School of Pharmaceutical Sciences of Ribeirão Preto, University of São Paulo, Av. do Café, Ribeirão Preto, 14040-930, Brazil.
National Center for Natural Products Research, School of Pharmacy, University of Mississippi, Mississippi, 38677, USA.
Chem Biodivers. 2021 Sep;18(9):e2100288. doi: 10.1002/cbdv.202100288. Epub 2021 Jul 20.
Seven phenolic compounds (ferulic acid, caffeic acid, 4-methoxycinnamic acid, 3,4-dimethoxycinnamic acid, 3-hydroxy-4-methoxybenzaldehyde, 3-methoxy-4-hydroxypropiophenone and 1-O,2-O-digalloyl-6-O-trans-p-coumaroyl-β-D-glucopyranoside), a flavanonol (7-O-methylaromadendrin), two lignans (pinoresinol and matairesinol) and six diterpenic acids/alcohol (19-acetoxy-13-hydroxyabda-8(17),14-diene, totarol, 7-oxodehydroabietic acid, dehydroabietic acid, communic acid and isopimaric acid) were isolated from the hydroalcoholic extract of a Brazilian Brown Propolis and characterized by NMR spectral data analysis. The volatile fraction of brown propolis was characterized by CG-MS, composed mainly of monoterpenes and sesquiterpenes, being the major α-pinene (18.4 %) and β-pinene (10.3 %). This propolis chemical profile indicates that Pinus spp., Eucalyptus spp. and Araucaria angustifolia might be its primary plants source. The brown propolis displayed significant activity against Plasmodium falciparum D6 and W2 strains with IC of 5.3 and 9.7 μg/mL, respectively. The volatile fraction was also active with IC of 22.5 and 41.8 μg/mL, respectively. Among the compounds, 1-O,2-O-digalloyl-6-O-trans-p-coumaroyl-β-D-glucopyranoside showed IC of 3.1 and 1.0 μg/mL against D6 and W2 strains, respectively, while communic acid showed an IC of 4.0 μg/mL against W2 strain. Cytotoxicity was determined on four tumor cell lines (SK-MEL, KB, BT-549, and SK-OV-3) and two normal renal cell lines (LLC-PK1 and VERO). Matairesinol, 7-O-methylaromadendrin, and isopimaric acid showed an IC range of 1.8-0.78 μg/mL, 7.3-100 μg/mL, and 17-18 μg/mL, respectively, against the tumor cell lines but they were not cytotoxic against normal cell lines. The crude extract of brown propolis displayed antimicrobial activity against C. neoformans, methicillin-resistant Staphylococcus aureus, and P. aeruginosa at 29.9 μg/mL, 178.9 μg/mL, and 160.7 μg/mL, respectively. The volatile fraction inhibited the growth of C. neoformans at 53.0 μg/mL. The compounds 3-hydroxy-4-methoxybenzaldehyde, 3-methoxy-4-hydroxypropiophenone and 7-oxodehydroabietic acid were active against C. neoformans, and caffeic and communic acids were active against methicillin-resistant Staphylococcus aureus.
从巴西棕蜂胶的水醇提取物中分离得到了 7 种酚类化合物（阿魏酸、咖啡酸、4-甲氧基肉桂酸、3,4-二甲氧基肉桂酸、3-羟基-4-甲氧基苯甲醛、3-甲氧基-4-羟基肉桂基丙酮和 1-O,2-O-二没食子酰基-6-O-反式对香豆酰基-β-D-吡喃葡萄糖苷）、1 种黄烷酮醇（7-O-甲基莪达醇）、2 种木脂素（松脂醇和新松脂醇）和 6 种二萜酸/醇（19-乙酰氧基-13-羟基 abda-8(17),14-二烯、松脂醇、7-氧代去氢松香酸、去氢松香酸、环麻酸和异枞酸），并通过 NMR 光谱数据分析进行了鉴定。棕蜂胶的挥发性成分通过 CG-MS 进行了表征，主要由单萜和倍半萜组成，其中主要成分是 α-蒎烯（18.4%）和 β-蒎烯（10.3%）。该蜂胶的化学成分表明，松树、桉树和南洋杉可能是其主要的植物来源。棕蜂胶对恶性疟原虫 D6 和 W2 株的 IC 分别为 5.3 和 9.7μg/mL，表现出显著的抗疟原虫活性。挥发性成分的 IC 分别为 22.5 和 41.8μg/mL，也具有活性。在这些化合物中，1-O,2-O-二没食子酰基-6-O-反式对香豆酰基-β-D-吡喃葡萄糖苷对 D6 和 W2 株的 IC 分别为 3.1 和 1.0μg/mL，而环麻酸对 W2 株的 IC 为 4.0μg/mL。在 4 种肿瘤细胞系（SK-MEL、KB、BT-549 和 SK-OV-3）和 2 种正常肾细胞系（LLC-PK1 和 VERO）上测定了细胞毒性。Matairesinol、7-O-甲基莪达醇和异枞酸对肿瘤细胞系的 IC 范围分别为 1.8-0.78μg/mL、7.3-100μg/mL 和 17-18μg/mL，但对正常细胞系没有细胞毒性。棕蜂胶粗提取物对新型隐球菌、耐甲氧西林金黄色葡萄球菌和铜绿假单胞菌的 MIC 分别为 29.9μg/mL、178.9μg/mL 和 160.7μg/mL，挥发性成分对新型隐球菌的生长抑制作用为 53.0μg/mL。3-羟基-4-甲氧基苯甲醛、3-甲氧基-4-羟基肉桂基丙酮和 7-氧代去氢松香酸对新型隐球菌具有活性，咖啡酸和环麻酸对耐甲氧西林金黄色葡萄球菌具有活性。
