Phyllobilins from Senescence-Associated Chlorophyll Breakdown in the Leaves of Basil (Ocimum basilicum) Show Increased Abundance upon Herbivore Attack

[Image: see text] In view of the common use of the herb basil (Ocimum basilicum) in nutrition and in phytomedicine, the contents of its leaves are of obvious interest. In extracts of fresh yellowish-green basil leaves, phyllobilins (PBs), which are bilin-type catabolites of chlorophyll (Chl), were detected using high-performance liquid chromatography (HPLC). Two such PBs, provisionally named Ob-nonfluorescent chlorophyll catabolite (NCC)-40 and Ob-YCC-45, exhibited previously unknown structures that were delineated by a thorough spectroscopic characterization. When basil leaves were infested with aphids or thrips or underwent fungal infections, areas with chlorosis were observed. HPLC analyses of the infested parts of leaves compared to those of the healthy parts showed a significant accumulation of PBs in the infested areas, demonstrating that the senescence-associated pheophorbide a oxygenase/phyllobilin (PAO/PB) pathway is activated by herbivore feeding and fungal infection.