KR20100130885A - Antibacterial compounds from dryopteris crassirhizoma and composition containing thereof - Google Patents

Antibacterial compounds from dryopteris crassirhizoma and composition containing thereof Download PDF

Info

Publication number
KR20100130885A
KR20100130885A KR1020090049627A KR20090049627A KR20100130885A KR 20100130885 A KR20100130885 A KR 20100130885A KR 1020090049627 A KR1020090049627 A KR 1020090049627A KR 20090049627 A KR20090049627 A KR 20090049627A KR 20100130885 A KR20100130885 A KR 20100130885A
Authority
KR
South Korea
Prior art keywords
compound
antibacterial
staphylococcus
antimicrobial
streptococcus
Prior art date
Application number
KR1020090049627A
Other languages
Korean (ko)
Other versions
KR101104388B1 (en
Inventor
이향범
Original Assignee
전남대학교산학협력단
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 전남대학교산학협력단 filed Critical 전남대학교산학협력단
Priority to KR1020090049627A priority Critical patent/KR101104388B1/en
Publication of KR20100130885A publication Critical patent/KR20100130885A/en
Application granted granted Critical
Publication of KR101104388B1 publication Critical patent/KR101104388B1/en

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/11—Pteridophyta or Filicophyta (ferns)
    • A61K36/12—Filicopsida or Pteridopsida
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Mycology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Microbiology (AREA)
  • Engineering & Computer Science (AREA)
  • Medical Informatics (AREA)
  • Botany (AREA)
  • Biotechnology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

PURPOSE: An antibacterial flavaspidic acid compound and an antibacterial composition containing thereof are provided to secure the antibacterial effect for methicillin resistant Staphylococcus aureus. CONSTITUTION: An antibacterial flavaspidic acid compound is marked with chemical formula 1. In the chemical formula 1, R is either a methyl group or an ethyl group. The flavaspidic acid compound is separated from an ethanol extract of Crassirhizomae Rhizoma. The flavaspidic acid compound has the antibacterial activation for more than one strain selected from the group consisting of Staphylococcus sp., Bacillus sp., Streptococcus sp., and E.coli.

Description

관중으로부터 얻은 항균 활성을 나타내는 화합물 및 이를 포함하는 항균 조성물{Antibacterial compounds from Dryopteris crassirhizoma and composition containing thereof}Antibacterial compounds from Dryopteris crassirhizoma and composition containing thereof

본 발명은 관중(Dryopteris crassirhizoma)으로부터 얻을 수 있으며, 항균 활성을 나타내는 플로르글루시놀계 화합물로서 플라바스피딕 산 화합물과, 상기 화합물을 포함하는 항균 조성물에 관한 것이다. The present invention can be obtained from a crowd ( Dryopteris crassirhizoma ), and relates to a flavaspidic acid compound and a antimicrobial composition comprising the compound as a florglucinol-based compound exhibiting antimicrobial activity.

관중(Dryopteris crassirhizoma)은 양치식물 고사리목 면마과의 여러해살이 풀로 산지의 나무그늘에서 자라는 반상록(semi-evergreen) 식물이다. 관중은 일반적인 감기나, 독감과 같은 감염 질환에 대하여 효과가 있는 것으로 알려져 있으며, 최근에는 SARS의 예방에도 효과가 있는 것으로 밝혀진 바 있다. Spectators ( Dryopteris crassirhizoma ) are semi-evergreen plants growing in the bark of mountainous ferns in perennial herbaceous ferns. The crowd is known to be effective against common colds and infectious diseases such as the flu, and has recently been shown to be effective in preventing SARS.

관중으로부터 알바스피딘(albaspidin), 아스피딘(aspidin), 플라바스피딕 산(flavaspidic acid), 드리오크라신(dryocrassin) 등의 플로르글루시놀(Phloroglucinol) 화합물과 캠퍼롤 아세틸 람노사이드 등이 분리된 바 있으며, 대한민국 공개특허 제2008-8819호에서는 관중으로부터 분리된 아실플로르글루시놀 화합물이 지방산 합성을 저해하는 것에 대하여 나타내고 있다. Phloroglucinol compounds such as albaspidin, aspidin, flavaspidic acid, dryocrassin, and camphorol acetyl rhamnoside were separated from the crowd. In Korean Unexamined Patent Publication No. 2008-8819, the acylfloglucinol compound isolated from the crowd shows that the fatty acid synthesis is inhibited.

