eudesmane sesquiterpenes


Summary: SESQUITERPENES cyclized into two adjoining cyclohexane rings but with a different configuration from the ARTEMISININS.

Top Publications

  1. Kouno I, Hirai A, Fukushige A, Jiang Z, Tanaka T. New eudesmane sesquiterpenes from the root of Lindera strychnifolia. J Nat Prod. 2001;64:286-8 pubmed
    ..Strychnistenolide exists as a single stereoisomer in CHCl(3), but in pyridine is epimerized. ..
  2. El Moghazy S, Ahmed A, Abdel Ghani H, El Shanawany M. A new eudesmane derivative from Onopordon ambiguum. Fitoterapia. 2002;73:97-8 pubmed
    ..The structures of both compounds were determined by spectroscopic techniques, including 1H-, 13C-NMR, DEPT, 1H-1H and 1H-13C COSY analysis. ..
  3. Kitajima J, Kamoshita A, Ishikawa T, Takano A, Fukuda T, Isoda S, et al. Glycosides of Atractylodes lancea. Chem Pharm Bull (Tokyo). 2003;51:673-8 pubmed
    ..The presence of six characteristic guaiane-type glucosides in both rhizomes of A. lancea and Atractylodes japonica suggested a close chemotaxonomic relationship between them. ..
  4. Yin H, Fu H, Hua H, Qi X, Li W, Sha Y, et al. Two new sesquiterpene lactones with the sulfonic acid group from Saussurea lappa. Chem Pharm Bull (Tokyo). 2005;53:841-2 pubmed
    ..Their structures, including the absolute configurations, were elucidated by spectroscopic methods. ..
  5. Liu Y, Jia W, Yao Z, Pan Q, Takaishi Y, Duan H. Two eudesmane sesquiterpenes from Laggera pterodonta. J Asian Nat Prod Res. 2007;9:233-7 pubmed
    Two new eudesmane sesquiterpenes, 2alpha-hydroxy pterodontic acid (1) and pterodolide [3alpha-(2-methyl-2,3-epoxy)-butyric-4alpha-acetoxy-8beta-ethoxy eudesma-7(11)-en-8alpha,12-olide (2), along with five known compounds (3-7) were ..
  6. Xie W, Weng C, Niu Y, Lai P, Row K. Eudesmane sesquiterpenes and other constituents from Aster himalaicus. Chem Biodivers. 2010;7:221-4 pubmed publisher
    ..The structures of all compounds have been elucidated on the basis of spectroscopic data, including IR, EI-MS, HR-ESI-MS, and 1D- and 2D-NMR data. ..
  7. Isaka M, Palasarn S, Lapanun S, Chanthaket R, Boonyuen N, Lumyong S. Gamma-lactones and ent-eudesmane sesquiterpenes from the endophytic fungus Eutypella sp. BCC 13199. J Nat Prod. 2009;72:1720-2 pubmed publisher
    Two new gamma-lactones, eutypellins A (1) and B (2), and two ent-eudesmane sesquiterpenes, ent-4(15)-eudesmen-11-ol-1-one (3) and ent-4(15)-eudesmen-1alpha,11-diol (4), together with three known pimarane diterpenes, diaporthein B, ..
  8. Khan A, Hussain J, Hamayun M, Kang S, Kim H, Watanabe K, et al. Allelochemical, eudesmane-type sesquiterpenoids from Inula falconeri. Molecules. 2010;15:1554-61 pubmed publisher
    ..The compound presented 92.34% inhibitory effect on the growth of lettuce at 500 ppm. Further field level experiments may help develop an environmentally friendly herbicide from this lead. ..
  9. Tong L, Xu H, Rezengcaidan -, Wang Y, Li W, Wang F, et al. A rapid identification of Radix inulae and its active component alantolactone in the Tibetan medicine Manuxitang. Biosci Trends. 2008;2:64-7 pubmed
    ..20% (n = 6) with an average RSD of 1.74%. Recovery was in the range of 93.5-98.5% with RSD value of 1.85%. The methods established were simple, accurate, and specific and could be used for quality control of Manuxitang. ..

More Information


  1. Okasaka M, Takaishi Y, Kashiwada Y, Kodzhimatov O, Ashurmetov O, Lin A, et al. Terpenoids from Juniperus polycarpus var. seravschanica. Phytochemistry. 2006;67:2635-40 pubmed
    ..seravschanica. Their structures were established on the basis of analysis of spectroscopic evidence. Some of the isolated terpenoids showed antimalarial activity. ..
  2. Shan Y, Wang X, Zhou X, Kong L, Niwa M. Two minor diterpene glycosides and an eudesman sesquiterpene from Coleus forskohlii. Chem Pharm Bull (Tokyo). 2007;55:376-81 pubmed
    ..Compounds 1 and 2 showed relaxative effects on isolated guinea pig tracheal spirals in vitro...
