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A Hydroxylated Lupeol‐Based Triterpenoid Ester Isolated from the Scurrula parasitica Parasitic on Nerium indicum
Author(s) -
Liu QuanYu,
Wang Fei,
Zhang Lei,
Xie JieMing,
Li Peng,
Zhang YongHong
Publication year - 2015
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400254
Subject(s) - lupeol , stigmasterol , chemistry , ursolic acid , stereochemistry , quercetin , two dimensional nuclear magnetic resonance spectroscopy , daucosterol , triterpenoid , traditional medicine , biochemistry , chemical constituents , chromatography , medicine , antioxidant
(3 β ,7 β )‐7‐Hydroxylup‐20(29)‐en‐3‐yl hexadecanoate ( 1 ), a new lupeol‐based triterpenoid ester, along with sixteen known compounds, 7 β ,15 α ‐dihydroxylup‐20(29)‐ene‐3 β ‐ O ‐palmitate ( 2 ), lupeol palmitate ( 3 ), lupeol ( 4 ), 3‐oxolup‐20(29)‐ene ( 5 ), ursolic acid ( 6 ), cycloeucalenol ( 7 ), stigmasterol ( 8 ), β ‐sitosterol ( 9 ), β ‐daucosterol ( 10 ), quercetin ( 11 ), quercetin 3‐ O ‐ α ‐ L ‐arabinoside ( 12 ), quercetin 3‐ O ‐ α ‐ L ‐rhamnoside ( 13 ), catechin ( 14 ), gitoxigenin 3‐ O ‐ α ‐ L ‐rhamnoside ( 15 ), gitoxigenin 3‐ O ‐ α ‐ D ‐glucoside ( 16 ), and digitoxigenin 3‐ O ‐ α ‐ L ‐rhamnoside ( 17 ), was isolated from the leaves of the Southern China mistletoe, Scurrula parasitica Linn parasitic on Nerium indicum Mill . Their structures were elucidated by spectroscopic analyses, including 2D‐NMR techniques. Cytotoxic activities of compounds 1 – 7 and 11 – 17 were evaluated against three cancer cell lines, PANC‐1, HL‐60, and SGC‐7901, revealing that compounds 4, 6, 11 , and 15 – 17 exhibited effective cytotoxicities, while others were inactive. A structureactivity relationship study of compounds 1 – 5 indicated that the 3‐OH group in lupeol‐based triterpenoids is essential for antitumor activity.