Synthetic approaches to access acortatarins, shensongines and pollenopyrroside; potent antioxidative spiro-alkaloids with a naturally rare morpholine moiety

Pyrrole spiroketal alkaloids (PSAs) are a class of novel natural products that have been recently disclosed. Acortatarin A and acortatarin B, two potent antioxidative spiroalkaloids with a naturally rare morpholine moiety, are important members of this class. These spiroalkaloids are isolated from A...

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Bibliographic Details
Published in:Fitoterapia 2018-09, Vol.129, p.366-382
Main Authors: Faisal, Muhammad, Shahzad, Danish, Larik, Fayaz Ali, Dar, Parsa
Format: Article
Language:English
Subjects:
Acortatarin
Capparisine
Pollenopyrroside
Pyrrole spiroketal alkaloids
Shensongine
Xylapyrroside
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Summary:Pyrrole spiroketal alkaloids (PSAs) are a class of novel natural products that have been recently disclosed. Acortatarin A and acortatarin B, two potent antioxidative spiroalkaloids with a naturally rare morpholine moiety, are important members of this class. These spiroalkaloids are isolated from Acorus tatarinowii, Brassica campestris, Capparis spinose, bread crust, Xylaria nigripes and medicine Shensong Yangxin and could inhibit significantly the reactive oxygen species (ROS) production in high-glucose-induced mesangial cells in a time- and dose-dependent manner. Hence, these natural products are promising starting points for the formation of new therapeutics to medicate cardiovascular diseases, cancer, diabetic complications, and other diseases in which ROS are implicated. The impressive structure combined with an interesting pharmacological activity prompted synthetic chemists to construct an asymmetric synthetic strategy that could be used to access structural derivatives in addition to the larger quantities of natural products required for further biological investigations. This review summarizes the current state of the literature regarding with the synthesis of acortatarin A and B and its other family members viz. shensongine A, B and C, and pollenopyrroside A. The present review discusses the pros and cons of synthetic methodologies, which would be beneficial for further developments in the synthetic methodologies. Hopefully, this struggle pushes the reader's mind to consider new perspectives, think differently and forge new connections. [Display omitted]
ISSN:0367-326X
DOI:10.1016/j.fitote.2018.03.014