메뉴 건너뛰기




Volumn 63, Issue 16, 2015, Pages 4050-4059

Identification of UV-induced diterpenes including a new diterpene phytoalexin, phytocassane F, from rice leaves by complementary GC/MS and LC/MS approaches

Author keywords

Magnaporthe oryzae; mass spectrometry; phytoalexin; phytocassane; rice; ultraviolet irradiation

Indexed keywords

CHROMATOGRAPHIC ANALYSIS; MASS SPECTROMETRY; MICROORGANISMS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS;

EID: 84928717608     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.5b00785     Document Type: Article
Times cited : (44)

References (42)
  • 2
    • 84954897321 scopus 로고
    • Novel phytoalexins (oryzalexins A, B and C) isolated from rice blast leaves infected with Pyricularia oryzae. Part I: isolation, characterization and biological activities of oryzalexins
    • Akatsuka, T.; Kodama, O.; Sekido, H.; Kono, Y.; Takeuchi, S. Novel phytoalexins (oryzalexins A, B and C) isolated from rice blast leaves infected with Pyricularia oryzae. Part I: isolation, characterization and biological activities of oryzalexins Agric. Biol. Chem. 1985, 49, 1689-1694 10.1271/bbb1961.49.1689
    • (1985) Agric. Biol. Chem. , vol.49 , pp. 1689-1694
    • Akatsuka, T.1    Kodama, O.2    Sekido, H.3    Kono, Y.4    Takeuchi, S.5
  • 3
    • 85004366711 scopus 로고
    • Oryzalexin D 3,7-dihydroxy-(+)-sandaracopimaradiene), a new phytoalexin isolated from blast-infected rice leaves
    • Sekido, H.; Endo, T.; Suga, R.; Kodama, O.; Akatsuka, T.; Kono, Y.; Takeuchi, S. Oryzalexin D 3,7-dihydroxy-(+)-sandaracopimaradiene), a new phytoalexin isolated from blast-infected rice leaves J. Pestic. Sci. (Tokyo, Jpn.) 1986, 11, 369-372 10.1584/jpestics.11.369
    • (1986) J. Pestic. Sci. (Tokyo, Jpn.) , vol.11 , pp. 369-372
    • Sekido, H.1    Endo, T.2    Suga, R.3    Kodama, O.4    Akatsuka, T.5    Kono, Y.6    Takeuchi, S.7
  • 4
    • 0001861641 scopus 로고
    • Oryzalexin E, a diterpene phytoalexin from UV-irradiated rice leaves
    • Kato, H.; Kodama, O.; Akatsuka, T. Oryzalexin E, a diterpene phytoalexin from UV-irradiated rice leaves Phytochemistry 1993, 33, 79-81 10.1016/0031-9422(93)85399-C
    • (1993) Phytochemistry , vol.33 , pp. 79-81
    • Kato, H.1    Kodama, O.2    Akatsuka, T.3
  • 5
    • 0028130916 scopus 로고
    • Oryzalexin F, a diterpene phytoalexin from UV-irradiated rice leaves
    • Kato, H.; Kodama, O.; Akatsuka, T. Oryzalexin F, a diterpene phytoalexin from UV-irradiated rice leaves Phytochemistry 1994, 36, 299-301 10.1016/S0031-9422(00)97064-X
    • (1994) Phytochemistry , vol.36 , pp. 299-301
    • Kato, H.1    Kodama, O.2    Akatsuka, T.3
  • 6
    • 84950817655 scopus 로고
    • Oryzalexin S, a novel stemarane-type diterpene rice phytoalexin
    • Kodama, O.; Li, W. X.; Tamogami, S.; Akatsuka, T. Oryzalexin S, a novel stemarane-type diterpene rice phytoalexin Biosci., Biotechnol., Biochem. 1992, 56, 1002-1003 10.1271/bbb.56.1002
    • (1992) Biosci., Biotechnol., Biochem. , vol.56 , pp. 1002-1003
    • Kodama, O.1    Li, W.X.2    Tamogami, S.3    Akatsuka, T.4
  • 7
    • 0029053604 scopus 로고
    • Phytocassanes A, B, C and D, novel diterpene phytoalexins from rice, Oryza sativa L