  3. 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
  4. Galal A. Microbial transformation of pyrethrosin. J Nat Prod. 2001;64:1098-9 pubmed
    ..The structure elucidation of these metabolites was based primarily on 1D and 2D NMR analyses. The isolated metabolites exhibited cytotoxic, antifungal, and antiprotozoal activities. ..
  5. Adio A, Paul C, König W, Muhle H. Volatile constituents in the liverwort Tritomaria polita. Phytochemistry. 2003;64:637-44 pubmed
  6. Wang S, Zhang J, Guo X, Song Q, Zhao W. A new eudesmane sesquiterpene lactone from Curcuma wenyujin. Yao Xue Xue Bao. 2007;42:1062-5 pubmed
    ..Among them, compound 1 was found to be a new eudesmane sesquiterpene lactone, whilst compounds 2-5 were obtained from this plant for the first time. ..
  7. Forcat S, Allemann R. Stabilisation of transition states prior to and following eudesmane cation in aristolochene synthase. Org Biomol Chem. 2006;4:2563-7 pubmed
    ..These results complete a screen of likely active-site aromatic residues and establish their respective roles in the conversion of FPP to aristolochene. ..
  8. Shy H, Wu C. Eudesmane-type sesquiterpenoids from the liverwort Lepidoziafauriana. J Asian Nat Prod Res. 2006;8:723-31 pubmed
    ..Their structures were determined by NMR and X-ray analyses. Three chemo-types of Lepidoziafauriana may be classified according to the skeleton of the major sesquiterpenoids identified in the species. ..
  9. Kanerva L, Estlander T, Alanko K, Jolanki R. Patch test sensitization to Compositae mix, sesquiterpene-lactone mix, Compositae extracts, laurel leaf, Chlorophorin, Mansonone A, and dimethoxydalbergione. Am J Contact Dermat. 2001;12:18-24 pubmed
    ..The concentration of the individual components of the Compositae mix should be adjusted so that the mix detects allergic patients but does not sensitize. ..
  10. Pan L, Kardono L, Riswan S, Chai H, Carcache de Blanco E, Pannell C, et al. Isolation and characterization of minor analogues of silvestrol and other constituents from a large-scale re-collection of Aglaia foveolata. J Nat Prod. 2010;73:1873-8 pubmed publisher
    ..Several of the compounds isolated were also evaluated in a NF-?B (p65) inhibition assay...
  11. Ahmed A, Mohamed A, Tzakou O, Gani A, Yannitsaros A, El Maghraby M, et al. Three pyrone glucosidic derivatives from Conyza albida. Planta Med. 2002;68:664-6 pubmed
    ..The structures were elucidated by high field NMR spectroscopy. ..
  12. Sun Z, Chen B, Zhang S, Hu C. Four new eudesmanes from Caragana intermedia and their biological activities. J Nat Prod. 2004;67:1975-9 pubmed
    ..Compound 7 showed glucose consumption activity with an IC value of 10.7 microg/mL in a C2C12 muscle cell assay. The MIC value of this compound (100 mg/kg) in a db/db mice model is equivalent to that of metformin in vivo. ..
  13. Mou L, Zhu L, Lin Z, Liang X. Stereoselective total synthesis of chrysanthemol. J Asian Nat Prod Res. 2001;3:103-16 pubmed
    ..Seven intermediary compounds were tested for inhibitory effects on the carragenan-induced swelling of mouse paw but demonstrated no obvious activities. ..
  14. Levine S, Krout M, Stoltz B. Catalytic enantioselective approach to the eudesmane sesquiterpenoids: total synthesis of (+)-carissone. Org Lett. 2009;11:289-92 pubmed publisher
    ..The devised synthetic strategy allowed for the preparation of the antibacterial agent (+)-carissone and a formal synthesis of the P/Q-type calcium channel blocker (-)-alpha-eudesmol. ..
  15. Carvalho M, Alves J, da Cunha E, Barbosa Filho J, Silva M. Pimarane diterpenes and a sesquiterpene from Salzmmania nitida. An Acad Bras Cienc. 2006;78:17-21 pubmed
    ..The structures and unambiguous 1H and 13C chemical shift assignments were established by spectroscopic means, including homo and heteronuclear techniques. ..
  16. Stojakowska A, Michalska K, Malarz J. Simultaneous quantification of eudesmanolides and thymol derivatives from tissues of Inula helenium and I. royleana by reversed-phase high-performance liquid chromatography. Phytochem Anal. 2006;17:157-61 pubmed
    ..royleana has been developed. The method could be applied to screen raw materials in search for highly productive plants and in vitro cultures. ..
