Lee Seungjin, Park In Guk, Choi Jin Won, Son Jin Young, Lee Jin Woo, Hur Jae-Seoun, Kim Youngmee, Nam Sang-Jip, Kang Hahk-Soo, Deyrup Stephen T, Noh Minsoo, Shim Sang Hee
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.
College of Pharmacy, Duksung Women's University, Seoul 01369, Republic of Korea.
Org Lett. 2023 Sep 15;25(36):6725-6729. doi: 10.1021/acs.orglett.3c02583. Epub 2023 Aug 31.
Daldipyrenones A-C (-), three unprecedented caged xanthone [6,6,6,6,6] polyketides featuring a spiro-azaphilone unit, were discovered from an endolichenic fungus, 047188. The structures of - were determined by using spectroscopic analysis and chemical derivatization. Daldipyrenones are likely derived by combining a chromane biosynthesis intermediate, 1-(2,6-dihydroxyphenyl)but-2-en-2-one, and a spiro-azaphilone, pestafolide A, via radical coupling or Michael addition to form a bicyclo[2.2.2]octane ring. Genome sequencing of the strain revealed two separate biosynthetic gene clusters responsible for forming two biosynthetic intermediates, suggesting a proposed biosynthetic pathway. Daldipyrenone A () exhibited significant antimelanogenic activity with lower EC's than positive controls and moderate adiponectin-secretion promoting activity.
从一种内生地衣真菌047188中发现了A - C（-）型双二吡喃酮，这是三种前所未有的带有螺氮杂蒽酮单元的笼状呫吨酮[6,6,6,6,6]聚酮化合物。通过光谱分析和化学衍生化确定了其结构。双二吡喃酮可能是由一个色烷生物合成中间体1 -（2,6 - 二羟基苯基）丁 - 2 - 烯 - 2 - 酮和一个螺氮杂蒽酮即佩斯塔福利德A，通过自由基偶联或迈克尔加成形成双环[2.2.2]辛烷环而衍生得到。该菌株的基因组测序揭示了两个独立的生物合成基因簇，负责形成两种生物合成中间体，提示了一条推测的生物合成途径。双二吡喃酮A（）表现出显著的抗黑色素生成活性，其半数有效浓度低于阳性对照，并具有适度的促进脂联素分泌的活性。
