107439-71-4Relevant academic research and scientific papers
Antimycobacterial eudesmanolides from Inula helenium and Rudbeckia subtomentosa
Cantrell, Charles L.,Abate, Laura,Fronczek, Frank R.,Franzblau, Scott G.,Quijano, Leovigildo,Fischer, Nikolaus H.
, p. 351 - 355 (1999)
In a bioassay guided search for antimycobacterial compounds from higher plants, the root extracts of Elecampane (Inula helenium L.; Asteraceae) and Sweet Coneflower (Rudbeckia subtomentosa Pursh.; Asteraceae) were chemically investigated for their active constituents. Chromatographic fractions of root extracts of I. helenium, which exhibited significant activity against Mycobacterium tuberculosis, provided the known eudesmanolides alantolactone, isoalantolactone, and 11αH,13-dihydroisoalantolactone. Peracid epoxidation of alantolactone and isoalantolactone provided 5α-epoxyalantolactone and 4(15)α-epoxyisoalantolactone, respectively and oxidation of alantolactone with OsO4 gave 11,13-dihydroxyalantolactone. Active fractions from R. subtomentosa contained the known alloalantolactone and 3- oxoalloalantolactone. The structures of the above compounds were established by spectroscopic methods including 1D and 2D NMR techniques as well as spectral comparison with previously reported data. The molecular structure of 5α-epoxyalantolactone was determined by single crystal X-ray diffraction. Eleven natural and semisynthetic eudesmanolides were tested in a radiorespirometric bioassay for activity against M. tuberculosis. 5α- Epoxyalantolactone and encelin from Montanoa speciosa showed minimum inhibitory concentrations (MICs) of 8 and 16 μg ml-1, respectively. Alantolactone, isoalantolactone and its 4α,15-epoxide, 1,2-dehydro-3-epi- isotelekin and alloalantolactone gave MICs of 32 μg ml-1. All other compounds showed MIC values of 128 μg ml-1 or higher.
Epoxidation of alantolactone and isoalantolactone
Kulyyasov,Seitembetov,Turdybekov,Adekenov
, p. 869 - 872 (1996)
Alantolactone and isoalantolactone have been epoxidized with peracetic, m-chloroperbenzoic, and trifluoroperacetic adds. The structure of 4(15)-α-epoxyisoalactone has been established by an x-ray structural investigation.
Synthesis and discovery of a drug candidate for treatment of idiopathic pulmonary fibrosis through inhibition of TGF-β1 pathway
Li, Xiaohe,Lu, Cheng,Liu, Shuangwei,shuaishuai Liu,Su, Chengcheng,Xiao, Ting,Bi, Zhun,Sheng, Pengzhen,Huang, Mengying,Liu, Xinhua,Wei, Yujiao,Zhao, Lin,Miao, Shengxiang,Mao, Jiahe,Huang, Kai,Gao, Shaoyan,Liu, Ning,Qi, Min,Liu, Tongtong,Qin, Shuanglin,Wei, Luqing,Sun, Tao,Ning, Wen,Yang, Guang,Zhou, Honggang,Yang, Cheng
, p. 229 - 247 (2018)
In this study, anti-IPF lead compounds 42 and 44, derived from natural sesquiterpene lactones Isoalantolactone and alantolactone, were discovered by screening from a high-throughput TGF-β1 reporter luciferase assay. Notably, they could reduce the myofibroblast activation and extracellular matrix deposition both in vitro and in vivo. Additionally, compounds 42 and 44 could significantly attenuate bleomycin-induced pulmonary fibrosis in mice. Further validation of pharmacokinetics study and toxicity evaluation indicated that compound 44 might be a promising anti-IPF drug candidate.
EPOXY ALANTOLIDES: ISOINUNAL-A NEW POTENT PLANT GROWTH REGULATOR FROM INULA RACEMOSA
Kalsi, P. S.,Goyal, Rita,Talwar, K. K.,Chhabra, B. R.
, p. 2079 - 2082 (1988)
An investigation of Inula racemosa roots afforded, in addition to known sesquiterpene lactones, four new lactones with close biogenetic relationships.Their structures have been elucidated using spectral data and chemical correlation.The most interesting of these is isoinunal which is a potent root initiator with hypocotyl cuttings of Phaseolus aureus.Key Word Index-Inula racemosa; Compositae; alantolides; plant growth regulators; biogenesis; α-methylene-γ-lactone.
NEW SESQUITERPENE LACTONES, GERANYLLINALOL DERIVATIVES AND OTHER CONSTITUENTS FROM GEIGERIA SPECIES
Bohlmann, Ferdinand,Zdero, Christa,Ahmed, Maniruddin
, p. 1679 - 1692 (1982)
The investigation of three Geigeria species and five subspecies afforded, in addition to known compounds, the following 32 new compounds: two geigeranolides with a new carbon skeleton, two xanthanolides, five guaianolides, three pseudoguaianolides, a sesquiterpene related to ivaxillarin, a nerolidol derivative, 15 geranyllinalol derivatives, two thiophene acetylenes and a dimeric coniferyl isobutyrate.The structures and the stereochemistry of the new compounds were elucidated by spectroscopic methods and a few chemical transformations.Chemotaxonomic aspects and relationships of the compounds are discussed. - Key Word Index: Geigeria aspera; G. brevifolia; G. burkei subsp.; Compositae; Inuleae; sesquiterpene lactones; guaianolides; pseudoguaianolides; xanthanolides; geigeranolides; diterpenes; geranyllinalol derivatives; thiophene acetylenes; nerolidol derivative; new carbon skeleton.
