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Polycavernoside E (1), a new polycavernoside analog, was isolated from a marine Okeania sp. cyanobacterium. The relative configuration was elucidated primarily by analyzing the two dimensional nuclear magnetism resonance (2D NMR) data. The absolute configuration was clarified by comparing the electronic circular dichroism (ECD) data of 1 with those of known analogs. Polycavernoside E (1) exhibited moderate antitrypanosomal activity against Trypanosoma brucei rhodesiense. Furthermore, the isolation of polycavernoside E (1) from marine cyanobacteria provides additional evidence that marine cyanobacteria, and not red algae, are responsible for the biosynthesis of polycavernosides.

Logging operations of Liriodendron tulipifera L., as timber trees, and fallen leaves in autumn from ornamental trees produce a large amount of leaf waste. In this study, the allelopathy of L. tulipifera fresh and fallen leaves was investigated for the development of potential applications of leaf waste. The extracts of fresh and fallen leaves of L. tulipifera showed growth inhibitory activity against weed species, Vulpia myuros (L.) C.C.Gmel., Echinochloa crus-galli (L.) P.Beauv., and Lolium multiflorum Lam., under laboratory conditions. The powder of L. tulipifera fresh and fallen leaves also inhibited the germination of E. crus-galli under greenhouse conditions. A potent allelochemical was isolated from fresh and fallen leaf extracts through a bioassay-guided separation process, and was identified as lipiferolide. Lipiferolide inhibited the growth of L. multiflorum and Lepidum sativum in a concentration-dependent manner. This investigation suggests that the leaf waste of L. tulipifera from logging operations and fallen leaves is potentially useful for the purpose of weed control, such as through the use of soil additive materials from leaves or the creation of foliar spray from leaf extracts. The development of weed control materials using L. tulipifera leaf waste may be a means with which to minimize waste, reducing environmental impacts and economic concerns.

Chamaecyparis obtusa (Siebold et Zucc.) Endl. is cultivated in the temperate region of East Asia for its high-quality and profitable timber. The timber-processing industry produces a large amount of waste, such as tree bark, branches, and leaves, and finding ways to minimize such waste is economically and environmentally efficient. In the present study, the allelopathic activity and allelochemicals of the C. obtusa leaves were investigated to develop potential application methods. C. obtusa leaves were phytotoxic and associated leaf extracts significantly suppressed the growth of the weeds; Echinochloa crus-galli, Phleum pratense and Lolium multiflorum under laboratory conditions. The leaf powder applied onto the soil surface also suppressed the germination of E. crus-galli and P. pratense under greenhouse conditions. Hinokiic acid and (+)-dihydrosesamin were isolated from the leaves and structurally identified. Both compounds suppressed the growth of cress and P. pratense in a concentration dependent manner. When the leaves of C. obtua were applied as a soil additive, hinokiic acid and (+)-dihydrosesamin in the leaves potentially cause the growth inhibitory activity by leaching into the soil. These experiments showed that the leaves and the leaf extracts of C. obtusa are phytotoxic. These experiments also demonstrated that the leaves and the leaf extracts of C. obtusa have growth inhibitory potential against several plant species, and the leaves produce allelochemicals. Therefore, the leaves and leaf extracts of C. obtusa may be useful for weed suppression purposes. The leaf biomass of C. obtusa is frequently large and the timber processing industry produces significant leaf waste. The development of weed control products using waste leaves may be a solution to minimize the timber processing waste to reduce environmental impact and provide economic value. However, leaf material should be evaluated for weed suppression and herbicidal activity as a soil additive and also possible as a foliar spray under field conditions.

Plant parts and extracts that are rich in bioactive substances with allelopathic potential can be explored as a possible alternative to herbicides for natural weed control in sustainable agriculture. In the present study, we investigated the allelopathic potential of Marsdenia tenacissima leaves and its active substances. Aqueous methanol extracts of M. tenacissima showed significant inhibitory activities against the growth of lettuce (Lactuca sativa L.), alfalfa (Medicago sativa L.), timothy (Phleum pratense L.), and barnyard grass (Echinochloa crusgalli (L.) Beauv.). The extracts were purified through various chromatography steps, and one active substance was isolated and determined by spectral data to be a novel compound, assigned as steroidal glycoside 3 (8-dehydroxy-11β-O-acetyl-12β-O-tigloyl-17β-marsdenin). Steroidal glycoside 3 significantly inhibited the seedling growth of cress at a concentration of 0.03 mM. The concentrations needed for 50% growth inhibition of the cress shoots and roots were 0.25 and 0.03 mM, respectively. These results suggest that steroidal glycoside 3 may be responsible for the allelopathy of M. tenacissima leaves.

