LYCORINE STRUCTURE ACTIVITY RELATIONSHIPS
LYCORINE STRUCTURE ACTIVITY RELATIONSHIPS
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DOI：
10.1016/s0031-9422(00)80145-4
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发表时间：
1983-01-01
期刊：
影响因子：
3.8
通讯作者：
ARRIGONI, O
中科院分区：
文献类型：
--
作者：
EVIDENTE, A;CICALA, MR;ARRIGONI, O
测试了 23 种石蒜碱衍生物和天然存在的生物碱，它们在结构上与石蒜碱 [从石蒜科的石蒜中分离] 抑制马铃薯块茎中抗坏血酸生物合成的能力。观察结构修饰和活性之间的关系。间二氧杂环戊烯环上缩醛键的断裂对活性没有影响。 C-8（A 环）上带有甲氧基的衍生物没有活性。 NCH2-7 氧化为酰胺基（B 环）导致活性丧失。当 D 环呈现 β 时，C/D 环连接处的修饰对活性没有影响。构型，而当该环呈现α时，观察到活性大大降低。配置。 C环羟基的选择性或完全乙酰化、C-2上羟基的差向异构化或氧化导致活性丧失。 1,2 位具有双键的化合物表现出与石蒜碱几乎相同的活性。 C环双键的立体选择性氢化导致活性显着增加。 N原子的质子化对活性没有影响。
Twenty-three lycorine derivatives and naturally occurring alkaloids, structurally related to lycorine [isolated from Sternbergia lutea, Amaryllidaceae] were tested for their ability to inhibit ascorbic acid biosynthesis in potato tubers. Relationships between structural modification and activity were observed. Cleavage of the acetalic bonds on the dioxole ring had no effect on activity. Derivatives with a methoxy group on C-8 (A ring) were inactive. Oxidation of NCH2-7 to an amide group (B ring) caused loss of activity. Modification of the C/D ring junction had no effect on activity when the D ring assumed a .beta. configuration whereas a great decrease of activity was observed when that ring assumed an .alpha. configuration. Selective or complete acetylation of hydroxyl groups of the C ring, epimerization or oxidation of the hydroxyl group on C-2 led to a loss of activity. A compound with a double bond located in the 1,2 position showed activity almost identical to lycorine. Stereoselective hydrogenation of the double bond of the C ring induced a considerable increase of the activity. Protonation of the N atom had no affect on activity.