Cytotoxic Steroids from Sarcococca saligna

Abstract

Two new C₂₁-steroidal esters, sarsaligates A (1) and B (2), and two new steroidal alkaloids, sarsaligenines A (3) and B (4), together with four known compounds (sarcovagine, sarcorucinine, dimethylamino-3β-pregnane-20-one, and β-sitosterol 5–8, respectively), were isolated from the leaves and stems of Sarcococca saligna. The structures of compounds 1–4 were elucidated by NMR and MS spectroscopic analysis. Of the compounds tested, 5 and 6 were the most cytotoxic against the cell lines K562, SK-BR-3, and PANC-1, with IC₅₀ values in the range of 2.25–5.00 µM, while 3 and 4 selectively inhibited HL-60 cells with IC₅₀ values of 2.87 and 3.61 µM, respectively. Compounds 3–6 therefore deserve further evaluation of their cytotoxic potentials.

Buxaceae - Sarcococca saligna - sarsaligates A/B - sarsaligenines A/B - cytotoxicity

References

• 1 Atta-ur-Rahman, Anjum S, Farooq A, Khan M R, Parveen Z, Choudhary M I. Antibacterial steroidal alkaloids from Sarcococca saligna.  J Nat Prod. 1998;  61 202-206
• 2 Devkota K P, Lenta B N, Wansi J D, Choudhary M I, Kisangau D P, Naz Q, Samreen, Sewald N. Bioactive 5α-pregnane-type steroidal alkaloids from Sarcococca hookeriana.  J Nat Prod. 2008;  71 1481-1484
• 3 Atta-ur-Rahman, Feroz F, Naeem I, Zaheer-ul-Haq, Nawaz S A, Khan N, Khan M R, Choudhary M I. New pregnane-type steroidal alkaloids from Sarcococca saligna and their cholinesterase inhibitory activity.  Steroids. 2004;  69 735-741
• 4 Atta-ur-Rahman, Zaheer-ul-Haq, Feroz F, Khalid A, Nawaz S A, Khan M R, Choudhary M I. New cholinesterase-inhibiting steroidal alkaloids from Sarcococca saligna.  Helv Chim Acta. 2004;  87 439-448
• 5 Devkota K P, Lenta B N, Choudhary M I, Naz Q, Fekam F B, Rosenthal P J, Sewald N. Cholinesterase inhibiting and antiplasmodial steroidal alkaloids from Sarcococca hookeriana.  Chem Pharm Bull. 2007;  55 1397-1401
• 6 Gilani A H, Ghavur M N, Khalid A, Zaheer-ul-Haq, Atta-ur-Rahman. Presence of antispasmodic, antidiarrheal, antisecretory, calcium antagonist and acetylcholinesterase inhibitory steroidal alkaloids in Sarcococca saligna.  Planta Med. 2005;  71 120-125
• 7 Qiu M H, Nie R L, Li Z R. Structure and biological of Pachysandra alkaloids.  Acta Bot Yunn. 1994;  16 296-300
• 8 Yu S S, Zou Z M, Zen J, Yu D Q, Cong P Z. Steroidal alkaloids from roots of Sarcococca vagans.  Chin Chem Lett. 1997;  8 511-514
• 9 Qiu M H, Nie R L, Zhou J. Application of FAB-MS/MS technique in structural determination of sarcorucinine A and A1.  Acta Bot Yunn. 1991;  13 445-451
• 10 Schmitt J, Panouse J J, Hallot A, Comoy P, Pluchet H, Cornu P J. Sankar amino steroids. II. 3-Substituted amino steroids.  Bull Soc Chim Fr. 1962;  463-470
• 11 Alley M C, Scudiero D A, Monks A. Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay.  Cancer Res. 1988;  48 589-601
• 12 Reed L J, Muench H. A simple method of estimating fifty percent endpoints.  Am J Hyg. 1938;  27 493-497
• 13 Zou Z M, Li L J, Yang M, Yu S S, Cong P Z, Yu D Q. Steroidal alkaloids from roots of Sarcococca vagans.  Phytochemistry. 1997;  46 1091-1093
• 14 Qiu M H, He C H, Nie R L, Zheng Q T, Zhou J. The structure of sarcorucinine A.  Acta Bot Yunn. 1990;  12 111-112