Polygonum chinense Linn. is a medicinal and invasive plant that belongs to the family Polygonaceae. The pharmacological activities and phytochemical constituents of Polygonum chinense are well reported, but the allelopathic effects and potent allelopathic substances of P. chinense remain to be investigated. Hence, this experiment was conducted to separate and characterize potentially allelopathic substances from an extract of the Polygonum chinense plant. The Polygonum chinense plant extracts highly suppressed the growth of cress (Lepidium sativum L.), lettuce (Lactuca sativa L.), barnyard grass (Echinochloa crusgalli (L.) P. Beauv.), and timothy grass (Phleum pratense L.) seedlings in a species- and concentration-dependent way. Two active substances were separated using a series of purification procedures and determined through spectral analysis as (−)-3-hydroxy-β-ionone and (−)-3-hydroxy-7,8-dihydro-β-ionone. These two compounds significantly suppressed the seedling growth of Lepidium sativum (cress) at concentrations of 0.01 and 1 mM, respectively. The extract concentrations necessary for 50% growth inhibition (I50 values) of the cress hypocotyls and roots were 0.05 and 0.07 mM for (−)-3-hydroxy-β-ionone, respectively, and 0.42 and 1.29 mM for (−)-3-hydroxy-7,8-β-ionone, respectively. These findings suggest that these two compounds are in charge of the inhibitory effects of the Polygonum chinense extract and may serve as weed control agents.

Osmanthus fragrans Lour. has been cultivated for more than 2500 years because of the fragrance and color of the flowers. The flowers and roots have been used in tea, liquors, foods, and traditional Chinese medicine. The species contains more than 180 compounds including terpenoids, phenylpropanoids, polyphenols, flavonoids, and sterols. However, there has been limited information available on the allelopathic properties and allelopathic substances of O. fragrans. We investigated the allelopathy and allelopathic substances of O. fragrans and Osmanthus heterophyllus (G.Don) P.S. Green, as well as Osmanthus × fortunei Carrière, which is the hybrid species between O. fragrans and O. heterophyllus. The leaf extracts of O. fragrans, O. heterophyllus, and O. × fortunei suppressed the growth of cress (Lepidium sativum L.), alfalfa (Medicago sativa L.), Lolium multiflorum Lam., and Vulpia myuros (L.) C.C.Gmel with the extract concentration dependently. The extract of the hybrid species O. × fortune was the most active among the extracts. The main allelopathic substances of O. × fortunei and O. fragrans were isolated and identified as (+)-pinoresinol and 10-acetoxyligustroside, respectively. (+)-Pinoresinol was also found in the fallen leaves of O. × fortunei. Both compounds showed an allelopathic activity on the growth of cress and L. multiflorum. On the other hand, several allelopathic substances including (+)-pinoresinol may be involved in the allelopathy of O. heterophyllus. O. fragrans, O. heterophyllus, and O. × fortunei are evergreen trees. but their senescent leaves fall and cover the soil under the trees. It is possible that those allelopathic substances are liberated through the decomposition process of the leaves into their rhizosphere soil, and that they accumulate in the soil and provide a competitive advantage to the species through the inhibition of the growth of the neighboring competing plants. Therefore, the leaves of these Osmanthus species are allelopathic and potentially useful for weed management options in some agriculture settings to reduce commercial herbicide dependency for the developing sustainable agriculture systems.

The phytotoxic potential of plants and the effect of their active components on another plant species is being explored as a potential alternative to synthetic herbicides for weed control. In the current study, we investigated the phytotoxic potential of the leaves of Dregea volubilis (L.f.) Benth. ex Hook.f. against four test plants [timothy (Phleum pratense L.), barnyard grass (Echinochloa crus-galli (L.) P. Beauv), lettuce (Lactuca sativa L.), and alfalfa (Medicago sativa L.)] and observed significant growth inhibition on those plants at concentrations >3 mg D.W. equivalent extract mL−1. A bioassay-governed purification of the D. volubilis extracts using different chromatography phases produced two growth inhibitory compounds, 3-hydroxy-α-ionone (compound 1) and 5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one (compound 2). The compounds retarded the growth of barnyard grass and cress (Lepidium sativum L.) with I50 (concentration required for 50% growth suppression) values ranging from 0.098 to 0.450 mM for 3-hydroxy-α-ionone and 0.029 to 0.420 mM for 5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one. Thus, the extracts and identified compounds may have the possibility to be utilized as bioagents for weed control.

