Laboratory of Bioregulation Chemistry

Rice Phytoalexins

Phytoalexins are low-molecular-weight antimicrobial substances that plants accumulate after pathogen attack. Phytoalexins look like fungicides that plants can make for themselves. Our laboratory has continued to study rice phytoalexins for more than 40 years and found extraordinary diversity of rice phytoalexins.

This page summarizes the information on rice phytoalexins.

このページの日本語版はこちら．

• Known Compounds Recognized as Rice Phytoalexins
• History of Rice Phytoalexin Research
• Publication List of Rice Phytoalexin-related Researches

What's New!

• 2023.05.11
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Tu, S. et al. De novo biosynthesis of sakuranetin from glucose by engineered Saccharomyces cerevisiae. Appl. Microbiol. Biotechnol. in press.
• 2023.05.05
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Kariya, K. et al. Natural variation of diterpenoid phytoalexins in rice: Aromatic diterpenoid phytoalexins in specific cultivars. Phytochemistry in press.
• 2023.04.27
  • The following papers were added to the Publication List of Rice Phytoalexin-related Researches.
    • Wang, L., Fu, J., Shen, Q., and Wang, Q. OsWRKY10 extensively activates multiple rice diterpenoid phytoalexin biosynthesis to enhance rice blast resistance. Plant J. in press.
    • da Cruz Ramos Pires, G.H. et al. (2022). Sakuranetin interacting with cell membranes models: Surface chemistry combined with molecular simulation. Colloids Surf., B 216: 112546.
• 2023.04.06
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Pires, G.H.D.C.R., Barbosa, H., Almeida, R.B.P., Lago, J.H.G., and Caseli, L. (2023). Ethanolamine phospholipids at the air-water interface as cell membranes models of microorganisms to study the nanotoxicology of sakuranetin. Thin Solid Films 770: 139768.
• 2023.04.05
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Smit, S.J., and Lichman, B.R. (2022). Plant biosynthetic gene clusters in the context of metabolic evolution. Nat. Prod. Rep. 39: 1465–1482.
• 2023.03.29
  • The following papers were added to the Publication List of Rice Phytoalexin-related Researches.
    • Wang, L. et al. (2023). The OsBDR1-MPK3 module negatively regulates blast resistance by suppressing the jasmonate signaling and terpenoid biosynthesis pathway. Proc. Natl. Acad. Sci. U. S. A. 120: e2211102120.
    • Kato-Noguchi, H. (2023). Defensive molecules momilactones A and B: function, biosynthesis, induction and occurrence. Toxins 15: 241.
• 2023.03.01
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Inagaki, H. et al. Genome editing reveals both the crucial role of OsCOI2 in jasmonate signaling and the functional diversity of COI1 homologs in rice. Plant Cell Physiol. in press.
• 2023.01.27
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Zhao, L., Oyagbenro, R., Feng, Y., Xu, M., and Peters, R.J. Oryzalexin S biosynthesis: a cross-stitched disappearing pathway. aBIOTECH in press.
• 2023.01.18
  • The following papers were added to the Publication List of Rice Phytoalexin-related Researches.
    • Rahaman, F. et al. (2022). Allelopathic potential in rice - a biochemical tool for plant defence against weeds. Front. Plant Sci. 13: 1072723.
    • Elhamouly, N.A. et al. (2022). The hidden power of secondary metabolites in plant-fungi interactions and sustainable phytoremediation. Front. Plant Sci. 13: 1044896.
• 2023.01.13
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Zhang, F. et al. (2020). Comparative proteomic analysis reveals novel insights into the interaction between rice and Xanthomonas oryzae pv. oryzae. BMC Plant Biol. 20: 563.
• 2023.01.11
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Sun, B. et al. OsGLP3-7 positively regulates rice immune response by activating hydrogen peroxide, jasmonic acid, and phytoalexin metabolic pathways. Mol. Plant Pathol. in press.
• 2023.01.06
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Valletta, A., Iozia, L.M., Fattorini, L., and Leonelli, F. (2023). Rice phytoalexins: half a century of amazing discoveries; part i: distribution, biosynthesis, chemical synthesis, and biological activities. Plants 12: 260.
• 2022.12.29
