New eudesmane derivatives from Melampodium camphoratum from the Suriname rainforest.

New eudesmane derivatives from Melampodium camphoratum from the Suriname rainforest.
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来自苏里南雨林的樟树的新桉树衍生物。

DOI:
10.1021/np049696q
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发表时间:
2004
期刊:
Journal of natural products.
影响因子:
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通讯作者:
Kingston,DavidGI
Kingston,DavidGI
中科院分区:
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文献类型:
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作者:
Chaturvedula,VSPrakash;Farooq,Afgan;Schilling,JenniferK;Malone,S;Derveld,Iwan;Werkhoven,MargaCM;Wisse,JanH;Ratsimbason,Michel;Kingston,DavidGI

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对樟脑叶的 EtOAc 提取物进行生物测定引导的分级分离,并进行氯高铁血红素降解抑制剂测定,结果分离出六种新的桉树倍半萜 (1−6) 和已知的 6-epi-β-马鞭醇香豆酸酯 (7)。化合物1−6的结构确定为6α-(4'-O-甲基-7'E-香豆芳氧基)eudesm-4(14)-ene (1)、6α-({4'-O-硬脂基}-7'E-香豆芳氧基)eudesm-4(14)-ene (2)、 6α-({4'-O-棕榈基}-7'E-香豆芳氧基)eudesm-4(14)-ene (3), 6α-({4'-O-[9' 'Z-十六烯酰基]}-7'E-香豆芳氧基)eudesm-4(14)-ene (4), 6α-(7'Z-香豆芳氧基)eudesm-4(14)-ene (5) 和 6α-({4'-乙酰氧基}-7'Z-香豆芳氧基)eudesm-4(14)-ene (6)。化合物 1−4 在氯高铁血红素降解测定中表现出弱活性,而化合物 5−7 则无活性。
Bioassay-guided fractionation of an EtOAc extract of the leaves ofMelampodium camphoratumusing an assay for inhibitors of the degradation of hemin resulted in the isolation of six new eudesmane sesquiterpenes (1−6) and the known 6-epi-β-verbesinol coumarate (7). The structures of compounds1−6were established as 6α-(4‘-O-methyl-7‘E-coumaryloxy)eudesm-4(14)-ene (1), 6α-({4‘-O-stearyl}-7‘E-coumaryloxy)eudesm-4(14)-ene (2), 6α-({4‘-O-palmityl}-7‘E-coumaryloxy)eudesm-4(14)-ene (3), 6α-({4‘-O-[9‘ ‘Z-hexadecenoyl]}-7‘E-coumaryloxy)eudesm-4(14)-ene (4), 6α-(7‘Z-coumaryloxy)eudesm-4(14)-ene (5), and 6α-({4‘-acetoxy}-7‘Z-coumaryloxy)eudesm-4(14)-ene (6). Compounds1−4showed weak activity in the hemin degradation assay, while compounds5−7were inactive.