또한, 관중의 에테르 추출물이 in vitro 조건에서 스트렙토코커스 뮤탄스(Streptococcus mutans)에 대하여 항균 효과를 가진다는 점을 확인한 바 있으며(Do, D. S., Antibacterial components of Dryopteris crassirhizoma against a Streptococcus mutans OMZ 176), Helichrysum caespititium에서 유래한 아실화된 플로르글루시놀의 항균 활성에 대하여 연구가 진행된 바 있다. In addition, it has been confirmed that the ether extract of the spectators has an antimicrobial effect against Streptococcus mutans in vitro conditions (Do, DS, Antibacterial components of Dryopteris crassirhizoma against a Streptococcus mutans OMZ 176), Helichrysum The antimicrobial activity of acylated florglucinol derived from caespititium has been studied.

본 발명자들은 관중으로부터 추출한 화학식 1로 표시되는 화합물이 특정 세균에 대하여 항균 활성을 가진다는 점을 발견함으로써 본 발명을 완성하게 되었다. The present inventors have completed the present invention by discovering that the compound represented by the formula (1) extracted from the crowd has antibacterial activity against specific bacteria.

따라서 본 발명은 항균 활성을 나타내는 상기 플라바스파딕 산 화합물을 제공하는 것을 목적으로 한다. Accordingly, an object of the present invention is to provide the above-described flavaspadiic acid compound exhibiting antimicrobial activity.

또한 본 발명은 상기 플라바스피딕 산 화합물을 포함하는 항균제 조성물을 제공하는 것을 또다른 목적으로 한다. It is another object of the present invention to provide an antimicrobial composition comprising the flavaspidic acid compound.

본 발명은The present invention

하기 화학식 1로 표시되고 항균 활성을 나타내는 화합물을 특징으로 한다. It is characterized by a compound represented by the following formula (1) and showing an antimicrobial activity.

[화학식 1][Formula 1]

Figure 112009033998319-PAT00002
Figure 112009033998319-PAT00002

상기 화학식 1에서, R은 메틸 또는 에틸기이다. In Formula 1, R is a methyl or ethyl group.

또한, 본 발명은 상기 화합물을 포함하는 항균제 조성물을 그 특징으로 한다. In addition, the present invention is characterized by an antimicrobial composition comprising the compound.

본 발명의 화합물 및 이를 포함하는 항균제 조성물은 스타필로코커스균(Staphylococcus sp.), 바실러스균(Bacillus sp.), 스트렙토코커스균(Streptococcus sp.) 및 대장균(E.coli) 등에 대하여 우수한 항균 효과를 가지며, 특히 메티실린 내성 스타필로코커스 아우레우스(Methicillin resistant Staphylococcus aureus; MRSA)에 대하여 항균 효과를 가지고 있을 뿐만 아니라, 천연물인 관중으로부터 추출된 것이므로 부작용의 염려가 적어 천연항균제 또는 메티실린 내성 스타필로코커스 아우레우스 감염에 의한 질병 치료 및 예방에 가치가 높을 것으로 기대된다. Antimicrobial composition comprising a compound of the invention and it an excellent antimicrobial activities against microorganisms such as Staphylococcus (Staphylococcus sp.), Bacillus bacterium (Bacillus sp.), Streptococcus bacteria (Streptococcus sp.), And Escherichia coli (E.coli) In particular, it has an antimicrobial effect against Methicillin resistant Staphylococcus aureus (MRSA), and is extracted from the spectral body which is a natural product, so it is less concerned about side effects. It is expected to be of great value for the treatment and prevention of diseases caused by Caucasus aureus infection.

본 발명은The present invention

하기 화학식 1로 표시되고 항균 활성을 나타내는 화합물을 특징으로 한다. It is characterized by a compound represented by the following formula (1) and showing an antimicrobial activity.

[화학식 1][Formula 1]

Figure 112009033998319-PAT00003
Figure 112009033998319-PAT00003

상기 화학식 1에서, R은 메틸 또는 에틸기이다.In Formula 1, R is a methyl or ethyl group.

상기 화합물은 플로르글루시놀(Phloroglucinol)계 화합물로서, R이 메틸기인 것은 플라바스피딕 산(Flavaspidic acid) AB, R이 에틸기인 것은 플라바스피딕 산(Flavaspidic acid) PB에 해당한다. The compound is a fluoroglucinol-based compound, wherein R is a methyl group, and a Flavaspidic acid AB, and R is an ethyl group, corresponds to a Flavaspidic acid PB.

