Pathways Knowlegdes
Biological pathway database
| Pathway | DOIs | Note |
|---|---|---|
| volatile benzenoid biosynthesis I (ester formation) Accession ID: BioCyc:ARA_PWY-4203 |
|
Dudareva N, Pichersky E, Gershenzon J. Biochemistry of plant volatiles. Plant Physiol. 2004 Aug;135(4):1893–902. PMID: 15326281; PMCID: PMC520761.; Chen F, D'Auria JC, Tholl D, Ross JR, Gershenzon J, Noel JP, Pichersky E. An Arabidopsis thaliana gene for methylsalicylate biosynthesis, identified by a biochemical genomics approach, has a role in defense. The Plant Journal. 2003 Nov 18;36(5):577–88. doi: 10.1046/j.1365-313x.2003.01902.x.; Degenhardt J, Gershenzon J, Baldwin IT, Kessler A. Attracting friends to feast on foes: engineering terpene emission to make crop plants more attractive to herbivore enemies. Curr Opin Biotechnol. 2003 Apr;14(2):169–76. doi: 10.1016/s0958-1669(03)00025-9. PMID: 12732318.; D'Auria JC, Chen F, Pichersky E. Characterization of an acyltransferase capable of synthesizing benzylbenzoate and other volatile esters in flowers and damaged leaves of Clarkia breweri. Plant Physiol. 2002 Sep;130(1):466–76. PMID: 12226525; PMCID: PMC166578.; Dudareva N, Raguso RA, Wang J, Ross JR, Pichersky E. Floral scent production in Clarkia breweri. III. Enzymatic synthesis and emission of benzenoid esters. Plant Physiol. 1998 Feb;116(2):599–604. PMID: 9489012; PMCID: PMC35117. |
| genistin gentiobioside biosynthesis Accession ID: PlantCyc:CROSEUS_PWY-7145 |
|
Dong X, Xu W, Sikes RA, Wu C. Apoptotic effects of cooked and in vitro digested soy on human prostate cancer cells. Food Chem. 2012 Dec 01;135(3):1643–52. doi: 10.1016/j.foodchem.2012.06.023. PMID: 22953905.; Zou P, Xing L, Tang Q, Liu R, Hao W. Comparative evaluation of the teratogenicity of genistein and genistin using rat whole embryo culture and limbud micromass culture methods. Food Chem Toxicol. 2012 Aug;50(8):2831–6. doi: 10.1016/j.fct.2012.05.009. PMID: 22617716.; Jin SE, Son YK, Min B, Jung HA, Choi JS. Anti-inflammatory and antioxidant activities of constituents isolated from Pueraria lobata roots. Archives of Pharmacal Research. 2012 May 29;35(5):823–37. doi: 10.1007/s12272-012-0508-x.; Weng CJ, Yen GC. Flavonoids, a ubiquitous dietary phenolic subclass, exert extensive in vitro anti-invasive and in vivo anti-metastatic activities. Cancer Metastasis Rev. 2012 Jun;31(1-2):323–51. doi: 10.1007/s10555-012-9347-y. PMID: 22314287.; Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H. Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus. Plant Cell Physiol. 2009 Aug;50(8):1401–15. doi: 10.1093/pcp/pcp088. PMID: 19561332.; Hsieh MC, Graham TL. Partial purification and characterization of a soybean beta-glucosidase with high specific activity towards isoflavone conjugates. Phytochemistry. 2001 Dec;58(7):995–1005. doi: 10.1016/s0031-9422(01)00380-6. PMID: 11730862. |
| methylsalicylate biosynthesis Accession ID: PlantCyc:ARA_PWY18C3-22 |
- | |
| phytocassanes biosynthesis, shared reactions Accession ID: PlantCyc:ORYZA_PWY-7484 |
|
Wu Y, Wang Q, Hillwig ML, Peters RJ. Picking sides: distinct roles for CYP76M6 and CYP76M8 in rice oryzalexin biosynthesis. Biochem J. 2013 Sep 01;454(2):209–16. PMID: 23795884; PMCID: PMC3787970.; Wang Q, Hillwig ML, Okada K, Yamazaki K, Wu Y, Swaminathan S, Yamane H, Peters RJ. Characterization of CYP76M5–8 Indicates Metabolic Plasticity within a Plant Biosynthetic Gene Cluster. Journal of Biological Chemistry. 2012 Feb;287(9):6159–68. doi: 10.1074/jbc.m111.305599.; Wang Q, Hillwig ML, Wu Y, Peters RJ. CYP701A8: a rice ent-kaurene oxidase paralog diverted to more specialized diterpenoid metabolism. Plant Physiol. 2012 Mar;158(3):1418–25. PMID: 22247270; PMCID: PMC3291257.; Wu Y, Hillwig ML, Wang Q, Peters RJ. Parsing a multifunctional biosynthetic gene cluster from rice: Biochemical characterization of CYP71Z6 & 7. FEBS Lett. 2011 Nov 04;585(21):3446–51. PMID: 21985968; PMCID: PMC3227696.; Osbourn A. Gene clusters for secondary metabolic pathways: an emerging theme in plant biology. Plant Physiol. 2010 Oct;154(2):531–5. PMID: 20921179; PMCID: PMC2949040.; Swaminathan S, Morrone D, Wang Q, Fulton DB, Peters RJ. CYP76M7 is an ent-cassadiene C11alpha-hydroxylase defining a second multifunctional diterpenoid biosynthetic gene cluster in rice. Plant Cell. 2009 Oct;21(10):3315–25. PMID: 19825834; PMCID: PMC2782285.; Osbourn AE, Field B. Operons. Cellular and Molecular Life Sciences. 2009 Aug 07;66(23):3755–75. doi: 10.1007/s00018-009-0114-3.; Fischbach MA, Walsh CT, Clardy J. The evolution of gene collectives: How natural selection drives chemical innovation. Proc Natl Acad Sci U S A. 2008 Mar 25;105(12):4601–8. PMID: 18216259; PMCID: PMC2290807.; Okada A, Shimizu T, Okada K, Kuzuyama T, Koga J, Shibuya N, Nojiri H, Yamane H. Elicitor induced activation of the methylerythritol phosphate pathway toward phytoalexins biosynthesis in rice. Plant Mol Biol. 2007 Sep;65(1-2):177–87. doi: 10.1007/s11103-007-9207-2. PMID: 17634747.; Cyr A, Wilderman PR, Determan M, Peters RJ. A modular approach for facile biosynthesis of labdane-related diterpenes. J Am Chem Soc. 2007 May 30;129(21):6684–5. PMID: 17480080; PMCID: PMC2518946.; Xu M, Wilderman PR, Morrone D, Xu J, Roy A, Margis-Pinheiro M, Upadhyaya NM, Coates RM, Peters RJ. Functional characterization of the rice kaurene synthase-like gene family. Phytochemistry. 2007 Feb;68(3):312–26. doi: 10.1016/j.phytochem.2006.10.016. PMID: 17141283.; Peters RJ. Uncovering the complex metabolic network underlying diterpenoid phytoalexin biosynthesis in rice and other cereal crop plants. Phytochemistry. 2006 Nov;67(21):2307–17. doi: 10.1016/j.phytochem.2006.08.009. PMID: 16956633.; Prisic S, Xu M, Wilderman PR, Peters RJ. Rice contains two disparate ent-copalyl diphosphate synthases with distinct metabolic functions. Plant Physiol. 2004 Dec;136(4):4228–36. PMID: 15542489; PMCID: PMC535852.; Otomo K, Kenmoku H, Oikawa H, König WA, Toshima H, Mitsuhashi W, Yamane H, Sassa T, Toyomasu T. Biological functions of ent- and syn-copalyl diphosphate synthases in rice: key enzymes for the branch point of gibberellin and phytoalexin biosynthesis. The Plant Journal. 2004 Jul 30;39(6):886–93. doi: 10.1111/j.1365-313x.2004.02175.x. |
