KR20020073624A - Novel use of decursin as melanin synthetic inhibitor - Google Patents

Novel use of decursin as melanin synthetic inhibitor Download PDF

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KR20020073624A
KR20020073624A KR1020010013322A KR20010013322A KR20020073624A KR 20020073624 A KR20020073624 A KR 20020073624A KR 1020010013322 A KR1020010013322 A KR 1020010013322A KR 20010013322 A KR20010013322 A KR 20010013322A KR 20020073624 A KR20020073624 A KR 20020073624A
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cell line
melanin
melanin synthesis
decursin
tyrosinase
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KR100379191B1 (en
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김익환
김윤미
김현호
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학교법인고려중앙학원
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

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  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Cosmetics (AREA)

Abstract

PURPOSE: Decursin having a melanin inhibiting activity generated by ultraviolet rays and inhibiting tyrosinase activity playing an important role in melanin synthesis is provided which can be used as a skin whitening composition as well as a melanin synthesis inhibitor. CONSTITUTION: The use of decursin as a melanin synthesis inhibitor is identified by treating a B16F10 cell line as a rat melanoma cell line and a G361 cell line as a human melanoma cell line with the decursin, and then measuring a synthetic amount of melanin induced by ultraviolet rays and tyrosinase. The melanin synthesis inhibitor and a skin whitening composition contain 1 to 50 μM decursin as an effective component.

Description

멜라닌 합성 저해제로서의 데커신의 신규한 용도{Novel use of decursin as melanin synthetic inhibitor}Novel use of decursin as melanin synthetic inhibitor

본 발명은 멜라닌 합성 저해제로서의 데커신의 신규한 용도에 관한 것이다.더욱 상세하게는, 본 발명은 자외선에 의해서 발생하는 멜라닌 합성 저해활성을 가지며 멜라닌 합성에 중요한 역할을 하는 타이로시나아제의 활성을 저해하는 데커신에 관한 것이다.The present invention relates to a novel use of deckerin as a melanin synthesis inhibitor. More specifically, the present invention has a melanin synthesis inhibitory activity generated by ultraviolet light and inhibits the activity of tyrosinase, which plays an important role in melanin synthesis. It's about Decker's.

멜라닌(melanin)은 자외선(UV)으로부터 인체의 피부를 보호하는 생체 내 색소이다. 또한 멜라닌은 피부의 과다한 자외선 노출에 의해서 야기되는 광암화(photocarcinogenesis)나 광노화(photoaging)에 대해서도 보호 효과를 갖는다. 그러나 이러한 멜라닌의 합성이 과다하게 되면 피부암이나 피부노화 등의 부작용을 보인다.Melanin is a pigment in vivo that protects the human skin from ultraviolet (UV) light. Melanin also has a protective effect against photocarcinogenesis or photoaging caused by excessive UV exposure of the skin. However, excessive synthesis of melanin shows side effects such as skin cancer and skin aging.

데커신은 바디나물에서 처음 분리된 후, 한국산 당귀와 기름나물의 과실에서도 분리된 바가 있다. 피라노쿠마린 계열의 데커신은 암세포에 대해서 강한 치사작용을 나타내는 항암제이며 세포 내의 신호전달에 중요한 역할을 하는 프로틴 키나아제 씨(protein kinase C)를 활성화 시키는 물질로 알려져 있다.After decosin was first isolated from the body sprouts, it was also isolated from the fruits of Korean Angelica and oil herb. Pyranocmarin-based decusin is an anticancer agent that has a strong lethal action against cancer cells and is known to activate protein kinase C, which plays an important role in cellular signaling.

본 발명자들은 데커시놀을 산 클로라이드 화합물과 반응시켜 데커신 및 그 유도체들을 합성하고 상기 합성물들의 항암활성과 암세포 특이성을 확인함으로써 항암제로서의 데커신의 유도체 및 그 합성방법에 관하여 특허출원한 바 있다 (출원번호 제 00-35750)The present inventors have filed a patent application for a derivative of decansin as an anticancer agent and a method for synthesizing the compound by decosinol reacting with an acid chloride compound to synthesize decansin and its derivatives and confirming the anticancer activity and the specificity of cancer cells. No. 00-35750)

본 발명자들은 계속적인 연구에서 항암활성, 세포 내 신호전달 조절 외에 데커신이 멜라닌의 합성을 저해하는 활성을 가짐을 밝혀 내었으며, 또한 데커신이 멜라닌 합성에 중요한 역할을 하는 효소인 타이로시나아제(tyrosinase)의 활성도 직접적으로 저해하는 활성을 확인하므로써 본 발명을 완성하였다.In a continuing study, the present inventors have found that in addition to anticancer activity and intracellular signaling regulation, deckerin has an activity that inhibits melanin synthesis, and also tyrosinase, an enzyme that plays an important role in melanin synthesis. This invention was completed by confirming the activity which also directly inhibits the activity of).

