Stereochemistry of ptaquiloside, a novel norsesquiterpene glucoside from bracken, Pteridium aquilinum var. latiusculum

A biological hazard of our age: Bracken fern [ Pteridium aquilinum (L.) Kuhn] — A Review

“…3b). In 1983 two groups of scientists from Japan and from the Netherlands, respectively (Niwa et al, 1983;Van der Hoeven et al, 1983) isolated a compound with carcinogenic, mutagenic and clastogenic activity. The compound was termed ptaquiloside (PT).…”

Characteristics of Histamine Release from Rat Mast Cells Induced by a Bracken Toxin, Braxin A1

“…In view of the facts that plasma histamine (5) and heparin (5,6) are increased in cattle with the acute toxic disease, we have used histamine releasing activity as an index for the fractionation of the active principles (7)(8)(9)(10), and have isolated two novel gluco sides, named braxin Al and A2, from bracken rhizomes (11). It was suggested that braxin A2 changed from braxin Al during the isola tion procedures, and that both braxin Al and A2 have different chemical natures from ptaquiloside (12,13) isolated from bracken fronds as a carcinogen. Recently, it has been shown that braxin Al induces bracken poisoning in guinea pigs, characterized by a marked edema and hemorrhage within 24 to 48 hours in the urinary bladder (14).…”

Occurrence, Structure and Taxonomic Implications of Fern Constituents

“…As the carcinogen was quite unstable and its acute toxicity in small test animals was not obvious, the causative principles were not known until recently, in spite of intensive studies conducted by many workers (311,312,313,314,463). In 1983, YAMADA et al (278,279) isolated ptaquiloside (466) from bracken and identified it as the causative of bracken poisoning (315) and carcinogenicity (316). Its structure (466) was determined by X-ray analysis (279).…”

“…In 1983, YAMADA et al (278,279) isolated ptaquiloside (466) from bracken and identified it as the causative of bracken poisoning (315) and carcinogenicity (316). Its structure (466) was determined by X-ray analysis (279). In 1983, VAN DER HOEVEN and LEEUVEN (280, 281) isolated a mutagenic compound from a methanol extract of bracken, named it aquilide A, and assigned it structure 466.…”