XLII.—Gynocardin, a new cyanogenetic glucoside

Abstract

X LII.-(2 ynocadiu, cc New Cyanogenet ic Glucoside. By FREDERICK BELDING POWER and FREDERIC HERBERT LEES, IN a preliminary note it was recorded by one of us and F. H. Gornall (Proc., 1904, 20, 137) that when the seeds of Gynocardicc ocloratcc (R. Br.) were crushed and brought into contact with water, a strong odour of hydrogen cyanide was developed, and this behaviour was shown to be due to the presence of ft cyanogenetic glucoside, which was isolated and designated g9nocardin. Since then we have been able to procure a large quantity of gynocardia seeds, which were specially collected for us in India, and have succeeded in isolating gynocardin in a pure stste and in ail amount sufficient t o admit of its further study. The yield of this substance w a s equal to 5 per cent. of the weight of the seeds.

Constitutive polymorphic cyanogenesis in the Australian rainforest tree, Ryparosa kurrangii (Achariaceae)

“…This result is in concordance with an examination of Ryparosa acuminata seed tissue, in which 1 was the only documented cyanogen (Spencer and Seigler, 1985a). Gynocardin, the first cyclopentenoid glycoside to be discovered (Power and Gornall, 1904;Power and Barrowcliff, 1905;Power and Lees, 1905) and have its chemical structure determined (Coburn and Long, 1966;Kim et al, 1970), is the most common glycoside found in Achariaceae taxa, and has been isolated from leaf, stem, root, pericarp and seed tissue (e.g. Spencer and Seigler, 1985a;Jensen and Nielsen, 1986).…”

The structures of cyclopentenyl fatty acids in the seed oils of flacourtiaceae species by GC‐MS of their 4,4‐dimethyloxazoline derivatives

“…Methyl ester of hydnocarpic acid. The methyl ester of hydnocarpic acid, 16:1(cy), was isolated from the seed oil of H. anthelmintica according to a procedure described in the literature (13). The crude acid was converted to its methyl ester and then subjected to preparative GLC (PGLC) (column conditions: SE-30, 160-220 C, programmed at 5 C/min) to afford the pure methyl ester.…”

Chemical Diversity of Plant Cyanogenic Glycosides: An Overview of Reported Natural Products

“…Gynocardin ( 48 ) ( Figure 9 ), the so far only cyclopentene derivative featuring three hydroxy moieties in the cyclopentene part of the molecule, was isolated from Gynocardia odorata R.Br. (Achariaceae) [ 37 ].…”

“…This group currently comprises 20 compounds. The first compound reported from this group was gynocardin (48), described in 1905 [37]. The latest one is passiguatemalin (53), reported in 2002 [38].…”

“…Volkenin (36) was originally isolated from Adenia volkensii Harms (Passifloraceae) as epitetraphyllin B [42], but later renamed volkenin [43]. Volkenin sulfate (37) and tetraphyllin B sulfate (46) were isolated from Passiflora caerulea L. (Passifloraceae) [44]. Taraktophyllin (38) and epivolkenin/passicoriacin (40) were isolated from Passiflora coriacea Juss.…”