상기 화합물은 관중으로부터 유래된 것일 수 있으며, 알코올, 에테르, 케톤 등의 유기용매에 의한 추출, 컬럼크로마토그래피 방법과 같은 식물체 성분의 분리 추출에 이용되는 공지의 방법을 적절하게 조합하여 얻을 수 있으며, 당 분야에서 일반적으로 적용되는 공지기술 범주 내에서 이의 변경도 가능하다. 또한, 조 추출물은 필요에 따라 여러 번 반복 수행하여 정제할 수도 있다.The compound may be derived from the crowd, and may be obtained by appropriately combining known methods used for separation and extraction of plant components, such as extraction by organic solvents such as alcohol, ether, ketone, column chromatography, Modifications thereof are also possible within the scope of the known art generally applicable in the art. In addition, the crude extract may be purified by repeating as many times as necessary.

본 발명에서 사용되는 크로마토그래피에는 실리카겔 컬럼 크로마토그래피(silica gel column chromatography), LH-20 칼럼 크로마토그래피, 박층 크로마 토그래피(TLC; thin layer chromatography) 및 고성능 액체 크로마토그래피(high performance liquid chromatography) 등이 적용될 수 있다. Chromatography used in the present invention includes silica gel column chromatography, LH-20 column chromatography, thin layer chromatography (TLC) and high performance liquid chromatography, etc. Can be applied.

본 발명의 화합물은 다양한 병원성 미생물 대하여 항균 효과를 가지며, 보다 상세하게는 스타필로코커스균(Staphylococcus sp.), 바실러스균(Bacillus sp.), 스트렙토코커스균(Streptococcus sp.) 및 대장균(E.coli)에 대하여 항균 활성이 나타나며, 메티실린 내성 스타필로코커스 아우레우스(Methicillin resistant Staphylococcus aureus; MRSA)에 대하여도 항균 활성이 나타난다. The compound of the present invention has an antimicrobial effect against various pathogenic microorganisms, and more specifically, Staphylococcus sp., Bacillus sp., Streptococcus sp., And E. coli ) And antimicrobial activity against Methicillin resistant Staphylococcus aureus (MRSA).

또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 항균제 조성물을 권리범위로 포함한다. In addition, the present invention includes the antimicrobial composition comprising the compound represented by the formula (1) as a scope.

본 발명의 항균제 조성물은 상기 화학식 1로 표시되는 플라바스피딕 산 화합물을 단독으로 또는 플라바스피딕 산 화합물 0.001 내지 99 중량%와 사용 목적에 따라 적절히 선택된 첨가제를 함유할 수 있다. 본 발명은 이들 첨가제의 선택 사용 및 함량에 대해 특별히 제한을 두지 않으며, 당업계 종사하는 전문가 수준에서 사용방법 및 제형에 따라 적절히 조절이 가능하다. 즉, 본 발명의 첨가제는 통상의 항균제에 포함되는 물질 예를 들면, 부형제 또는 희석제일 수 있으며, 그 예로는 식염수, 완충용액, 덱스트로스, 이소파라핀, 물, 글리세롤, 에탄올이 사용될 수 있으며, 이에 한정되는 것은 결코 아니다.The antimicrobial composition of the present invention may contain 0.001 to 99% by weight of the flavaspidic acid compound represented by the formula (1) alone or an additive appropriately selected according to the purpose of use. The present invention is not particularly limited to the selective use and content of these additives, and can be appropriately adjusted according to the method of use and the dosage form at the expert level in the art. That is, the additive of the present invention may be a material included in a conventional antibacterial agent, for example, an excipient or a diluent, and examples thereof include saline solution, buffer solution, dextrose, isoparaffin, water, glycerol, and ethanol. It is by no means limited.

항균제의 제형은 사용방법 및 용도에 따라 적절히 조절할 수 있으며, 예컨대 액제, 현탁제, 과립제, 방향수제, 산제, 시럽제, 에어로졸제, 엑스제, 연고제, 유도엑스제, 유제, 전제, 점안제, 주사제, 주정제, 캅셀제, 크림제, 환제일 수 있다.The formulation of the antimicrobial agent can be appropriately adjusted according to the method of use and use, such as liquids, suspensions, granules, fragrances, powders, syrups, aerosols, extracts, ointments, derived extracts, emulsions, whole preparations, eye drops, injections, It may be a pill, a capsule, a cream, or a pill.