    • Koga, J.; Shimura, M.; Oshima, K.; Ogawa, N.; Yamauchi, T.; Ogasawara, N. Phytocassanes A, B, C and D, novel diterpene phytoalexins from rice, Oryza sativa L Tetrahedron 1995, 51, 7907-7918 10.1016/0040-4020(95)00423-6
    • (1995) Tetrahedron , vol.51 , pp. 7907-7918
    • Koga, J.1    Shimura, M.2    Oshima, K.3    Ogawa, N.4    Yamauchi, T.5    Ogasawara, N.6
  • 8
    • 0031038405 scopus 로고    scopus 로고
    • Functional moiety for the antifungal activity of phytocassane E, a diterpene phytoalexin from rice
    • Koga, J.; Ogawa, N.; Yamauchi, T.; Kikuchi, M.; Ogasawara, N.; Shimura, M. Functional moiety for the antifungal activity of phytocassane E, a diterpene phytoalexin from rice Phytochemistry 1997, 44, 249-253 10.1016/S0031-9422(96)00534-1
    • (1997) Phytochemistry , vol.44 , pp. 249-253
    • Koga, J.1    Ogawa, N.2    Yamauchi, T.3    Kikuchi, M.4    Ogasawara, N.5    Shimura, M.6
  • 9
    • 84878774288 scopus 로고    scopus 로고
    • Identification of a novel casbane-type diterpene phytoalexin, ent -10-oxodepressin, from rice leaves
    • Inoue, Y.; Sakai, M.; Yao, Q.; Tanimoto, Y.; Toshima, H.; Hasegawa, M. Identification of a novel casbane-type diterpene phytoalexin, ent -10-oxodepressin, from rice leaves Biosci., Biotechnol., Biochem. 2013, 77, 760-765 10.1271/bbb.120891
    • (2013) Biosci., Biotechnol., Biochem. , vol.77 , pp. 760-765
    • Inoue, Y.1    Sakai, M.2    Yao, Q.3    Tanimoto, Y.4    Toshima, H.5    Hasegawa, M.6
  • 10
    • 44049121001 scopus 로고
    • Sakuranetin, a flavanone phytoalexin from ultraviolet-irradiated rice leaves
    • Kodama, O.; Miyakawa, J.; Akatsuka, T.; Kiyosawa, S. Sakuranetin, a flavanone phytoalexin from ultraviolet-irradiated rice leaves Phytochemistry 1992, 31, 3807-3809 10.1016/S0031-9422(00)97532-0
    • (1992) Phytochemistry , vol.31 , pp. 3807-3809
    • Kodama, O.1    Miyakawa, J.2    Akatsuka, T.3    Kiyosawa, S.4
  • 11
    • 0000559004 scopus 로고
    • Isolation and characterization of two phytoalexins from rice as momilactones A and B
    • Cartwright, D. W.; Langcake, P.; Pryce, R. J.; Leworthy, D. P.; Ride, J. P. Isolation and characterization of two phytoalexins from rice as momilactones A and B Phytochemistry 1981, 20, 535-537 10.1016/S0031-9422(00)84189-8
    • (1981) Phytochemistry , vol.20 , pp. 535-537
    • Cartwright, D.W.1    Langcake, P.2    Pryce, R.J.3    Leworthy, D.P.4    Ride, J.P.5
  • 13
    • 84906662011 scopus 로고    scopus 로고
    • Analysis on blast fungus-responsive characters of a flavonoid phytoalexin sakuranetin; accumulation in infected rice leaves, antifungal activity and detoxification by fungus
    • Hasegawa, M.; Mitsuhara, I.; Seo, S.; Okada, K.; Yamane, H.; Iwai, T.; Ohashi, Y. Analysis on blast fungus-responsive characters of a flavonoid phytoalexin sakuranetin; accumulation in infected rice leaves, antifungal activity and detoxification by fungus Molecules 2014, 19, 11404-11418 10.3390/molecules190811404
    • (2014) Molecules , vol.19 , pp. 11404-11418
    • Hasegawa, M.1    Mitsuhara, I.2    Seo, S.3    Okada, K.4    Yamane, H.5    Iwai, T.6    Ohashi, Y.7
  • 15
    • 33749512596 scopus 로고    scopus 로고
    • Uncovering the complex metabolic network underlying diterpenoid phytoalexin biosynthesis in rice and other cereal crop plants
