instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Campus Diadema, Brazil.
Pharm Biol. 2012 Oct;50(10):1248-53. doi: 10.3109/13880209.2012.666880. Epub 2012 Aug 8.
In folk medicine, Schinus terebinthifolius Raddi (Anacardiaceae), has been used as a remedy for ulcers, respiratory problems, wounds, rheumatism, gout, diarrhea, skin ailments and arthritis, as well as to treat tumors and leprosy.
To investigate the chemical composition and cytotoxicity of essential oil from leaves of S. terebinthifolius as well as the identification of active compounds from this oil.
Essential oil from S. terebinthifolius leaves, obtained by hydrodistillation using a Clevenger-type apparatus, was characterized in terms of its chemical composition. Also, the crude oil was subjected to chromatographic separation procedures to afford an active fraction composed of α- and β-pinenes. These compounds, including hydrogenation (pinane) and epoxydation (α-pinene oxide) derivatives from α-pinene, were tested in vitro against murine melanoma cell line (B16F10-Nex2) and human melanoma (A2058), breast adenocarcinoma (MCF7), leukemia (human leukemia (HL-60) and cervical carcinoma (HeLa) cell lines.
Forty-nine constituents were identified in the oil (97.9% of the total), with germacrene D (23.7%), bicyclogermacrene (15.0%), β-pinene (9.1%) and β-longipinene (8.1%) as the main compounds. The crude essential oil showed cytotoxic effects in several cell lines, mainly on leukemia and human cervical carcinoma. Fractions composed mainly of α- and β-pinenes as well as those composed of individually pinenes showed effective activities against all tested cell lines. Aiming to determinate preliminary structure/activity relationships, α-pinene was subjected to epoxydation and hydrogenation procedures whose obtained α-pinene oxide showed an expressive depression in its cytotoxicity effect, similar as observed to pinane derivative.
The obtained results indicated that the monoterpenes α- and β-pinenes could be responsible to the cytotoxic activity detected in the crude oil from leaves of S. terebinthifolius. In addition, it was possibly inferred that the presence of double bond in their structures, mainly at endocyclic position, is crucial to cytotoxic potential detected in these derivatives.
在民间医学中，斯奇诺树（漆树科）的叶子被用作治疗溃疡、呼吸道问题、伤口、风湿、痛风、腹泻、皮肤病和关节炎的药物，也用于治疗肿瘤和麻风病。
研究斯奇诺树叶子精油的化学成分和细胞毒性，并鉴定这种油中的活性化合物。
采用克利夫兰型设备通过水蒸馏获得斯奇诺树叶子的精油，从化学成分方面对其进行了描述。此外，粗油经过色谱分离程序，得到由α-和β-蒎烯组成的活性馏分。这些化合物，包括α-蒎烯的氢化（蒎烷）和环氧化（α-蒎烯氧化物）衍生物，在体外对鼠黑色素瘤细胞系（B16F10-Nex2）和人黑色素瘤（A2058）、乳腺腺癌（MCF7）、白血病（人白血病（HL-60）和宫颈癌（HeLa）细胞系进行了测试。
油中鉴定出 49 种成分（占总量的 97.9%），其中主要化合物为大根香叶烯 D（23.7%）、双环大根香叶烯（15.0%）、β-蒎烯（9.1%）和β-长叶蒎烯（8.1%）。粗精油对几种细胞系表现出细胞毒性作用，主要对白血病和人宫颈癌有效。主要由α-和β-蒎烯组成的馏分以及单独由蒎烯组成的馏分对所有测试的细胞系均表现出有效活性。为了确定初步的结构/活性关系，对α-蒎烯进行了环氧化和氢化处理，得到的α-蒎烯氧化物的细胞毒性作用明显降低，类似于观察到的蒎烷衍生物。
研究结果表明，单萜类化合物α-和β-蒎烯可能是导致斯奇诺树叶子粗油中检测到的细胞毒性的原因。此外，可能推断出它们结构中环内双键的存在，特别是在中环位置，对这些衍生物中检测到的细胞毒性潜力至关重要。
