Isolation and identification of a potent allelopathic substance in rice root exudates

Kato‐Noguchi, Hisashi; Ino, Takeshi; Sata, Noriko; Yamamura, Shosuke

doi:10.1034/j.1399-3054.2002.1150310.x

Cited by 138 publications

(120 citation statements)

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“…19) It has been found that momilactone B is excluded from rice roots and exhibits allelopathic activity against the growth of dicot plant seedlings. 5) We found that phytocassanes A to E and momilactones A and B are released from roots. 37) In contrast to momilactone B, phytocassanes do not show inhibitory activity against dicot seedling growth.…”

Section: Labdane-related Diterpene Cyclase Gene Family In Ricementioning

confidence: 78%

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Recent Advances Regarding Diterpene Cyclase Genes in Higher Plants and Fungi

Toyomasu

2008

Bioscience, Biotechnology, and Biochemistry

100

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Cyclic diterpenoids are commonly biosynthesized from geranylgeranyl diphosphate (GGDP) through the formation of carbon skeletons by specific cyclases and subsequent chemical modifications, such as oxidation, reduction, methylation, and glucosidation. A variety of diterpenoids are produced in higher plants and fungi. Rice produces four classes of diterpene phytoalexins, phytocassanes A to E, oryzalexins A to F, oryzalexin S, and momilactones A and B. The six diterpene cyclase genes involved in the biosynthesis of these phytoalexins were identified and characterized. Fusicoccin A was produced by the phytopathogenic Phomopsis amygdali and served as a plant H þ -ATPase activator. A PaFS, encoding a fungal diterpene synthase responsible for fusicoccin biosynthesis, was isolated. The PaFS is an unusual chimeric diterpene synthase that possesses not only terpene cyclase activity (the formation of fusicoccadiene, a biosynthetic precursor of fusicoccin A), but also prenyltransferase activity (the formation of GGDP). Thus, we identified a unique multifunctional diterpene synthase family in fungi.

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Section: Labdane-related Diterpene Cyclase Gene Family In Ricementioning

confidence: 78%

“…For example, gibberellins (GAs, phytohormone), 2) momilactones (phytoalexin; allelopathic substance, Fig. 1), [3][4][5] oryzalexins (phytoalexin, Fig. 1), [6][7][8][9] and phytocassanes (phytoalexin, Fig.…”

mentioning

confidence: 99%

Recent Advances Regarding Diterpene Cyclase Genes in Higher Plants and Fungi

Toyomasu

2008

Bioscience, Biotechnology, and Biochemistry

100

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“…[5][6][7] Rice plants were also found to secrete momilactone A and B from their roots into the rhizosphere and exhibit alleloapthic activities against weed plants. 1,[8][9][10] The plant rhizosphere is a densely populated area in which plant roots must compete with invading root systems of neighboring plants for space, water and mineral nutrients, and with other soil-bore organisms including bacteria and fungi. [11][12][13][14] Therefore, momilactone A and B probably play an important role in rice defense mechanism in the rhizosphere as antimicrobial and allelopathic agents.…”

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confidence: 99%

Secretion of momilactone A and B by the mossHypnum plumaeforme

Kato‐Noguchi¹

2009

Plant Signaling & Behavior

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Although rice and the moss Hypnum plumaeforme Wils are taxonomically quite distinct, momilactone A and B have so far been found only in rice and H. plumaeforme. 1-4 Momilactone A and B in rice plants are known to be synthesized as a part of defensive responses and exhibit antibacterial and antifungal activities. 5-7 Rice plants were also found to secrete momilactone A and B from their roots into the rhizosphere and exhibit alleloapthic activities against weed plants. 1,[8][9][10] The plant rhizosphere is a densely populated area in which plant roots must compete with invading root systems of neighboring plants for space, water and mineral nutrients, and with other soil-bore organisms including bacteria and fungi. [11][12][13][14] Therefore, momilactone A and B probably play an important role in rice defense mechanism in the rhizosphere as antimicrobial and allelopathic agents. However, it has not clear that biological meanings of momilactone A and B in H. plumaeforme. H. plumaeforme is often dominative in plant communities and forms large pure colonies. 15,16 H. plumaeforme was grown on MS growth medium and the concentrations of momilactone A and B in the medium were determined as the secretion levels of momilactone A and B from H. plumaeforme. The secretion levels of momilactone A and B were 4.0 and 6.3 μg g -1 dry weight of H. plumaeforme, respectively (Table 1). The endogenous concentration of momilactone A and B in H. plumaeforme was 58.7 and 23.4 μg g -1 dry weight, respectively. 4 Thus, the secretion levels of momilactone A and B, respectively, were 6.8 and 27% of momilactone A and B concentrations in H. plumaeforme. Therefore, although the endogenous concentration of momilactone A in H. plumaeforme was greater than that of momilactone B, the secretion level of momilactone B was much greater than that of momilactone A, which suggests that momilactone B may be selectively secreted into the medium than momilactone A. In addition, biological activity of momilactone B was much greater than that of momilactone A. 10 H. plumaeforme was transplanted on MS growth medium and grown at 25°C with a 12-h photoperiod for 5 days as described previously. 4 During the incubation, additional UV-irradiation (80 min par day, UV, emission peak 253 nm; 10 μmol m -1 s -1 at plant level) was made. Momilactone A and B concentrations in the medium were then determined as the secretion levels by H. plumaeforme. For cantharidin-and jasmonic acid-treatments, H. plumaeforme was transplanted on MS growth medium containing 200 μM cantharidin or 100 μM jasmonic acid, and grown at 25°C with a 12-h photoperiod for 5 days. All manipulations were carried out under sterile conditions. Control plants were incubated MS growth medium for 5 days. Means ± SE from five independent experiments with five assays for each determination are shown.

