13,14-dihydrocoptisine--the genuine alkaloid from Chelidonium majus.

Abstract:

:The genuine major benzylisoquinoline alkaloid occurring in the traditional medicinal plant greater celandine (Chelidonium majus L.) is 13,14-dihydrocoptisine and not - as described previously - coptisine. Structure of 13,14-dihydrocoptisine was elucidated. The discrepancy between the alkaloid pattern of the living plants and that of detached and dried leaves is due to the rapid and prompt conversion of 13,14-dihydrocoptisine to coptisine in the course of tissue injuries. Indeed, apart from the major alkaloid, some minor alkaloids might also be converted; this however is not in the centre of focus of this paper. This conversion is initiated by the change of pH. In vivo 13,14-dihydrocoptisine is localized in the acidic vacuoles, where it is stable. In contrast, in the neutral milieu, which results when vacuoles are destroyed in the course of tissue injuries, the genuine alkaloid is oxidized to yield coptisine. Accordingly, when alkaloids from C.majus should be analyzed, any postmortal conversion of 13,14-dihydrocoptisine has to be prevented.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Paulsen J,Yahyazadeh M,Hänsel S,Kleinwächter M,Ibrom K,Selmar D

doi

10.1016/j.phytochem.2015.01.006

subject

Has Abstract

pub_date

2015-03-01 00:00:00

pages

149-53

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(15)00041-2

journal_volume

111

pub_type

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