Cytotoxic Aryltetralin Lignans from Fruits of Cleistanthus indochinensis

Abstract

Eight new aryltetralin lignans, cleisindosides A-F (1-6), picroburseranin (7), and 7-hydroxypicropolygamain (8), were isolated from the fruits of Cleistanthus indochinensis (Euphorbiaceae). The structures of the isolates were established on the basis of their one- and two-dimensional NMR spectral data, as well as their mass spectrometric data. Compound 7 was found to have potent cytotoxicity against oral epidermoid carcinoma cells with an IC50 value of 0.062 µM, whereas glycosylation to 3 (IC50 7.5 µM) and stereochemical changes to 8 (IC50 10.8 µM) led to marked decreases in biological activity. Thus, it was determined that the C-7 and C-8' positions are critical for the biological activity of the lignans from this plant.

Cyclolignan Synthesis Streamlined by Enantioselective Hydrogenation of Tetrasubstituted Olefins

“…In addition, a thermal retro-aldol reaction of 9 afforded isopicropodophyllone (15), which could be reduced to generate either epiisopicropodophyllotoxin (16) 52 or epiisopicrodeoxypodophyllotoxin (17). Using this new protocol from either 2k′ or 2l′, we also synthesized β-peltatin-A-methyether (18) and accomplished the rst total syntheses of epiisopicropodophyllotoxin (16), 6-methoxypodophyllotoxin (19), 6methoxypodophyllotoxin-7-O-n-hexanoate (20), 53 cleistantoxin (21), 54 and picrobursenin ( 22) 55 (Fig. 3b).…”

Chemistry and Biology of Podophyllotoxins: An Update

“…Among them, compounds 5, 9 and 10 were highly cytotoxic to oral epidermoid carcinoma KB cells with IC 50 values of 7.5, 0.062, and 10.8 μM, respectively. [12] In addition, from the leaves of C. boivinianus, 3α-O-(β-Dglucopyranosyl)desoxypodophyllotoxin (11) and 4-O-(β-Dglucopyranosyl)dehydropodophyllotoxin (12) were obtained. Compound 11 showed good anticancer activities with IC 50 values of 33.0 and 20.5 nM against ovarian cancer cells A2780 and human colon cancer cells HCT-116, respectively.…”

“…As described in Figure 2, cleisindosides A ( 3 ), cleisindosides B ( 4 ), cleisindosides C ( 5 ), cleisindosides D ( 6 ), cleisindosides E ( 7 ), cleisindosides F ( 8 ), picroburseranin ( 9 ) and 7‐hydroxypicropolygamain ( 10 ) were isolated from the fruits of Cleistanthus indochinensis . Among them, compounds 5 , 9 and 10 were highly cytotoxic to oral epidermoid carcinoma KB cells with IC 50 values of 7.5, 0.062, and 10.8 μM, respectively [12] . In addition, from the leaves of C. boivinianus , 3 α ‐O‐( β ‐D‐glucopyranosyl)desoxypodophyllotoxin ( 11 ) and 4‐O‐( β ‐D‐glucopyranosyl)dehydropodophyllotoxin ( 12 ) were obtained.…”

Φυτοχημική μελέτη και έλεγχος βιολογικής δράσης του είδους Staehelina uniflosculosa Sibth. & Sm. της οικογένειας Asteraceae

“…Κάποιες μελέτες αναφέρουν λίγο διαφορετικά τη δράση αυτή, ως αντικυτταροτοξική (Cao et al, 2015). Για παράδειγμα, η πικροβουρσερανίνη εμφανίζει κυτταροτοξική δράση έναντι των επιδερμικών κυττάρων του καρκινώματος στο στόμα (Trinh Thi Thanh et al, 2014 (Slanina, 2000, Seibold et al, 2014. Με άλλα λόγια, τα λιγνάνια μπορούν και να δρουν μέσω των οιστρογόνων αναστέλλοντας τον πολλαπλασιασμό, την απόπτωση και μειώνοντας την έκφραση του ανθρώπινου επιδερμικού αυξητικού παράγοντα.…”