Cytotoxic Alkaloids from Leaves and Twigs of <i>Dasymaschalon sootepense</i>

Hongthong, Sakchai; Kuhakarn, Chutima; Reutrakul, Vichai; Jariyawat, Surawat; Piyachaturawat, Pawinee; Nuntasaen, Narong; Jaipetch, Thaworn

doi:10.1177/1934578x1400900711

Cited by 6 publications

(9 citation statements)

References 37 publications

(58 reference statements)

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“…Compound 1 was obtained as yellowish amorphous solid (mp >300ºC) and displayed positive test with Dragendorff's reagent, suggesting that compound 1 was an alkaloid derivative [8]. It had a molecular formula C 20 H 15 NO 6 as established from HRMS-ESI data (found: 366.0982, [M+H] + , calcd 366.0978 for C 20 H 16 NO 6 ).…”

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confidence: 94%

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The first phytochemical investigation of the root of Dasymaschalon glaucum led to the isolation of a new oxoaporphine alkaloid 1 together with seven known compounds, duguevalline (2), stigmalactam (3), enterocarpam III (4), desmosdumotin B (5), spiraeamide (6), kaempferol-3-O-glucopyranoside (7) and -sitosterol (8). The chemical structures of all isolated compounds were established on the basis of their spectroscopic data.

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confidence: 99%

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A New Oxoaporphine Alkaloid from the Root of Dasymaschalon glaucum

Silprakob

Sukhamsri

Kuhakarn

et al. 2018

Natural Product Communications

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confidence: 99%

A New Oxoaporphine Alkaloid from the Root of Dasymaschalon glaucum

Silprakob

Sukhamsri

Kuhakarn

et al. 2018

Natural Product Communications

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“…, and Marsypopetalum modestum (Pierre) B.Xue & R.M.K.Saunders. These species were chosen because there has been no previous study on anti-cancer activity, but certain species in the genus Uvaria L. [ 18 , 19 ], Dasymaschalon Dalla Torre & Harms [ 20 , 21 ], and Artabotrys R.Br. [ 22 ] had been shown to exhibit considerable anti-cancer activities.…”

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Cell cycle arrest and apoptosis induction by methanolic leaves extracts of four Annonaceae plants

Pumiputavon

Chaowasku

Saenjum

et al. 2017

BMC Complement Altern Med

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Background Uvaria longipes (Craib) L.L.Zhou, Y.C.F.Su & R.M.K.Saunders, Artabotrys burmanicus A.DC, Marsypopetalum modestum (Pierre) B.Xue & R.M.K.Saunders and Dasymaschalon sp. have been used for traditional medicine to treat cancer-like symptoms in some ethnic groups of Thailand and Laos.MethodsWe evaluated the anti-cancer activity of these Annonaceae plants against several human cancer cell lines. The apoptosis induction was detected by Annexin/propidium iodide (PI) staining. Phytochemical screening was tested by standard protocols and bioactive compounds were determined by HPLC.ResultsThe crude extracts from leaves of U. longipes, Dasymaschalon sp., A. burmanicus, and M. modestum showed particular effects that were found to vary depending on the cancer cell line, suggesting that the effect was in a cell-type specific manner. Interestingly, the induction of apoptotic cell death was prominent by the leaves-derived crude extract of M. modestum. This crude was, therefore, subjected to cell cycle analysis by PI staining. Results showed that this crude extract arrested cell cycle and increased the percentage of cells in the SubG1 phase in some cancer cell lines. The phytochemical screening tests indicated that all crude extracts contained tannins and flavonoids. HPLC of flavonoids using standards identified rutin as an active compound in U. longipes and Dasymaschalon sp., whereas quercetin was found in U. longipes and M. modestum.ConclusionsThese crude extracts provide a new source for rutin and quercetin, which might be capable of inducing cancer cell apoptotic death in a cell-type specific manner. This suggests, by analyzing the major bioactive compounds, the potential use of these crudes for chemotherapy in the future.

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“…Many of them showed various biological properties e.g. anticancer [21,22], antiplatelet aggregation [37], antiplasmodium [38,39], and topoisomerase I inhibition [40]. To the best our database search, except for aristolactam BII (2) [41], the evaluation of anti-HIV activity of compounds 1 and 3-9 has not been described previouly.…”

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“…Twelve species of the Dasymaschalon genus were found in Thailand [16]. Phytochemical investigation of plants in this genus led to the isolation of several biologically active compounds including essential oils [17], acetogenins [18], cycloartanes [19], alkaloids [19][20][21][22][23], flavonoids [18,24], cyclohexene oxide derivatives [19,25], neolignans [26] and a novel anti-tumor caged xanthone [27].…”

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Anti-HIV Activity of Alkaloids fromDasymaschalon echinatum

Bunteang

Chanakul

Hongthong

et al. 2018

Natural Product Communications

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Bioassay-guided fractionation of the aerial parts of Dasymaschalon echinatum led to the isolation of five known aristolactams; aristolactam AII (1), aristolactam BII (2), piperolactam A (3), piperolactam C (4), and goniopedaline (5), together with two aphorphine alkaloids; duguevalline (6) and noraristolodione (7) and two amide derivatives; asperphenamate (8), and N-benzoyl-L-phenylalaninol (9). Alkaloids 2 and 7 were isolated for the first time from the Dasymaschalon genus. The anti-HIV 1 reverse transcriptase (RT) activity of all isolated compounds was determined. Except for aristolactam BII (2), this is the first report of the anti-HIV 1-RT activity of compounds 1 and 3-9. Compounds 1, 3, 5, 6 and 8 showed weak anti-HIV 1-RT inhibitory activity with IC 50 ranging from 112.74 to 225.55 M.

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Cytotoxic Alkaloids from Leaves and Twigs of Dasymaschalon sootepense

Cited by 6 publications

References 37 publications

A New Oxoaporphine Alkaloid from the Root of Dasymaschalon glaucum

A New Oxoaporphine Alkaloid from the Root of Dasymaschalon glaucum

Cell cycle arrest and apoptosis induction by methanolic leaves extracts of four Annonaceae plants

Anti-HIV Activity of Alkaloids fromDasymaschalon echinatum

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