Cassia alata (Caesalpiniaceae) is a large perennial shrub native to tropical America. It is an important medicinal and ornamental plant and has been reported to possess several pharmacological properties. However, phytotoxic substances from C. alata have not yet been documented in the literature. Therefore, this study seeks to evaluate the phytotoxic potential of C. alata leaves and to identify inhibitory substances for the purpose of eco-friendly weed management. The effect of aqueous methanol extracts of C. alata on the seedling growth of alfalfa, cress, lettuce, rapeseed, barnyard grass, foxtail fescue, Italian ryegrass, and timothy was examined. The level of inhibition of the extracts corresponded to concentration. Several chromatographic steps were performed to separate the extracts, and through spectroscopic analysis, two active substances were isolated and characterised as rutin and syringone. These two active substances significantly inhibited the seedling growth of cress and foxtail fescue. The range of I50 values (required concentration for 50% growth inhibition) of rutin and syringone for the seedling growth of cress and foxtail fescue were 129.5–417.8 and 160.1–466.5 µM, respectively. These results indicate that the two identified active phytotoxic substances from C. alata may be responsible for its growth inhibitory properties.

Phytotoxic substances in plants that may serve as alternative natural herbicides for controlling weeds are required for sustainable agriculture. We explored the phytotoxic activities of aqueous methanol extracts of Senna garrettiana (Craib) Irwin & Barneby leaves and the active substances they contain. The results revealed that the S. garrettiana leaf extracts had significant phytotoxic effects on three dicotyledons (Lepidium sativum L., Lactuca sativa L., and Medicago sativa L.) and two monocotyledons (Phleum pratense L. and Lolium multiflorum Lam.). An bioassay-guided isolation process yielded three active substances; caffeic acid, methyl caffeate, and (S)-6-hydroxymellein inhibited the seed germination, seedling growth, and biomass accumulation of L. sativum in a concentration-dependent manner. Based on the concentration required for 50% growth inhibition (IC50), (S)-6-hydroxymellein had the highest inhibitory effects on L. sativum in all test parameters, followed by methyl caffeate and caffeic acid. The L. sativum roots were the most susceptible to (S)-6-hydroxymellein (IC50 = 383 µM) and caffeic acid (IC50 = 2627 µM), whereas methyl caffeate (IC50 = 1361 µM) had the greatest effect on the L. sativum shoots. Thus, three isolated compounds may explain the phytotoxic effects of the S. garrettiana extracts. Consequently, caffeic acid, methyl caffeate, and (S)-6-hydroxymellein could be potential candidates for the future production of bioherbicides.

The plant Plumbago rosea Linn., belonging to the Plumbaginaceae family, is an important medicinal herb distributed in part of Southeast Asia, and there are many reports of its pharmacological properties. However, the allelopathic activities of P. rosea have not been examined. Thus, the present study was conducted to assess the allelopathic activity of P. rosea and to identify its allelopathic substances. The aqueous methanol stem extract of P. rosea significantly suppressed the seedling growth of barnyard grass (Echinochloa crus-galli L. P. Beauv.), Italian ryegrass (Lolium multiflorum Lam.), timothy (Phleum pretense L.), cress (Lepidium sativum L.), lettuce (Lactuca sativa L.), and alfalfa (Medicago sativa L.). The extract of P. rosea was then purified through chromatographic steps, and two active substances were isolated and determined as 7,4′,5′-tri-O-methyl dihydroquercetin and 7,4′,5′-tri-O-methylampelopsin. The two compounds significantly inhibited the seedling growth of cress, with 7,4′,5′-tri-O-methylampelopsin showing a greater inhibitory effect than 7,4′,5′-tri-O-methyl dihydroquercetin. This result may be due to the 3′-OH group in 7,4′,5′-tri-O-methylampelopsin. The effective concentrations of both compounds required for 50% growth inhibition (EC50 values) of cress seedlings were 0.24 mM and 0.59 mM for root and shoot, and 0.07 mM and 0.21 mM, respectively. These findings suggest that the two compounds may contribute to the allelopathic effect of P. rosea and could be used as a natural source of allelopathic substances.