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Sánchez-Sanuy, F. et al. (2022). Iron induces resistance against the rice blast fungus Magnaporthe oryzae through potentiation of immune responses. Rice 15: 68.
• 2022.12.23
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Bernardo, L.R., and Braga, A.R.C. (2022). Sakuranetin state of the art: physical properties, biological effects, and biotechnological trends. Ind. Biotechnol. 18: 341–350.
• 2022.12.06
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Wang, Z., Nelson, D.R., Zhang, J., Wan, X., and Peters, R.J. Plant (di)terpenoid evolution: from pigments to hormones and beyond. Nat. Prod. Rep. in press.
• 2022.11.19
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Duda-Madej, A., Stecko, J., Sobieraj, J., Szymańska, N., and Kozłowska, J. (2022). Naringenin and its derivatives—health-promoting phytobiotic against resistant bacteria and fungi in humans. Antibiotics 11: 1628.
• 2022.10.26
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Anh, L.H. et al. (2022). Cytotoxic mechanism of momilactones A and B against acute promyelocytic leukemia and multiple myeloma cell lines. Cancers 14: 4848.
• 2022.09.30
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Vicente-Silva, W. et al. (2022). Sakuranetin exerts anticonvulsant effect in bicuculline-induced seizures. Fundam. Clin. Pharmacol. 36: 663–673.
• 2022.09.01
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Knoch, E. et al. (2022). Transcriptional response of a target plant to benzoxazinoid and diterpene allelochemicals highlights commonalities in detoxification. BMC Plant Biol. 22: 402.
• 2022.07.26
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Hoang Anh, L. et al. (2022). Rice momilactones and phenolics: expression of relevant biosynthetic genes in response to UV and chilling stresses. Agronomy 12: 1731.
• 2022.07.19
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Junaid, M. et al. Sakuranetin and its therapeutic potentials – a comprehensive review. Z. Naturforsch. C in press.
• 2022.07.07
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Wu, D. et al. Lateral transfers lead to the birth of momilactone biosynthetic gene clusters in grass. Plant J. in press.
• 2022.04.25
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Desmedt, W. et al. Rice diterpenoid phytoalexins are involved in defence against parasitic nematodes and shape rhizosphere nematode communities. New Phytol. in press.
• 2022.03.11
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Yang, J., Lai, J., Kong, W., and Li, S. Asymmetric synthesis of sakuranetin-relevant flavanones for the identification of new chiral antifungal leads. J. Agric. Food Chem. in press.
• 2022.03.03
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Fang, H. et al. Function of hydroxycinnamoyl transferases for the biosynthesis of phenolamides in rice resistance to Magnaporthe oryzae. J. Genet. Genomics in press.
• 2022.01.17
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Yan, N. et al. (2022). Chromosome-level genome assembly of Zizania latifolia provides insights into its seed shattering and phytocassane biosynthesis. Commun. Biol. 5: 36.
• 2021.12.11
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Koga, J. et al. (2021). Sphingadienine-1-phosphate levels are regulated by a novel glycoside hydrolase family 1 glucocerebrosidase widely distributed in seed plants. J. Biol. Chem. 297: 101236.
• 2021.11.26
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Shinya, T. et al. Chitooligosaccharide elicitor and oxylipins synergistically elevate phytoalexin production in rice. Plant Mol. Biol. in press.
• 2021.10.17
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Li, R., Zhang, J., Li, Z., Peters, R.J., and Yang, B. Dissecting the labdane-related diterpenoid biosynthetic gene clusters in rice reveals directional cross-cluster phytotoxicity. New Phytol. in press.
• 2021.08.06
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Komkleow, S., Niyomploy, P., and Sangvanich, P. (2021). Maldi-mass spectrometry imaging for phytoalexins detection in RD6 Thai rice. Appl. Biochem. Microbiol. 57: 533–541.
• 2021.07.14
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Itoh, A. et al. Functional kaurene-synthase-like diterpene synthases lacking a gamma domain are widely present in Oryza and related species. Biosci. Biotechnol. Biochem. in press.
