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Phytochemical investigations on six medicinal plants
Mohammad Nur-e-AlamSchool of ChemistryBangor University
Carduus crispus (500 g)
Extracted with MeOH
MeOH Extract (34.5 g)
Subjected to column chromatography
Partitioned between H2O and CHCl3
n-Hexane Fraction (3.6 g) H2O Part
CHCl3 Fraction (6.9 g) H2O part
Partitioned between H2O and ethyl acetate
Ethyl acetate Fraction (4.8 g) H2O part
Subjected to column chromatography
Carduusine (18)Apiginine (21)Chrysoeriol (25)Apigininrhamnoside (22)
Apigininglucoside 23Chrysoeriolgalactoside 26Apiginingalactoside 24Carduuside A 19Carduuside B 20
Partitioned between H2O and n-Hexane
Extraction and Isolation in Carduus crispus
Carduuside A
EI MS Fragmentations
Important HOHAHA and HMBC Correlations
Carduuside B
Iris bungei Maxim (100 g)Extracted with MeOH and concentrated to a gumunder reduced pressurs
MeOH Extract (8.1 g)
Subjected to colum chromatography on silica gel
100% CHCl3Fr-1
100% CHCl3Fr-2
99:1CHCl3:MeOHFr-3
98:2CHCl3:MeOHFr-4
97:3CHCl3:MeOHFr-5
TLC with impre-gnated with AgNO3
TLC with impre-gnated with AgNO3
Bungeiquinone (1)Dihydrobungeiquinone (2)
3-Hydroxyirisquinone (3)3-Hydroxydihydroirisquinone (4)
2nd column with silicasolvent Hexane:EtOAc(2:3)
Fr 3.1HPLC withRP-18 column
Irisf lavone A (5)Irisf lavone B (6)Irilin C (17)
Fr 3.2HPLC withRP-18 column
Irisf lavone C (7)Irisf lavone D (8)Irilin A (15)Irilin D (16)
3rd column with silicasolvent Hexane:EtOAc(2:3)
Fr 4.1HPLC withRP-18 column
Irisoid B (10)Irisoid D (12)
Irisoid C (11)Irisoid E (13)
HPLC withRP-18 column
Irisoid A (9)Irilin D (14)
Fr 4.2HPLC withRP-18 column
Extraction and Isolation Scheme of Iris bungei
Iris bungei, Mongolian medicinal Plant
Quinones
O
O
H3CH2CO
O
O
H3CO
O
O
H3CH2CO
O
O
H3CO
Nur-e-Alam M, et. al. Chem. Pharm. Bull. 48, 2000; 738-739
Iris bungei, Mongolian Medicinal Plant
Flavones
O O
O O
O O
O O
HO
H3CO
OH
OCH3
HO
H3CO
H3CO
OH
OCH3
HO
H3CO
H3CO
OH
OCH3
HO
OH
H3CO
OH
OH
H3CO
OH
Nur-e-Alam M, et. al. J. Nat. Prod. 64, 2001; 857-860
X-ray Crystal Structure of 5, 7 & 8
A molecule of DMSO is visible as solvent of crystallization
Iris bungei, Mongolian Medicinal Plant
Peltogynoids O
O
O
HO
OH
O
O
O
HO
OH
O
O
O
HO
OCH3
O
O
O
HO
OH
O
O
O
HO
OH
HO
H3CO
H3CO
H3CO
HO
H3CO
O
O
O
O
OH
Nur-e-Alam M, et. al. Chem. Pharm. Bull., 49, 2001; 1295-1298
X-ray Crystal Structure of 10
Crystal System:Monoclinic. Space group:P21/n, Final R factor: 0.0438
Iris bungei, Mongolian Medicinal Plant
IsoflavonesO
OOH
H3CO
HO O
OOH
H3CO
HO
OH
O
OOH
H3CO
H3CO
OH O
OOCH3
OCH3
OH
OH
O
O
Nur-e-Alam M, et. al. J. Nat. Prod. 64, 2001; 857-860
Withania coagulans, Pakistani medicinal plant
O
OO
O O
O
O
O
O
O
O
O
H3CO
OCH3
OCH3
H3CO
OCH3
OCH3
HO
OHOH
OH
OH
HOHO
OH
UV, MeOH (log e):325 nm (3.84) and 276 (3.91) IR: 3616-3225 (OH),2839 (CH), 1772 (C=O) and 1517 (C=C)FAB-ve MS: 1151, Base Peak m/z 414HR-MS m/z 1151.3625, MF C56H64O26, (Calcd. 1151.3686)
1H-NMR and 13C-NMR
O
OO
O O
O
O
O
O
O
O
O
H3CO
OCH3
OCH3
H3CO
OCH3
OCH3
HO
OH
OH
OH
OH
HO
HO
OH
5.88 (d, 1.5) & 5.86, (d, 1.5)
6.49 (s)4.26 (d, 6.5)
3.62 (dd, 6.5 & 9.5)
5.23 (dd, 2.5 & 9.5) & 4.52 (dd, 2.5 & 6.5)
3.16 (dddd, 2, 6, 9 & 11)
5.16 (d, 9) 7.90 (s)
6.87 (s)
5.22 (d, 7.5)
4.17 (m)
4.24 (m)
3.99 (m)4.28 (m)
4.34 & 4.51 (m)
3.73 (s)
3.87 (s)
101.4
147.5
108.4
132.1
44.8
45.3
178.3
70.2
42.7
78.6
132.5
108.1
147.6
139.4
107.1
154.2
137.5
56.3
60.5
105.6
75.4
78.6
71.7
78.7
62.8
Important HMBC Corelation
O
OO
O O
O
O
O
O
O
O
O
H3CO
OCH3
OCH3
H3CO
OCH3
OCH3
HO
OHOH
OH
OH
HOHO
OH
Nur-e-Alam M, et. al. Helv. Chim,. Acta, 86, 2003; 607-614
Compounds from Sophora alopecuroides
Nur-e-Alam M, et. al. J. Nat. Prod. 63, 2000; 190-192
HMBC and X-ray Stracture of Novel compounds
Novel compounds from Ferula mongolica
Ferula mongolica
Nur-e-Alam M, et. al. Helv. Chim,. Acta, 84, 2001; 2409-2416
Thank You
Acknowledgements:Professor M Iqbal ChaudharyProfessor Att-ur-Rahmanand others lebfellows
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