따라서 본 발명의 목적은 멜라닌 합성 저해제로서의 데커신의 신규한 용도를 제공함에 있다.It is therefore an object of the present invention to provide a novel use of decusin as a melanin synthesis inhibitor.

본 발명의 상기 목적은 자외선에 의한 설치류 멜라노마 세포주인 B16F10과 인간 멜라노마 세포주인 G361 세포주에 데커신을 처리하고 자외선 B에 의해서 유도되는 멜라닌 합성량과 티로시나아제를 직접 저해 여부를 측정함으로써 달성하였다.The above object of the present invention was achieved by treating decansin in rodent melanoma cell line B16F10 and human melanoma cell line G361 cell line by UV and measuring the amount of melanin synthesis and tyrosinase directly induced by UV light B. .

이하, 본 발명의 구성을 설명한다.Hereinafter, the configuration of the present invention will be described.

도 1은 자외선 B(UVB)에 의한 B16F10과 G361세포주의 성장저해를 측정한 그래프이다. A : B16F10 세포주, B :G361 세포주1 is a graph measuring growth inhibition of B16F10 and G361 cell lines by ultraviolet light B (UVB). A: B16F10 cell line, B: G361 cell line

도 2는 자외선 B에 의한 B16F10과 G361 세포주에서의 멜라닌합성 유도를 조사한 결과이다. A : B16F10 세포주, B :G361 세포주Figure 2 shows the results of the melanin synthesis induction of B16F10 and G361 cell line by ultraviolet light B. A: B16F10 cell line, B: G361 cell line

도 3은 데커신에 의한 B16F10과 G361 세포주의 성장저해를 조사한 결과이다.3 shows the results of investigating growth inhibition of B16F10 and G361 cell lines by Decusin.

A : B16F10 세포주, B :G361 세포주A: B16F10 cell line, B: G361 cell line

도 4는 데커신의 자외선 B에 의해서 유도되는 멜라닌 합성저해를 조사한 결과이다. A : B16F10 세포주, B :G361 세포주4 is a result of investigating the melanin synthesis inhibition induced by ultraviolet light B of Deckerin. A: B16F10 cell line, B: G361 cell line

도 5는 데커신에 의한 세포 내 타이로시나아제의 저해를 조사한 결과이다.5 shows the results of investigating the inhibition of intracellular tyrosinase by decusin.

본 발명은 자외선에 의한 설치류 멜라노마 세포주인 B16F10과 인간 멜라노마 세포주인 G361 세포주의 성장저해를 조사하는 단계; 자외선 B에 의한 B16F10과 G361의 세포주에서의 멜라닌 합성량을 측정하는 단계; 데커신에 의한 B16F10과 G361 세포주의 성장저해를 조사하는 단계; 데커신을 처리하고 자외선 B에 의해서 유도되는 멜라닌 합성량을 조사하는 단계; 데커신과 그 유도체들의 티로시나아제를 직접 저해하는지 여부를 측정하는 단계로 구성된다.The present invention comprises the steps of investigating the growth inhibition of rodent melanoma cell line B16F10 and human melanoma cell line G361 cell line by ultraviolet light; Measuring the amount of melanin synthesis in the cell lines of B16F10 and G361 by ultraviolet B; Investigating the growth inhibition of B16F10 and G361 cell lines by Decusin; Treating the decusin and examining the amount of melanin synthesis induced by ultraviolet light B; And determining directly inhibiting tyrosinase of the decusin and its derivatives.

본 발명에서 사용한 자외선에 의한 설치류 멜라노마 세포주인 B16F10과 인간 멜라노마 세포주인 G361 세포주는 각각 RPM11604 배지에서 37℃, 5% CO2조건에서 배양하였다.The rodent melanoma cell line B16F10 and the human melanoma cell line G361 cell line, which were used in the present invention, were cultured at 37 ° C. and 5% CO 2 conditions in RPM11604 medium, respectively.

