• Title/Summary/Keyword: sesquiterpenes

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Recent Studies on the Chemical Constituents of Korean Ginseng (Panax ginseng C. A. Meyer) (고려인삼의 화학성분에 관한 고찰)

  • 박종대
    • Journal of Ginseng Research
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    • v.20 no.4
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    • pp.389-415
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    • 1996
  • Panax ginseng C.A. Meyer(Araliaceae) has been traditionally used as an expensive and precious medicine in oriental countries for more than 5, 000 years. Ginseng saponin isolated from the root of Panax ginseng have been regarded as the main effective components responsible for the pharmacological and biological activities. Such as antiaging effects. antidiabetic effects anticancer effects. Protection against physical and chemical stress. Analgesic and antipyretic effects. Effects on the central nervous system, tranquilizing action and others. Thirty kinds of ginsenosides have been so far isolated from ginseng saponin and their chemical structures have been elucidated since 1960's. Among which protopanaxadiol type is 19 kinds. protopanaxatriol type. 10 kinds and oleanane type, one. Since ginsenosides are generally labile under acidic conditions ordinary acid hydrolysis is always accompanied by many side reactions, such as epimerization. hydroxylation and cyclization of side chain of the sapogenins Especially. it is well known that C-20 glycosyl linkage of ginsenoside was hydrolysed on heating with acetic acid to give an equilibrated mixture of 20(S) and 20(R) epimers. And also, the chemical transformations of the secondary metabolites have appeared during the steaming process to prepare red ginseng. Indicating demalonylation of malonyl ginsenosides, elimination of glycosyl residue at C-20 and isomerization of hydroxyl configuration at C-20. But these studies have not provided a comprehensive picture in explaning how these ginsenosides showed val'iotas pharmacological activities of ginseng. Though some of them have been involved in the mechanism of pharmacological actions. Recently, non-saponin components have received a great deal of attention for their antioxidant, anticancer antidiabetic, immunomodulating. anticomplementary activities and so on. To meet the demand for such wide applications, studies on the non-saponin components play an important role in providing a good evidence of pharmacological and biol ogical activities. Among the non-saponin constituents of Korean ginseng, polyacetylenes, phenols. Sesquiterpenes, alkaloids. polysaccharides oligosaccharides, oligopeptides and aminoglycosides together with ginsenosides of terrestrial part are mainly described.

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Induction of Sesquiterpene Cyclase During Integrated Extraction of Sesquiterpenes from Hairy Root Cultures of Hyoscyamus muticus (Hyoscyamus muticus의 모상근배양으로부터 Sesquiterpene 화합물의 Intergration 추출시 Sesquiterpene Cyclase의 유도)

  • BACK, Kyoungwhan;SHIN, Dong Hyun;KIM, Kil Ung;De HAAS, Cynthia R.;CHAPPELL, Joseph;CURTIS Wayne R.
    • Korean Journal of Plant Tissue Culture
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    • v.24 no.5
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    • pp.273-277
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    • 1997
  • The sesquiterpene cyclase (SC) was induced and its products were accumulated in the culture media of Hyoscyamus muticus hairy roots by addition of Rhizoctonia solani extracts. The cumulative production of solavetivone was nearly doubled by integrated extraction of the products from the media during the 24 h accumulation period. Western blots with monoclonal antibodies against SC show that the enzyme levels are the same for both extracted and non-extracted cultures. SC activities measured in vitro with radioactive substrate are not significantly different. These results suggest that productivity is controlled by substrate availability within the terpenoid pathway, and feedback regulation precedes the branch-point enzyme sesquiterpene cyclase.

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Isolation of Sesquiterpene Synthase Homolog from Panax ginseng C.A. Meyer

  • Khorolragchaa, Altanzul;Parvin, Shohana;Shim, Ju-Sun;Kim, Yu-Jin;Lee, Ok-Ran;In, Jun-Gyo;Kim, Yeon-Ju;Kim, Se-Young;Yang, Deok-Chun
    • Journal of Ginseng Research
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    • v.34 no.1
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    • pp.17-22
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    • 2010
  • Sesquiterpenes are found naturally in plants and insects as defensive agents or pheromones. They are produced in the cytosolic acetate/mevalonate pathway for isoprenoid biosynthesis. The inducible sesquiterpene synthases (STS), which are responsible for the transformation of the precursor farnesyl diphosphate, appear to generate very few olefinic products that are converted to biologically active metabolites. In this study, we isolated the STS gene from Panax ginseng C.A. Meyer, designated PgSTS, and investigated the correlation between its expression and various abiotic stresses using real-time PCR. PgSTS cDNA was observed to be 1,883 nucleotides long with an open reading frame of 1,707 bp, encoding a protein of 568 amino acids. The molecular mass of the mature protein was determined to be 65.5 kDa, with a predicted isoelectric point of 5.98. A GenBank BlastX search revealed the deduced amino acid sequence of PgSTS to be homologous to STS from other plants, with the highest similarity to an STS from Lycopersicon hirsutum (55% identity, 51% similarity). Real-time PCR analysis showed that different abiotic stresses triggered significant induction of PgSTS expression at different time points.

