Kapusta Ireneusz, Janda Bogdan, Szajwaj Barbara, Stochmal Anna, Piacente Sonia, Pizza Cosimo, Franceschi Federico, Franz Chlodwig, Oleszek Wieslaw
Department of Biochemistry, Institute of Soil Science and Plant Cultivation, State Research Institute, ul. Czartoryskich 8, 24-100 Pulawy, Poland.
J Agric Food Chem. 2007 Oct 17;55(21):8485-90. doi: 10.1021/jf071709t. Epub 2007 Sep 15.
Horse chestnut extracts are widely used in pharmacy and cosmetic industries. The main active constituents are saponins of oleane type, but seeds of horse chestnut also contain flavonoids, being glycosides of quercetin and kaempferol. Their contribution to the overall activity of the extracts was not clear. In the present work, the main flavonoids from horse chestnut seeds were isolated and their structures established with spectral methods. Seven glycosides were isolated, out of which six ( 2, 3, 4, 7, 11, 13) were previously reported and one ( 9) was identified as a new tamarixetin 3- O- [beta- d-glucopyranosyl(1-->3)]- O-beta- d-xylopyranosyl-(1-->2)- O-beta- d-glucopyranoside. The structures of three additional compounds 1, 10, and 12, not previously reported, were deduced on the basis of their LC-ESI/MS/MS fragmentation characteristics. A new ultraperformance liquid chromatographic (UPLC) method has been developed for profiling and quantitation of horse chestnut flavonoids. The method allowed good separation over 4.5 min. Thirteen compounds could be identified in the profile, out of which di- and triglycoisdes of quercetin and kaempferol were the dominant forms and their acylated forms occurred in just trace amounts. The total concentration of flavonoids in the powdered horse chestnut seed was 0.88% of dry matter. The alcohol extract contained 3.46%, and after purification on C18 solid phase, this concentration increased to 9.40% of dry matter. The flavonoid profile and their content were also measured in the horse chestnut wastewater obtained as byproduct in industrial processing of horse chestnut seeds. The total flavonoid concentration in the powder obtained after evaporation of water was 2.58%, while after purification on solid phase, this increased to 11.23% dry matter. It was concluded that flavonoids are present in a horse chestnut extract in a relatively high amount and have the potential to contribute to the overall activity of these extracts. Industrial horse chestnut wastewater can be used to obtain quercetine and kaempferol glycosides for cosmetic, nutraceutical, and food supplement industries.
七叶树提取物广泛应用于制药和化妆品行业。其主要活性成分是齐墩果烷型皂苷，但七叶树种子还含有黄酮类化合物，即槲皮素和山柰酚的糖苷。它们对提取物整体活性的贡献尚不清楚。在本研究中，从七叶树种子中分离出主要黄酮类化合物，并用光谱方法确定了它们的结构。分离出七种糖苷，其中六种（2、3、4、7、11、13）先前已有报道，一种（9）被鉴定为新的柽柳素3 - O - [β - D - 吡喃葡萄糖基(1→3)] - O - β - D - 吡喃木糖基 - (1→2) - O - β - D - 吡喃葡萄糖苷。根据另外三种未报道的化合物1、10和12的液相色谱 - 电喷雾串联质谱（LC - ESI/MS/MS）裂解特征推断出其结构。已开发出一种新的超高效液相色谱（UPLC）方法用于七叶树黄酮类化合物的分析和定量。该方法在4.5分钟内实现了良好的分离。在色谱图中可鉴定出13种化合物，其中槲皮素和山柰酚的二糖苷和三糖苷是主要形式，其酰化形式仅微量存在。七叶树种子粉末中黄酮类化合物的总浓度为干物质的0.88%。醇提取物中含有3.46%，在C18固相上纯化后，该浓度增加到干物质的9.40%。还对七叶树种子工业加工过程中作为副产物获得的七叶树废水的黄酮类化合物谱及其含量进行了测定。水蒸发后得到的粉末中黄酮类化合物的总浓度为2.58%，而在固相上纯化后，该浓度增加到干物质的11.23%。得出的结论是，黄酮类化合物在七叶树提取物中的含量相对较高，并且有可能对这些提取物的整体活性做出贡献。工业七叶树废水可用于为化妆品、营养保健品和食品补充剂行业获取槲皮素和山柰酚糖苷。
