Chingazumianine, a Novel Dichlorinated Alkaloid fromCorydalis koidzumiana

Abstract

A dichlorinated alkaloid with a novel skeleton, chingazumianine (1), was isolated from the herb Corydalis koidzumiana, and its structure elucidated by spectroscopic data and X-ray crystallographic analysis. In citratetreated human platelet-rich plasma (PRP), known compounds, i.e., protopine (2), (AE)-tetrahydropalmatine (3), and palmatine (4), isolated from this plant, showed significant inhibition of secondary aggregation induced by adrenaline in a concentration-dependent manner, suggesting that the antiplatelet effects of these compounds is mainly due to an inhibitory effect on thromboxane formation.

Discovery and Synthesis of Caracolamide A, an Ion Channel Modulating Dichlorovinylidene Containing Phenethylamide from a Panamanian Marine Cyanobacterium cf. Symploca Species

“…The presence of such an atypical functional group, particularly among plant natural products, may in some cases be an experimental artifact. Chloroform can form a reactive dichlorocarbene species under certain conditions and lead to the formation of gem -dichlorovinylidene moieties . However, marine natural products, such as the taveunamides, mutafuran, ( Z )- and ( E )-antazirine, and several analogous azirinecarboxylates that were isolated from the sponge Dysidea fragilis , have been shown to contain gem -dihalovinylidene moieties comprising only bromine or chlorine or atoms of each element, thus supporting their natural biosynthetic origins. , …”

“…Chloroform can form a reactive dichlorocarbene species under certain conditions and lead to the formation of gem-dichlorovinylidene moieties. 12 However, marine natural products, such as the taveunamides, mutafuran, (Z)-and (E)-antazirine, and several analogous azirinecarboxylates that were isolated from the sponge Dysidea f ragilis, have been shown to contain gem-dihalovinylidene moieties compris- ing only bromine or chlorine or atoms of each element, thus supporting their natural biosynthetic origins. 4,13 Chemical profiling of extracts produced from 10 morphologically identified Symploca spp., comprising two fieldidentified collections from American Samoa, one from Saipan, six from Panama, and one grown in the laboratory from the Pasteur Culture Collection (PCC8002), was achieved using LC-MS/MS and molecular networking untargeted metabolomics (Figure 1, A).…”