Bioactive steroidal alkaloids from Sarcococca hookeriana.

Institute of Forestry, Pokhara Campus, Tribhuvan University, Pokhara, Kaski, Nepal.
Planta Medica (Impact Factor: 2.35). 02/2010; 76(10):1022-5. DOI: 10.1055/s-0029-1240896
Source: PubMed

ABSTRACT Four new 5 alpha-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 (IC (50) = 9.59 microg/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.

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    ABSTRACT: Fourteen pregnane-type steroidal alkaloids were isolated from the ethanolic extracts of whole Sarcococca hookeriana var. digyna plants. Their structures were elucidated on the basis of spectral data. Three of them were identified as new steroidal alkaloids: (20S)-20-(N,N-dimethylamino)-16α,17α-epoxy-3β-methoxy-pregn-5-ene (1), (20S)-20-(N,N-dimethylamino)-3β-tigloylamino-5α-pregn-11β-ol (2), and (20S)-2α,4β-bis(acetoxy)-20-(N,N-dimethylamino)-3β-tigloylamino-5α-pregnane (3). Some of the isolated compounds showed estrogen biosynthesis-promoting effects in human ovarian granulosa-like KGN cells. The EC50 values for the most effective compounds, vagnine B (6) and (20S)-20-(N, N-dimethylamino)-5α-pregnane (12), were 71 μM and 67 μM, respectively.
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