Functional moiety for the antifungal activity of phytocassane E, a diterpene phytoalexin from rice

Koga, Jinichiro; Ogawa, Naoko; Yamauchi, Toyozo; Kikuchi, Minako; Ogasawara, Nagahiro; Shimura, Masaru

doi:10.1016/s0031-9422(96)00534-1

Cited by 106 publications

(92 citation statements)

References 13 publications

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“…It was found that the content of M A in rice is higher than M B (Lee et al 1999, Chung et al 2005). Many scientists have attempted to isolate and characterize phytoalexins from rice plants, of which oryzalexins A-D, phytocassanes A-D and EL (Kono et al 1984, Sekido et al 1986, Koga et al 1997, and they are considered as novel antifungal diterpene compounds. A flavanone phytoalexin, sakuranetin that was isolated from ultraviolet irradiated rice leaves, showed great inhibition on spore germination of Pyricularia oryzae with the value of ED 50 (Effective Dose) of about 15 ppm (Kodama et al 1992).…”

Section: Discussionmentioning

confidence: 99%

“…For example, the diterpene pisiferic acid from leaves and twigs of Chamaecyparis pisifera (Cupressaceae) displayed strong antifungal activity against the rice pathogen Pyricularia oryzae (Kobayashi et al 1987). Koga et al (1997) opined that the hydroxyl group at the C-1 position was the main functional moiety of the high fungicidal activity of the phytocassane E from rice leaves. Momilactones are oxygenated derivatives of 9bH-pirama-7,15-diene-19,6-b-olide and oryzalexins are oxygenated derivatives of a sterically different pimaradiene, ent-sandaracopimara 8, 15-diene (Kono et al 1984, Kodama et al 1988.…”

Section: Discussionmentioning

confidence: 99%

“…Terpenoids, phenolics and nitrogen-containing compounds are the major groups of secondary metabolites, which recently have been extensively studied and reported as plant defense systems against herbivores and pathogens, and which act as plant growth inhibitor substances (Taiz & Zeiger 2002). When plants interact with pathogens, they can protect themselves by accumulating antimicrobial compounds induced phytoalexins (Koga et al 1997). Phytoalexins are low-molecular-weight substances that act as part of the plant defense system.…”

Section: Introductionmentioning

confidence: 99%

“…A large number of phytotoxic substances (allelochemicals) including diterpene and flavanone phytoalexins, which are involved in the defense mechanism of the rice plant have been isolated as phytoalexins such as M A and M B (Figure 1), oryzalexin A-F, phytocassanes A to D and the flavonoid phytoalexin sakuranetin (Cartwright et al 1977, Kodama et al 1992, Kato et al 1993, Tamogani et al 1993, Koga et al 1997, Chung et al 2005. The diterpenoids (M A and M B ) were first isolated by Japanese scientists from rice husks (Kato et al 1973) and indicated by them as potential plant growth inhibitors.…”

Section: Introductionmentioning

confidence: 99%

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Comparative efficaciesin vitroof antibacterial, fungicidal, antioxidant, and herbicidal activities of momilatones A and B

