• Title/Summary/Keyword: Monoterpenoid

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Synthesis and in vitro Cytotoxicity Monoterpenoid as New Antitumor Agents (Monoterpenoid계의 새로운 항암제 합성 및 In vitro 세포독성 평가)

  • 이민정;김대근;백형근;이강노;정규혁
    • Biomolecules & Therapeutics
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    • v.9 no.3
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    • pp.143-155
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    • 2001
  • Many attention has been focused on developing new chemotherapeutic agents for a treatment of cancer from natural products. From Carpesium divaricatum S. et Z. (Compositae), various monoterpenoid compounds were isolated and exhibited mild antitumor activity against human tumor cell lines. These facts prompted us to explore the structure-activity relationship of these compounds. The synthesis of monoterpenoid compound was accomplished by Fries rearrangement, Grignard reaction, elimination, allylic oxidation, esterification and epoxidation as key steps. The results of in vitro cytotoxicity (A549, SK-OV-3, SK-MEL-2, XF498, HCT15) of the synthesised compounds are as follows: First of all, epoxide moiety is prerequisite for cytotoxic activity in diester compound. Any kind of compounds with olefin or diol moiety instead of epoxide ring exhibited poor or mild cytotoxic activity respectively. Of o-acetoxy and isobutoxy epoxy esters, p-sub-stituted phenylacetate compounds exhibited high cytotoxic activities against SK-MEL-2 and HCT15.

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The Effects of Pseudotsuga menziesii Monoterpenoids on Nitrification (Pseudotsuga menziesii의 Monoterpenoid가 질화작용에 미치는 효과)

  • ;Jean H. Langenheim
    • The Korean Journal of Ecology
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    • v.17 no.3
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    • pp.251-260
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    • 1994
  • Nitrification potential bioassay and terpenoid analyses were performed to determine the roles of terpenoid as an inhibitor of nitrification in the Douglas fir (Pseudotsuga menziesii) forests. The effect of terpenoids in the forest floor was also tested by adding $10{\mu}g/ml$ of four terpenoids(${\alpha}-pinene,{\beta}-pinene,{\gamma}-terpinene, and terpinolene) to mineral soils. The amount of terpenoids in the litter was higher than that in the soil and varied over time, but the amount of terpenoids in the soils was relatively constant. The correlation between the amount of terpenoids in the litter and ammonium oxidation was in inverse proportion to that in the mineral layers $(r^2=0.678)$. Inhibition of ammonium oxidation by terpenoids in the litter was always higher than in the mineral layer, but nitrite oxidation was different from the ammonium oxidation. The fact that there was greater nitrate production from ammonium in the mineral layer than in the forest floor layer seems to be due to the less amounts of terpenoids in the mineral layer. The result of the experiment in which four terpenoids were added to the mineral layer suggests that, after some lag time, the four terpenoids were effective in inhibiting ammonium oxidation. However, nitrite oxidation did not appear to be affected by the four terpenoids. Accordingly, all of our results suggested that terpenoids in Douglas fir forests apparently would act as a part of the inhibitors of nitrification.

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Insecticidal Activity and Ovipositional Repellency of Monoterpenoids against Moechotypa diphysis Adults (Coleoptera: Cerambycidae) (털두꺼비하늘소 성충에 대한 monoterpenoids의 살충활성과 산란기피)