본 발명의 항균제 조성물은 인체 병원성 세균 및 식물병원성 세균 등의 생성 및 성장을 억제하기 위한 용도로, 세정제, 약제, 식품첨가제, 방향제, 화장제 및 생물제제로 사용 가능하다. 세정제로 사용하는 경우 분무제, 세척제, 샴푸, 린스, 비누 등으로 제조 가능하며, 이때 항균 조성물은 0.01 내지 50 중량%로 포함할 수 있으나, 이에 한정되는 것은 아니다. 약제로 사용하는 경우 소독제, 치료제, 예방제 등으로 사용 가능하며, 이때 항균 조성물의 투여량은 1일 1 내지 1000 mg일 수 있으나, 이에 한정되는 것은 아니다. 식품 첨가제로 사용하는 경우, 항균 조성물은 식품의 종류 및 사용방법에 따라 적절히 조절하는 것이 좋으며, 그 일례로 식품 중량에 대해 0.0001 내지 10 중량%로 사용할 수 있다. 방향제로 사용하는 경우, 휘발성 물질을 더욱 포함할 수 있으며, 항균제 조성물은 0.0001 내지 90 중량%로 사용할 수 있다. 화장제로 사용하는 경우, 항균제 조성물은 0.0001 내지 30 중량%로 포함될 수 있다.The antimicrobial composition of the present invention is used for inhibiting the production and growth of human pathogenic bacteria and phytopathogenic bacteria, and can be used as detergents, pharmaceuticals, food additives, fragrances, cosmetics and biologics. When used as a cleaning agent, it can be prepared as a spray, cleaning agent, shampoo, rinse, soap, etc., wherein the antimicrobial composition may include 0.01 to 50% by weight, but is not limited thereto. When used as a medicament can be used as a disinfectant, therapeutic agent, prophylactic agent, etc. At this time, the dosage of the antimicrobial composition may be 1 to 1000 mg per day, but is not limited thereto. When used as a food additive, the antimicrobial composition is preferably adjusted appropriately according to the type of food and the method of use, for example, it can be used in 0.0001 to 10% by weight relative to the food weight. When used as a fragrance, it may further include a volatile substance, the antimicrobial composition may be used in 0.0001 to 90% by weight. When used as a cosmetic, the antimicrobial composition may be included in 0.0001 to 30% by weight.

이하, 본 발명의 바람직한 실시예를 들어 본 발명을 더욱 상세히 설명하고자하나, 이는 본 발명을 예시하기 위한 것일 뿐 본 발명이 이에 한정되는 것은 아니다. Hereinafter, the present invention will be described in more detail with reference to preferred embodiments of the present invention, which is intended to illustrate the present invention, but the present invention is not limited thereto.

실시예 1 : 플로르글루시놀 화합물의 분리 및 정제Example 1 Isolation and Purification of Florglucinol Compound

채취된 관중의 뿌리를 건조시키고, 상기 건조된 관중 1kg을 잘게 부순 후 메탄올 3L에 2일간 침지하여 실온에서 2회 반복 추출하였다. 상기 추출 과정을 통하여 얻은 추출물을 감압 농축하여 흑갈색의 시럽 형태의 농축액을 얻었다. 그리고 상기 농축액 150g을 물 1L에 현탁시킨 후, 헥산(1L), 에틸아세테이트(1L) 및 n-부탄올(1L)로 순차적으로 각각 2회에 거쳐 용매 분획하였다. 에틸아세테이트 분획을 건조시킨 뒤, 상기 건조 에틸아세테이트 분획 80g을 아세톤과 핵산의 부피비가 1 : 9에서 8 : 2가 되도록 조절한 용매 구배 조건에서 실리카겔 컬럼크로마토그래피를 실시하여 11개의 분획을 얻었다. 상기 11개의 분획 중 5, 6번 분획 각각 8g을 세파덱스 LH-20 (Sephadex LH-20, Amersham, Sweden)로 정제하여 화합물 1(5 분획) 및 화합물 2(6분획)를 얻었다. 상기 화합물의 분리, 정제 방법은 도 1에 도식화하여 나타내었다. The roots of the collected tube were dried, and 1 kg of the dried tube was crushed finely and then immersed in 3 L of methanol for 2 days and extracted twice at room temperature. The extract obtained through the extraction process was concentrated under reduced pressure to obtain a concentrate of black brown syrup form. Then, 150 g of the concentrated solution was suspended in 1 L of water, and the solvent was fractionated twice each sequentially with hexane (1 L), ethyl acetate (1 L) and n-butanol (1 L). After drying the ethyl acetate fraction, the fraction of 80 g of the dried ethyl acetate fraction was subjected to silica gel column chromatography under a solvent gradient condition in which the volume ratio of acetone and nucleic acid was 1: 9 to 8: 2 to obtain 11 fractions. 8 g of each of 5 and 6 fractions of the 11 fractions was purified with Sephadex LH-20 (Sephadex LH-20, Amersham, Sweden) to obtain Compound 1 (5 fractions) and Compound 2 (6 fractions). The separation and purification method of the compound is shown schematically in FIG.