Medicinal plants are rich sources of bioactive substances that can be used to develop environmentally friendly weed control alternatives. Marsdenia tenacissima (Roxb.) Moon is a traditional medicinal plant well known for its pharmacological activities and several bioactive compounds. However, its allelopathy and related substances have not been reported. Hence, the present study was conducted to explore the allelopathic potential and substances from M. tenacissima leaves. Aqueous methanol extracts of M. tenacissima showed significant inhibitory activities against the growth of cress (Lepidium sativum L.) and Italian ryegrass (Lolium multiflorum Lam.). The extracts were purified through various chromatography steps, and two allelopathic substances were isolated and determined by spectral data to be steroidal glycoside 1 (5,6-dihydrogen-11α-O-acetyl-12β-O-tigloyl-17β-marsdenin), a novel compound, and steroidal glycoside 2 (5,6-dihydrogen-11α,12β-di-O-tigloyl-17β-marsdenin). Both compounds significantly inhibited the growth of cress seedlings. Steroidal glycoside 1 showed 1.6- and 4-times greater growth inhibitory potential against the cress shoots and roots than steroidal glycoside 2. The concentrations needed for 50% growth inhibition of the cress seedling shoots and roots were 0.46 and 0.03 mM for steroidal glycoside 1, respectively, and 0.74 and 0.12 mM for steroidal glycoside 2, respectively. Therefore, these results suggest that steroidal glycosides 1 and 2 may be responsible for the allelopathy of the M. tenacissima leaves.

Senna garrettiana (Craib) Irwin & Barneby (Fabaceae) is a medicinal plant known to be rich in biologically active compounds that could be exploited to produce bioherbicides. The present study was conducted to explore the allelopathic potential and phytotoxic substances of S. garrettiana. Extracts of S. garrettiana leaves were found to significantly inhibit the growth of Lepidium sativum L. and Echinochloa crus-galli (L.) P. Beauv. (p ≤ 0.05). The phytotoxic substances were isolated and identified as vanillic acid and ferulic acid by bioassay-directed fractionation and spectral data analysis. The two compounds were shown to significantly inhibit the seed germination, seedling growth, and dry biomass of L. sativum. Based on the concentration required for 50% growth inhibition (defined as IC50), the roots of L. sativum were the most sensitive to the compounds, and the inhibitory effect of ferulic acid (IC50 = 0.62 mM) was >1.3 times more potent than that of vanillic acid (IC50 = 0.82 mM). In addition, a mixture of the two compounds (0.3 mM) resulted in synergistic inhibitory activity against the L. sativum roots compared with the individual compounds. These results suggest that the extracts of S. garrettiana leaves and their phytotoxic compounds have potential as candidate natural herbicides.

Allelopathic plants and their related phytotoxic chemicals have been explored as alternatives for environmentally friendly weed management. Dregea volubilis (L.f.) Benth. ex Hook.f., a woody vine, is well-known for its uses in various therapeutic treatments, and several bioactive compounds have been isolated from this species. However, to date, no phytotoxic substances from D. volubilis have been reported. Hence, in this research, we aimed to investigate the allelopathic effect of D. volubilis and characterize its phytotoxic substances. Extracts of D. volubilis exhibited significant inhibitory activity against the seedling growth of Italian ryegrass (Lolium multiflorum Lam.) and cress (Lepidium sativum L.). The extracts were purified through several chromatography steps, yielding two phytotoxic substances, and using spectroscopy, their structures were determined as dehydrovomifoliol and loliolide. The compounds inhibited the Italian ryegrass and cress seedlings with the I50 (concentrations needed for 50% inhibition) values ranging from 0.022 to 0.102 mM, for loliolide and 3.24–4.60 mM, for dehydrovomifoliol. These results suggest that both phytotoxic compounds might be responsible for the allelopathy of D. volubilis, and they may be released into the soil through the decomposition of the D. volubilis leaf and probably act as allelopathic active substances. Therefore, the extracts of D. volubilis and its related phytotoxic compounds may be applied as biological agents for controlling weeds.

Paspalum commersonii (Poaceae) is a herbaceous perennial weed distributed in the tropics and subtropics regions and grows mainly in the moist, or even flooded soil. It often appears in the rice field as a competitive weed and difficult to manage. Its strong competitive nature indicates possible allelopathic potential of P. commersonii. However, no studies have been found yet on the allelopathic activity of P. commersonii. Thus, we investigated the allelopathic potential of this weed and determined its allelopathic substances. Aqueous methanol extracts of P. commersonii showed concentration-dependent inhibitory activity on the seedling growth of cress, alfalfa, rapeseed, lettuce, barnyard grass, foxtail fescue, Italian ryegrass, and timothy. Two substances were isolated through bioassay-guided fractionation and their structures were determined through spectral data as dehydrovomifoliol and loliolide. Dehydrovomifoliol and loliolide started inhibiting the shoot and root growth of cress at concentrations greater than 3 and 0.03 mM, respectively. The concentrations required for 50% inhibition (I50) of cress shoot and root growth were 3.34 and >3.50 mM for dehydrovomifoliol and 0.04 and 0.05 mM for loliolide, respectively. These results indicate that both substances may affect the inhibitory activity of P. commersonii.