  17. Cheng Z, Wu T, Bligh S, Bashall A, Yu B. cis-Eudesmane sesquiterpene glycosides from Liriope muscari and Ophiopogon japonicus. J Nat Prod. 2004;67:1761-3 pubmed
    ..The structure and the relative configuration of compound 1 were confirmed by X-ray crystallographic analysis. This is the first time that cis-eudesmane-type sesquiterpenes have been reported from the genera Ophiopogon and Liriope...
  18. Chen Y, Chou G, Wang Z. [Determination of beta-eudesmol in rhizome of Atractylodes lancea by RP-HPLC]. Zhongguo Zhong Yao Za Zhi. 2007;32:2265-7 pubmed
    ..048-1.200 microg (r = 0.999 9), the average recovery was 99.3%, RSD was 1.4% (n = 9). The method for quantitation of beta-eudesmol in A. lancea was accurate and reliable, which can be used to evaluate the quality of rhizome of A. lancea. ..
  19. Robles Zepeda R, Lozoya Gloria E, Lopez M, Villarreal M, Ramírez Chávez E, Molina Torres J. Montanoa tomentosa glandular trichomes containing kaurenoic acids chemical profile and distribution. Fitoterapia. 2009;80:12-7 pubmed publisher
    ..In the glandular trichomes of the leaves also up to twenty-six volatile terpenes were identified, where beta-eudesmol and valencene were the most abundant terpenes. ..
  20. Morikawa T, Kishi A, Pongpiriyadacha Y, Matsuda H, Yoshikawa M. Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpene and aldose reductase inhibitors from Salacia chinensis. J Nat Prod. 2003;66:1191-6 pubmed
    ..In addition, six constituents, 3beta,22beta-dihydroxyolean-12-en-29-oic acid, tingenone, tingenine B, regeol A, triptocalline A, and mangiferin, were found to show an inhibitory effect on rat lens aldose reductase. ..
  21. Tigno X, Gumila E. In vivo microvascular actions of Artemisia vulgaris L. in a model of ischemia-reperfusion injury in the rat intestinal mesentery. Clin Hemorheol Microcirc. 2000;23:159-65 pubmed
    ..The extract fractions contain yomogin, which has been previously shown to inhibit iNOS activity, and may therefore explain the anti-inflammatory property of the plant. ..
  22. Kozawa S, Ishiyama H, Fromont J, Kobayashi J. Halichonadin E, a dimeric sesquiterpenoid from the sponge Halichondria sp. J Nat Prod. 2008;71:445-7 pubmed
    ..Halichonadin E ( 1) is the first hetero-dimeric sesquiterpenoid with eudesmane and aromadendrane skeletons linked through a urea fragment. ..
  23. Komiya T, Yamada Y, Moteki H, Katsuzaki H, Imai K, Hibasami H. Hot water soluble sesquiterpenes [anhydroperoxy-costunolide and 3-oxoeudesma-1,4(15),11(13)triene-12,6alpha-olide] isolated from laurel (Laurus nobilis L.) induce cell death and morphological change indicative of apoptotic chromatin condensation in l. Oncol Rep. 2004;11:85-8 pubmed
    ..On the other hand, fragmentations by these compounds of DNA to oligonucleosomal-sized fragments were not observed in the HL-60 cells. ..
  24. Wu Y, Li N, Wang M. [Research progress on chemical constituents of Laggera plants in China]. Zhongguo Zhong Yao Za Zhi. 2006;31:181-4 pubmed
    ..More than 100 compounds were obtained from these plants. In order to assist in medicinal application of this species of plants, progresses made in this field are systemically reviewed in this article. ..
  25. Chiou L, Ling J, Chang C. Chinese herb constituent beta-eudesmol alleviated the electroshock seizures in mice and electrographic seizures in rat hippocampal slices. Neurosci Lett. 1997;231:171-4 pubmed
    ..5 microM)-induced electrographic seizure activity. The potential of beta-eudesmol to serve as an antiepileptic or a conjuvant in phenytoin therapy is suggested. ..
  26. Jia C, Mao D, Zhang W, Sun X. [Studies on chemical constituents in essential oil from wild Atractylodes lancea in dabie mountains]. Zhong Yao Cai. 2004;27:571-4 pubmed
    ..alpha, 7. alpha, 7a. alpha,7b. alpha-)] -and gamma-eudesmol. Both the major constituents and contents were different from that had been reported. ..
  27. Kimura I. Medical benefits of using natural compounds and their derivatives having multiple pharmacological actions. Yakugaku Zasshi. 2006;126:133-43 pubmed
    ..The pleiotropic actions of natural compounds and their derivatives serve as important clues for developing new drugs for various chronic diseases. ..
  28. Sánchez Martínez R, Villaescusa Castillo L, Bernabe M, Diaz Lanza A. Two new eudesmane alcohols from Jasonia glutinosa. Z Naturforsch C. 2000;55:693-6 pubmed
    ..C. The structure of these sesquiterpenes were characterized by 1D and 2D NMR techniques (DQCOSY. TOCSY, NOESY, HMQC and HMBC) as (11R)-eudesm-4-en-11,12-diol and (11R)-eudesmane-5alpha, 11,12-triol. ..
