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New Acylated Phenolic Glycosides with ROS Scavenging Activity from Psidium guajava Leaves.

ROS and subsequent oxidative stress are reported to play important roles in chronic metabolic diseases. Plant-derived polyphenols, especially food-derived phenolics, have attracted a lot of attention due to their potential usage against oxidative stress-related diseases. The leaf of Psidium guajava (known as guava) is regarded as a good resource of polyphenols and its products are commercially available in Japan as functional foods against multiple chronic metabolism disorders. In the course of finding novel polyphenols with antioxidative activities from guava leaf, eleven acylated phenolic glycosides (1-11), including five new oleuropeic acid conjugated phenolic glycosides, named guajanosides A-E (1, 2, and 5-7), along with 17 known meroterpenoides (12-28) were isolated and identiﬁed. Their structures were determined by spectroscopic data analysis, chemical degradation and acid hydrolysis. Compounds 1, 2, and 5-11 displayed potent reactive oxygen species (ROS) scavenging activity in LPS-stimulated RAW 264.7 macrophage cells. Western blot revealed that compound 6 markedly increased the expression levels of nuclear factor-erythroid 2-related factor 2 (Nrf2), NAD(P)H quinone dehydrogenase 1 (NQO1) and glutamate-cysteine ligase catalytic subunit (GCLC). The current study revealed the presence of oleuropeic acid-derived phenolic glycosides in guava leaf, and highlighted the potential usage of this type of phenolics against oxidative stress-related metabolic diseases via activation of Nrf2 signaling pathway.