Populations of Primula auricula L. subsp. auricula from Austrian Alps were studied for flavonoid composition of both farinose exudates and tissue of leaves. The leaf exudate yielded Primula-type flavones, such as unsubstituted flavone and its derivatives, while tissue flavonoids largely consisted of flavonol 3-O-glycosides, based upon kaempferol (3, 4) and isorhamnetin (5–7). Kaempferol 3-O-(2″-O-β-xylopyranosyl-[6″-O-β-xylopyranosyl]-β-glucopyranoside) (3) and isorhamnetin 3-O-(2″-O-β-xylopyranosyl-[6″-O-β-xylopyranosyl]-β-glucopyranoside) (6) are newly reported as natural compounds. Remarkably, two Primula type flavones were also detected in tissues, namely 3′-hydroxyflavone 3′-O-β-glucoside (1) and 3′,4′-dihydroxyflavone 4′-O-β-glucoside (2), of which (1) is reported here for the first time as natural product. All structures were unambiguously identified by NMR and MS data. Earlier reports on the occurrence of 7,2′-dihydroxyflavone 7-O-glucoside (macrophylloside) in this species could not be confirmed. This structure was now shown to correspond to 3′,4′-dihydroxyflavone 4′-O-glucoside (2) by comparison of NMR data. Observed exudate variations might be specific for geographically separated populations. The structural diversification between tissue and exudate flavonoids is assumed to be indicative for different ecological roles in planta.

Primula auricula L. subsp. 的种群。研究了来自奥地利阿尔卑斯山的auricula 的粉糖渗出液和叶子组织的类黄酮成分。叶渗出物得到报春花型黄酮，例如未取代的黄酮和其衍生物，而组织黄酮很大程度上由的黄酮醇3- ø -glycosides，基于山萘酚（3，4）和异鼠李素（5 - 7）。山奈酚 3- O -(2″- O -β-吡喃木糖基-[6″- O -β-吡喃木糖基]-β-吡喃葡萄糖苷) ( 3 ) 和异鼠李素 3- O -(2″- O-β-吡喃木糖基-[6″ -O -β-吡喃木糖基]-β-吡喃葡萄糖苷) ( 6 ) 作为天然化合物新近报道。值得注意的是，组织中还检测到两种报春花型黄酮，即3'-羟基黄酮3'- O -β-葡萄糖苷（1）和3',4'-二羟基黄酮4'- O -β-葡萄糖苷（2），其中( 1 ) 这里首次报道为天然产物。所有结构均通过 NMR 和 MS 数据明确鉴定。早期关于该物种中 7,2'-二羟基黄酮 7- O-葡萄糖苷（macrophylloside）的报道无法得到证实。现在显示该结构对应于 3',4'-二羟基黄酮 4'-O-葡萄糖苷( 2 )通过核磁共振数据的比较。观察到的渗出液变化可能特定于地理上分离的人群。组织和渗出物类黄酮之间的结构多样化被假定为指示植物中不同的生态作用。