• Title/Summary/Keyword: sesquiterpenoid

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CHEMOPREVENTIVE EFFECTS OF XANTHORRHIZOL

  • Park, Kwang-Kyun;Chung, Won-Yoon;Kim, Hee-Ok;Kim, Hee-Kyong;Park, Min-Ah;Kim, Mi-Jeong;Sohn, Joon-Hyung
    • Proceedings of the Korean Society of Toxicology Conference
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    • 2001.05a
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    • pp.145-145
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    • 2001
  • Xanthorrhizol is a sesquiterpenoid isolated from Curcuma xanthorrhiza Roxb. (Zingiberaceae) that has been traditionally used in Indonesia for dietary and medicinal purposes. In our studies to evaluate the cancer chemopreventive potential, xanthorrhizol inhibited the mutagenesis induced by reactive oxygen species in Sa;monella typhimurium TA 102 in a dose-related manner and decreased significantly the incidence and the multiplicity of skin tumors initiated by 7, 12-dimethylbenz[$\alpha$]anthracene and promoted by 12-Ο-tetradecanoylphorbol-13-acetate at 19 weeks.(omitted)

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Tentative Identification of Ginseng Flavor Components by Capillary Gas Chromatography and Mass Spectrometry (모세관(毛細管) GC/MS에 의한 인삼향기성분(人蓼香氣成分)의 일차적(一次的) 동정(同定))

  • Park, Nae-Joung;Kim, Man-Wook
    • Applied Biological Chemistry
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    • v.27 no.4
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    • pp.259-263
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    • 1984
  • Volatile flavor components of raw ginseng were collected from the manufacturing process of ginseng extract. Flavor components were separated by capillary column chromatography using SE-54 stationary phase and individual components were identified by means of GC/MS. Twenty six compounds including monoterpenes, esters, ethers, and sesquiterpenoids were tentatively identified. Major flavor components characteristic to ginseng appeared to he sesqiterpenoids such as ${\alpha}-gurjunene,\;{\beta}-maaliene,\;{\alpha}-guaiene,\;{\beta}-patchoulene$, (-)aromadendrene, and ${\beta}-elemene$.

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Evaluation of Immunotoxicity of Shizukaol B Isolated from Chloranthus japonicus

  • Kwon, Soon-Woo;Kim, Young-Kook;Kim, Jee-Youn;Ryu, Hwa-Sun;Lee, Hong-Kyung;Kang, Jong-Soon;Kim, Hwan-Mook;Hong, Jin-Tae;Kim, Young-Soo;Han, Sang-Bae
    • Biomolecules & Therapeutics
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    • v.19 no.1
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    • pp.59-64
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    • 2011
  • Dimeric sesquiterpenoid shizukaol B (SKB) was isolated from Chloranthus japonicus Sieb. Except that SKB inhibited adhesion molecule expression in monocytes and endothelial cells, no more biological and pharmacological activity of SKB had been reported until now. In this study, we examined immunosuppressive activity of SKB. SKB strongly inhibited lipopolysaccharide (LPS)-induced B cell proliferation with $IC_{50}$ of 137 ng/ml, but slightly or not concanavalin A-induced T cell proliferation, LPS-induced macrophage NO production, and LPS-induced dendritic cell maturation. As a mechanism, SKB strongly induced apoptotic death of B cells, but not other cell types. These results suggested that SKB induced toxicity-mediated immunosuppression against B cells.

Cytotoxicity of Trichothecenes to Human Solid Tumor Cells in Vitro

  • Choi, Sang-Un;Choi, Eun-Jung;Kim, Kwang-Hee;Kim, Nam-Young;Kwon, Byung-Mog;Kim, Sung-Uk;Bok, Song-Hae;Lee, So-Young;Lee, Chong-Ock
    • Archives of Pharmacal Research
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    • v.19 no.1
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    • pp.6-11
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    • 1996
  • The trichothecenes are sesquiterpenoid mycotoxins characterized by the 12,13-epoxytrichothec-9-ene ring system. We have tested cytotoxicity of several naturally-occurring or synthesized trichothecenes against human solid tumor cell lines. Among them, trichothecin(I) and $4-\beta$-Acetoxy-12,13-epoxytrichothec-9-ene (trichodermin, II) exhibited highly cytotoxic activities. 4-.betha.-Hydroxy-12,13-epoxytrichothec-9-ene (trichodermol, III) and $4-\beta$-Methoxy-12,13-epoxytrichothec-9-ene (IV) had mild cytotoxicities. But 12,13-Epoxytrichothec-9-ene-4-one (V) and $4-\beta$-Hydroxy-12,13-epoxytrichothec-9-ene(VI) had no cytotoxicities up to 10 $\mug/ml$. And in the tested cell lines, HCT15 colon cancer cell line was the most sensitive to all tested trichothecenes.

