State Key Laboratory of Microbial Metabolism, and Engineering Research Center of Cell & Therapeutic Antibody, Ministry of Education, School of Pharmacy, Shanghai Jiao Tong University, Shanghai, 200240, China.
State Key Laboratory of Bioreactor Engineering, R&D Center of Separation and Extraction Technology in Fermentation Industry, East China University of Science and Technology, Shanghai, 200237, China.
Appl Microbiol Biotechnol. 2022 Jan;106(2):469-484. doi: 10.1007/s00253-021-11729-6. Epub 2021 Dec 18.
Azaphilone, biosynthesized by polyketide synthase, is a class of fungal metabolites. In this review, after brief introduction of the natural azaphilone diversity, we in detail discussed azaphilic addition reaction involving conversion of natural azaphilone into the corresponding azaphilone alkaloid. Then, setting red Monascus pigments (a traditional food colorant in China) as example, we presented a new strategy, i.e., interfacing azaphilic addition reaction with living microbial metabolism in a one-pot process, to produce azaphilone alkaloid with a specified amine residue (red Monascus pigments) during submerged culture. Benefit from the red Monascus pigments with a specified amine residue, the influence of primary amine on characteristics of the food colorant was highlighted. Finally, the progress for screening of alternative azaphilone alkaloids (production from interfacing azaphilic addition reaction with submerged culture of Talaromyces sp. or Penicillium sp.) as natural food colorant was reviewed. KEY POINTS: • Azaphilic addition reaction of natural azaphilone is biocompatible • Red Monascus pigment is a classic example of azaphilone alkaloids • Azaphilone alkaloids are alterative natural food colorant.
氮杂菲酮是一类由聚酮合酶生物合成的真菌代谢产物。在本篇综述中,在简要介绍天然氮杂菲酮的多样性之后,我们详细讨论了涉及将天然氮杂菲酮转化为相应氮杂菲酮生物碱的氮杂亲核加成反应。然后,以红色红曲色素(中国传统的食用色素)为例,我们提出了一种新策略,即在一锅法中使氮杂亲核加成反应与微生物的活体代谢相连接,在深层发酵过程中产生具有特定胺残基(红色红曲色素)的氮杂菲酮生物碱。得益于具有特定胺残基的红色红曲色素,突出了伯胺对食用色素特性的影响。最后,综述了筛选替代氮杂菲酮生物碱(通过氮杂亲核加成反应与土曲霉或青霉的深层发酵相连接生产)作为天然食用色素的进展。关键点:•天然氮杂菲酮的氮杂亲核加成反应具有生物相容性;•红色红曲色素是氮杂菲酮生物碱的经典实例;•氮杂菲酮生物碱是替代的天然食用色素。