  29. Chen K, Baran P. Total synthesis of eudesmane terpenes by site-selective C-H oxidations. Nature. 2009;459:824-8 pubmed publisher
    ..This work establishes an intellectual framework in which to conceive the laboratory synthesis of other complex terpenes using a 'two-phase' approach. ..
  30. Al Dabbas M, Hashinaga F, Abdelgaleil S, Suganuma T, Akiyama K, Hayashi H. Antibacterial activity of an eudesmane sesquiterpene isolated from common Varthemia, Varthemia iphionoides. J Ethnopharmacol. 2005;97:237-40 pubmed
    ..The minimum inhibitory concentrations (MICs) of this compound which was determined by the agar dilution method ranged between 250 and 500 microg/ml. ..
  31. Zhang T, Xiao W, Gong T, Yang Y, Chen R, Yu D. Two new eudesmanolides from Inula racemosa. J Asian Nat Prod Res. 2010;12:788-92 pubmed publisher
    ..The anti-inflammatory activities were also tested, but neither of them showed any activities. ..
  32. Li S, Shi H, Chang W, Li Y, Zhang M, Qiao Y, et al. Eudesmane sesquiterpenes from Chinese liverwort are substrates of Cdrs and display antifungal activity by targeting Erg6 and Erg11 of Candida albicans. Bioorg Med Chem. 2017;25:5764-5771 pubmed publisher
    ..Buch., including four new compounds. Among them, five eudesmane sesquiterpenes were ineffective against Candida albicans wild strain SC5314 but active towards efflux pumps-deficient ..
  33. Ono M, Masuoka C, Odake Y, Ito Y, Nohara T. Eudesmane derivatives from Tessaria integrifolia. Phytochemistry. 2000;53:479-84 pubmed Pavon (Compositae). Their structures were elucidated on the basis of spectroscopic analysis is well as chemical evidence. ..
  34. Vera N, Misico R, Sierra M, Asakawa Y, Bardon A. Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda. Phytochemistry. 2008;69:1689-94 pubmed publisher
    ..Our results, from feeding choice tests, indicated that most of the compounds deter larval feeding at the cited concentration. ..
  35. Kitajima J, Suzuki N, Satoh M, Watanabe M. Sesquiterpenoids of Torilis japonica fruit. Phytochemistry. 2002;59:811-5 pubmed
    ..The absolute stereostructures of these sesquiterpenoids were elucidated by the modified Mosher's method. ..
  36. Wang H, Zhang H, Zhou Y, Zuo J, Qin G. Sesquiterpenoids from Saussurea laniceps. J Nat Prod. 2005;68:762-5 pubmed
    ..The immunomodulatory activities of compounds 1-3 were evaluated. Of these, compound 3 showed significant inhibition of the proliferation of murine T and B cells in vitro. ..
  37. Thuy T, Sung T, Hao N. An eudesmane glycoside from Fissistigma pallens. Pharmazie. 2006;61:570-1 pubmed
    ..amp; Gagn.) Merr. (Annonaceae), a Vietnamese folk medicinal plant, a novel eudesmane glycoside named fissispallin (1) has been isolated, besides afzelin. Their structures were elucidated by spectroscopic methods (1H, 13C and 2D NMR). ..
  38. Garcia A, Delgado G. Cytotoxic cis-fused bicyclic sesquiterpenoids from Jatropha neopauciflora. J Nat Prod. 2006;69:1618-21 pubmed
    ..Biological investigation of less polar fractions of the bark extract led to the isolation of moderately cytotoxic triterpenes, calenduladiol (3) and (3beta,16beta)-16-hydroxylup-20(29)-en-3-yl (E)-3-(4-hydroxyphenyl)prop-2-enoate (4). ..
  39. Wang X, Wu Q, Shi Y. Terpenoids and sterols from Saussurea cauloptera. Chem Biodivers. 2008;5:279-89 pubmed publisher
    ..The structurally related compounds 1-4 were found to exhibit strong inhibitory activities against human gastric carcinoma (SGC-7901) cells. ..
  40. Ishiyama H, Kozawa S, Aoyama K, Mikami Y, Fromont J, Kobayashi J. Halichonadin F and the Cu(I) complex of halichonadin C from the sponge Halichondria sp. J Nat Prod. 2008;71:1301-3 pubmed publisher
    ..and the structures and relative stereochemistries of 1 and the complex of 2 were elucidated on the basis of spectroscopic data and chemical methods. ..
