Bioactive Steroidal Alkaloids from Sarcococca hookeriana

Abstract

Four new 5α-pregnane-type steroidal alkaloids, hookerianamides L (1), M (2), N (3), and O (4), and a known N-formylchonemorphine (5) have been isolated by acid-base extraction of the dichloromethane extract of Sarcococca hookeriana. The structures of all compounds were determined with spectroscopic techniques and by comparison with literature data. All compounds displayed antileishmanial and antibacterial properties. Compounds 1, 4, and 5 were found to be more potent than standard pentamidine (IC₅₀ = 9.59 µg/mL) with respect to leishmanicidal activity. The minimum inhibitory concentration of most of the compounds against Bacillus subtilis, Streptococcus minor, and Streptococcus ferus was lower than that of the standard ampicillin.

Key words

Buxaceae - Sarcococca hookeriana - steroidal alkaloids - antileishmanial - antibacterial

References

• 1 Naeem I, Khan N, Choudhary M I, Atta-ur-Rahman. Alkaloids of Sarcococca saligna.  Phytochemistry. 1996;  43 903-906
• 2 Atta-ur-Rahman, Anjum S, Farooq A, Khan M R, Choudhary M I. Two new pregnane-type steroidal alkaloids from Sarcococca saligna.  Phytochemistry. 1997;  46 771-775
• 3 Shah G M, Khan A. Common medicinal folk recipes of Siran Valley. Mansehra, Pakistan. http://www.siu.edu/~ebl/leaflets/ghulam.htm Accessed October 10, 2006
• 4 Yu S S, Zou Z M, Jie Z, Yu D Q, Cong P Z. Four new steroidal alkaloids from the roots of Sarcococca vagans.  Chin Chem Lett. 1997;  8 511-514
• 5 Rajbhandari K R. Ethnobotany of Nepal. Kathmandu; Ethnobotanical Society of Nepal c/o Central Department of Botany, Tribhuvan University, Kirtipur 2001
• 6 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
• 7 Devkota K P, Choudhary M I, Ranjit R, Khan S, Sewald N. Structure activity relationship studies on antileishmanial steroidal alkaloids from Sarcococca hookeriana.  Nat Prod Res. 2007;  21 292-297
• 8 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
• 9 Devkota K P, Lenta B N, Wansi J D, Choudhary M I, Kisangau D P, Naz Q, Khan S, Sewald N. Bioactive 5α-pregnane-type steroidal alkaloids from Sarcococca hookeriana.  J Nat Prod. 2008;  71 1481-1484
• 10 Devkota K P, Lenta B N, Fokou P A, Sewald N. Terpenoid alkaloids of the Buxaceae family with potential biological importances.  Nat Prod Rep. 2008;  25 612-630
• 11 Choudhary M I, Devkota K P, Nawaz S A, Ranjit R, Atta-ur-Rahman. Cholinesterase inhibitory natural pregnane-type steroidal alkaloids from Sarcococca hookeriana.  Steroids. 2005;  7 295-303
• 12 Choudhary M I, Devkota K P, Nawaz S A, Shaheen F, Atta-ur-Rahman. Cholinesterase-inhibiting new steroidal alkaloids from Sarcococca hookeriana of Nepalese origin.  Helv Chim Acta. 2004;  87 1099-1108
• 13 Perez C, Paul M, Bazerque P. Antibiotic assay by agar well diffusion method.  Acta Biol Med Exp. 1990;  15 113-115
• 14 Parekh J, Chanda S. In vitro antimicrobial activity and phytochemical analysis of some Indian medicinal plants.  Turk J Biol. 2007;  31 53-58
• 15 Zou Z M, Li L J, Yang M, Yu S S, Cong P Z, Yu D Q. Steroidal alkaloids from roots of Sarcococca vegans.  Phytochemistry. 1997;  46 1091-1093
• 16 Choudhary M I, Shahnaz S, Parveen S, Khalid A, Mesaik M A, Ayatollahi S A M, Atta-ur-Rahman. New cholinesterase-inhibiting triterpenoid alkaloids from Buxus hyrcana.  Chem Biodivers. 2006;  3 1039-1052
• 17 Funayama S, Noshita T, Shinoda K, Haga N, Nozoe S, Hayashi M, Komiyama K. Cytotoxic alkaloids of Pachysandra terminalis.  Biol Pharm Bull. 2000;  23 262-264