ABSTRACT Colletotrichum lupini is the causal agent of lupin (Lupinus albus L.) anthracnose, a destructive seed-borne disease affecting stems and pods. Despite that several biological studies have been carried out on this pathogen, the production of secondary metabolites has not yet been investigated. Thus, a strain of C. lupini, obtained from symptomatic stems of L. albus, has been grown in vitro to evaluate its ability to produce bioactive compounds. From its culture filtrates, a 3-substituted indolinone, named lupindolinone, and a 5,6-disubstituted tetrahydro-α-pyrone, named lupinlactone, were isolated together with the known (3R)-mevalonolactone and tyrosol. Lupindolinone and lupinlactone were characterized as 3-ethylindolin-2-one and 5-hydroxy-6-methyltetrahydropyran-2-one by spectroscopic methods (essentially nuclear magnetic resonance [NMR] and high-resolution electrospray ionization mass spectrometry [HR ESI-MS]). The R absolute configuration (AC) at C-5 of lupinlactone was determined by applying the modified Mosher’s method. Thus, considering its relative stereochemistry assigned by NMR spectroscopy, the AC of lupinlactone could be formulated as 5R,6S. Lupindolinone was isolated as racemic mixture as shown by investigation using chiroptical methods. The metabolites were assayed in different biological tests and proved to have some activities at the used concentration.

中文翻译：

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羽扇豆炭疽病的致病因子Colletotrichum lupini 产生的次生代谢物（羽扇豆属）

摘要 羽扇豆炭疽病是羽扇豆 (Lupinus albus L.) 炭疽病的病原体，炭疽病是一种影响茎和豆荚的破坏性种子传播疾病。尽管已经对这种病原体进行了几项生物学研究，但尚未研究次级代谢物的产生。因此，已经在体外培养了一种从 L. albus 的有症状茎中获得的 C. lupini 菌株，以评估其产生生物活性化合物的能力。从其培养滤液中，分离出一种名为羽扇豆酮的 3-取代吲哚酮和一种名为羽扇豆内酯的 5,6-二取代四氢-α-吡喃酮，以及已知的 (3R)-甲羟戊内酯和酪醇。通过光谱方法（主要是核磁共振 [NMR] 和高分辨率电喷雾电离质谱 [HR ESI-MS]），羽扇豆酮和羽扇豆内酯被表征为 3-ethylindolin-2-one 和 5-hydroxy-6-methyltetrahydropyran-2-one ）。羽扇豆内酯 C-5 处的 R 绝对构型 (AC) 通过应用改进的 Mosher 方法确定。因此，考虑到其由 NMR 光谱指定的相对立体化学，羽扇豆内酯的 AC 可以表示为 5R,6S。羽扇豆酮被分离为外消旋混合物，如使用手性方法研究所示。代谢物在不同的生物试验中进行了测定，并证明在所用浓度下具有一些活性。羽扇豆内酯 C-5 处的 R 绝对构型 (AC) 通过应用改进的 Mosher 方法确定。因此，考虑到其由 NMR 光谱指定的相对立体化学，羽扇豆内酯的 AC 可以表示为 5R,6S。羽扇豆酮被分离为外消旋混合物，如使用手性方法研究所示。代谢物在不同的生物试验中进行了测定，并证明在所用浓度下具有一些活性。羽扇豆内酯 C-5 处的 R 绝对构型 (AC) 通过应用改进的 Mosher 方法确定。因此，考虑到其由 NMR 光谱指定的相对立体化学，羽扇豆内酯的 AC 可以表示为 5R,6S。羽扇豆酮被分离为外消旋混合物，如使用手性方法研究所示。代谢物在不同的生物试验中进行了测定，并证明在所用浓度下具有一些活性。