  41. Ahmed A, Abdel Razek M, Nassar M, Izumi S, Ohta S, Hirata T. An eudesmanolide and a carotane from Ferula sinaica. Phytochemistry. 2001;57:513-5 pubmed
    ..Re-examination of the chemical constituents of the leaves of Ferula sinaica afforded a new eudesmanolide and a new carotane. The structures were elucidated by spectroscopic methods. ..
  42. Al Dabbas M, Suganuma T, Kitahara K, Hou D, Fujii M. Cytotoxic, antioxidant and antibacterial activities of Varthemia iphionoides Boiss. extracts. J Ethnopharmacol. 2006;108:287-93 pubmed
    ..A compound responsible for the antibacterial activity was isolated from the ethyl acetate extract, and identified as 3-oxocostusic acid. ..
  43. Garcia Granados A, Gutierrez M, Parra A, Rivas F. Chemical-microbiological synthesis of cryptomeridiol derivatives by Gliocladium roseum: semisynthesis of 11-hydroxyeudesmanolides. J Nat Prod. 2002;65:1011-5 pubmed
    ..Semisyntheses of 11-hydroxyeudesmanolides from the isolated 11,12-dihydroxylated metabolites were also accomplished and used in assigning the stereochemistry of hydroxylation. ..
  44. Ahmed A, Khattab A, Grace M, Sahl M. A new eudesmanolide from Crataegus flava fruits. Fitoterapia. 2001;72:756-9 pubmed
    ..A new eudesmanolide, 1beta,9alpha-dihydroxyeudesm-3-en-5beta,6alpha,7alpha,11alphaH-12,6-olide (1), was isolated from Crataegus flava fruits. Its structure was determined by spectroscopic methods. ..
  45. Kim S, Kim T. Synergistic induction of 1,25-dihydroxyvitamin D(3)- and all-trans-retinoic acid-induced differentiation of HL-60 leukemia cells by yomogin, a sesquiterpene lactone from Artemisia princeps. Planta Med. 2002;68:886-90 pubmed
    ..Abbreviations. 1,25-(OH)(2) D(3) :1,25-dihydroxyvitamin D(3) FITC:fluorescein isothiocyanate NBT:nitroblue tetrazolium RA:retinoic acid PE:phytoerythrin ..
  46. García M, Sosa M, Donadel O, Giordano O, Tonn C. Allelochemical effects of eudesmane and eremophilane sesquiterpenes on Tribolium castaneum larvae. J Chem Ecol. 2003;29:175-87 pubmed
    ..Maximum repellency was caused by the 3-oxo-gamma-costic acid. However, experimental series carried out using gamma-costic acid, eremophilan-1(10),2,11(13)-trien-12-oic acid, costic aldehyde, and ilicic aldehyde showed no clear response. ..
  47. Xiao Y, Zheng Q, Zhang Q, Sun H, Guéritte F, Zhao Y. Eudesmane derivatives from Laggera pterodonta. Fitoterapia. 2003;74:459-63 pubmed
    ..Moreover, six known compounds were isolated: pterodontriol A (2), pterodontriol B, pterodonta acid (3), ilicic acid (4), costic acid and beta-amyrin. Cytotoxic activity of compounds 2, 3 and 4 was investigated. ..
  48. Huo Y, Shi H, Li W, Wang M, Li X. HPLC determination and NMR structural elucidation of sesquiterpene lactones in Inula helenium. J Pharm Biomed Anal. 2010;51:942-6 pubmed publisher
    ..helenium. In addition, two minor isomers in I. helenium were isolated by semi-preparative HPLC. Their structures were elucidated on the basis of NMR analysis. ..
  49. Fang L, Chen J, Zheng G, Zhang C, Li Y. Synthesis of 4,5-seco-eudesman-type sesquiterpenes: 4,5-dioxo-10-epi-4,5-seco-gamma-eudesmane and 4,5-dioxo-10-epi-4,5-seco-gamma-eudesmanol. Chirality. 2005;17:163-6 pubmed
    ..Avoiding expensive reagents, this highly economic method is especially suited for the synthesis of 4,5-seco-eudesman-type and iphionan-type sesquiterpenes with a double bond at positions 11 and 12. ..
  50. Jeong S, Koo S, Ha J, Ryu S, Park H, Lee K. Induction of apoptosis by yomogin in human promyelocytic leukemic HL-60 cells. Biol Pharm Bull. 2004;27:1106-11 pubmed
  51. Seo J, Lim S, Kim J, Lim J, Ha Y, Lee I, et al. Nrf2-mediated induction of detoxifying enzymes by alantolactone present in Inula helenium. Phytother Res. 2008;22:1500-5 pubmed publisher
    ..In conclusion, alantolactone appears to induce detoxifying enzymes via activation of PI3K and JNK signaling pathways, leading to translocation of Nrf2, and subsequent interaction between Nrf2 and ARE in the encoding genes. ..
