N-trans-caffeoyloctopamine

Pmio, 2016, 3(03):e64-e67.

In Vitro Mammalian Arginase Inhibitory and Antioxidant Effects of Amide Derivatives Isolated from the Hempseed Cakes (Cannabis sativa).[Reference: WebLink]

METHODS AND RESULTS:
In an effort to identify novel inhibitors of arginase, a phytochemical study was performed on hempseed cakes (Cannabis sativa L.). It led to the isolation of a new lignanamide, cannabisin I ( 1), together with seven known lignanamides, cannabisins A, B, C, F, M, 3,3′-demethylgrossamide, grossamide, and two phenylpropanoid amides, N-trans-caffeoyltyramine and N-trans-caffeoyloctopamine, among which was later identified for the first time from C. sativa. Their structures were elucidated by comprehensive analysis of NMR spectroscopy and mass spectrometry data. These compounds were evaluated on mammal arginase (purified liver bovine arginase), showing that N-trans-caffeoyltyramine exhibited the higher activity with an IC50 value of 20.9 µM, which remains, however, less active than the reference compound S-(2-boronoethyl)-l-cysteine (IC50 = 4.3 µM). Radical scavenging capacity of these compounds was determined by the ORAC-FL method.
CONCLUSIONS:
All tested cannabisins displayed antioxidant activity close to or better than the reference compounds. N-trans-Caffeoyltyramine has both arginase inhibitory property and antioxidant capacity.

Biochemical Systematics & Ecology, 2015, 58:265-269.

Phenylpropanoid amides from the roots of Solanum melongena L. (Solanaceae).[Reference: WebLink]

METHODS AND RESULTS:
Phytochemical investigation of the roots of Solanum melongena L. led to the isolation of 16 phenylpropanoid amides (1–16). Their structures were identified by analysis of spectroscopic data and comparison with those reported in the literature.
CONCLUSIONS:
This is the first report of the natural occurrence of N-trans-sinapoyloctopamine (9) and N-trans-caffeoyloctopamine (10). N-trans-feruloylnoradrenline (12) and N-cis-feruloylnoradrenline (16) were isolated from the genus Solanum for the first time. Four compounds including 3-(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)-2-methoxyethyl] acrylamide (5), 3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)-2-methoxyethyl] acrylamide (6), N-trans-p-coumaroylnoradrenline (11), and N-cis-p-coumaroyloctopamine (15) were firstly reported from S. melongena. The chemotaxonomic significance of these compounds was summarized.