Bioactive Compounds from Celaenodendron mexicanum

Abstract

Bioactivity-directed fractionation of the CHCl₃-MeOH extract of the leaves of Celaenodendron mexicanum by means of the brine shrimp lethality test and chromatographic techniques led to the isolation of three carboxylic acid triterpenes, the new tirucalla-type triterpene, 3α-hydroxytirucalla-7,24Z-dien-26-oic acid, 3-oxotirucalla-7,24Z-dien-26-oic acid, and epi-oleanolic acid, and three biflavonoids amentoflavone, podocarpusflavone A, and podocarpusflavone B. Four non-active compounds friedelin, maytensifolin B, 3β-hydroxyfriedelan-16-one, and celaenodendrolide were also obtained. epi-Oleanolic acid was the most active against brine shrimps with LC₅₀ value of 23.3 μM. In addition, all isolates were tested for in vitro antiprotozoal and cytotoxic activities. 3-Oxotirucalla-7,24Z-dien-26-oic acid and epi-oleanolic acid showed the highest activity against Leishmania donovani promastigotes with IC₅₀ values of 13.7 and 18.8 μM, respectively. Only 3-oxotirucalla-7,24Z-dien-26-oic acid showed activity against Trypanosoma brucei brucei bloodstream forms with IC₅₀ value of 16.8 μM.

Celaenodendron mexicanum - Euphorbiaceae - 3α-hydroxytirucalla-7,24Z-dien-26-oic acid - 3-oxotirucalla-7,24Z-dien-26-oic acid - epi-oleanolic acid - podocarpusflavone A - podocarpusflavone B - amentoflavone - antiprotozoal and cytotoxic effects

References

• 1 Croft  S L.. The current status of antiparasite chemotherapy.  Parasitology. 1997;;  114 S3-15
• 2 Castaneda  P,, Garcia  M R,, Hernandez  B E,, Torres  B A,, Anaya  A L,, Mata  R.. Effects of some compounds isolated from Celaenodendron mexicanum Standl (Euphorbiaceae) on seeds and phytogenic fungi.  Journal of Chemical Ecology. 1992;;  18 1025-37
• 3 Castaneda  P,, Bahena  A,, Garcia  E,, Chavez  D,, Mata  R,, Gutierrez  A.. Secondary metabolites from the stem bark of Celaenodendron mexicanum. .  Journal of Natural Products. 1993;;  56 1575-9
• 4 Camacho Corona  M DR.. Natural Products Against Protozoal Diseases. PhD Thesis,. University of London, London,; 1998: 1-412
• 5 Yardley  V,, Snowdon  D,, Croft  S L,, Hazra  B.. In vitro activity of diospyrin and derivatives against L. donovani, T. cruzi and Trypanosoma brucei brucei. .  Phytotherapy Research. 1996;;  10 559-62
• 6 Hirumi  H,, Hirumi  K.. Axenic culture of African trypanosoma blood stream forms.  Parasitology Today. 1994;;  10 10-84
• 7 Ekong  R,, Kirby  G C,, Patel  G,, Phillipson  J D,, Warhurst  D C.. Comparison of the in vitro activities of quassinoids with activity against Plasmodium falciparum, anisomicin and other inhibitors of protein synthesis.  Biochemical Pharmacology. 1990;;  40 297-301
• 8 Anderson  M M,, O'Neill  M J,, Phillipson  J D,, Warhurst  D C.. In vitro cytotoxicity of a series of quassinoids from Brucea javanica fruits against KB cells.  Planta Medica. 1991;;  57 62-4
• 9 Likhitwitayawuid  K,, Angerhofer  C K,, Cordell  G A,, Pezzuto  J M,, Ruangrungsi  N.. Cytotoxic and antimalarial BBIQ alkaloids from Stephania erecta. .  Journal Natural Products. 1993;;  30 30-8
• 10 Solis  P,, Wright  C W,, Anderson  M M,, Gupta  M P,, Phillipson  J D.. A microwell cytotoxicity assay using Artemia salina (brine shrimp).  Planta Medica. 1993;;  59 250-2
• 11 Da Silva  M FGF,, Francisco  R HP,, Gray  A I,, Lechat  J R,, Waterman  P G.. Lanosta-7-en-triterpenes from stem bark of Santiria trimera. .  Phytochemistry. 1990;;  29 1629-32
• 12 Ikuta  A,, Itokawa  H.. A triterpene from Akebia quinata callus tissue.  Phytochemistry. 1988;;  27 3809-10
• 13 Gunatilaka  L,, Nanayakkara  D,, Wazeer  M.. ¹³C NMR spectra of D : A friedo-oleanes.  Phytochemistry. 1983;;  22 991-2
• 14 Nosaki  H,, Susuki  H,, Hirayama  T,, Kasai  R,, Wu  R RY,, Lee  K H.. Antitumour triterpenes of Maytenus diversifolia. .  Phytochemistry. 1986;;  25 479-85
• 15 Markham  R,, Sheppard  C,, Geiger  H.. ¹³C NMR studies of some naturally occurring amentoflavone and hinokiflavone biflavonoids.  Phytochemistry. 1987;;  26 3335-7
• 16 Geiger  H,, Quinn  C.. In: The flavonoids. Harborne JB, Mabry TJ, Mabry H, editors Chapman & Hall, London,; 1975
• 17 Garg  H S,, Mitra  C R.. Putraflavone, a new biflavonoid from Putranjiva roxburghii. .  Phytochemistry. 1971;;  10 2787-91
• 18 Monaco  P,, Caputo  R,, Palumbo  G,, Mangoni  L.. Triterpene components of galls on the leaves of Pistacea terebinthus, produced by Pemphigus semilunaris. .  Phytochemistry. 1974;;  13 1992-3
• 19 Ghosal  S,, Lal  J,, Singh  S K.. The core structure of Shilajit humus.  Soil Biology & Biochemistry. 1991;;  23 673-80