Hydroxycinnamic acid amides from Iochroma cyaneum

Amide Alkaloids from Scopolia tangutica

“…The 1 H NMR spectrum exhibited two sets of ABX-type spin coupling interactions between H-3 (δ H 6.68, d, J = 1.8 Hz), H-5 (δ H 6.54, dd, J = 8.4, 1.8 Hz), and H-6 (δ H 6.61, d, J = 8.4 Hz), and H-24 (δ H 6.57, d, J = 1.8 Hz), H-27 (δ H 6.71, d, J = 7.8 Hz), and H-28 (δ H 6.42, dd, J = 7.8, 1.8 Hz), which indicated the presence of two 1,2,4-trisubstituted benzene substructures. The 1 H and 13 C NMR data were similar to those of N 1 ,N 10 -di-dihydrocaffeoylspermidine[18], which was also isolated as the current purification process of known metabolite 5, except for the appearance of an additional methoxy [δ H 3.04 (3H, s, H-7-OMe) and δ C 56.1] and methine [δ H 4.36 (1H, dd, J = 9.0, 2.4 Hz, H-7) and δ C 80.3] group.…”

“…Nevertheless, we provide here the optical rotation value of 1 (see Extraction and isolation of compounds spectrum contained several absorption bands suggesting the presence of hydroxyl (3274 cm −1 ) and carbonyl (1646 cm −1 ) groups. The 1 H and 13 C NMR chemical shifts were similar to those of N 1 ,N 10 -di-dihydrocaffeoylspermidine [18], except for the presence of two methoxy groups [δ H 3.74 (3H, s, 2-OMe) and δ H 3.74 (3H, s, 25-OMe)] and a minor difference in the chemical shifts of the aromatic carbons and protons (l " Table 2). The HMBC spectrum of 3 revealed cross-peaks from 2-OMe (δ H 3.74) to C-2 (δ C 147.8), and 25-OMe (δ H 3.74) to C-25 (δ C 147.8), which indicated that the two methoxy groups were located at C-2 and C-25, respectively.…”

“…Supporting information available at http://www.thieme-connect.de/products fied as N 1 ,N 10 -di-dihydrocaffeoylspermidine (5) [18], scopolamine (6) [19], anisodamine (7) [19], hyoscyamine (8) [20], anisodine (9) [21], caffeoylputrescine (10) [22][23][24], and…”

Evolutionary correlations in flavonoid production across flowers and leaves in the Iochrominae (Solanaceae)

“…1). Phenolamides have been previously found in I. cyaneum, as well as other Solanaceae (Sattar et al, 1990). These phenolamides were found in higher concentrations in petals than in leaves.…”

Crops and Tasty, Nutritious Food – How Can Metabolomics Help?

“…Although this class of compounds had previously been reported in other species (Lycium chinense [Funayama et al, 1995], Aphelandra tetragona [Hedberg et al, 1996] and Iochroma cyaneum [Sattar et al, 1990]) this was the first report in a major food species. Indeed following this, the components were subsequently detected in other Solanaceae such as tomato (Lycopersicon esculentum) and tobacco (Nicotiana sylvestris) (Parr et al, 2005).…”