Extraction, Component Analysis and Antibacterail Activity of Panax ginseng Absolute Essential Oil (인삼 앱솔루트 정유의 추출, 성분 분석 및 항균 활성)

  • Han, Sang-Kil;Park, Soo-Nam
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.34 no.1
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    • pp.67-73
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    • 2008
  • Interests in natural products have been gradually increasing as well-being era has arrived. Panax ginseng was chosen since it represents Korean traditional medicine as its effect on many age-related symptoms. Panax ginseng absolute essential oil was prepared and analyzed for its main components. Ginseng absolute oil was extracted from Panax ginseng using organic solvent of hexane and ethanol with the yield of 0.146%. The oil was analyzed by GC-MS and main components are sesquiterpenes such as neoclovene, panasinsene, and calarene and more than 110 components were identified from it. The oil was tested for antibacterial activity against general bacteria(E. Coli, S. aureus and P. aeruginosa), yeast, acne germ(Propionibacterium acne) and dandruff germ(Pityrosporum ovale). Panox ginseng absolute essential oil showed the prominent antibacterial activity against Propionibacterium acnes ACCC 6919.

Inhibitory Effects of the Rhizome Extract of Atractylodes japonica on the Proliferation of Human Tumor Cell Lines (백출 추출물의 암세포증식 저해 효과)

  • Lee, Sung-Ok;Seo, Jee-Hee;Lee, Jung-Won;Yoo, Mi-Young;Kwon, Jee-Woong;Choi, Sang-Un;Kang, Jong-Seong;Kwon, Dae-Young;Kim, Young-Kyoon;Kim, Young-Sup;Ryu, Shi-Yong
    • Korean Journal of Pharmacognosy
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    • v.36 no.3 s.142
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    • pp.201-204
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    • 2005
  • The rhizome extract of Atractylodes japonica Koidzumi(Compositae) exhibited a particular inhibition on the proliferation of cultured human tumor cell lines, in vitro. Thus, the intensive phytichemical investigation of the MeOH extract of Atractylodes japonica have been conducted by the way of activity-guided purification. The repeated column chromatographic separation of the n-hexane soluble part of extract resulted in the isolation of four sesquiterpenes (1-4) and a polyacetylene component (5). Chemical structures of them were identified as atractylon (1), atractylenolide Ⅰ(2), atractylenolide Ⅲ(3), eudesma-4(15),7(11)-dien-8-one (4) and 1,3-diacetyl-atractylodiol (5) by spectroscopic means. Among the isolates, compound 2-4 were shown to give moderate inhibitory effect in a dose dependent manner on the proliferation of cultured human tumor cell lines such as A549 (non small cell lung), SK-OV-3 (ovary), SK-MEL-2 (melanoma), XF498 (central nerve system) and HCT 15(colon), respectively.

Comparative Phytochemical Profiling of Methanolic Extracts of Different Parts of White Dandelion (Taraxacum coreanum) using Hybrid Ion-mobility Q-TOF MS

  • Hyemi Jang;Mira Choi;Eunmi Lee;Kyoung-Soon Jang
    • Mass Spectrometry Letters
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    • v.15 no.2
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    • pp.95-106
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    • 2024
  • Taraxacum coreanum, known as the native Korean white dandelion, has been historically used in traditional medicine due to its various therapeutic properties. However, the specific benefits and mechanisms of white dandelion in alleviating particular symptoms or diseases remain uncertain due to the complexity of its phytochemical profile. In this study, we aimed to elucidate the phytochemical profiles of methanolic extracts of different parts of the white dandelion (flower, leaf, stem, and root) using hybrid ion-mobility Q-TOF MS. Using the trapped ion mobility-based PASEF technique, 3715 and 2114 molecular features with MS2 fragments were obtained in positive and negative ion modes, respectively, and then a total of 360 and 156 phytochemical compounds were annotated by matching with a reference spectral library in positive and negative ion modes, respectively. Subsequent feature-based molecular networking analysis revealed the phytochemical differences across the four different parts of the white dandelion. Our findings indicated that the methanolic extracts contained various bioactive compounds, including lipids, flavonoids, phenolic acids, and sesquiterpenes. In particular, lipids such as linoleic acids, lysophosphatidylcholines, and sesquiterpenoids were predominantly present in the leaf, while flavonoid glycosides and lysophosphoethanolamines were notably enriched in the flower. An assessment of the total phenolic content (TPC) and total flavonoid content (TFC) of the methanolic extracts revealed that the majority of phytochemicals were concentrated in the flower. Interestingly, despite the root extract displaying the lowest TPC and TFC values, it exhibited the highest radical scavenging rate when normalized to TPC and TFC, suggesting a potent antioxidant effect. These findings and further investigations into the biological activities and medicinal potential of the identified compounds, particularly those exclusive to specific plant parts, may contribute to the development of novel therapeutic agents derived from white dandelion.