이하, 본 발명의 구체적인 방법을 실시예를 들어 상세히 설명하고자 하지만 본 발명의 권리범위는 이들 실시예에만 한정되는 것은 아니다.Hereinafter, the specific method of the present invention will be described in detail with reference to Examples, but the scope of the present invention is not limited only to these Examples.

실시예 1: 자외선 B (UVB)에 의한 B16F10과 G361 세포주의 성장저해Example 1 Growth Inhibition of B16F10 and G361 Cell Lines by Ultraviolet B (UVB)

자외선 조사에 의한 B16F10과 G361 세포주의 성장 저해를 조사하기 위해서 각각의 세포주를 RPMI1640 배지에서 37℃, 5% CO2의 조건으로 배양하였다. 세포의 수를 1 × 106으로 맞추어, 자외선을 각각의 시간동안 조사하였다. 48시간 후, 세포의 생존율과 세포수를 측정하였다. 세포의 생존율은 트리판블루를 이용하여 측정하였으며 각각의 세포수를 측정하여 대조군과 비교하였다.In order to investigate growth inhibition of B16F10 and G361 cell lines by UV irradiation, each cell line was incubated at 37 ° C. and 5% CO 2 in RPMI1640 medium. The number of cells was adjusted to 1 × 10 6 , and ultraviolet light was irradiated for each time. After 48 hours, cell viability and cell number were measured. Cell viability was measured using trypan blue and the number of each cell was measured and compared with the control group.

실험결과 도 1에 나타난 바와 같이, B16F10 세포주(A)에서는 20초 이상 자외선을 조사하면 세포의 수가 감소하고 세포의 생존율도 감소하였으며 G361 세포주(B)에서는 자외선의 조사시간이 증가할수록 세포수와 세포의 생존율이 급격히 감소함을 보였다.As shown in FIG. 1, in the B16F10 cell line (A), irradiation of UV light for 20 seconds or more decreased the number of cells and the survival rate of the cell. In the G361 cell line (B), the number of cells and cells increased as the irradiation time of UV light increased. Survival rate decreased dramatically.

자외선의 조사에 의한 멜라닌의 합성량을 보기 위해서는 세포의 수나 생존율의 감소가 없는 범위 내에서 자외선을 조사하여야 하므로 멜라닌 합성을 위한 자외선의 조사시간은 10초로 결정하였다.In order to see the amount of melanin synthesized by the irradiation of UV light, the irradiation time of UV light for melanin synthesis was determined to be within 10 seconds without decreasing the number of cells or survival rate.

실시예 2 : 자외선 B에 의한 B16F10과 G361 세포주에서의 멜라닌합성 유도Example 2 Induction of Melanin Synthesis in B16F10 and G361 Cell Lines by Ultraviolet B

B16F10 세포주와 G361 세포주에 각각의 시간동안 자외선을 조사한 후, 48시간동안 배양하였다. 세포를 수거하여 세포내의 멜라닌 양을 측정하였으며, 증가된 멜라닌의 생성 양을 대조군과 비교하였다.The B16F10 cell line and the G361 cell line were irradiated with UV light for each hour, and then cultured for 48 hours. The cells were harvested to measure the amount of melanin in the cells and the increased amount of melanin produced was compared to the control.

실험결과 도 2에 나타낸 바와 같이, B16F10 세포주(A)에서는 자외선에 노출된 시간이 증가할수록 멜라닌의 양이 최대 180%까지 증가되는 결과를 얻었으나 G361 세포주(B)에서는 자외선의 조사시간에 따라서 멜라닌의 합성양이 150% 까지 증가되기는 하나 30초 이상 자외선을 조사하면 세포의 생존율이 급격하게 감소하여 멜라닌의 양을 측정 할 수가 없었다.As shown in FIG. 2, in the B16F10 cell line (A), the amount of melanin increased up to 180% as the exposure time to ultraviolet light increased. However, in the G361 cell line (B), the melanin according to the irradiation time of Although the synthesis amount of was increased to 150%, irradiation of ultraviolet rays for 30 seconds or more rapidly reduced the cell survival rate, and thus could not measure the amount of melanin.

