STRUCTURES OF MITORUBRIN AND MITRUBRINOL
STRUCTURES OF MITORUBRIN AND MITRUBRINOL
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DOI：
10.1021/ja01093a036
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发表时间：
1965-01-01
影响因子：
15
通讯作者：
WOGAN, GN
中科院分区：
文献类型：
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作者：
BUCHI, G;WHITE, JD;WOGAN, GN
霉菌和真菌代谢物的分离和表征通常受到微生物的一些显着特征的推动，例如其色素沉着或其制造有毒或治疗剂的能力。红色青霉因其菌丝体在生长过程中产生的颜色和合成高毒性物质的能力而闻名。后一个特征因被证明感染红色假单胞菌的饲料导致牲畜中毒而引起了人们的关注。 2· 3 在本工作过程中，我们发现导致真菌色素沉着的物质与引起毒性的物质不同，在本文中，我们将讨论两种色素的分离和结构测定。当红色 P. rubrum 生长在小麦或玉米等天然培养基上时，其菌丝体会呈现出亮橙色，其中散布着深红色斑点。生长2至3周后用乙酸乙酯提取培养物，得到深红色提取物，其除色素外还含有大量脂质和脂溶性物质。由于颜料相对难溶于非极性溶剂，因此可以通过用极性增加的溶剂萃取来浓缩它们。在用石油醚进行初始提取时，脂质物质被除去，根据薄层色谱，用乙醚提取后的最终残留物含有三种主要色素以及一些无色极性物质。该残留物在硅酸上进行色谱分离，得到两种纯色素，我们分别将其命名为米托红布林和米托红布诺。对已知霉菌产品的搜索仅公开了一种先前已分离和鉴定的红色假单胞菌代谢物。 4 这种物质，phoe-
The isolation and characterization of mold and fungal metabolites has generally been impelled by some conspicuous feature of the microorganism, such as its pigmentation or its ability to elaborate a toxic or therapeutic agent. Penicillium rubrum is notable both for the coloration which its mycelium develops during growth and for its ability to synthesize a substance of high toxicity. The latter feature has attracted atten-tion in association with the poisoning of livestock through feedstuff which was shown to be infected with P. rubrum. 2· 3 During the course of the present work it was found that the substances responsible for pigmentation of the fungus are distinct from the agent (s) causing toxicity and in the present paper we shall dis-cuss the isolation and structure determination of two pigments.When P. rubrum is grown on a natural medium such as wheat or corn its mycelium develops a brilliant orange coloration interspersed with flecks of darker red. Ex-traction of the culture with ethyl acetate after 2 to 3 weeks of growth affords a dark red extract which con-tains, in addition to pigments, a large amount of lipid and fat-soluble material. Since the pigments are relatively insoluble in nonpolar solvents, they can be concentrated by extracting with solvents of increasing polarity. The lipid material is removed in the initial extraction with petroleum etherand the final residue after extraction with ethyl ether contains, according to thin layer chromatography, three principal pigments together with some colorless, polar material. Chromatography of this residue on silicic acid yields two pure pigments which we have named mitorubrin and mitorubrinol, respectively. A search among the known mold products disclosed only one metabolite of P. rubrum which has been pre-viously isolated and identified. 4 This substance, phoe-