KR20010038005A - Glycolipid Surfactant Produced from Microbe and Its Application - Google Patents

Glycolipid Surfactant Produced from Microbe and Its Application Download PDF

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KR20010038005A
KR20010038005A KR1019990045800A KR19990045800A KR20010038005A KR 20010038005 A KR20010038005 A KR 20010038005A KR 1019990045800 A KR1019990045800 A KR 1019990045800A KR 19990045800 A KR19990045800 A KR 19990045800A KR 20010038005 A KR20010038005 A KR 20010038005A
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glycolipid
based surfactant
torulopsis
acne
yeast
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김은기
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김은기
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/221—Mono, di- or trisaccharides or derivatives thereof
    • 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
    • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • 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

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

PURPOSE: Provided is a glycolipid-based surfactant having a pimple-bacteria inhibiting function and separated from Torulopsis yeast as a microorganism, which can be used for a shampoo and soap for cleansing the human body. CONSTITUTION: The glycolipid-based surfactant is produced from the Torulopsis yeast such as Torulopsis bambiocola ATCC22214, Torulopsis apicola, and Torulopsis petropriom . The glycolipid-based surfactant has structure having soporos saccharide as a hydrophilic group and fatty acid as a hydrophobic group. The product for cleansing the human body contains more than 0.0001% of the glycolipid-based surfactant.

Description

미생물로부터 분리된 여드름균 억제작용을 갖는 당지질계 계면활성제 및 그 용도{Glycolipid Surfactant Produced from Microbe and Its Application}Glycolipid Surfactant Produced from Microbe and Its Application}

본 발명은 미생물로부터 분리된 당지질계 계면활성제 및 그 용도에 관한 것으로서, 더욱 상세하게는 토루롭시스속 효모로부터 분리되며 여드름균 억제작용을 갖는 당지질계 계면활성제와 이를 포함하는 세정제에 관한 것이다.The present invention relates to a glycolipid-based surfactant separated from a microorganism and its use, and more particularly, to a glycolipid-based surfactant separated from Torulopsis yeast and having an inhibitory effect on acne bacteria and a cleaning agent comprising the same.

여드름이 생기는 이유는 도 1에 나타낸 바와 같이 모공근처에 여드름균이 침입, 성장하면서 염증을 유발하기 때문이다.The reason why acne occurs is that acne bacteria invade and grow near the pores, as shown in FIG. 1, causing inflammation.

일반적으로 여드름균의 생성을 억제, 치료하기 위해서 병원 등에서는 여드름이 심하여 피부감염이 있을 경우에는 레티놀산, 벤질 퍼옥사이드, 항생제, 호르몬제 등을 사용하여 여드름균의 성장을 방해하거나 피지 분비 등을 억제하는 치료방법을 사용해 오고 있다.In general, in order to suppress and treat the production of acne bacteria, in the case of severe acne in hospitals, retinol acid, benzyl peroxide, antibiotics, hormones, etc. are used to prevent acne bacteria growth or sebum secretion. It has been used to curb treatment.

그러나, 상기와 같은 방법을 포함한 여타의 종래의 방법들은 대부분 치료제의 개념으로, 레티놀산, 벤질퍼옥사이드 등은 자극성과 부작용이 보고되어 있다. 특히, 안구 자극성이 있어서 인체세정용 비누나 샴푸 등과 같은 제품에 첨가할 경우 피부 및 안구와 직접 접촉하게 되면 발진 등 부작용이 발생되는 문제점이 있다.However, other conventional methods including the above method are mostly the concept of a therapeutic agent, and retinol acid, benzyl peroxide, etc. have been reported to have irritation and side effects. In particular, there is a problem that the side effects such as rash occurs when the direct contact with the skin and the eye when added to products such as soap or shampoo for washing because of eye irritation.

또한, 항생제로 쓰이는 테트라사이클린, 어리스로마이신 등은 안구자극이 있고, 호르몬제인 에스트로겐 등은 호르몬 부작용으로 모공 확장 등의 후유증이 있으며 생산단가가 상당히 높아서 인체세정용 비누나 샴푸 등에는 사용할 수 없었다.In addition, tetracycline and erythromycin, which are used as antibiotics, have eye irritation, and estrogen, a hormone, has side effects such as enlargement of pores due to hormonal side effects.