Metasequoia glyptostroboides Hu et W.C. Cheng is one of the oldest living conifer species, and it has remained unchanged for millions of years compared to its fossils from the Cretaceous period. The species are cultivated in the parks, gardens, and roadsides in many countries. We investigated the allelopathy and allelopathic substances in fallen leaves of M. glyptostroboides. An aqueous methanol extract of the fallen leaves inhibited the growth of cress (Lepidium sativum L.), lettuce (Lactuca sativa L.), alfalfa (Medicago sativa L.), Lolium multiflorum Lam., Phleum pretense L., and Vulpia myuros (L.) C.C.Gmel. The extract was then purified by several chromatographic steps, and two allelopathic substances were isolated and determined by spectral data to be (+)-rhododendrol and 9-epi-blumenol C. The compound inhibited the growth of cress and L. multiflorum. M. glyptostroboides is a deciduous perennial tree, and accumulation of its fallen leaves occur on the soil under the trees. Therefore, those allelopathic substances in the fallen leaves may be liberated into the rhizosphere soil during the decomposition process of fallen leaves and provide a competitive advantage for M. glyptostrob through the growth inhibition of competing plant species nearby. Therefore, M. glyptostroboides is allelopathic, and (+)-rhododendrol and 9-epi-blumenol C may be contribute to the allelopathy.

Metabolomics can be used to study complex mixtures of natural products, or secondary metabolites, for many different purposes. One productive application of metabolomics that has emerged in recent years is the guiding direction for isolating molecules with structural novelty through analysis of untargeted LC-MS/MS data. The metabolomics-driven investigation and bioassay-guided fractionation of a biomass assemblage from the South China Sea dominated by a marine filamentous cyanobacteria, cf. Neolyngbya sp., has led to the discovery of a natural product in this study, wenchangamide A (1). Wenchangamide A was found to concentration-dependently cause fast-onset apoptosis in HCT116 human colon cancer cells in vitro (24 h IC50 = 38 μM). Untargeted metabolomics, by way of MS/MS molecular networking, was used further to generate a structural proposal for a new natural product analogue of 1, here coined wenchangamide B, which was present in the organic extract and bioactive sub-fractions of the biomass examined. The wenchangamides are of interest for anticancer drug discovery, and the characterization of these molecules will facilitate the future discovery of related natural products and development of synthetic analogues.

The present study was aimed to determine the allelopathic potential of mango (Mangifera indica L.) leaves and to identify allelopathic substances in the leaves. The aqueous methanol extracts of mango leaves inhibited seedling growth of garden cress, radish, rapeseed, foxtail fescue and crabgrass, and the inhibitory effects increased with the increasing extract concentration, suggesting that mango leaves may contain allelopathic substances. The extract was then purified by several chromatographic runs through a bioassay-directed fractionation, and an growth inhibitory substance was isolated and identified by spectral data as methyl-3,4,5-trihydroxybenzoate (methyl gallate). Methyl gallate at the concentration of 10 mM inhibited 98.6% and 99.8% of root and shoot growth of garden cress relative to the control, respectively, and 94.4% and 49.3% of those of foxtail fescue, respectively. The concentrations of methyl gallate required for 50% growth inhibition (I50) on garden cress roots and shoots were 3.9 and 3.3 mM, and those on foxtail fescue roots and shoots were 1.5 and 9.5 mM, respectively. It is the first report of an allelopathic substance in mango leaves and allelopathic activity of methyl gallate. Therefore, the mango leaves may have potential as a soil additive material for the weed management options.

The allelopathic potential of plant species and their related compounds has been increasingly reported to be biological tools for weed control. The allelopathic potential of Garcinia xanthochymus was assessed against several test plant species: lettuce, rapeseed, Italian ryegrass, and timothy. The extracts of G. xanthochymus leaves significantly inhibited all the test plants in a concentration- and species-specific manner. Therefore, to identify the specific compounds involved in the allelopathic activity of the G. xanthochymus extracts, assay-guided purification was carried out and two allelopathic compounds were isolated and identified as methyl phloretate {3-(4-hydroxyphenyl) propionic acid methyl ester} and vanillic acid (4-hydroxy-3-methoxybenzoic acid). Both of the substances significantly arrested the cress and timothy seedlings growth. I50 values (concentrations required for 50% inhibition) for shoots and roots growth of the cress and timothy were 113.6–104.6 and 53.3–40.5 μM, respectively, for methyl phloretate, and 331.6–314.7 and 118.8–107.4 μM, respectively, for vanillic acid, which implied that methyl phloretate was close to 3- and 2-fold more effective than vanillic acid against cress and timothy, respectively. This report is the first on the presence of methyl phloretate in a plant and its phytotoxic property. These observations suggest that methyl phloretate and vanillic acid might participate in the phytotoxicity of G. xanthochymus extract.

