通过硝化制备3,9-二甲氧基黄碳(1,同黄碳)的衍生物,amination,和氧化反应,其中,并评估了它们对植物病原真菌炭疽菌和C.lindemuthianum的抗真菌活性。通过色谱技术纯化衍生物,并通过核磁共振光谱进行鉴定。从1中获得了八种衍生物,对应于3,9-二甲氧基-8-硝基果肉(2),3,9-二甲氧基-2,8-二硝基果肉(3),3,9-二甲氧基-2,8,10-三硝基果肉(4),2,8-二氨基-3,9-二甲氧蝶呤(5),3,9-二甲基coumestan(6),medicarpin(7),2'-羟基-4-(2-羟乙基硫基)-7,4'-二甲氧基异黄酮(8),和4-(2-羟乙基硫基)-7,2',4\'-三甲氧基异黄酮(9)。在35至704μM的浓度下测定衍生物的体外抗真菌活性。化合物7和8在704μM,显示对径向生长和孢子萌发的抑制接近100%,超过起始化合物1的46%。还对木瓜果实(CaricapapayaL.cv。夏威夷)和芒果(芒果。Hilacha)感染了C.gloeosporioides。化合物8在水果中显示的真菌生长抑制高于1和百里酚(公认的天然抗真菌药),在相同的条件下。总的来说,具有更强抗真菌活性的衍生物对应于结构中含有羟基的化合物。所获得的一些化合物可以被认为有希望用于控制植物病原性真菌。
Derivatives of 3,9-dimethoxypterocarpan (1, homopterocarpin) were prepared by nitration, amination, and oxidation reactions, among others, and their antifungal activity was evaluated against the phytopathogenic fungi Colletotrichum gloeosporioides and C. lindemuthianum. Derivatives were purified by chromatographic techniques and identified by nuclear magnetic resonance spectroscopy. Eight derivatives were obtained from 1 corresponding to 3,9-dimethoxy-8-nitropterocarpan (2), 3,9-dimethoxy-2,8-dinitropterocarpan (3), 3,9-dimethoxy-2,8,10-trinitropterocarpan (4), 2,8-diamino-3,9-dimethoxypterocarpan (5), 3,9-dimethylcoumestan (6), medicarpin (7), 2\'-hydroxy-4-(2-hydroxyethylsulfanyl)-7,4\'-dimethoxyisoflavan (8), and 4-(2-hydroxyethylsulfanyl)-7,2\',4\'-trimethoxyisoflavan (9). The in vitro antifungal activity of the derivatives was determined at concentrations between 35 and 704 μM. Compounds 7 and 8 at 704 μM, showed an inhibition of radial growth and spore germination close to 100%, exceeding that found for the starting compound 1, which was 46%. Growth inhibition assays were also performed for the derivative 8 on papaya fruits (Carica papaya L. cv. Hawaiana) and mango (Mangifera indica L. cv. Hilacha) infected with C. gloeosporioides. Compound 8 showed fungal growth inhibition in fruits higher than that found for 1 and thymol (a recognized natural antifungal), under the same conditions. In general, derivatives that exhibited greater antifungal activity correspond to the compounds containing hydroxyl groups in the structure. Some of the compounds obtained could be considered promising for the control of phytopathogenic fungi.