한편, 치약 등에 사용되고 있는 항균제(이가산 또는 트리클로산)가 여드름균 억제제로도 사용될 수 있으나, 생산가격이 높아서 저가의 인체 세정용 제품에는 사용하기가 쉽지않다.On the other hand, antibacterial agents (diacids or triclosan) used in toothpaste, etc. can also be used as an acne bacteria inhibitor, but the production price is high, it is not easy to use for low-cost human cleansing products.

본 발명의 목적은 상기와 같은 문제점, 즉 자극성 및 부작용등을 해결하기 위한 것으로서, 저가의 새로운 여드름억제물질을 생산하여 이를 여드름균 억제 등의 목적에 적용할 수 있는 방법을 제공하는 데 그 목적이 있다.An object of the present invention is to solve the above problems, that is, irritation and side effects, and to provide a method that can be applied to the purpose of producing new low-cost acne inhibitors, such as acne bacteria suppression have.

이와같은 목적을 달성하기 위해 부단히 연구한 결과, 특정의 미생물로부터 분리되는 당지질이 여드름균 억제작용을 갖는 것을 확인하고, 이를 인체세정용 제품에 적용하였다.As a result of constant research in order to achieve this purpose, it was confirmed that the glycolipid separated from a specific microorganism has an acne bacterium inhibiting action, and it was applied to a product for human cleansing.

본 발명은 미생물로부터 분리된 당지질계 계면활성제가 여드름균 억제작용을 가짐을 확인하고, 이를 인체세정용 제품 등에 사용하는 방법에 그 특징이 있다.The present invention is characterized in that the glycolipid-based surfactant separated from the microorganism has an inhibitory effect on acne bacteria, and this method is used for cleaning products for humans.

도 1은 여드름 생성원인을 나타내는 모식도이고,1 is a schematic diagram showing the cause of acne production,

도 2는 토루롭시스속 효모로부터 분리된 소포로스를 포함한 당지질의 대표적인 구조를 나타낸 것이고Figure 2 shows a representative structure of glycolipids including Soporos separated from the genus Torolopsis yeast

도 3은 세포막과 당지질계 계면활성제의 상호작용을 개략적으로 나타낸 것이다.Figure 3 schematically shows the interaction between the cell membrane and the glycolipid-based surfactant.

본 발명에서는 우선 미생물로부터 분리되는 각종의 당지질에 대하여 그 활성을 관찰하였으며, 그 결과 토루롭시스속 효모로부터 생산되는 당지질계 계면활성제가 여드름균 억제작용에 활성이 있는 것을 확인하였다.In the present invention, the activity of the various glycolipids separated from the microorganisms was first observed, and as a result, it was confirmed that the glycolipid-based surfactant produced from the genus Torolopsis is active in inhibiting acne bacteria.

토루롭시스속 효모는 예전에는 칸디다속으로 분류되기도 하였으며, 이 효모는 출아법으로 성장하고 비수용성기질, 즉 기름, 지방등을 분해하면서 당지질을 생산하거나, 세포내에 지방을 축적하는 등의 특성이 밝혀져 있다.Torolopsis yeast was formerly classified as Candida, and this yeast grows by germination and produces glycolipids by breaking down water-soluble substrates such as oil and fat, or accumulate fat in cells. have.

또한, 3-4개의 유사구조의 당지질을 생산하는 것으로 알려져 있는 바, 대표적인 당지질 구조를 도 2에 나타내었다.In addition, it is known to produce glycolipids of 3-4 analogous structures, a typical glycolipid structure is shown in FIG. 2.

그러나, 지금까지 이와같은 당지질이 여드름균 억제효과를 갖는다는 것은 밝혀진 바 없었다However, it has not been found that such glycolipids have an inhibitory effect on acne.

토루롭시스속 효모로부터 여드름균 억제작용을 갖는 당지질은 도 2 및 도 3에 나타낸 바와 같이 친수성기로 소포로스당(도 2)과 소수성기로 지방산이 결합된 형태이다.As shown in FIGS. 2 and 3, glycolipids having an acne bacterium inhibiting activity from Torotropis yeast have a form in which a fatty acid is combined with a phosphosaccharide (FIG. 2) and a hydrophobic group with a hydrophilic group.

이를 생산하는 방법을 개략적으로 살펴보면, 회분식, 유가식 및 고정화 방법을 이용하며 각기 해당 미생물을 식용유, 포도당이 물 100중량부에 5∼15중량부를 탄소원으로 하는 배지에서 생산한다. 생산된 당지질에 계면활성제는 자연침전이나 용매를 사용하여 추출,분리한다.The method of producing this is outlined, using batch, fed-batch and immobilized methods, and each microorganism is produced in a medium containing 5 to 15 parts by weight of carbon oil in 100 parts by weight of cooking oil and glucose. Surfactants in the glycolipids produced are extracted and separated using natural precipitation or solvent.

