Details

Autor(en) / Beteiligte

• Shwe, Htay Htay
• Aye, Mye
• Sein, Myint Myint
• Htay, Khin Than
• Kreitmeier, Peter
• Gertsch, Jürg
• Reiser, Oliver
• Heilmann, Jörg

Titel

Cytotoxic Steroidal Saponins from the Rhizomes of Tacca integrifolia

Ist Teil von

• Chemistry & biodiversity, 2010-03, Vol.7 (3), p.610-622

Ort / Verlag

Zürich: WILEY-VCH Verlag

Erscheinungsjahr

2010

Link zum Volltext

Quelle

Wiley-Blackwell Journals

Beschreibungen/Notizen

• Three new steroid saponins (3β,25R)‐spirost‐5‐en‐3‐yl 6‐deoxy‐α‐L‐mannopyranosyl‐(1→2)‐[β‐D‐glucopyranosyl‐(1→4)‐6‐deoxy‐α‐L‐mannopyranosyl‐(1→3)]‐β‐D‐glucopyranoside (1), (3β,22R,25R)‐26‐(β‐D‐glucopyranosyloxy)‐22‐hydroxyfurost‐5‐en‐3‐yl 6‐deoxy‐α‐L‐mannopyranosyl‐(1→2)‐[6‐deoxy‐α‐L‐mannopyranosyl‐(1→3)]‐β‐D‐glucopyranoside (3), and (3β,22R,25R)‐26‐(β‐D‐glucopyranosyloxy)‐22‐hydroxyfurost‐5‐en‐3‐yl 6‐deoxy‐α‐L‐mannopyranosyl‐(1→2)‐[β‐D‐glucopyranosyl‐(1→4)‐6‐deoxy‐α‐L‐mannopyranosyl‐(1→3)]‐β‐D‐glucopyranoside (5), as well as the new pregnane glycoside (3β,16β)‐3‐{[6‐deoxy‐α‐L‐mannopyranosyl‐(1→2)‐[6‐deoxy‐α‐L‐mannopyranosyl‐(1→3)]‐β‐D‐glucopyranosyl]oxy}‐20‐oxopregn‐5‐en‐16‐yl (4R)‐5‐(β‐D‐glucopyranosyloxy)‐4‐methylpentanoate (6), were isolated from the rhizomes of Tacca integrifolia together with two known (25R) configurated steroid saponins (3β,25R)‐spirost‐5‐en‐3‐yl 6‐deoxy‐α‐L‐mannopyranosyl‐(1→2)‐[6‐deoxy‐α‐L‐mannopyranosyl‐(1→3)]‐β‐D‐glucopyranoside (2) and (3β,22R,25R)‐26‐(β‐D‐glucopyranosyloxy)‐22‐methoxyfurost‐5‐en‐3‐yl 6‐deoxy‐α‐L‐mannopyranosyl‐(1→2)‐[6‐deoxy‐α‐L‐mannopyranosyl‐(1→3)]‐β‐D‐glucopyranoside (4). The cytotoxic activity of the isolated compounds was evaluated in HeLa cells and showed the highest cytotoxicity value for compound 2 with an IC50 of 1.2±0.4 μM. Intriguingly, while compounds 1–5 exhibited similar cytotoxic properties between 1.2±0.4 (2) and 4.0±0.6 μM (5), only compound 2 showed a significant microtubule‐stabilizing activity in vitro.