3-Methoxysampangine, a novel antifungal copyrine alkaloid from Cleistopholis patens

Liu, Shihchih; Oguntimein, Babajide O.; Hufford, Charles D.; Clark, Alice M.

doi:10.1128/aac.34.4.529

Cited by 79 publications

(58 citation statements)

References 10 publications

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“…From our study, infections caused by these Candida species in those HIV patients with the exception of Candida albicans strain 3 and Candida krusei, would be better treated with higher doses of Nystatin® than the extract because of the high MIC values of Nystatin® against the organisms. In a similar study by Hufford et al 21 three anti-candidal constituents were isolated from the root bark of Cleistopholis pat-ens. However the MIC of Eupolauridine (one of the constituents isolated) was found to be 1.56µg/ml which was greater than 0.39µg/ml the MIC value for amphotericin B against the three strains of Candida albicans used.…”

Section: Discussionmentioning

confidence: 99%

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Evaluation of the anti-candidal activity of methanolic leaf extract of cleistopholis patens (fam. Annonaceae) on candida species isolated from stage II HIV patients

Okechukwu¹,

Momoh²,

Esimone³

2015

Afr H. Sci.

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Background: Candida species (sp) is implicated in causing opportunistic disseminated mycotic complications in stage II HIV patients. Cleistopholis patens is a West African medicinal tree reported to have significant antifungal activity against C. albicans. Objectives: This study aimed to determine the anti-candidal activity of methanolic leaf extract of Cleistopholis patens against Candida species isolated from stage II HIV patients. Methods: The minimum inhibitory concentration (MIC) of the extract and Nystatin®® was determined by agar dilution method. The killing rate studies of the plant extract and Nystatin® were also determined. Results: The extract had activity against all Candida isolates, with the MIC against the five isolates ranging from 6.0 -9.8 mg/ml. Nystatin® also demonstrated plausible activity against the isolates with MICs ranging from 0.3125 -25 mg/ml. Candida albicans strain 2 was the most sensitive to both extract and Nystatin® with MIC values of 6 and 0.3125 mg/ml respectively. Candida krusei was the least sensitive with MIC values of 9.8 and 25 mg/ml for the extract and Nystatin® respectively. The killing rate values for the extract ranged from -0.029 to -0.091 min -1 and that of Nystatin® ranged from -0.076 to -0.112 16 min

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Section: Discussionmentioning

confidence: 99%

“…This was deviation from the findings of Hufford et al 1 . In another study, Liu et al 21 isolated a new alkaloid, 3 -methoxysampangine in association with three already known alkaloids from the root bark of Cleistopholis patens which had activity against Candida albicans, Aspergillus fumigatus and Cryptococcus neoformans.…”

Section: Discussionmentioning

confidence: 99%

Evaluation of the anti-candidal activity of methanolic leaf extract of cleistopholis patens (fam. Annonaceae) on candida species isolated from stage II HIV patients

Okechukwu¹,

Momoh²,

Esimone³

2015

Afr H. Sci.

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“…A clearer answer could likely be obtained from transcription profiling studies using comparable heme-deficient mutants from both organisms. Given its essential role in numerous cellular processes, heme biosynthesis or heme signaling could serve as a highly effective target for inhibiting fungal growth and could contribute to a chemical defense strategy against fungal pathogens in aporphinoid-producing plant species of the Annonaceae family (10,27,28,39,44,51,57,60). However, due to the importance of heme in all eukaryotes, a therapeutic drug that targets heme metabolism could most likely lack specificity for the fungal pathogen.…”

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confidence: 99%

Role of Heme in the Antifungal Activity of the Azaoxoaporphine Alkaloid Sampangine

Agarwal¹,

Xu²,

Jacob³

et al. 2008

Eukaryot Cell

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Sampangine, a plant-derived alkaloid found in the Annonaceae family, exhibits strong inhibitory activity against the opportunistic fungal pathogens Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus. In the present study, transcriptional profiling experiments coupled with analyses of mutants were performed in an effort to elucidate its mechanism of action. Using Saccharomyces cerevisiae as a model organism, we show that sampangine produces a transcriptional response indicative of hypoxia, altering the expression of genes known to respond to low-oxygen conditions. Several additional lines of evidence obtained suggest that these responses could involve effects on heme. First, the hem1⌬ mutant lacking the first enzyme in the heme biosynthetic pathway showed increased sensitivity to sampangine, and exogenously supplied hemin partially rescued the inhibitory activity of sampangine in wild-type cells. In addition, heterozygous mutants with deletions in genes involved in five out of eight steps in the heme biosynthetic pathway showed increased susceptibility to sampangine. Furthermore, spectral analyses of pyridine extracts indicated significant accumulation of free porphyrins in sampangine-treated cells. Transcriptional profiling experiments were also performed with C. albicans to investigate the response of a pathogenic fungal species to sampangine. Taking into account the known differences in the physiological responses of C. albicans and S. cerevisiae to low oxygen, significant correlations were observed between the two transcription profiles, suggestive of heme-related defects. Our results indicate that the antifungal activity of the plant alkaloid sampangine is due, at least in part, to perturbations in the biosynthesis or metabolism of heme.

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“…Minimum inhibitory concentration (MIC) of crude extract and pure isolates was determined using broth micro-dilution technique 41,42,43 . Stock solution of extract was two fold diluted with RPMI 1000-1 µg/ml (final volume=100 µl) and a final DMSO concentration ≤ 1%.…”

Section: Minimum Inhibitory Concentration (Mic)mentioning

confidence: 99%

Triterpene saponins of Maesa lanceolata leaves

Manguro¹,

Midiwo²,

Tietze³

et al. 2011

Arkivoc

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3-Methoxysampangine, a novel antifungal copyrine alkaloid from Cleistopholis patens

Cited by 79 publications

References 10 publications

Evaluation of the anti-candidal activity of methanolic leaf extract of cleistopholis patens (fam. Annonaceae) on candida species isolated from stage II HIV patients

Evaluation of the anti-candidal activity of methanolic leaf extract of cleistopholis patens (fam. Annonaceae) on candida species isolated from stage II HIV patients

Role of Heme in the Antifungal Activity of the Azaoxoaporphine Alkaloid Sampangine

Triterpene saponins of Maesa lanceolata leaves

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