Spectroscopic Data of Steroid Glycosides (eBook)

Professor Viqar Uddin Ahmad has been associated with the HEJ Research Institute of Chemistry since its establishment in 1967. Prof. Viqar's currents interests are on isolation and structure elucidation of new natural products. Some of them have interesting biological activities. For example: VArious eudesmane sesquiterpenes which showed antibacterial activity against Escherichia coli, Klebsiella ozaenoe, K. pneumonieae, Proteus vulgaris, Shigella boddi, Staphylococcus aureus, S. pyogenes andB. anthracis; some triterpenoidal and steroidal saponins exhibited toxicity in Brine Shrimp Lethality bioassay and antibacterial activity against Pseudomonas pseudomaliae, Co-rynebactterium xerosis etc. One of the saponins isolated from a Trukish plant manifested hypotensive activity in anaesthetized rat. Prof. Viqar Uddin Ahmad availed a Fulbright Fellowship of nine months in 1993. during his stay at Cornell University, Itacha, USA. Prof. Viqar Uddin Ahmad worked on the twelve step total synthesis of and alkaloid isolated from an insect. Prof. Viqar also dilivered lecturers in the chemistry departments of Central Michighan University, Michighan, Georgia Tech, Atlanta, georgia, State University, Atlanta, Georgia and Cornell University, Ithaca.