| genistin gentiobioside biosynthesis Accession ID: PlantCyc:PLANT_PWY-7145 |
|
Dong X, Xu W, Sikes RA, Wu C. Apoptotic effects of cooked and in vitro digested soy on human prostate cancer cells. Food Chem. 2012 Dec 01;135(3):1643–52. doi: 10.1016/j.foodchem.2012.06.023. PMID: 22953905.; Zou P, Xing L, Tang Q, Liu R, Hao W. Comparative evaluation of the teratogenicity of genistein and genistin using rat whole embryo culture and limbud micromass culture methods. Food Chem Toxicol. 2012 Aug;50(8):2831–6. doi: 10.1016/j.fct.2012.05.009. PMID: 22617716.; Jin SE, Son YK, Min B, Jung HA, Choi JS. Anti-inflammatory and antioxidant activities of constituents isolated from Pueraria lobata roots. Archives of Pharmacal Research. 2012 May 29;35(5):823–37. doi: 10.1007/s12272-012-0508-x.; Weng CJ, Yen GC. Flavonoids, a ubiquitous dietary phenolic subclass, exert extensive in vitro anti-invasive and in vivo anti-metastatic activities. Cancer Metastasis Rev. 2012 Jun;31(1-2):323–51. doi: 10.1007/s10555-012-9347-y. PMID: 22314287.; Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H. Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus. Plant Cell Physiol. 2009 Aug;50(8):1401–15. doi: 10.1093/pcp/pcp088. PMID: 19561332.; Hsieh MC, Graham TL. Partial purification and characterization of a soybean beta-glucosidase with high specific activity towards isoflavone conjugates. Phytochemistry. 2001 Dec;58(7):995–1005. doi: 10.1016/s0031-9422(01)00380-6. PMID: 11730862. |
| apigenin glycosides biosynthesis Accession ID: PlantCyc:CROSEUS_PWY-6010 |
|
Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H. Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus. Plant Cell Physiol. 2009 Aug;50(8):1401–15. doi: 10.1093/pcp/pcp088. PMID: 19561332. |
| myricetin gentiobioside biosynthesis Accession ID: PlantCyc:CROSEUS_PWY-7140 |
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Vepsäläinen S, Koivisto H, Pekkarinen E, Mäkinen P, Dobson G, McDougall GJ, Stewart D, Haapasalo A, Karjalainen RO, Tanila H, Hiltunen M. Anthocyanin-enriched bilberry and blackcurrant extracts modulate amyloid precursor protein processing and alleviate behavioral abnormalities in the APP/PS1 mouse model of Alzheimer's disease. The Journal of Nutritional Biochemistry. 2013 Jan;24(1):360–70. doi: 10.1016/j.jnutbio.2012.07.006.; Fiori J, Naldi M, Bartolini M, Andrisano V. Disclosure of a fundamental clue for the elucidation of the myricetin mechanism of action as amyloid aggregation inhibitor by mass spectrometry. Electrophoresis. 2012 Nov;33(22):3380–6. doi: 10.1002/elps.201200186. PMID: 22961751.; Chobot V, Hadacek F. Exploration of pro-oxidant and antioxidant activities of the flavonoid myricetin. Redox Report. 2011 Nov;16(6):242–7. doi: 10.1179/1351000211y.0000000015.; Kumar D, Kumar S, Gupta J, Arya R, Gupta A. A review on chemical and biological properties of Cayratia trifolia Linn. (Vitaceae). Pharmacogn Rev. 2011 Jul;5(10):184–8. PMID: 22279376; PMCID: PMC3263053.; Owens DK, McIntosh CA. Identification, recombinant expression, and biochemical characterization of a flavonol 3-O-glucosyltransferase clone from Citrus paradisi. Phytochemistry. 2009 Jul;70(11-12):1382–91. doi: 10.1016/j.phytochem.2009.07.027. PMID: 19733370.; Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H. Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus. Plant Cell Physiol. 2009 Aug;50(8):1401–15. doi: 10.1093/pcp/pcp088. PMID: 19561332.; Oguchi Y, Masada S, Kondo T, Terasaka K, Mizukami H. Purification and characterization of UDP-glucose : curcumin glucoside 1,6-glucosyltransferase from Catharanthus roseus cell suspension cultures. Plant Cell Physiol. 2007 Nov;48(11):1635–43. doi: 10.1093/pcp/pcm138. PMID: 17940060.; TAHARA S. A Journey of Twenty-Five Years through the Ecological Biochemistry of Flavonoids. Bioscience, Biotechnology, and Biochemistry. 2007 Jun 23;71(6):1387–404. doi: 10.1271/bbb.70028.; Martens S, Mithöfer A. Flavones and flavone synthases. Phytochemistry. 2005 Oct;66(20):2399–407. doi: 10.1016/j.phytochem.2005.07.013. PMID: 16137727.; Vogt T, Jones P. Glycosyltransferases in plant natural product synthesis: characterization of a supergene family. Trends Plant Sci. 2000 Sep;5(9):380–6. doi: 10.1016/s1360-1385(00)01720-9. PMID: 10973093. |
| kaempferol gentiobioside biosynthesis Accession ID: PlantCyc:CROSEUS_PWY-7143 |
