HAPALINDOLES, ANTIBACTERIAL AND ANTIMYCOTIC ALKALOIDS FROM THE CYANOPHYTE HAPALOSIPHON-FONTINALIS
HAPALINDOLES, ANTIBACTERIAL AND ANTIMYCOTIC ALKALOIDS FROM THE CYANOPHYTE HAPALOSIPHON-FONTINALIS
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DOI：
10.1021/jo00382a012
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发表时间：
1987-03-20
影响因子：
3.6
通讯作者：
DEETER, JB
中科院分区：
文献类型：
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作者：
MOORE, RE;CHEUK, C;DEETER, JB
从培养的蓝藻 Hapalosiphon fontinalis 中分离出 18 种新的吲哚生物碱，hapalindoles C-Q 和 T-V。使用光谱方法测定了这 18 种次要乙酰吲哚的总体结构和相对立体化学。通过X射线晶体学确定了哈帕吲哚A、D和K的相对立体化学，并确定了哈帕吲哚K的绝对构型为11R、12R、13R。假设所有生物碱都具有与 K 相同的绝对立体化学，迄今为止分离的所有 hapalindol 都是 11R，所有含氯生物碱都是 13R。除哈帕吲哚 L 外，所有哈帕吲哚均为 12R。蓝绿藻中的主要生物碱 Hapalindoles A 和 B，以及一些次要的 hapalindoles 为 10R、15S。然而，一些生物碱，即。 C-G和U，分别是10S，15S和两个，即。 H和Q分别为10R、15R。大多数哈帕吲哚是四环的，但C-F和Q是三环的；然而，迄今为止分离出的三环哈帕吲哚都不是10R，15S。 Hapalindole T 是一种不寻常的硫代氨基甲酸盐，hapalindole V 是 10-羟基hapalindole G。
Eighteen new indole alkaloids, hapalindoles C-Q and T-V, have been isolated from the cultured cyanophyte Hapalosiphon fontinalis. The gross structures and relative stereochemistries of these 18 minor hepalindoles have been determined by using spectral methods. The relative stereochemistries of hapalindoles A, D, and K have been confirmed and the absolute configuration of hapalindole K has been established as 11R,12R,13R by X-ray crystallography. Assuming that all of the alkaloids have the same absolute stereochemistry as K, all of the hapalindoles isolated to date are 11R and all of the chlorine-containing ones are 13R. With the exception of hapalindole L, all of the hapalindoles are 12R. Hapalindoles A and B, the major alkaloids in the blue-green alga, and several of the minor hapalindoles are 10R,15S. Some of the alkaloids, however, viz. C-G and U, are 10S,15S and two, viz. H and Q, are 10R,15R. Most of the hapalindoles are tetracyclic, but C-F and Q are tricyclic; none of the tricyclic hapalindoles isolated to date, however, are 10R,15S. Hapalindole T is an unusual thiocarbamate and hapalindole V is 10-hydroxyhapalindole G.