germacrane sesquiterpenes

Summary

Summary: SESQUITERPENES cyclized to one 10-carbon ring.

Top Publications

  1. Liang Q, Min Z, Tang Y. A new elemanolide sesquiterpene lactone from Elephantopus scaber. J Asian Nat Prod Res. 2008;10:403-7 pubmed publisher
    ..The structure of 1 was elucidated on the basis of spectroscopic analysis. All three compounds exhibited significant inhibitory activities against human SMMC-7721 liver cancer cells in vitro (IC(50) 8.18-14.08 micromol/l). ..
  2. Zidorn C, Ellmerer Müller E, Stuppner H. A germacranolide and three hydroxybenzyl alcohol derivatives from Hieracium murorum and Crepis bocconi. Phytochem Anal. 2001;12:281-5 pubmed
    ..Sell gave 4-hydroxybenzoic acid 4-beta-D-glucopyranosyloxybenzyl ester (4), another new 4-hydroxybenzyl alcohol derivative. The structures of these compounds were established by means of MS and one- and two dimensional-NMR experiments. ..
  3. Nakagawa Y, Iinuma M, Matsuura N, Yi K, Naoi M, Nakayama T, et al. A potent apoptosis-inducing activity of a sesquiterpene lactone, arucanolide, in HL60 cells: a crucial role of apoptosis-inducing factor. J Pharmacol Sci. 2005;97:242-52 pubmed
    ..Taken together, the findings presented here indicate that arucanolide induced marked apoptosis in HL60 cells mainly by dissipating mitochondrial membrane potential, which would trigger AIF-induced apoptosis. ..
  4. Rivero Cruz B, Rivero Cruz I, Rodriguez J, Cerda García Rojas C, Mata R. Qualitative and quantitative analysis of the active components of the essential oil from Brickellia veronicaefolia by nuclear magnetic resonance spectroscopy. J Nat Prod. 2006;69:1172-6 pubmed
  5. Wong H, Brown G. Germacranolides from Artemisia myriantha and their conformation. Phytochemistry. 2002;59:529-36 pubmed
    ..The conclusions reached were supported by molecular modeling studies and an NMR spectroscopic investigation of the commercially available germacranolide, parthenolide. ..
  6. Wang Y, Li Z, Zhang H, Sha Y, Pei Y, Hua H. New germacrane sesquiterpenes from Salvia chinensis. Chem Pharm Bull (Tokyo). 2008;56:843-6 pubmed
    Two new germacrane sesquiterpenes, called salviadienol A (1) and salviadienol B (2), together with five known compounds, methyl-ent-4-epi-agath-18-oate (3), angelicoidenol (4), clovane-2beta,9alpha-diol (5), dehydrovomifoliol (6) and ..
  7. Faraldos J, Zhao Y, O Maille P, Noel J, Coates R. Interception of the enzymatic conversion of farnesyl diphosphate to 5-epi-aristolochene by using a fluoro substrate analogue: 1-fluorogermacrene A from (2E,6Z)-6-fluorofarnesyl diphosphate. Chembiochem. 2007;8:1826-33 pubmed
  8. Arimura G, Huber D, Bohlmann J. Forest tent caterpillars (Malacosoma disstria) induce local and systemic diurnal emissions of terpenoid volatiles in hybrid poplar (Populus trichocarpa x deltoides): cDNA cloning, functional characterization, and patterns of gene expression of (-)-ge. Plant J. 2004;37:603-16 pubmed
    ..Spatial patterns of FTC-induced PtdTPS1 transcript accumulation revealed acropetal but not basipetal direction of the systemic response. Implications for tritrophic poplar-FTC-predator/parasitoid interactions are discussed. ..
  9. Kotsos M, Aligiannis N, Myrianthopoulos V, Mitaku S, Skaltsounis L. Sesquiterpene lactones from Staehelina fruticosa. J Nat Prod. 2008;71:847-51 pubmed publisher
    ..Molecular modeling was incorporated to substantiate their relative configuration. ..

More Information

Publications90

  1. Njoroge S, Ukeda H, Sawamura M. Changes of the volatile profile and artifact formation in Daidai (Citrus aurantium) cold-pressed peel oil on storage. J Agric Food Chem. 2003;51:4029-35 pubmed
    ..The results could be applied for monitoring and control of the flavor quality of daidai essential oil and related products. ..