  52. Tachikawa E, Takahashi M, Kashimoto T. Effects of extract and ingredients isolated from Magnolia obovata thunberg on catecholamine secretion from bovine adrenal chromaffin cells. Biochem Pharmacol. 2000;60:433-40 pubmed
    ..Furthermore, the results indicate that the inhibitory effect of magnolia bark may be associated with its pharmacological effect on activities of the nervous system. ..
  53. Cheng S, Wang S, Wen Z, Dai C, Duh C. Three new eudesmanoids from the Formosan soft coral Nephthea erecta. J Asian Nat Prod Res. 2009;11:967-73 pubmed publisher
    ..The anti-inflammatory activity using RAW 264.7 macrophages and their cytotoxicity against selected cancer cells of 1-3 were evaluated in vitro. ..
  54. Chen R, Zou J, Jia J, Dai J. Chemical constituents from the cell cultures of Saussurea involucrata. J Asian Nat Prod Res. 2010;12:119-23 pubmed publisher
    ..Among them, syringin is the main compound with an isolated yield of 0.3%. The new compound was characterized as 11 beta H-2 alpha-hydroxy-eudesman-4(15)-en-12,8 beta-olide (1) on the basis of extensive spectroscopic data. ..
  55. Yu F, Harada H, Yamasaki K, Okamoto S, Hirase S, Tanaka Y, et al. Isolation and functional characterization of a beta-eudesmol synthase, a new sesquiterpene synthase from Zingiber zerumbet Smith. FEBS Lett. 2008;582:565-72 pubmed publisher
    ..coli and coexpressed it with ZSS2. When supplemented with mevalonate, the engineered E. coli produced a similar sesquiterpene profile to that produced in the in vitro enzyme assay, and the yield of beta-eudesmol reached 100 mg/L...
  56. Cantrell C, Pridgeon J, Fronczek F, Becnel J. Structure-activity relationship studies on derivatives of eudesmanolides from Inula helenium as toxicants against Aedes aegypti larvae and adults. Chem Biodivers. 2010;7:1681-97 pubmed publisher
    ..In addition, the crystal structures of both alantolactone and isoalantolactone were determined using CuK(alpha) radiation, which allowed their absolute configurations to be determined based on resonant scattering of the light atoms. ..
  57. Wu B, Wu L. [Advances in studies on chemical constituents of Senecio]. Zhongguo Zhong Yao Za Zhi. 2003;28:97-100 pubmed
    ..This article reviews the recent advances in chemical constituents, identification methods and pharmacological activities of it. ..
  58. Zini C, De Assis T, Ledford E, Dariva C, Fachel J, Christensen E, et al. Correlations between pulp properties of eucalyptus clones and leaf volatiles using automated solid-phase microextraction. J Agric Food Chem. 2003;51:7848-53 pubmed
    ..The potential of HS-SPME coupled to GC x GC to improve the separation of Eucalyptus volatiles and other plant essential oils looks extremely promising for new applications of unsupervised learning methods. ..
  59. Wu Q, Shi Y, Jia Z. Eudesmane sesquiterpenoids from the Asteraceae family. Nat Prod Rep. 2006;23:699-734 pubmed
    ..Biosynthetic studies or chemical syntheses leading to the revision of structures or stereochemistries have also been included, and 593 references are cited. ..
  60. Gavagnin M, Mollo E, Castelluccio F, Crispino A, Cimino G. Sesquiterpene metabolites of the antarctic gorgonian Dasystenella acanthina. J Nat Prod. 2003;66:1517-9 pubmed
    ..The structure elucidation of this new sesquiterpene was solved mainly on the basis of its spectral properties and correlation with known compounds. ..
  61. Grass S, Zidorn C, Ellmerer E, Stuppner H. Eudesmane derivatives from Hieracium intybaceum. Chem Biodivers. 2004;1:353-60 pubmed
    ..intybaceum. Structure elucidations were based on mass spectrometry and extensive 1D- and 2D-NMR spectroscopy. ..
  62. Dachriyanus -, Bakhtiar A, Sargent M, Skelton B, White A. rac-Eudesm-7(11)-en-4-ol. Acta Crystallogr C. 2004;60:o503-4 pubmed
    ..The structure was determined from spectroscopic data and a single-crystal X-ray study. Two similar independent molecules comprise the asymmetric unit of the structure. ..
  63. Morteza Semnani K, Saeedi M, Akbarzadeh M. Essential oil composition of Teucrium scordium L. Acta Pharm. 2007;57:499-504 pubmed publisher
    ..scordium. The major constituents of the oil were beta-caryophyllene (22.8%), (E)-beta-farnesene (10.4%), caryophyllene oxide (8.6%), 1,8-cineole (6.1%) and beta-eudesmol (5.1%)...