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Lei Y, Chen J, Zhang W, Fu W, Wu G, Wei H, Wang Q, Ruan J. In vivo investigation on the potential of galangin, kaempferol and myricetin for protection of D-galactose-induced cognitive impairment. Food Chem. 2012 Dec 15;135(4):2702–7. doi: 10.1016/j.foodchem.2012.07.043. PMID: 22980861.; Luo H, Jiang B, Li B, Li Z, Jiang BH, Chen YC. Kaempferol nanoparticles achieve strong and selective inhibition of ovarian cancer cell viability. Int J Nanomedicine. 2012;7():3951–9. PMID: 22866004; PMCID: PMC3410694.; Liu L, Xie Y, Song Z, Shang S, Chen X. Influence of dietary flavonoids on the glycation of plasma proteins. Mol Biosyst. 2012 Aug;8(8):2183–7. doi: 10.1039/c2mb25038a. PMID: 22710272.; Guo AJ, Choi RC, Zheng KY, Chen VP, Dong TT, Wang Z, Vollmer G, Lau DT, Tsim KW. Kaempferol as a flavonoid induces osteoblastic differentiation via estrogen receptor signaling. Chinese Medicine. 2012 Apr 30;7(1):10. doi: 10.1186/1749-8546-7-10.; Saito N, Tatsuzawa F, Toki K, Shinoda K, Shigihara A, Honda T. The blue anthocyanin pigments from the blue flowers of Heliophila coronopifolia L. (Brassicaceae). Phytochemistry. 2011 Dec;72(17):2219–29. doi: 10.1016/j.phytochem.2011.07.020. PMID: 21903230.; Bollina V, Kushalappa AC, Choo TM, Dion Y, Rioux S. Identification of metabolites related to mechanisms of resistance in barley against Fusarium graminearum, based on mass spectrometry. Plant Mol Biol. 2011 Nov;77(4-5):355–70. doi: 10.1007/s11103-011-9815-8. PMID: 21830145.; Iwashina T, Yamaguchi M, Nakayama M, Onozaki T, Yoshida H, Kawanobu S, Ono H, Okamura M. Kaempferol Glycosides in the Flowers of Carnation and their Contribution to the Creamy White Flower Color. Natural Product Communications. 2010 Dec;5(12). doi: 10.1177/1934578x1000501213.; Owens DK, McIntosh CA. Identification, recombinant expression, and biochemical characterization of a flavonol 3-O-glucosyltransferase clone from Citrus paradisi. Phytochemistry. 2009 Jul;70(11-12):1382–91. doi: 10.1016/j.phytochem.2009.07.027. PMID: 19733370.; Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H. Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus. Plant Cell Physiol. 2009 Aug;50(8):1401–15. doi: 10.1093/pcp/pcp088. PMID: 19561332.; Oguchi Y, Masada S, Kondo T, Terasaka K, Mizukami H. Purification and characterization of UDP-glucose : curcumin glucoside 1,6-glucosyltransferase from Catharanthus roseus cell suspension cultures. Plant Cell Physiol. 2007 Nov;48(11):1635–43. doi: 10.1093/pcp/pcm138. PMID: 17940060.; TAHARA S. A Journey of Twenty-Five Years through the Ecological Biochemistry of Flavonoids. Bioscience, Biotechnology, and Biochemistry. 2007 Jun 23;71(6):1387–404. doi: 10.1271/bbb.70028.; Martens S, Mithöfer A. Flavones and flavone synthases. Phytochemistry. 2005 Oct;66(20):2399–407. doi: 10.1016/j.phytochem.2005.07.013. PMID: 16137727. |
| momilactone A biosynthesis Accession ID: PlantCyc:ORYZA_PWY-7477 |
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Wang Q, Hillwig ML, Okada K, Yamazaki K, Wu Y, Swaminathan S, Yamane H, Peters RJ. Characterization of CYP76M5–8 Indicates Metabolic Plasticity within a Plant Biosynthetic Gene Cluster. Journal of Biological Chemistry. 2012 Feb;287(9):6159–68. doi: 10.1074/jbc.m111.305599.; Kato-Noguchi H. The chemical cross talk between rice and barnyardgrass. Plant Signaling & Behavior. 2011 Aug;6(8):1207–9. doi: 10.4161/psb.6.8.15869.; Wang Q, Hillwig ML, Peters RJ. CYP99A3: functional identification of a diterpene oxidase from the momilactone biosynthetic gene cluster in rice. The Plant Journal. 2010 Nov 17;65(1):87–95. doi: 10.1111/j.1365-313x.2010.04408.x.; Osbourn A. Gene clusters for secondary metabolic pathways: an emerging theme in plant biology. Plant Physiol. 2010 Oct;154(2):531–5. PMID: 20921179; PMCID: PMC2949040.; Hasegawa M, Mitsuhara I, Seo S, Imai T, Koga J, Okada K, Yamane H, Ohashi Y. Phytoalexin accumulation in the interaction between rice and the blast fungus. Mol Plant Microbe Interact. 2010 Aug;23(8):1000–11. doi: 10.1094/mpmi-23-8-1000. PMID: 20615111.; Okada A, Okada K, Miyamoto K, Koga J, Shibuya N, Nojiri H, Yamane H. OsTGAP1, a bZIP Transcription Factor, Coordinately Regulates the Inductive Production of Diterpenoid Phytoalexins in Rice. Journal of Biological Chemistry. 2009 Sep;284(39):26510–8. doi: 10.1074/jbc.m109.036871.; Osbourn AE, Field B. Operons. Cellular and Molecular Life Sciences. 2009 Aug 07;66(23):3755–75. doi: 10.1007/s00018-009-0114-3.; Kato-Noguchi H. Secretion of momilactone A and B by the mossHypnum plumaeforme. Plant Signaling & Behavior. 2009 Aug;4(8):737–9. doi: 10.4161/psb.4.8.9080.; Fischbach MA, Walsh CT, Clardy J. The evolution of gene collectives: How natural selection drives chemical innovation. Proc Natl Acad Sci U S A. 2008 Mar 25;105(12):4601–8. PMID: 18216259; PMCID: PMC2290807.; Shimizu T, Jikumaru Y, Okada A, Okada K, Koga J, Umemura K, Minami E, Shibuya N, Hasegawa M, Kodama O, Nojiri H, Yamane H. Effects of a bile acid elicitor, cholic acid, on the biosynthesis of diterpenoid phytoalexins in suspension-cultured rice cells. Phytochemistry. 2008 Feb;69(4):973–81. doi: 10.1016/j.phytochem.2007.10.005. PMID: 18045629.; NOZAKI H, HAYASHI K, NISHIMURA N, KAWAIDE H, MATSUO A, TAKAOKA D. Momilactone A and B as Allelochemicals from MossHypnum plumaeforme: First Occurrence in Bryophytes. Bioscience, Biotechnology, and Biochemistry. 2007 Dec 23;71(12):3127–30. doi: 10.1271/bbb.70625.; Shimura K, Okada A, Okada K, Jikumaru Y, Ko K, Toyomasu T, Sassa T, Hasegawa M, Kodama O, Shibuya N, Koga J, Nojiri H, Yamane H. Identification of a Biosynthetic Gene Cluster in Rice for Momilactones. Journal of Biological Chemistry. 2007 Nov;282(47):34013–8. doi: 10.1074/jbc.m703344200.; Kato-Noguchi H, Kujime H, Ino T. UV-induced momilactone B accumulation in rice rhizosphere. J Plant Physiol. 2007 Nov;164(11):1548–51. doi: 10.1016/j.jplph.2006.12.008. PMID: 17498837.; Xu M, Wilderman PR, Morrone D, Xu J, Roy A, Margis-Pinheiro M, Upadhyaya NM, Coates RM, Peters RJ. Functional characterization of the rice kaurene synthase-like gene family. Phytochemistry. 