Tokyo University of Pharmacy and Life Sciences , Hachioji , Tokyo 192-0392 , Japan.
School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences , Kanazawa University , Kanazawa , 920-1192 , Japan.
J Nat Prod. 2019 Oct 25;82(10):2852-2858. doi: 10.1021/acs.jnatprod.9b00596. Epub 2019 Sep 24.
The isolation of 12 secondary metabolites, including seven new acetophenone monomers, from the 50% CHOH/CHCl extract (N089419-L/6) of was reported previously. In the present work, three new prenylated acetophenone dimers (-) and five known dimers (-) were isolated, and their structures were elucidated by using various NMR spectroscopic techniques and HRMS. Among the new dimers, an unprecedented 4-isobutyl-3-isopropyltetrahydro-2-pyran ring was observed in the structure of . This study is the first to report the formation of a 2-pyran ring between two prenylated acetophloroglucinols. Only four related dimers have been reported before, and they were formylated phloroglucinol dimers from the family Eucalypteae. Compounds and are acrovestone-like dimers, and the structure of was confirmed by total synthesis. The evaluation of the antiproliferative activity of isolated and synthesized acrovestone-like dimers indicated that a double bond in the prenyl-like moiety as found in the more active compounds might be important for mediating activity, while the pendant isobutyl group seems to be less important.
先前曾报道从 50%CHO/CHCl 提取物（N089419-L/6）中分离出 12 种次生代谢产物，包括 7 种新的苯乙酮单体。在本工作中，分离得到了 3 种新的香叶基化苯乙酮二聚体（-）和 5 种已知的二聚体（-），并通过各种 NMR 波谱技术和 HRMS 确定了它们的结构。在新的二聚体中，在 的结构中观察到了前所未有的 4-异丁基-3-异丙基四氢-2-吡喃环。这是首次报道两个香叶基化苯丙素酚之间形成 2-吡喃环。以前只报道过四个相关的二聚体，它们是来自桃金娘科的甲酰化苯丙素二聚体。化合物 和 是阿克罗维酮样二聚体，其结构通过全合成得到证实。对分离和合成的阿克罗维酮样二聚体的抗增殖活性评估表明，在活性更高的化合物中发现的类香叶基部分的双键可能对介导活性很重要，而侧链异丁基似乎不太重要。
