• Title/Summary/Keyword: terpenoids

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Enhancing Production of Terpenoids in Metabolically Engineered Transgenic Spearmint (Mentha spicata L.) by Salt and Fungal Elicitors

  • Choi, Myung Suk;Park, Dong Jin;Song, Hyun Jin;Min, Ji Yun;Kang, Seung Mi;Lee, Chong Kyu;Cho, Kye Man;Karigar, Chandrakant;Kim, Ho Kyoung;Kang, Young Min
    • Journal of Forest and Environmental Science
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    • v.30 no.2
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    • pp.243-252
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    • 2014
  • Forest tree species usually takes for long periods to be harvested and cultivated but spearmints are a good model system for woody plant because of reducing and shortening cultivation time. Spearmints are good model plants (Mentha species) for research about terpenoids production and industrial essential oil manufacture. Isopentenyl pyrophosphate isomerase (Iso) and limonene synthase (Limo) are the key enzymes of terpenoid biosynthesis pathway. Transgenic and wild spearmints (Mentha spicata, MS) were cultured in vitro and assessed for the essential oil contents. The content of essential oil of transgenic spearmint also was enhanced slightly depending on the target terpenoid genes. In an attempt to increase productivity of terpenoids further, salt and fungal elicitation strategy was adopted on transgenic Mentha spicata. The salt (800 mM NaCl) as abiotic and two fungi (Botrytis cinerea and Glomerella cingulata) as biotic were used for elicitors. In the absence of salt stress four terpenoids were detected from the spearmint extracts, all of them being monoterpenes. On the other hand, the transgenic (MSIso) extracts contained eleven terpenoids (10 monoterpenes and 1 phenylpropene) while transgenic (MSLimo) extracts contained seven monoterpenes. After 3 days of fungal infection, the resistance indices further increased to 4.38, 3.89 and 2.04 for wild type, MSIso and MSLimo, respectively. The salt and fungal elicitators proved beneficial towards modifying both the terpenoids profile and improvement in the composition of essential oil. These results have important applications for the large-scale production of essential oils and forest biotechnology with respect to spearmint.

Biogenetic Differences in Essential Oil Constituents from the Leave of Pinus densiflora and Pinus koraiensis (소나무와 잣나무잎 정유성분의 생체학적 차이)

  • Song, Hong-Keun
    • Journal of the Korean Wood Science and Technology
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    • v.23 no.1
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    • pp.49-53
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    • 1995
  • The terpenoids are one of the secondary metabolities in Pinus species and functioned the protection them from insects or/and fungus etc. Since Pinus koraiensis has not any damage by Pine needle gall midge but Pinus densiflora has great injury by them in South Korea. It may great helf to find these reasons to analize their monoterpenenoids and to compare the seasonal variation of their amounts. Terpenoids were analized by GC, GC/MS. Some biogenetic analysis of terpenoids also was elucidated. The seasonal variation of terpenoid was distinguished at March and August and/or September. Most of major component of monoterpenes were increased or decreased in these periods in Pinus koraiensis. Especially 3-carene was showed significant variation between the period of physiological activity and the period of domain. The effect of infection by Pine needle gall midge was significant in Pinus densiflora for amount of monoterpene during the period of infection. The components of p-menthane series between Pinus densiflora and Pinus koraiensis was recognized a significant difference during the experiment. Biogenetic cooccurrance of pmenthane series also was recognized between 3-carene and terpinolene in Pinus koraiensis.

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Flavoral Essential Oil Components in the Stems of Agastache rugosa for Aromatherapy (아로마테라피용 배초향(Agastache rugosa) 줄기의 방향성 정유 성분)