실시예 2 : 추출된 화합물의 특성 및 구조 분석Example 2 Characterization and Structure Analysis of the Extracted Compound

상기 화합물 1 및 2의 특성을 분석하기 위하여 녹는점(Electrothermal instrument, Dubuque, IA, USA), UV 스펙트라(Milton Roy 3000 spectrometer, Ivyland, PA, USA)를 측정하였다. 또한, 화합물의 구조를 분석하기 위하여 ESI 질량분석기(JMS 700 mass spectrometer, JEOL, Tokyo, Japan)로 분자량을 측정하였고, 1H- and 13C-NMR 은 DRX 300 MHz(Bruker, Karlsruhe, Germany)에서 측정하여 화합물의 구조를 결정하였다. Melting points (Electrothermal instrument, Dubuque, IA, USA) and UV spectra (Milton Roy 3000 spectrometer, Ivyland, PA, USA) were measured to characterize the compounds 1 and 2. In addition, the molecular weight was measured by ESI mass spectrometer (JMS 700 mass spectrometer, JEOL, Tokyo, Japan) to analyze the structure of the compound, 1 H- and 13 C-NMR was measured at DRX 300 MHz (Bruker, Karlsruhe, Germany) The measurement determined the structure of the compound.

(1) 플라바스피딕 산 PB(화합물 1)(1) Flavaspidic acid PB (Compound 1)

녹는점 : 148℃Melting Point: 148 ℃

UV λ max (CHCl3) nm (log ε) : 241 (3.81), 289 (3.78)UV λ max (CHCl 3 ) nm (log ε): 241 (3.81), 289 (3.78)

ESI-MS m/z: 431.2 [M-H]-, 455.2[M+Na]+ ESI-MS m / z: 431.2 [M − H] − , 455.2 [M + Na] +

1H-NMR(300MHz,CDCl3) : 0.99[3H,t(J=7.5Hz),H-11'], 1.10[3H,t(J=7.5Hz),H-11], 1.40[6H,s,H-7,8], 1.66[2H,m,H-10'], 2.05[3H,s,H-7'], 3.05[2H,t(J=7.5Hz),H-9'], 3.10[2H,q(J=7.5),H-10], 3.55[2H,s,H-1"]. 1 H-NMR (300MHz, CDCl 3 ): 0.99 [3H, t ( J = 7.5Hz), H-11 ′], 1.10 [3H, t ( J = 7.5Hz), H-11], 1.40 [6H, s, H-7,8], 1.66 [2H, m, H-10 '], 2.05 [3H, s, H-7'], 3.05 [2H, t ( J = 7.5Hz), H-9 '] , 3.10 [2H, q ( J = 7.5), H-10], 3.55 [2H, s, H-1 "].

Figure 112009033998319-PAT00004
Figure 112009033998319-PAT00004

(2) 플라바스피딕 산 AB(화합물 2)(2) Flavaspidic acid AB (Compound 2)

mp : 188-189℃mp: 188-189 ℃

UV λmax (CHCl3) nm (log ε) : 240 (3.85), 285 (3.79)UV λ max (CHCl 3 ) nm (log ε): 240 (3.85), 285 (3.79)

ESI-MS m/z : 417.3[M-H]-, 441.3[M+Na]+,ESI-MS m / z: 417.3 [M − H] − , 441.3 [M + Na] + ,

1H-NMR(300MHz,CDCl3) : 0.91[3H,t(J=7.5Hz),H-11'], 1.16[6H,s,H-7,8], 1.60[2H,m,H-10'], 1.87[3H,s,H-7'], 2.38[3H,s,H-10], 3.04[2H,t(J=7.5Hz),H-9'], 3.55[2H,s,H-12]. 1 H-NMR (300MHz, CDCl 3 ): 0.91 [3H, t ( J = 7.5Hz), H-11 ′], 1.16 [6H, s, H-7,8], 1.60 [2H, m, H- 10 '], 1.87 [3H, s, H-7'], 2.38 [3H, s, H-10], 3.04 [2H, t ( J = 7.5 Hz), H-9 '], 3.55 [2H, s , H-12].

