• Title/Summary/Keyword: sesquiterpenoids

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Sesquiterpenoids from the Rhizome of Curcuma zedoaria

  • Hong, Chai-Hee;Kim, Young-heem;Lee, Sang-Kook
    • Archives of Pharmacal Research
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    • v.24 no.5
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    • pp.424-426
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    • 2001
  • In the course of searching for biologically active sesquiterpenoids from Curcuma genus, two sesquiterpenoids were isolated from the rhizome of Curcuma zedoaria (Zingiberaceae). Their structures were identified as ar-turmerone (1) and $\beta$-turmerone (2). The structure elucidation of compounds 1 and 2 was carried out by comparison of their physical and spectral data with previously reported values.

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Evaluation of Sesquiterpenoids Content and Growth Characters in Clonal Lines from a Cross between Atractylodes japonica Koidz. ex Kitam. and A. macrocephala Koidz

  • Kim, Kwan-Su;Park, Chun-Geun;Kim, Dong-Hwi;Park, Si-Hyung;Choung, Myoung-Gun
    • Korean Journal of Medicinal Crop Science
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    • v.14 no.2
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    • pp.107-112
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    • 2006
  • Two Atractylodes species, A. japonica Koidz. ex Kitam. (AJ) and A. macrocephala Koidz (AM) were used in this study. AJ population had higher amounts of Sesquiterpenoids and stronger tolerance to root rot but less vigor of root growth than AM population. Two populations (AJ and AM) were crossed to make interspecific hybrid population. A total of 98 lines propagated clonally were selected from a cross of AJ and AM, and evaluated for contents of sesquiterpenoids, atractylon (ATLN) and atractylenolide III (AT3) using high performance liquid chromatography (HPLC), and growth characters such as plant height, stem number and root weight. HPLC profiles of the hybrids were compared with those of parent plants, and it demonstrated the production of introgression hybrid by crossing between AJ and AM. Of 98 clonal lines,10 lines were selected by 10% level based on the growth vigor and tolerance to root rot, and AJM2102-51 line showed the heaviest root weight (117.1 g/plant) among them. A total of 98 hybrid lines contained on average $0.16\;{\pm}\;0.10\;mg/g$ of $AT3,\;2.00\;{\pm}\;1.37\;mg/g$ of ATLN, and $2.16\;{\pm}\;1.40\;mg/g$ of total sesquiterpenoids, showing high coefficients of variation (above 65%). Ten lines having high contents of sesquiterpenoids were selected, and AJM2101-15 had the highest amount (9.83 mg/g) of ATLN, and showed 40.8 g/plant of root weight similar to mean value (39.9 g/plant) of hybrid lines. The result showed that the introgression of both characters of vigorous growth from AM and high sesquiterpenoids content from AJ could be possible to make new hybrid lines by crossing between AJ and AM.

Studies on the Terpenoids in the Volatile Constituents of Liaoning Schisandra Chinensis Baillon

  • Hou, Dongyan;Zhang, Weihua;Hui, Ruihua
    • Analytical Science and Technology
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    • v.8 no.4
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    • pp.505-509
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    • 1995
  • The terpenoids in the volatile constituents of Liaoning Shcisandra Chinesis Baillon have been determined by the analytical method of GC/MS. Thirty terpenoids molecular structure were characterized. They are 11.89% monterpenes, 4.60% monoterpene oxides, 58.74% sesquiterpene hydrocarbons, and 1.62% oxygen-containing sesquiterpenoids in the total volatile constituents quantified by chromatograph. Among them, the sesquiterpene make up the characteristic constituents. Every terpenoid constituent percent content was obtained using area normalization method of HP-59970 chemstation.

