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(12) United States Patent (10) Patent No.: US 8,455,023 B2 Wang Et Al

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(12) United States Patent (10) Patent No.: US 8,455,023 B2 Wang Et Al USOO8455O23B2 (12) United States Patent (10) Patent No.: US 8,455,023 B2 Wang et al. (45) Date of Patent: Jun. 4, 2013 (54) COMPOSITION FOR INHIBITING (52) U.S. Cl. MELANOGENESIS AND USE THEREOF USPC .......................................................... 424/739 (58) Field of Classification Search (75) Inventors: Hui-Min Wang, Kaohsiung (TW); None Chung-Yi Chen, Kaohsiung (TW); Zhi-Hong Wen, Kaohsiung (TW) See application file for complete search history. (73) Assignee: Kaohsiung Medical University, (56) References Cited Kaohsiung (TW) PUBLICATIONS (*) Notice: Subject to any disclaimer, the term of this Lin et al. Bioactivity Investigation of Lauraceae Trees Grown in patent is extended or adjusted under 35 Taiwan. Pharmaceutical Biology. 2007 vol. 45, No. 8, pp. 638-644.* U.S.C. 154(b) by 126 days. Reader's Digest. The Healing Power of Vitamins, Minerals, and Herbs. Jan. 11, 1999. pp. 23-24.* (21) Appl. No.: 12/848,380 * cited by examiner (22) Filed: Aug. 2, 2010 Primary Examiner — Amy L. Clark (65) Prior Publication Data (74) Attorney, Agent, or Firm — WPAT, P.C.; Anthony King US 2011 FO212194A1 Sep. 1, 2011 (57) ABSTRACT (30) Foreign Application Priority Data The present invention provides a Cinnamomum subavenium extract for inhibiting melanogenesis. The present invention Feb. 26, 2010 (TW) ............................... 99.105580 A also provides a composition for inhibiting melanogenesis including compounds inhibit tyrosinase activity. (51) Int. Cl. A6 IK36/54 (2006.01) 4 Claims, 5 Drawing Sheets U.S. Patent Jun. 4, 2013 Sheet 1 of 5 US 8,455,023 B2 Figure Airdried stems of C. subavenium 8.0 kg ex 8ted extracts (202.5 g. {x}re, ticket recki. pess. 2. CCO CHCs 23.5 g) {{ 8.3: Fraction 7.46g Fraction 2 (9.3 g) 8:::::::33-x: interarcicie B 23 nig U.S. Patent Jun. 4, 2013 Sheet 2 of 5 US 8,455,023 B2 are 2A {?od?uodgo%}Á?j?qe?aHap suae -eae ?ž?mae Figure 28 (jouquo3go%)aseulsouÁL -ae •? u U.S. Patent Jun. 4, 2013 Sheet 3 of 5 US 8,455,023 B2 s Ë *3 •}% #(Ionuoo?oºquæquoouuelew -ae? -ae ew ? U.S. Patent Jun. 4, 2013 Sheet 4 of 5 US 8,455,023 B2 US 8,455,023 B2 1. 2 COMPOSITION FOR INHIBITING 5,968.487 provides a synthetic 5-hydroxy-4-oxo-4H-pyran MELANOGENESIS AND USE THEREOF 2-ylmethyl 2-oxothiazolidine-4-carboxylate to inhibit human melanin synthesis as skin whitening agent. U.S. Pat. No. FIELD OF THE INVENTION 6,750.229 provides a soybean extracted STI and Bowman Birk protease inhibitor, which Bowman-Birk protease inhibi The present invention is related to a Cinnamomum subave tor functions on upper epidermis showing significant melanin nium extract and use therefore. The Cinnamomum subave inhibition along with increasing concentration. The melanin nium extract can be applied in whitening cosmetology by inhibition reaches more than 40% when combining these two inhibiting melanogenesis. extracts on pigs. 10 As described above, there are several pharmaceuticals can BACKGROUND OF THE INVENTION be used for whitening cosmetic agents. However, applying these whitening cosmetic ingredients alone shows weak Skin melanin is produced by melanocytes which locate in effect. The product stability or safety issues such as skin stratum of epidermis. Human skin usually have similar level irritation are not satisfactory for market demand. For of melanocytes, however, different population may have 15 example, it is known that ascorbic acid is not stable and easy variation of melanin gene expression. Melanin is an insoluble to induce dermatitis. Kojic Acid and its derivatives have high molecular weight polymer with compact molecular strong whitening effect but are easy to degrade under light or structure, which binds to protein very often. Based on its heat exposure. Hydroquinone has strong whitening effect but structure, melanin can be grouped into eumelanins, low stability. It also has discoloring issues during cosmetic pheomelanins and allomelanins. Melanin in mammals is a production Such as micelle and lotion as well as issues of mixed population of eumelanins and pheomelanins in various inducing allergic contact dermatitis. Regarding biophama ratios. The quantities and types of these two kinds of melanin ceuticals such as Guang Dong Ginseng, it is too pricey to are controlled by 4 to 6 genes through incomplete dominant generate low cost whitening agent for regular consumers. inheritance. Each gene copy is derived from both parents who In Summary, there are still demands on compositions with express different skin colors after combination. 