이와같이 분리된 당지질계 계면활성제를 직접 또는 화학적 변화를 거쳐서 인체 세정용 비누나 샴푸 등에 적용하는 바, 이때 당지질계 계면활성제의 첨가량은 전체 세정제 조성 중 0.0001%이상인 것이 바람직하다. 만일, 함유되는 당지질계 계면활성제의 함량이 0.0001% 미만으로 첨가되면 그 첨가 효과가 미미하다. 함량을 증가시킬수록 효과가 증대되기는 하지만 경제성 등을 고려하여 5∼10% 범위를 상한으로 하는 것이 적절하다.The separated glycolipid surfactant is applied to a human washing soap or shampoo through direct or chemical change, and the addition amount of the glycolipid surfactant is preferably 0.0001% or more of the total detergent composition. If the content of the glycolipid-based surfactant contained is less than 0.0001%, the addition effect is insignificant. Although the effect increases as the content is increased, it is appropriate to set the upper limit in the range of 5 to 10% in consideration of economical efficiency.

이하에서 미생물로부터 당지질 형태의 계면활성제를 생산, 분리하는 방법을 구체적인 실시예로 설명하며, 분리된 당지질계 계면활성제의 여드름균 억제작용을 증거하고, 이를 세정용 제품에 적용하는 예를 드는 바, 본 발명이 본 실시예에 의해 한정되는 것은 아니다.Hereinafter, a method for producing and isolating a glycolipid-type surfactant from microorganisms will be described in specific embodiments, and the evidence of inhibiting acne bacteria of the isolated glycolipid-based surfactant will be given. The present invention is not limited by this embodiment.

실시예 1: 토루롭시스속 효모로부터 당지질계 계면활성제의 생산방법Example 1 Production of Glycolipid Surfactants from Torolopsis Yeast

사용된 균주는 토루롭시스 밤비오콜라(Torulopsis bombiocola) ATCC 22214를 ATCC에서 구입하여 사용하였고, YM 사면배지 형태로 4℃에서 저장, 사용하였다.As used strain, Torulopsis bombiocola ATCC 22214 was purchased from ATCC, and stored and used at 4 ° C. in the form of YM slope medium.

사용한 배지의 조성은 다음과 같으며, 추가기질로 카놀라 오일(canola oil)을 10%(wt/vol)씩을 사용하였다.The composition of the used medium was as follows, and 10% (wt / vol) of canola oil was used as an additional substrate.

배지조성(레인포스드 클로스트리디얼 메디움; 리터당 효모 추출물 3.0g, 비프 익스트랙트 10.0g, 펩톤 10.0g, 가용성 전분 1.0g, 포도당 5.0g, L-시스테인 하이드로클로라이드 0.5g, 염화나트륨 5.0g, 소듐 아세테이트 3.0g, 아가 0.75g, pH 6.8±0.2).Medium composition (Rainforced Clostrial media; 3.0 g of yeast extract per liter, beef extract 10.0 g, peptone 10.0 g, soluble starch 1.0 g, glucose 5.0 g, L-cysteine hydrochloride 0.5 g, sodium chloride 5.0 g, sodium acetate 3.0 g, agar 0.75 g, pH 6.8 ± 0.2).

48시간 동안 100㎖플라스크에 계대배양한 종균을 고압멸균한 2.5ℓ 발효기에 접종하여 7일동안 다음과 같은 상태로 운전하였다; 실제 배양액- 1ℓ, 온도-30℃, pH-3.5, 교반속도-550ppm, 공가공급속도-1vvm.The seedlings subcultured in a 100 ml flask for 48 hours were inoculated in a autoclaved 2.5 L fermenter and operated for 7 days as follows; Actual culture medium-1 L, temperature -30 DEG C, pH -3.5, stirring speed-550 ppm, feed rate-1 vmv.

