Oxidative Burst Inhibitory and Cytotoxic Activity of Constituents of the Fruits of Odyendyea gabonensis

Abstract

The methanol extract of dried fruits of Odyendyea gabonensis afforded one new quassinoid [(−)-odyendanol (1)], one new canthin-6-one alkaloid [9-hydroxy-5-methoxycanthin-6-one (4)], and two new steroids [22E, 24R-stigmasta-5,22-diene-3,7-dione (7) and 22E,24R-stigmast-22-ene-3,7-dione (8)] along with fourteen known compounds. The structures of all compounds were established by analyzing the spectroscopic data. The ¹³C-NMR values of (−)-odyendene (2) and (−)-odyendane (3), as well as the single-crystal X-ray structure of 5-methoxycanthin-6-one (6) are also reported.

The oxidative burst inhibitory activity of pure compounds 1–12 was determined by the chemoluminescence assay, and cytotoxic activities of compounds 2–6 against the human prostate cancer cell PC-3 line were evaluated. Compounds 1–6 exhibited a clear suppressive effect on the phagocytosis response upon activation with serum-opsonized zymosan in the range of IC₅₀ = 0.9–2.0 µM versus ibuprofen with IC₅₀ = 12.1 µM, while all canthin-6-one alkaloids (4–6) displayed moderate cytotoxic activity against the human prostate cancer cell PC-3 line, with IC₅₀ values ranging from 13.5–15.4 µM versus doxorubicine with IC₅₀ = 1.5 µM.

Key words

Odyendyea gabonensis - Simaroubaceae - quassinoids - canthin-6-one alkaloids - steroids - oxidative burst inhibition - cytotoxicity

• References

• 1 Engler A. Simarubaceae. Nat Pflanzenfam III 1896; 4: 202-230
• 2 Aubreville A. Flore du Gabon. Vol. 3. Paris: Museum National dʼHistoire Naturelles; 1962: 37
• 3 Bouquet A. Féticheurs et médecines traditionnelles du Congo. (Brazzaville) Mémoires. Vol 36. Paris: O.R.S.T.O.M.; 1969: 229
• 4 Forgacs P, Provost J, Touche A, Guenard D, Thal C, Guilhem J. Structures de lʼodyendane et lʼodyendene, deux nouveaux quassinoides d Odyendea gabonensis (Pierre) Engl. Simaroubacées. Tetrahedron Lett 1985; 26: 3457-3460
• 5 Forgacs P, Provost J, Touche A. Alcaloïdes indoliques d Odyendea gabonensis . Planta Med 1982; 46: 187-189
• 6 Waterman PG, Ampofo SA. Cytotoxic quassinoids from Odyendyea gabonensis stem bark: Isolation and high-field NMR. Planta Med 1984; 50: 261-263
• 7 Usami Y, Nakagawa-Goto K, Lang JY, Yoon K, Lai CY, Goto M, Sakurai N, Taniguchi M, Toshiyuki A, Morris-Natschke SL, Bastow KF, Cragg G, Newman DJ, Fujitake M, Takeya K, Hung MC, Lee EY, Lee KH. Antitumor Agents. 282. 2′-(R)-O-acetylglaucarubinone, a quassinoid from Odyendyea gabonensis as a potential anti-breast and anti-ovarian cancer agent. J Nat Prod 2010; 73: 1553-1558
• 8 Helfand SL, Werkmeister J, Roder JC. Chemiluminescence response of human natural killer cells. The relationship between target cell binding, chemiluminescence, and cytolysis. J Exp Med 1982; 156: 492-505
• 9 Zhao Q, Chen Q, Hao XJ, Han J, Zuo YG, Xu GL. Cytotoxicity of labdane-type diterpenoids from Hedychium forrestii . Chem Pharm Bull 2008; 56: 210-212
• 10 Mitsunaga K, Kioke K, Tanaka T, Ohkawa Y, Kobayashi Y, Sawaguchi T, Ohmoto T. Canthin-6-one alkaloids from Eurycoma longifolia . Phytochemistry 1994; 35: 799-802
• 11 Grosvenor SNJ, Mascoll K, McLean S, Reynolds WF, Tinto WF. Tirucallane, apotirucallane, and octanorapotirucallane triterpenenes of Simarouba amara . J Nat Prod 2006; 69: 1315-1318
• 12 Alam MS, Chopra N, Ali M, Niwa M. Oleanen and stigmasterol derivatives from Ambroma augusta . Phytochemistry 1996; 44: 1197-1200
• 13 Jones SR, Selinsky BS, Rao MN, Zhang X, Kinney WA, Tham FS. Efficient route to 7α-(Benzoyloxy)-3-dioxolanecholestan-24 (R)-ol, a key intermediate in the synthesis of squalamine. J Org Chem 1998; 63: 3786-3789
• 14 Kotani E, Takeya T, Egawa H, Tobinaga S. Stereoselective 7α-hydroxylation of 3β-acetoxy-Δ⁵-steroids by Fe(PA)₃/H₂O₂/MeCN. Chem Pharm Bull 1997; 45: 750-752
• 15 Wandji J, Wansi JD, Fuendjiep V, Dagne E, Mulholland DA, Tillequin F, Fomum TZ, Sondengam BL, Nkeh BC, Njamen D. Sesquiterpene lactone and friedelane derivative from Drypetes molunduana . Phytochemistry 2000; 54: 811-815
• 16 Vanhaelen-Fastre R, Luyengi L, Vanhaelen M, Declercq JP, Meerssche VM. Two quassinoids and two coumarinolignoids from Hannoa klaineana roots. Phytochemistry 1987; 26: 317-319
• 17 Hikino H, Ohta T, Takemoto T. Picrasins, simaroubolides of Japanese Quassia tree Picrasma quassioides . Phytochemistry 1975; 14: 2473-2481
• 18 Hamburger MO, Cordell GA. 1H and 13C-NMR spectroscopic studies of selected quassinoids. Planta Med 1988; 52: 352-355
• 19 Moron J, Merreien M-A, Polonsky J. Sur la biosynthèse des quassinoïdes de Simaruba glauca (Simaroubaceae). Phytochemistry 1971; 10: 585-592
• 20 Ohmoto T, Koike K. Studies on the constituents of Picrasma quassioides Bennet: I. On the alkaloidal constituents. Chem Pharm Bull 1982; 30: 1204-1209
• 21 Wansi JD, Wandji J, Kamdem WAF, Ndom JC, Happi NE, Chiozem DD, Choudhary MI, Tsabang N, Tillequin F, Fomum ZT. Triterpenoids from Drypetes chevalieri Beille (Euphorbiaceae). Nat Prod Res 2006; 20: 586-592
• 22 Wandji J, Tillequin F, Mulholland DA, Wansi JD, Fomum TZ, Fuendjiep V, Libot F, Tsabang N. Fatty acid esters of triterpenoids and steroid glycosides from Gambeta africana . Planta Med 2002; 68: 822-826
• 23 Khuroo MA, Qureshi MA, Razdan TK, Nichols P. Sterones, iridoids and a sesquiterpene from Verbascum thapsus . Phytochemistry 1988; 27: 3541-3544
• 24 Gupta S, Ali M, Alan MS, Niwa M, Sakai T. 24β-Ethylcholes-4-en-3β-ol from the roots of Lawsonia inermis . Phytochemistry 1992; 31: 2558-2560
• 25 Della Greca M, Monaco P, Previtera L. Stigmasterols from Typha latifolia . J Nat Prod 1990; 53: 1430-1435