25 excellent whitening effect at low dose or compositions with Melanin synthesis requires several enzymes and molecules good safety and stability without skin irritation, and compo for biochemical reactions, such as tyrosine, tyrosinase and sitions easy to take or combine with food, cosmetics, and oxygen. Tyrosinase oxidizes tyrosine into dihydroxypheny pharmaceuticals. lalanine, transforms it to dopachrome, indoles, and finally melanin (Wulf, et al. Skin aging and natural photoprotection. 30 BRIEF DESCRIPTION OF THE DRAWINGS 2004 Micron, 35, 185-191). Rate limiting step of that reaction is the step that the catalyzing by tyrosinase from dihydrox FIG. 1 shows the flow chart of extraction and purification yphenylalanine into dopachrome. Auto-oxidation of dopach of two compounds—linderanolide B and subamolide A. rome produces melanin. Tyrosinase is a copper containing FIG. 2 shows the results of different concentrations of metal enzyme, which is synthesized by melanocytes. Tyrosi 35 linderanolide B and Subamolide A on human melanocyte. nase plays a very important role of melanin production. When Kojic acid, N-phenylthiourea and MSH are also included. tyrosinase activity increases, melanin production increases. FIG. 2A shows cell toxicity result, FIG. 2B shows tyrosinase On the contrary, when tyrosinase activity is inhibited, the activity results, and FIG. 2C shows percentage of human ability of melanocyte producing melanin drops accordingly. melanin content. Control group value is set as 100%. There are many reasons cause melanin precipitation. The 40 FIG. 3 shows the effect of different concentrations of lin elevation of tyrosinase activity leads to melanin synthesis deranolide B and subamolide A on cell growth. Microscopic when skin is exposed to UV radiation. Copper concentration images were taken under 200x magnification bright field elevation in blood also increases tyrosinase activity. There view. The arrow head indicates bipolar appearance of neona fore, inhibition of tyrosinase activity is one way to reduce tal foreskin primary human epidermal melanocyte (HEMn melanin synthesis. 45 MP). The mechanism of melanin formation inhibition can be FIG. 4 shows the effect of different concentrations of lin grouped into four categories: 1. reducing tyrosinase activity deranolide B and Subamolide A on Zebrafish pigment content. to inhibit melanin synthesis such as tyrosinase inhibitor; 2. It also includes test results of N-phenylthiourea and arbutin. minimizing melanocyte function with cytotoxic material to Control group value is set as 100%. reduce melanocyte proliferation or make it unable to produce 50 melanin; 3. reducing or preventing dihydroxyphenylalanine SUMMARY OF THE INVENTION auto-oxidation Such as anti-oxidant; and 4. inhibiting skin inflammation Such as inflammatory Swelling reaction after The present invention provides a composition for inhibit Sun exposure. Therefore, for skin whitening cosmetology ing melanogenesis, which comprises two extracts isolated usage, one can block UV, remove free radicals, inhibit tyro 55 from the stems of Cinnamomum subavenium—linderanolide sinase synthesis, inhibit tyrosinase activity and block melanin B and Subamolide A. These two components contain anti synthesis or fasten its metabolism and etc. tyrosinase ability, so as to inhibit melanogenesis in cells or More patents have been found as tyrosinase inhibitors Subjects and to be applied in whitening cosmetology. based on the first mechanism. Brief description is shown below. U.S. Pat. No. 5,723,109 used salicylic acid derivative 60 DETAILED DESCRIPTION OF THE INVENTION as tyrosinase inhibitor, and U.S. Pat. No. 5,730,962 revealed a synthetic benzofuran and its derivatives for tyrosinase inhi The present invention includes a Cinnamomum subave bition. nium extract which is obtained from the following steps: Several natural plant or food extracts also have tyrosinase extracting stems of Cinnamomum subavenium by organic inhibition effects. U.S. Pat. No. 5,824,320 reveals an extract 65 Solvent; adding product from previous step into water as and its derivatives from Aphloia and Mangifera leaf, which Suspension; adding chloroform solution to the Suspension to inhibits tyrosinase and collagenase activity. U.S. Pat. No. generate layers; separating chloroform layer from others; US 8,455,023 B2 3 4 applying chloroform layer to column liquid chromatography The solvate indicates that solvent molecule may be incor and eluting said extract with an alkane and ester mixture. The porated into the compound lattice during crystallization alkane of the present invention includes n-hexane and the forming a Solvate of said compound. ester of the present invention includes ethyl acetate. Both compounds have tyrosine kinase inhibition activity. The Cinnamomum subavenium extract of the present The composition or extract of the present invention can be invention can be added into drinks, cosmetics or pharmaceu added into drinks, cosmetics or pharmaceuticals. For tical products. The drinks include juices, tea, noodles, diary example,
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