The isolation and structure elucidation of a new sesquiterpene lactone from the poisonous plant Coriaria japonica (Coriariaceae)

Chemical and Pharmaceutical Bulletin

Volumn 53, Issue 8, 2005, Pages 1040-1042

  Kinoshita, Takeshi ^a   Itaki, Nao ^b   Hikita, Maho ^b   Aoyagi, Yutaka ^b   Hitotsuyanagi, Yukio ^b   Takeya, Koichi ^b  

^a TEIKYO UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Coriaria japonica; Coriariaceae; Poisonous plant; Sesquiterpene lactone

Indexed keywords

CORIANIN; CORIARIA JAPONICA EXTRACT; CORIARIN; DIHYDROTUTIN; PLANT EXTRACT; SESQUITERPENE LACTONE DERIVATIVE; TUTIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL COMPOSITION; CHEMICAL REACTION; CORIARIA JAPONICA; DRUG ISOLATION; DRUG STRUCTURE; MEDICINAL PLANT; PLANT SEED; STRUCTURE ANALYSIS;

ANGIOSPERMS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLANTS, TOXIC; SESQUITERPENES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED;

EID: 24944446348     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.53.1040     Document Type: Article

References (12)

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9. The finding that the sarcocarp extract contains no toxic principles was also supported by a toxicity experiment using mice (T. Kinoshita, unpublished data). The sarcocarp extract consisted predominantly of polyphenols, as is the case for other ordinary black berries. We did not proceed further since it had nothing to do with the goal of this research.
10. A search of the literature in the CAS database for the following structural name (spiro[indan-1,2′-oxirane]-4-carboxylic acid, 2,3-epoxyhexahydro-3a,6,7-trihydroxy-5-isopropenyl-7a-methyl-, γ-lactone) led to us finding the following literature: Okuda T., Yoshida T., Tetrahedron Lett., 1965, 4191-4197 (1965). However, there was no description concerning the corresponding compound in this paper. In the subsequent full paper of this article by the same authors, a compound structurally corresponding to a dihydro form of coriarin, that is, spiro[indan-1,2′-oxirane]-4-carboxylic acid, 2,3-epoxyhexahydro-3a,6,7-trihydroxy-5-isopropyl-7a-methyl-, γ-lactone, was described as an intemediate compound in the course of chemical correlation between coriamyrtin and tutin. Perhaps, what was found as spiro[indan-1, 2′-oxirane]-4-carboxylic acid, 2,3-epoxyhexahydro-3a,6,7-trihydroxy-5- isopropenyl-7a-methyl-, γ-lactone in the CAS database will be counted as one of the possible candidates for the structure of tutin and thus has no corporeality. Therefore, coriarin (1) is a new compound from not only natural sources but also artificial products.
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