Rice (Oryza sativa L.) is an important food crop providing energy and nutrients for more than half of the world population. It produces vast amounts of secondary metabolites. At least 276 secondary metabolites from rice have been identified in the past 50 years. They mainly include phenolic acids, flavonoids, terpenoids, steroids, alkaloids, and their derivatives. These metabolites exhibit many physiological functions, such as regulatory effects on rice growth and development, disease-resistance promotion, anti-insect activity, and allelopathic effects, as well as various kinds of biological activities such as antimicrobial, antioxidant, cytotoxic, and anti-inflammatory properties. This review focuses on our knowledge of the structures, biological functions and activities, biosynthesis, and metabolic regulation of rice secondary metabolites. Some considerations about cheminformatics, metabolomics, genetic transformation, production, and applications related to the secondary metabolites from rice are also discussed.

The 2,3-double bond reduction of the pyrenone ring in linear naphtho-γ-pyrenones was catalyzed by a phospholipid methyltransferase-like enzyme, namely UsgR, which is a previously unrecognised class of ene-reductases.

Five new chlamydosporol derivatives, named pleospyrones A-E (1–5), together with one known congener (6), were isolated from the culture of the endophytic fungus Pleosporales sp. Sigrf05, obtained from the medicinal plant Siraitia grosvenorii. The structures of the new compounds were elucidated mainly by analysis of the HRESIMS, and (1D, 2D) NMR data, while ECD and optical rotation calculations were used to assign the absolute configurations. The plausible biosynthetic pathway of these compounds were proposed. The isolated compounds were evaluated for their cytotoxicity, antifungal and antibacterial activities. Compounds 1, and 4–6 were cytotoxic against the tested cancer cells with IC50 values of 1.26~47.5 μM. Compounds 1–3 showed moderate antifungal activities against Magnaporthe oryzae, while compound 5 displayed weak antibacterial activity.

Ustilaginoidin M1 (1), a novel bis-naphtho-γ-pyrone, was isolated from the cultures of the fungus Villosiclava virens which was the pathogen of rice false smut disease. Its structure was elucidated by spectroscopic analysis and by comparison of its physical and spectroscopic data with the literature. Compound 1 was tested for its cytotoxicity against five human cancer cell lines.

Five chromone derivatives, including 2,6-dimethyl-5-methoxyl-7hydroxylchromone (1), 6-hydroxymethyleugenin (2), 6-methoxymethyleugenin (3), chaetoquadrin D (4), and isoeugenitol (5), and three isocoumarin congeners, namely diaporthin (6), 8-hydroxy-6-methoxy-3-methylisocoumarin (7), and 6-methoxymellein (8), were isolated from the culture of the endophytic fungus Xylomelasma sp. Samif07 derived from the medicinal plant Salvia miltiorrhiza Bunge.Among them, compound 1 was a new natural product. Their structures were determined by spectroscopic methods and comparison with the literature. The isolated compounds were evaluated for their antibacterial and antioxidant activities.Compound 5 showed notable antitubercular activity against Mycobacterium tuberculosis with MIC value of 10.31 µg/mL, while compounds 1-3, and 5-7displayed inhibitory activities against the other bacteria with MIC range of 25~100 µg/mL. Meanwhile, compound 6 showed potent hydroxyl radical-scavenging activity with EC 50 value of 15.1 µg/mL, while compounds 5-7 showed certain ferric reducing ability.