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7.1′,8.3′- and 7.3′,8.5′-Connected Bicyclo[3.2.1]octanoids and Oxabicyclo[3.2.2]nonane-Type Neolignans from Ocotea aciphylla: Structures and Absolute Configurations
Journal of Natural Products ( IF 3.3 ) Pub Date : 2024-02-23 , DOI: 10.1021/acs.jnatprod.3c01013 Carlos Henrique Totini Dos Santos 1 , Edith Eunice Arthur Petrica 1 , Andrea Nastri de Luca Batista 2 , Edilene Delphino Rodrigues 1 , Walmir Silva Garcez 1 , Ana Carolina Ferreira de Albuquerque 2 , Fernando Martins Dos Santos 2 , João Marcos Batista 3 , Fernanda Rodrigues Garcez 1
Journal of Natural Products ( IF 3.3 ) Pub Date : 2024-02-23 , DOI: 10.1021/acs.jnatprod.3c01013 Carlos Henrique Totini Dos Santos 1 , Edith Eunice Arthur Petrica 1 , Andrea Nastri de Luca Batista 2 , Edilene Delphino Rodrigues 1 , Walmir Silva Garcez 1 , Ana Carolina Ferreira de Albuquerque 2 , Fernando Martins Dos Santos 2 , João Marcos Batista 3 , Fernanda Rodrigues Garcez 1
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The phytochemical investigation of the leaves and trunk bark of a specimen of Ocotea aciphylla collected in the southern portion of the Amazon forest led to the isolation of an oxabicyclo[3.2.2]nonane-type neolignan and 15 bicyclo[3.2.1]octanoid neolignans, 14 of which are unreported compounds (2–15), including one with an unusual oxidation pattern of the side chain at C-1′ and two rare 7.1′,8.3′-connected bicyclo[3.2.1]octanoid derivatives. Their structures and relative configurations were determined by extensive spectrometric analysis based on 1D- and 2D-NMR spectroscopy and HRESIMS data, while their absolute configurations were unambiguously assigned using electronic and vibrational circular dichroism data assisted by density functional theory calculations. Additionally, known sesquiterpenes, phenylpropanoids, and phytosterols were also isolated.
中文翻译：
来自 Ocotea aciphylla 的 7.1',8.3'- 和 7.3',8.5'- 连接的双环[3.2.1]辛烷类化合物和氧杂双环[3.2.2]壬烷型新木脂素：结构和绝对构型
对亚马逊森林南部采集的Ocotea aciphylla标本的叶子和树干树皮进行植物化学研究，分离出一种氧双环[3.2.2]壬烷型新木脂素和 15 种双环[3.2.1]辛烷类新木脂素，其中 14 种是未报道的化合物 ( 2 – 15 )，包括一种在 C-1' 侧链具有不寻常氧化模式的化合物和两种罕见的 7.1',8.3' 连接的双环[3.2.1]辛烷衍生物。它们的结构和相对构型是通过基于一维和二维核磁共振光谱和 HRESIMS 数据的广泛光谱分析确定的，而它们的绝对构型是使用密度泛函理论计算辅助的电子和振动圆二色性数据明确指定的。此外，还分离出了已知的倍半萜、苯丙素和植物甾醇。
更新日期：2024-02-23
中文翻译：
来自 Ocotea aciphylla 的 7.1',8.3'- 和 7.3',8.5'- 连接的双环[3.2.1]辛烷类化合物和氧杂双环[3.2.2]壬烷型新木脂素：结构和绝对构型
对亚马逊森林南部采集的Ocotea aciphylla标本的叶子和树干树皮进行植物化学研究，分离出一种氧双环[3.2.2]壬烷型新木脂素和 15 种双环[3.2.1]辛烷类新木脂素，其中 14 种是未报道的化合物 ( 2 – 15 )，包括一种在 C-1' 侧链具有不寻常氧化模式的化合物和两种罕见的 7.1',8.3' 连接的双环[3.2.1]辛烷衍生物。它们的结构和相对构型是通过基于一维和二维核磁共振光谱和 HRESIMS 数据的广泛光谱分析确定的，而它们的绝对构型是使用密度泛函理论计算辅助的电子和振动圆二色性数据明确指定的。此外，还分离出了已知的倍半萜、苯丙素和植物甾醇。
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