• 제목/요약/키워드: semisynthesis

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Discovery, semisynthesis, biological activities, and metabolism of ocotillol-type saponins

  • Liu, Juan;Xu, Yangrong;Yang, Jingjing;Wang, Wenzhi;Zhang, Jianqiang;Zhang, Renmei;Meng, Qingguo
    • Journal of Ginseng Research
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    • 제41권3호
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    • pp.373-378
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    • 2017
  • Ocotillol-type saponins are one kind of tetracyclic triterpenoids, sharing a tetrahydrofuran ring. Natural ocotillol-type saponins have been discovered in Panax quinquefolius L., Panax japonicus, Hana mina, and Vietnamese ginseng. In recent years, the semisynthesis of 20(S/R)-ocotillol-type saponins has been reported. The biological activities of ocotillol-type saponins include neuroprotective effect, antimyocardial ischemia, antiinflammatory, antibacterial, and antitumor activities. Owing to their chemical structure, pharmacological actions, and the stereoselective activity on antimyocardial ischemia, ocotillol-type saponins are subjected to extensive consideration. In this review, we sum up the discovery, semisynthesis, biological activities, and metabolism of ocotillol-type saponins.

Antigenicity Study of CFA-001, cefazolin, a cephalosperin Derivative Produced by an :Enzymatic Semisynthesis

  • Park, Jong-Il;Jeong, Tae-Cheon;Kim, Hyoung-Chin;Han, Sang-Seop;Roh, Jung-Koo;Kim, Jeong-Hwan;Jeon, Yeong-Joong;Kim, Dal-Hyun;Kim, Je-Hak;Park, Kwan-Ha
    • Biomolecules & Therapeutics
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    • 제5권1호
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    • pp.48-52
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    • 1997
  • The antigenic potential of CFA-001, cefazolin, a cephalosporin derivative produced by an enzy-matic semisynthesis, was determined in Hartley guinea pigs. A battery of tests employed consisted of active systemic anaphylaxis (ASA), passive cutaneous anaphylaxis (PCA), and indirect hemagglutination test (IHA). The results were as follows: 1) In ASA, no signs attributable to anaphylaxis was observed in guinea pigs sensitized with CFA-001, whereas OVA-sensitized animals induced severe anaphylactic symptoms; 2) guinea pigs did not produce antibodies against CFA-001 when sensitized with or without Freund's complete adjuvant (FCA) in homologous PCA tests. Meanwhile, antibodies against ovalbumin (OVA) were clearly detected; 3) No CFA-001-specific hemagglutination was observed in the IHA using sera obtained from CFA-001- sensitized guinea pigs. These results suggest that CFA-001 has no antigenicity potential in guinea pigs.

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진세노사이드 $Rh_2$의 방향선택적 합성 (Regioselective Synthesis of Ginsenoside $Rh_2$)

  • 신명희;정지형;장은하;임광식
    • 약학회지
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    • 제45권4호
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    • pp.328-333
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    • 2001
  • Ginsenoside Rh$_2$, a minor glycoside constituent of the red ginseng is known as an unique antitumor compound. Several attempts to prepare it in a large scale including semisynthesis from betulafolientriol, an 3-epimer of 20(S)-protopanaxadiol, has been reported. We have previously reported a synthesis of ginsenoside Rh$_2$from 20(S)-protopanaxadiol obtained by alkaline hydrolysis of total ginsenoside. The regioselective synthesis of this compound was achieved by protection of 12-OH group.

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주목 세포배양에 의한 Taxol 생산 : 유럽 주목의 세포배양에서 추출한 Baccatin III로부터 Taxol의 반합성 (Taxol Production in Taxus spp. Cell Culture : Semisynthesis of Taxol from Baccatin III in Cell Cultures of Taxus baccta Pendula)