  2. Nelson L, Cool L, Solek C, Haverty M. Cuticular hydrocarbons and soldier defense secretions of Reticulitermes in southern California: a critical analysis of the taxonomy of the genus in North America. J Chem Ecol. 2008;34:1452-75 pubmed publisher
    ..The CHC phenotype SC-A found in southern California likely represents R. hesperus and SC-B appears to be a new, as yet undescribed species. We discuss the state of current taxonomic research on Reticulitermes. ..
  3. Fattorusso E, Luciano P, Romano A, Taglialatela Scafati O, Appendino G, Borriello M, et al. Stereostructure assignment of medium-sized rings through an NMR-computational combined approach. Application to the new germacranes ketopelenolides C and D. J Nat Prod. 2008;71:1988-92 pubmed publisher
  4. Zidorn C, Perry N. Chemistry of New Zealand Apiaceae: a rare phenylpropanoid and three new germacrane derivatives from Anisotome lyallii. Z Naturforsch C. 2001;56:951-6 pubmed
    ..haastii Cockayne & Laing and A. lyallii, and that some minor compounds in other species of Anisotome were isomers of 2 and 3. ..
  5. El Hassany B, El Hanbali F, Akssira M, Mellouki F, Haidour A, Barrero A. Germacranolides from Anvillea radiata. Fitoterapia. 2004;75:573-6 pubmed
    ..The structures of the compounds were elucidated from IR, HRMS, 1H and 13C-NMR, COSY, HETCOR, HMBC and HOHAHA spectral data. The major component 1 was tested for its cytotoxicity and antibacterial activity. ..
  6. Boulila A, Bejaoui A, Messaoud C, Boussaid M. Variation of volatiles in Tunisian populations of Teucrium polium L. (Lamiaceae). Chem Biodivers. 2008;5:1389-400 pubmed publisher
    ..In situ conservation of populations should be made appropriately according to these two factors. ..
  7. Radulovic N, Blagojević P. Volatile profiles of Artemisia alba from contrasting serpentine and calcareous habitats. Nat Prod Commun. 2010;5:1117-22 pubmed
    ..alba volatiles (genetically predetermined or environmental), especially in the case of populations grown on serpentine rock, characterized by a deficiency of water and indispensable mineral elements. ..
  8. Sosa S, Tubaro A, Kastner U, Glasl S, Jurenitsch J, Della Loggia R. Topical anti-inflammatory activity of a new germacrane derivative from Achillea pannonica. Planta Med. 2001;67:654-8 pubmed
    ..Hydrocortisone (0.10 micromol/cm(2)) reduced the cellular infiltrate by 44 %. ..
  9. Faraldos J, Kariuki B, Allemann R. Intermediacy of eudesmane cation during catalysis by aristolochene synthase. J Org Chem. 2010;75:1119-25 pubmed publisher
    ..Ammonium ion 6 seems to act as a genuine mimic of eudesmane cation (4) that most likely binds the active site of PR-AS in a productive conformation resembling that adapted by 4 during the PR-AS-catalyzed synthesis of 5. ..
  10. Ma X, Zheng J, Wu L, Guo D. Structural determination of three new germacrane-type sesquiterpene alcohols from curdione by microbial transformation. Magn Reson Chem. 2007;45:90-2 pubmed
    ..Among them, 4, 5 and 6 are new compounds. ..
  11. Maatooq G. Microbial conversion of partheniol by Calonectria decora. Z Naturforsch C. 2002;57:680-5 pubmed
    ..The identities of these metabolites were established by different spectroscopic measurements. ..
  12. Maatooq G. Microbial metabolism of partheniol by Mucor circinelloides. Phytochemistry. 2002;59:39-44 pubmed
    ..The structural assignments of these metabolites were made possible by different spectroscopic means. ..
  13. Felicetti B, Cane D. Aristolochene synthase: mechanistic analysis of active site residues by site-directed mutagenesis. J Am Chem Soc. 2004;126:7212-21 pubmed
  14. Bertea C, Voster A, Verstappen F, Maffei M, Beekwilder J, Bouwmeester H. Isoprenoid biosynthesis in Artemisia annua: cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library. Arch Biochem Biophys. 2006;448:3-12 pubmed
    ..These results demonstrate the potential of the use of A. annua glandular trichomes as a starting material for studying isoprenoid biosynthesis in this plant species. ..
