Department of Chemistry, Federal University of Amazonas (UFAM), Manaus 69080-900, AM, Brazil.
Postgraduate Program in Chemistry, Federal University of Amazonas (UFAM), Manaus 69080-900, AM, Brazil.
Molecules. 2024 Aug 13;29(16):3834. doi: 10.3390/molecules29163834.
R.E. Fries is an Amazonian species known as 'envira-bobó' and 'envira-fofa' and is common in the states of Amazonas, Acre, and Pará. Recently, the essential oil from the leaves of this species has shown promising antitumor activity both in vitro and in vivo. The presence of isoquinoline-derived alkaloids, including aporphinoids and tetrahydroprotoberberine alkaloids, has also been previously reported. In our ongoing search for bioactive compounds from Annonaceae Amazonian plants, the bark of was investigated via classical chromatography techniques, which revealed nine compounds, eight isoquinoline-derived alkaloids, a rare alkaloid with a -gem-dimethyltetradehydrocularine structure known as gouregine, seven known aporphinoid alkaloids: isopiline, -methylisopiline, melosmine, 9-hydroxyiguattescine, dihydromelosmine, lysicamine, and guattouregidine, and one known pimaradiene diterpene: acanthoic acid. All the isolated compounds were described for the first time in the bark of and their structures were elucidated by extensive analyses of their 1D and 2D NMR spectra in combination with MS data. The NMR data of the alkaloids isopiline, -methylisopiline, melosmine, dihydromelosmine, and guattouregidine were revised due to incomplete data in the literature and some ambiguities. The in vitro cytotoxic activities of the isolated compounds were evaluated against human cancer (HepG2, KG-1a, and HCT116) and noncancerous (MRC-5) cell lines via the Alamar blue assay after 72 h of incubation. Among the compounds evaluated against human cancer cell lines, the most active was the oxoaporphine alkaloid lysicamine, which has strong activity against HCT116 cells, with an IC value of 6.64 µg/mL (22.79 µmol/L). Melosmine had a moderate effect on HCT116 cells, with an IC value of 16.77 µg/mL (49.70 µmol/L), whereas acanthoic acid had moderate effects on HepG2 and HCT116 cells, with IC values of 14.63 µg/mL (48.37 µmol/L) and 21.25 µg/mL (70.25 µmol/L), respectively.
R.E. Fries 是一种被称为“envira-bobó”和“envira-fofa”的亚马逊物种，常见于亚马逊、阿克里和帕拉州。最近，这种植物的叶子精油在体外和体内都表现出有希望的抗肿瘤活性。先前也报道了含有异喹啉衍生生物碱的存在，包括阿朴啡类和四氢原小檗碱类生物碱。在我们正在进行的从亚马逊安诺拉植物中寻找生物活性化合物的研究中，通过经典的色谱技术对 进行了研究，揭示了 9 种化合物，其中 8 种是异喹啉衍生的生物碱，一种罕见的具有 -gem-二甲基十四氢环辛烷结构的生物碱，称为钩藤碱，7 种已知的阿朴啡类生物碱：异波尔定、- 甲基异波尔定、麦罗辛、9-羟基伊卡特辛、二氢麦罗辛、赖氨酸和瓜托雷吉丁，以及一种已知的贝壳杉二萜酸：刺桐酸。所有分离出的化合物均首次在 树皮中被描述，并通过其 1D 和 2D NMR 光谱与 MS 数据的广泛分析来阐明其结构。由于文献中数据不完整和存在一些歧义，对异波尔定、- 甲基异波尔定、麦罗辛、二氢麦罗辛和瓜托雷吉丁的生物碱的 NMR 数据进行了修订。在 72 小时孵育后，通过 Alamar 蓝测定法评估分离化合物对人癌细胞（HepG2、KG-1a 和 HCT116）和非癌细胞（MRC-5）的体外细胞毒性活性。在所评估的对人癌细胞系有活性的化合物中，最活跃的是氧化阿朴啡类生物碱赖氨酸，对 HCT116 细胞具有很强的活性，IC 值为 6.64 µg/mL（22.79 µmol/L）。麦罗辛对 HCT116 细胞有中度作用，IC 值为 16.77 µg/mL（49.70 µmol/L），而刺桐酸对 HepG2 和 HCT116 细胞有中度作用，IC 值分别为 14.63 µg/mL（48.37 µmol/L）和 21.25 µg/mL（70.25 µmol/L）。
