el Sayed K A, Halim A F, Zaghloul A M, McChesney J D, Stone M P, Voehler M, Hayashi K
Pharmacognosy Department, Faculty of Pharmacy, Mansoura University, Egypt.
Phytochemistry. 1995 May;39(2):395-403. doi: 10.1016/0031-9422(94)00858-q.
Eleven new pregnane ester glycosides have been isolated from the aerial parts of Stapelia variegata. Eight of the recognized compounds were established to possess the same trioside moiety, viz. 3-O-[3-O-methyl-6-deoxy-beta-D-allopyranosyl-(1-4)-beta-D- cymaropyranosyl-(1-4)-beta-D-cymaropyranoside]. These compounds were identified as: stavaroside A: 12-O-beta-angeloyl-20-O-benzoyl sarcostin; stavaroside B: 12-O-beta-angeloyl-20-O-tigloyl sarcostin; stavaroside C: 11 alpha-acetoxy 2 beta-benzoxy-3 beta,8 beta, 14 beta-trihydroxy-pregn-5-ene-20-one; stavaroside D: 11 alpha-acetoxy- 12 beta-tigloxy-3 beta,8 beta,14 beta-trihydroxy-pregn-5-ene-20-one; stavaroside E: 12-O-beta-benzoyl sarcostin; stavaroside F: 11 alpha-acetoxy-12 beta-acetoxy-3 beta,8 beta,14 beta-trihydroxy-pregn-5- ene-20-one; stavaroside G: 12-O-beta,20-O-diacetyl sarcostin and stavaroside H: 3 beta, 8 beta, 11 alpha, 12 beta, 14 beta-pentahydroxy-pregn-5- ene-20-one. The other three compounds were shown to possess the same tetraside sugar moiety, viz. 3-O-[beta-D-glucopyranosyl- (1-4)-3-O-methyl-6-deoxy-beta-D-allopyranosyl-(1-4)-beta-D-cymaropyra nosyl- (1-4)-beta-D-cymaropyranoside]. These compounds were identified as: stavaroside I: 1 alpha, 12 beta-angeloxy and benzoxy-3 beta,8 beta,14 beta-trihydroxy- pregn-5-ene-20-one; stavaroside J: 11 alpha-acetoxy-12 beta-benzoxy-3 beta, 8 beta,14 beta-trihydroxy-pregn-5-ene-20-one and stavaroside K: 11 alpha-acetoxy-12 beta-tigloxy-3 beta,8 beta,14 beta-trihydroxy-pregn-5-ene- 20-one. The structural elucidation of the isolated compounds was aided significantly on the basis of the chemical and spectral evidence. The decisive assignments of the ester positions were based on the Inverse Detected-Heteronuclear Multiple Bond Connectivity (HMBC) experiments.
从豹皮花的地上部分分离出了11种新的孕甾酯糖苷。已确定其中8种公认的化合物具有相同的三糖苷部分，即3 - O - [3 - O - 甲基 - 6 - 脱氧 - β - D - 阿洛吡喃糖基 - (1→4) - β - D - 磁麻糖基 - (1→4) - β - D - 磁麻糖苷]。这些化合物被鉴定为：斯塔瓦罗苷A：12 - O - β - 当归酰基 - 20 - O - 苯甲酰基肉珊瑚苷元；斯塔瓦罗苷B：12 - O - β - 当归酰基 - 20 - O - 惕各酰基肉珊瑚苷元；斯塔瓦罗苷C：11α - 乙酰氧基 - 2β - 苯甲氧基 - 3β,8β,14β - 三羟基 - 孕 - 5 - 烯 - 20 - 酮；斯塔瓦罗苷D：11α - 乙酰氧基 - 12β - 惕各氧基 - 3β,8β,14β - 三羟基 - 孕 - 5 - 烯 - 20 - 酮；斯塔瓦罗苷E：12 - O - β - 苯甲酰基肉珊瑚苷元；斯塔瓦罗苷F：11α - 乙酰氧基 - 12β - 乙酰氧基 - 3β,8β,14β - 三羟基 - 孕 - 5 - 烯 - 20 - 酮；斯塔瓦罗苷G：12 - O - β,20 - O - 二乙酰基肉珊瑚苷元；斯塔瓦罗苷H：3β,8β,11α,12β,14β - 五羟基 - 孕 - 5 - 烯 - 20 - 酮。另外三种化合物被证明具有相同的四糖苷糖部分，即3 - O - [β - D - 吡喃葡萄糖基 - (1→4) - 3 - O - 甲基 - 6 - 脱氧 - β - D -阿洛吡喃糖基 - (1→4) - β - D - 磁麻糖基 - (1→4) - β - D - 磁麻糖苷]。这些化合物被鉴定为：斯塔瓦罗苷I：1α,12β - 当归氧基和苯甲氧基 - 3β,8β,14β - 三羟基 - 孕 - 5 - 烯 - 20 - 酮；斯塔瓦罗苷J：11α - 乙酰氧基 - 1十二β - 苯甲氧基 - 3β,8β,14β - 三羟基 - 孕 - 5 - 烯 - 20 - 酮；斯塔瓦罗苷K：11α - 乙酰氧基 - 12β - 惕各氧基 - 3β,8β,14β - 三羟基 - 孕 - 5 - 烯 - 20 - 酮。基于化学和光谱证据，对分离出的化合物的结构解析有很大帮助。酯位置的决定性归属基于反向检测 - 异核多键连接(HMBC)实验。
