1. Naphthoquinone derivatives and lignans from the Paraguayan crude drug “tayi pyta” (Tabebuia heptaphylla, Bignoniaceae).

Schmeda-Hirschmann G, Papastergiou F.

Laboratorio de Quimica de Productos Naturales, Instituto de Quimica de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile. schmeda@utalca.cl

Z Naturforsch [C]. 2003 Jul-Aug;58(7-8):495-501.

PMID: 12939034 [PubMed - in process]

2. In vitro activity of Brazilian medicinal plants, naturally occurring naphthoquinones and their analogues, against methicillin-resistant Staphylococcus aureus.

Machado TB, Pinto AV, Pinto MC, Leal IC, Silva MG, Amaral AC, Kuster RM, Netto-dosSantos KR.

Nuleo de Pesquisas de Productos Naturais, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil

Int J Antimicrob Agents. 2003 Mar;21(3):279-84.

PMID: 12636992 [PubMed - in process]

3. Suppression of Human Prostate Cancer Cell Growth by beta-Lapachone via Down-regulation of pRB Phosphorylation and Induction of Cdk Inhibitor p21(WAF1/CIP1).

Choi YH, Kang HS, Yoo MA.

Department of Biochemistry, College of Oriental Medicine, Dong-Eui University and Research Center for Oriental Medicine, Pusan 614-052, Korea. choiyh@dongeui.ac.kr

J Biochem Mol Biol. 2003 Mar 31;36(2):223-9.

PMID: 12689523 [PubMed - in process]

4. Cyclopentene dialdehydes from Tabebuia impetiginosa.

Koyama J, Morita I, Tagahara K, Hirai K.

Kobe Pharmaceutical University, Japan. j-koyama@kobepharma-u.ac.jp

Phytochemistry. 2000 Apr;53(8):869-72.

PMID: 10820794 [PubMed - indexed for MEDLINE]

5. [Intratumoral administration of biological preparations--recommendation for integrative medicine] [Article in Japanese]

Ebina T.

Division of Immunology, Research Institute, Miyagi Cancer Center.

Gan To Kagaku Ryoho. 2001 Oct;28(11):1515-8.

PMID: 11707968 [PubMed - indexed for MEDLINE]

6. Potential antipsoriatic agents: lapacho compounds as potent inhibitors of HaCaT cell growth.

Muller K, Sellmer A, Wiegrebe W.

Institut fur Pharmazeutische Chemie, Westfalische Wilhelms-Universitat Munster, Hittorfstrasse 58-62, D-48149 Munster, Germany. kmuller@uni-muenster.de

J Nat Prod. 1999 Aug;62(8):1134-6.

PMID: 10479319 [PubMed - indexed for MEDLINE]

7. Antifungal activity of Paraguayan plants used in traditional medicine.

Portillo A, Vila R, Freixa B, Adzet T, Canigueral S.

Unitat de Farmacologia i Farmacognosia, Facultat de Farmacia, Avenida Diagonal 643, E-08028, Barcelona, Spain.

J Ethnopharmacol. 2001 Jun;76(1):93-8.

PMID: 11378288 [PubMed - indexed for MEDLINE]

8. Snakebites and ethnobotany in the northwest region of Colombia. Part III: neutralization of the haemorrhagic effect of Bothrops atrox venom.

Otero R, Nunez V, Barona J, Fonnegra R, Jimenez SL, Osorio RG, Saldarriaga M, Diaz A.

Programa de Ofidismo, Facultad de Medicina, Universidad de Antioquia, A.A. 1226, Medellin, Colombia. rotero@catios.udea.edu.co

J Ethnopharmacol. 2000 Nov;73(1-2):233-41.

PMID: 11025161 [PubMed - indexed for MEDLINE]

9. Screening of plants used in Argentine folk medicine for antimicrobial activity.

Anesini C, Perez C.

Catedra de Farmacologia, Facultad de Odontologia, Universidad de Buenos Aires, Argentina.

J Ethnopharmacol. 1993 Jun;39(2):119-28.