  • Kim, Jeong-Mee
    • Journal of the Korean Society of Food Culture
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    • v.36 no.3
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    • pp.317-324
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    • 2021
  • This study was carried out to investigate the flavoral essential oil components in the stems of Agastache rugosa. These components were analyzed using gas chromatography-mass selective detector (GC-MSD). The stems of Agastache rugosa were contained alcohols, aldehydes, ketones, fatty acid esters, and terpenoids. The peak area (%) of estragole was highest among its oil components and the next were pulegone and menthone. The terpenoid alcohols found were 1-octen-3-ol, chavicol, spatulenol, 3-hexen-1-ol, 2-cyclohexen-1-ol, methyl eugenol, and octaethyllene glycol. The stems also contained ketones such as pulegone, menthone, cis-isopulegone, 2-cyclohexene-1-one, 3-octanone, 1-cyclohexanone, isoindole-1-one, t-ionone, inden-2-one, as well as the aldehydes of 4-methoxycinnam and benzaldehyde. The following esters were also detected 1-isopulegone-3-yl acetate, caryophyllene oxide, acetate and benzendicarboxylic acid ester. The terpenoids in the stems were identified as caryophyllene, limonene, cyclohexasiloxane-D, germacrene-D, anethole, cadinene, muurolene, and bourbonene. Overall Agastache rugosa contained several functional oil components including phenylpropanoids and terpenoids as flavoral essential oil components for natural aromatherapy.

A comparison of ATR-FTIR and Raman spectroscopy for the non-destructive examination of terpenoids in medicinal plants essential oils

  • Rahul Joshi;Sushma Kholiya;Himanshu Pandey;Ritu Joshi;Omia Emmanuel;Ameeta Tewari;Taehyun Kim;Byoung-Kwan Cho
    • Korean Journal of Agricultural Science
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    • v.50 no.4
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    • pp.675-696
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    • 2023
  • Terpenoids, also referred to as terpenes, are a large family of naturally occurring chemical compounds present in the essential oils extracted from medicinal plants. In this study, a nondestructive methodology was created by combining ATR-FT-IR (attenuated total reflectance-Fourier transform infrared), and Raman spectroscopy for the terpenoids assessment in medicinal plants essential oils from ten different geographical locations. Partial least squares regression (PLSR) and support vector regression (SVR) were used as machine learning methodologies. However, a deep learning based model called as one-dimensional convolutional neural network (1D CNN) were also developed for models comparison. With a correlation coefficient (R2) of 0.999 and a lowest RMSEP (root mean squared error of prediction) of 0.006% for the prediction datasets, the SVR model created for FT-IR spectral data outperformed both the PLSR and 1 D CNN models. On the other hand, for the classification of essential oils derived from plants collected from various geographical regions, the created SVM (support vector machine) classification model for Raman spectroscopic data obtained an overall classification accuracy of 0.997% which was superior than the FT-IR (0.986%) data. Based on the results we propose that FT-IR spectroscopy, when coupled with the SVR model, has a significant potential for the non-destructive identification of terpenoids in essential oils compared with destructive chemical analysis methods.

Identification and Growth Inhibition of Phytotoxic Substances from Artemisia scoparia (바쑥의 독성물질 확인과 생장억제작용)

  • Kil, Bong-Seop;Hyeon-Gyeong Yoo
    • The Korean Journal of Ecology
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    • v.19 no.4
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    • pp.295-304
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    • 1996
  • KDICical substances from Artemisia scoparia were analyzed by gas chromatography. Seven phenolic compounds and thirty nine terpenoids were identified. Most abundant within each group were cinnamic acid and camphor, respectively. The KDICicals were prepared as aqueous extracts and then used for germination, growth, and chlorophyll content tests. The extracts were inhibitory to germination and seedling growth of the receptor lants. This inhibitory effect was dependent on concentration. When the effect of the aqueous extract on chlorophyll content was assayed, both chlorophylls a and b were shown to be reduced. The reduction in seedling elongation and growth in dry weight paralleled the reduction in chlorophyll concentration. These KDICical substances, including phenolic compounds and terpenoids, from Artemisia scoparia were responsible for the growth inhibition of the selected species.

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Terpenoids from Citrus unshiu Peels and Their Effects on NO Production

  • Vu, Thi Oanh;Seo, Wonyoung;Lee, Jeong Hyung;Min, Byung Sun;Kim, Jeong Ah
    • Natural Product Sciences
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    • v.26 no.2
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    • pp.176-181
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    • 2020
  • Two new compounds, 3-methyl-but-2-en-1-yl-1-O-β-xylopyranosyl-(1"→2')-O-β-glucopyranoside (1) and 1-O-β-glucopyranosyl-6-hydroxy-2-methyl-hep-2-enoic acid (2), along with sixteen known terpenoids were isolated from the peels of Citrus unshiu Markov. Their structures were elucidated based on extensive NMR analyses (1H NMR, 13C NMR, DEPT, COSY, HMQC, and HMBC) and high-resolution mass spectrometry. In addition, all isolates (1 - 18) were tested their effects on nitric oxide (NO) production in RAW264.7 cells. Limonin (15) showed to inhibit LPS-induced NO production in a concentration-dependent manner without cytotoxicity.