    • Peters, R. J. Uncovering the complex metabolic network underlying diterpenoid phytoalexin biosynthesis in rice and other cereal crop plants Phytochemistry 2006, 67, 2307-2317 10.1016/j.phytochem.2006.08.009
    • (2006) Phytochemistry , vol.67 , pp. 2307-2317
    • Peters, R.J.1
  • 16
    • 45849132076 scopus 로고    scopus 로고
    • Recent advances regarding diterpene cyclase genes in higher plants and fungi
    • Toyomasu, T. Recent advances regarding diterpene cyclase genes in higher plants and fungi Biosci., Biotechnol., Biochem. 2008, 72, 1168-1175 10.1271/bbb.80044
    • (2008) Biosci., Biotechnol., Biochem. , vol.72 , pp. 1168-1175
    • Toyomasu, T.1
  • 17
    • 84880175153 scopus 로고    scopus 로고
    • Biosynthesis of phytoalexins and regulatory mechanisms of it in rice
    • Yamane, H. Biosynthesis of phytoalexins and regulatory mechanisms of it in rice Biosci., Biotechnol., Biochem. 2013, 77, 1141-1148 10.1271/bbb.130109
    • (2013) Biosci., Biotechnol., Biochem. , vol.77 , pp. 1141-1148
    • Yamane, H.1
  • 18
    • 0029951087 scopus 로고    scopus 로고
    • Biosynthesis of cyclic diterpene hydrocarbons in rice cell suspensions: conversion of 9,10- syn -labda-8(17),13-dienyl diphosphate to 9β-pimara-7,15-diene and stemar-13-ene
    • Mohan, R. S.; Yee, N. K. N.; Coates, R. M.; Ren, Y.-Y.; Stamenkovic, P.; Mendez, I.; West, C. A. Biosynthesis of cyclic diterpene hydrocarbons in rice cell suspensions: conversion of 9,10- syn -labda-8(17),13-dienyl diphosphate to 9β-pimara-7,15-diene and stemar-13-ene Arch. Biochem. Biophys. 1996, 330, 33-47 10.1006/abbi.1996.0223
    • (1996) Arch. Biochem. Biophys. , vol.330 , pp. 33-47
    • Mohan, R.S.1    Yee, N.K.N.2    Coates, R.M.3    Ren, Y.-Y.4    Stamenkovic, P.5    Mendez, I.6    West, C.A.7
  • 20
    • 0028921666 scopus 로고
    • Characterization of an inducible P450 hydroxylase involved in the rice diterpene phytoalexin biosynthetic pathway
    • Kato, H.; Kodama, O.; Akatsuka, T. Characterization of an inducible P450 hydroxylase involved in the rice diterpene phytoalexin biosynthetic pathway Arch. Biochem. Biophys. 1995, 316, 707-712 10.1006/abbi.1995.1094
    • (1995) Arch. Biochem. Biophys. , vol.316 , pp. 707-712
    • Kato, H.1    Kodama, O.2    Akatsuka, T.3
  • 21
    • 0036490485 scopus 로고    scopus 로고
    • Biosynthesis of rice phytoalexin: enzymatic conversion of 3β-hydroxy-9β-pimara-7,15-dien-19,6β-olide to momilactone A
    • Atawong, A.; Hasegawa, M.; Kodama, O. Biosynthesis of rice phytoalexin: enzymatic conversion of 3β-hydroxy-9β-pimara-7,15-dien-19,6β-olide to momilactone A Biosci., Biotechnol., Biochem. 2002, 66, 566-570 10.1271/bbb.66.566
    • (2002) Biosci., Biotechnol., Biochem. , vol.66 , pp. 566-570
    • Atawong, A.1    Hasegawa, M.2    Kodama, O.3
  • 22
    • 0030755607 scopus 로고    scopus 로고
    • Phytoalexin production elicited by exogenously applied jasmonic acid in rice leaves (Oryza sativa L.) is under the control of cytokinins and ascorbic acid
    • Tamogami, S.; Rakwal, R.; Kodama, O. Phytoalexin production elicited by exogenously applied jasmonic acid in rice leaves (Oryza sativa L.) is under the control of cytokinins and ascorbic acid FEBS Lett. 1997, 412, 61-64 10.1016/S0014-5793(97)00743-6
