Isolation of Bioactive and Other Oxoaporphine Alkaloids from Two Annonaceous Plants, Xylopia aethiopica and Miliusa cf. banacea

Harrigan, George G.; Gunatilaka, A. A. L.; Kingston, David G. I.; Chan, George; Johnson, Randall K.

doi:10.1021/np50103a009

Cited by 86 publications

(42 citation statements)

References 11 publications

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“…Bioactive annonaceous acetogenins, xylopine and xylomatenin, have been isolated from the bark of Xylopia aromatica; these acetogenins showed cytotoxicities, comparable to adriamycin, against human solid tumor cell lines (Colman-Saizarbitoria et al, 1994). Oxoaporphine alkaloids, oxophoebine and liriodenine, have been isolated from Xylopia aethiopica; both showed selective toxicity against DNA repair and recombination deficient mutants of the yeast Saccharomyces cerevisae (Harrigan et al, 1994). We showed herein that Xylopia aromatica bark extract was active against Plasmodium falciparum in vitro but inactive in the in vivo model; this plant was 1.6 times less active than R. periviana in the FBIT.…”

Section: Discussionmentioning

confidence: 99%

Antimalarial activity of some Colombian medicinal plants

Garavito

Rincón

Arteaga

et al. 2006

Journal of Ethnopharmacology

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Section: Discussionmentioning

confidence: 99%

Antimalarial activity of some Colombian medicinal plants

Garavito

Rincón

Arteaga

et al. 2006

Journal of Ethnopharmacology

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“…Compounds 1-10 were identified by comparison of their spectroscopic data with those reported in the literature as caryophyllene oxide 19 (1), lichexanthone 20 (2), spathulenol 19 (3), a mixture of b-sitosterol 21 (4), and stigmasterol 21 (5), O-methylmoschatoline 22,23 (6), lysicamine 22,23 (7), nornuciferine 22 (8), liriodenine 6,23 (9), and isocoreximine 15 (10). Compounds 7-10 were recently found on the stem of this species, 15 while compounds 1-6, 11 and 12 were reported for the first time in this specie.…”

Section: Resultsmentioning

confidence: 99%

Chemical constituents isolated from the bark of Guatteria blepharophylla (Annonaceae) and their antiproliferative and antimicrobial activities

Costa¹,

Marques²,

Pinheiro³

et al. 2011

J. Braz. Chem. Soc.

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O estudo fitoquímico das cascas de Guatteria blepharophylla (Mart.) Mart. forneceu 12 compostos, sendo dois sesquiterpenos, óxido de cariofileno (1) e espatulenol (3), uma xantona, liquexantona (2), uma mistura de esteróides, b-sitosterol (4) e estigmasterol (5), e sete alcalóides isoquinolínicos, O-metilmoschatolina (6), lysicamina (7), nornuciferina (8), liriodenina (9), isocoreximina (10), subsessilina (11) e isomoschatolina (12). Suas estruturas foram determinadas através de métodos espectroscópicos. Os compostos 1-6, 11 e 12 são reportados pela primeira vez nesta espécie. Os dados de RMN 13 C (ressonância magnética nuclear) para os compostos 11 e 12 são descritos pela primeira vez na literatura. As atividades antiproliferativa em linhagens de células tumorais humanas e antimicrobiana foram investigadas para os compostos majoritários. O composto 9 mostrou significativa atividade contra linhagens de células de mama (MCF-7, Michigan Cancer Foundation-7), superior ao controle positivo doxorrubicina. O composto 12 apresentou atividade antifúngica similar ao controle positivo nistatina contra Candida albicans.Phytochemical study of the bark of Guatteria blepharophylla (Mart.) Mart. afforded twelve compounds, namely two sesquiterpenes, caryophyllene oxide (1) and spathulenol (3), one xanthone, lichexanthone (2), a mixture of steroids, b-sitosterol (4), and stigmasterol (5), and seven isoquinoline alkaloids, O-methylmoschatoline (6), lysicamine (7), nornuciferine (8), liriodenine (9), isocoreximine (10), subsessiline (11), and isomoschatoline (12). Their structures were established on the basis of spectroscopic methods. Compounds 1-6, 11 and 12 were reported for the first time in this species. The 13 C NMR (nuclear magnetic resonance) data for the compounds 11 and 12 are described for the first time in the literature. The antiproliferative activity against human tumour cell lines and antimicrobial activities were investigated for the major compounds. Compound 9 showed significant activity against cell lines of breast (MCF-7, Michigan Cancer Foundation-7), superior to the positive control doxorubicin. Compound 12 presented antifungal activity similar to the positive control nystatin against Candida albicans. Braz. Chem. Soc. 1112 and pharmacological investigations on some species of this family, including Guatteria, have indicated the presence of important bioactive compounds, exhibiting many pharmacological activities, such as, cytotoxicity against human tumor cell lines, 3-5 antimicrobial, 5,6-9 and antiparasitic properties, particularly against Leishmania sp., 3,7,[10][11][12] Plasmodium falciparum 5,12,13 and Trypanosoma sp. 3,12,14 Despite the importance of annonaceous members in folk medicine, the number of species that have been chemically investigated is still very small. One of them is Guatteria blepharophylla Mart in Mart, a small tropical tree that occurs in the Amazonian region (Brazil, Peru, Guyana, Ecuador and Venezuela). 1 In Brazil this species is common in Amazonas and Pará states, where it is...

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“…(sub M. banacea) two oxoapophine alkaloids, one new to science, were isolated and together with a total extract from the roots tested for bioactivity. The extracts showed selective toxicity against DNA repair and recombination deficient mutants of the yeast Saccharomyces cerevisiae (Harrigan et al, 1994). Four alkaloids have been extracted from the bark of M. velutina.…”

Section: Medicinal Uses and Phytochemistrymentioning

confidence: 99%

The genus Miliusa (Annonaceae) in the Austro-Malesian area

Mols

Kessler²

2003

Blum - J Plant Tax and Plant Geog

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sUMMArYA taxonomic revision of the Austro-Malesian species of Miliusa Lesch. ex A.DC. (Annonaceae) is presented. Ten species can be recognised in the area, including one new species, Miliusa novoguineensis, described here. Most species are restricted to certain islands or geographic areas. Miliusa horsfieldii (Benn.) Pierre is the main exception as it is distributed from Hainan up to Queensland, Australia. six of the ten species (except M. amplexicaulis ridl., M. longipes King, M. macropoda Miq. and M. parviflora ridl.) have a deciduous habit, and are largely restricted to areas with a monsoon climate. A key, based primarily on generative characters, and descriptions to the species are included.

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Isolation of Bioactive and Other Oxoaporphine Alkaloids from Two Annonaceous Plants, Xylopia aethiopica and Miliusa cf. banacea

Cited by 86 publications

References 11 publications

Antimalarial activity of some Colombian medicinal plants

Antimalarial activity of some Colombian medicinal plants

Chemical constituents isolated from the bark of Guatteria blepharophylla (Annonaceae) and their antiproliferative and antimicrobial activities

The genus Miliusa (Annonaceae) in the Austro-Malesian area

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