Schmidt TJ, Schmidt HM, Müller E, Peters W, Fronczek FR, Truesdale A, Fischer NH
Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany, and Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803.
J Nat Prod. 1998 Feb 27;61(2):230-6. doi: 10.1021/np970434g.
In continuation of our phytochemical investigation of Illicium floridanum Ellis (American star anise, star bush), three new sesquiterpene lactones possessing the anisatin-type carbon skeleton (8,9-seco-prezizaane skeleton), 14-acetoxy-3-oxofloridanolide (1), 13-acetoxy-14-(n-butyryloxy)floridanolide (2), and 3beta-acetoxy-14-n-butyryloxy-10-deoxyfloridanolide (3), were isolated from fruits of this plant. Their structures were elucidated by 1D and 2D NMR measurements. The molecular structure of 1 was obtained by single crystal X-ray diffraction. The 11,3-delta-lactone structure of the compound previously described as debenzoyldunnianin in our previous communication, on grounds of NMR spectral evidence and X-ray crystallographic analysis is revised to a delta-lactone closed between C-11 and C-7 (compound 4). The neurotoxic sesquiterpene lactone anisatin (5) and its isomer 2alpha-hydroxyneoanisatin (3-deoxy-2alpha-hydroxyanisatin, 6) were also isolated and identified by spectroscopic means. The presence of the neurotoxin 5 in relatively high amounts in the fruits and leaves confirms and explains early reports on the toxicity of this plant.
在对佛罗里达八角（美洲八角、八角树）进行植物化学研究的过程中，我们从该植物的果实中分离出了三种具有茴香毒素型碳骨架（8,9-裂-前紫穗槐烷骨架）的新倍半萜内酯，即14-乙酰氧基-3-氧代佛罗里达内酯（1）、13-乙酰氧基-14-（正丁酰氧基）佛罗里达内酯（2）和3β-乙酰氧基-14-正丁酰氧基-10-脱氧佛罗里达内酯（3）。通过一维和二维核磁共振测量确定了它们的结构。化合物1的分子结构通过单晶X射线衍射获得。根据核磁共振光谱证据和X射线晶体学分析，我们之前通讯中描述为去苯甲酰基邓宁宁的化合物的11,3-δ-内酯结构被修正为C-11和C-7之间形成的δ-内酯（化合物4）。神经毒性倍半萜内酯茴香毒素（5）及其异构体2α-羟基新茴香毒素（3-脱氧-2α-羟基茴香毒素，6）也通过光谱手段进行了分离和鉴定。果实和叶片中相对大量存在神经毒素5，这证实并解释了关于该植物毒性的早期报道。