실시예 3 : 데커신에 의한 B16F10과 G361 세포주의 성장저해Example 3 Growth Inhibition of B16F10 and G361 Cell Lines by Decusin

데커신에 의한 B16F10과 G361 세포주의 성장 저해를 조사하기 위해서 각각의 세포주를 RPMI1640 배지에서 37℃, 5% CO2의 조건으로 배양하였다. 세포의 수를 2 × 105으로 맞추어, 각각의 데커신을 첨가하였다. 48시간 후, 세포의 생존율과 세포수를 측정하였다. 세포의 생존율은 트리판블루를 이용하여 측정하였으며 각각의 세포수를 측정하여 대조군과 비교하였다.In order to investigate the growth inhibition of B16F10 and G361 cell lines by decusin, each cell line was incubated at 37 ° C. and 5% CO 2 in RPMI1640 medium. The number of cells was adjusted to 2 x 10 5 and each deckerin was added. After 48 hours, cell viability and cell number were measured. Cell viability was measured using trypan blue and the number of each cell was measured and compared with the control group.

실험결과 도 3에 나타낸 바와 같이, B16F10 세포주(A)의 경우 10 μM 과 25 μM의 데커신에서는 성장의 저해가 일어나지 않았으나 50 μM의 데커신은 약 50% 정도의 성장 저해가 일어났다. G361 세포주(B)는 B16F10 세포주에 비해서 데커신의 농도에 따라 성장 저해가 현격하게 일어났으며 약 25 μM의 농도에서 50%의 성장 저해를 보였다.As shown in FIG. 3, in the case of the B16F10 cell line (A), growth inhibition did not occur in 10 μM and 25 μM of Deckerin, but 50 μM of Deckerin caused about 50% of growth inhibition. In the G361 cell line (B), growth inhibition was remarkable according to the concentration of Deckerin compared to the B16F10 cell line, and showed a 50% growth inhibition at a concentration of about 25 μM.

실시예 4 : 데커신의 자외선 B에 의해서 유도되는 멜라닌 합성 저해Example 4 Inhibition of Melanin Synthesis Induced by Ultraviolet B of Decusin

B16F10과 G361 세포주를 각 농도의 데커신이 첨가된 배지에서 24시간동안 배양한 후, 자외선을 조사하였다. 자외선의 조사시간은 적당한 세포의 생존율과 세포수를 맞추기 위하여 30초로 고정하였다. 데커신이 없는 배지에서 48시간동안 배양한 후, 멜라닌의 양을 측정하였다.The B16F10 and G361 cell lines were incubated for 24 hours in a medium containing decansin at each concentration, followed by ultraviolet irradiation. UV irradiation time was fixed at 30 seconds to match the appropriate cell viability and cell number. After 48 hours of incubation in a decosin-free medium, the amount of melanin was measured.

측정결과 도 4에 나타낸 바와 같이, B16F10 세포주(A)는 자외선의 조사에 의해서 멜라닌의 합성양이 약 150% 정도 증가되었으며 데커신을 처리한 경우에는 멜라닌의 합성양이 감소하는 결과를 보였으며 자외선을 조사하지 않은 경우에서도 데커신은 멜라닌의 합성양을 감소시키는 결과를 보였다. 또한 G361 세포주(B)에서는 자외선의 조사에 의해서 약 140% 정도의 멜라닌 합성의 증가를 보였으며 B16F10 세포주에서와 마찬가지로 데커신에 의해서 멜라닌의 합성이 감소돠었다.As shown in FIG. 4, the B16F10 cell line (A) increased melanin synthesis by about 150% by irradiation with ultraviolet rays, and the melanin synthesis amount decreased when treated with Deckerin. Even if not investigated, decusin reduced the amount of melanin synthesis. In the G361 cell line (B), the melanin synthesis was increased by about 140% by UV irradiation, and the melanin synthesis was decreased by Deckerin as in the B16F10 cell line.

실시예 5 : 데커신에 의한 세포 내 타이로시나아제의 저해Example 5 Inhibition of Intracellular Tyrosinase by Decusin

데커신이 멜라닌합성에 중요한 역할을 하는 타이로시나아제를 직접 저해하는지 여부를 조사하였다. 타이로신나아제는 버섯에서 분리한 것을 사용하였으며3H로 표시한 타이로신(L-3,5-3H-tyrosine)을 기질로 사용하여 타이로시나아제의 활성을 측정하였다. 반응 후,3H2O의 양을 측정하여 대조군과 비교하였다. 타이로시나아제에 미치는 효과는 데커신과 같이 프로틴키나아제씨(protein kinase C, PKC)를 활성화 시키는 PMA와 비교하였다.We investigated whether decosin directly inhibits tyrosinase, which plays an important role in melanin synthesis. Tyrosine better claim was used that was separated from the mushrooms was measured by tyrosine (L-3,5- 3 H-tyrosine ) using as a substrate of the kinase activity or when the tie shown as 3 H. After the reaction, the amount of 3 H 2 O was measured and compared with the control. The effect on tyrosinase was compared with PMA, which activates protein kinase C (PKC), like decosin.