  15. Stranden M, Borg Karlson A, Mustaparta H. Receptor neuron discrimination of the germacrene D enantiomers in the moth Helicoverpa armigera. Chem Senses. 2002;27:143-52 pubmed
  16. Lee S, Choi S, Choi S, Kim G, Kim Y, Lee K. Cytotoxic terpene hydroperoxides from the aerial parts of Aster spathulifolius. Arch Pharm Res. 2006;29:845-8 pubmed
    ..The two new compounds, 3 and 4, showed moderate cytotoxicity against human cancer cells with ED50 values ranging from 0.24 to 13.27 microg/mL. ..
  17. Wu S, Luo X, Ma Y, Hao X, Zhou J, Wu D. Two new germacranolides from Magnolia grandiflora. J Asian Nat Prod Res. 2001;3:95-102 pubmed
    ..The structures of the new compounds were elucidated on the basis of spectroscopic methods and X-ray diffraction...
  18. Xie H, Chen H, Cao B, Zhang H, Zou Z. Cytotoxic germacranolide sesquiterpene from Inula cappa. Chem Pharm Bull (Tokyo). 2007;55:1258-60 pubmed
    ..In vitro, it showed antiproliferative effects against human cervical cancer HeLa, human leukemia K562 and human nasopharyngeal carcinoma KB cell lines with IC(50) values of 1.2 microM, 3.8 microM and 5.3 microM, respectively. ..
  19. Zidorn C, Ellmerer Müller E, Dobner M, Stuppner H. A highly substituted germacranolide from Leontodon cichoraceus. Z Naturforsch C. 2001;56:904-8 pubmed
    ..The structure was established by APCI mass spectrometry and 1D- and 2D-NMR spectroscopy. A survey by HPLC-DAD and HPLC-MS gave no signs of this compound in 23 other taxa of Leontodon. ..
  20. Fuchino H, Koide T, Takahashi M, Sekita S, Satake M. New sesquiterpene lactones from Elephantopus mollis and their leishmanicidal activities. Planta Med. 2001;67:647-53 pubmed
    ..They exhibited potent in vitro leishmanicidal activities against Leishmania major. The alpha-methylene-gamma-butyrolactone moiety was found to be essential to the potent leishmanicidal effect observed. ..
  21. Pan Z, Wang Y, Li M, Xu G, Peng L, He J, et al. Terpenoids from Salvia trijuga. J Nat Prod. 2010;73:1146-50 pubmed publisher
    Nine new germacrane sesquiterpenes, trijugins A-I (1-9), a new lupane triterpenoid, 3alpha-O-acetyl-20(29)-lupen-2alpha-ol (10), and 24 known terpenoids were isolated from Salvia trijuga...
  22. Rosselli S, Maggio A, Raccuglia R, Morris Natschke S, Bastow K, Lee K, et al. Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta,10alpha-epoxy-salonitenolide. Nat Prod Commun. 2010;5:675-80 pubmed
    ..The cytotoxic activities of some compounds were determined against A549 and MCF-7 tumor cell lines. The esterified germacranolides 2-6 were selectively cytotoxic against the MCF-7 breast cancer cell line. ..
  23. Noge K, Becerra J. Germacrene D, a common sesquiterpene in the genus Bursera (Burseraceae). Molecules. 2009;14:5289-97 pubmed publisher
    ..Germacrene D has also been found in other Bursera species and some species of Commiphora, the sister group of Bursera, suggesting that the production of germacrene D might be an ancient trait in the genus Bursera...
  24. Chatzopoulou P, de Haan A, Katsiotis S. Investigation on the supercritical CO(2) extraction of the volatile constituents from Juniperus communis obtained under different treatments of the "berries" (cones). Planta Med. 2002;68:827-31 pubmed
    ..Significant differences were recorded between the supercritical CO(2) extract and the distilled oil, the latter being more enriched in monoterpenoid hydrocarbons. ..
  25. Matsuura N, Yamada M, Suzuki H, Hasegawa N, Kurosaka C, Ubukata M, et al. Inhibition of preadipocyte differentiation by germacranolides from Calea urticifolia in 3T3-L1 cells. Biosci Biotechnol Biochem. 2005;69:2470-4 pubmed
    ..But no inhibitory activity against cell proliferation and no nonspecific binding activity to protein were observed. These results indicate that these germacranolides are the specific inhibitors of preadipocyte differentiation. ..
  26. Zhou X, Li Z, Liang G, Zhu J, Wang D, Cai Z. Analysis of volatile components of Curcuma sichuanensis X. X. Chen by gas chromatography-mass spectrometry. J Pharm Biomed Anal. 2007;43:440-4 pubmed
    ..7%), beta-elemene (6.4%) and curzerene (6.2%). The results of semi-quantitative analysis indicated that levels of total sesquiterpene fraction (85.4%) were more than 55 times higher than those of monoterpene components (1.5%). ..
