Search Results (18)

As endemic or regionally distinctive taxa in China, Ottelia species exhibit notable ecological adaptability as well as potential nutritional and medicinal value. Nevertheless, a comprehensive characterization and comparative analysis of the chemical constituents across this genus remain lacking, particularly for O. acuminata var. jingxiensis, O. fengshanensis, and O. guanyangensis. This knowledge gap has hindered the systematic exploitation and value-added utilization of Ottelia resources. In the present study, five Ottelia taxa—O. acuminata, O. acuminata var. jingxiensis, O. fengshanensis, O. guanyangensis, and O. alismoides—were investigated. By integrating widely targeted metabolomics, network pharmacology, and in vitro experimental validation, we identified Rivularin, Tenaxin I, Sinensetin, 8-Methoxyapigenin, Chrysoeriol, Hispidulin, Genkwanin, 5,2′-Dihydroxy-7,8-dimethoxyflavone, Kumatakenin, and Pectolinarigenin as key antioxidant constituents in the Genus Ottelia. Network-based analyses further indicated that these compounds predominantly act on PTGS1/2 and AR, and may mediate antioxidant activity primarily through the PI3K–Akt signaling pathway and pathways associated with EGFR tyrosine kinase inhibitor resistance. Collectively, these findings provide a scientific basis for the further development, functional evaluation, and sustainable utilization of the Genus Ottelia. Full article

The effects of static magnetic field (SMF) treatment on the solid-state culture of Sanghuangporus vaninii (SV) were investigated to enhance metabolite production and bioactivity. SMF parameters including intensity, exposure duration, and temperature were optimized, and treatment at 4 mT for 2 h per day produced the most pronounced effects, increasing total flavonoid (TFC), polyphenol (TPC), and triterpenoid (TTC) contents by 61–438% compared with the control. Ultrasonic extraction and semi-preparative chromatography enabled the isolation of three key compounds: D-(+)-trehalose (1), 5,7-dihydroxy-3,4′-dimethoxyflavone (2), and pinolenic acid (3), all of which were elevated following SMF treatment. Importantly, SMF exposure was associated with enhanced inhibitory activities against enzymes relevant to chronic metabolic disorders. The overall inhibitory activities against α-amylase, α-glucosidase, pancreatic lipase, and xanthine oxidase increased by 6–28% compared with the control, reaching a maximum inhibition of 97.60 ± 0.17%. Preliminary in vitro screening at 100 μg/mL showed that compounds 1 and 2 inhibited both α-amylase and α-glucosidase, whereas compound 3 selectively inhibited pancreatic lipase. Subsequent IC₅₀ analysis confirmed that compound 2 under SMF treatment exhibited inhibitory activity comparable to acarbose against α-amylase (45.62 μg/mL vs. 52.18 μg/mL) and α-glucosidase (38.74 μg/mL vs. 35.42 μg/mL). In addition, compound 3 showed moderate inhibition of pancreatic lipase with an IC₅₀ value of 42.15 μg/mL. These findings suggest that SMF treatment may enhance metabolite production and in vitro enzyme inhibitory activity in S. vaninii. However, these results are limited to in vitro assays, and further studies including cellular and in vivo validation, toxicity assessment, and pharmacokinetic evaluation, are required before any therapeutic or industrial applications can be considered. Full article

Rich natural sources of the flavone tricin (5,7,4′-trihydroxy-3′,5′-dimethoxyflavone; systematic IUPAC name: 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4H-1-benzopyran-4-one) are actively sought since this compound is endowed with a broad spectrum of biological activities and its dietary supplementation has been considered as a colon cancer chemoprotectant and for the treatment of human intestinal polyps. This paper describes a straightforward procedure for the high-yield isolation of flavonoids and tricin from aerial parts of Huperzia brevifolia (Hook. & Grev.) Holub, which grows on the paramos of Southern Ecuador. Compared to existing procedures, this method requires limited organic solvent and no chromatographic separation. In brief, the selective separation of the metabolites expressed in H. brevifolia was achieved by exploiting their different chemical properties under basic or acidic conditions. The identity of isolated tricin was firmly established by 1D and 2D NMR spectra. The contents of the total flavonoid fraction (TFF) and tricin in dried aerial parts of H. brevifolia were determined to be 4.48% w/w (44.8 mg/g) and 3.89% w/w (38.9 mg/g), respectively, using HPLC-DAD analysis. On the other hand, unoptimized crystallization of TFF delivered pure tricin in a 0.66% (w/w) yield relative to TFF, which corresponded to 2.96% w/w (29.6 mg/g) of dried aerial parts. This concentration of tricin is thus one of the highest in any plant species and makes H. brevifolia a valuable source of the flavone for preclinical trials and dietary supplementation for colon health. Full article