  • 유정수;김길하;이상길;신상철;박지두;박승찬
    • Korean journal of applied entomology
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    • v.41 no.4
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    • pp.285-292
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    • 2002
  • These studies were carried out to investigate the fumigant toxicity, the contact toxicity and the ovipositional repellency of 25 monoterpenoids against oak longicorn beetle adults, Moechotypa diphysis. Monoterpenoids with 100% of fumigant toxicity were 1, 8-cinehone, fenchone, pulegone and (equation omitted)-terpinene at 20 (equation omitted)/954 ml (air) concentration, pulegone and (equation omitted)-terpinen at 10 (equation omitted)/954 ml (air) concentration, pulegone at 5 (equation omitted)/954 ml (air) concentration. Most monoterpenoids showed low or no contact toxicity but only pulegone showed about 70% mortality. Some monoterpenoids which had repellency to female adults with Y-tube olfactometer were bornylacetate, carvacrol, 1, 8-cineole and menthol at 1 (equation omitted) dose, while citronellol showed attractant response. Carveol, geraniol and perillyl alcohol of 25 monoterpenoids showed ovipoistional repellency of 82.1%, 78.3%, 87.5%, respectively, at the concentration of 1,000 ppm in the laboratory condition. In the field, the result tested with three monoterpenoids indicated that geraniol was the most effective one at the concentration of 10,000ppm and 1,000 ppm, but residual effect wasn't found.

Monoterpenoid of Korean Valerian Roots (국산 길초근의 Monoterpenoid)

  • Ryu, Kyung-Soo
    • Korean Journal of Pharmacognosy
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    • v.5 no.1
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    • pp.1-6
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    • 1974
  • Essential oils were separated by steam distillation from the roots of four species of the genus Valeriana and subjected to gas chromatography to screen monoterpenic hydrocarbons and related components. The amounts of the common components were contained in the following order: camphene, ${\alpha}-pinene$, bornyl-, myrtenyl isovalerate, myrtenylacetate and ${\beta}-pinene$, and small amounts of terpineol and terpinylacetate were also contained. Of the four species, the root of Valeriana fauriei $B_{RIQUET}$ var. dasycarpa $H_{ARA}$ contained the largest amounts of these components and the root of V. dageletiana $N_{AKAI}$ ex $M_{AEKAWA}$ the least. Since the root of V. dageletiana contained for less amounts of pinene, camphene and bornylacetate and none of dipentene and terpineol, this plant appears to be distinguished from the other three species.

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Monoterpenoids Concentration during Decomposition and Their Effect on Polysphondylium violaceum

  • Kim, Jong-Hee;Hwang, Ji-Young;Jo, Gyu-Gap;Kang, Ho-Nam
    • Journal of Ecology and Environment
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    • v.29 no.4
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    • pp.337-342
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    • 2006
  • The total monoterpenoid content of the pine litter layer and the availability of these compounds as inhibitors/stimulators on Polysphondylium violaceum of cellular slime molds were investigated. In order to determine the several monoterpenoids in the natural environment, we examined their concentrations in fresh, senescent, and decaying needles from 3 pine species (Pinus densiflora, P. thunbergii, P. rigida) by litter bag method. Total monoterpenoid content was highest in the fresh needles, but also remained relatively high in senescent needles. The effect of monoterpenoids identified from Pinus plants on the growth of P. violaceum was studied. We tested four concentrations (1, 0.1, 0.01, and $0.001\;{\mu}g/{\mu}L$) of each compound by using a disk volatilization technique. Each compound was treated after germination of spores of P. violaceum. All of the compounds at $1\;{\mu}g/{\mu}L$ concentration had a very strong inhibitory effect on cell growth of P. violaceum. Fenchone at all concentrations, myrcene, verbenone, bornyl acetate, and limonene at low concentrations stimulated the growth of P. violaceum. These results suggest that inhibitory or enhancing effects of selected monoterpenoids depend upon the concentration of the individual compound.