  27. Yan J, Chen G, Tong S, Feng Y, Sheng L, Lou J. Preparative isolation and purification of germacrone and curdione from the essential oil of the rhizomes of Curcuma wenyujin by high-speed counter-current chromatography. J Chromatogr A. 2005;1070:207-10 pubmed
    ..5/1, v/v) in tail to head elution mode. 62 mg of germacrone and 93 mg of curdione were obtained from 658 mg of the essential oil each at over 95% purity. Their structures were identified by 1H NMR and EI MS. ..
  28. Miller D, Yu F, Knight D, Allemann R. 6- and 14-Fluoro farnesyl diphosphate: mechanistic probes for the reaction catalysed by aristolochene synthase. Org Biomol Chem. 2009;7:962-75 pubmed publisher
  29. Quintana N, El Kassis E, Stermitz F, Vivanco J. Phytotoxic compounds from roots of Centaurea diffusa Lam. Plant Signal Behav. 2009;4:9-14 pubmed
    ..diffusa nor could it be identified in the root extract. However, a recent report from a different group maintains that 8-hydroxyquinoline can be released from roots of C. diffusa following a diurnal rhythm. ..
  30. Yang C, Yuan C, Jia Z. Xanthanolides, germacranolides, and other constituents from Carpesium longifolium. J Nat Prod. 2003;66:1554-7 pubmed
    ..Parthenolide and michelenolide exhibited significant cytotoxic activity against cultured SMMC-7721 (human hepatoma) and HO-8910 (human ovarian carcinoma) cells. ..
  31. Noge K, Shimizu N, Becerra J. (R)-(-)-linalyl acetate and (S)-(-)-germacrene D from the leaves of Mexican Bursera linanoe. Nat Prod Commun. 2010;5:351-4 pubmed
    ..The chemically unique blend in the leaves of B. linanoe may act as a chemical barrier against its potential herbivores, Blepharida beetles that have a tendency for attacking chemically similar plants as hosts...
  32. Setzer W. Ab initio analysis of the Cope rearrangement of germacrane sesquiterpenoids. J Mol Model. 2008;14:335-42 pubmed publisher
    ..Apparently, the generally small energy differences between the two forms in these sesquiterpenoids cannot be adequately reproduced at these levels of calculation. ..
  33. Røstelien T, Borg Karlson A, Faldt J, Jacobsson U, Mustaparta H. The plant sesquiterpene germacrene D specifically activates a major type of antennal receptor neuron of the tobacco budworm moth Heliothis virescens. Chem Senses. 2000;25:141-8 pubmed
    ..The purified compound was then re-tested via gas chromatography on the same receptor neuron type, verifying the identification. A weaker response to another sesquiterpene hydrocarbon was also recorded. ..
  34. Yang N, Qian S, Duan J, Li P, Tian L. Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum. J Asian Nat Prod Res. 2007;9:339-45 pubmed
    Three new germacrane sesquiterpenes, eupalinolides C-E (1-3), along with three known germacrane sesquiterpenes, eupalinolide A (4), eupalinolide B (5), and 3beta-acetoxy-8beta-(4'-hydroxytigloyloxy)-14-hydroxycostunolide (6), were ..
  35. Barrero A, Herrador M, López Pérez J, Arteaga J, Catalán J. New pathways in transannular cyclization of germacrone [germacra-1(10),4,7(11)-trien-8-one]: evidence regarding a concerted mechanism. Org Lett. 2009;11:4782-5 pubmed publisher
    ..This novel germacra-1(10),4-diene cyclization could suggest the existence of a new biosynthetic pathway to sesquiterpenes. ..
  36. Qu Y, Xu F, Nakamura S, Matsuda H, Pongpiriyadacha Y, Wu L, et al. Sesquiterpenes from Curcuma comosa. J Nat Med. 2009;63:102-4 pubmed publisher
    ..Among them, glechomanolide, curzerenone, curcolonol, alismol, alismoxide, and zedoarondiol showed no significant optical activities, so they may be artifact products during the isolation or drying process. ..
  37. Barquera Lozada J, Cuevas G. Biogenesis of sesquiterpene lactones pseudoguaianolides from germacranolides: theoretical study on the reaction mechanism of terminal biogenesis of 8-epiconfertin. J Org Chem. 2009;74:874-83 pubmed publisher
    ..Therefore, the mPWB95 method can be considered good to deal with this type of study. ..