배양이 끝난 후 당지질은 상등액에 포함되어 있거나 하부로 침전되었다. 이중 침전된 것은 분리, 수거하였다. 상등액은 배양 후 원심분리(5000rpm, 30분) 후 얻었다. 상등액에 포함된 당지질은 상등액을 에틸아세테이트(3회, 1ℓ)를 사용하여 추출하고, 추출액을 회전식 증발기에서 증발시켜 용매를 제거하여 미정제 당지질을 얻었다. 미정제 당지질에 다시 헥산을 첨가하여 잔류오일을 제거하고 클로로포름으로 용액 중의 당지질을 추출한 후 정제된 당지질 혼합물(90∼100g/ℓ)을 얻었다.After incubation, glycolipids were contained in the supernatant or precipitated downward. The double precipitated was separated and collected. The supernatant was obtained after incubation and centrifugation (5000 rpm, 30 minutes). The glycolipid contained in the supernatant was extracted with ethyl acetate (3 times, 1 L), and the extract was evaporated in a rotary evaporator to remove the solvent to obtain crude glycolipid. Hexane was added to the crude glycolipid to remove residual oil, and the glycolipid in the solution was extracted with chloroform to obtain a purified glycolipid mixture (90-100 g / L).

얻어진 당지질의 구조를 가스크로마토그라피와 및 TLC/FID를 통해 확인한 결과 대표적인 구조는 도 2와 같이 친수성기로 소포로스당과 소수성기로 지방산이 결합된 형태임을 확인하였다.As a result of confirming the structure of the obtained glycolipid through gas chromatography and TLC / FID, as shown in FIG. 2, it was confirmed that a fatty acid was combined with a hydrophobic group with a phosphosaccharide and a hydrophobic group.

실시예 2Example 2

여드름균인 프로푀니움 애크니균과 상기 실시예 1로부터 얻어진 당지질을 상기 실시예 1의 성장배지에서 37℃, 12시간 배양한 후 새로운 성장배지에 상기 당지질계 계면활성제를 첨가한 후 균의 성장속도를 측정하여 그 결과를 다음 표 1에 나타내었다.The acne bacterium Progenium acne bacteria and the glycolipid obtained from Example 1 were incubated for 12 hours at 37 ° C. in the growth medium of Example 1, and then the glycolipid-based surfactant was added to a new growth medium, followed by growth of the bacteria. The speed was measured and the results are shown in Table 1 below.

성장속도는 다음과 같은 식으로 구하였다.The growth rate was calculated as follows.

성장속도=Ln(X2/X1)/(t2-t1)(여기서, X2, X1는 시간 t2, t1에서의 세포농도)Growth rate = Ln (X 2 / X 1 ) / (t 2 -t 1 ) where X 2 and X 1 are the cell concentrations at time t 2 and t 1

한편, 균의 성장을 방해하기 시작하는 농도인 최소저해농도(MIC; Minimum Inibitory Concentration)를 고체배지에서 성장하는 콜로니수로 측정하여 그 결과를 다음 표 2에 나타내었다. 콜로니수는 0ppm의 콜로니수를 기준으로 환산한 것이고 대조구로서 현재 주로 사용되는 여드름치료제로서 이가산의 성능을 비교하였다.Meanwhile, the minimum inhibitory concentration (MIC; Minimum Inibitory Concentration), which is a concentration that starts to hinder the growth of bacteria, was measured by the number of colonies grown in a solid medium, and the results are shown in Table 2 below. The colony count was calculated based on the colony count of 0 ppm and compared with the performance of diacid as a control acne currently used as a control.

당지질 농도(ppm)Glycolipid concentration (ppm) 00 100100 500500 성장속도(hr-1)(%저해도)Growth rate (hr -1 ) (% degradation) 0.0328(0%)0.0328 (0%) 0.0174(46.95%)0.0174 (46.95%) 0.0116(64.63%)0.0116 (64.63%)

첨가제농도(ppm)Additive concentration (ppm) 콜로니 저해도(%)Colony inhibition (%) 당지질Glycolipid 이가산(기존사용제품)Igasan (existing product) 00 00 00 0.50.5 13.2513.25 -- 1One -- 00 22 26.0426.04 -- 33 -- 7.147.14 44 -- 10.710.7 55 -- 28.628.6 66 44.6844.68 -- 88 47.6847.68 -- 1010 43.4843.48 -- 5050 100100 100100 100100 100100 500500 100100 10001000 100100

상기 표 1의 결과로부터 토루롭시스속 효모로부터 생산, 분리된 당지질계 계면활성제를 첨가한 후 여드름균의 성장속도가 감소되는 것을 알 수 있으며, 표 2의 결과로부터 0.5ppm이라는 아주 낮은 농도에서부터 여드름균 저해능을 가짐을 알 수 있다. 이는 기존에 사용되던 이가산이 3ppm에서부터 저해능을 보이는것에 비해 효과적임을 알 수있다.It can be seen from the results of Table 1 that the growth rate of acne bacteria is reduced after adding the glycolipid-based surfactant produced and separated from the genus Torolopsis yeast, and from the very low concentration of 0.5 ppm from the results of Table 2 It can be seen that it has a bacterial inhibitory ability. This shows that the diacid used in the past is more effective than showing inhibition from 3ppm.

