Mustafa Kemal TAŞKIN, Özgen Alankuş ÇALIŞKAN, Hüseyin ANIL, Hassan ABOU-GAZAR, Ikhlas A. KHAN, Erdal BEDİR

Triterpene Saponins from Nigella sativa L.

Three known triterpene glycosides were isolated from the MeOH extract of dried and powdered seeds of Nigella sativa. The structures of the compounds were established as 3-O-[b-D-xylopyranosyl- (1 \to 3)-a-L-rhamnopyranosyl-(1 \to 2)-a -L-arabinopyranosyl]- 28-O-[a-L-rhamnopyranosyl-(1 \to 4)-b-D-glucopyranosyl-(1 \to 6)- b-D-glucopyranosyl]-hederagenin (1), 3-O-[a -L-rhamnopyranosyl- (1 \to 2)-a-L-arabinopyranosyl]-28-O-[a -L-rhamnopyranosyl-(1 \to 4)- b-D-glucopyranosyl-(1\to 6)-b-D-glucopyranosyl]-hederagenin (2), and 3-O-[b-D-xylopyranosyl- (1\to 3)-a-L-rhamnopyranosyl-(1\to 2)-a- L-arabinopyranosyl]-hederagenin (3) by means of chemical and spectral methods. Compound 2 was isolated for the first time from the genus Nigella.

Anahtar Kelimeler:

Ranunculaceae, Nigella sativa, Saponins, Triterpene glycoside, hederagenin

Triterpene Saponins from Nigella sativa L.

Keywords:

Ranunculaceae, Nigella sativa, Saponins, Triterpene glycoside, hederagenin,

PDF

___

T. Baytop, “Therapy with Medicinal Plants in Turkey (Past and Present)” 2nded. p.p. 189 Nobel Tıp Kitapevleri, Ltd. ˙Istanbul (1999).
E. Sezik, E. Ye¸silada, G. Honda, Y. Takaishi, Y. Takeda and T. Tanaka, J. Ethnopharmacol. 75, 95-115 (2001).
B.E. Abu-Irmaileh and F.U. Afifi, J. Ethnopharmacol. 89, 193-197 (2003).
M.L. Leporatti and S. Ivancheva, J. Ethnopharmacol. 87, 123-142 (2003).
M. Eddouks, M. Maghrani, A. Lemhadri, M.L. Ovahidi and H. Jovad, J. Ethnopharmacol. 82, 97-103 (2002).
O. Said, K. Khalil, S. Fulder and H. Azaizeh, J. Ethnopharmacol., 83, 251-265 (2002).
E. Lev, J. Ethnopharmacol. 80, 167-179 (2002).
N.J. Salomi, S.C. Nair, K.K. Jayawardhanon, C.D. Varghese and K.R. Panikkar, Cancer Lett. 63(1), 41-46 (1992).
M.S. Al-Ghamdi, J. Ethnopharmacol. 76, 45-48 (2001).
H.S. El-Abhar, D.M. Abdallah and S. Saleh, J. Ethnopharmacol. 84, 251-258 (2003).
M.R. Mahmoud, H.S. El-Abhar and S. Saleh, J. Ethnopharmacol. 79, 1-11 (2002).
A. Al-Hader, M. Aqel and Z. Hasan, Int. J. Pharmacog. 31, 96-100 (1993).
S.M.K. Swamy and B.K.H. Tan, J. Ethnopharmacol. 70, 1-7 (2000).
O.A. Badary, J. Ethnopharmacol. 67, 135-142 (1999).
M.H. Daba and M.S. Abdel-Rahman, Toxicol. Lett. 95, 23-29 (1998).
M.N. Nagi, K. Alam, O.A. Badary, O.A. Al-Shabanah, H.A. Al-Sawaf and A.M. Al-Bekairi, Biochem. Mol. Biol. Int. 47, 153-159 (1999).
T. Morikawa, F. Xu, Y. Kashima, H. Matsuda, K. Ninomiya and M. Yoshikawa, Org. Lett. 6, 869-872 (2004).
P.J. Houghton, R. Zarka, B. Heras and J.R.S. Hoult, Planta Med. 61, 33-36 (1995).
S.A.A. Jassim and M.A. Naji, J. Appl. Microbiol. 95, 412-427 (2003).
M.S.M. Hanafy and M.E. Hatem, J. Ethnopharmacol. 34, 275-278 (1991).
A.J. Ferdous, S.N. Islam, M. Ahson, C.M. Hasan and Z.U. Ahmed, Pytother. Res. 6, 137-140 (1992).
Atta-ur-Rahman, S. Malik, S. Ahmed, SM.I. Choudhary and Habib-ur-Rahman, Heterocycles 23, 953-955 (1985).
Atta-ur-Rahman, S. Malik, H. Cun-heng and J. Clardy, Tetrahedron Lett. 23, 2559-2762 (1985).
Atta-ur-Rahman, S. Malik, S.S. Hasan, M.I. Choudhary, C.Z. Ni and J. Clardy, Tetrahedron Lett. 36, 1996 (1995).
Atta-ur-Rahman, S. Malik and K. Zaman, J. Nat. Prod. 55, 676-678 (1992).
T. Morikawa, F. Xu, Y. Kashima, H. Matsuda, K.Y. Ninomiya and M. Yoshikawa, Org. Lett. 6, 869-872 (2004).
T. Morikawa, F. Xu, K. Ninomiya, H. Matsuda and M. Yoshikawa, Chem. Pharm. Bull. 52, 494-497 (2004).
I. Merfort, V. Wray, H.H. Barakat, A.M. Hussein, M.A.M. Nawwar and G. Willuhn, Phytochemistry 46, 363 (1997).
A.A. Ansari, S. Hassan, L. Kene, L., Atta-ur-Rahman and T. Wehler, Phytochemistry 27, 3977-3979 (1988).
S. Swamy, M. Kumara and B.T.K. Huat, Planta Med. 67, 29-32 (2001).
B.S. Joshi, K.L. Singh and R. Roy, Magn. Reson. Chem. 39, 771-772 (2001).
C. Nergiz and S. ¨Otles, Food Chem. 48, 259-261 (1993).
P.K. Agrawal, Phytochemistry 31, 3307 (1992).
X.C. Li, D.Z. Wong, S.G. Wu and C.B. Yong, Phytochemistry 29, 595-599 (1990).
R. Higuchi and T. Kawasaki, Chem. Pharm. Bull. 24, 1021-1032 (1976).
S.B. Mahato, N.P. Sahu, S.K. Roy, S. Sen, Tetrahedron 47, 5215-5230 (1991).
C. Lavaud, M.L. Crublet, I. Pouny, M. Litaudon and T. S´evenet, Phytochemistry 57, 469-478 (2001).
A.B. Singab, T.I. Khalifa, T. Okuyama and S. Fushiya, Al-Azhar J. Pharm. Sci. 24, 1-9 (1999).