Mulberry Diels–Alder-type adducts: isolation, structure, bioactivity, and synthesis

Abstract

Mulberry Diels–Alder-type adducts (MDAAs) are unique phenolic natural products biosynthetically derived from the intermolecular [4 + 2]-cycloaddition of dienophiles (mainly chalcones) and dehydroprenylphenol dienes, which are exclusively distributed in moraceous plants. A total of 166 MDAAs with diverse skeletons have been isolated and identified since 1980. Structurally, the classic MDAAs characterized by the chalcone-skeleton dienophiles can be divided into eight groups (Types A − H), while others with non-chalcone dienophiles or some variations of classic MDAAs are non-classic MDAAs (Type I). These compounds have attracted significant attention of natural products and synthetic chemists due to their complex architectures, remarkable biological activities, and synthetic challenges. The present review provides a comprehensive summary of the structural properties, bioactivities, and syntheses of MDAAs. Cited references were collected between 1980 and 2021 from the SciFinder, Web of Science, and China National Knowledge Internet (CNKI). Graphical Abstract

Synthesis, reactions and application of chalcones: a systematic review

“…Mulberry trees (Morus plants of the family Moraceae) are known for their naturally occurring phenolic compounds known as Mulberry Diels–Alder type adducts (MDAAs) 133 . 198 They are created biosynthetically through the intermolecular [4 + 2] cycloaddition of dienophiles (mostly chalcones) 129 and dehydroprenylphenol dienes 132 , as depicted in Scheme 45. Various Moraceae plant family mulberry Diels–Alder type adducts have been discovered.…”

Molecular networking-guided investigation of the secondary metabolome of four Morus species and their in vivo neuroprotective potential for the mitigation of Alzheimer's disease

“…8 Among the Morus species, M. alba was reported to target several proteins involved in AD pathogenesis. 6,9 Additionally, anthocyanins present in M. atropurpurea exhibited a protective AD effect. 10 Yet their therapeutic potential in comparison to other Morus species has not been satisfactorily explored.…”

A Mulberry Diels-Alder-Type Adduct, Kuwanon M, Triggers Apoptosis and Paraptosis of Lung Cancer Cells through Inducing Endoplasmic Reticulum Stress

“…The root bark of mulberry is known as “Sang-Bai-Pi” in Chinese medicine, and is considered to possess the function of treating cough, asthma, edema and oliguria [ 1 ]. Flavonoids, stilbenes, benzofurans and Mulberry Diels-Alder-type adducts (MDAAs) are the main constituents of the root bark of mulberry [ 2 ]. Among these, MDAAs are unique compounds with complicated structures which has made these compounds an attractive research topic in recent decades.…”