New manzamine alkaloids with activity against infectious and tropical parasitic diseases from an indonesian sponge
New manzamine alkaloids with activity against infectious and tropical parasitic diseases from an indonesian sponge
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DOI：
10.1021/np020592u
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发表时间：
2003-06-01
影响因子：
5.1
通讯作者：
Hamann, MT
中科院分区：
文献类型：
--
作者：
Rao, KV;Santarsiero, BD;Hamann, MT
从印度尼西亚海绵中分离出十一种曼扎明型生物碱、两种β-咔啉和五种核苷。其中包括先前表征的 12,34-oxamanzamine A、12,34-oxamanzamine E、manzamine A (1)、8-羟基manzamine A、6-脱氧manzamine X、manzamine E (2)、manzamine X、manzamine F (4)、norharman、胸腺嘧啶、2',3'-二脱氢-2',3'-二脱氧尿苷、尿嘧啶、胸苷和2'-脱氧尿苷。这五种新化合物的结构被指定为 32,33-二氢-31-羟基曼扎明 A (3)、32,33-二氢-6-羟基曼扎明 A-35-一 (5)、des-N-甲基xestomanzamine A (6)、32,33-二氢-6,31-二羟基曼扎明 A (7) 和1,2,3,4-四氢去甲哈满-1-酮 (8)，基于 NMR 和 X 射线数据。还介绍了曼扎明对抗疟疾、结核病和利什曼原虫的生物活性和比吸收率。还讨论了先前报道的两种吡唑（尿嘧啶和胸腺嘧啶）的结构修正。
Eleven manzamine type alkaloids, two beta-carbolines, and five nucleosides have been isolated from an Indonesian sponge. Among these are the previously characterized 12,34-oxamanzamine A, 12,34-oxamanzamine E, manzamine A (1), 8-hydroxymanzamine A, 6-deoxymanzamine X, manzamine E (2), manzamine X, manzamine F (4), norharman, thymine, 2',3'-didehydro-2',3'-dideoxyuridine, uracil, thymidine, and 2'-deoxyuridine. The structures for the five new compounds have been assigned as 32,33-dihydro-31-hydroxymanzamine A (3), 32,33-dihydro-6-hydroxymanzamine A-35-one (5), des-N-methylxestomanzamine A (6), 32,33-dihydro-6,31-dihydroxymanzamine A (7), and 1,2,3,4-tetrahydronorharman-1-one (8), on the basis of NMR and X-ray data. The bioactivity and SAR of the manzamines against malaria, TB, and leishmania are also presented. The structural revision of two previously reported pyrazoles as uracil and thymine is also discussed.