PMID: 8412245 [PubMed - indexed for MEDLINE]

10. Antioxidant activity and characterization of volatile constituents of Taheebo (Tabebuia impetiginosa Martius ex DC).

Park BS, Lee KG, Shibamoto T, Lee SE, Takeoka GR.

Western Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, Albany, California 94710, USA.

J Agric Food Chem. 2003 Jan 1;51(1):295-300.

PMID: 12502424 [PubMed - indexed for MEDLINE]

11. Chemical reactivity studies with naphthoquinones from Tabebuia with anti-trypanosomal efficacy.

Pinto CN, Dantas AP, De Moura KC, Emery FS, Polequevitch PF, Pinto MC, de Castro SL, Pinto AV.

Nucleo de Pesquisas em Produtos Naturais, Centro de Ciencias da Saude, Universidade Federal, Rio de Janeiro, Brazil.

Arzneimittelforschung. 2000 Dec;50(12):1120-8.

PMID: 11190779 [PubMed - indexed for MEDLINE]

1. Naphthoquinone derivatives and lignans from the Paraguayan crude drug “tayi pyta” (Tabebuia heptaphylla, Bignoniaceae).

Schmeda-Hirschmann G, Papastergiou F.

Laboratorio de Quimica de Productos Naturales, Instituto de Quimica de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile. schmeda@utalca.cl

Z Naturforsch [C]. 2003 Jul-Aug;58(7-8):495-501.

The Paraguayan crude drug “tayi pyta” is used to treat cancer, wounds and inflammation. It consist of the bark and trunkwood of Tabebuia heptaphylla (Bignoniaceae). A phytochemical study of the crude drug gave, in addition to previously described naphthoquinones and the known lignans cycloolivil and secoisolariciresinol, three new lapachenol (lapachonone)-, two naphthofuran-, a chromone and a naphthalene derivative. The structures were elucidated by means of high field NMR spectroscopy. The biological activity of the main compound lapachol and the related alpha-lapachone as well as the lignans cycloolivil and secoisolariciresinol can explain, at least in part, the effect atributed to the crude drug in Paraguayan folk medicine.

PMID: 12939034 [PubMed - in process]

2. In vitro activity of Brazilian medicinal plants, naturally occurring naphthoquinones and their analogues, against methicillin-resistant Staphylococcus aureus.

Machado TB, Pinto AV, Pinto MC, Leal IC, Silva MG, Amaral AC, Kuster RM, Netto-dosSantos KR.

Nuleo de Pesquisas de Productos Naturais, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil

Int J Antimicrob Agents. 2003 Mar;21(3):279-84.

Fourteen extracts from Brazilian traditional medicinal plants used to treat infectious diseases were used to look for potential antimicrobial activity against multiresistant bacteria of medical importance. Staphylococcus aureus strains were susceptible to extracts of Punica granatum and Tabebuia avellanedae. The minimum inhibitory concentrations (MICs) of the total extracts and of additional fractions of these plants were determined by employing strains of methicillin-resistant (MRSA) and -sensitive (MSSA) S. aureus, including isolates of the PFGE clone A, which is prevalent in Brazil and two ATCC reference strains. A mixture of ellagitannins isolated from P. granatum and two naphthoquinones isolated from T. avellanedae demonstrated antibacterial activity against all S. aureus strains tested. Semi-synthetic furanonaphthoquinones (FNQs) showed lower MICs than those exhibited by natural occurring naphthoquinones. The results indicate that these natural products can be effective potential candidates for the development of new strategies to treat MRSA infections.

PMID: 12636992 [PubMed - in process]

3. Suppression of Human Prostate Cancer Cell Growth by beta-Lapachone via Down-regulation of pRB Phosphorylation and Induction of Cdk Inhibitor p21(WAF1/CIP1).

Choi YH, Kang HS, Yoo MA.

Department of Biochemistry, College of Oriental Medicine, Dong-Eui University and Research Center for Oriental Medicine, Pusan 614-052, Korea. choiyh@dongeui.ac.kr

J Biochem Mol Biol. 2003 Mar 31;36(2):223-9.