PREFACE 6
ABBREVIATIONS 8
CONTENTS 10
Miscellaneous Steroids 11
GYMNEPREGOSIDE O 11
TELOSMOSIDE A11 12
ASCLEPIAS FRUTICOSA SAPONIN 12 14
ASCLEPIAS FRUTICOSA SAPONIN 13 15
ASCLEPIAS INCARNATA SAPONIN 78 17
ASCLEPIAS INCARNATA SAPONIN 93 18
TELOSMOSIDE A12 20
HOYACARNOSIDE K 21
ASCLEPIAS INCARNATA SAPONIN 79 23
ASCLEPIAS FRUTICOSA SAPONIN 16 24
HOYACARNOSIDE T 25
ASCLEPIAS INCARNATA SAPONIN 92 26
CYNAFOSIDE D 28
ARAUJIA SERICIFERA GLYCOSIDE 16 29
GYMNEPREGOSIDE L 31
LEPTADENIA HASTATA SAPONIN 25 32
CAUSIAROSIDE II 33
TACCA CHANTRIERI SAPONIN 8 35
STEPHANOSIDE P 36
GYMNEMAROSIDE B 37
HAINANEOSIDE B 39
MARSTOMENTOSIDE O 40
MARSTOMENTOSIDE P 42
PERIPLOCOSIDE F 43
AURICULOSIDE A 44
CYNANCHUM CAUDATUM SAPONIN 61 46
CYNANCHUM CAUDATUM SAPONIN 64 47
WILFOSIDE C 1G 48
NIGROSIDE A 50
ASCLEPIAS FRUTICOSA SAPONIN 14 51
ASCLEPIAS FRUTICOSA SAPONIN 15 52
TEIKASIDE B-IVa 54
ASCLEPIAS INCARNATA SAPONIN 16 55
ASCLEPIAS INCARNATA SAPONIN 17 56
ASCLEPIAS FRUTICOSA SAPONIN 17 57
ASCLEPIAS FRUTICOSA SAPONIN 18 58
CYNAFOSIDE C 59
LEPTADENIA HASTATA SAPONIN 30 60
ARAUJIA SERICIFERA GLYCOSIDE 20 62
LEPTADENIA HASTATA SAPONIN 14 63
HAINANEOSIDE A 64
DREGEOSIDE AO1 66
ASCLEPIAS INCARNATA SAPONIN 23 67
ASCLEPIAS INCARNATA SAPONIN 24 69
WALLICOSIDE 70
ASCLEPIAS FRUTICOSA SAPONIN 19 71
ASCLEPIAS FRUTICOSA SAPONIN 20 73
ASCLEPIAS FRUTICOSA SAPONIN 21 74
ASCLEPIAS INCARNATA SAPONIN 90 75
CYNAURICUOSIDE A 76
ASCLEPIAS INCARNATA SAPONIN 18 78
ASCLEPIAS INCARNATA SAPONIN 19 79
ASCLEPIAS TUBEROSA SAPONIN 10 80
TELOSMOSIDE A5 81
ARAUJIA SERICIFERA GLYCOSIDE 21 83
METAPLEXIS JAPONICA SAPONIN 24 84
HOYACARNOSIDE M 85
ASCLEPIAS INCARNATA SAPONIN 25 87
LEPTADENIA HASTATA SAPONIN 15 88
LEPTADENIA HASTATA SAPONIN 32 89
LEPTADENIA HASTATA SAPONIN 10 91
LEPTADENIA HASTATA SAPONIN 27 92
ALPINOSIDE C 94
CYNAPHYLLOSIDE H 95
TELOSMOSIDE A3 97
CYNAFOSIDE H 98
PERIPLOCOSIDE E 100
TEIKASIDE C-IVa 101
HOYACARNOSIDE O 102
GYMNEPREGOSIDE I 104
GYMNEPREGOSIDE J 105
ALPINOSIDE A 107
LEPTADENIA HASTATA SAPONIN 13 108
LEPTADENIA HASTATA SAPONIN 28 110
MARSTENACISSIDE D 111
CONDURANGOGLYCOSIDE E3 113
CONDURANGOGLYCOSIDE A1 114
CONDURANGOGLYCOSIDE C1 116
ANASTEROSIDE B 117
ASCLEPIAS TUBEROSA SAPONIN 8 118
CYNANCHUM CAUDATUM SAPONIN 56 120
CYNANCHUM CAUDATUM SAPONIN 57 121
CYNANCHUM CAUDATUM SAPONIN 58 123
MARSTOMENTOSIDE A 124
PERIPLOCOSIDE K 126
ASCLEPIAS TUBEROSA SAPONIN 9 127
CYNANCHUM CAUDATUM SAPONIN 62 129
WILFOSIDE G 1G 130
CYNANCHUM CAUDATUM SAPONIN 65 132
CYNANCHUM CAUDATUM SAPONIN 67 133
CYNANCHUM CAUDATUM SAPONIN 70 135
TELOSMOSIDE A14 136
MARSTOMENTOSIDE K 138
MARSTOMENTOSIDE L 139
GYMNEPREGOSIDE B 141
GYMNEPREGOSIDE K 142
PERIPLOCOSIDE D 144
LEPTADENIA HASTATA SAPONIN 11 145
LEPTADENIA HASTATA SAPONIN 17 146
LEPTADENIA HASTATA SAPONIN 29 148
CYNANCHUM CAUDATUM SAPONIN 66 149
CYNANCHUM CAUDATUM SAPONIN 68 151
CYNANCHUM CAUDATUM SAPONIN 69 152
CYNANCHUM CAUDATUM SAPONIN 71 154
SIBIRICOSIDE E 155
ASCLEPIAS TUBEROSA SAPONIN 7 157
TELOSMOSIDE A15 158
TELOSMOSIDE A17 160
TELOSMOSIDE A16 162
GYMNEPREGOSIDE E 163
METAPLEXIS JAPONICA SAPONIN 25 165
METAPLEXIS JAPONICA SAPONIN 26 166
MARSTOMENTOSIDE Q 168
MARSTOMENTOSIDE G 169
ASCLEPIAS TUBEROSA SAPONIN 11 171
TELOSMOSIDE A18 173
ASCLEPIAS TUBEROSA SAPONIN 16 174
CESTRUM NOCTURNUM SAPONIN 8 176
PERIPLOCOSIDE A 177
MARSTOMENTOSIDE H 179
MARSTOMENTOSIDE I 181
GYMNEPREGOSIDE P 183
LEPTADENIA HASTATA SAPONIN 33 184
GYMNEPREGOSIDE M 186
GYMNEPREGOSIDE N 188
GYMNEPREGOSIDE Q 190
CYNANCHUM CAUDATUM SAPONIN 72 191
ASCLEPIAS TUBEROSA SAPONIN 12 193
CYNAURICUOSIDE C 195
ILLUSTROL 3-O- O- -D-CYMAROPYRANOSIDE 197
HIRUNDOSIDE A 198
AMALOSIDE A 199
CYNATRATOSIDE A 200
OLEASIDE A 201
CYNAPANOSIDE A 202
GLAUCOSIDE A 203
PANICULATUMOSIDE A 204
PANICULATUMOSIDE B 205
TYLOPHORISIDE A 206
OLEASIDE B 207
CYNAVERSICOSIDE C 208
NEOCYNAVERSICOSIDE 209
ATRATOGLAUCOSIDE A 210
AMALOSIDE B 211
OLEASIDE C 212
KOMAROSIDE A 213
OLEASIDE D 214
ATRATOSIDE D 215
CYNASCYROSIDE A 216
CYNASCYROSIDE D 217
CYNATROSIDE A 218
CYNATROSIDE C 219
ATRATOSIDE A 220
CYNATRATOSIDE B 221
CYNATRATOSIDE C 222
CYNATROSIDE B 223
TYLOPHOSIDE A 224
STAUNTOSIDE B 225
CYNAFORROSIDE A 226
CYNAPANOSIDE B 227
CYNAPANOSIDE C 228
GLAUCOSIDE C 229
GLAUCOSIDE D 230
GLAUCOSIDE G 231
CYNANVERSICOSIDE-A 232
CYNATRATOSIDE F 233
GLAUCOSIDE B 234
GLAUCOSIDE E 235
GLAUCOSIDE F 236
TYLOPHOSIDE B 237
TYLOPHOSIDE C 238
NEOCYNAPANOSIDE A 239
TYLOPHOSIDE D 240
ATRATOGLAUCOSIDE B 241
CYNAVERSICOSIDE D 242
KOMAROSIDE C 243
OLEASIDE E 244
KOMAROSIDE B 245
OLEASIDE F 246
CYNASCYROSIDE C 247
CYNASCYROSIDE E 248
CYNASCYROSIDE B 249
ATRATOSIDE C 250
ATRATOSIDE B 251
CYNATRATOSIDE D 252
CYNATRATOSIDE E 253
STAUNTOSIDE A 254
GLAUCOSIDE H 255
CYNANVERSICOSIDE-B 257
GLAUCOSIDE I 258
TYLOPHOSIDE E 259
GLAUCOSIDE J 260
CYNAVERSICOSIDE E 262
TYLOPHOROSIDE 263
ACETYLTYLOPHOROSIDE 264
VELUTINOSIDE A 266
ANDROSTANE 268
ASCANDROSIDE 268
ANDROST-8-EN-GLYCOSIDE 269
VERNONIA COLORATA GLYCOSIDE 2 270
LATESPINOSIDE D 271
VERNONIA COLORATA GLYCOSIDE 1 272
CAROLINOSIDE 273
COMPOUND NAME INDEX 274
PLANT SOURCE INDEX 360
REGISTRY NUMBER INDEX 395
MOLECULAR WEIGHT AND MOLECULAR FORMULA INDEX 507