Albizia richardiana, a fast-growing, large deciduous tree belonging to the Fabaceae family, grows well in hot and humid areas but mainly grows in the tropics of the Old World. The medicinal and other uses of Albizia richardiana are well documented, but the phytotoxic effects of this tree have not yet been investigated. We conducted this study to investigate the phytotoxic activity of Albizia richardiana leaves and to identify growth inhibitory substances for controlling weeds in a sustainable way. Aqueous methanol extracts of Albizia richardiana leaves greatly suppressed the growth of cress and barnyard grass seedlings in a concentration- and species-dependent manner. Two phytotoxic substances were separated using several purification steps and characterized through spectral analysis as dehydrovomifoliol and loliolide. Dehydrovomifoliol and loliolide significantly arrested the seedling growth of cress in the concentrations of 0.1 and 0.01 mM, respectively. The extract concentrations needed for 50% growth inhibition (I50 values) of cress seedlings were 3.16–3.01 mM for dehydrovomifoliol and 0.03–0.02 mM for loliolide. The results suggest that these two allelopathic substances might play a vital role in the phytotoxicity of Albizia richardiana leaves.

Wedelia chinensis (Asteraceae) is a wetland herb native to India, China, and Japan. It is a valuable medicinal plant recorded to have pharmaceutical properties. However, the phytotoxic potential of Wedelia chinensis has not yet been examined. Thus, we carried out this study to establish the allelopathic effects of Wedelia chinensis and to identify its phytotoxic substances. Extracts of Wedelia chinensis exhibited high inhibitory activity against the root and shoot growth of cress, alfalfa, rapeseed, lettuce, foxtail fescue, Italian ryegrass, timothy, and barnyard grass. The inhibition was varied with species and was dependent on concentrations. The extracts were separated through several purification steps, and the two effective substances were isolated and characterized as vanillic acid and gallic acid using spectral analysis. Vanillic acid and gallic acid significantly arrested the growth of cress and Italian ryegrass seedlings. The concentrations of vanillic acid and gallic acid needed for 50% inhibition (I50 values) of the seedling growth of the cress and Italian ryegrass were 0.04–15.4 and 0.45–6.6 mM, respectively. The findings suggest that vanillic acid and gallic acid may be required for the growth inhibitory activities of Wedelia chinensis.

The phytotoxic potential of plants and their constituents against other plants is being increasingly investigated as a possible alternative to synthetic herbicides to control weeds in crop fields. In this study, we explored the phytotoxicity and phytotoxic substances of Schumannianthus dichotomus, a perennial wetland shrub native to Bangladesh, India, and Myanmar. Leaf extracts of S. dichotomus exerted strong phytotoxicity against two dicot species, alfalfa and cress, and two monocot species, barnyard grass and Italian ryegrass. A bioassay-driven purification process yielded two phenolic derivatives, syringic acid and methyl syringate. Both constituents significantly inhibited the growth of cress and Italian ryegrass in a concentration-dependent manner. The concentrations required for 50% growth inhibition (I50 value) of the shoot and root growth of cress were 75.8 and 61.3 μM, respectively, for syringic acid, compared with 43.2 and 31.5 μM, respectively, for methyl syringate. Similarly, to suppress the shoot and root growth of Italian rye grass, a greater amount of syringic acid (I50 = 213.7 and 175.9 μM) was needed than methyl syringate (I50 = 140.4 to 130.8 μM). Methyl syringate showed higher phytotoxic potential than syringic acid, and cress showed higher sensitivity to both substances. This study is the first to report on the phytotoxic potential of S. dichotomus and to identify phytotoxic substances from this plant material.

Neem (Azadirachta indica) has been widely used as a traditional medicine and several bioactive compounds have been isolated from this species, but to date no potent allelopathic active substance has been reported. Therefore, we investigated possible allelopathic property and phytotoxic substances with allelopathic activity in neem. An aqueous methanol extract of neem leaves inhibited the growth of roots and shoots of cress, lettuce, alfalfa, timothy, crabgrass, ryegrass, barnyard grass and jungle rice. The extracts were then purified by several chromatographic runs while monitoring the inhibitory activity and two phytotoxic substances were isolated. The chemical structures of the two substances were determined by spectral data to correspond to novel compounds, nimbolide B (1) and nimbic acid B (2). Nimbolide B inhibited the growth of cress and barnyard grass at concentrations greater than 0.1‒3.0 μM. Nimbic acid B inhibited the growth of cress and barnyard grass at concentrations greater than 0.3–1.0 μM. These results suggest that nimbolide B and nimbic acid B may contribute to the allelopathic effects caused by neem leaves.

