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Phylloxanthobilins are Abundant Linear Tetrapyrroles from Chlorophyll Breakdown with Activities Against Cancer Cells
Author(s) -
Karg Cornelia A.,
Wang Pengyu,
Kluibenschedl Florian,
Müller Thomas,
Allmendinger Lars,
Vollmar Angelika M.,
Moser Simone
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000692
Subject(s) - chemistry , cancer cell , pyrrole , apoptosis , chlorophyll , programmed cell death , double bond , alkyl , chlorophyll a , biochemistry , cell growth , cell , stereochemistry , cancer , organic chemistry , medicine
Linear tetrapyrroles, called phyllobilins, are obtained as major catabolites upon chlorophyll degradation. Primarily, colorless phylloleucobilins featuring four deconjugated pyrrole units were identified. Their yellow counterparts, phylloxanthobilins, were discovered more recently. Although the two catabolites differ only by one double bond, physicochemical properties are very distinct. Moreover, the presence of the double bond seems to enhance physiologically relevant bioactivities: in contrast to phylloleucobilin, we identified a potent anti‐proliferative activity for a phylloxanthobilin, and show that this natural product induces apoptotic cell death and a cell cycle arrest in cancer cells. Interestingly, upon modifying inactive phylloleucobilin by esterification, an anti‐proliferative activity can be observed that increases with the chain lengths of the alkyl esters. We provide first evidence for anti‐cancer activity of phyllobilins, report a novel plant source for a phylloxanthobilin, and by using paper spray MS, show that these bioactive yellow chlorophyll catabolites are more prevalent in Nature than previously assumed.