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Some Sesquiterpenoids and $5{\alpha},8{\alpha}-$Epidioxysterols from Solanum lyratum

  • Yu, Su-Mi;Kim, Hyoung-Ja;Woo, Eun-Rhan;Park, Ho-Koon
    • Archives of Pharmacal Research
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    • v.17 no.1
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    • pp.1-4
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    • 1994
  • From the stems of Solanum lyratum Thunb.(Solanaceae), two sesquiterpenoids together with two 5$\alpha$, 8$alpha-epidioxy sterols have been isolated and identified as atractylenolide I, dehydrocarissone, engosterol peroxide, 9, 11-dehydroergosterol peroxide. These compounds never previously isolated from this genus.

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Guaiane Sesquiterpenoids from Torilis japonica and Their Cytotoxic Effects on Human Cancer Cell Lines

  • Park Hye Won;Choi Sang-Un;Baek Nam-In;Kim Sung-Hoon;Eun Jae Soon;Yang Jae Heon;Kim Dae Keun
    • Archives of Pharmacal Research
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    • v.29 no.2
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    • pp.131-134
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    • 2006
  • A new compound 2 and two known guaiane-type sesquiterpenoids were isolated from the methylene chloride-soluble fraction of the methanolic extract of the fruits of Torilis japonica (Umbelliferae) through repeated silica gel and Sephadex LH-20 column chromatography. Their chemical structures were elucidated as torilin (1), 11-acetoxy-8-angeloyloxy-$1{\beta}$-hydroxy-4-guaien-3-one ($1{\beta}$-hydroxytorilin, 2), and 11-acetoxy-8-angeloyloxy-$1{\alpha}$-hydroxy-4-guaien-3-one ($1{\alpha}$-hydroxytorilin, 3) by spectroscopic analysis. Compounds 1-3 exhibited cytotoxicity against human A549, SK-OV-3, SK-MEL-2, and HCT15 tumor cells.

Biosynthesis of Eudesmane-type Sesquiterpenoids by The Wood-rotting Fungus, Polyporus brumalis, on Specific Medium, including Inorganic Magnesium Source

  • Lee, Su-Yeon;Ryu, Sun-Hwa;Choi, In-Gyu;Kim, Myungkil
    • Journal of the Korean Wood Science and Technology
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    • v.44 no.2
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    • pp.253-263
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    • 2016
  • Fungi, such as the wood-rotting Polyporus brumalis, are excellent sources of pharmaceutically interesting natural products such as sesquiterpenoids. In this study, we investigated the biosynthesis of P. brumalis sesquiterpenoids on modified medium. Ten additional species of white rot fungi were inoculated in medium containing nutrients such as $C_6H_{12}O_6$, $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ at $28^{\circ}C$ for 25 days. After 10 days of incubation, eudesmane-type sesquiterpenes, ${\beta}$-eudesmane and ${\beta}$-eudesmol, were only synthesized during the growth phase of P. brumalis. Experiments excluding one nutrient at a time were conducted to determine the effects of inorganic nutrients on sesquiterpene biosynthesis. In conclusion, GC-MS analysis showed that biosynthesis of sesquiterpenes was differentially regulated by inorganic nutrients such as $MgSO_4$, $C_4H_{12}N_2O_6$, and $KH_2PO_4$. We found $MgSO_4$ supplementation to be vital for eudesmane-type sesquiterpene biosynthesis in P. brumalis; nitrogen ($C_4H_{12}N_2O_6$) and phosphate ($KH_2PO_4$) inhibited the synthesis of P. brumalis metabolites. Magnesium is a known cofactor of sesquiterpene synthase, which promotes ${\beta}$-eudesmol synthesis. To mechanistically understand eudesmane-type sesquiterpene biosynthesis in P. brumalis, further research into the genes regulating the dynamics of such biosynthesis is warranted.