Chromatographic fractionation of a methanol extract of Helichrysum rutilans afforded seven known compounds. The isolated compounds were identified as 5,7,8-trihydroxy-3,6-dimethoxyflavone-8-O-2-methyl-2-butanoate (C-1), 5,7-dihydroxy-3,6,8-trimethoxyflavone (C-2), 5-hydroxy-3,6,7,8-tetramethoxyflavone (C-3), 5-hydroxy-3,6,7-trimethoxyflavone (C-4), ent-kaurenoic acid (C-5), ent-kauran-18-al (C-6), and 15-α-hydroxy-(-)-ent-kaur-16-en-19-oic acid (C-7). Compounds C-1–C-4 demonstrated high antioxidant capacities on ORAC hydroxyl radical (2.114 ± 4.01; 2.413 ± 6.20; 1.924 ± 16.40; 1.917 ± 3.91) × 10⁶; ORAC peroxyl radical (3.523 ± 3.22; 2.935 ± 0.13; 2.431 ± 8.63; 2.814 ± 5.20) × 10³ µMTE/g; and FRAP (1251.45 ± 4.18; 1402.62 ± 5.77) µMAAE/g, respectively. Moderate inhibitory activities against Fe²⁺-induced lipid peroxidation were observed for C-1–C-4 as IC₅₀ values of 13.123 ± 0.34, 16.421 ± 0.92, 11.64 ± 1.72, 14.90 ± 0.06 µg/mL, respectively, while their respective anti-tyrosinase activities with IC₅₀ values of 25.735 ± 9.62, 24.062 ± 0.61, 39.03 ± 13.12, 37.67 ± 0.98 µg/mL were also observed. All compounds demonstrated TEAC values within the range of 1105–1424 µMTE/g. The result is an indication that a methanol extract of H. rutilans might possibly be a good source of natural antioxidants against ailments caused by cellular oxidative stress and as inhibitors against skin depigmentation, as well as possible raw materials needed for slowing down perishable agricultural products. This is the first report on the phytochemical and biological evaluation of H. rutilans. Full article

Fusarium oxysporum is one of the most harmful soil-borne pathogens that cause root rot, damping-off, and wilt disease in many plant species. Management of Fusarium oxysporum diseases is often by using many harmful and expensive chemical fungicides which have many harmful effects on the environment and human health. The current study was conducted to identify the chemical constituents of black cumin seeds’ methanolic extract and investigate the ability of the major constituents to inhibit the Fusarium oxysporum trypsin-like serine protease, which play an important role in F. oxysporun pathogenicity. The HPLC-MS analysis of black cumin seeds’ methanolic extract revealed the presence of seven major compounds: amentoflavone, Procyanidin C2, Quercetin3-O-sophoroside-7-O-rhamnoside, 5,7-Dihydroxy-3,4-dimethoxyflavone, Borapetoside A, tetrahydroxy-urs-12-en-28-O-[b-D-glucopyranosyl (1-2)-b-D-glucopyranosyl] ester, and kudzusapongenol A-hexA-pen. The results of molecular docking between these compounds and the active site of Fusarium oxysporium trypsin showed that only four compounds were able to bind to the active site of F. oxysporum trypsin. Amentoflavone, 5,7-Dihydroxy-3,4-dimethoxyflavone, and Quercetin3-O-sophoroside-7-O-rhamnoside have the highest binding energy, −6.4, −6.5, and −6.5 Kcal/mol, respectively. In addition, the results clarify that 5,7-Dihydroxy-3,4-dimethoxyflavone was the only compound to form a hydrogen bond with Asp189 (the residue responsible for substrate specificity). The results of the study strongly indicate that flavonoids of black cumin seeds’ methanolic extract could be used as effective inhibitors for the F. oxysporum trypsin-like serine protease. Full article

