Cardanols detected in non-polar propolis extracts from Scaptotrigona aff. postica (Hymenoptera, Apidae, Meliponini)

Abstract The propolis produced by stingless bees of the tribe Meliponini is a viscous product that contains the resin collected from buds, leaves and plant exudates, mixed with salivary secretions, wax and soil. The species Scaptotrigona aff. postica (Latreille, 1807), (Hymenoptera, Apidae, Meliponinae) popularly known as “tubi” in Maranhão State, Brazil, does not mix soil to produce its propolis. The propolis from S. postica harvested in Barra do Corda, Maranhão State, is popularly used in the treatment of wounds and respiratory illnesses. The hydroalcoholic extract of this propolis, rich in flavone-6,8-di-C-glycosides (vicenin-2 and schaftoside), pyrrolizidine alkaloids derived from retronecine, catechin and caffeoylquinic acid derivatives exhibited antiviral activity against the herpes simplex and rubella viruses. The aim of this study was to increase knowledge about the chemical composition of the S. postica propolis by analyzing non-polar extracts obtained using hexane and chloroform as the solvents, by GC-EI-MS. A total of 15 constituents were identified comparing their respective mass spectral data with those available in the NIST data bases and those reported in the literature. The main constituents detected were the phenolic lipids, known as cardanols, 3-(4,7-heptadecadienyl) phenol (5), 3-(10-heptadecenyl) phenol (7), 3-heptadecylphenol (9) and 3-pentadecyl phenol or hydrocardanol (13), which predominated in the hexane extract, while the predominant constituents in the chloroform extract were 3-pentadecyl phenol or hydrocardanol (13) and 3-(8-pentadecenyl) phenol (12). The antioxidant, antitumoral, antifeedant, cytotoxic, anticarcinogenic, antiproliferative, antimicrobial, antileishmanial and larvicidal activities of the cardanols have been demonstrated in many studies.

摘要
无刺蜂族（Meliponini）所产的蜂胶（propolis）为粘性产物，其成分包含从芽、叶及植物分泌物中采集的树脂，并混合唾液分泌物、蜂蜡与土壤。本次研究的对象为近缘后斑无刺蜂（Scaptotrigona aff. postica，Latreille, 1807），隶属于膜翅目（Hymenoptera）蜜蜂科（Apidae）无刺蜂亚科（Meliponinae），在巴西马拉尼昂州当地俗称‘tubi’，该蜂生产蜂胶时并不混入土壤。在马拉尼昂州巴拉杜科尔达（Barra do Corda）采收的该种蜂胶，常被用于伤口与呼吸道疾病的治疗。
该蜂胶的水醇提取物富含黄酮-6,8-二-C-糖苷类（维塞宁-2（vicenin-2）与沙夫托苷（schaftoside））、源自倒千里光碱（retronecine）的吡咯里西啶生物碱（pyrrolizidine alkaloids）、儿茶素（catechin）及咖啡酰奎宁酸衍生物，对单纯疱疹病毒与风疹病毒展现出抗病毒活性。
本研究旨在通过以正己烷与三氯甲烷（氯仿，chloroform）为溶剂制备非极性提取物，并采用气相色谱-电子轰击质谱（GC-EI-MS）进行分析，以增进对后斑无刺蜂蜂胶化学成分的认知。通过将各组分的质谱数据与美国国家标准与技术研究院（NIST）数据库及文献报道的数据进行比对，本研究共鉴定出15种组分。
检测到的主要组分为被称为腰果酚（cardanols）的酚类脂类，包括3-(4,7-十七碳二烯基)苯酚(5)、3-(10-十七碳烯基)苯酚(7)、3-十七烷基苯酚(9)以及3-十五烷基苯酚或氢化腰果酚(13)，此类组分在正己烷提取物中占主导地位；而三氯甲烷提取物中的主要组分为3-十五烷基苯酚或氢化腰果酚(13)与3-(8-十五碳烯基)苯酚(12)。
多项研究已证实腰果酚具备抗氧化、抗肿瘤、拒食、细胞毒性、抗癌、抗增殖、抗菌、抗利什曼原虫及杀幼虫等多种生物活性。