Oryzamutaic acids H–J, new alkaloids from an Oryza sativa mutant with yellow endosperm

Isolation and identification of oryzamutaic acids A and D from an Oryza sativa spontaneous mutant with yellow endosperm

“…2), had the molecular formula, C 17 H 25 N 3 O 4 , established by HRESIMS [m/z 334.1805 (M-H) − , Δ +4.4 mmu], which is the same as those of oryzamutaic acids D-G (Nakano et al 2010a). Oryzamutaic acids E-G had shorter retention times than oryzamutaic acid D. Among oryzamutaic acids present in the endosperm of Hatsuyamabuki, oryzamutaic acids A and D are the most prevalent (Nakano et al 2009(Nakano et al , 2010a(Nakano et al , 2010b. These results indicate that the brawn rice of Musashino 20, like that of Hatsuyamabuki, contained oryzamutaic acids A and D.…”

“…The rare rice cultivar Hatsuyamabuki, which has yellow endosperm, was selected from the progeny obtained by treatment of the rice cultivar Kinuhikari with γ-rays at the National Agricultural Research Center for Kyushu Okinawa Region (Kaji et al 2010). In previous study, we isolated oryzamutaic acids A-J, alkaloids with a novel nitrogencontaining heterocyclic ring system, from the yellow endosperm (polished rice) of Hatsuyamabuki (Nakano et al 2009(Nakano et al , 2010a(Nakano et al , 2010b. Oryzamutaic acids A-C are yellow, but oryzamutaic acids D-J are colorless.…”

Chemical Structure Diversity and Extensive Biological Functions of Specialized Metabolites in Rice

“…Thirty-five triterpenoids have been isolated and identified from rice, and are mainly found in rice bran [53][54][55][56][57][58][59][60][61][62][63][64][65][66]. The major types include citrostadienol (104)(105)(106)(107), gramisterol (108)(109)(110), cycloeucalenol (111)(112)(113), cycloartanol (114 and 115), tetracyclic triterpene (118)(119)(120), cycloartane (124)(125)(126)(127)(128), orizalanosterolide (130)(131), and lupane (132)(133) [53][54][55][56][57]61,[63][64][65]67,68]. Compounds 104-113 and their derivatives are considered to be nortriterpenoids according to their biosynthetic pathways.…”

“…Forty one alkaloids (373-413) have been identified from rice, including indolamides (373-380), amides (381-399, 403), and nitrogen-containing heterocyclic rings, formed by the decarboxylation of dicarboxylic acid (401 and 404-413) [82,[119][120][121][122][123][124][125][126][127][128][129][130][131][132][133]. 2-acetyl-1-pyrroline (381), a nitrogen-containing aromatic compound, is present at high concentrations in brown rice, and gives it its unique "popcorn" flavor [124].…”