    • (1997) FEBS Lett. , vol.412 , pp. 61-64
    • Tamogami, S.1    Rakwal, R.2    Kodama, O.3
  • 26
    • 0000058940 scopus 로고
    • Ultraviolet-induced accumulation of phytoalexins in rice leaves
    • Kodama, O.; Suzuki, T.; Miyakawa, J.; Akatsuka, T. Ultraviolet-induced accumulation of phytoalexins in rice leaves Agric. Biol. Chem. 1988, 52, 2469-2473 10.1271/bbb1961.52.2469
    • (1988) Agric. Biol. Chem. , vol.52 , pp. 2469-2473
    • Kodama, O.1    Suzuki, T.2    Miyakawa, J.3    Akatsuka, T.4
  • 27
    • 0029767548 scopus 로고    scopus 로고
    • Synthesis of 7-methoxyapigeninidin and its fungicidal activity against Gloeocercospora sorghi
    • Aida, Y.; Tamogami, S.; Kodama, O.; Tsukiboshi, T. Synthesis of 7-methoxyapigeninidin and its fungicidal activity against Gloeocercospora sorghi Biosci., Biotechnol., Biochem. 1996, 60, 1495-1496 10.1271/bbb.60.1495
    • (1996) Biosci., Biotechnol., Biochem. , vol.60 , pp. 1495-1496
    • Aida, Y.1    Tamogami, S.2    Kodama, O.3    Tsukiboshi, T.4
  • 29
    • 0042703231 scopus 로고    scopus 로고
    • Induced volatiles in elicitor-treated and rice blast fungus-inoculated rice leaves
    • Obara, N.; Hasegawa, M.; Kodama, O. Induced volatiles in elicitor-treated and rice blast fungus-inoculated rice leaves Biosci., Biotechnol., Biochem. 2002, 66, 2549-2559 10.1271/bbb.66.2549
    • (2002) Biosci., Biotechnol., Biochem. , vol.66 , pp. 2549-2559
    • Obara, N.1    Hasegawa, M.2    Kodama, O.3
  • 31
    • 0027480743 scopus 로고
    • Oryzalexin S structure: a new stemarane-type rice plant phytoalexin and its biogenesis
    • Tamogami, S.; Mitani, M.; Kodama, O.; Akatsuka, T. Oryzalexin S structure: a new stemarane-type rice plant phytoalexin and its biogenesis Tetrahedron 1993, 49, 2025-2032 10.1016/S0040-4020(01)86302-X
    • (1993) Tetrahedron , vol.49 , pp. 2025-2032
    • Tamogami, S.1    Mitani, M.2    Kodama, O.3    Akatsuka, T.4
  • 32
    • 84870180449 scopus 로고    scopus 로고
    • Regio- and diastereoselective synthesis and X-ray structure determination of (+)-2-deoxyoryzalexin S from (+)-podocarpic acid. Structural nonidentity with its nominal natural isolated enantiomer
    • Leonelli, F.; Latini, V.; Trombetta, A.; Bartoli, G.; Ceccacci, F.; La Bella, A.; Sferrazza, A.; Lamba, D.; Migneco, L. M.; Bettolo, R. M. Regio- and diastereoselective synthesis and X-ray structure determination of (+)-2-deoxyoryzalexin S from (+)-podocarpic acid. Structural nonidentity with its nominal natural isolated enantiomer J. Nat. Prod. 2012, 75, 1944-1950 10.1021/np300518j
    • (2012) J. Nat. Prod. , vol.75 , pp. 1944-1950
    • Leonelli, F.1    Latini, V.2    Trombetta, A.3    Bartoli, G.4    Ceccacci, F.5    La Bella, A.6    Sferrazza, A.7    Lamba, D.8    Migneco, L.M.9    Bettolo, R.M.10
  • 34
    • 0001000849 scopus 로고
    • Diterpenes from Calceolaria latifolia
    • Garbarino, J. A.; Molinari, A. Diterpenes from Calceolaria latifolia Phytochemistry 1990, 29, 3037-3039 10.1016/0031-9422(90)87134-G
    • (1990) Phytochemistry , vol.29 , pp. 3037-3039
    • Garbarino, J.A.1    Molinari, A.2
  • 36
    • 84865267973 scopus 로고    scopus 로고
    • The potential of Cyathus africanus for transformation of terpene substrates