  38. Yang F, Li S, Chen Y, Liu Q, Wang Y, Dong T, et al. [The fingerprint of Ezhu by GC-MS]. Yao Xue Xue Bao. 2005;40:1013-8 pubmed
    ..The relationship of chemical components and pharmacological activities should be further studied so as to elucidate the rationality of Chinese materia medica from multi-origins. ..
  39. Alkhatib R, Hennebelle T, Joha S, Roumy V, Güzel Y, Biabiany M, et al. Humulane and germacrane sesquiterpenes from Ferula lycia. J Nat Prod. 2010;73:780-3 pubmed publisher
    ..The two most active compounds, juniferinin (7) and 6-beta-p-hydroxybenzoyloxygermacra-1(10),4-diene (12), were moderately active against Raji lymphoma cells but also displayed some toxicity against healthy bone marrow cells. ..
  40. Yang F, Li S, Chen Y, Lao S, Wang Y, Dong T, et al. Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography-mass spectrometry. J Pharm Biomed Anal. 2005;39:552-8 pubmed
    ..phaeocaulis or C. wenyujin based on its location. Five components such as furanodienone, germacrone, curdione, curcumenol and neocurdione were optimized as markers for quality control of Ezhu. ..
  41. He X, Cane D. Mechanism and stereochemistry of the germacradienol/germacrene D synthase of Streptomyces coelicolor A3(2). J Am Chem Soc. 2004;126:2678-9 pubmed
    ..These results could be explained by a mechanism involving partitioning of a common helminthogermacradienyl cation intermediate 7. ..
  42. Heinrich G, Pfeifhofer H, Stabentheiner E, Sawidis T. Glandular hairs of Sigesbeckia jorullensis Kunth (Asteraceae): morphology, histochemistry and composition of essential oil. Ann Bot. 2002;89:459-69 pubmed
    ..In addition to long-stalked trichomes, small biseriate trichomes occurred, secreting small quantities of essential oil into a subcuticular space. ..
  43. You J, Cui F, Li Q, Yong sheng W, Han X, Yu Y. A HPLC method for the analysis of germacrone in rabbit plasma and its application to a pharmacokinetic study of germacrone after administration of zedoary turmeric oil. J Chromatogr B Analyt Technol Biomed Life Sci. 2005;823:172-6 pubmed
    ..Germacrone exhibited linear pharmacokinetics after intravenous administration of ZTO microemulsion to rabbits over the germacrone dose range 3.2-9.6 mg/ml. ..
  44. Yang N, Duan J, Shang E, Tian L. Analysis of sesquiterpene lactones in Eupatorium lindleyanum by HPLC-PDA-ESI-MS/MS. Phytochem Anal. 2010;21:144-9 pubmed publisher
    ..Compounds 6, 7 and 9 were reported for the first time. HPLC-PDA-ESI-MS/MS provides a new powerful approach to identify germacrane sesquiterpene lactones in E. lindleyanum rapidly and accurately. ..
  45. Tori M, Takeichi Y, Kuga H, Nakashima K, Sono M. Seven germacranolides, eupaglehnins A, B, C, D, E, and F, and 2alpha-acetoxyepitulipinolide from Eupatorium glehni. Chem Pharm Bull (Tokyo). 2002;50:1250-4 pubmed
  46. Zhang J, Guan J, Yang F, Liu H, Cheng X, Li S. Qualitative and quantitative analysis of four species of Curcuma rhizomes using twice development thin layer chromatography. J Pharm Biomed Anal. 2008;48:1024-8 pubmed publisher
    ..The investigated compounds had good linearity (r(2)>0.9905) within test ranges. Therefore, the developed TLC method can be used for quality control of Curcuma rhizomes. ..
  47. Lou Y, Baldwin I. Nitrogen supply influences herbivore-induced direct and indirect defenses and transcriptional responses in Nicotiana attenuata. Plant Physiol. 2004;135:496-506 pubmed publisher
  48. Djeddi S, Karioti A, Sokovic M, Stojkovic D, Seridi R, Skaltsa H. Minor sesquiterpene lactones from Centaurea pullata and their antimicrobial activity. J Nat Prod. 2007;70:1796-9 pubmed
    ..All compounds tested showed greater antibacterial and antifungal activities than the positive controls used. ..