The product of a tree (Tabebuia avellanedae) from South America, beta-lapachone, is known to exhibit various pharmacological properties, the mechanisms of which are poorly understood. The aim of the present study was to further elucidate the possible mechanisms by which beta-lapachone exerts its anti-proliferative action in cultured human prostate cancer cells. We observed that the proliferation-inhibitory effect of beta-lapachone was due to the induction of apoptosis, which was confirmed by observing the morphological changes and cleavage of the poly(ADP-ribose) polymerase protein. A DNA flow cytometric analysis also revealed that beta-lapachone arrested the cell cycle progression at the G1 phase. The effects were associated with the down-regulation of the phosphorylation of the retinoblastoma protein (pRB) as well as the enhanced binding of pRB and the transcription factor E2F-1. Also, beta-lapachone suppressed the cyclindependent kinases (Cdks) and cyclin E-associated kinase activity without changing their expressions. Furthermore, this compound induced the levels of the Cdk inhibitor p21(WAF1/CIP1) expression in a p53-independent manner, and the p21 proteins that were induced by beta-lapachone were associated with Cdk2. beta-lapachone also activated the reporter construct of a p21 promoter. Overall, our results demonstrate a combined mechanism that involves the inhibition of pRB phosphorylation and induction of p21 as targets for beta-lapachone. This may explain some of its anticancer effects.

PMID: 12689523 [PubMed - in process]

4. Cyclopentene dialdehydes from Tabebuia impetiginosa.

Koyama J, Morita I, Tagahara K, Hirai K.

Kobe Pharmaceutical University, Japan. j-koyama@kobepharma-u.ac.jp

Phytochemistry. 2000 Apr;53(8):869-72.

The isolation of two cyclopentene dialdehydes, 2-formyl-5-(4’-methoxybenzoyloxy)-3-methyl-2-cyclopentene-1-acetal dehyde, and 2-formyl-5-(3’, 4’-dimethoxybenzoyloxy)-3-methyl-2-cyclopentene-1-acetaldehyde, from the bark of Tabebuia impetiginosa is reported. The structures were established by analysis of spectroscopic data. These compounds showed anti-inflammatory activity.

PMID: 10820794 [PubMed - indexed for MEDLINE]

5. [Intratumoral administration of biological preparations--recommendation for integrative medicine] [Article in Japanese]

Ebina T.

Division of Immunology, Research Institute, Miyagi Cancer Center.

Gan To Kagaku Ryoho. 2001 Oct;28(11):1515-8.

The antitumor effect of biological preparations was examined in a double grafted tumor system. PSK is a hot water extract of cultured mycelia from Coliolus versicolor. Its protein content is about 38% and the main glycoside portion of PSK is beta-D-glucan. Lentinan is purified from fruit bodies of Lentinus edodes and is a beta-1, 3-glucan. Cepharanthin is an extract from the root of Stephania cepharantha HAYATA, consisting of 4 kinds of biscoclaurine alkaloids. TAHEEBO tea is a hot water extract of Tabebuia avellanedae, the active ingredient of which is naphthoquinones. If protein-bound polysaccharides were to be used in Western medicine, these polysaccharides would be purified, but purified beta-glucan loses its beneficial effects. Similarly, when raw Cepharanthin is purified to isolate its active ingredient (an alkaloid cepharanthine), its anti-tumor effect is weakened. Clear IAP induction was observed in serum of mice treated with extracts of Coliolus versicolor and Stephania cepharantha. However, IAP induction was not observed in the serum of mice treated with purified beta-glucan or purified alkaloid. This suggests that macrophages may recognize extracts but not purified substances. In Western medicine, purified substances with known chemical structures are recognized as drugs, but overdoses of these drugs are toxic to the body, thus adverse reactions are always an issue. In Chinese medicine, mixtures containing several crude drugs are recognized as drugs, whose active ingredients are not identified. In integrative medicine, drugs are extracts that contain active ingredients with known structures and functions. We propose a Japanese version of integrative medicine which is neither Western nor Chinese.

PMID: 11707968 [PubMed - indexed for MEDLINE]

6. Potential antipsoriatic agents: lapacho compounds as potent inhibitors of HaCaT cell growth.

Muller K, Sellmer A, Wiegrebe W.

