Collect. Czech. Chem. Commun.
1962, 27, 2654-2661
https://doi.org/10.1135/cccc19622654
On terpenes. CXLV. Constitution of eupatoriopicrin, a germacranolide from Eupatorium cannabinum L.
L. Dolejš and V. Herout
Crossref Cited-by Linking
- Yamazaki Hiroyuki, Tsuge Hayato, Takahashi Ohgi, Uchida Ryuji: Germacrane sesquiterpenes from leaves of Eupatorium chinense inhibit protein tyrosine phosphatase. Bioorganic & Medicinal Chemistry Letters 2021, 53, 128422. <https://doi.org/10.1016/j.bmcl.2021.128422>
- Saito Yoshinori, Mukai Tomomi, Iwamoto Yuko, Baba Makiko, Takiguchi Koji, Okamoto Yasuko, Gong Xun, Kawahara Takayuki, Kuroda Chiaki, Tori Motoo: Germacranolides and Their Diversity of Eupatorium heterophyllum Collected in P. R. China. Chem. Pharm. Bull. 2014, 62, 1092. <https://doi.org/10.1248/cpb.c14-00426>
- Saito Yoshinori, Matsuo Sachie, Sutoyo Suyatno, Tori Motoo: Nine New Norlabdane Diterpenoids from the Leaves of Austroeupatorium inulifolium. Helvetica Chimica Acta 2011, 94, 313. <https://doi.org/10.1002/hlca.201000207>
- Saito Yoshinori, Takiguchi Koji, Gong Xun, Kuroda Chiaki, Tori Motoo: Thiophene, Furans, and Related Aromatic Compounds from Eupatorium heterophyllum. Natural Product Communications 2011, 6. <https://doi.org/10.1177/1934578X1100600312>
- Tori Motoo, Morishita Norie, Hirota Naoko, Saito Yoshinori, Nakashima Katsuyuki, Sono Masakazu, Tanaka Masami, Utagawa Akiko, Hirota Hiroshi: Sesquiterpenoids Isolated from Eupatorium glehnii. Isolation of Guaiaglehnin A, Structure Revision of Hiyodorilactone B, and Genetic Comparison. Chem. Pharm. Bull. 2008, 56, 677. <https://doi.org/10.1248/cpb.56.677>
- Tori Motoo, Takeichi Yoshiko, Kuga Hiroe, Nakashima Katsuyuki, Sono Masakazu: Seven Germacranolides, Eupaglehnins A, B, C, D, E, and F, and 2α-Acetoxyepitulipinolide from Eupatorium glehni. Chem. Pharm. Bull. 2002, 50, 1250. <https://doi.org/10.1248/cpb.50.1250>
- Herz Werner: Chemistry of the eupatoriinae. Biochemical Systematics and Ecology 2001, 29, 1115. <https://doi.org/10.1016/S0305-1978(01)00056-4>
- Meragelman Karina M., Espinar Luis Ariza, Sosa Virginia E., Uriburu María L., de la Fuente Juana R.: Terpenoid constituents of Viguiera tucumanensis. Phytochemistry 1996, 41, 499. <https://doi.org/10.1016/0031-9422(95)00584-6>
- Jeske F., Huneck S., Jakupovic J.: Further sesquiterpene lactones from Inula salsoloides. Phytochemistry 1996, 41, 1539. <https://doi.org/10.1016/0031-9422(95)00807-1>
- Zdero C., Bohlmann F., Anderberg A., King R.M.: Eremophilane derivatives and other constituents from Haeckeria species and further Australian inuleae. Phytochemistry 1991, 30, 2643. <https://doi.org/10.1016/0031-9422(91)85114-F>
- Zdero C., Bohlmann F., King R.M.: A cyclopropanoheliangolide and guaianolides from cronquistia pringlei. Phytochemistry 1991, 30, 909. <https://doi.org/10.1016/0031-9422(91)85277-7>
- Kotov A. G., Darmograi R. E., Rosik G. G., Komissarenko N. F., Ladnaya L. Ya.: Sesquiterpene lactones of Eupatorium cannabinum. Chem Nat Compd 1990, 26, 345. <https://doi.org/10.1007/BF00597871>
- Zdero C., Bohlmann F., King R.M.: Eudesmane derivatives other constituents fromApalochlamys spectabilis Cassinia species. Phytochemistry 1990, 29, 3201. <https://doi.org/10.1016/0031-9422(90)80185-J>
- Zdero C., Bohlmann F., Niemeyer H.M.: Seco-labdanes and other constituents fromOphryosporus floribundus. Phytochemistry 1990, 29, 3247. <https://doi.org/10.1016/0031-9422(90)80193-K>
- Jolad Shivanand D., Hoffmann Joseph J., Timmermann Barbara N., Bates Robert B., Camou Fernando A., Mclaughlin Steven P.: Guaianolides from Pericome caudata. Phytochemistry 1990, 29, 649. <https://doi.org/10.1016/0031-9422(90)85136-4>
- Zdero C., Bohlmann F., Niemeyer H.M.: A heliangolide, 3-hydroxyumbelliferone derivatives and diterpenes from Bahia ambrosioides. Phytochemistry 1990, 29, 205. <https://doi.org/10.1016/0031-9422(90)89037-A>
- Pérez Ana-Lidia, de Vivar Alfonso Romo: Triacyl glu-copyranoses from Bahia schaffneri. Phytochemistry 1989, 28, 1639. <https://doi.org/10.1016/S0031-9422(00)97816-6>