  49. Gao X, Lin C, Jia Z. Cytotoxic germacranolides and acyclic diterpenoides from the seeds of Carpesium triste. J Nat Prod. 2007;70:830-4 pubmed
    ..Compounds 1, 2, and 4-7 exhibited significant cytotoxicity against HL-60 cells, and compound 10 exhibited cytotoxicity against SMMC-7721 cells. ..
  50. Rao R, Kumar U, Reddy S, Tiwari A, Rao J. Antioxidants and a new germacrane sesquiteroene from Carissa spinarum. Nat Prod Res. 2005;19:763-9 pubmed
    ..The chloroform extract of the plant displayed strong antioxidant (DPPH) activity. Several other known compounds were also isolated for the first time from this active extract. The antioxidant activity of major lignans was studied. ..
  51. Menelaou M, Henandez H, Macias F, Weidenhamer J, Williamson G, Fronczek F, et al. Constituents of Calamintha ashei: effects on Florida sandhill species. Nat Prod Commun. 2010;5:685-94 pubmed
    ..ashei provided six new menthofurans, two new germacrane sesquiterpenes, and the six, known flavonoids: 5-desmethoxynobiletin, 5-hydroxy-6,7,8,4'-tetramethoxyflavone, 5,4'-..
  52. Bischoff M, Schaller A, Bieri F, Kessler F, Amrhein N, Schmid J. Molecular characterization of tomato 3-dehydroquinate dehydratase-shikimate:NADP oxidoreductase. Plant Physiol. 2001;125:1891-900 pubmed
    ..This work completes our studies of the prechorismate pathway in that cDNAs for all seven enzymes (including isozymes) of the prechorismate pathway from tomato have now been characterized. ..
  53. Gioacchini A, Menotta M, Polidori E, Giomaro G, Stocchi V. Solid-phase microextraction gas chromatography/ion trap mass spectrometry and multistage mass spectrometry experiments in the characterization of germacrene D. J Mass Spectrom. 2002;37:1229-35 pubmed
    ..In fact, plants release hundreds of secondary metabolites that are important in their interactions with other organisms...
  54. Greenhagen B, Griggs P, Takahashi S, Ralston L, Chappell J. Probing sesquiterpene hydroxylase activities in a coupled assay with terpene synthases. Arch Biochem Biophys. 2003;409:385-94 pubmed
    ..The utility of this coupled assay was extended by examining the relative efficiency of the EAH enzyme to catalyze hydroxylations of different sesquiterpene skeletons generated by other terpene synthases. ..
  55. Catalan C, Del R Cuenca M, Hernández L, Joseph Nathan P. cis,cis-Germacranolides and melampolides from Mikania thapsoides. J Nat Prod. 2003;66:949-53 pubmed
    ..All compounds have a trans C-8 lactone ring closure. Their structures were elucidated using 1D and 2D NMR measurements, and the absolute configuration of 1 was determined using the Mosher ester method. ..
  56. Sirat H, Jamil S, Rahman A. Sesquiterpenes from the rhizomes of Curcuma ochrorhiza. Nat Prod Commun. 2009;4:1171 pubmed
    ..From the rhizomes of Curcuma ochrorhiza, four sesquiterpenes, isofuranodiene, germacrene, furanogermenone and zederone, have been isolated, the structures of which have been elucidated by spectroscopic methods. ..
  57. Franco M, Shibamoto T. Volatile composition of some Brazilian fruits: umbu-caja (Spondias citherea), camu-camu (Myrciaria dubia), Araça-boi (Eugenia stipitata), and Cupuaçu (Theobroma grandiflorum). J Agric Food Chem. 2000;48:1263-5 pubmed
    ..The chemical class of esters predominated in the cupuaçu sample. Ethyl butyrate and hexanoate were the major compounds in the headspace of this Amazonian fruit. ..
  58. Mozuraitis R, Stranden M, Ramirez M, Borg Karlson A, Mustaparta H. (-)-Germacrene D increases attraction and oviposition by the tobacco budworm moth Heliothis virescens. Chem Senses. 2002;27:505-9 pubmed
    ..Tobacco plants containing dispensers with low release rate of (-)-GD had a greater attractiveness than tobacco plants without this substance. In addition, a significant increase of oviposition was found on the plants with (-)-GD. ..
  59. Kisiel W, Dawid Pać R, Grabarczyk H, Nowak G. Germacrane derivatives from Santolina pinnata subsp. neapolitana. Z Naturforsch C. 2003;58:793-6 pubmed
    ..neapolitana, one new and four known germacrane derivatives were isolated. The new compound was characterized as 1alpha,10beta-epoxy-7alphaH-germacr-4(15)-ene-2/beta5alpha,6beta-triol by spectral methods. ..