    • McCook, K. P.; Chen, A. R. M.; Reynolds, W. F.; Reese, P. B. The potential of Cyathus africanus for transformation of terpene substrates Phytochemistry 2012, 82, 61-66 10.1016/j.phytochem.2012.06.018
    • (2012) Phytochemistry , vol.82 , pp. 61-66
    • Mccook, K.P.1    Chen, A.R.M.2    Reynolds, W.F.3    Reese, P.B.4
  • 37
    • 0034650864 scopus 로고    scopus 로고
    • Absolute configuration of phytocassanes as proposed on the basis of the CD spectrum of synthetic (+)-2-deoxyphytocassane A
    • Yajima, A.; Mori, K. Absolute configuration of phytocassanes as proposed on the basis of the CD spectrum of synthetic (+)-2-deoxyphytocassane A Tetrahedron Lett. 2000, 41, 351-354 10.1016/S0040-4039(99)02060-2
    • (2000) Tetrahedron Lett. , vol.41 , pp. 351-354
    • Yajima, A.1    Mori, K.2
  • 38
    • 84896512733 scopus 로고    scopus 로고
    • Isolation of jasmonate-induced sesquiterpene synthase of rice: product of which has an antifungal activity against Magnaporthe oryzae
    • Taniguchi, S.; Miyoshi, S.; Tamaoki, D.; Yamada, S.; Tanaka, K.; Uji, Y.; Tanaka, S.; Akimitsu, K.; Gomi, K. Isolation of jasmonate-induced sesquiterpene synthase of rice: product of which has an antifungal activity against Magnaporthe oryzae J. Plant Physiol. 2014, 171, 625-632 10.1016/j.jplph.2014.01.007
    • (2014) J. Plant Physiol. , vol.171 , pp. 625-632
    • Taniguchi, S.1    Miyoshi, S.2    Tamaoki, D.3    Yamada, S.4    Tanaka, K.5    Uji, Y.6    Tanaka, S.7    Akimitsu, K.8    Gomi, K.9
  • 40
    • 42549090923 scopus 로고    scopus 로고
    • The tryptophan pathway is involved in the defense responses of rice against pathogenic infection via serotonin production
    • Ishihara, A.; Hashimoto, Y.; Tanaka, C.; Dubouzet, J. G.; Nakao, T.; Matsuda, F.; Nishioka, T.; Miyagawa, H.; Wakasa, K. The tryptophan pathway is involved in the defense responses of rice against pathogenic infection via serotonin production Plant J. 2008, 54, 481-495 10.1111/j.1365-313X.2008.03441.x
    • (2008) Plant J. , vol.54 , pp. 481-495
    • Ishihara, A.1    Hashimoto, Y.2    Tanaka, C.3    Dubouzet, J.G.4    Nakao, T.5    Matsuda, F.6    Nishioka, T.7    Miyagawa, H.8    Wakasa, K.9
  • 41
    • 84911938062 scopus 로고    scopus 로고
    • Antimicrobial activity of UV-induced phenylamides from rice leaves
    • Park, H. L.; Yoo, Y.; Hahn, T.-R.; Bhoo, S. H.; Lee, S.-W.; Cho, M.-H. Antimicrobial activity of UV-induced phenylamides from rice leaves Molecules 2014, 19, 18139-18151 10.3390/molecules191118139
    • (2014) Molecules , vol.19 , pp. 18139-18151
    • Park, H.L.1    Yoo, Y.2    Hahn, T.-R.3    Bhoo, S.H.4    Lee, S.-W.5    Cho, M.-H.6
  • 42
    • 84857858640 scopus 로고    scopus 로고
    • Identification of a degradation intermediate of the momilactone A rice phytoalexin by the rice blast fungus
    • Imai, T.; Ohashi, Y.; Mitsuhara, I.; Seo, S.; Toshima, H.; Hasegawa, M. Identification of a degradation intermediate of the momilactone A rice phytoalexin by the rice blast fungus Biosci., Biotechnol., Biochem. 2012, 76, 414-416 10.1271/bbb.110756
    • (2012) Biosci., Biotechnol., Biochem. , vol.76 , pp. 414-416
    • Imai, T.1    Ohashi, Y.2    Mitsuhara, I.3    Seo, S.4    Toshima, H.5    Hasegawa, M.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.