Cyatheaceae (tree ferns) appeared during the Jurassic period and some of the species still remain. Those species may have some morphological and/or physiological characteristics for survival. A tree fern was observed to suppress the growth of other ligneous plants in a tropical forest. It was assumed that the fern may release toxic substances into the forest floor, but those toxic substances have not yet been identified. Therefore, we investigated the phytotoxicity and phytotoxic substances of Cyathea lepifera (J. Sm. ex Hook.) Copel. An aqueous methanol extract of C. lepifera fronds inhibited the growth of roots and shoots of dicotyledonous garden cress (Lepidum sativum L.), lettuce (Lactuca sativa L.), and alfalfa (Medicago sativa L.), and monocotyledonous ryegrass (Lolium multiflorum Lam.), timothy (Phleum pratense L.), and barnyardgrass (Echinochloa crus-galli (L.) P. Beauv.). The results suggest that C. lepifera fronds may have phytotoxicity and contain some phytotoxic substances. The extract was purified through several chromatographic steps during which inhibitory activity was monitored, and p-coumaric acid and (-)-3-hydroxy-β-ionone were isolated. Those compounds showed phytotoxic activity and may contribute to the phytotoxic effects caused by the C. lepifera fronds. The fronds fall and accumulate on the forest floor through defoliation, and the compounds may be released into the forest soils through the decomposition process of the fronds. The phytotoxic activities of the compounds may be partly responsible for the fern’s survival.

Plants are sources of diversified allelopathic substances that can be investigated for use in eco-friendly and efficient herbicides. An aqueous methanol extract from the leaves of Garcinia xanthochymus exhibited strong inhibitory activity against barnyard grass (Echinochloa crus-galli (L.) P. Beauv.), foxtail fescue (Vulpia myuros (L.) C.C.), alfalfa (Medicago sativa L.), and cress (Lepidium sativum L.), and appears to be a promising source of allelopathic substances. Hence, bio-activity guided purification of the extract through a series of column chromatography steps yielded a novel compound assigned as garcienone ((R, E)-5-hydroxy-5-((6S, 9S)-6-methyl-9-(prop-13-en-10-yl) tetrahydrofuran-6-yl) pent-3-en-2-one). Garcienone significantly inhibited the growth of cress at a concentration of 10 μM. The concentrations resulting in 50% growth inhibition (I50) of cress roots and shoots were 120.5 and 156.3 μM, respectively. This report is the first to isolate and identify garcienone and to determine its allelopathic potential.

Cancer remains one of the most lethal diseases worldwide. There is an urgent need for new drugs with novel modes of action and thus considerable research has been conducted for new anticancer drugs from natural sources, especially plants, microbes and marine organisms. Marine populations represent reservoirs of novel bioactive metabolites with diverse groups of chemical structures. This review highlights the impact of marine organisms, with particular emphasis on marine plants, algae, bacteria, actinomycetes, fungi, sponges and soft corals. Anti-cancer effects of marine natural products in in vitro and in vivo studies were first introduced; their activity in the prevention of tumor formation and the related compound-induced apoptosis and cytotoxicities were tackled. The possible molecular mechanisms behind the biological effects are also presented. The review highlights the diversity of marine organisms, novel chemical structures, and chemical property space. Finally, therapeutic strategies and the present use of marine-derived components, its future direction and limitations are discussed.

Anredera cordifolia (Tenore) Steenis is widely planted as an ornamental and medicinal plant in Indonesia. On the other hand, in some other countries this plant is classified as a noxious weed. As a harmful weed, A. cordifolia is reported to have the ability to smother all native vegetation, collapse canopies of tall trees, cultivate as a ground cover and disrupt native seedling development. There is no available information about the involvement of any allelochemicals from A. cordifolia related to these issues. The present study evaluated the allelopathic effect by isolating and identifying the allelopathic substance from A. cordifolia leaf extract. The allelopathic potency of A. cordifolia was determined by a series of bioassays of shoot and root growth on some selected test plants. Separation and purification of the active substances was achieved through several chromatography processes. Finally, the substances with allelopathic activity were identified through high-resolution electrospray ionization mass spectrometry (HRESIMS) analysis and determined by the specific rotation of compound, proton and carbon NMR spectroscopies. The results show that A. cordifolia possesses allelopathic properties which affect other plant species. The isolated compound from the plant material, 3-hydroxy-alpha-ionone, may contribute to the allelopathic effects of A. cordifolia.