Institut fur Pharmazeutische Chemie, Westfalische Wilhelms-Universitat Munster, Hittorfstrasse 58-62, D-48149 Munster, Germany. kmuller@uni-muenster.de

J Nat Prod. 1999 Aug;62(8):1134-6.

A number of lapacho compounds, representing the most common constituents of the inner bark of Tabebuia impetiginosa, together with some synthetic analogues, were evaluated in vitro against the growth of the human keratinocyte cell line HaCaT. With an IC(50) value of 0.7 microM, beta-lapachone (4) displayed activity comparable to that of the antipsoriatic drug anthralin. 2-Acetyl-8-hydroxynaphtho[2,3-b]furan-4,9-dione (7), which was prepared in a four-step synthesis from 2,8-dihydroxy-1, 4-naphthoquinone, was the most potent inhibitor among the known lapacho-derived compounds and inhibited cell growth with an IC(50) value of 0.35 microM. Furthermore, other active constituents of lapacho inhibited keratinocyte growth, with IC(50) values in the range of 0.5-3.0 microM. However, as already observed with anthralin, treatment of HaCaT cells with these potent lapacho compounds also caused remarkable damage to the plasma membrane. This was documented by leakage of lactate dehydrogenase into the culture medium, which significantly exceeded that of the vehicle control. Because of their potent activity against the growth of human keratinocytes, some lapacho-derived compounds appear to be promising as effective antipsoriatic agents.

PMID: 10479319 [PubMed - indexed for MEDLINE]

7. Antifungal activity of Paraguayan plants used in traditional medicine.

Portillo A, Vila R, Freixa B, Adzet T, Canigueral S.

Unitat de Farmacologia i Farmacognosia, Facultat de Farmacia, Avenida Diagonal 643, E-08028, Barcelona, Spain.

J Ethnopharmacol. 2001 Jun;76(1):93-8.

The antifungal activity of aqueous, dichloromethane and methanol extracts from 14 Paraguayan plants used in traditional medicine for the treatment of skin diseases was assayed in vitro by the agar disk diffusion method against 11 fungal strains comprising several filamentous fungi and yeasts. Among them, the dichloromethane extracts of Acanthospermum australe, Calycophyllum multiflorum, Geophila repens and Tabebuia avellanedae, as well as the aqueous and methanol extracts of the latter, showed the highest activity.

PMID: 11378288 [PubMed - indexed for MEDLINE]

8. Snakebites and ethnobotany in the northwest region of Colombia. Part III: neutralization of the haemorrhagic effect of Bothrops atrox venom.

Otero R, Nunez V, Barona J, Fonnegra R, Jimenez SL, Osorio RG, Saldarriaga M, Diaz A.

Programa de Ofidismo, Facultad de Medicina, Universidad de Antioquia, A.A. 1226, Medellin, Colombia. rotero@catios.udea.edu.co

J Ethnopharmacol. 2000 Nov;73(1-2):233-41.

Thirty-one of 75 extracts of plants used by traditional healers for snakebites, had moderate or high neutralizing ability against the haemorrhagic effect of Bothrops atrox venom from Antioquia and Choco, north-western Colombia. After preincubation of several doses of every extract (7.8-4000 microg/mouse) with six minimum haemorrhagic doses (10 microg) of venom, 12 of them demonstrated 100% neutralizing capacity when the mixture was i.d. injected into mice (18-20 g). These were the stem barks of Brownea rosademonte (Caesalpiniaceae) and Tabebuia rosea (Bignoniaceae); the whole plants of Pleopeltis percussa (Polypodiaceae), Trichomanes elegans (Hymenophyllaceae) and Senna dariensis (Caesalpiniaceae); rhizomes of Heliconia curtispatha (Heliconiaceae); leaves and branches of Bixa orellana (Bixaceae), Philodendron tripartitum (Araceae), Struthanthus orbicularis (Loranthaceae) and Gonzalagunia panamensis (Rubiaceae); the ripe fruits of Citrus limon (Rutaceae); leaves, branches and stem of Ficus nymphaeifolia (Moraceae). Extracts of another 19 species showed moderate neutralization (21-72%) at doses up to 4 mg/mouse, e.g. the whole plants of Aristolochia grandiflora (Aristolochiaceae), Columnea kalbreyeriana (Gesneriaceae), Sida acuta (Malvaceae), Selaginella articulata (Selaginellaceae) and Pseudoelephantopus spicatus (Asteraceae); rhizomes of Renealmia alpinia (Zingiberaceae); the stem of Strychnos xinguensis (Loganiaceae); leaves, branches and stems of Hyptis capitata (Lamiaceae), Ipomoea cairica (Convolvulaceae), Neurolaena lobata (Asteraceae), Ocimum micranthum (Lamiaceae), Piper pulchrum (Piperaceae), Siparuna thecaphora (Monimiaceae), Castilla elastica (Moraceae) and Allamanda cathartica (Apocynaceae); the macerated ripe fruits of Capsicum frutescens (Solanaceae); the unripe fruits of Crescentia cujete (Bignoniaceae); leaves and branches of Piper arboreum (Piperaceae) and Passiflora quadrangularis (Passifloraceae). When the extracts were independently administered by oral, i.p. or i.v. route either before or after an i.d. venom injection (10 microg), neutralization of haemorrhage dropped below 25% for all the extracts. Additionally, B. rosademonte and P. percussa extracts were able to inhibit the proteolytic activity of B. atrox venom on casein.