Terpenoids of Cupressus species in California (캘리포니아 산(産) 삼나무 수종(樹種)의 Terpenoid 류(類))

  • Kim, Young-Kyoon;Zavarin, Eugene
    • Journal of the Korean Wood Science and Technology
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    • v.21 no.4
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    • pp.35-44
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    • 1993
  • 북가주에 있는 삼나무 수종에서 cadinane과 acorane류의 sesquiterpenoids를 chromatography를 사용하여 분리한 후, 화학적인 방법과 분광학적인 방법을 이용하여 분리된 성분의 화학구조를 규명하였다. 그 sesquiterpenoids의 생합성 경로를 정량적인 상관성에 의하여 밝혔다. 또한, 여러 삼나무 수종에 존재하는 sesquiterpenoids의 분류학적 차이에 대하여 논하였다.

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Hepatoprotective activity of terpenoids and terpenoid fractions of Scoparia dulcis L

  • Krishnamurthy, Praveen Thaggikuppe;Bajaj, Jitendra;Sharma, Abhishek;Manimaran, Sellappan;Ravanappa, Prashantha Kumar Bommenahalli;Pottekad, Vijayan
    • Advances in Traditional Medicine
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    • v.10 no.4
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    • pp.263-270
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    • 2010
  • Scoparia dulcis L. is widely used in the traditional system of medicine for treating liver ailments. In the present study the terpenoids and terpenoid fractions isolated from 1:1:1 petroleum ether, diethyl ether and methanol (PDM) extract of Scoparia dulcis L. were tested for their in vitro 1, 1-Diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity. Selected samples from the assay were further tested for their in vitro hepatoprotective activity against $CCl_4$ induced hepatotoxicity in freshly isolated rat hepatocytes. In the in vitro antioxidant study, fractions 7, 11, 13, 14, and 15 and PDM extract show the DPPH radical scavenging activity. The phytochemical screening of all these fractions show the presence of terpenoids. In the in vitro hepatoprotective study all these fractions and the PDM extract significantly prevent the $CCl_4$ induced changes in the aspartate aspartate amino transferase, alanine amino transferase and alkaline phosphatase levels (p < 0.05). The above results are comparable with the standard, silymarin. The results of the study indicate that, the PDM extract of Scoparia dulcis L. possesses potential hepatoprotective activity and this may be attributed to its free radical scavenging potential, which in turn may be attributed to the presence of terpenoids.

Structure of Three New Terpenoids, Spiciformisins a and b, and Monocyclosqualene, Isolated from the Herbs of Ligularia fischeri var. spiciformis and Cytotoxicity

  • Lee, Kyung-Tae;Koo, Sung-Ja;Jung, Seung-Hee;Choi, Jong-Won;Jung, Hyun-Ju;Park, Hee-Juhn
    • Archives of Pharmacal Research
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    • v.25 no.6
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    • pp.820-823
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    • 2002
  • The diethylet er fraction from the leaves extract of Ligularia fischeri var. spiciformis (Compositae) was subjected to silica gel column chromatography and yielded three new terpenoids named spiciformisin a (1), spiciformisin b (3), and monocyclosqualene (2). Acyclic diterpenes, spiciformisin a and -b, were established as 3,7,11,15-tetramethyl-1,3(20)-hexadecadiene and 3,7,11,15-tetramethyl-1,3,6,10,14-hexadecapentaene (IUPAC), respectively. A monocyclic triterpene, monocyclosqualene, were determined as [3,8,12,16,16-pentamethyl-(3,7,11,15-hexadecatetraenyl)]-3,3,5-trimethyl-1-cyclohexene. The structures were determined on the basis of NMR and MS analysis. Spiciformicin b showed potent cytotoxicity ($IC_{50},{\;}<9.7{;\}{\mu\textrm{g}}/ml$ against HL-60) in contrast to no cytotoxicity ($IC_{50},{\;}>200{\;}}{\mu\textrm{g}}/ml against HL-60 cells) of spiciformicin a with a cis-conjugated dienyl diexomethylene.