Cyclopentanoid Cyanohydrin Glucosides and Amides ofLindackeria dentata

Abstract

A mixture of cyanogenic glucosides epivolkenin and taraktophyllin, 1,4-dihydroxy-2-cyclopentenecarboxamide, and uridine were isolated from leaves of Lindackeria dentata (Flacourtiaceae). Another cyclopentanoid amide, (1 R,4 S,5 R)-1,4,5-trihydroxy-2-cyclopentenecarboxamide, was synthesized in two steps from gynocardin, and shown to have the same relative configuration as a partially identified amide previously isolated from L. dentata bark.

Synthesis and Characterisation of α‐Glycosyloxyamides Derived from Cyanogenic Glycosides

“…Although these differences overcome usual solvent‐caused resonance variation and were also observed for the pairs of acalyphin/acalyphinamide (Hungeling et al ., 2009), lucumin/lucuminamide (Takeda et al ., 1997), gynocardin/gynocardinamide (Jaroszewski et al ., 2004), volkenin/volkeninamide (Jaroszewski et al ., 1987) and tetraphyllin‐B/tetraphyllin‐B‐amide (Jaroszewski at al., 1987), they do not allow an unambiguous proof of the primary amide moiety. This is especially due to the possible presence of the corresponding carboxylic acids which have been repeatedly found in cyanogenic plants (Kitajima and Tanaka, 1993; Takeda et al ., 1997; D'Abrosca et al ., 2001; Fukuda et al ., 2003) and are hardly distinguishable from the corresponding amides by the NMR characteristics mentioned above.…”

“…The in‐vitro conversion of cyanogenic glycosides into their corresponding amides using concentrated ammonia to hydrolyse the nitrile moiety has been previously reported (Turczan et al ., 1978; Takeda et al ., 1997; Jaroszewski et al ., 2004). However, with this method, the corresponding acids are formed as a major by‐product besides the low amount of the primary amides (Turczan et al.…”

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

“…epivolkenin, taraktophyllin, deidaclin) have been identified in Achariaceae (e.g. Jaroszewski et al, , 2004, and it appears that there may be spatial separation at an organ level between different cyanogenic compounds. For example, gynocardin and epivolkenin were detected in Lindackeria dentata (Oliv.)…”

“…For example, gynocardin and epivolkenin were detected in Lindackeria dentata (Oliv.) Gilg seeds (Spencer and Seigler, 1985a;Seigler and Spencer, 1989), while epivolkenin and taraktophyllin were isolated from leaf material of the same species (Jaroszewski et al, 2004). Further chemical purification of cyanogens from different tissue types and taxa within Ryparosa would be required to test if gynocardin is the only cyanogenic glycoside in the genus.…”

Saponin-rich extracts reverse obesity and offer protection against obesity-induced inflammation in high-fat diet mice

“…Lindackeria dentata (Oliv.) Gilg is a plant of 16 meters tall, which belongs to the family of Flacourtiaceae (Burkill 1985;Jaroszewski, Ekpe & Witt 2004). It is known in Nigeria as 'Igbo Oru Burkill' (1985) and Ekiti people in the South-Western region of Nigeria called it 'Uagbo', which they used locally to treat back pain.…”