Phylloxanthobilins are abundant linear tetrapyrroles from chlorophyll breakdown with activities against cancer cells

Karg CA, Wang P, Kluibenschedl F, Müller T, Allmendinger L, Vollmar AM, Moser S. 2020. Phylloxanthobilins are abundant linear tetrapyrroles from chlorophyll breakdown with activities against cancer cells. European Journal of Organic Chemistry. 2020(29), 4499–4509.

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Author
Karg, Cornelia A.; Wang, Pengyu; Kluibenschedl, FlorianISTA; Müller, Thomas; Allmendinger, Lars; Vollmar, Angelika M.; Moser, Simone
Abstract
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.
Publishing Year
Date Published
2020-08-09
Journal Title
European Journal of Organic Chemistry
Volume
2020
Issue
29
Page
4499-4509
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Karg CA, Wang P, Kluibenschedl F, et al. Phylloxanthobilins are abundant linear tetrapyrroles from chlorophyll breakdown with activities against cancer cells. European Journal of Organic Chemistry. 2020;2020(29):4499-4509. doi:10.1002/ejoc.202000692
Karg, C. A., Wang, P., Kluibenschedl, F., Müller, T., Allmendinger, L., Vollmar, A. M., & Moser, S. (2020). Phylloxanthobilins are abundant linear tetrapyrroles from chlorophyll breakdown with activities against cancer cells. European Journal of Organic Chemistry. Wiley. https://doi.org/10.1002/ejoc.202000692
Karg, Cornelia A., Pengyu Wang, Florian Kluibenschedl, Thomas Müller, Lars Allmendinger, Angelika M. Vollmar, and Simone Moser. “Phylloxanthobilins Are Abundant Linear Tetrapyrroles from Chlorophyll Breakdown with Activities against Cancer Cells.” European Journal of Organic Chemistry. Wiley, 2020. https://doi.org/10.1002/ejoc.202000692.
C. A. Karg et al., “Phylloxanthobilins are abundant linear tetrapyrroles from chlorophyll breakdown with activities against cancer cells,” European Journal of Organic Chemistry, vol. 2020, no. 29. Wiley, pp. 4499–4509, 2020.
Karg CA, Wang P, Kluibenschedl F, Müller T, Allmendinger L, Vollmar AM, Moser S. 2020. Phylloxanthobilins are abundant linear tetrapyrroles from chlorophyll breakdown with activities against cancer cells. European Journal of Organic Chemistry. 2020(29), 4499–4509.
Karg, Cornelia A., et al. “Phylloxanthobilins Are Abundant Linear Tetrapyrroles from Chlorophyll Breakdown with Activities against Cancer Cells.” European Journal of Organic Chemistry, vol. 2020, no. 29, Wiley, 2020, pp. 4499–509, doi:10.1002/ejoc.202000692.
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