2007 Feb;68(3):312–26. doi: 10.1016/j.phytochem.2006.10.016. PMID: 17141283.; Peters RJ. Uncovering the complex metabolic network underlying diterpenoid phytoalexin biosynthesis in rice and other cereal crop plants. Phytochemistry. 2006 Nov;67(21):2307–17. doi: 10.1016/j.phytochem.2006.08.009. PMID: 16956633.; Prisic S, Xu M, Wilderman PR, Peters RJ. Rice contains two disparate ent-copalyl diphosphate synthases with distinct metabolic functions. Plant Physiol. 2004 Dec;136(4):4228–36. PMID: 15542489; PMCID: PMC535852.; Otomo K, Kenmoku H, Oikawa H, König WA, Toshima H, Mitsuhashi W, Yamane H, Sassa T, Toyomasu T. Biological functions of ent- and syn-copalyl diphosphate synthases in rice: key enzymes for the branch point of gibberellin and phytoalexin biosynthesis. The Plant Journal. 2004 Jul 30;39(6):886–93. doi: 10.1111/j.1365-313x.2004.02175.x.; Kato-Noguchi H. Allelopathic substance in rice root exudates: rediscovery of momilactone B as an allelochemical. J Plant Physiol. 2004 Mar;161(3):271–6. doi: 10.1078/0176-1617-01188. PMID: 15077625.; Kato-Noguchi H, Ino T. Rice seedlings release momilactone B into the environment. Phytochemistry. 2003 Jul;63(5):551–4. doi: 10.1016/s0031-9422(03)00194-8. PMID: 12809715.; Germain J, Deslongchamps P. Total synthesis of (+/-)-momilactone A. J Org Chem. 2002 Jul 26;67(15):5269–78. doi: 10.1021/jo025873l. PMID: 12126415.; Kato-Noguchi H, Ino T, Sata N, Yamamura S. Isolation and identification of a potent allelopathic substance in rice root exudates. Physiol Plant. 2002 Jul;115(3):401–5. doi: 10.1034/j.1399-3054.2002.1150310.x. PMID: 12081533.; Nojiri H, Sugimori M, Yamane H, Nishimura Y, Yamada A, Shibuya N, Kodama O, Murofushi N, Omori T. Involvement of Jasmonic Acid in Elicitor-Induced Phytoalexin Production in Suspension-Cultured Rice Cells. Plant Physiol. 1996 Feb;110(2):387–92. PMID: 12226190; PMCID: PMC157731. |
| volatile benzenoid biosynthesis I (ester formation) Accession ID: PlantCyc:PLANT_PWY-4203 |
|
Danner H, Boeckler GA, Irmisch S, Yuan JS, Chen F, Gershenzon J, Unsicker SB, Köllner TG. Four terpene synthases produce major compounds of the gypsy moth feeding-induced volatile blend of Populus trichocarpa. Phytochemistry. 2011 Jun;72(9):897–908. doi: 10.1016/j.phytochem.2011.03.014. PMID: 21492885.; Zhao N, Guan J, Forouhar F, Tschaplinski TJ, Cheng ZM, Tong L, Chen F. Two poplar methyl salicylate esterases display comparable biochemical properties but divergent expression patterns. Phytochemistry. 2009 Jan;70(1):32–9. doi: 10.1016/j.phytochem.2008.11.014. PMID: 19136124.; Dudareva N, Pichersky E, Gershenzon J. Biochemistry of plant volatiles. Plant Physiol. 2004 Aug;135(4):1893–902. PMID: 15326281; PMCID: PMC520761.; Chen F, D'Auria JC, Tholl D, Ross JR, Gershenzon J, Noel JP, Pichersky E. An Arabidopsis thaliana gene for methylsalicylate biosynthesis, identified by a biochemical genomics approach, has a role in defense. The Plant Journal. 2003 Nov 18;36(5):577–88. doi: 10.1046/j.1365-313x.2003.01902.x.; Degenhardt J, Gershenzon J, Baldwin IT, Kessler A. Attracting friends to feast on foes: engineering terpene emission to make crop plants more attractive to herbivore enemies. Curr Opin Biotechnol. 2003 Apr;14(2):169–76. doi: 10.1016/s0958-1669(03)00025-9. PMID: 12732318.; D'Auria JC, Chen F, Pichersky E. Characterization of an acyltransferase capable of synthesizing benzylbenzoate and other volatile esters in flowers and damaged leaves of Clarkia breweri. Plant Physiol. 2002 Sep;130(1):466–76. PMID: 12226525; PMCID: PMC166578.; Dudareva N, Raguso RA, Wang J, Ross JR, Pichersky E. Floral scent production in Clarkia breweri. III. Enzymatic synthesis and emission of benzenoid esters. Plant Physiol. 1998 Feb;116(2):599–604. PMID: 9489012; PMCID: PMC35117. |
| volatile benzenoid biosynthesis I (ester formation) Accession ID: PlantCyc:ARA_PWY-4203 |
|
Dudareva N, Pichersky E, Gershenzon J. Biochemistry of plant volatiles. Plant Physiol. 2004 Aug;135(4):1893–902. PMID: 15326281; PMCID: PMC520761.; Chen F, D'Auria JC, Tholl D, Ross JR, Gershenzon J, Noel JP, Pichersky E. An Arabidopsis thaliana gene for methylsalicylate biosynthesis, identified by a biochemical genomics approach, has a role in defense. The Plant Journal. 2003 Nov 18;36(5):577–88. doi: 10.1046/j.1365-313x.2003.01902.x.; Degenhardt J, Gershenzon J, Baldwin IT, Kessler A. Attracting friends to feast on foes: engineering terpene emission to make crop plants more attractive to herbivore enemies. Curr Opin Biotechnol. 2003 Apr;14(2):169–76. doi: 10.1016/s0958-1669(03)00025-9. PMID: 12732318.; D'Auria JC, Chen F, Pichersky E. Characterization of an acyltransferase capable of synthesizing benzylbenzoate and other volatile esters in flowers and damaged leaves of Clarkia breweri. Plant Physiol. 2002 Sep;130(1):466–76. PMID: 12226525; PMCID: PMC166578.; Dudareva N, Raguso RA, Wang J, Ross JR, Pichersky E. Floral scent production in Clarkia breweri. III. Enzymatic synthesis and emission of benzenoid esters. Plant Physiol. 1998 Feb;116(2):599–604. PMID: 9489012; PMCID: PMC35117. |
| curcumin glucoside biosynthesis Accession ID: PlantCyc:CROSEUS_PWY-4421 |