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DNA Topoisomerases I and II Inhibitory Activity of Constituents Isolated from Juglans mandshurica

  • Li, Gao;Lee, Sun-Young;Lee, Kyeung-Seon;Lee, Sung-Won;Kim, Sang-Hyun;Lee, Seung-Ho;Lee, Chong-Soon;Woo, Mi-Hee;Son, Jong-Keun
    • Archives of Pharmacal Research
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    • v.26 no.6
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    • pp.466-470
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    • 2003
  • Nine diarylheptanoids (1-9), one triterpene (10), one sesquiterpenoid (11), one naphthoquinone (12), four tetralones (13-16), one naphthalene carboxylic acid glucoside (17) and six naphthalenyl glycosides (18-23) were isolated from the roots of Juglans mandshurica Maximowicz (Juglandaceae), and their structures determined from the chemical and spectral data. Here, we report the inhibitory effects, on the DNA topoisomerases I and II activities, of all these compounds. Compounds 10 and 23 showed more potent inhibitory effects, on the DNA topoisomerases I and II (94.0 and 86.0% inhibitions at the concentration of 5 $\mu$ g/mL, respectively), than the positive control compounds, camptothecin and etoposide.

Phytochemical constituents from the aerial parts of Salvia plebeia

  • Paje, Leo Adrianne;Lee, Hak-Dong;Choi, Jungwon;Kim, Juree;Kim, Ki Hyun;Yu, A Ram;Bae, Min-Jung;Lee, Sanghyun
    • Journal of Applied Biological Chemistry
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    • v.64 no.4
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    • pp.391-397
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    • 2021
  • Four compounds were isolated from Salvia plebeia aerial parts. Silica gel open column chromatography with a gradient elution system was used to isolate and purify these compounds. Nuclear magnetic resonance spectroscopy and mass spectroscopy were used for structural elucidation and identification, while electronic circular dichroism was used to confirm the absolute configuration. The structures were determined to be 𝛽-sitosterol (1), (-)-1S,5S,8S,10R-1-acetoxy-8-hydroxy-2-oxoeudesman-3,7(11)-dien-8,12-olide (2), ursolic acid (3), and N-methylhydroxylamine (4). Compounds 2 and 4 were isolated for the first time from this plant. Compound 2 was quantitatively analyzed via HPLC/UV. The results showed that the methanol extract of S. plebeia had a higher content of compound 2 (1.20 mg/g) than the ethanol extract (0.55 mg/g). This study could be used as a preliminary step in conducting HPLC/UV analysis of sesquiterpenoids in S. plebeia extract to assess their bioavailability and potency.

Identification of natural insecticidal compound in medicinal plants against diamondback moth (약초(藥草) 중에 존재(存在)하는 배추좀나방에 대한 천연살충성(天然殺蟲性) 물질(物質)의 동정(同定))

  • Chun, Jae-Chul;Kim, Sung-Eun;Kim, Jin-Cheol;Cho, Kwang-Yun
    • The Korean Journal of Pesticide Science
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    • v.3 no.1
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    • pp.13-19
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    • 1999
  • Insecticidal potentials of polar and non-polar tractions obtained from 84 medicinal plants were screened against five major agricultural insects. Based on the primary and secondary screening results, non-polar fraction of Atractylodes koreana Kitam. rhizomes was selected to isolate and identify an active compound effective to diamondback moth (Plutella xylostella L.) larvae. Counter-current distribution separation on the non-polar fraction and TLC and spectroscopic analyses (GC-MS and $^{1}H$- and $^{13}C$-NMR) revealed that molecular formula of the active compound was $C_{15}H_{22}O$ known as a sesquiterpenoid 4,11-selinadien-3-one (${\alpha}$-cyperone). However, ${\alpha}$-cyperone was not detected in the non-polar fractions that showed high insecticidal potential against the diamondback moth. Although ${\alpha}$-cyperone has been first identified from Cyperus rotundus, the compound did not occur in C. rotundus cultivated in Korea.

