Three new pentacyclic triterpenoids from twigs of Manniophyton fulvum (Euphorbiaceae)

[Display omitted] •Three new pentacyclic triterpenoids were isolated from Manniophyton fulvum.•1H and 13C NMR values of 3α-hydroxy-1-oxofriedelan are reported for the first time.•All the known compounds were isolated for the first time from Manniophyton fulvum.•Manniotaraxerol A and betulinic acid s...

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Published in:Phytochemistry letters 2018-10, Vol.27, p.1-8
Main Authors: Mbeunkeu, Ahri Bernie Djamen, Azebaze, Anatole Guy Blaise, Tala, Michel Feussi, Teinkela, Jean Emmanuel Mbosso, Noundou, Xavier Siwe, Krause, Rui Werner Maçedo, Vardamides, Juliette Catherine, Laatsch, Hartmut
Format: Article
Language:English
Subjects:
Cytotoxic activity
Euphorbiaceae
Manniophyton fulvum
Pentacyclic triterpenoids
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Summary:[Display omitted] •Three new pentacyclic triterpenoids were isolated from Manniophyton fulvum.•1H and 13C NMR values of 3α-hydroxy-1-oxofriedelan are reported for the first time.•All the known compounds were isolated for the first time from Manniophyton fulvum.•Manniotaraxerol A and betulinic acid showed cytotoxicity against HeLa cells. Phytochemical investigation of the methanol extracts of the twigs of Manniophyton fulvum has led to the isolation and characterization of three new pentacyclic triterpenoids, designated as 3α,28-dihydroxyfriedelan-1-one (1), manniotaraxerol A (3) and manniotaraxerol B (4), along with fourteen known compounds, 3α-hydroxy-1-oxofriedelane (2), betulinic acid (5), friedelin (S1), taraxerol (S2), a mixture of stigmasterol (S3) and β-sitosterol (S4), herranone (S5), docosanoic acid (S6), ursolic acid (S7), nasutin B (S8), bergenin (S9), stigmasterol-3-O-β-d-glucopyranoside (S10), 1,2-di-O-palmitoyl-3-O-(6-sulfo-α-d-quinovopyranosyl)glycerol (S11), and aridanin (S12). The structures of all compounds were determined by comprehensive spectroscopic analyses (1D and 2D NMR, EI and ESI-MS). 3α,28-Dihydroxyfriedelan-1-one (1), 3α-hydroxy-1-oxofriedelane (2), manniotaraxerol A (3), manniotaraxerol B (4), and betulinic acid (5) were evaluated against HeLa (human cervix adenocarcinoma) cancer cells. Manniotaraxerol A (3) showed weak in vitro cytotoxicity with a cell viability value of 49.3%. Betulinic acid (5) also showed significant cytotoxicity against HeLa cell with a cell viability value of 4.0%; the other compounds were inactive in this test.
ISSN:1874-3900
1876-7486
DOI:10.1016/j.phytol.2018.06.019