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Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H. Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus. Plant Cell Physiol. 2009 Aug;50(8):1401–15. doi: 10.1093/pcp/pcp088. PMID: 19561332.; Kaminaga Y, Sahin FP, Mizukami H. Molecular cloning and characterization of a glucosyltransferase catalyzing glucosylation of curcumin in cultured Catharanthus roseus cells. FEBS Lett. 2004 Jun 04;567(2-3):197–202. doi: 10.1016/j.febslet.2004.04.056. PMID: 15178322.; Kaminaga Y, Nagatsu A, Akiyama T, Sugimoto N, Yamazaki T, Maitani T, Mizukami H. Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus. FEBS Lett. 2003 Dec 04;555(2):311–6. doi: 10.1016/s0014-5793(03)01265-1. PMID: 14644434.; Tønnesen HH, Másson M, Loftsson T. Studies of curcumin and curcuminoids. XXVII. Cyclodextrin complexation: solubility, chemical and photochemical stability. International Journal of Pharmaceutics. 2002 Sep;244(1-2):127–35. doi: 10.1016/s0378-5173(02)00323-x.; Gomes Dde C, Alegrio LV, de Lima ME, Leon LL, Araújo CA. Synthetic derivatives of curcumin and their activity against Leishmania amazonensis. Arzneimittelforschung. 2002;52(2):120–4. PMID: 11878200. |
| quercetin gentiotetraside biosynthesis Accession ID: PlantCyc:CROSEUS_PWY-7137 |
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Dixon RA, Pasinetti GM. Flavonoids and isoflavonoids: from plant biology to agriculture and neuroscience. Plant Physiol. 2010 Oct;154(2):453–7. PMID: 20921162; PMCID: PMC2948995.; Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H. Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus. Plant Cell Physiol. 2009 Aug;50(8):1401–15. doi: 10.1093/pcp/pcp088. PMID: 19561332.; Oguchi Y, Masada S, Kondo T, Terasaka K, Mizukami H. Purification and characterization of UDP-glucose : curcumin glucoside 1,6-glucosyltransferase from Catharanthus roseus cell suspension cultures. Plant Cell Physiol. 2007 Nov;48(11):1635–43. doi: 10.1093/pcp/pcm138. PMID: 17940060.; Ververidis F, Trantas E, Douglas C, Vollmer G, Kretzschmar G, Panopoulos N. Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health. Biotechnol J. 2007 Oct;2(10):1214–34. doi: 10.1002/biot.200700084. PMID: 17935117.; Lee ER, Kang GH, Cho SG. Effect of flavonoids on human health: old subjects but new challenges. Recent Pat Biotechnol. 2007;1(2):139–50. doi: 10.2174/187220807780809445. PMID: 19075837.; Martens S, Mithöfer A. Flavones and flavone synthases. Phytochemistry. 2005 Oct;66(20):2399–407. doi: 10.1016/j.phytochem.2005.07.013. PMID: 16137727.; Morita Y, Hoshino A, Kikuchi Y, Okuhara H, Ono E, Tanaka Y, Fukui Y, Saito N, Nitasaka E, Noguchi H, Iida S. Japanese morning glory dusky mutants displaying reddish-brown or purplish-gray flowers are deficient in a novel glycosylation enzyme for anthocyanin biosynthesis, UDP-glucose:anthocyanidin 3-O-glucoside-2''-O-glucosyltransferase, due to 4-bp insertions in the gene. The Plant Journal. 2005 Mar 15;42(3):353–63. doi: 10.1111/j.1365-313x.2005.02383.x.; Kaminaga Y, Nagatsu A, Akiyama T, Sugimoto N, Yamazaki T, Maitani T, Mizukami H. Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus. FEBS Lett. 2003 Dec 04;555(2):311–6. doi: 10.1016/s0014-5793(03)01265-1. PMID: 14644434.; Wink M. Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry. 2003 Sep;64(1):3–19. doi: 10.1016/s0031-9422(03)00300-5. PMID: 12946402.; Harborne JB, Williams CA. Advances in flavonoid research since 1992. Phytochemistry. 2000 Nov;55(6):481–504. doi: 10.1016/s0031-9422(00)00235-1. PMID: 11130659.; Vogt T, Jones P. Glycosyltransferases in plant natural product synthesis: characterization of a supergene family. Trends Plant Sci. 2000 Sep;5(9):380–6. doi: 10.1016/s1360-1385(00)01720-9. PMID: 10973093. |
| sesaminol glucoside biosynthesis Accession ID: PlantCyc:CROSEUS_PWY-7139 |
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Um MY, Ahn JY, Kim S, Kim MK, Ha TY. Sesaminol Glucosides Protect .BETA.-Amyloid Peptide-Induced Cognitive Deficits in Mice. Biological & Pharmaceutical Bulletin. 2009;32(9):1516–20. doi: 10.1248/bpb.32.1516.; Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H. Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus. Plant Cell Physiol. 2009 Aug;50(8):1401–15. doi: 10.1093/pcp/pcp088. PMID: 19561332.; Jan KC, Hwang LS, Ho CT. Biotransformation of sesaminol triglucoside to mammalian lignans by intestinal microbiota. J Agric Food Chem. 2009 Jul 22;57(14):6101–6. doi: 10.1021/jf901215j. PMID: 19537732.; Noguchi A, Fukui Y, Iuchi-Okada A, Kakutani S, Satake H, Iwashita T, Nakao M, Umezawa T, Ono E. Sequential glucosylation of a furofuran lignan, (+)-sesaminol, by Sesamum indicum UGT71A9 and UGT94D1 glucosyltransferases. The Plant Journal. 2008 Jan 31;54(3):415–27. doi: 10.1111/j.1365-313x.2008.03428.x.; Lee SY, Son DJ, Lee YK, Lee JW, Lee HJ, Yun YW, Ha TY, Hong JT. Inhibitory effect of sesaminol glucosides on lipopolysaccharide-induced NF-kappaB activation and target gene expression in cultured rat astrocytes. Neurosci Res. 2006 Oct;56(2):204–12. doi: 10.1016/j.neures.2006.06.005. PMID: 16842873.; Liu Z, Saarinen NM, Thompson LU. Sesamin Is One of the Major Precursors of Mammalian Lignans in Sesame Seed (Sesamum indicum) as Observed In Vitro and in Rats , The Journal of Nutrition. 2006 Apr;136(4):906–12. doi: 10.1093/jn/136.4.906.; Moazzami AA, Andersson RE, Kamal-Eldin A. HPLC analysis of sesaminol glucosides in sesame seeds. J Agric Food Chem. 2006 Feb 08;54(3):633–8. doi: 10.1021/jf051541g. PMID: 16448160. |
| oryzalexin D and E biosynthesis Accession ID: PlantCyc:ORYZA_PWY-7478 |