실험결과 도 5에 나타난 바와 같이, 데커신과 PMA는 모두 PKC를 활성화 시키는 인자로 알려져 있다. 하지만 멜라닌 합성에 중요한 역할을 하는 타이로시나아제의 저해에 있어서는 다른 양상을 보였다. 50 μM의 데커신이 대조군에 비해서 약 35%의 타이로시나아제 활성의 감소를 보인 반면, PMA는 약간의 활성 증가를 보였다. 이는 데커신이 세포 내 신호 전달 조절인자로서 멜라닌의 합성을 저해하는 경로외에 직접 타이로시나아제에 작용하여 이 효소의 활성을 감소시킴으로써 멜라닌의 합성을 감소시킬 수도 있다는 사실을 보이는 결과라고 할 수 있다.As shown in FIG. 5, both decusin and PMA are known as factors that activate PKC. However, there is another aspect of the inhibition of tyrosinase, which plays an important role in melanin synthesis. PMA showed a slight increase in activity, while 50 μM of decusin showed a decrease in tyrosinase activity of about 35% compared to the control. This results in the fact that dekerin may reduce the melanin synthesis by directly acting on tyrosinase to reduce the activity of the enzyme, in addition to the pathway that inhibits the synthesis of melanin as an intracellular signal transduction regulator.

따라서 데커신은 세포 내의 신호 전달에 중요한 역할을 하는 PKC의 활성을 조절하고 타이로시나아제의 활성을 저해함으로써 B16F10 세포주와 G361 세포주에서의 자외선에 의한 멜라닌 합성을 저해하는 것으로 사료된다.Therefore, decusin is thought to inhibit melanin synthesis by UV light in B16F10 and G361 cell lines by regulating PKC activity, which plays an important role in intracellular signal transduction, and inhibiting tyrosinase activity.

이상, 상기 실시예를 통하여 설명한 바와 같이, 본 발명은 항암제로서의 용도가 알려진 데커신의 멜라닌 합성 저해제로서의 신규한 용도를 제공하기 위하여 데커신의 멜라닌 생성 저해능 및 티로시나아제 활성을 측정한 결과 멜라닌 합성 저해하는 활성과 티로시나아제의 억제 활성이 뛰어난 효과가 있으므로 생물의약 산업상 매우 유용한 발명인 것이다.As described above, the present invention provides melanin synthesis inhibitory activity and tyrosinase activity of deckerin to provide a novel use as a melanin synthesis inhibitor of deckerin, which is known as an anticancer agent. Since the activity and inhibitory activity of tyrosinase have an excellent effect, it is a very useful invention in the biopharmaceutical industry.

Claims (2)

데커신을 유효성분으로 함유함을 특징으로 하는 멜라닌 합성 저해제 및 피부 미백용 조성물.Melanin synthesis inhibitor and skin whitening composition, characterized in that it contains deckerin as an active ingredient. 제 1항에 있어서 상기 데커신의 함량이 1uM∼50uM임을 특징으로 하는 멜라닌 합성 저해제 및 피부 미백용 조성물.The melanin synthesis inhibitor and the skin whitening composition according to claim 1, wherein the content of the decusin is 1 uM to 50 uM.
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WO2016137270A1 (en) * 2015-02-27 2016-09-01 (주)아모레퍼시픽 Method for predicting side effect of whitening ingredient
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WO2008102994A1 (en) * 2007-02-22 2008-08-28 Yong Jin Park Composition comprising decursin derivative for treating and preventing atopic dermatitis
WO2016137270A1 (en) * 2015-02-27 2016-09-01 (주)아모레퍼시픽 Method for predicting side effect of whitening ingredient
KR20160105646A (en) * 2015-02-27 2016-09-07 (주)아모레퍼시픽 A method of predicting side effects of a whitening ingredient
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KR102526200B1 (en) 2022-08-12 2023-04-26 양지혜 Composition for Skin Moisturizing and Whitening Comprising Decurcinol as Active Ingredient

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