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Biosynthesis of Sesquiterpene in Hairy Root and Cell Suspension Cultures of Hyoscyamus muticus by Elicitation Using Rhizoctonia solani Extracts (Rhizoctonia solani 추출액 첨가에 의한 Hyoscyamus muticus의 현탁세포배양 및 모상근배양에서 Sesquiterpene 생합성)

  • 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.279-284
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    • 1997
  • The extracellular sesquiterpenoids were accumulated in cell and hairy root cultures of Hyoscyamus muticus by elicitation using extracts of Rhizoctonia solani. The vetispiradiene synthase (VS) which is the first committed step in biosynthetic pathway leading to formation of solavetivone, lubimin, and rishitin from isoprenoid intermediate farnesyl pyrophosphate was induced upon elicitation, whereas no sesquiterpenoids and VS activity were detected in both control cell and hairy root cultures. VS activity increased rapidly and reached its maximum 12 h in both cell and hairy root cultures upon elicitor treatment. VS activities were paralleled with the absolute levels of VS polypeptide(s). Interestingly, the profiles of sesquiterpenoid accumulation in hairy root cultures were different from those in cell cultures. The hairy root culture seemed to fail to metabolize solavetivone further to lubimin.

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The Structural Characteristics of the Active Ingredients in Several 'Hot and Warm' Herbal Medicine (한약(韓藥)의 온열성약(溫熱性藥)의 성분(成分)과 화학적(化學的) 특성(特性)에 관(關)한 연구(硏究))

  • Shin, Joon-Shik;Ahn, Duk-Kyun;Park, Ho-Koon
    • The Journal of Korean Medicine
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    • v.20 no.1 s.37
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    • pp.1-10
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    • 1999
  • 한약(韓藥)의 효능(效能)은 약성(藥性)에 의해 분류(分類)되고 질병(疾病)을 치료(治療)하며 예방(豫防)하는 작용(作用)을 한다. 그러나 약성(藥性) 이론(理論)의 문헌(文獻)과 임상연구(臨床硏究)는 비교적 많지만 상대적으로 실험연구(實驗硏究)는 일부분에 불과하여 효능(效能)을 입증(立證)하는데 어려움이 많다. 이에 저자(著者)는 온열성약(溫熱性藥)들이 지니고 있는 유효(有效) 성분(成分)들을 조사(調査)하고 이 온열성약(溫熱性藥)에 함유(含有)되어 있는 유효(有效) 성분(成分)들의 구조적(構造的)인 특성(特性)과 화학적(化學的)인 공통점(共通點)을 찾아 온열성약(溫熱性藥)의 분류(分類)에 대한 일반적(一般的)인 기준(基準)을 제시(提示)하고자 하였다. 그 결과 각각의 열성약(熱性藥)과 온성약(溫性藥)들이 함유(含有)하고 있는 유효(有效) 성분(成分)간의 구조적(構造的)인 공통점(共通點)을 찾아내었으며 구조적(構造的)인 공통점(共通點)으로부터 다음과 같은 결론(結論)을 얻었다. 1. 열성약(熱性藥) 중에서 강(强)한 독성(毒性)을 나타내는 부자(附子)와 초오(草烏)의 효능을 나타내는 유효 성분(成分)들은 C19-diterpenoid alkaloid과 C20-diterpenoid alkaloid 계열의 구조(構造)를 지닌 화합물들로 구성(構成)되어 있다. 이 디테르펜 알카로이드(diterpene alkaloid)들의 경우 고리의 구조(構造)가 aconitane(1), hetisan(16)과 7,20-cycloveatchane(17)의 기본골격(基本骨格)을 지니고 있으며, 이 두 가지 기본구조(基本構造)의 공통점(共通點)은 A 고리에 질소를 포함한 2-azabicyclo-[3.3.1]-nonanyl의 부분구조를 갖고 있으며, 이 부분 구조는 자연계에 존재하는 tropane alkaloid들의 기본구조(基本構造)와 유사하다. Tropane alkaloid들은 중추신경계에 작용하는 약물들로 알려져 있으며, tropane alkaloid는 일반적으로 anatoxin a(171)와 같이 강(强)한 독성(毒性)을 나타내며, 부자(附子)와 초오(草烏)가 지니고 있는 강한 독성(毒性)은 바로 2-azabicyclo-[3.3.1]-nonanyl 구조(構造)에 기인하는 것으로 추정할 수 있다. 2. 육계(肉桂)에 주성분으로 함유(含有)되어 있는 cinncassiol(47) 화합물(化合物)들은 분자 내에 bicyclo-[4.3.0]-nonanyl과 bicyclo-[3.3.0]-octanyl의 기본 혹은 부분 구조를 지니고 있다. 3. Cinncassiol(47) 화합물(化合物)들은 강(强)한 항균력(抗菌力)을 보이고 있는데, cinncassiol(47) 화합물들이 지니고 있는 구조적인 특성인 bicyclo-[4.3.0]-nonanyl과 bicyclo-[3.3.0]-octanyl의 기본 혹은 부분 고리구조는 sesquiterpenoid 화합물(化合物)들과 diterpenoid 화합물(化合物)들 중에서 많이 발견되며, 이러한 구조(構造)를 지니고 있는 sesquiterpenoid 화합물(化合物)과 diterpenoid 화합물(化合物)들도 좋은 항균력(抗菌力)을 보이고 있다. 이러한 공통(共通)된 구조상(構造上)의 유사점(類似點)이 항균력(抗菌力)을 나타내는 지표로서 활용 가능성이 기대된다. 4. 온성약(溫性藥)의 경우, 백지(白芷)의 coumarin(39) 화합물(化合物)들과 furocoumarin(61) 화합물(化合物)들, 건량(乾量)의 gingerol(87), shogaol(93), gingerdiol(95) 등과 capsaicin(102), 마황(麻黃)의 ephedrine(124) 계렬(系列) 화합물(化合物)들, 세신(細辛)의 methyleugenol(136)과 asaricin(137)의 구조(構造)에서 발견(發見)할 수 있는 공통적(共通的)인 요소는 phenolic 또는 methoxyphenyl의 공통구조를 지니고 있다. 온성약(溫性藥)의 유효성분들은 공통적으로 phenolic aromatic 화합물(化合物)을 함유(含有)하고 있다. 따라서, 열성약(熱性藥)과 온성약(溫性藥)은 주성분(主成分)들의 분포(分布)가 각기 다르며, 독성(毒性)을 나타내는 열성약(熱性藥)은 2-azabicyclo-[3.3.1]-nonanyl 구조(構造)를 지니고 있고, 육계(肉桂)와 같은 항균력(抗菌力)을 지니는 약물(藥物)은 bicyclo-[3.3.0]-octanyl 또는 bicyclo-[4.3.0]-nonanyl의 구조(構造)를 지닌다. 백지(白芷), 마황(麻黃), 세신(細辛) 등에서 볼 수 있듯이 온성약(溫性藥)은 benzene 구조(構造)를 함유(含有)하는 phenolic aromatic 화합물(化合物)들이 주종을 이룬다.