Diabetes mellitus (DM) is a group of systemic metabolic disorders with a high rate of morbidity and mortality worldwide. Due to the detrimental side effects of the current treatment, there is a great need to develop more effective antidiabetic drugs with fewer side effects. Natural products are a well-known source for the discovery of new scaffolds for drug discovery, including new antidiabetic drugs. The genus Helichrysum has been shown to produce antidiabetic natural products. In this investigation, the methanolic extract of H. cymosum and H. pandurifolium resulted in the isolation and identification of eleven known compounds viz 5,8-dihydroxy-7-methoxy-2-phenyl flavanone (1), pinostrobin (2), dihydrobaicalein (3), glabranin (4), allopatuletin (5), pinostrobin chalcone (6), helichrysetin (7), 5-hydroxy-3,7-dimethoxyflavone (8), 3,5-dihydroxy-6,7,8-trimethoxyflavone (9), 3-O-methylquercetin (10), and 3-methylethergalangin (11). The in vitro bio-evaluation of isolated compounds against alpha-glucosidase showed that 10, 5, and 11 demonstrated the highest alpha-glucosidase inhibitory activity with IC₅₀ values of 9.24 ± 0.4, 12.94 ± 0.2, and 16.00 ± 2.4 μM respectively, followed by 7 and 3 with IC₅₀ values of 18.16 ± 1.2 and 44.44 ± 0.2 μM respectively. However, none of these compounds showed a measurable inhibitory effect on alpha-amylase under the experimental conditions used except compound 10 which showed a poor alpha-amylase inhibitory activity with an IC₅₀ value of 230.66 ± 15.8 μM. Additionally, strong total antioxidant capacities were demonstrated by 10, 5 and 7 in ferric-ion reducing antioxidant power assay (374.34 ± 69.7; 334.37 ± 1.7; 279.93 ± 0.8) µmol AAE/mmol. This is the first scientific report to be carried out on alpha-glucosidase inhibitory activities and antioxidant capacities of H. cymosum constituents and a first report on the isolation and identification of methoxyflavanoids from H. pandurifolium. Our findings suggest that these compounds are promising candidates to inhibit alpha-glucosidase as well as oxidative stress related to diabetes. Results from molecular docking provided insight into the observed in vitro alpha-glucosidase inhibitory activities for 5, 7, 10, and 11. It is envisaged that the isolated phytochemicals from these plants may contribute to the development of hypoglycemic lead compounds with anti-diabetic potential. Full article

Four new compounds, 5-hydroxy-2′,6′-dimethoxyflavone (4), 5-hydroxy-2′,3′,6′-trimethoxyflavone (5), 5-dihydroxy-6-methoxyflavone (6), and 5,6′-dihydroxy-2′,3′-dimethoxyflavone (7), and three known compounds, 1,3-diphenylpropane-1,3-dione (1), 5-hydroxyflavone (2), and 5-hydroxy-2′-methoxyflavone (3), were isolated from the aerial parts of Hottonia palustris. Their chemical structures were determined through the use of spectral, spectroscopic and crystallographic methods. The quantitative analysis of the compounds (1–7) and the zapotin (ZAP) in methanol (HP1), petroleum (HP6), and two chloroform extracts (HP7 and HP8) were also determined using HPLC-PDA. The biological activity of these compounds and extracts on the oral squamous carcinoma cell (SCC-25) line was investigated by considering their cytotoxic effects using the MTT assay. Subsequently, the most active compounds and extracts were assessed for their effect on DNA biosynthesis. It was found that all tested samples during 48 h treatment of SCC-25 cells induced the DNA biosynthesis-inhibitory activity: compound 1 (IC₅₀, 29.10 ± 1.45 µM), compound 7 (IC₅₀, 40.60 ± 1.65 µM) and extracts ZAP (IC₅₀, 20.33 ± 1.01 µM), HP6 (IC₅₀, 14.90 ± 0.74 µg), HP7 (IC₅₀, 16.70 ± 0.83 µg), and HP1 (IC₅₀, 30.30 ± 1.15 µg). The data suggest that the novel polymethoxyflavones isolated from Hottonia palustris evoke potent DNA biosynthesis inhibitory activity that may be considered in further studies on experimental pharmacotherapy of oral squamous cell carcinoma. Full article

