Macrocarpins A-D, new cytotoxic nor-triterpenes from Maytenus macrocarpa

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 8, 2000, Pages 759-762

  Chávez, Haydee ^a   Rodríguez, Gladis ^a   Estévez Braun, Ana ^a   Ravelo, Ángel G ^a   Estévez Reyes, Rafael ^a   González, Antonio G ^a   Fdez Puente, Jose L ^b   García Grávalos, Dolores ^c  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b Instituto Biomar SA   (Spain)

^c PHARMAMAR S A   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; MACROCARPIN 1A; MACROCARPIN A; MACROCARPIN B; MACROCARPIN C; MACROCARPIN D; TRITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; NONHUMAN; PLANT ROOT; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TUMOR CELL LINE;

MOLECULAR STRUCTURE; PLANTS, MEDICINAL; SPECTRUM ANALYSIS; TRITERPENES;

MACROCARPA; MAYTENUS; MAYTENUS MACROCARPA;

EID: 0242689810     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00082-2     Document Type: Article

References (14)

1. González, A. G.; Bazzocchi, I. L.; Moujir, L.; Jiménez, I. A. Etnobotanical Uses of Celastraceae; Studies in Natural Products Chemistry; Elsevier Science Publisher, in press.
2. González G.J., Monache D.G., Monache D.F., Marini-Bettolo B.G. J. Ethnopharmacology. 5:1982;73.
3. Chávez H., Valdivia E., Estévez-Braun A., Ravelo A.G. Tetrahedron. 54:1998;13579.
4. Chávez H., Estévez-Braun A., Ravelo A.G. J. Nat. Prod. 62:1999;434.
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6. Gupta, M. P. 270 Plantas Medicinales Iberoamericanas, Convenio Andrés Bello. Colombia, 1995.
7. 13C NMR (CDCl3, 400 MHz): δ 51.50 (q, CO OME ), 179.03 (s, C OOMe), for the rest of the signals, see Table 1.
8. González A.G., Alvarenga N.L., Rodríguez F., Ravelo A.G., Jiménez I.A., Bazzocchi I.L., Gupta M.P. Nat. Prod. Lett. 7:1995;209.
9. 3, 400 MHz): δ 15.39 (q, Me-26), 16.97 (q, Me-27), 20.39 (q, CO OMe ), 20.63 (q, CO OMe ), 25.61 (q, Me-25), 28.49 (t, C-15), 29.54 (t, C-12), 29.81 (t, C-21), 30.24 (s, C-17), 30.53 (t, C-19), 31.77 (q, Me-28), 32.17 (q, Me-30), 32.72 (t, C-11), 35.65 (t, C-16), 35.87 (t, C-22), 36.22 (t, C-7), 37.69 (s, C-9), 38.87 (s, C-14), 39.57 (s, C-13), 40.55 (s, C-20), 43.15 (d, C-8), 44.58 (d, C-18), 51.66 (q, CO OMe ), 120.90 (d, C-1), 124.27 (s, C-4), 129.04 (s, C-5), 134.27 (s, C-3), 147.16 (s, C-2), 156.40 (s, C-10), 167.66 (s, -O C OMe), 168.18 (s, -O C OMe), 179.14 (s, C OOMe), 189.93 (d, C-23), 198.96 (s, C-6).
10. 3, 400 MHz): δ 7.33 (1H, s, H-1), 6.52 (1H, s, H-7), 4.52 (1H, d, J=3.2 Hz, H-22), 3.67 (1H, bs, OH-22), 2.66 (1H, m, H-20), 1.67 (3H, s, Me-25), 1.44 (3H, s, Me-26), 1.07 (3H, d, J=6.3 Hz), 0.99 (3H, s, Me-27), 0.89 (3H, s, Me-28).
11. 3, 400 MHz): δ 7.09 (1H, s, H-1), 6.35 (1H, s, H-6), 4.54 (1H, bs, H-22), 3.94 (3H, s, OMe), 2.65 (1H, m, H-20), 1.58 (3H, s, Me-25), 1.39 (3H, s, Me-26), 1.06 (3H, d, J=6.1 Hz, Me-30), 1.02 (3H, s, Me-27), 0.87 (H, s, Me-28).
12. 3, 400 MHz): 6.77 (1H, bs, OH-C3), 6.68 (1H, s, H-7), 6.24 (1H, s, H-1), 4.77 (1H, d, J=9.6 Hz, H-7), 4.58 (1H, bs, H-22), 3.67 (1H, bs, OH-22), 2.72 (1H, m, H-20), 2.07 (s, Me-23), 1.98 (1H, d, J=9.8 Hz), 1.31 (6H, s, Me-26+Me-27), 1.19 (3H, s, Me-25), 1.08 (3H, d, J=9.6 Hz), 0.88 (3H, s, Me-28).
13. The Molecular Mechanics PC Model program (version 6.0) was used in the Molecular Mechanics Calculations.
14. Bergeron R.J., Cavanaugh P.F., Kline S.J., Hughes R.G., Elliot G.T., Porter C.W. Biochem. Biophys. Res. Comm. 121:1984;848.