Systematics of Thuja Based on Leaf Monoterpenoids (측백나무속(Thuja)의 잎에 합유된 Monoterpenoids 분석을 통한 종간의 화학분류학적 연구)

  • 조규갑;김종희
    • The Korean Journal of Ecology
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    • v.27 no.3
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    • pp.161-164
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    • 2004
  • The compositions of the leaf monoterpenoids in 7 species of Thuja (Thuja orientalis, T. orientalis 'Avrea Nana', T. orientalis cv. compacts, T. occidentalis, T. occidentalis 'Boothii', T. occidentalis 'Pumila', T. occidentalis 'Tiny Tim') were analyzed by GC-MS and compared between species. These Thuja contains 30 compounds and α -pinene, camphene, sabinene, myrcene, limonene, bonyl acetate, γ-terpinene, α -terpinenyl acetatee are occurred in these all species. Compounds in these leaf extracts are remarkably different between species. The simplest monoterpenoid (11 compounds) was found in T. orientalis 'Avrea Nana' the most complex monoterpenoid was in T. occidentalis 'Pumila'(26 compounds). Based on these data, similarities are computed using presence/absence matching by PAUP (Phylogenetic Analysis Using Parsimony). It appears that four taxa are present within these Thuja plants. The minimum spanning network reveals that Thuja occidentalis and Thuja occidentalis 'Boothii' were the most similar compounds.

Monoterpenoid Loliolide Regulates Hair Follicle Inductivity of Human Dermal Papilla Cells by Activating the AKT/β-Catenin Signaling Pathway

  • Lee, Yu Rim;Bae, Seunghee;Kim, Ji Yea;Lee, Junwoo;Cho, Dae-Hyun;Kim, Hee-Sik;An, In-Sook;An, Sungkwan
    • Journal of Microbiology and Biotechnology
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    • v.29 no.11
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    • pp.1830-1840
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    • 2019
  • Loliolide is one of the most ubiquitous monoterpenoid compounds found in algae, and its potential therapeutic effect on various dermatological conditions via agent-induced biological functions, including anti-oxidative and anti-apoptotic properties, was demonstrated. Here, we investigated the effects of loliolide on hair growth in dermal papilla (DP) cells, the main components regulating hair growth and loss conditions. For this purpose, we used a three-dimensional (3D) DP spheroid model that mimics the in vivo hair follicle system. Biochemical assays showed that low doses of loliolide increased the viability and size of 3D DP spheroids in a dose-dependent manner. This result correlated with increases in expression levels of hair growth-related autocrine factors including VEGF, IGF-1, and KGF. Immunoblotting and luciferase-reporter assays further revealed that loliolide induced AKT phosphorylation, and this effect led to stabilization of β-catenin, which plays a crucial role in the hair-inductive properties of DP cells. Further experiments showed that loliolide increased the expression levels of the DP signature genes, ALP, BMP2, VCAN, and HEY1. Furthermore, conditioned media from loliolide-treated DP spheroids significantly enhanced proliferation and the expression of hair growth regulatory genes in keratinocytes. These results suggested that loliolide could function in the hair growth inductivity of DP cells via the AKT/β-catenin signaling pathway.

Phytoplasma Infection could Affect Chemical Composition of Artemisia sieberi

  • Hemmati, Chamran;Nikooei, Mehrnoosh
    • The Plant Pathology Journal
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    • v.35 no.3
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    • pp.274-279
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    • 2019
  • Artemisia sieberi showing symptoms resembling those caused by phytoplasma were observed in Geno Mountain, Hormozgan Province, Iran, and were examined for phytoplasma presence by PCR assays. In addition, the essential oils hydrodistilled from the aerial parts of phytoplasma-infected and healthy plants have been analyzed and compared by GC and GC/MS. Phylogenetic and virtual RFLP analysis of the 16S rRNA gene sequences revealed that the phytoplasma associated with A. sieberi witches' broom (AsWB) was a strain of 'Candidatus Phytoplasma aurantifolia'. The presence of the disease, however, induced a further enrichment (from 4.9 to 45.2%, a relative increase of 90%) of the entire monoterpene class as compared to the abundance in healthy samples. Conversely, a matching decrease in monoterpenoid (from 48.7 to 2%, a relative decrease of 90.2%) was observed in the infected plants. Besides the first report of phytoplasma infection of A. sieberi, the changes of its essential oils are reported.