Effects of Drying Conditions on the Profile of Volatile Terpenoid and Colour of Schizandra Fruit(Schizandra Chinensis fructus) (건조 조건이 오미자의 휘발성 terpene류 및 색도에 미치는 영향)

  • Kim, Yun-Je;Lee, Young-Guen;Choi, Young-Whan;Kim, Yong-Chul
    • Journal of Life Science
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    • v.18 no.8
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    • pp.1066-1071
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    • 2008
  • Schizandra fruit (Schizandra chinensis fructus) were dried by three processes, $50^{\circ}C$ (50HAD), $70^{\circ}C$ hot air (70HAD) and freeze drying process (FRD). Terpenoid were collected by SDE(Simultaneous Steam Distillation-Extraction) and followed by GC-MSD analysis. Also colour profile of each dried samples were measured by Hunter colorimeter. From fresh schizandra fruit, were detected 15 kinds of monoterpene, 28 kinds of sesquiterpene and 7 kinds of terpene alcohol. Myrcene(56.97 ${\mu}g/g$) and ${\gamma}$-terpinene(58.49 ${\mu}g/g$) were the major monoterpenes, ${\beta}$-elemene(120.16 ${\mu}g/g$), ${\alpha}$-bergamotene (103.45 ${\mu}g/g$), ${\gamma}$-selinene (75.97 ${\mu}g/g$), ${\beta}$-cubebene(66.69 ${\mu}g/g$), aristolene (51.25 ${\mu}g/g$) and ${\alpha}$-ylangene(28.06 ${\mu}g/g$) were the sesquiterpenes, and T-muurolol (96.45 ${\mu}g/g$) and terpinen-4-ol(46.02 ${\mu}g/g$) were the terpene alcohols. The dried samples lost more than half of terpenoid content of fresh schizandra fruit during early stage of drying process, and then the level of terpenoid content was not significantly changed. The content of sesquiterpenes appeared to increase until 6 day of FRD. The amount of residual terpene alcohols contained in schizandra fruit dried by FRD was more than those remained after drying by other processes, and schizandra fruit dried by 70HAD exhibited the least residual terpene alcohols. Brightness parameter $L^{\ast}$ decreased with the rise in the level of drying temperature, to which redness parameter $a^{\ast}$ and yellowness $b^{\ast}$ appeared to be similar.

Analysis of Terpenoids as Volatile Compound Released During the Drying Process of Cryptomeria japonica (삼나무 건조 중 발생하는 휘발성 유기화합물 Terpenoids의 분석)

  • Lee, Su-Yeon;Gwak, Ki-Seob;Kim, Seon-Hong;Lee, Jun-Jae;Yeo, Hwan-Myeong;Choi, In-Gyu
    • Journal of the Korean Wood Science and Technology
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    • v.38 no.3
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    • pp.242-250
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    • 2010
  • The aim of this study was to investigate the terpenoids of Total Volatile Organic Compounds (VOCs) released during drying of Cryptomeria japonica using the thermal extractor (TE). Considering the drying process of C. japonica, temperatures of TE were set at $27^{\circ}C$, $60^{\circ}C$, $80^{\circ}C$, $100^{\circ}C$, and $120^{\circ}C$, respectively. As the result, the emission factors of VOCs and terpenoids were increased as temperature increased. The amount of terpenoids included in VOCs emission factors were 87.5%, 81.6%, 83.6%, 90.1%, and 97.3% depending on above temperatures, respectively. Especially at$100^{\circ}C$ and $120^{\circ}C$, the amount of terpenoids were measured more than 90%. ${\delta}$-cadinene was the highest yield at each temperature and 32 types of terpenoids were collected. Emitted terpenoids were classified into the sesquiterpene group which consists of 15 carbon sources. These 32 sesquiterpenes were used for determining the useful bioactivity such as antifungal activity by the agar dilution. As the result, they showed the antifungal activity against Trichophyton rubrum, Trichophyton mentagrophytes, Microsporum gypseum. The 5,000 ppm concentration of terpenoids showed a strong activity with 100% against the 3 fungi. At the 1,000 ppm concentration of terpenoids, the antifungal activities against three fungi were 95.2%, 98.7%, and 97.3%, and their activities were a little inhibited at 100 ppm concentration.

