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We conducted an investigation to search for the possibility of phytotoxic compounds and then identify them in C. aciculatus. The aqueous methanol extracts of C. aciculatus imposed a strong suppressive effect on the shoots and roots growth of Medicago sativa and Echinochloa crus-galli. The C. aciculatus extracts were subsequently purified through chromatography and three growth-inhibitory compounds were identified by spectral data as methyl cis-p-coumarate, methyl trans-p-coumarate, and trans-ferulaldehyde. The seedlings growth of Lepidium sativum was suppressed by methyl cis-p-coumarate, methyl trans-p-coumarate, and trans-ferulaldehyde. The I50 values (concentration required for 50% growth inhibition) for the seedling growth of L. sativum ranged from 1.25 to 1.73 mM for methyl cis-p-coumarate, 0.74 to 1.23 mM for methyl trans-p-coumarate, and 1.05 to 1.84 mM for trans-ferulaldehyde. Our finding indicates that methyl cis-p-coumarate, methyl trans-p-coumarate, and trans-ferulaldehyde may contribute to the phytotoxic effects of C. aciculatus.

The fruits of Piper retrofractum Vahl. contain a variety of compounds, but no phytotoxic compound with plant growth inhibitory activity has been reported. Therefore, the phytotoxic activity of P. retrofractum fruit extracts was investigated and found the reduction of seedling growth of cress, lettuce, alfalfa, barnyard grass, Italian ryegrass, and jungle rice. Seven bioactive compounds were isolated from the fruit extracts and identified as 3-phenylpropanoic acid (1), (2E,4E)-methyl piperate (2), (2E,4Z)-methyl piperate (3), piperlonguminine (4), dihydropiperine (5), isochavicine (6), and piperine (7). There have been no reports for their phytotoxic activity. The activity of these compounds was determined against the germination and seedling growth of cress and barnyard grass. The total germination percentage (GP) of cress was significantly inhibited by 1, 2, and 6 (40–100% inhibition), while its germination index or progressive total of cumulative germination (GI) was the most sensitive to 1, leading to the longest time required for 50% germination (T50) at 57 h behind control. However, the seedling growth of cress was highly inhibited by 6 with I50 values of 11 µM. The compounds 1 and 5–7 showed significant inhibition on GP of barnyard grass by 55–47%, while 5 and 1 effectively reduced GI and extended T50 to 42–48 h behind control, and 7 showed the most growth inhibition with I50 values of 37 µM. The inhibitory effects of the seven compounds indicate the phytotoxic property of P. retrofractum fruits, which 1, 5–7 may be the main compounds responsible for the phytotoxicity.

Citronella grass (Cymbopogon nardus) is a perennial herb. Many researchers have studied the exploitation of the active compounds in this plant for medicinal purposes, but there have been no studies on its phytotoxic compounds. Therefore, we investigated the phytotoxic active compounds in the roots of C. nardus. A significant inhibition was observed on the germination of cress (Lepidium sativum L.), lettuce (Lactuca sativa L.), barnyard grass (Echinochloa crus-galli L.), and Italian ryegrass (Lolium multiflorum Lam.) by the aqueous methanol extract of C. nardus roots. The extract decreased the total germination percentage (GP) and germination index (GI, progressive total of daily cumulative germination), and extended the time required for 50% germination (T 50) of all test species. A phytotoxic compound of the extract was isolated and identified as N-octanoyl tyramine by spectral analysis. This compound showed the inhibition on the germination of cress and barnyard grass. The decline in GP, GI, and T 50 was observed at concentrations of 30–2000 μM of N-octanoyl tyramine. The compound also showed the significant inhibition on the growth of cress and barnyard grass seedlings at concentrations greater than 100 and 300 μM, respectively. This study suggests that C. nardus could produce phytotoxic compounds, and N-octanoyl tyramine may be responsible for its phytotoxic activity.

Tinospora tuberculata Beumee has been used widely as a folk medicine and several bioactive compounds have been isolated. However, no herbicidal compound has been reported in this species. Therefore, we investigated the presence of phytotoxins in T. tuberculata. The aqueous methanol extracts of T. tuberculata inhibited the growth of roots and shoots of cress (Lepidum sativum L.), lettuce (Lactuca sativa L.), timothy (Phleum pratense L.) and barnyard grass (Echinochloa crus-galli (L.) Beauv.). The extract was then purified by several chromatographic runs with monitoring the inhibitory activity and the main phytotoxic substance was isolated. The chemical structure of the compound was determined by spectral data as syringin (4-[(1E)-3-Hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenyl β-d-glucopyranoside). It inhibited the root and shoot growth of all test plant species at concentrations >10 µM. The concentrations required for 50 % inhibition of root and shoot growth of cress and lettuce ranged from 78.2 to 412 μM, and that of timothy and barnyard grass renged from 9.8 to 73.2 µM. Effectiveness of syringin on monocotyledonous (timothy and barnyard grass) plants was greater than that on dicotyledonous (cress and lettuce) plants. These results suggest that syringin may contribute to the allelopathic effect caused by the T. tuberculata extract.

