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Planta Med 2012; 78(18): 1949-1956
DOI: 10.1055/s-0032-1327878
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

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

Suzye Mireille Moladje Donkwe
1   Department of Chemistry, Faculty of Sciences, University of Douala, Douala, Cameroon
,
Emmanuel Ngeufa Happi
1   Department of Chemistry, Faculty of Sciences, University of Douala, Douala, Cameroon
,
Jean Duplex Wansi
1   Department of Chemistry, Faculty of Sciences, University of Douala, Douala, Cameroon
2   Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, Bielefeld, Germany
,
Bruno Ndjakou Lenta
3   Department of Chemistry, Higher Teachersʼ Training College, University of Yaounde, Yaounde, Cameroon
,
Krishna Prasad Devkota
4   Institute of Forestry, Pokhara Campus, Tribhuvan University, Pokhara, Kaski, Nepal
6   Current Address: Molecular Targets Laboratory, Molecular Discovery Program, Center for Cancer Research, NCI-Frederick, Frederick, MD, USA
,
Beate Neumann
5   Inorganic and Structural Chemistry, Department of Chemistry, Bielefeld University, Bielefeld, Germany
,
Hans-Georg Stammler
5   Inorganic and Structural Chemistry, Department of Chemistry, Bielefeld University, Bielefeld, Germany
,
Norbert Sewald
5   Inorganic and Structural Chemistry, Department of Chemistry, Bielefeld University, Bielefeld, Germany
› Author Affiliations
Further Information

Publication History

received 10 August 2011
revised 11 September 2012

accepted 26 September 2012

Publication Date:
07 November 2012 (online)

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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

Supporting Information

 

  • References

  • 1 Engler A. Simarubaceae. Nat Pflanzenfam III 1896; 4: 202-230
    PubMedGoogle Scholar
  • 2 Aubreville A. Flore du Gabon. Vol. 3. Paris: Museum National dʼHistoire Naturelles; 1962: 37
    Google Scholar
  • 3 Bouquet A. Féticheurs et médecines traditionnelles du Congo. (Brazzaville) Mémoires. Vol 36. Paris: O.R.S.T.O.M.; 1969: 229
    Google Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 5 Forgacs P, Provost J, Touche A. Alcaloïdes indoliques d Odyendea gabonensis . Planta Med 1982; 46: 187-189
    Article in Thieme ConnectPubMedGoogle Scholar
  • 6 Waterman PG, Ampofo SA. Cytotoxic quassinoids from Odyendyea gabonensis stem bark: Isolation and high-field NMR. Planta Med 1984; 50: 261-263
    Article in Thieme ConnectPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 12 Alam MS, Chopra N, Ali M, Niwa M. Oleanen and stigmasterol derivatives from Ambroma augusta . Phytochemistry 1996; 44: 1197-1200
    PubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    PubMedGoogle Scholar
  • 17 Hikino H, Ohta T, Takemoto T. Picrasins, simaroubolides of Japanese Quassia tree Picrasma quassioides . Phytochemistry 1975; 14: 2473-2481
    CrossrefPubMedGoogle Scholar
  • 18 Hamburger MO, Cordell GA. 1H and 13C-NMR spectroscopic studies of selected quassinoids. Planta Med 1988; 52: 352-355
    Article in Thieme ConnectPubMedGoogle Scholar
  • 19 Moron J, Merreien M-A, Polonsky J. Sur la biosynthèse des quassinoïdes de Simaruba glauca (Simaroubaceae). Phytochemistry 1971; 10: 585-592
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    Article in Thieme ConnectPubMedGoogle Scholar
  • 23 Khuroo MA, Qureshi MA, Razdan TK, Nichols P. Sterones, iridoids and a sesquiterpene from Verbascum thapsus . Phytochemistry 1988; 27: 3541-3544
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 25 Della Greca M, Monaco P, Previtera L. Stigmasterols from Typha latifolia . J Nat Prod 1990; 53: 1430-1435
    CrossrefPubMedGoogle Scholar