The in vitro anti-inflammatory effect of eight aporphine alkaloids isolated from the leaves of two Lauraceae plants (Pleurothyrium cinereum and Ocotea macrophylla) was evaluated through inhibition of two isozymes of cyclooxygenase (COX-1 and COX-2), 5-lipoxygenase (5-LOX), and platelet aggregation induced by PAF, AA and ADP. All alkaloids exhibited inhibitory activities against COX-2 (IC50 25.9-116 μM range) and PAF- and AA-induced platelet aggregation, while only four and three of them were good COX-1 and 5-LOX inhibitors, respectively. (+)-N-acetyl-nornantenine 6 was the most potent COX-2, 5-LOX, AA and PAF inhibitor.
KoichiN. (2004) Significance of vascular inflammation in acute coronary syndrome. Journal of Japanese College of Angiology, 44, 311–317.
2.
de GaetanoG, DonatiMB, CerlettiC. (2003) Prevention of thrombosis and vascular inflammation: benefits and limitations of selective or combined COX-1, COX-2 and 5-LOX inhibitors. Trends in Pharmacological Sciences, 24, 245–272.
3.
DannhardtG, LauferS. (2000) Structural approaches to explain the selectivity of COX-2 inhibitors: Is there a common pharmacophore?Current Medicinal Chemistry, 7, 1101–1112.
4.
WeilJ, Colin-JonesD, LangmanM, LawsonD, LoganR, MurphyM, RawlinsM, VesseyM, WainwrightP. (1995) Prophylactic aspirin and risk of peptic ulcer bleeding. British Medical Journal, 310, 827–830.
5.
BombardierC, LaineL, ReicinA, ShapiroD, Burgos-VargasR, DavisB, DayR, Bosi-FerrazM, HawkeyCJ, HochbergMC, KvienTK, SchnitzerTJ. (2000) Comparison of upper gastrointestinal toxicity of rofecoxib and naproxen in patients with rheumatoid arthritis. The New England Journal of Medicine, 343, 1520–1528.
6.
de Silva FilhoAA, AndradeE Silva ML, CarvalhoJCT, BastosJK. (2004) Evaluation of analgesic and anti-inflammatory activities of Nectandra megapotamica (Lauraceae) in mice and rats. Journal of Pharmacy and Pharmacology, 56, 1179–1184.
7.
LinCT, ChuFH, TsengYH, TsaiJB, ChangST, WangSY. (2007) Bioactivity investigation of Lauraceae trees grown in Taiwan. Pharmaceutical Biology, 45, 638–644.
8.
BallabeniV, TognoliniM, BertoniS, BruniR, GuerriniA, Moreno-RuedaG, BarocelliE. (2007) Antiplatelet and antithrombotic activities of essential oil from wild Ocotea quixos (Lam.) Kosterm. (Lauraceae) calices from Amazonian Ecuador. Pharmacological Research, 55, 23–30.
9.
ChenCC, LinCF, HuangYL. (1995) Bioactive constituents from the flower buds and peduncles of Lindera megaphylla. Journal of Natural Products, 58, 1423–1425.
10.
ChenKS, KoFN, TengCM, WuYC. (1996) Antiplatelet and vasorelaxing actions of some aporphinoids. Planta Medica, 62, 133–136.
11.
ChiaYC, ChenKS, ChangYL, TengCM, WuYC. (1999) Antiplatelet actions of aporphinoids from formosan plants. Bioorganic & Medicinal Chemistry Letters, 9, 3295–3300.
12.
YuSM, ChenCC, KoFN, HuangYL, HuangTF, TengCM. (1992) Dicentrine, a novel antiplatelet agent inhibiting thromboxane formation and increasing the cyclic AMP level of rabbit platelets. Biochemical Pharmacology, 43, 323–329.
13.
SaitoS, OhizumiY. (2004) (+)-nantenine inhibited 5-HT-induced aggregation and concomitant increase of intracellular Ca2+ in rabbit washed platelet but did not inhibit shape change in PRP. Pharmacometrics, 66, 295–298.
14.
OralloF. (2004) Acute cardiovascular effects of (+)-nantenine, an alkaloid isolated from Platycapnos spicata, in anaesthetised normotensive rats. Planta Medica, 70, 117–126.
15.
CoyED, CucaLE. (2008) Nuevo alcaloide oxoaporfínico y otros constituyentes químicos aislados de Pleurothyrium cinereum (Lauraceae). Revista Colombiana de Química, 37, 127–134.
16.
CoyED, CucaLE. (2009) Aporphine alkaloids from leaves of Ocotea macrophylla (Kunth) (Lauraceae) from Colombia. Biochemical Systematics and Ecology, 37, 522–524.
17.
ChowdhuryMA, AbdellatifKRA, DongY, DasD, SureshMR, KnausEE. (2008) Synthesis of celecoxib analogs that possess a N-hydroxypyrid-2(1H)one 5-lipoxygenase pharmacophore: Biological evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity. Bioorganic and Medicinal Chemistry Letters, 18, 6138–6141.
18.
RaoPNP, AminiM, LiH, HabeebAG, KnausEE. (2003) Design, synthesis, and biological evaluation of 6-substituted-3-(4-methanesulfonylphenyl)-4-phenylpyran-2-ones: a novel class of diarylheterocyclic selective cyclooxygenase-2 inhibitors. Journal of Medicinal Chemistry, 46, 4872–4882.
19.
WangBG, HongX, LiL, ZhouJ, HaoXJ. (2000) Chemical constituents of two Chinese Magnoliaceae plants, Tsoongiodendron odorum and Manglietiastrum sinicum, and their inhibition of platelet aggregation. Planta Medica, 66, 511–515.
20.
CoyE D, CucaLE, SefkowM. (2009) COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans. Bioorganic and Medicinal Chemistry Letters, 19, 6922–6925.