Department of Applied Biology, School of Life Sciences, University of Hull, HU6 7RX, Hull, UK.
Planta. 1990 Aug;182(1):81-8. doi: 10.1007/BF00239988.
Arachidonic acid, cellulase, CuSO4, a sonicate of Phytophthora infestans mycelium and a spore suspension of Penicillium chrysogenum all elicited the formation of the sesquiterpenoid phytoalexins lubimin, 3-hydroxylubimin and rishitin in fruit cavities of Datura stramonium. 3-Hydroxylubimin was the predominant phytoalexin formed after treatment of the fruits with arachidonic acid, cellulase and the P. infestans preparation. Copper sulphate was a potent elicitor of lubimin but not 3-hydroxylubimin. The fungus P. chrysogenum metabolized lubimin and 3-hydroxylubimin to 15-dihydrolubimin and 3-hydroxy-15-dihydrolubimin respectively, both in fruit cavities inoculated with spores of this fungus and in pure culture. The 15-dihydrolubimin formed in the fruits by the fungus was further metabolized (by the fruits) to both isolubimin and 3-hydroxy-15-dihydrolubimin. The precursor-product relationships between all of the subject compounds was investigated by feeding experiments with (3)H-labelled compounds. 2-Dehydro-[15-(3)H1]lubimin was rapidly and efficiently incorporated into lubimin and may be the direct precursor of lubimin in planta. 3-Hydroxy[2-(3)H1]lubimin was incorporated into the nor-eudesmane rishitin but 10-epi-3-hydroxy[2-(3)H1]lubimin was not. An updated scheme for the biosynthesis and metabolism of lubimin and related compounds in infected tissues of solanaceous plants is presented.
花生四烯酸、纤维素酶、CuSO4、Phytophthora infestans 菌丝体的超声处理物和Penicillium chrysogenum 的孢子悬浮液都能诱导茄属植物果实腔中倍半萜类植物抗毒素lubimin、3-羟基-lubimin 和 rishitin 的形成。用花生四烯酸、纤维素酶和 P. infestans 制剂处理果实后，形成的主要植物抗毒素是 3-羟基-lubimin。硫酸铜是 lubimin 的有效诱导剂，但不是 3-羟基-lubimin。真菌 P. chrysogenum 将 lubimin 和 3-羟基-lubimin 代谢为 15-二氢-lubimin 和 3-羟基-15-二氢-lubimin，分别在接种这种真菌孢子的果实中和纯培养中。真菌在果实中形成的 15-二氢-lubimin 进一步被代谢（由果实）为 isolubimin 和 3-羟基-15-二氢-lubimin。通过用（3）H 标记的化合物进行饲喂实验，研究了所有研究化合物之间的前体-产物关系。2-脱氢-[15-（3）H1]lubimin 被迅速有效地掺入 lubimin 中，可能是植物中 lubimin 的直接前体。3-羟基-[2-（3）H1]lubimin 被掺入 nor-eudesmane rishitin 中，但 10-epi-3-羟基-[2-（3）H1]lubimin 没有。提出了一个更新的方案，用于感染茄科植物组织中 lubimin 和相关化合物的生物合成和代谢。