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Wu Y, Wang Q, Hillwig ML, Peters RJ. Picking sides: distinct roles for CYP76M6 and CYP76M8 in rice oryzalexin biosynthesis. Biochem J. 2013 Sep 01;454(2):209–16. PMID: 23795884; PMCID: PMC3787970.; Sang T, Ge S. Understanding rice domestication and implications for cultivar improvement. Curr Opin Plant Biol. 2013 May;16(2):139–46. doi: 10.1016/j.pbi.2013.03.003. PMID: 23545218.; Wang Q, Hillwig ML, Okada K, Yamazaki K, Wu Y, Swaminathan S, Yamane H, Peters RJ. Characterization of CYP76M5–8 Indicates Metabolic Plasticity within a Plant Biosynthetic Gene Cluster. Journal of Biological Chemistry. 2012 Feb;287(9):6159–68. doi: 10.1074/jbc.m111.305599.; Wang Q, Hillwig ML, Wu Y, Peters RJ. CYP701A8: a rice ent-kaurene oxidase paralog diverted to more specialized diterpenoid metabolism. Plant Physiol. 2012 Mar;158(3):1418–25. PMID: 22247270; PMCID: PMC3291257.; Osbourn A. Gene clusters for secondary metabolic pathways: an emerging theme in plant biology. Plant Physiol. 2010 Oct;154(2):531–5. PMID: 20921179; PMCID: PMC2949040.; Hasegawa M, Mitsuhara I, Seo S, Imai T, Koga J, Okada K, Yamane H, Ohashi Y. Phytoalexin accumulation in the interaction between rice and the blast fungus. Mol Plant Microbe Interact. 2010 Aug;23(8):1000–11. doi: 10.1094/mpmi-23-8-1000. PMID: 20615111.; Osbourn AE, Field B. Operons. Cellular and Molecular Life Sciences. 2009 Aug 07;66(23):3755–75. doi: 10.1007/s00018-009-0114-3.; Fischbach MA, Walsh CT, Clardy J. The evolution of gene collectives: How natural selection drives chemical innovation. Proc Natl Acad Sci U S A. 2008 Mar 25;105(12):4601–8. PMID: 18216259; PMCID: PMC2290807.; Cyr A, Wilderman PR, Determan M, Peters RJ. A modular approach for facile biosynthesis of labdane-related diterpenes. J Am Chem Soc. 2007 May 30;129(21):6684–5. PMID: 17480080; PMCID: PMC2518946.; Xu M, Wilderman PR, Peters RJ. Following evolution's lead to a single residue switch for diterpene synthase product outcome. Proc Natl Acad Sci U S A. 2007 May 01;104(18):7397–401. PMID: 17456599; PMCID: PMC1855280.; Xu M, Wilderman PR, Morrone D, Xu J, Roy A, Margis-Pinheiro M, Upadhyaya NM, Coates RM, Peters RJ. Functional characterization of the rice kaurene synthase-like gene family. Phytochemistry. 2007 Feb;68(3):312–26. doi: 10.1016/j.phytochem.2006.10.016. PMID: 17141283.; Peters RJ. Uncovering the complex metabolic network underlying diterpenoid phytoalexin biosynthesis in rice and other cereal crop plants. Phytochemistry. 2006 Nov;67(21):2307–17. doi: 10.1016/j.phytochem.2006.08.009. PMID: 16956633.; Prisic S, Xu M, Wilderman PR, Peters RJ. Rice contains two disparate ent-copalyl diphosphate synthases with distinct metabolic functions. Plant Physiol. 2004 Dec;136(4):4228–36. PMID: 15542489; PMCID: PMC535852.; Otomo K, Kenmoku H, Oikawa H, König WA, Toshima H, Mitsuhashi W, Yamane H, Sassa T, Toyomasu T. Biological functions of ent- and syn-copalyl diphosphate synthases in rice: key enzymes for the branch point of gibberellin and phytoalexin biosynthesis. The Plant Journal. 2004 Jul 30;39(6):886–93. doi: 10.1111/j.1365-313x.2004.02175.x. |
| quercetin gentiotetraside biosynthesis Accession ID: PlantCyc:PLANT_PWY-7137 |
|
Dixon RA, Pasinetti GM. Flavonoids and isoflavonoids: from plant biology to agriculture and neuroscience. Plant Physiol. 2010 Oct;154(2):453–7. PMID: 20921162; PMCID: PMC2948995.; Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H. Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus. Plant Cell Physiol. 2009 Aug;50(8):1401–15. doi: 10.1093/pcp/pcp088. PMID: 19561332.; Oguchi Y, Masada S, Kondo T, Terasaka K, Mizukami H. Purification and characterization of UDP-glucose : curcumin glucoside 1,6-glucosyltransferase from Catharanthus roseus cell suspension cultures. Plant Cell Physiol. 2007 Nov;48(11):1635–43. doi: 10.1093/pcp/pcm138. PMID: 17940060.; Ververidis F, Trantas E, Douglas C, Vollmer G, Kretzschmar G, Panopoulos N. Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health. Biotechnol J. 2007 Oct;2(10):1214–34. doi: 10.1002/biot.200700084. PMID: 17935117.; Lee ER, Kang GH, Cho SG. Effect of flavonoids on human health: old subjects but new challenges. Recent Pat Biotechnol. 2007;1(2):139–50. doi: 10.2174/187220807780809445. PMID: 19075837.; Martens S, Mithöfer A. Flavones and flavone synthases. Phytochemistry. 2005 Oct;66(20):2399–407. doi: 10.1016/j.phytochem.2005.07.013. PMID: 16137727.; Morita Y, Hoshino A, Kikuchi Y, Okuhara H, Ono E, Tanaka Y, Fukui Y, Saito N, Nitasaka E, Noguchi H, Iida S. Japanese morning glory dusky mutants displaying reddish-brown or purplish-gray flowers are deficient in a novel glycosylation enzyme for anthocyanin biosynthesis, UDP-glucose:anthocyanidin 3-O-glucoside-2''-O-glucosyltransferase, due to 4-bp insertions in the gene. The Plant Journal. 2005 Mar 15;42(3):353–63. doi: 10.1111/j.1365-313x.2005.02383.x.; Kaminaga Y, Nagatsu A, Akiyama T, Sugimoto N, Yamazaki T, Maitani T, Mizukami H. Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus. FEBS Lett. 2003 Dec 04;555(2):311–6. doi: 10.1016/s0014-5793(03)01265-1. PMID: 14644434.; Wink M. Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective. Phytochemistry. 2003 Sep;64(1):3–19. doi: 10.1016/s0031-9422(03)00300-5. PMID: 12946402.; Harborne JB, Williams CA. Advances in flavonoid research since 1992. Phytochemistry. 2000 Nov;55(6):481–504. doi: 10.1016/s0031-9422(00)00235-1. PMID: 11130659.; Vogt T, Jones P. Glycosyltransferases in plant natural product synthesis: characterization of a supergene family. Trends Plant Sci. 2000 Sep;5(9):380–6. doi: 10.1016/s1360-1385(00)01720-9. PMID: 10973093. |
| sesaminol glucoside biosynthesis Accession ID: PlantCyc:PLANT_PWY-7139 |
|