PMID: 11025161 [PubMed - indexed for MEDLINE]

9. Screening of plants used in Argentine folk medicine for antimicrobial activity.

Anesini C, Perez C.

Catedra de Farmacologia, Facultad de Odontologia, Universidad de Buenos Aires, Argentina.

J Ethnopharmacol. 1993 Jun;39(2):119-28.

Screening of 132 extracts from Argentine folk-medicinal plants for antimicrobial activity has been conducted using a penicillin G resistant strain of Staphylococcus aureus, Escherichia coli and Aspergillus niger as test microorganisms. Cephazolin, ampicillin and miconazole were used as standard antibiotics and concentration-response curves were obtained using the agar-well diffusion method. Boiling water extracts of plant materials were tested and 12 species were active against Staphylococcus aureus, whereas 10 were effective against Escherichia coli and 4 against Aspergillus niger. Tabebuia impetiginosa bark, Achyrocline sp. aerials parts, Larrea divaricata leaves, Rosa borboniana flowers, Punica granatum fruit pericarp, Psidium guineense fruit pericarp, Lithrea ternifolia leaves and Allium sativum bulbs produced some of the more active extracts.

PMID: 8412245 [PubMed - indexed for MEDLINE]

10. Antioxidant activity and characterization of volatile constituents of Taheebo (Tabebuia impetiginosa Martius ex DC).

Park BS, Lee KG, Shibamoto T, Lee SE, Takeoka GR.

Western Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, Albany, California 94710, USA.

J Agric Food Chem. 2003 Jan 1;51(1):295-300.

Volatiles were isolated from the dried inner bark of Tabebuia impetiginosa using steam distillation under reduced pressure followed by continuous liquid-liquid extraction. The extract was analyzed by gas chromatography and gas chromatography-mass spectrometry. The major volatile constituents of T. impetiginosa were 4-methoxybenzaldehyde (52.84 microg/g), 4-methoxyphenol (38.91 microg/g), 5-allyl-1,2,3-trimethoxybenzene (elemicin; 34.15 microg/g), 1-methoxy-4-(1E)-1-propenylbenzene (trans-anethole; 33.75 microg/g), and 4-methoxybenzyl alcohol (30.29 microg/g). The antioxidant activity of the volatiles was evaluated using two different assays. The extract exhibited a potent inhibitory effect on the formation of conjugated diene hydroperoxides (from methyl linoleate) at a concentration of 1000 microg/mL. The extract also inhibited the oxidation of hexanal for 40 days at a level of 5 microg/mL. The antioxidative activity of T. impetiginosa volatiles was comparable with that of the well-known antioxidants, alpha-tocopherol, and butylated hydroxytoluene.

PMID: 12502424 [PubMed - indexed for MEDLINE]

11. Chemical reactivity studies with naphthoquinones from Tabebuia with anti-trypanosomal efficacy.

Pinto CN, Dantas AP, De Moura KC, Emery FS, Polequevitch PF, Pinto MC, de Castro SL, Pinto AV.