이와같은 작용을 개략적으로 나타내면 도 4와 같은 바, 당지질계 계면활성제가 프로푀니움 애크니균의 세포막의 안정도를 저해시킨다. 세포막은 계면활성제능을 가진 인지질이 나란히 늘어선 형태의 막으로서, 여기에 구조가 다른 계면활성제 분자, 예를들면 본 발명의 당지질계 계면활성제가 끼어들어 세포막의 구조가 변하고, 이로인해 세포막의 터짐으로 여드름균이 성장하지 못하도록 하는 것이다.4, the glycolipid-based surfactant inhibits the stability of the prokium acini bacterium. Cell membranes are membranes in the form of phospholipids with a surfactant function, and the surfactant molecules having different structures, for example, the glycolipid-based surfactants of the present invention, are intercalated to change the structure of the cell membranes, thereby causing the cell membranes to burst. Prevent acne bacteria from growing.

이상에서 상세히 설명한 바와 같이, 본 발명에 따라 미생물, 특히 토루롭시스속 효모로부터 생산, 분리된 당지질계 계면활성제는 아주 낮은 농도에서도 여드름균 저해활성을 가짐을 확인할 수 있었고, 이를 직접 또는 화학적 변화를 통해 인체세정제품에 적용하는 경우 적은 양의 첨가로도 여드름균 억제작용을 갖는 제품을 제조할 수 있었다.As described in detail above, the glycolipid-based surfactant produced and isolated from microorganisms, in particular toroloposis yeast, according to the present invention was found to have an acne bacterium inhibitory activity even at very low concentrations, and it may be directly or chemically changed. When applied to human cleansing products through the addition of a small amount was able to manufacture a product having an inhibitory action of acne.

Claims (6)

미생물로부터 분리되며, 여드름균 억제작용을 갖는 당지질계 계면활성제.Glycolipid-based surfactant, which is isolated from microorganisms and has an acne bactericidal action. 제 1 항에 있어서,The method of claim 1, 미생물은 토루롭시스속 효모인 것임을 특징으로 하는 당지질계 계면활성제.Glycolipid-based surfactant, characterized in that the microorganism is a genus Torolopsis yeast. 제 1 항 또는 제 2 항에 있어서,The method according to claim 1 or 2, 미생물은 토루롭시스 밤비오콜라 ATCC22214, 토루롭시스 아피콜라, 토루롭시스 페트로피리옴 인 것임을 특징으로 하는 당지질계 계면활성제.The microorganism is a glycolipid-based surfactant, characterized in that Torolopsis bambiocola ATCC22214, Torolopsis apicola, Torolopsis petropyriom. 제 1 항 또는 제 2 항에 있어서,The method according to claim 1 or 2, 당지질계 계면활성제는 친수성기로 소포로스당과 소수성기로 지방산이 결합된 구조를 갖는 것임을 특징으로 하는 당지질계 계면활성제.Glycolipid-based surfactant is a glycolipid-based surfactant, characterized in that the hydrophobic group has a structure in which the fatty acid is bonded to the phophos sugar and the hydrophobic group. 제 1 항에 이의 당지질계 계면활성제를 포함하는 인체세정용 제품.Claim 1, the human body cleaning product comprising a glycolipid-based surfactant thereof. 제 5 항에 있어서,The method of claim 5, 당지질계 계면활성제는 0.0001%이상으로 함유된 것임을 특징으로 하는 인체세정용 제품.Glycolipid surfactant is a product for human cleansing, characterized in that it contains more than 0.0001%.
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FR3132638A1 (en) * 2022-02-17 2023-08-18 L'oreal Use of rhamnolipid(s) to prevent staining of cutaneous blackheads

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3132638A1 (en) * 2022-02-17 2023-08-18 L'oreal Use of rhamnolipid(s) to prevent staining of cutaneous blackheads
WO2023156588A1 (en) * 2022-02-17 2023-08-24 L'oreal Use of rhamnolipid(s) for preventing the colouration of cutaneous blackheads

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