Clausanisumine, a Prenylated Bicarbazole Alkaloid from the Fruits of Clausena anisum-olens and Its Potential Anti-HIV Activity
Clausanisumine, a Prenylated Bicarbazole Alkaloid from the Fruits of Clausena anisum-olens and Its Potential Anti-HIV Activity
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DOI：
10.1021/acs.joc.1c02020
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发表时间：
2021-12-17
影响因子：
3.6
通讯作者：
Fu, Yan-Hui
中科院分区：
文献类型：
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作者：
Liu, Yan-Ping;Guo, Jia-Ming;Fu, Yan-Hui
从八角黄皮果实中分离得到一种独特的双咔唑生物碱，即黄皮酚(Clausanisumine)(1)和两个已知的生物起源相关单体咔唑生物碱(mukonal(2)和3-甲基咔唑(3))。黄皮酚(Clausanisumine，1)是一种罕见的双咔唑类生物碱，具有前所未有的碳骨架结构，由一个简单的咔唑生物碱和一个戊烯基咔唑生物碱组成。通过综合光谱方法确定了化合物1的化学结构。并提出了1，2，4-二甲基-4-甲基-4-甲基-4-酮的生物合成途径。此外，还对所有分离株1-3的体外抗HIV活性进行了评价。化合物1具有明显的抗HIV-1逆转录酶作用，其EC50值为18.58 nM。野苍耳中具有显著抗HIV活性的双咔唑生物碱的发现，将对发现和开发抗HIV新药具有重要意义。
A unique prenylated bicarbazole alkaloid, clausanisumine (1), and two biogenetically related known monomer carbazole alkaloids, mukonal (2) and 3-methylcarbazole (3), were isolated from the fruits of Clausena anisum-olens. Clausanisumine (1) was an uncommon prenylated bicarbazole alkaloid, possessing an unprecedented carbon skeleton, which was composed of a simple carbazole alkaloid and a prenylated carbazole alkaloid. The chemical structure of 1 was established by a combination of comprehensive spectral methods. A plausible biosynthetic pathway of 1 was also proposed. Additionally, the potential anti-HIV activities of all isolates 1-3 in vitro were evaluated. Compound 1 exhibited remarkable anti-HIV-1 reverse transcriptase effects showing an EC50 value of 18.58 nM. The discovery of the prenylated bicarbazole alkaloid from C. anisum-olens with notable anti-HIV activity would be meaningful to discovering and developing new anti-HIV drugs.