Crop diseases caused by Fusarium pathogens, among other microorganisms, threaten crop production in both commercial and smallholder farming. There are increasing concerns about the use of conventional synthetic fungicides due to fungal resistance and the associated negative effects of these chemicals on human health, livestock and the environment. This leads to the search for alternative fungicides from nature, especially from plants. The objectives of this study were to characterize isolated compounds from Combretum erythrophyllum (Burch.) Sond. and Withania somnifera (L.) Dunal leaf extracts, evaluate their antifungal activity against Fusarium pathogens, their phytotoxicity on maize seed germination and their cytotoxicity effect on Raw 264.7 macrophage cells. The investigation led to the isolation of antifungal compounds characterized as 5-hydroxy-7,4′-dimethoxyflavone, maslinic acid (21-hydroxy-3-oxo-olean-12-en-28-oic acid) and withaferin A (4β,27-dihydroxy-1-oxo-5β,6β-epoxywitha-2-24-dienolide). The structural elucidation of the isolated compounds was established using nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy (MS) and, in comparison, with the available published data. These compounds showed good antifungal activity with minimum inhibitory concentrations (MIC) less than 1.0 mg/mL against one or more of the tested Fusarium pathogens (F. oxysporum, F. verticilloides, F. subglutinans, F. proliferatum, F. solani, F. graminearum, F. chlamydosporum and F. semitectum). The findings from this study indicate that medicinal plants are a good source of natural antifungals. Furthermore, the isolated antifungal compounds did not show any phytotoxic effects on maize seed germination. The toxicity of the compounds A (5-hydroxy-7,4′-dimethoxyflavone) and AI (4β,27-dihydroxy-1-oxo-5β,6β-epoxywitha-2-24-dienolide) was dose-dependent, while compound B (21-hydroxy-3-oxo-olean-12-en-28-oic acid) showed no toxicity effect against Raw 264.7 macrophage cells. Full article

Catalpa pod has been used in traditional medicine for the treatment of diabetes mellitus in South America. Studies on the constituents of Catalpa species have shown that it is rich in iridoids. In the present study, three previously undescribed compounds (2–4), including two secoiridoid derivatives along with twelve known compounds, were isolated from the fruits of Catalpa bignonioides Walt. In addition, fully assigned ¹³C-NMR of 5,6-dihydroxy-7,4’-dimethoxyflavone-6-O-sophoroside (1) is reported for the first time in the present study. The structures of compounds were determined on the basis of extensive spectroscopic methods, including UV, IR, 1D, and 2D NMR, mass spectroscopy, and CD spectroscopic data. All the isolated compounds were evaluated for α-glucosidase inhibitory activity. Among the tested compounds, compounds 2, 3, and 9 exhibited significant inhibitory activity against α-glucosidase enzyme assay. Meanwhile, the effect of compounds 2, 3, and 9 on glucose-stimulated insulin secretion (GSIS) was measured using pancreatic β-cells. Compounds 2, 3, and 9 exhibited non-cytotoxicity-stimulated insulin secretion in INS-1 cells. The expression levels of proteins associated with β-cell function and insulin secretion such as phosphorylation of total insulin receptor substrate-2 (IRS-2), phosphatidylinositol 3-kinase (PI3K), Akt, activated pancreatic duodenal homeobox-1 (PDX-1), and peroxisome proliferator-activated receptor-γ (PPAR-γ) were increased in INS-1 cells after treatment with compounds 2, 3, and 9. The findings of the present study could provide a scientific warrant for their application as a potential antidiabetic agent. Full article