Sesquiterpene lactone nitrogen methyl piperazine derivative and salt thereof, and application thereof in medicine preparation
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Paragraph 0032-0033, (2021/05/01)
The invention relates to sesquiterpene lactone nitrogen methyl piperazine derivatives and pharmaceutically acceptable salts thereof, and applications thereof in medicine preparation. The invention concretely relates to compounds represented by formulas (I), (II), (III) and (IV), and pharmaceutically acceptable salts thereof, as well as the applications of the compounds shown in formulas (I), (II), (III) and (IV) and pharmaceutically acceptable salts and compositions thereof for preparing anti-cancer or auxiliary anti-cancer drugs.
Synthesis and Cytotoxic Activity of the Products of Addition of Thiophenol to Sesquiterpene Lactones
Anikina, L. V.,Klochkov, S. G.,Semakov, A. V.
, p. 906 - 917 (2021/08/25)
Abstract—: Derivatives of sesquiterpene lactones modified at the lactone ring with a thiophenol residue have been synthesized. The resulting conjugates with thiophenol have capacity for the oxidation–elimination reaction by the action of ROS of a tumor cell with the release of initial cytotoxic lactones. It has been proposed to use the resulting sulfur-containing conjugates as ROS-activated prodrugs of sesquiterpene lactones. The antiproliferative properties of the conjugates have been examined on tumor and pseudonormal cell lines. The cytotoxicity of the conjugates is lower than that of parent lactones; however, in some cases, as with the conjugates of alantolactone with artemisiten, it remains moderate in all tumor cell lines tested.
Alantolactone derivative and application of derivative salt to preparation of drugs for treating inflammatory bowel diseases
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Paragraph 0029; 0032; 0033; 0034, (2017/08/28)
The invention provides an alantolactone derivative and an application of derivative salt to preparation of drugs for treating inflammatory bowel diseases. The alantolactone derivative is as shown in a formula (I-II) or (I-III). According to the alantolactone derivative, acid forming the salt is inorganic acid or organic acid, the inorganic acid is selected from hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, carbonic acid, boracic acid, seleninic acid, phosphomolybdic acid, phosphorous acid and sulfurous acid, the organic acid is selected from citric acid, maleic acid, D-malic acid, L-malic acid, DL-malic acid, L-lactic acid, D-lactic acid, DL-acid, oxalic acid, methanesulfonic acid, valeric acid, oleic acid, lauric acid, p-toluene sulfonic acid, 1-naphthalene sulfonic acid, 2-naphthalene sulfonic acid, phthalic acid, tartaric acid, malonic acid, succinic acid, fumaric acid, glycollic acid, thioglycollic acid, glycine, sarcosine, sulfonic acid, nicotinic acid, picoline acid, isonicotinic acid and benzoic acid or substituted benzoic acid.
Application of alantolactone derivative and salt thereof in preparing drug for treating thyroiditis
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Paragraph 0028; 0031; 0032; 0033, (2017/08/28)
The invention relates to application of an alantolactone derivative and salt thereof in preparing a drug for treating thyroiditis, and provides application of the alantolactone derivative as the formula (I-II) or the formula (I-III) and the salt thereof in preparing the drug for treating thyroiditis. Acid for forming the salt is inorganic or organic acid, the inorganic acid is selected from hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, carbonic acid, boracic acid, seleninic acid, phosphomolybdic acid, phosphorous acid and sulphurous acid, and the organic acid is selected from citric acid, maleic acid, D-malic acid, L-malic acid, DL-malic acid, L-lactic acid, D-lactic acid, DL-lactic acid, oxalic acid, methanesulfonic acid, pentanoic acid, oleic acid, lauric acid, p-methylbenzene sulfonic acid, 1-naphthalene sulfonic acid, 2-naphthalene sulfonic acid, phthalic acid, tartaric acid, malonic acid, succinic acid, fumaric acid, glycollic acid, mercaptan acid, glycine, sarcosine, sulfonic acid, nicotinic acid, methylpyridine, isonicotinic acid, benzoic acid and substituted benzoic acid.
Alantolactone derivative and salts thereof
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Paragraph 0033; 0034; 0035, (2017/08/28)
The invention provides an alantolactone derivative shown as formula (I). The acid for salt forming is inorganic acid or organic acid, the inorganic acid is selected from hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydriodic acid, sulfuric acid, nitric acid, phosphoric acid, carbonic acid, boric acid, seleninic acid, phosphomolybdic acid, phosphorous acid and sulfurous acid, and the organic acid is selected from citric acid, maleic acid, D-malic acid, L-malic acid, DL-malic acid, L-lactic acid, D-lactic acid, DL-acid, oxalic acid, methanesulfonic acid, pentanoic acid, oleic acid, lauric acid, p-toluene sulfonic acid, 1-naphthalene sulfonic acid, 2-naphthalene sulfonic acid, phthalic acid, tartaric acid, malonic acid, succinic acid, fumaric acid, glycollic acid, mercaptan acid, glycine, sarcosine, sulfonic acid, nicotinic acid, methylpyridine acid, isonicotinic acid, benzoic acid or substituted benzoic acid.