  60. Jia N, Xiao Chi M, Xiu Lan X, Hong Wei J, Dean G. Structural determination of two new sesquiterpenes biotransformed from germacrone by Mucor alternata. Magn Reson Chem. 2008;46:178-81 pubmed
    ..Their structures were characterized on the basis of spectral methods including 2D NMR. Among them, (1S, 4S, 5S, 10R)-isozedoarondiol (2) and (1R, 4S, 5S, 10R)-diepoxy-12-hydroxygermacrone (3) are new compounds. ..
  61. Hong L, Li G, Zhou W, Wang X, Zhang K. Screening and isolation of a nematicidal sesquiterpene from Magnolia grandiflora L. Pest Manag Sci. 2007;63:301-5 pubmed
    ..The median lethal concentrations (LC50) of the compound against B. xylophilus and P. redivivus were 71 and 46 mg L(-1) respectively at 48 h. This is the first report of Magnoliaceae species with nematicidal activity...
  62. Cheng X, Liu H, Liao Y, Lai M, Liu J, Lu Z. [Comparisons of volatile components in different parts of three species of Rhizoma Curcumae]. Zhong Yao Cai. 2009;32:1551-3 pubmed
    ..The varieties of volatile components in different parts of three species of Rhizoma Curcumae are similar, but their contents are obviously various. We can make the leaves of Rhizoma Curcumae for recycling use. ..
  63. Palá Paúl J, Usano Alemany J, Brophy J, Pérez Alonso M, Soria A. Essential oil composition of the different parts of Eryngium aquifolium from Spain. Nat Prod Commun. 2010;5:817-21 pubmed
    ..However, similarities in volatile composition were found between E. aquifolium and other species growing under similar environmental conditions. As far as we know, this is the first report on the essential oil of this species. ..
  64. Bulow N, Konig W. The role of germacrene D as a precursor in sesquiterpene biosynthesis: investigations of acid catalyzed, photochemically and thermally induced rearrangements. Phytochemistry. 2000;55:141-68 pubmed
    ..The absolute configuration of gamma-amorphene was revised by correlation with the absolute configuration of germacrene D. The mechanisms of the rearrangement reactions are discussed. ..
  65. Wang P, Ran X, Chen R, Luo H, Liu Y, Zhou J, et al. Germacrane-type sesquiterpenoids from the roots of Valeriana officinalis var. latifolia. J Nat Prod. 2010;73:1563-7 pubmed publisher
    ..latifolia. The structures and relative configurations of 2-9 were elucidated on the basis of spectroscopic data interpretation. The effects of all compounds isolated on acetylcholinesterase were evaluated. ..
  66. Stranden M, Liblikas I, Konig W, Almaas T, Borg Karlson A, Mustaparta H. (-)-Germacrene D receptor neurones in three species of heliothine moths: structure-activity relationships. J Comp Physiol A Neuroethol Sens Neural Behav Physiol. 2003;189:563-77 pubmed
  67. Rivero A, Quintana J, Eiroa J, López M, Triana J, Bermejo J, et al. Potent induction of apoptosis by germacranolide sesquiterpene lactones on human myeloid leukemia cells. Eur J Pharmacol. 2003;482:77-84 pubmed
  68. Satitpatipan V, Suwanborirux K. New nitrogenous Germacranes from a Thai marine sponge, Axinyssa n. sp. J Nat Prod. 2004;67:503-5 pubmed
    Two new germacrane sesquiterpenes, including (1Z,4Z)-7alphaH-11-aminogermacra-1(10),4-diene (1) and N,N'-11-bis[(1Z,4Z)-7alphaH-germacra-1(10),4-dienyl]urea (2), were isolated from a Thai marine sponge Axinyssan. sp...
  69. Chang Y, Jin J, Nam H, Kim S. Point mutation of (+)-germacrene A synthase from Ixeris dentata. Biotechnol Lett. 2005;27:285-8 pubmed
    ..This is the first report that the hydroxyl group of threonine at the first position of the triad is required for the cyclase activity. ..
  70. Ahmed M, Rahman M, Alimuzzaman M, Shilpi J. Analgesic sesquiterpene dilactone from Mikania cordata. Fitoterapia. 2001;72:919-21 pubmed
    ..o.) significantly inhibited acetic acid-induced writhing in mice. Three other sesquiterpene dilactones isolated from the same plant, namely mikanolide, dihydromikanolide and scandenolide, did not show significant analgesic activity. ..
