Abstract
The cytotoxic structure-activity relationships among a series of xanthone derivatives from Mesua beccariana, Mesua ferrea and Mesua congestiflora were studied. Eleven xanthone derivatives identified as mesuarianone (1), mesuasinone (2), mesuaferrin A (3), mesuaferrin B (4), mesuaferrin C (5), 6-deoxyjacareubin (6), caloxanthone C (7), macluraxanthone (8), 1,5-dihydroxyxanthone (9), tovopyrifolin C (10) and α-mangostin (11) were isolated from the three Mesua species. The human cancer cell lines tested were Raji, SNU-1, K562, LS-174T, SK-MEL-28, IMR-32, HeLa, Hep G2 and NCI-H23. Mesuaferrin A (3), macluraxanthone (8) and α-mangostin (11) showed strong cytotoxicities as they possess significant inhibitory effects against all the cell lines. The structure-activity relationship (SAR) study revealed that the diprenyl, dipyrano and prenylated pyrano substituent groups of the xanthone derivatives contributed towards the cytotoxicities.
Highlights
The genus Mesua, from the Clusiaceae family was selected for preliminary pharmacognosy analysis as some previous chemical investigations on this genus have revealed their activities to be due to the phloroglucinols, xanthones and neoflavonoids present in these plants [1,2,3]. 6-Deoxyjacareubin (6) has been reported for its growth inhibitory effect against HL-60 cells [4], antioxidant activity [5]
We report here the biological activities for compounds 1–11 (Figure 1) as well as the structure-activity relationship (SAR)
Cytotoxicities of all the isolated xanthone derivatives were evaluated against a panel of cancer cell lines which included Raji, SNU-1, K562, LS-174T, HeLa, SK-MEL-28, NCI-H23, IMR-32 and Hep G2
Summary
The genus Mesua, from the Clusiaceae family was selected for preliminary pharmacognosy analysis as some previous chemical investigations on this genus have revealed their activities to be due to the phloroglucinols, xanthones and neoflavonoids present in these plants [1,2,3]. 6-Deoxyjacareubin (6) has been reported for its growth inhibitory effect against HL-60 (leukemia) cells [4], antioxidant activity [5]. 6-Deoxyjacareubin (6) has been reported for its growth inhibitory effect against HL-60 (leukemia) cells [4], antioxidant activity [5]. As well as platelet-activating factor receptor binding inhibitory effects [6,7]. There are reports on caloxanthone C (7) and macluraxanthone (8) having good activities on Plasmodium falciparum [8]. Macluraxanthone (8) has been reported to exhibit potent cholinesterase inhibitory [9], strong antioxidant and cytotoxic activities [10]. Α-Mangostin (11) showed anti-proliferative and pro-apoptotic effects on chronic B leukemia cells [12] and was cytotoxic on canine osteosarcoma D-17 cells [13]. The biological activities of compounds 1–5 and 10 have not been reported. We report here the biological activities for compounds 1–11 (Figure 1) as well as the SAR for these compounds
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