Figure 112009033998319-PAT00005
Figure 112009033998319-PAT00005

실시예 3 : 화합물 1, 2의 항균활성 측정Example 3 Determination of Antimicrobial Activity of Compounds 1 and 2

상기 추출된 화합물 1, 2의 항균 활성을 측정하기 위하여 바실러스 섭틸리스(Bacillus subtilis KCTC 1914), 에스케리키아 콜리(Escherichia coli KCTC 1924), 스타필로코커스 아우레우스(Staphylococcus aureus KCTC 1916, KCTC 1928, EML 5757779) 및 스트렙토코커스 뮤탄스(Streptococcus mutans DSM 6178)를 대상으로 페이퍼 디스크(paper disc)법으로 가시화 실험을 수행하였다. Bacillus subtilis KCTC 1914, Escherichia coli KCTC 1924, Staphylococcus aureus KCTC 1916, KCTC 1928 to measure the antimicrobial activity of the extracted compounds 1 and 2 , EML 5757779) and Streptococcus mutans ( Streptococcus mutans DSM 6178) was performed by a paper disc (paper disc) visualization experiment.

상기 추출된 화합물 1, 2를 에탄올에 녹인 후 200㎍씩 페이퍼 디스크(Whatman NO.1, 8mm diameter)에 점적한 후, 상기 균주가 0.1ml 도말된 한천 플레이트 위에 올려놓고 24시간 동안 완전히 건조하였다. 이후, 저해 구역(inhibitory zone)의 크기를 측정하여 항균 활성을 확인하였으며, 그 결과를 하 기 표 1 및 도 2에 나타내었다. After dissolving the extracted compounds 1 and 2 in ethanol and dropping 200 μg on a paper disk (Whatman NO. 1, 8 mm diameter), the strain was placed on a 0.1 ml plated agar plate and completely dried for 24 hours. Then, the antimicrobial activity was confirmed by measuring the size of the inhibition zone (inhibitory zone), the results are shown in Table 1 and FIG.

균주Strain 저해 구역(inhibitory zone)의 크기(mm)Size of Inhibitory Zone (mm) 플라바스피딕 산 PB
(화합물 1)Flavaspidic acid PB
(Compound 1) 플라바스피딕 산 AB
(화합물 2)Flavaspidic acid AB
(Compound 2) Escherichia coli KCTC 1924 Escherichia coli KCTC 1924 1111 1111 Bacillus subtilis KCTC 1914 Bacillus subtilis KCTC 1914 1919 1515 Staphylococcus aureus KCTC 1916 Staphylococcus aureus KCTC 1916 1616 1616 Staphylococcus aureus KCTC 1928 Staphylococcus aureus KCTC 1928 1919 1919 Staphylococcus aureus EML 5757779 Staphylococcus aureus EML 5757779 1919 1919 Streptococcus mutans DSM 6178 Streptococcus mutans DSM 6178 1919 1818

상기 실험을 통하여 화합물 1, 2의 항균 활성을 확인할 수 있었으며, 특히 그람 양성균인 바실러스 섭틸리스, 스타필로코커스 아우레우스 및 스트렙토코커스 뮤탄스에서 그람 음성균인 에스케리키아 콜리에 비하여 상대적으로 우수한 항균 활성을 나타내는 것을 확인하였다. 또한 화합물 1, 2가 메티실린 내성 스타필로코쿠스 아우레우스(Methicillin resistant Staphylococcus aureus; MRSA)에 해당하는 스타필로코커스 아우레우스 KCTC 1928 균주에 대하여도 매우 우수한 항균 활성을 나타내는 것을 확인하였다.Through the above experiments, the antimicrobial activity of Compounds 1 and 2 was confirmed, and in particular, Gram-positive bacteria, Bacillus subtilis, Staphylococcus aureus, and Streptococcus mutans, were relatively superior to the Gram-negative bacteria Escherichia coli. It was confirmed to exhibit activity. It was also confirmed that Compounds 1 and 2 exhibited very good antibacterial activity against Staphylococcus aureus KCTC 1928 strain corresponding to Methicillin resistant Staphylococcus aureus (MRSA).

따라서 본 발명의 화합물이 다양한 균주에 대하여 우수한 항균 활성을 가짐을 알 수 있었다. Therefore, it was found that the compound of the present invention has excellent antimicrobial activity against various strains.