  64. Ma E, Li Y, Tsuneki H, Xiao J, Xia M, Wang M, et al. Beta-eudesmol suppresses tumour growth through inhibition of tumour neovascularisation and tumour cell proliferation. J Asian Nat Prod Res. 2008;10:159-67 pubmed publisher
    ..These results indicated that beta-eudesmol inhibited angiogenesis by suppressing CREB activation in growth factor signalling pathway. This is the first study to demonstrate that beta-eudesmol is an inhibitor of tumour growth. ..
  65. Stavri M, Mathew K, Gibson T, Williamson R, Gibbons S. New constituents of Artemisia monosperma. J Nat Prod. 2004;67:892-4 pubmed
    ..The absolute stereochemistry of 2 was determined using Mosher ester methodology in which the terminal primary hydroxyl group was first protected to simplify the stereochemical analysis. ..
  66. Kishi A, Morikawa T, Matsuda H, Yoshikawa M. Structures of new friedelane- and norfriedelane-type triterpenes and polyacylated eudesmane-type sesquiterpene from Salacia chinensis LINN. (S. prinoides DC., Hippocrateaceae) and radical scavenging activities of principal constituents. Chem Pharm Bull (Tokyo). 2003;51:1051-5 pubmed
    ..Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. Some norfriedelane-type triterpene, lignan, and catechin constituents were found to show radical scavenging activity...
  67. Garcia Granados A, Gutierrez M, Martinez A, Rivas F. Enzyme-catalyzed rearrangement of a diepoxy-germacrane compound into new 7-epi-eudesmane derivatives. J Org Chem. 2005;70:338-41 pubmed
  68. Zheng Q, Xu Z, Sun X, Yao W, Sun H, Cheng C, et al. Eudesmane and megastigmane glucosides from Laggera alata. Phytochemistry. 2003;63:835-9 pubmed
    ..Based on the chemical characteristics of eudesmane derivatives isolated from the Laggera genus, it was suggested that there are probably two different biogenetic pathways for these secondary metabolites in this genus. ..
  69. Abou Douh A. New eudesmane derivatives and other sesquiterpenes from the epigeal parts of Dittrichia graveolens. Chem Pharm Bull (Tokyo). 2008;56:1535-45 pubmed
    ..The antimicrobial, antiinflammatory, and antipyretic activities of D. graveolens extracts and chromatographic fractions were carried out and the various bioactivities of our findings are discussed. ..
  70. Garcia Granados A, Parra A, Rivas F, Segovia A. Seven-membered cyclic sulfite eudesmane derivatives: partial synthesis, structural determination, and enzymatic resolution. J Org Chem. 2007;72:643-6 pubmed
    ..This diastereomeric mixture was resolved by enzymatic acetylation with CCL. Each cyclic sulfite derivative was individually characterized on the basis of its spectroscopic and crystallographic properties. ..
  71. Garcia Granados A, Melguizo E, Parra A, Simeó Y, Viseras B, Dobado J, et al. Regioselective enzymatic acylations of polyhydroxylated eudesmanes: semisynthesis, theoretical calculations, and biotransformation of cyclic sulfites. J Org Chem. 2000;65:8214-23 pubmed
    ..While the R-sulfite gave 2 alpha- and 11 beta-hydroxylated metabolites, the S-sulfite yielded only regioselective deacetylations. Furthermore, both sulfites showed different reactivities in redox processes. ..
  72. Dai S, Shen L, Ren Y. Two new eudesmane-type sesquiterpenoids from Olanum lyratum. Nat Prod Res. 2009;23:1196-200 pubmed publisher
    ..In addition, two new compounds were found to show significant cytotoxicity against selected cancer cells in vitro, including P-388 and HT-29. ..
  73. Wang X, Gao X, Jia Z. Sesquiterpenoids from Lactuca tatarica. Fitoterapia. 2010;81:42-4 pubmed publisher
  74. Zhang L, Ouyang Z, Zhao M, Wang P, Fang J. [Simultaneous determination of atractylone, hinesol, beta-eudesmol, atrctylodin in Atractylodes lancea and hierarchical cluster analysis]. Zhongguo Zhong Yao Za Zhi. 2010;35:725-8 pubmed
    ..lancea, which will provide the basis for the quality control of A. lancea. The contents of 4 active compounds were significantly different between geo-authentic and non-authentic producing areas. ..
  75. Chaturvedula V, Farooq A, Schilling J, Malone S, Derveld I, Werkhoven M, et al. New eudesmane derivatives from Melampodium camphoratum from the Suriname rainforest. J Nat Prod. 2004;67:2053-7 pubmed
    ..using an assay for inhibitors of the degradation of hemin resulted in the isolation of six new eudesmane sesquiterpenes (1-6) and the known 6-epi-beta-verbesinol coumarate (7)...
  76. Yuan T, Zhang C, Yang S, Yin S, Wu W, Dong L, et al. Sesquiterpenoids and phenylpropanoids from Chloranthus serratus. J Nat Prod. 2008;71:2021-5 pubmed publisher
    ..The structure of a eudesmane-type sesquiterpene previously isolated from Chloranthus henryi was revised as its 4-epimer (3a). ..