Helicteres hirsuta Lour. (H. hirsuta) has been traditionally used as a folk medicine for treating a range of common diseases. It has been used in furuncle treatment, pain relief, dysentery, measles, flu, antimalaria and antiobesity treatments in some Asian countries, revealing that this plant material contains important bioactive compounds which are linked with health benefits and/or can act as therapeutic agents. Hence, many attempts have been made to isolate and identify the key bioactive compounds present in H. hirsuta and conduct in vitro tests to investigate their biological activities. We recently revealed that H. hirsuta leaf has a high total phenolic content (TPC: 192.6 mg gallic acid equivalents (GAE)/g) and total flavonoid content (TFC: 215.2 mg catechin equivalents (CE)/g). The stem of H. hirsuta also had high contents of TPC and TFC (212.6 mg GAE/g and 280.1 mg CE/g, respectively). The results also revealed that phenolic compounds from this plant had a strong positive correlation with antioxidant capacity including DPPH, ABTS radical scavenging activity and ferric reducing antioxidant power (R² range of 0.78 and 0.99), which are known to link with diverse bioactivities including antioxidant, antimicrobial, anticancer, antiobesity and antidiabetic effects. Additionally, H. hirsuta leaf and stem were found to contain high levels of saponins (808.0 and 347.5 mg escin equivalents/g, respectively), that were determined using colorimetric assay. Several individual compounds have been identified in the extracts of H. hirsuta, including rutin, methyl caffeate, 5,8-dihydroxy-7,4-dimethoxyflavone, isoscutellarein 4-methyl ether 8-O--d-glucopyranoside, 4,4-sulfinylbis(2(tert-butyl)-5-methylphenol), 7-O-methylisoscutellarein, 7,4-di-O-methylisoscutellarein, six lignans (pinoresinol, medioresinol, syringaresinol, boehmenan, boehmenan H and trans-dihydrodiconiferyl alcohol), betulinic acid, 3-O-trans-caffeoylbetulinic acid, 3-benzoylbetulinic acid, betulinic acid methyl ester, lupeol, 3β-O-acetylbetulinic acid, simiarenol, stigmasterol and β-sitosterol. The derived extracts and isolated compounds from this plant have been shown to inhibit the growth of various cancer cell lines in vitro and offer a promising source of active compounds against other health problems including obesity, diabetes and malaria. Further studies on the mechanisms of bioactive compounds from this plant are suggested to elucidate their mechanisms of action for health benefits. In addition, more in vivo tests associated with clinical trials are also needed to validate and confirm their effects for further development of nutraceutical and pharmaceutical products from this plant material. Full article

Natural products have served as primary remedies since ancient times due to their cultural acceptance and outstanding biodiversity. To investigate whether Tamarix aphylla L. modulates an inflammatory process, we carried out bioassay-guided isolation where the extracts and isolated compounds were tested for their modulatory effects on several inflammatory indicators, such as nitric oxide (NO), reactive oxygen species (ROS), proinflammatory cytokine; tumour necrosis factor (TNF-α), as well as the proliferation of the lymphocyte T-cells. The aqueous ethanolic extract of the plant inhibited the intracellular ROS production, NO generation, and T-cell proliferation. The aqueous ethanolic crude extract was partitioned by liquid-liquid fractionation using n-hexane (n-C₆H₆), dichloromethane (DCM), ethyl acetate (EtOAc), n-butanol (n-BuOH), and water (H₂O). The DCM and n-BuOH extracts showed the highest activity against most inflammatory indicators and were further purified to obtain compounds 1–4. The structures of 3,5-dihydroxy-4’,7-dimethoxyflavone (1) and 3,5-dihydroxy-4-methoxybenzoic acid methyl ester (2) from the DCM extracts; and kaempferol (3), and 3-hydroxy-4-methoxy-(E)-cinnamic acid (4) from the n-BuOH extract were elucidated by different spectroscopic tools, including MS, NMR, UV, and IR. Compound 2 inhibited the production of ROS and TNF-α, whereas compound 3 showed inhibitory activity against all the tested mediators. A better understanding of the potential aspect of Tamarix aphylla L. derivatives as anti-inflammatory agents could open the door for the development of advanced anti-inflammatory entities. Full article