Aqueous methanol extracts of a traditional Bangladeshi rice cultivar (Oryza sativa L. cv. Kartikshail) inhibited root and shoot growth of cress (Lepidium sativum), lettuce (Lactuca sativa), alfalfa (Medicago sativa), timothy (Phleum pratense), crabgrass (Digitaria sanguinalis), Italian ryegrass (Lolium multiflorum), barnyardgrass (Echinochloa crus-galli) and jungle rice (Echinochloa colonum). The inhibition was increased with increasing the extract concentration, which suggests that cv. Kartikshail may have growth inhibitory substances and allelopathic potential. The aqueous methanol extract of cv. Kartikshail was purified and two main inhibitory substances were isolated and identified by spectral data as 3-hydroxy-β-ionone and 9-hydroxy-4-megastigmen-3-one. The concentrations required for 50% growth inhibition on cress roots and shoots, respectively, were 4.9 and 9.5 μM for 3-hydroxy-β-ionone, and 0.54 and 0.72 μM for 9-hydroxy-4-megastigmen-3-one. The concentrations required for 50% growth inhibition on barnyardgrass roots and shoots, respectively, were 160 and 310 μM for 3-hydroxy-β-ionone, and 53 and 140 μM for 9-hydroxy-4-megastigmen-3-one. The inhibitory activity of a mixture of the two compounds was much higher than that of the sum of the two compounds, suggesting that the two compounds may act synergistically to inhibit the growth of cress and barnyardgrass. The present research suggests that 3-hydroxy- β-ionone and 9-hydroxy-4-megastigmen-3-one may be responsible for the growth inhibitory effect of cv. Kartikshail and may play important roles in the allelopathy of cv. Kartikshail. The traditional Bangladeshi rice cultivar Kartikshail may be potentially useful for weed management as a weed suppressing agent when this rice cultivar is incorporated into the soil or included in rice-based cropping systems.

A series of new C11 cyclopentenones 1-7 was isolated, together with four known metabolites 9/10, 12 and 13, from the extract of the didemnid ascidian Lissoclinum sp. The other didemnid ascidian Diplosoma sp. contained didemnenones 1, 2 and 5, and five known metabolites 8-12. The structures of 1-7 were elucidated by spectroscopic analyses. Cytotoxicity of the isolated compounds was evaluated against three human cancer cell lines (HCT116, A431 and A549).

Three new compounds of the malyngamide series, 6,8-di-O-acetylmalyngamide 2 (1), 6-O-acetylmalyngamide 2 (2), and N-demethyl-isomalyngamide I (3), were isolated from the marine cyanobacterium Moorea producens. Their structures were determined by spectroscopic analysis and chemical derivatization and degradation. These compounds stimulated glucose uptake in cultured L6 myotubes. In particular, 6,8-di-O-acetylmalyngamide 2 (1) showed potent activity and activated adenosine monophosphate-activated protein kinase (AMPK).

Hyptis suaveolens (Lamiaceae) is an exotic invasive plant in many countries. Earlier studies reported that the aqueous, methanol, and aqueous methanol extract of H. suaveolens and its residues have phytotoxic properties. However, to date, the phytotoxic substances of this plant have not been reported. Therefore, the objectives of this study were isolation and identification of phytotoxic substances of H. suaveolens. Aqueous methanol extract of this plant was purified by several chromatographic runs through bioassay guided fractionation using garden cress (Lepidium sativum) as a test plant. Final purification of a phytotoxic substance was achieved by reverse phase HPLC and characterized as 14α-hydroxy-13β-abiet-8-en-18-oic acid (suaveolic acid) by high-resolution ESI-MS, 1H-,13C-NMR, CD, and specific rotation. Suaveolic acid inhibited the shoot growth of garden cress, lettuce (Lactuca sativa), Italian ryegrass (Lolium multiflorum), and barnyard grass (Echinochloa crus-galli) at concentrations greater than 30 µM. Root growth of all but lettuce was also inhibited at concentrations greater than 30 µM. The inhibitory activities were concentration dependent. Concentrations required for 50% growth inhibition of suaveolic acid for those test plant species were ranged from 76 to 1155 µM. Therefore, suaveolic acid is phytotoxic and may be responsible for the phytotoxicity of H. suaveolens plant extracts.