• 2021.07.05
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Lu, J. et al. Identification of quantitative trait loci associated with resistance to Xanthomonas oryzae pv. oryzae pathotypes prevalent in South China. Crop J. in press.
• 2021.07.01
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Tomita, K. et al. Genome-wide screening of genes associated with momilactone B sensitivity in the fission yeast Schizosaccharomyces pombe. G3: Genes, Genomes, Genet. in press.
• 2021.06.20
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Inagaki, H. et al. (2021). Deciphering OPDA signaling components in the momilactone-producing moss Calohypnum plumiforme. Front. Plant Sci. 12: 987.
• 2021.06.16
  • The following papers were added to the Publication List of Rice Phytoalexin-related Researches.
    • Ninkuu, V. et al. (2021). Biochemistry of terpenes and recent advances in plant protection. Int. J. Mol. Sci. 22: 5710.
    • Ding, Y., Northen, T.R., Khalil, A., Huffaker, A., and Schmelz, E.A. (2021). Getting back to the grass roots: harnessing specialized metabolites for improved crop stress resilience. Curr. Opin. Biotechnol. 70: 174–186.
• 2021.06.01
  • The following papers were added to the Publication List of Rice Phytoalexin-related Researches.
    • Takii, T. et al. (1999). Serotonin derivative, N-(p-coumaroyl)serotonin, isolated from safflower (Carthamus tinctorius L.) oil cake augments the proliferation of normal human and mouse fibroblasts in synergy with basic fibroblast growth factor (bFGF) or epidermal growth factor (EGF)1. J. Biochem. 125: 910–915.
    • Zhang, H.L., Nagatsu, A., Watanabe, T., Sakakibara, J., and Okuyama, H. (1997). Antioxidative compounds isolated from safflower (Carthamus tinctorius L.) oil cake. Chem. Pharm. Bull. 45: 1910–1914.
    • Sakamura, S., Terayama, Y., Kawakatsu, S., Ichihara, A., and Saito, H. (1978). Conjugated serotonins related to cathartic activity in safflower seeds (Carthamus tinctorius L.). Agric. Biol. Chem. 42: 1805–1806.
    • Georgiev, L. et al. (2012). Radical scavenging and antimicrobial activities of cinnamoyl amides of biogenic monoamines. Riv. Ital. Sostanze Grasse 89: 91–102.
• 2021.05.17
  • The following papers were added to the Publication List of Rice Phytoalexin-related Researches.
    • Hifnawy, M.S., Vaquette, J., Sévenet, T., Pousset, J.-L., and Cavé, A. (1977). Produits neutres et alcaloides de Myrtopsis macrocarpa, M. myrtoidea, M. novae-caledoniae et M. sellingii. Phytochemistry 16: 1035–1039.
    • Yang, D. et al. Transcriptome analysis of rice response to blast fungus identified core genes involved in immunity. Plant Cell Environ. in press.
    • Xu, Y., Cheng, H.-F., Kong, C.-H., and Meiners, S.J. Intraspecific kin recognition contributes to interspecific allelopathy: A case study of allelopathic rice interference with paddy weeds. Plant Cell Environ. in press.
• 2021.05.15
  • The following papers were added to the Publication List of Rice Phytoalexin-related Researches.
    • Will, W. (1885). Ueber das Naringin. Ber. Dtsch. Chem. Ges. 18: 1311–1325.
    • Will, W. (1887). Ueber das Naringin. Ber. Dtsch. Chem. Ges. 20: 294–304.
    • Sonn, A. (1913). Die Konstitution des Naringenins. Phloroglucin-ester von Phenol-carbonsäuren. Ber. Dtsch. Chem. Ges. 46: 4050–4059.
    • 朝比奈泰彦, 篠田淳三, 犬伏元太郎 (1928). フラバノングルコシードに就て. 藥學雜誌 48: 207–214.
    • Asahina, Y., and Inubuse, M. (1928). Über die Konstitution des Naringenins (II. Mitteilung über die Flavanon-Glucoside). Ber. Dtsch. Chem. Ges. 61: 1514–1516.
• 2021.05.13
  • The following paper was added to the Publication List of Rice Phytoalexin-related Researches.
    • Xu, J. et al. (2021). Molecular dissection of rice phytohormone signaling involved in resistance to a piercing-sucking herbivore. New Phytol. 230: 1639–1652.
• 2021.05.12
  • The following papers were added to the Publication List of Rice Phytoalexin-related Researches.
    • Shen, S. et al. An Oryza-specific hydroxycinnamoyl tyramine gene cluster contributes to enhanced disease resistance. Sci. Bull. in press.
    • Vo, K.T.X. et al. (2021). Proteomics and metabolomics studies on the biotic stress responses of rice: an update. Rice 14: 30.
• 2021.05.08
  • Published this English page.