도 1은 본 발명의 화합물을 관중으로부터 추출, 분리하는 과정을 나타낸 모식도이다. 1 is a schematic diagram showing a process of extracting and separating a compound of the present invention from the audience.

도 2는 본 발명의 화합물의 항균활성을 페이퍼 디스크(paper disc)법으로 확인한 사진이다. 이 때, FL PB는 플라비스피딕 산 PB(화합물 1)을, FL AB는 플라비스피딕 산 AB(화합물 2)를 나타낸다. 2 is a photograph confirming the antimicrobial activity of the compound of the present invention by a paper disc method. At this time, FL PB stands for flavispidic acid PB (Compound 1), and FL AB stands for flavispidic acid AB (Compound 2).

Claims (7)

하기 화학식 1로 표시되고, 항균 활성을 나타내는 화합물 : A compound represented by the following Chemical Formula 1 and showing antibacterial activity: [화학식 1][Formula 1]
Figure 112009033998319-PAT00006
Figure 112009033998319-PAT00006
 상기 화학식 1에서, R은 메틸 또는 에틸기이다. In Formula 1, R is a methyl or ethyl group. 제 1 항에 있어서, 상기 화합물은 관중으로부터 유래된 것임을 특징으로 하는 화합물.The compound of claim 1, wherein the compound is derived from a crowd. 제 2 항에 있어서, 상기 화합물은 관중의 에탄올 추출물로부터 분리된 것임을 특징으로 하는 화합물.The compound of claim 2, wherein the compound is isolated from the ethanol extract in the tube. 제 1 항에 있어서, 상기 화합물이 스타필로코커스균(Staphylococcus sp.), 바실러스균(Bacillus sp.), 스트렙토코커스균(Streptococcus sp.) 및 대장균(E.coli)으로 이루어진 군으로부터 선택된 1종 이상의 균주에 대하여 항균 활성을 나타내는 것을 특징으로 하는 화합물.The method of claim 1 wherein the compound is a Staphylococcus bacteria (Staphylococcus sp.), Bacillus bacterium (Bacillus sp.), Streptococcus bacteria (Streptococcus sp.), And Escherichia coli (E.coli) with at least one selected from the group consisting of A compound characterized by exhibiting antimicrobial activity against the strain. 제 4 항에 있어서, 상기 스타필로코커스균은 메티실린 내성 스타필로코커스 아우레우스(Methicillin resistant Staphylococcus aureus; MRSA)인 것을 특징으로 하는 화합물.The compound of claim 4, wherein the Staphylococcus bacterium is Methicillin resistant Staphylococcus aureus (MRSA). 제 1 항의 화합물을 유효성분으로 포함하는 것을 특징으로 하는 항균제 조성물.An antimicrobial composition comprising the compound of claim 1 as an active ingredient. 제 6 항에 있어서, 상기 조성물이 스타필로코커스균(Staphylococcus sp.), 바실러스균(Bacillus sp.), 스트렙토코커스균(Streptococcus sp.) 및 대장균(E. coli)으로 이루어진 군으로부터 선택된 1종 이상의 균주에 대하여 항균 활성을 나타내는 것을 특징으로 하는 항균제 조성물.The method of claim 6, wherein the composition is one or more selected from the group consisting of Staphylococcus sp., Bacillus sp., Streptococcus sp., And E. coli . An antimicrobial composition comprising an antimicrobial activity against a strain.
KR1020090049627A 2009-06-04 2009-06-04 Antibacterial compounds from Dryopteris crassirhizoma and composition containing thereof KR101104388B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020090049627A KR101104388B1 (en) 2009-06-04 2009-06-04 Antibacterial compounds from Dryopteris crassirhizoma and composition containing thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020090049627A KR101104388B1 (en) 2009-06-04 2009-06-04 Antibacterial compounds from Dryopteris crassirhizoma and composition containing thereof

Publications (2)

Publication Number Publication Date
KR20100130885A true KR20100130885A (en) 2010-12-14
KR101104388B1 KR101104388B1 (en) 2012-01-17

Family

ID=43507078

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020090049627A KR101104388B1 (en) 2009-06-04 2009-06-04 Antibacterial compounds from Dryopteris crassirhizoma and composition containing thereof

Country Status (1)

