitening, moisturizing, antidiabetic, and antihypertensive.

6. A whitening or moisturizing composition comprising at least one compound selected from the group consisting of [Chemical Formula 1], [Chemical Formula 2], [Chemical Formula 3], [Chemical Formula 4], [Chemical Formula 6] and [Chemical Formula 7] as an active ingredient. [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] 7. An antidiabetic or antihypertensive composition comprising at least one compound selected from the group consisting of [chemical formula 3], [chemical formula 4], [chemical formula 5] and [chemical formula 6] as an active ingredient. [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6]

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