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“…In addition, momilactones A and B also act as allelochemicals, as these were originally identified as dormancy factors from rice seed husks (Kato et al, 1973). More recently, momilactone B has been shown to be constitutively secreted from the roots of rice seedlings (Kato-Noguchi and Ino, 2003) as an allelopathic agent (Kato-Noguchi et al, 2002). Further, secretion of antimicrobial agents to the rhizosphere may also provide a competitive advantage for root establishment through local suppression of soil microorganisms (Bais et al, 2004).…”

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confidence: 99%

Identification of Syn-Pimara-7,15-Diene Synthase Reveals Functional Clustering of Terpene Synthases Involved in Rice Phytoalexin/Allelochemical Biosynthesis

et al. 2004

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Rice (Oryza sativa) produces momilactone diterpenoids as both phytoalexins and allelochemicals. Accordingly, the committed step in biosynthesis of these natural products is catalyzed by the class I terpene synthase that converts syn-copalyl diphosphate to the corresponding polycyclic hydrocarbon intermediate syn-pimara-7,15-diene. Here, a functional genomics approach was utilized to identify a syn-copalyl diphosphate specific 9b-pimara-7,15-diene synthase (OsDTS2). To our knowledge, this is the first identified terpene synthase with this particular substrate stereoselectivity and, by comparison with the previously described and closely related ent-copalyl diphosphate specific cassa-12,15-diene synthase (OsDTC1), provides a model system for investigating the enzymatic determinants underlying the observed difference in substrate specificity. Further, OsDTS2 mRNA in leaves is up-regulated by conditions that stimulate phytoalexin biosynthesis but is constitutively expressed in roots, where momilactones are constantly synthesized as allelochemicals. Therefore, transcription of OsDTS2 seems to be an important regulatory point for controlling production of these defensive compounds. Finally, the gene identified here as OsDTS2 has previously been mapped at 14.3 cM on chromosome 4. The class II terpene synthase producing syn-copalyl diphosphate from the universal diterpenoid precursor geranylgeranyl diphosphate was also mapped to this same region. These genes catalyze sequential cyclization steps in momilactone biosynthesis and seem to have been evolutionarily coupled by physical linkage and resulting cosegregation. Further, the observed correlation between physical proximity and common metabolic function indicates that other such class I and class II terpene synthase gene clusters may similarly catalyze consecutive reactions in shared biosynthetic pathways.Plants produce a vast and diverse array of low-molecular weight organic compounds, the overwhelming majority of which are secondary metabolites with nonessential, yet important, functions such as defense . For example, phytoalexins are produced in response to microbial infections and exhibit antimicrobial activity (VanEtten et al., 1994), while allelochemicals are secreted to the rhizosphere and suppress the growth of neighboring plants (Bais et al., 2004). Often found serving in such roles are terpenoids, which are particularly abundant in plant metabolism and form the largest class of natural products, exhibiting wide diversity in chemical structure and biological function . Much of the structural variation within this class arises from the diverse carbon backbones formed by terpene synthases (cyclases). These divalent metal dependent enzymes carry out complex electrophilic cyclizations/ rearrangements to create these diverse skeletal structures from relatively simple acyclic precursors (Davis and Croteau, 2000). Notably, production of a specific backbone structure either dictates, or at least severely restricts, the metabolic fate of that particular molecule. Thus,...

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Isolation and identification of a potent allelopathic substance in rice root exudates

Cited by 138 publications

References 21 publications

Recent Advances Regarding Diterpene Cyclase Genes in Higher Plants and Fungi

Recent Advances Regarding Diterpene Cyclase Genes in Higher Plants and Fungi

Secretion of momilactone A and B by the mossHypnum plumaeforme

Identification of Syn-Pimara-7,15-Diene Synthase Reveals Functional Clustering of Terpene Synthases Involved in Rice Phytoalexin/Allelochemical Biosynthesis

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