A potent growth inhibitory substance was isolated from an aqueous methanol extract of cucumber (Cucumis sativus L. cv. Phung Tuong) plants and determined as (2S)-2,3-dihydro-2α-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-(1,2,3-trihydroxypropyl)benzofuran-3β-methanol (sisymbrifolin) by spectral data. Sisymbrifolin inhibited the growth of cress (Lepidium sativum) and Echinochloa crus-galli seedlings at concentrations greater than 3 μM. Concentration of sisymbrifolin in the cucumber plants was the greatest among four growth inhibitory substances, (S)-2-benzoyloxy-3-phenyl-1-propanol, 9-hydroxy-4,7-megastigmadien-9-one, (6S,7E,9S)-6,9,10-trihydroxy-4,7-megastigmadien-3-one, and sisymbrifolin found in the cucumber, whereas growth inhibitory activity of 9-hydroxy-4,7-megastigmadien-9-one against cress and E. crus-galli was the greatest. Total activities of these substances (concentration of the substance/concentration required 50 % growth inhibition) were 14.4, 13.2, 8.5 and 10.7 for (S)-2-benzoyloxy-3-phenyl-1-propanol, 9-hydroxy-4,7-megastigmadien-9-one, (6S,7E,9S)-6,9,10-trihydroxy-4,7-megastigmadien-3-one and sisymbrifolin, respectively. These total activities were about 100-fold greater than those of phenolic acids, which are often mentioned as putative allelochemicals of plants. Thus, these substances may play important roles in the allelopathy of cucumber plants through the growth inhibition of neighboring plant species.

There is a rotational cropping system of wheat and rice in many areas. Wheat plants contain significant amounts of glucopyranosides of 6-methoxy-benzoxazolin-2(3H)-one (MBOA) and benzoxazolin-2(3H)-one (BOA). After crop harvesting, MBOA and BOA are produced during the degradation process of wheat residues left in the field. The purpose of this study was evaluation for the effect of MBOA and BOA on rice growth and germination. MBOA and BOA significantly inhibited the rice germination and the rice shoot growth at concentrations of 0.1 and 0.3 mM and higher, respectively. MBOA and BOA also inhibited the induction of α-amylase in rice seeds significantly at concentrations of 0.03 and 0.1 mM and higher, respectively, and inhibited gibberellin-induced α-amylase activity in de-embryonated rice. Significant inhibitions in germination, growth, and α-amylase activity were observed as MBOA and BOA concentrations increased. The inhibitions on the germination, growth, and α-amylase by MBOA were greater than those by BOA, which is the demethoxylated analogue of MBOA. These results suggest that MBOA and BOA may inhibit the germination and subsequent seedling growth of rice by inhibiting the gibberellin-induced α-amylase production. Therefore, wheat straw and roots left in the field after crop harvesting may suppress rice germination and growth, because of MBOA and BOA in the soil originated from wheat residues. Further studies are necessary for the determination of MBOA and BOA levels in field condition after the crop harvesting.

Although Plantago major and Plantago asiatica have similar life-history characteristics, P. major populations expand much more rapidly than P. asiatica in habitats where both species occur. One potential factor contributing to this disparity is the production of phytotoxic compounds. However, the phytotoxic characteristics of P. major and P. asiatica have not yet reported. Therefore, we conducted an investigation of possible phytotoxic compounds with allelopathic activity in both species. Aqueous methanol extracts of both plant species inhibited root and hypocotyl growth of garden cress (Lepidium sativum) in a concentration dependent manner. However, the inhibitory effect of P. major was greater than that of P. asiatica. The extracts were further purified by several chromatographic runs and two main phytotoxic compounds were isolated and identified through spectral analysis as (−)-3-hydroxy-β-ionone and blumenol A. (−)-3-Hydroxy-β-ionone and blumenol A inhibited the growth and germination of garden cress at concentrations greater than 1 and 30 μM, respectively. The level of (−)-3-hydroxy-β-ionone in P. major was 7.2-fold greater than that in P. asiatica, while the level of blumenol A was equal in both plant species. Although these Plantago species produce two main phytotoxic compounds with allelopathic activity, the higher level of (−)-3-hydroxy-β-ionone in P. major may result in it contributing the primary inhibitory effects of the extract of P. major. (−)-3-hydroxy-β-ionone may also serve to distinguish the invasive habit of two species and may be involved in the expansion in habitats of P. major.