  • 전정욱;조병관
    • KSBB Journal
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    • 제11권3호
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    • pp.263-269
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    • 1996
  • 유럽 주목(Taxus baccata Pendula) 의 세포배양에 서 추출한 taxol 전구체 baccatin ill를 이용하여 항암제 taxol을 반합성할 수 있었다. 유럽주목의 캘러 스배양과 현탁배양 모두에셔 baccatin ill의 생성을 확인할 수 있었으며 함량은 건조중량 기준으로 평균 0.015%(w/w)에 달하였다. Taxol의 반합성은 세포 배양에서 생성된 baccatin ill에 taxol side chain을 합성시킴으로서 가능하였다. Taxol side chain을 합 성하기 위하여 (S)-(+)-phenylglycine로부터 (-) - -N-(S)-2-hydroxy-l-phenyl ethyl)benzamide를 합성하였고 다음 단계로 (-)-N-(lS,2S)-2-hy­d droxy-l-phenyl-3-butenyl) benzamide를 합성하 였고 최종적으로 산화과정을 거쳐 taxol side chain 인 (2R,3S) - (-) -2-(1-ethoxyethoxy)-3-phenyl-3 (phenylmethanamido) propanoic acid를 얻을 수 있었다. 이러한 반합성 과정을 통하여 0.0002 % 수준의 taxol 및 0.0005 %의 관련 taxane을 합성하였다. 이와 같이 주목 세포배양을 이용한 taxol 반합성 방법은 기존의 주목 잎에서 추출한 baccatin ill를 이용하는 방법에 비하여 충분한 경제성이 있을 수 있으며 이에 따라 taxo!의 새로운 공급원의 역할 및 기타 여러 종류의 taxol 유사체의 효율적인 이용 등 앞으로 기대 효과가 크다고 본다.

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Current status of natural product industry and its commercial application to health functional foods

  • Park, Jong Dae
    • 한국자원식물학회:학술대회논문집
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    • 한국자원식물학회 2018년도 추계학술대회
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    • pp.21-21
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    • 2018
  • Natural product substances have historically served as the most significant also be prepared by source of new leads for pharmaceutical development. They can chemical synthesis(both semisynthesis and total synthesis) and have played a important role in the field of organic chemistry by providing synthetic targets. Rcently, they have also been extended for commercial purpose to refer to medicinal products, health functional foods, dietary supplements and cosmetics from natural sources. A large number of currently prescribed drugs have been either directly derived from or inspired by natural products. However, with the advent of robotics, bioinformatics, high throughput screening(HTS), molecular biology-biotechnology, combinatorial chemistry, in silico(molecular modeling) and other methodologies, the pharmaceutical industry has largely moved away from plant derived natural products as a source for leads and prospective drug candidates. The strategy for natural prduct industry is now changing from drug approaches to health foods by identifying effective natural products as preparations. In Korea, a lot of development of natural product based drugs have been done, but very few on health functional foods. The concept of natural product based health foods is not active components as lead compounds but standardized extracts or preparation mixed with other medicinal plants. The representative material has been recently known to be a standardized ginseng extract "Ginsana G 115" developed by Swiss Pharmaton company. The purpose of this presentation is to underline how natural products research continues to make significant contributions in the domain of discovery and development of new health functional foods. It is proposed to present the development of high value added health food or health functional foods through scientific investigation on efficacy and standardization of new materials form natural products.

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주목 현탁세포배양을 이용한 10-deacetylbaccatin III 생산 (Production of 10-deacetylbaccatin III in Taxus cuspidata Suspension Cell Culture)

  • 이규화;김동일
    • KSBB Journal
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    • 제14권6호
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    • pp.665-671
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    • 1999
  • 본 연구에서는 식물 유래의 항암제인 taxol을 생산하는 주목세포의 현탁배양을 통하여 taxol 반합성의 전구체인 10-deacetylbaccatin III(10-DAB)의 생산을 증대시키고자 하였다. 이 차대사산물의 생산이 세포생장과 관련이 있으므로 세포생장이 우수한 배지를 선택하기 위한 실험을 수행하였고, SH 배지에서 가장 우수한 세포생장이 관찰되었다. 또한 선택된 SH 배지에서 우수한 세포생장과 10-DAB 생산을 얻기 위해 초기 접종농도와 당농도의 변화를 관찰하였다. 초기 접종농도와 당농도가 낮을수록 세포생장이 빠르며, 낮은 초기 당농도와 초기 접종농도 6 g/L FCW 이었을 때 10-DAB의 생산이 우수하였다. 생산성을 높이기 위한 고농도 세포생장과 배지로의 10-DAB 분비를 목적으로 perfusion culture를 도입하였다. 고농도 당을 첨가한 배지로 perfusion을 수행한 결과 배양 후반까지 세포생장이 가능하였고, FCW/DCW ratio가 감소되어 대조구의 2.5배인 34.67 g/L의 높은 세포농도를 얻을 수 있었다. 10-DAB의 생산은 perfusion 시작후 10일 동안은 배지로 배출된 양이 세포내보다 높았다.

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