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A new lupane caffeoyl ester, lup-20(29)-ene 3β-caffeate-30-al ( 7 ), and a new oleanane-type triterpene, 3 β -hydroxyolean-13(18)-en-12-one ( 17 ), were isolated from the aerial parts of  Dobera glabra  (Forssk), along with ten known triterpenes, including seven lupane-type lupeol ( 1 ), 30-nor-lup-3 β -ol-20-one ( 2 ), ∆ 1 -lupenone ( 3 ), lup-20(29)-en-3 β ,30-diol ( 4 ), lupeol caffeate ( 5 ), 30-hydroxy lup-20(29)-ene 3 β -caffeate ( 6 ), and betunaldehyde ( 8 ); three oleanane-type compounds were also identified, comprising  δ -amyrone ( 15 ),  δ -amyrin ( 16 ), and 11-oxo- β -amyrin ( 18 ); together with six sterols, comprising  β -sitosterol ( 9 ), stigmasterol ( 10 ), 7 α -hydroxy- β -sitosterol ( 11 ), 7 α -hydroxy-stigmasterol ( 12 ), 7-keto- β -sitosterol ( 13 ), and 7-keto-stigmasterol ( 14 ). Their structures were elucidated using a variety of spectroscopic techniques, including 1D ( 1 H,  13 C, and DEPT-135  13 C) and 2D ( 1 H– 1 H COSY,  1 H– 13 C HSQC, and  1 H– 13 C HMBC) nuclear magnetic resonance (NMR) and accurate mass spectroscopy. Subsequently, the different plant extracts and some of the isolated compounds ( 1–9 ,  11  and  13 ) were investigated for their possible cytotoxic activity in comparison to cisplatin against a wide array of aggressive cancer cell lines, such as colorectal cancer (HCT-116), hepatocellular carcinoma (HepG-2), and prostate cancer (PC-3) cell lines. Compound  11  displayed broad cytotoxicity against all of the tested cell lines (IC 50  ≅ 8 µg/mL in all cases), and a high safety margin against normal  Vero  cells (IC 50  = 70 µg/mL), suggesting that  11  may be a highly selective and effective anticancer agent candidate. Notably, the evidence indicated that the mode of action of compound  11  could possibly consist of the inhibition of phosphodiesterase I (80.2% enzyme inhibition observed at 2 µM compound concentration).

Sterols and Triterpenes from Dobera glabra Growing in Saudi Arabia and Their Cytotoxic Activity