A Study on the analysis method and composition characteristics of organic materials in the pottery excavated at the palace site in Yongjangseong Fortress, Jindo (진도 용장성 왕궁지 출토 도기호 내부 유기물의 분석법과 성분 특성 연구)

  • YUN Eunyoung;YU Jia;KIM Kyuho
    • Korean Journal of Heritage: History & Science
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    • v.56 no.3
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    • pp.158-171
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    • 2023
  • Pottery filled with organic materials was excavated from the G-2 building site of Yongjangseong Fortress, Jingo, a relic of the Goryeo Dynasty. In this study, the characteristics of organic material were confirmed by a scientific analysis of organic material in pottery found at the palace in Yongjangseong, Jindo. In addition, it was intended to review the analysis method to identify the natural resin and to secure characteristic components(biomarkers) for each natural resin and use them as basic data in the future. The organic materials in the pottery were analyzed using attenuated total reflectance Fourier-transformed infrared spectroscopy(ATR-FTIR) and gas chromatography mass spectrometry(GC-MS). The infrared spectral characteristics were estimated to be natural resin, and biomarkers of organic materials were identified as sesquiterpene-based compounds(C15H24, MW 204) and derivatives. The lacquer(T.vemicifluum) is composed mainly of alkenes, alkanes, and catechol. Pine resin(P.densiflora), on the other hand, is primarily composed of diterpenoid(abietic acid, pimaric acid) and Whangchil(yellow lacquer) is identified to have sesquiterpenes(such as selinene, muurolene, calamenene) as its main components. So, the organic material in the pottery can be identified as Whangchil by comparing their compounds with modern resin materials from Dendropanax. morbifera that correspond with the results. Whangchil, which is exuded from the Dendropanax. morbifera, has been used as a natural coating materials since ancient times, and it has been confirmed that the characteristic components are well preserved even 700 years later. It can be assumed that the interior Whangchil was stored not for use as a coating, but rather for ritual purposes when the building was constructed, because the pottery was found near the cornerstone. Furthermore, based on simplified sample preparation using pyrolysis-gas chromatography mass spectrometry(Py-GC-MS), the thermal decomposition products were found to be similar to the characteristic components, suggesting that this method can be applied to the identification of natural resins used in historic artifacts.

Investigation of Active Antifungal Compounds of Essential Oil from Chamaecyparis obtusa Against Dermatophytes, Microsporum canis and Trichophyton Mentagrophytes (피부사상균 Microsporum canis 및 Trichophyton mentagrophytes에 대한 편백정유의 항진균활성물질 탐색)

  • Park, Mi-Jin;Lee, Soo-Min;Gwak, Ki-Seob;Jeung, Eui-Bae;Chang, Je-Won;Choi, In-Gyu
    • Journal of the Korean Wood Science and Technology
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    • v.33 no.3 s.131
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    • pp.72-78
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    • 2005
  • The present study was conducted to evaluate the application of Chamaecyparis obtusa and to investigate potential utilization of essential oil from C. obtusa as plant-based medicine. The antifungal activity of essential oil from leaves and twigs of C. obtusa (Sieb. Et Zucc) was determined and the major components of active fractions against Microsporum canis (KCTC6591) and Trichophyton mentagrophytes (KCTC6077) were identified by GC/MS analysis. In treatment of essential oil from C. obtusa, the strain M. canis was more resistant than the other, T. mentagrophytes. In the agar diffusion assay, essential oil from C. obtusa inhibited hyphal growth of M. canis and T. mentagrophytes at the concentration of more than 5,000 ppm. The zones named B and C in the TLC assay of essential oil from C. obtusa showed antifungal activities. Among four sub-fractions of n-hexane extract from B and C zones, named as B-1, B-2, C-1 and C-2, the C-2 showed the highest antifungal activity. Instrumental GC/MS analysis for sub-fractions showed that a major component of C-1 was ${\alpha}$-terpineol as terpene alcohol, while C-2 contained sesquiterpenes such as elemol, cedrol and eudesmol.