N-trans-caffeoyltyramine

International Journal of Molecular Medicine, 2015,3:1042-1048.

N‑trans‑ρ‑caffeoyl tyramine isolated from Tribulus terrestris exerts anti‑inflammatory effects in lipopolysaccharide‑stimulated RAW 264.7 cells.[Reference: WebLink]

Inflammation is induced by the expression of cyclooxygenase‑2 (COX‑2), which is an important mediator of chronic inflammatory diseases, such as rheumatoid arthritis, asthma and inflammatory bowel disease. Tribulus terrestris (T. terrestris) is known to have a beneficial effect on inflammatory diseases.
METHODS AND RESULTS:
In this study, we investigated the effects of N‑trans‑ρ‑caffeoyltyramine (N-trans-caffeoyltyramine，CT) isolated from T. terrestris on the production of nitric oxide (NO), and the expression of pro‑inflammatory cytokines and COX‑2 in lipopolysaccharide (LPS)‑stimulated RAW 264.7 cells. We also aimed to elucidate the molecular mechanisms involved. We found that the ethanolic extract of T. terrestris (EETT) and CT inhibited the production of NO, tumor necrosis factor‑α (TNF‑α), interleukin (IL)‑6 and IL‑10 in the LPS‑stimulated RAW 264.7 cells in a dose‑dependent manner. They were determined by reverse transcription-polymerase chain reaction (RT-PCR) and enzyme-linked immunosorbent assay (ELISA). In addition, CT markedly suppressed the expression of COX‑2 and the production of prostaglandin E2 (PGE2) in response to LPS stimulation. Furthermore, CT markedly decreased p‑c‑Jun N‑terminal kinase (p‑JNK) protein expression in LPS‑stimulated RAW 264.7 cells. COX-2 and p-JNK were measured by western blot analysis.
CONCLUSIONS:
Taken together, these findings indicate that CT isolated from T. terrestris is a novel and potent modulator of inflammatory responses. Thus, it may prove benefiical to further evaluate CT as a possible treatment for chronic inflammatory diseases.

Journal of the Chinese Chemical Society, 2013, 44(3):313-319.

The Constituents from the Stems of Annona cherimola.[Reference: WebLink]

METHODS AND RESULTS:
Thirty‐five compounds including twenty‐one alkaloids, lysicamine (1 ), liriodenine (2 ), atherospermidine (3 ), oxoxylopine (4 ), oxoanolobine (5 ), oxoglaucine (6 ), (‐)‐anonaine (7 ), (‐)‐asimilobine (8 ), (‐)‐xylopine (9 ), (‐)‐anolobine (10 ), (‐)‐norisocorydine (11 ), (+)‐laurotetanine (12 ), (+)‐isocorydine (13 ), (‐)‐N‐methylasimilobine (14 ), (+)‐N‐methyllaurotetanine (15 ), (‐)‐norushinsunine (16 ), (‐)‐ushinsunine (17 ), (‐)‐N‐formylanonaine (18 ), (+)‐stepharine (19 ), (+)‐orentaline (20 ), and (‐)‐kikemanine (21 ); four kauranes, ent‐kaur‐16‐en‐19‐oic acid (22 ), 16β‐hydroxy‐17‐acetoxy‐ent‐kauran‐19‐al (23 ), 17‐acetoxy‐16β‐ent‐kauran‐19‐oic acid (24 ), and 16β‐hydroxy‐17‐acetoxy‐ent‐kauran‐19‐oic acid (25 ); two amides, N‐trans‐femloyltyramine (26 ), and N-trans-caffeoyltyramine (27 ); one purine, adenosine (28 ); one lactam amide, squamolone (29 ); and six steroids, β‐sitosterol (30 ), stigmasterol (31 ), β‐sitostenone (32 ), stigmasta‐4,22‐dien‐3‐one (33 ), 6β‐hydroxy‐β‐sitosterone (34 ), and 6β‐hydroxystigmasterone (35 ) are isolated from the stems of Annona cherimola.
CONCLUSIONS:
These compounds were characterized and identified by physical and spectral evidence. Among them, (‐)‐norisocorydine (11) was elucidated as a new enantiomer with a levorotary configuration, which is isolated for the first time.