Fukuta¹,

Xuan²,

Deba³

et al. 2007

Journal of Plant Interactions

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Momilactones A (M A ) and B (M B ) are phytoalexins derived from rice plant (Oryza sativa) and were considered to be a part of the mechanism of rice self-defense system. The present study was to evaluate the comparative efficacies in vitro of antibacterial, fungicidal, antioxidant, and herbicidal activities of M A and M B . In general, M B shows higher antifungal, antibacterial, and herbicidal action than M A , although its antioxidant property was less than M A . In herbicidal trial, the IC 50 values of M B against germination, shoot and root elongation of barnyardgrass and monochoria were 40.9, 45.5, and 27.5, and 27.1, 17.3, and 0.9 mg, respectively. For M A , these values were 40.3, 35.6, and 55.1, and 43.9, 24.3, and 0.5 mg, respectively. For antifungal activity, momilactone B (IC 50 : 1.2, 123.9, and 53.4 mg) exerted significantly greater inhibition than M A (IC 50 : 78.1, 198.1, and 95.3 mg) against Botrytis cinerea, Fusarium solani, Colletrotrichum gloeosporioides, respectively, except for Fusarium oxysporum that both M A and M B showed no marked difference. In addition, M B exhibited significantly stronger antibacterial activity than M A against Pseudomonus ovalis, Bacillus cereus, and Bacillus pumilus, whereas the inhibitory activity of the two compounds was similar against Escherichia coli. Both M A and M B exerted rather weak antioxidant activity (EC 50 was 783.9 and 790.7 mg, respectively), of which M A showed a slightly stronger antioxidant activity than M B . This study is the first to examine antifungal, antibacterial, and antioxidant activities of two phytoalexins, as well as their comparative efficacies against growth of the noxious weeds barnyardgrass and monochoria.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Comparative efficaciesin vitroof antibacterial, fungicidal, antioxidant, and herbicidal activities of momilatones A and B

Fukuta¹,

Xuan²,

Deba³

et al. 2007

Journal of Plant Interactions

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“…Four structurally distinct types of polycyclic diterpenoid phytoalexins, oryzalexins A-F [3][4][5], ())-phytocassanes A-E [6][7][8], momilactones A and B [9,10], and oryzalexin S [11], have been identified in extracts of the leaves of rice plants that were either infected with the rice leaf blast pathogen, Magnaporthe grisea, or exposed to ultra-violet (UV)-irradiation. The proposed pathways for biosynthesis of diterpenoid phytoalexins in rice are illustrated in Fig.…”

Section: Introductionmentioning

confidence: 99%

Stemar‐13‐ene synthase, a diterpene cyclase involved in the biosynthesis of the phytoalexin oryzalexin S in rice

et al. 2004

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In suspension-cultured rice cells, diterpenoid phytoalexins are produced in response to exogenously applied elicitors. We isolated a cDNA encoding a diterpene cyclase, OsDTC2, from suspension-cultured rice cells treated with a chitin elicitor. The OsDTC2 cDNA was overexpressed in Escherichia coli as a fusion protein with glutathione S-transferase, and the recombinant OsDTC2 was indicated to function as stemar-13-ene synthase that converted syn-copalyl diphosphate to stemar-13-ene, a putative diterpene hydrocarbon precursor of the phytoalexin oryzalexin S. The level of OsDTC2 mRNA in suspension-cultured rice cells began to increase 3 h after addition of the elicitor and reached the maximum after 8 h. The expression of OsDTC2 was also induced in UV-irradiated rice leaves. In addition, we indicated that stemar-13-ene accumulated in the chitin-elicited suspension-cultured rice cells and the UVirradiated rice leaves.

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Synthesis and Absolute Configuration of (−)-Phytocassane D, a Diterpene Phytoalexin Isolated from the Rice Plant,Oryza sativa

Yajima

Mori

2000

Eur. J. Org. Chem.

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To determine the absolute configuration of the phytocassane group of phytoalexins, the naturally occurring (−)‐phytocassane D was synthesized from the (R)‐Wieland−Miescher ketone, in an approach based on the preliminary model synthesis of the unnatural (+)‐2‐deoxyphytocassane A. By comparison of their CD spectra with those of synthetic phytocassanes of known absolute configuration, phytocassanes A−E were shown to possess the ent‐cassane skeleton.

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Functional moiety for the antifungal activity of phytocassane E, a diterpene phytoalexin from rice

Cited by 106 publications

References 13 publications

Comparative efficaciesin vitroof antibacterial, fungicidal, antioxidant, and herbicidal activities of momilatones A and B

Comparative efficaciesin vitroof antibacterial, fungicidal, antioxidant, and herbicidal activities of momilatones A and B

Stemar‐13‐ene synthase, a diterpene cyclase involved in the biosynthesis of the phytoalexin oryzalexin S in rice

Synthesis and Absolute Configuration of (−)-Phytocassane D, a Diterpene Phytoalexin Isolated from the Rice Plant,Oryza sativa

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