  71. Göpfert J, Bülow A, Spring O. Identification and functional characterization of a new sunflower germacrene A synthase (HaGAS3). Nat Prod Commun. 2010;5:709-15 pubmed
    ..The experiments show that independently regulated pathways for the first cyclic sesquiterpene, germacrene A, are present in sunflower. ..
  72. Park H, Lee J, Choi S, Baek N, Kim S, Yang J, et al. Cytotoxic germacranolide sesquiterpenes from the bark of Magnolia kobus. Arch Pharm Res. 2010;33:71-4 pubmed publisher
    ..Compounds 1-4 exhibited cytotoxicity against human A549, SK-OV-3, SK-MEL-2, and HCT15 tumor cells. ..
  73. Jiang P, Zhou J, Cao B, Wei G, He K, Liu B. [Study on the volatile oil of Murraya exotica]. Zhong Yao Cai. 2009;32:1224-7 pubmed
    ..0%), ar-Curcumene (2.5%). The major components of Murraya exotica are the terpenoids, including 80.6% of sesquiterpenoids and 11.9% of monoterpenoids. Bicyclogermacrene is identified in Murraya genus for the first time. ..
  74. Rubal J, Moreno Dorado F, Guerra F, Jorge Z, Galán M, Salido G, et al. A phenylpropanoid, a slovenolide, two sulphur-containing germacranes and Ca2+-ATPase inhibitors from Thapsia villosa. Planta Med. 2010;76:284-90 pubmed publisher
    ..Compounds 9, 10 and 11 increased significantly the cytoplasmic free calcium concentration ([Ca(2+)](c)) in human platelets in a concentration-dependent manner. ..
  75. Zhu N, Kikuzaki H, Sheng S, Sang S, Rafi M, Wang M, et al. Furanosesquiterpenoids of Commiphora myrrha. J Nat Prod. 2001;64:1460-2 pubmed
    ..Compound 1 exhibited weak cytotoxic activity against a MCF-7 breast tumor cell line in a clonogenic assay, while the other five compounds were inactive in this assay...
  76. Bakir M, Facey P, Hassan I, Mulder W, Porter R. Mikanolide from Jamaican Mikania micrantha. Acta Crystallogr C. 2004;60:o798-800 pubmed
    ..The crystal packing shows stacks of mikanolide molecules interlocked via a network of non-classical C-H...O hydrogen bonds between the lactone units. ..
  77. Umlauf D, Zapp J, Becker H, Adam K. Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae). Phytochemistry. 2004;65:2463-70 pubmed
  78. Deng C, Ji J, Li N, Yu Y, Duan G, Zhang X. Fast determination of curcumol, curdione and germacrone in three species of Curcuma rhizomes by microwave-assisted extraction followed by headspace solid-phase microextraction and gas chromatography-mass spectrometry. J Chromatogr A. 2006;1117:115-20 pubmed
    ..The results show that MAE-HS-SPME is a simple, rapid, solvent-free and reliable method for the determination of curdione, curcumol and germacrone in TCM, and also a potential and powerful tool for quality assessment of Rhizoma Curcuma. ..
  79. Appendino G, Aviello G, Ballero M, Borrelli F, Fattorusso E, Petrucci F, et al. Cytotoxic germacrane sesquiterpenes from the aerial parts of Santolina insularis. J Nat Prod. 2005;68:853-7 pubmed
    Chemical investigation of Santolina insularis afforded 11 germacrane sesquiterpenes (1-11), four of which (2, 3, 10, and 11) are new...
  80. You J, Li Q, Yu Y, Cui F. [Absorption of zedoary oil in rat intestine using in situ single pass perfusion model]. Yao Xue Xue Bao. 2004;39:849-53 pubmed
    ..4-1.2 mg x mL(-1). The absorption of curcumol, curdione and germacrone showed the passive diffusion process, and didn't contain a special absorption window. ..
  81. Aharoni A, Giri A, Deuerlein S, Griepink F, de Kogel W, Verstappen F, et al. Terpenoid metabolism in wild-type and transgenic Arabidopsis plants. Plant Cell. 2003;15:2866-84 pubmed
    ..This study further demonstrates the value of Arabidopsis for studies of the biosynthesis and ecological role of terpenoids and provides new insights into their metabolism in wild-type and transgenic plants. ..