- Zdero C., Bohlmann F., King R.M., Robinson H.: The first 12.8β-germacrolide and other constituents from bolivian Stevia species. Phytochemistry 1988, 27, 2835. <https://doi.org/10.1016/0031-9422(88)80673-3>
- Tamayo-Castillo G., Jakupovic J., Bohlmann F., Rojas A., Castro V., King R.M.: Germacranolides and other constituents from Ageratina species. Phytochemistry 1988, 27, 2893. <https://doi.org/10.1016/0031-9422(88)80683-6>
- Perez Ana-Lidia, Ortega Alfredo, De Vivar Alfonso Romo: An acyclic diterpene and sesquiterpene lactones from Tithonia pedunculata. Phytochemistry 1988, 27, 3897. <https://doi.org/10.1016/0031-9422(88)83040-1>
- Domi´nguez X.A., Sa´nchez H., Slim J., Jakupovic J., Chau-Thi T.V., Bohlmann F.: Eupatolide and borneol derivatives from Florestina tripteris. Phytochemistry 1988, 27, 613. <https://doi.org/10.1016/0031-9422(88)83154-6>
- Zdero C., Bohlmann F., Dillon M.O.: Helogynic acid, a homoditerpene, and other constituents from Helogyne apaloidea. Phytochemistry 1988, 27, 616. <https://doi.org/10.1016/0031-9422(88)83155-8>
- Woerdenbag H. J.: Eupatorium cannabinum L. Pharmaceutisch Weekblad Scientific Edition 1986, 8, 245. <https://doi.org/10.1007/BF01960068>
- Pfeil Richard M., Gage Douglas A., Lee Esther F., Miski Mahmut, Mabry Tom J., Powell A.Michael: Sesquiterpene lactones from Perityle vaseyi. Phytochemistry 1986, 26, 195. <https://doi.org/10.1016/S0031-9422(00)81510-1>
- Schmeda-Hirschmann G., Zdero C., Baruah R.N., Bohlmann F.: Further sesquiterpene lactones from Calea and Viguiera species. Phytochemistry 1985, 24, 2019. <https://doi.org/10.1016/S0031-9422(00)83114-3>
- Harmatha Juraj, Nawrot Jan: Comparison of the feeding deterrent activity of some sesquiterpene lactones and a lignan lactone towards selected insect storage pests. Biochemical Systematics and Ecology 1984, 12, 95. <https://doi.org/10.1016/0305-1978(84)90015-2>
- Kasymov Sh. Z.: Advances in the chemistry of sesquiterpene lactones. Chem Nat Compd 1982, 18, 519. <https://doi.org/10.1007/BF00575031>
- Seaman Frederick C.: Sesquiterpene lactones as taxonomic characters in the asteraceae. Bot. Rev 1982, 48, 121. <https://doi.org/10.1007/BF02919190>
- Watanabe Keisuke, Ohno Nobuo, Yoshioka Hirosuke, Gershenzon Jonathan, Mabry Tom J.: Sesquiterpene lactones and diterpenoids from Helianthus argophyllus. Phytochemistry 1982, 21, 709. <https://doi.org/10.1016/0031-9422(82)83171-3>
- Bohlmann Ferdinand, Zdero Christa: Neue sesquiterpenlactone und thymol-derivate aus Inula-arten. Phytochemistry 1977, 16, 1243. <https://doi.org/10.1016/S0031-9422(00)94366-8>
- Pedersen Erling: Echinatine and supinine: Pyrrolizidine alkaloids from Eupatorium cannabinum. Phytochemistry 1975, 14, 2086. <https://doi.org/10.1016/0031-9422(75)83136-0>
- Lee Kuo-Hsiung, Furukawa Hiroshi, Huang Huan-Chang, Huang Eng-Shang: Antitumor Agents II: Eupatolide, a New Cytotoxic Principle from Eupatorium formosanum HAY. Journal of Pharmaceutical Sciences 1972, 61, 629. <https://doi.org/10.1002/jps.2600610432>
- Geissman T.A., Griffin T.S.: Sesquiterpene lactones: Acid-catalysed color reactions as an aid in structure determination. Phytochemistry 1971, 10, 2475. <https://doi.org/10.1016/S0031-9422(00)89894-5>
- Geissman T.A., Atala Samy: Distribution of eupatoriopicrin in compositae. Phytochemistry 1971, 10, 1075. <https://doi.org/10.1016/S0031-9422(00)89941-0>
- Stöcklin W., Waddell T.G., Geissman T.A.: Circular dichroism and optical rotatory dispersion of sesquiterpene lactones. Tetrahedron 1970, 26, 2397. <https://doi.org/10.1016/S0040-4020(01)92818-2>
- McCorkindale N.J., Wright J.L.C., Brian P.W., Clarke S.M., Hutchinson S.A.: Canadensolide - an antifungal metabolite of penicillium canadense. Tetrahedron Letters 1968, 9, 727. <https://doi.org/10.1016/S0040-4039(00)75621-8>
- Kupchan S.Morris, Kelsey John E., Sim G.A.: The stereochemistry of germacranolide sesquiterpenes. Tetrahedron Letters 1967, 8, 2863. <https://doi.org/10.1016/S0040-4039(00)90875-X>