- Total synthesis of cynaropicrin
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Cynaropicrin is found in artichoke (Cynara scolymus) and is the source of its bitter taste and it is a sesquiterpene lactone with a 5-7-5 tricyclic skeleton, six chiral centers, and fourexo-olefins. This natural product has numerous attractive biological activities including the inhibition of NF-κB activation, antihepatitis C activity, and antitrypanosomal activity. In this study, the first total synthesis of cynaropicrin was achieved starting from (S)-α-pinene. The synthesis involved a stereoselective Favorskii rearrangement and an indium-promoted diastereoselective Barbier reaction.
- Egoshi, Yuki,Hara, Shihori,Kimura, Kogaku,Kondo, Ryosuke,Mori, Takaya,Nakamura, Tenma,Pitna, Dinda B.,Suzuki, Noriyuki,Suzuki, Yumiko,Uchiyama, Tomoya,Usuki, Toyonobu,Yamaguchi, Shoya,Yoshimoto, Yukiko
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- Synthesis of cynaropicrin-d4
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Cynaropicrin is a guaianolide sesquiterpene lactone, which has potent in vitro and in vivo inhibitory activity against Trypanosoma brucei, the protozoan parasite that causes human African trypanosomiasis (HAT; sleeping sickness). Herein, we describe the synthesis of cynaropicrin's deuterated derivative, cynaropicrin-d4, by the replacement of the side chain of natural cynaropicrin. The synthesized cynaropicrin-d4 could be employed as an internal standard for liquid chromatography-mass spectrometry (LC-MS) analysis, in the pharmacokinetic study of cynaropicrin. This could potentially advance the study of this therapeutic lead.
- Sato, Takuya,Hara, Shihori,Sato, Makiko,Ogawa, Keita,Adams, Michael,Usuki, Toyonobu
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p. 5504 - 5507
(2015/11/18)
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- SESQUITERPENE LACTONES IN MONGOLIAN Saussurea lipshitzii
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Five known guaianolides were isolated from the areal part of Saussurea lipshitzii (Asteraceae) collected in South Gobi, Mongolia: cynaropicrin (I), janerin (II), chlorojanerin (III), 15-deschloro-15-acetoxychlorojanerin (IV), and 15-deschloro-15-hydroxychlorojanerin (V).The correlation between I-V and the β-configuration of the C-4/C-15 bond in II-V was shown by biomimetic chemical transformations, suggesting compound I as the possible common precursor.
- Todorova, Milka N.,Ognyanov, Iliya V.,Shatar, Sanduin
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p. 1106 - 1109
(2007/10/02)
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