Aqueousmethanol extracts of Cit rus junos, C. unshiu and C. sudachi fruit peel in hib ited the growth of the roots and hypocotyls of alfalfa (Medicago sativa L.), cress (Lepidiumsativum L.) and lettuce (Lactuca sativa L.) seedlings. Signifi cantreductions in the root and hypocotyl growth were observed as the extract concentration in creased in all bioassays. The in hibitory activity of C. junos ex tract on the growth of test plants was 3.3-to 17.9-fold and 3.6- to 20.6-fold greater than that of C. unshiu and C. sudachi extracts, respectively. Theconcent rationin C. junos was 3.5- and 4.9-fold greater than that in C. unshiu and C. sudachi, re spectively. Thus, there was a good correlation-between abscisic acid-b-D-glucopyranosylester (ABA-GE) concentrationsin C. junos, C. unshiu and C. sudachi fruit peel and theinhibito ryactivities of the irextracts. The concentration of ABA-GE in C. junos fruit peel was in creased with fruit maturityasgrowthinhibit oryactivity of C. junos fruit peel was reported to be in creased with fruit maturity, in dicating that the concentrations of ABA-GEin C. junos fruit peel was correlated withgrowthinhibit oryactivity of C. junos fruit peel in time course of fruit maturation. These findings suggest that ABA-GE may be involved in the growth inhibitory effect of C. junos, C. unshiu and C. sudachi fruit peel.

Ability of metabolic adaptation in upland and lowland rice (Oryza sativa L.) seedlings to flooding stress was compared. Flooding stress increased alcohol dehydrogenase (ADH) activity and ethanol concentration in shoots and roots of the upland and lowland rice seedlings. The difference in ADH activity and ethanol concentration in shoots between the upland and lowland rice was not apparent. However, both ADH activity and ethanol concentration in roots of the lowland rice were 2-fold greater than those in roots of the upland rice, suggesting that flooding-induction of ethanolic fermentation in lowland rice roots may be significantly greater than that in the upland rice roots. Since flooding often causes the anaerobic conditions in rooting zone than aerial part of plants and ethanolic fermentation is essential to survive in the anaerobic conditions, the ability of metabolic adaptation in lowland rice seedlings to flooding stress may be greater than that in upland rice seedlings.

The n-hexane-, acetone- and water-soluble fractions obtained from an aqueous acetone extract of lemon balm (Melissa officinalis L.) shoots inhibited the germination and the growth of roots and shoots of cockscomb (Amaranthus caudatus L.), cress (Lepidium sativum L.), crabgrass (Digitaria sanguinalis L.), timothy (Phleum pratense L.), lettuce (Lactuca sativa L.) and ryegrass (Lolium multiflorum Lam.). The inhibitory activity of the water-soluble fraction was the greatest, followed by that of acetone- and n-hexane-soluble fractions in all bioassays. The effectiveness of these fractions on the roots was greater than that of the shoots of the test plants. Significant reductions in the germination and growth of the roots and shoots were observed as the extract concentration increased. Such rate-dependent responses of the test plants to the fractions suggest that each fraction might contain allelochemical(s), but that the greatest potential was in the water-soluble fraction.

In order to clarify the induction of alcohol dehydrogenase (ADH) by anaerobiosis in oat (Avena sativa L.), the seedlings were exposed to anaerobiosis and activity of ADH and ADH isozyme profiles were determined. The anaerobiosis increased ADH activities in shoots and roots of the seedlings. By day 2, the activity increased 5 and 4 times in the roots and the shoots, respectively, compared with those under aerobic condition. Based on nondenaturing electrophoresis, ADH isozyme composition analysis revealed six bands consisting of a dimmer enzyme with submits encoded by three different Adh genes. Changes in staining intensity of the isozymes indicated that the increase in ADH activity in oat under anaerobiosis resulted from increased enzyme synthesis.

Exogenously applied ABA-β-d-glucopyranosyl ester (ABA-GE) inhibited shoot growth of alfalfa (Medicago sativa L.), cress (Lepidium sativum L.), lettuce (Lactuca sativa L.), Digitaria sanguinalis L., timothy (Pheleum pratense L.) and ryegrass (Lolium multiflorum Lam.) seedlings at concentrations greater than 0.1 μM. The growth inhibitory activity of ABA-GE on these shoots was 26–40% of that of (+)-ABA. ABA-β-d-glucosidase activities in these seedlings were 11–31 nmol mg−1 protein min−1. These results suggests that exogenously applied ABA-GE may be absorbed by plant roots and hydrolyzed by ABA-β-d-glucosidase, and liberated free ABA may induce the growth inhibition in these plants. Thus, although ABA-GE had been thought to be physiologically inactive ABA conjugate, ABA-GE may have important physiological functions rather than an inactive conjugated ABA form.

Anoxia tolerance and ethanol sensitivity of rice (Oryza sativa L.) and oat (Avena sativa L.) seedlings were evaluated to clarify their growth habit in anoxia. Anoxic stress inhibited elongation and dry weight gain of coleoptiles of the oat and rice seedlings; however, the inhibition of the oat coleoptiles was much greater than that of the rice coleoptiles. Anoxic stress increased endogenous ethanol concentration and alcohol dehydrogenase activity in oat and rice coleoptiles and their increases in the rice coleoptiles were much greater than those in the oat coleoptiles. At concentrations greater than 30 mM and 300 mM, exogenously applied ethanol inhibited the elongation and weight gain for the oat and the rice coleoptiles, respectively, and the inhibition was increased with increasing ethanol concentrations with marked inhibition being achieved on the oat coleoptiles. These results suggest that anoxia tolerance and induction of ethanolic fermentation in anoxia may be greater in rice than oat, and ethanol sensitivity of rice may be lower than that of oat.