Nucleo de Pesquisas em Produtos Naturais, Centro de Ciencias da Saude, Universidade Federal, Rio de Janeiro, Brazil.

Arzneimittelforschung. 2000 Dec;50(12):1120-8.

The biological activities of the naphthoquinones lapachol and its cyclization product beta-lapachone, extracted from trees of the genus Tabebuia, have been intensively studied. Given continuity to the studies about heterocyclic derivatives obtained from the reaction of these naphtoquinones with amino-containing reagents, 22 derivatives of beta-lapachone, nor-beta-lapachone and lapachol were synthesised and their activities against trypomastigote forms of T. cruzi were evaluated. The compounds were grouped as oxazolic, imidazolic, phenoxazinic, indolic, pyranic and cyclopentenic derivatives. The variability of the new structures is based on the great electrophilicity of 1,2-quinoidal carbonyls towards reagents containing nitrogen or carbon as nucleophilic centres. In relation to the trypanocidal activity of the synthesised compounds, in view of their structural diversity, tendencies only could be verified. Among the cyclofunctionalised products the oxazolic and imidazolic derivatives showed +/- 1.5 to 34.8 times higher activity than crystal violet, the standard drug for the sterilization of stored blood. These results corroborate the tendency of trypanocidal activity in imidazolic skeletons, and indicate that this moiety could be used as a guide for architectural delineation of molecules with potential value for the chemotherapy of Chagas disease.

PMID: 11190779 [PubMed - indexed for MEDLINE]

12 Antinociceptive and antiede properties and acute toxicity of Tabebuia avellanedae Lor. ex Griseb. inner bark aqueous extract matogenic

Fábio Guilherme Gonçalves de Miranda 1. , Jeane Carvalho Vilar , Ivana Andréa Nunes Alves , Sócrates Cabral de Holanda Cavalcanti and Ângelo Roberto Antoniolli

Departamento de Fisiologia, CCBS, Universidade Federal de Sergipe, São Cristovão, Sergipe, 49100-000, Brazil

BMC Pharmacology 2001 1:6

The electronic version of this article is the complete one and can be found online at: http://www.biomedcentral.com/1471-2210/1/6

Received 25 July 2001

Accepted 13 September 2001

Published 13 September 2001

© 2001 Miranda et al; licensee BioMed Central Ltd. Verbatim copying and redistribution of this article are permitted in any medium for any non-commercial purpose, provided this notice is preserved along with the article’s original URL. For commercial use, contact info@biomedcentral.com

Tabebuia avellanedae is a tree from the Bignoniaceae family. Commonly know as “pau d’arco” in Brazil, its inner bark is used as analgesic, anti-inflammatory, antineoplasic and diuretic at the Brazilian northeast. A validation of the plant usage has not been previously performed.

Antinociceptive and antiedematogenic effects of Tabebuia avellanedae Lor. ex Griseb. inner bark were measured by nociceptive experimental models in mice. A rat paw edema test induced by carrageenan (1%) was also performed in rats to access the plant’s antiedematogenic effect. The inner bark aqueous extract, administered via oral in three different concentration, namely 100, 200 and 400 mg/Kg, reduced the nociception produced by acetic acid (0.6% in water, i.p.) by 49.9%, 63.7% and 43.8%, respectively. The aqueous extract (200 and 400 mg/Kg, p.o.) reduced formalin (1%) effects only at the second phase of the experiment by 49.3% and 53.7%, respectively. Naloxone (5 mg/Kg, i.p.) was not able to revert the extract effect, however caffeine (10 mg/Kg, i.p.) reverted its effect by 19.8% at the second phase of the formalin test. The aqueous extract (200 mg/Kg, p.o.) inhibited edema by 12.9% when we used the rat paw edema model. The acute toxicity was low in mice.

The T. avellanedae inner bark aqueous extract presented antinociceptive and antiedematogenic activities at the used models, with a possible antinociceptive effect associated to the adenosine system.

Tabebuia avellanedae is a tree from the Bignoniaceae family. Commonly know as “pau d’arco” in Brazil, its inner bark is used as analgesic.