Um MY, Ahn JY, Kim S, Kim MK, Ha TY. Sesaminol Glucosides Protect .BETA.-Amyloid Peptide-Induced Cognitive Deficits in Mice. Biological & Pharmaceutical Bulletin. 2009;32(9):1516–20. doi: 10.1248/bpb.32.1516.; Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H. Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus. Plant Cell Physiol. 2009 Aug;50(8):1401–15. doi: 10.1093/pcp/pcp088. PMID: 19561332.; Jan KC, Hwang LS, Ho CT. Biotransformation of sesaminol triglucoside to mammalian lignans by intestinal microbiota. J Agric Food Chem. 2009 Jul 22;57(14):6101–6. doi: 10.1021/jf901215j. PMID: 19537732.; Noguchi A, Fukui Y, Iuchi-Okada A, Kakutani S, Satake H, Iwashita T, Nakao M, Umezawa T, Ono E. Sequential glucosylation of a furofuran lignan, (+)-sesaminol, by Sesamum indicum UGT71A9 and UGT94D1 glucosyltransferases. The Plant Journal. 2008 Jan 31;54(3):415–27. doi: 10.1111/j.1365-313x.2008.03428.x.; Lee SY, Son DJ, Lee YK, Lee JW, Lee HJ, Yun YW, Ha TY, Hong JT. Inhibitory effect of sesaminol glucosides on lipopolysaccharide-induced NF-kappaB activation and target gene expression in cultured rat astrocytes. Neurosci Res. 2006 Oct;56(2):204–12. doi: 10.1016/j.neures.2006.06.005. PMID: 16842873.; Liu Z, Saarinen NM, Thompson LU. Sesamin Is One of the Major Precursors of Mammalian Lignans in Sesame Seed (Sesamum indicum) as Observed In Vitro and in Rats , The Journal of Nutrition. 2006 Apr;136(4):906–12. doi: 10.1093/jn/136.4.906.; Moazzami AA, Andersson RE, Kamal-Eldin A. HPLC analysis of sesaminol glucosides in sesame seeds. J Agric Food Chem. 2006 Feb 08;54(3):633–8. doi: 10.1021/jf051541g. PMID: 16448160. |
| momilactone A biosynthesis Accession ID: PlantCyc:PLANT_PWY-7477 |
|
Wang Q, Hillwig ML, Okada K, Yamazaki K, Wu Y, Swaminathan S, Yamane H, Peters RJ. Characterization of CYP76M5–8 Indicates Metabolic Plasticity within a Plant Biosynthetic Gene Cluster. Journal of Biological Chemistry. 2012 Feb;287(9):6159–68. doi: 10.1074/jbc.m111.305599.; Kato-Noguchi H. The chemical cross talk between rice and barnyardgrass. Plant Signaling & Behavior. 2011 Aug;6(8):1207–9. doi: 10.4161/psb.6.8.15869.; Wang Q, Hillwig ML, Peters RJ. CYP99A3: functional identification of a diterpene oxidase from the momilactone biosynthetic gene cluster in rice. The Plant Journal. 2010 Nov 17;65(1):87–95. doi: 10.1111/j.1365-313x.2010.04408.x.; Osbourn A. Gene clusters for secondary metabolic pathways: an emerging theme in plant biology. Plant Physiol. 2010 Oct;154(2):531–5. PMID: 20921179; PMCID: PMC2949040.; Hasegawa M, Mitsuhara I, Seo S, Imai T, Koga J, Okada K, Yamane H, Ohashi Y. Phytoalexin accumulation in the interaction between rice and the blast fungus. Mol Plant Microbe Interact. 2010 Aug;23(8):1000–11. doi: 10.1094/mpmi-23-8-1000. PMID: 20615111.; Okada A, Okada K, Miyamoto K, Koga J, Shibuya N, Nojiri H, Yamane H. OsTGAP1, a bZIP Transcription Factor, Coordinately Regulates the Inductive Production of Diterpenoid Phytoalexins in Rice. Journal of Biological Chemistry. 2009 Sep;284(39):26510–8. doi: 10.1074/jbc.m109.036871.; Osbourn AE, Field B. Operons. Cellular and Molecular Life Sciences. 2009 Aug 07;66(23):3755–75. doi: 10.1007/s00018-009-0114-3.; Kato-Noguchi H. Secretion of momilactone A and B by the mossHypnum plumaeforme. Plant Signaling & Behavior. 2009 Aug;4(8):737–9. doi: 10.4161/psb.4.8.9080.; Fischbach MA, Walsh CT, Clardy J. The evolution of gene collectives: How natural selection drives chemical innovation. Proc Natl Acad Sci U S A. 2008 Mar 25;105(12):4601–8. PMID: 18216259; PMCID: PMC2290807.; Shimizu T, Jikumaru Y, Okada A, Okada K, Koga J, Umemura K, Minami E, Shibuya N, Hasegawa M, Kodama O, Nojiri H, Yamane H. Effects of a bile acid elicitor, cholic acid, on the biosynthesis of diterpenoid phytoalexins in suspension-cultured rice cells. Phytochemistry. 2008 Feb;69(4):973–81. doi: 10.1016/j.phytochem.2007.10.005. PMID: 18045629.; NOZAKI H, HAYASHI K, NISHIMURA N, KAWAIDE H, MATSUO A, TAKAOKA D. Momilactone A and B as Allelochemicals from MossHypnum plumaeforme: First Occurrence in Bryophytes. Bioscience, Biotechnology, and Biochemistry. 2007 Dec 23;71(12):3127–30. doi: 10.1271/bbb.70625.; Shimura K, Okada A, Okada K, Jikumaru Y, Ko K, Toyomasu T, Sassa T, Hasegawa M, Kodama O, Shibuya N, Koga J, Nojiri H, Yamane H. Identification of a Biosynthetic Gene Cluster in Rice for Momilactones. Journal of Biological Chemistry. 2007 Nov;282(47):34013–8. doi: 10.1074/jbc.m703344200.; Kato-Noguchi H, Kujime H, Ino T. UV-induced momilactone B accumulation in rice rhizosphere. J Plant Physiol. 2007 Nov;164(11):1548–51. doi: 10.1016/j.jplph.2006.12.008. PMID: 17498837.; Xu M, Wilderman PR, Morrone D, Xu J, Roy A, Margis-Pinheiro M, Upadhyaya NM, Coates RM, Peters RJ. Functional characterization of the rice kaurene synthase-like gene family. Phytochemistry. 2007 Feb;68(3):312–26. doi: 10.1016/j.phytochem.2006.10.016. PMID: 17141283.; Peters RJ. Uncovering the complex metabolic network underlying diterpenoid phytoalexin biosynthesis in rice and other cereal crop plants. Phytochemistry. 2006 Nov;67(21):2307–17. doi: 10.1016/j.phytochem.2006.08.009. PMID: 16956633.; Prisic S, Xu M, Wilderman PR, Peters RJ. Rice contains two disparate ent-copalyl diphosphate synthases with distinct metabolic functions. Plant Physiol. 2004 Dec;136(4):4228–36. PMID: 15542489; PMCID: PMC535852.; Otomo K, Kenmoku H, Oikawa H, König WA, Toshima H, Mitsuhashi W, Yamane H, Sassa T, Toyomasu T. Biological functions of ent- and syn-copalyl diphosphate synthases in rice: key enzymes for the branch point of gibberellin and phytoalexin biosynthesis. The Plant Journal. 2004 Jul 30;39(6):886–93. doi: 10.1111/j.1365-313x.2004.02175.x.; Kato-Noguchi H. Allelopathic substance in rice root exudates: rediscovery of momilactone B as an allelochemical. J Plant Physiol. 2004 Mar;161(3):271–6. doi: 10.1078/0176-1617-01188. PMID: 15077625.; Kato-Noguchi H, Ino T. Rice seedlings release momilactone B into the environment. Phytochemistry. 2003 Jul;63(5):551–4. doi: 10.1016/s0031-9422(03)00194-8. PMID: 12809715.; Germain J, Deslongchamps P. Total synthesis of (+/-)-momilactone A. J Org Chem. 2002 Jul 26;67(15):5269–78. doi: 10.1021/jo025873l. PMID: 12126415.; Kato-Noguchi H, Ino T, Sata N, Yamamura S. Isolation and identification of a potent allelopathic substance in rice root exudates. Physiol Plant. 2002 Jul;115(3):401–5. doi: 10.1034/j.1399-3054.2002.1150310.x. PMID: 12081533.; Nojiri H, Sugimori M, Yamane H, Nishimura Y, Yamada A, Shibuya N, Kodama O, Murofushi N, Omori T. Involvement of Jasmonic Acid in Elicitor-Induced Phytoalexin Production in Suspension-Cultured Rice Cells. Plant Physiol. 1996 Feb;110(2):387–92. PMID: 12226190; PMCID: PMC157731. |