Sesquiterpenoids from the Stem Bark of Aglaia grandis

  • Harneti, Desi;Permatasari, Atika Ayu;Anisshabira, Amallya;Naini, Al Arofatus;Nurlelasari, Nurlelasari;Mayanti, Tri;Maharani, Rani;Safari, Agus;Hidayat, Ace Tatang;Farabi, Kindi;Supratman, Unang;Azmi, Mohamad Nurul;Shiono, Yoshihito
    • Natural Product Sciences
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    • v.28 no.1
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    • pp.6-12
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    • 2022
  • Five sesquiterpenoids, 7-epi-eudesm-4(15)-ene,1β,6α-diol (1), 7-epi-eudesm-4(15)-ene,1β,6α-diol (2), saniculamoid D (3), aphanamol I (4), and 4β,10α-dihydroxyaromadendrane (5), were isolated from the stem bark of Aglaia grandis. The compounds' (1-5) chemical structures were identified by spectroscopic data including, IR, NMR (1H, 13C, DEPT 135°, HMQC, HMBC, 1H-1H COSY), and HRTOFMS, as well as by comparing with the previously reported spectral data. Therefore, this study described the structural elucidation of compounds 1-5 and evaluated their cytotoxic effects against Hela cervical and B16F10 melanoma cells for the first time, but no significant result was discovered.