"PREFACE (p. vi-vii)

The present volumes reproduce the spectroscopic data of naturally occurring steroidal glycosides as far as they are available in the chemical literature published until the end of 2004. Steroids have the basic skeleton of cyclopentanoperhydrophenanthrene. Generally they do not have methyl groups attached to C-4 and thus differ from triterpenes. Many of the steroidal glycosides, or saponins, have interesting biological activities and constitute the active principles of the natural drugs.

The cardiac glycosides (cardenolides) included in the present work act as life-saving medicines in certain ailments. Not included in this work are the glycosides of steroidal alkaloids. However, the compounds which contain a nitrogen atom in the sugar or in the ester moiety (e.g. nicotinoyl moiety) are included. The steroidal glycosides are arranged according to the class of their aglycones (steroidal parts). Within each class increasing molecular weight is taken as the basis for this arrangement. If the compounds of the same class have the same molecular weight, then the glycosides with lesser number of carbon atoms come earlier than those with more carbon atoms. Finally, if all these factors are the same, then the compounds are arranged in alphabetical order.

The chemical shifts in the proton nuclear magnetic resonance (PMR) spectral data are arranged according to the increasing δ (ppm) values. Each signal represents one proton unless indicated otherwise. The small alphabets used as superscript in PMR and 13C-NMR (CMR)-spectral data mean that the assignments are ambiguous and may be reversed with signals having the same superscripts. The signals masked by solvent peaks or by other signals of the compound are marked by an asterisk. Compounds can be easily located in this book with the help of the four indexes at the end of the last volume.

The trivial names of the compounds given by the original authors are used as the heading of the compound. If no trivial name has been given, then the name of the plant from which the glycoside has been isolated followed by the word “saponin” or “glycoside” and then the numerical order are used as the main heading. For the subheading, the name of the aglycone (trivial names if available) followed by names of the sugars are used with clear indication of glycosidic linkages and branching of the sugar chain if present.

I am very grateful to Ms. Judy Watson of Chemical Abstract Service who has helped me greatly in finding the registry numbers of several compounds. This work would not have been possible without the help of literature surveyors Dr. Akbar Ali, Dr. Hidayat M. Khan, Dr. M. Athar Abbasi, Mr. Touseef Ali Khan, Mr. Umair Quyyum Khan, Miss. Humera Zaheer, Miss. Rukhsana Kausor, Miss Husna Qamar, Miss. Fouzia Shamim, Ms. Zeenat Siddiqui, Muhammad Zubair, Afsar Khan, and Shazia Yasmeen to whom my sincere thanks are due. The whole book has been typed, composed, and structures drawn by Mr. Rafat Ali, Mr. Shabbir Ahmed, and Tariq Ilyas and I wish to express my sincere thanks to them."