| myricetin gentiobioside biosynthesis Accession ID: PlantCyc:PLANT_PWY-7140 |
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Vepsäläinen S, Koivisto H, Pekkarinen E, Mäkinen P, Dobson G, McDougall GJ, Stewart D, Haapasalo A, Karjalainen RO, Tanila H, Hiltunen M. Anthocyanin-enriched bilberry and blackcurrant extracts modulate amyloid precursor protein processing and alleviate behavioral abnormalities in the APP/PS1 mouse model of Alzheimer's disease. The Journal of Nutritional Biochemistry. 2013 Jan;24(1):360–70. doi: 10.1016/j.jnutbio.2012.07.006.; Fiori J, Naldi M, Bartolini M, Andrisano V. Disclosure of a fundamental clue for the elucidation of the myricetin mechanism of action as amyloid aggregation inhibitor by mass spectrometry. Electrophoresis. 2012 Nov;33(22):3380–6. doi: 10.1002/elps.201200186. PMID: 22961751.; Chobot V, Hadacek F. Exploration of pro-oxidant and antioxidant activities of the flavonoid myricetin. Redox Report. 2011 Nov;16(6):242–7. doi: 10.1179/1351000211y.0000000015.; Kumar D, Kumar S, Gupta J, Arya R, Gupta A. A review on chemical and biological properties of Cayratia trifolia Linn. (Vitaceae). Pharmacogn Rev. 2011 Jul;5(10):184–8. PMID: 22279376; PMCID: PMC3263053.; Owens DK, McIntosh CA. Identification, recombinant expression, and biochemical characterization of a flavonol 3-O-glucosyltransferase clone from Citrus paradisi. Phytochemistry. 2009 Jul;70(11-12):1382–91. doi: 10.1016/j.phytochem.2009.07.027. PMID: 19733370.; Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H. Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus. Plant Cell Physiol. 2009 Aug;50(8):1401–15. doi: 10.1093/pcp/pcp088. PMID: 19561332.; Oguchi Y, Masada S, Kondo T, Terasaka K, Mizukami H. Purification and characterization of UDP-glucose : curcumin glucoside 1,6-glucosyltransferase from Catharanthus roseus cell suspension cultures. Plant Cell Physiol. 2007 Nov;48(11):1635–43. doi: 10.1093/pcp/pcm138. PMID: 17940060.; TAHARA S. A Journey of Twenty-Five Years through the Ecological Biochemistry of Flavonoids. Bioscience, Biotechnology, and Biochemistry. 2007 Jun 23;71(6):1387–404. doi: 10.1271/bbb.70028.; Martens S, Mithöfer A. Flavones and flavone synthases. Phytochemistry. 2005 Oct;66(20):2399–407. doi: 10.1016/j.phytochem.2005.07.013. PMID: 16137727.; Vogt T, Jones P. Glycosyltransferases in plant natural product synthesis: characterization of a supergene family. Trends Plant Sci. 2000 Sep;5(9):380–6. doi: 10.1016/s1360-1385(00)01720-9. PMID: 10973093. |
| superpathway of flavones and derivatives biosynthesis Accession ID: PlantCyc:PLANT_PWY-6266 |
|
Han Y, Vimolmangkang S, Soria-Guerra RE, Rosales-Mendoza S, Zheng D, Lygin AV, Korban SS. Ectopic expression of apple F3'H genes contributes to anthocyanin accumulation in the Arabidopsis tt7 mutant grown under nitrogen stress. Plant Physiol. 2010 Jun;153(2):806–20. PMID: 20357139; PMCID: PMC2879788.; Masada S, Terasaka K, Oguchi Y, Okazaki S, Mizushima T, Mizukami H. Functional and structural characterization of a flavonoid glucoside 1,6-glucosyltransferase from Catharanthus roseus. Plant Cell Physiol. 2009 Aug;50(8):1401–15. doi: 10.1093/pcp/pcp088. PMID: 19561332.; Yonekura-Sakakibara K, Tohge T, Niida R, Saito K. Identification of a Flavonol 7-O-Rhamnosyltransferase Gene Determining Flavonoid Pattern in Arabidopsis by Transcriptome Coexpression Analysis and Reverse Genetics. Journal of Biological Chemistry. 2007 May;282(20):14932–41. doi: 10.1074/jbc.m611498200.; Jones P, Messner B, Nakajima J, Schäffner AR, Saito K. UGT73C6 and UGT78D1, Glycosyltransferases Involved in Flavonol Glycoside Biosynthesis in Arabidopsis thaliana. Journal of Biological Chemistry. 2003 Nov;278(45):43910–8. doi: 10.1074/jbc.m303523200.; Cacace S, Schröder G, Wehinger E, Strack D, Schmidt J, Schröder J. A flavonol O-methyltransferase from Catharanthus roseus performing two sequential methylations. Phytochemistry. 2003 Jan;62(2):127–37. doi: 10.1016/s0031-9422(02)00483-1. PMID: 12482447.; Gauthier A, Gulick PJ, Ibrahim RK. Characterization of Two cDNA Clones Which EncodeO-Methyltransferases for the Methylation of both Flavonoid and Phenylpropanoid Compounds. Archives of Biochemistry and Biophysics. 1998 Mar;351(2):243–9. doi: 10.1006/abbi.1997.0554.; HAGMANN M, HELLER W, GRISEBACH H. Induction and Characterization of a Microsomal Flavonoid 3'-Hydroxylase from Parsley Cell Cultures. European Journal of Biochemistry. 1983 Aug;134(3):547–54. doi: 10.1111/j.1432-1033.1983.tb07601.x.; Jourdan PS, Mansell RL. Isolation and partial characterization of three glucosyl transferases involved in the biosynthesis of flavonol triglucosides in Pisum sativum L. Archives of Biochemistry and Biophysics. 1982 Feb;213(2):434–43. doi: 10.1016/0003-9861(82)90569-0. |