Sesquiterpenoids Bioconversion Analysis by Wood Rot Fungi

  • Lee, Su-Yeon;Ryu, Sun-Hwa;Choi, In-Gyu;Kim, Myungkil
    • 한국균학회소식:학술대회논문집
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    • 2016.05a
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    • pp.19-20
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    • 2016
  • Sesquiterpenoids are defined as $C_{15}$ compounds derived from farnesyl pyrophosphate (FPP), and their complex structures are found in the tissue of many diverse plants (Degenhardt et al. 2009). FPP's long chain length and additional double bond enables its conversion to a huge range of mono-, di-, and tri-cyclic structures. A number of cyclic sesquiterpenes with alcohol, aldehyde, and ketone derivatives have key biological and medicinal properties (Fraga 1999). Fungi, such as the wood-rotting Polyporus brumalis, are excellent sources of pharmaceutically interesting natural products such as sesquiterpenoids. In this study, we investigated the biosynthesis of P. brumalis sesquiterpenoids on modified medium. Fungal suspensions of 11 white rot species were inoculated in modified medium containing $C_6H_{12}O_6$, $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ for 20 days. Cultivation was stopped by solvent extraction via separation of the mycelium. The metabolites were identified as follows: propionic acid (1), mevalonic acid lactone (2), ${\beta}$-eudesmane (3), and ${\beta}$-eudesmol (4), respectively (Figure 1). The main peaks of ${\beta}$-eudesmane and ${\beta}$-eudesmol, which were indicative of sesquiterpene structures, were consistently detected for 5, 7, 12, and 15 days These results demonstrated the existence of terpene metabolism in the mycelium of P. brumalis. Polyporus spp. are known to generate flavor components such as methyl 2,4-dihydroxy-3,6-dimethyl benzoate; 2-hydroxy-4-methoxy-6-methyl benzoic acid; 3-hydroxy-5-methyl phenol; and 3-methoxy-2,5-dimethyl phenol in submerged cultures (Hoffmann and Esser 1978). Drimanes of sesquiterpenes were reported as metabolites from P. arcularius and shown to exhibit antimicrobial activity against Gram-positive bacteria such as Staphylococcus aureus (Fleck et al. 1996). The main metabolites of P. brumalis, ${\beta}$-Eudesmol and ${\beta}$-eudesmane, were categorized as eudesmane-type sesquiterpene structures. The eudesmane skeleton could be biosynthesized from FPP-derived IPP, and approximately 1,000 structures have been identified in plants as essential oils. The biosynthesis of eudesmol from P. brumalis may thus be an important tool for the production of useful natural compounds as presumed from its identified potent bioactivity in plants. Essential oils comprising eudesmane-type sesquiterpenoids have been previously and extensively researched (Wu et al. 2006). ${\beta}$-Eudesmol is a well-known and important eudesmane alcohol with an anticholinergic effect in the vascular endothelium (Tsuneki et al. 2005). Additionally, recent studies demonstrated that ${\beta}$-eudesmol acts as a channel blocker for nicotinic acetylcholine receptors at the neuromuscular junction, and it can inhibit angiogenesis in vitro and in vivo by blocking the mitogen-activated protein kinase (MAPK) signaling pathway (Seo et al. 2011). Variation of nutrients was conducted to determine an optimum condition for the biosynthesis of sesquiterpenes by P. brumalis. Genes encoding terpene synthases, which are crucial to the terpene synthesis pathway, generally respond to environmental factors such as pH, temperature, and available nutrients (Hoffmeister and Keller 2007, Yu and Keller 2005). Calvo et al. described the effect of major nutrients, carbon and nitrogen, on the synthesis of secondary metabolites (Calvo et al. 2002). P. brumalis did not prefer to synthesize sesquiterpenes under all growth conditions. Results of differences in metabolites observed in P. brumalis grown in PDB and modified medium highlighted the potential effect inorganic sources such as $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ on sesquiterpene synthesis. ${\beta}$-eudesmol was apparent during cultivation except for when P. brumalis was grown on $MgSO_4$-free medium. These results demonstrated that $MgSO_4$ can specifically control the biosynthesis of ${\beta}$-eudesmol. Magnesium has been reported as a cofactor that binds to sesquiterpene synthase (Agger et al. 2008). Specifically, the $Mg^{2+}$ ions bind to two conserved metal-binding motifs. These metal ions complex to the substrate pyrophosphate, thereby promoting the ionization of the leaving groups of FPP and resulting in the generation of a highly reactive allylic cation. Effect of magnesium source on the sesquiterpene biosynthesis was also identified via analysis of the concentration of total carbohydrates. Our current study offered further insight that fungal sesquiterpene biosynthesis can be controlled by nutrients. To profile the metabolites of P. brumalis, the cultures were extracted based on the growth curve. Despite metabolites produced during mycelia growth, there was difficulty in detecting significant changes in metabolite production, especially those at low concentrations. These compounds may be of interest in understanding their synthetic mechanisms in P. brumalis. The synthesis of terpene compounds began during the growth phase at day 9. Sesquiterpene synthesis occurred after growth was complete. At day 9, drimenol, farnesol, and mevalonic lactone (or mevalonic acid lactone) were identified. Mevalonic acid lactone is the precursor of the mevalonic pathway, and particularly, it is a precursor for a number of biologically important lipids, including cholesterol hormones (Buckley et al. 2002). Farnesol is the precursor of sesquiterpenoids. Drimenol compounds, bi-cyclic-sesquiterpene alcohols, can be synthesized from trans-trans farnesol via cyclization and rearrangement (Polovinka et al. 1994). They have also been identified in the basidiomycota Lentinus lepideus as secondary metabolites. After 12 days in the growth phase, ${\beta}$-elemene caryophyllene, ${\delta}$-cadiene, and eudesmane were detected with ${\beta}$-eudesmol. The data showed the synthesis of sesquiterpene hydrocarbons with bi-cyclic structures. These compounds can be synthesized from FPP by cyclization. Cyclic terpenoids are synthesized through the formation of a carbon skeleton from linear precursors by terpene cyclase, which is followed by chemical modification by oxidation, reduction, methylation, etc. Sesquiterpene cyclase is a key branch-point enzyme that catalyzes the complex intermolecular cyclization of the linear prenyl diphosphate into cyclic hydrocarbons (Toyomasu et al. 2007). After 20 days in stationary phase, the oxygenated structures eudesmol, elemol, and caryophyllene oxide were detected. Thus, after growth, sesquiterpenes were identified. Per these results, we showed that terpene metabolism in wood-rotting fungi occurs in the stationary phase. We also showed that such metabolism can be controlled by magnesium supplementation in the growth medium. In conclusion, we identified P. brumalis as a wood-rotting fungus that can produce sesquiterpenes. To mechanistically understand eudesmane-type sesquiterpene biosynthesis in P. brumalis, further research into the genes regulating the dynamics of such biosynthesis is warranted.

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