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Comparison of Essential Oil Composition of Artemisia iwayomogi and Artemisia capillaris (더위지기와 사철쑥의 정유성분 조성 비교)

  • Hong, Chul-Un
    • Applied Biological Chemistry
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    • v.47 no.1
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    • pp.124-129
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    • 2004
  • The composition of essential oils isolated from the aerial parts of Artemisia iwayomogi Kitamura and Artemisia capillaris Thunberg collected from two diffenent cultivation area, respectively, was analyzed by GC and GC-MS. Sixty components were identified in oils from A. iwayomogi. The major components of A. iwayomogi oil collected from one area (Sample A) were iso-pinocamphone (31.64%), 1,8-cineo1e (21.55%), ${\beta}-pinene$ (4.46%), pinocarvone (3.72%), myrtenal (3.42%) and trans-pinocarve1 (3.14%), and the major components of the oil from the other area (Sample B) were camphor (26.99%), 1,8-cineo1e (21.55%), ${\alpha}-terpineol$ (7.63%), borneol (4.10%), camphene (3.97%) and artemisia ketone (3.84%). Eighty components were identified in oils from A. capillaris. The major components were capillene $(26.01{\sim}30.31%)$, ${\beta}-pinene(8.55{\sim}18.38%)$, ${\beta}-caryophyllene(8.80{\sim}13.70%)$, ${\beta}-himachalene(1.67{\sim}5.57%)$, $cis,trans- {\alpha}-farnesene(2.10{\sim}7.38%)$ and germacrene D $(2.27{\sim}5.46%)$ and there was no difference in oil composition of A. capillaris between two cultivation area.