Country Link
KR (1) KR101104388B1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107837247A (en) * 2017-08-09 2018-03-27 广东药科大学 Dryopteris fragrans phloroglucinol compound flavaspidic acid BB and its antibacterial applications
CN111269105A (en) * 2020-02-25 2020-06-12 广东药科大学 Compound Disaspidin BB and application thereof in antibiosis

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101393008B1 (en) 2012-09-06 2014-05-12 주식회사 코리아나화장품 Skin external application containing compounds from extract of Dryopteris crassirhizoma with anti bacterial activity
KR20220115447A (en) 2021-02-10 2022-08-17 서울대학교산학협력단 Antiviral agent with inhibitory activitity on SARS-coronavirus-2 by phloroglucinol compounds from Dryopteris crassirhiza and compositions for treatment and prevention of COVID-19 containing the same as an active ingredient

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107837247A (en) * 2017-08-09 2018-03-27 广东药科大学 Dryopteris fragrans phloroglucinol compound flavaspidic acid BB and its antibacterial applications
WO2019028933A1 (en) * 2017-08-09 2019-02-14 广东药科大学 Dryopteris fragrans phloroglucinol compound flavaspidic acid bb and antibacterial application thereof
CN107837247B (en) * 2017-08-09 2020-06-05 广东药科大学 Dryopteris fragrans phloroglucinol compound yellow-sheep-maleic acid BB and antibacterial application thereof
CN111269105A (en) * 2020-02-25 2020-06-12 广东药科大学 Compound Disaspidin BB and application thereof in antibiosis

Also Published As

Publication number Publication date
KR101104388B1 (en) 2012-01-17

Similar Documents

Publication Publication Date Title
JP7487150B2 (en) Natural preservatives, antimicrobial agents, and compositions thereof
Trusheva et al. Bioactive constituents of Brazilian red propolis
Kumar et al. Antibacterial and antimutagenic activities of novel zerumbone analogues
US7429396B2 (en) Antifungal composition, its fungicidal effect on pathogenic dermatophytes, and process for inhibiting growth of fungi
KR101104388B1 (en) Antibacterial compounds from Dryopteris crassirhizoma and composition containing thereof
Ali et al. 4-epi-Pimaric acid: a phytomolecule as a potent antibacterial and anti-biofilm agent for oral cavity pathogens
Sharma et al. The potential of Leucosidea sericea against Propionibacterium acnes
KR20180065799A (en) A composition for anti-bacterial effect and anti-inflammation comprising unripe apple extracts and baicalin
JP2010043061A (en) Anti-helicobacter pylori agent
KR101211669B1 (en) Antimicrobial compounds from Scilla scilloides and composition containing thereof
KR102176710B1 (en) A cosmetic composition comprising fractions of extracts of flower of Forsythia koreana as an active ingredient
KR20130112322A (en) Antimicrobial activity and anti-inflammatory effect composition comprising extract of capsella species as an effective ingredient
Kayed et al. New epoxy megastigmane glucoside from Dactyloctenium aegyptium LP Beauv Wild (Crowfootgrass)
KR102367027B1 (en) Antimicrobial composition comprising Hydrangea petiolaris extracts or fractions thereof as effective component
KR102413553B1 (en) Coumarin compound and anti-bacterial use thereof
KR20150030823A (en) External skin preparation comprising ginsenoside F5
Kumar et al. Antimicrobial activity of the major isolates of mentha oil and derivatives of menthol
KR101129354B1 (en) Anti-Bacterial Composition Comprising Extract from Barks of Alnus pendula Matsum
EP1786820B1 (en) 9-(1',5'-dimethyl-1'-vinyl-4'-hexenyl)-4-hydroxy-7h-furo[3,2-g][1]benzopyran-7-one as antibacterial agent
KR100967541B1 (en) Antibacterial pharmaceutical composition comprising Aceriphyllum rossii extract and active compounds isolated from them
KR101634740B1 (en) A composition for anti-bacterial and pharmaceurical composition for preventing or treating respiratory disease comprising the same
KR101359668B1 (en) Antibacterial Composition Containing Sedum sarmentosum Extract
JPH107555A (en) Antimicrobial agent
JP7485325B2 (en) Antibacterial agents and antibacterial skin cosmetics
JP5718700B2 (en) New sesterterpene compound, antibacterial agent and topical skin preparation

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20151218

Year of fee payment: 5

FPAY Annual fee payment

Payment date: 20161228

Year of fee payment: 6

FPAY Annual fee payment

Payment date: 20180411

Year of fee payment: 7

FPAY Annual fee payment

Payment date: 20190121

Year of fee payment: 8