  77. Petrichtcheva N, Duque C, Dueñas A, Zea S, Hara N, Fujimoto Y. New nitrogenous eudesmane-type compounds isolated from the Caribbean sponge Axinyssa ambrosia. J Nat Prod. 2002;65:851-5 pubmed
    ..Compound 1 exhibited significant cytotoxic activity against cancer cells and was also active in a lethality test using polyps of the scleractinian coral Madracis mirabilis. ..
  78. Ahmed A, Mahmoud A, Ali E, Tzakou O, Couladis M, Mabry T, et al. Two highly oxygenated eudesmanes and 10 lignans from Achillea holosericea. Phytochemistry. 2002;59:851-6 pubmed
    ..Two new highly oxygenated eudesmanes and 10 known lignans were isolated from the aerial parts of Achillea holosericea. Their structures were elucidated by extensive application of one- and two-dimensional 1H and 13C NMR spectroscopy. ..
  79. Zhang Z, Li W, Li Y. Novel approach for the stereocontrolled construction of eudesmane skeleton: a concise synthesis of (+/-)-balanitol. Org Lett. 2001;3:2555-7 pubmed
  80. Ahn J, Jang K, Chung S, Oh K, Shin J. Sorangiadenosine, a new sesquiterpene adenoside from the myxobacterium Sorangium cellulosum. Org Lett. 2008;10:1167-9 pubmed publisher
    ..The chemical structure of this compound was determined by combined spectroscopic and chemical analyses. The new compound exhibited moderate antibacterial activity against a wide range of bacterial strains. ..
  81. Karamenderes C, Bedir E, Pawar R, Baykan S, Khan I. Elemanolide sesquiterpenes and eudesmane sesquiterpene glycosides from Centaurea hierapolitana. Phytochemistry. 2007;68:609-15 pubmed
    ..Asteraceae). Structure elucidations were based on spectroscopic evidence. ..
  82. Song X, Tu P, Wu L, Cai Y, Zhu H, Lu Y, et al. A new sesquiterpene lactone from Tsoongiodendron odorum Chun. J Asian Nat Prod Res. 2001;3:285-91 pubmed
    ..Also, the cytotoxic ethyl acetate fraction of ethanol extract of the root barks from which three chemical components were isolated showed promising cytotoxic activities in vitro against KB, BGC-823, Bel-7402, HCT-8, HL-60 cell lines...
  83. Yang X, Wong M, Wang N, Chan A, Yao X. A new eudesmane derivative and a new fatty acid ester from Sambucus williamsii. Chem Pharm Bull (Tokyo). 2006;54:676-8 pubmed
    ..Both compounds 1 and 2 showed stimulating effects on alkaline phosphatase activity of the osteoblastic UMR106 cell about 1.5 fold at 30 mumol/l while they had no effects on cell proliferation. ..
  84. Liu Y, Jia W, Gao W, Zhao A, Zhang Y, Takaishi Y, et al. Two eudesmane sesquiterpenes from Laggera pterodonta. J Asian Nat Prod Res. 2006;8:303-7 pubmed
    The phytochemical study of the aerial parts of Laggera pterodonta afforded two new eudesmane sesquiterpenes, 3alpha,4beta,11-trihydroxyenantioeudesmane (pterodontriol E) (1) and 4beta,8beta,11-trihydroxyenantioeudesmane (pterodontriol F) (..
  85. Obara Y. [Development of anti-dementia drugs related to neurotrophic factors]. Yakugaku Zasshi. 2006;126:747-55 pubmed
    ..In addition, we discuss about the signaling pathway of nerve growth factor and cyclic AMP in order to seek the signaling molecules as targets of drug development. ..
  86. Ouyang Z, Yang L, Su S, Feng X, Wang M. [Fingerprint of volatile oil of Atractylodes lancea by GC-MS]. Yao Xue Xue Bao. 2007;42:968-72 pubmed
    ..dc. ..
  87. Chapman D, Holbrook D, Chaney S, Hall I, Lee K. In vitro inhibition of mouse hepatic mixed-function oxidase enzymes by helenalin and alantolactone. Biochem Pharmacol. 1989;38:3913-23 pubmed
    ..Instead, we suggest that STL binding to the substrate-binding site of cytochrome P-450 and subsequent metabolism of the STL may contribute to inhibition of the MFO system. ..
  88. El Gamal A. Sesquiterpene lactones from Smyrnium olusatrum. Phytochemistry. 2001;57:1197-200 pubmed
    ..The structure elucidation of the isolated compounds was based primarily on 1D and 2D NMR analyses. The in vitro cytotoxicity of the extract and isolated compounds against P-388 mouse lymphoma cells will be also discussed. ..