The infusion of the desertic plant Nolana ramosissima I.M. Johnst showed vascular smooth muscle relaxation in rat aorta and the presence of several phenolic compounds, which were detected by high resolution UHPLC-Orbitrap-HESI-MS. In addition, five flavonoids were rapidly isolated from a methanolic extract using high-performance counter-current chromatography (HPCCC). The N. ramosissima extract showed endothelium-independent relaxation effect in rat aorta. Sixty-one compounds were detected in the infusion, mainly glycosylated flavonoids, flavanones and several oxylipins, suggesting that a synergistic effect between the compounds in the extracts could be responsible for the relaxation activity. Vascular activity experiments were done in isolated organ bath. In rat aorta, a nitric oxide inhibitor did not prevent the relaxation effects of the extract; however, a selective guanylyl cyclase inhibitor partially blunted this effect. The compound 5,3′-dihydroxy-4′7-dimethoxyflavone presented higher relaxation effect than 100 μg/mL of N. ramosissima extract. The extract and the isolated metabolites from N. ramosissima can show relaxation effects on rat aorta by a mechanism that is independent of the endothelium. Full article

The current study aimed to investigate, for the first time, the beneficial effects of 3,5-dihydroxy-4′,7-dimethoxyflavone isolated from Tamarix aphylla L. against liver injury in mice. Liver injury was induced by intraperitoneal (i.p.) injection of carbon tetrachloride (CCl₄) at a dose of 0.4 mL/kg mixed in olive oil at ratio (1:4) twice a week for 6 consecutive weeks. The administration of CCl₄ caused significant histopathological changes in liver tissues while the pre-treatment with the flavone at dose of 10 and 25 mg/kg ameliorated the observed liver damages. Also, it markedly reduced hepatic malondialdehyde (MDA) level as well as increased the activities of liver superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (Gpx) compared with their recorded levels in CCl₄ model group. Moreover, the immunohistochemical analysis demonstrated the enhancement in the protein level of B-cell lymphoma-2 (Bcl-2) while the protein levels of cysteine-aspartic acid protease-3 (caspase-3), Bcl-2-associated x protein (Bax), transforming growth factor-β1 (TGF-β1) and CD31 were suppressed following the flavone treatement. These results suggest that the flavone can inhibit liver injury induced in mice owning to its impact on the oxidation, apoptotic and angiogenesis mechanisms. Further pharmacological investigations are essential to determine the effectiveness of the flavone in human. Full article

Ochratoxin A (OTA) is a mycotoxin with a serious impact on human health. In Mediterranean countries, the black Aspergilli group, in particular Aspergillus carbonarius, causes the highest OTA contamination. Here we describe the synthesis of three polyphenolic flavonoids: 5-hydroxy-6,7-dimethoxy-flavone (MOS), 5,6-dihydroxy-7-methoxy-flavone (NEG), and 5,6 dihydroxy-flavone (DHF), as well as their effect on the prevention of OTA biosynthesis and lipoxygenase (LOX) activity in A. carbonarius cultured in a conducive liquid medium. The best control effect on OTA biosynthesis was achieved using NEG and DHF. In fungal cultures treated with these compounds at 5, 25, and 50 μg/mL, OTA biosynthesis significantly decreased throughout the 8-day experiment. NEG and DHF appear to have an inhibiting effect also on the activity of LOX, whereas MOS, which did not significantly inhibit OTA production, had no effect on LOX activity. The presence of free hydroxyls in catecholic position in the molecule appears to be a determining factor for significantly inhibiting OTA biosynthesis. However, the presence of a methoxy group in C-7 in NEG could slightly lower the molecule’s reactivity increasing OTA inhibition by this molecule at 5 μg/mL. Polyphenolic flavonoids present in edible plants may be easily synthesized and used to control OTA biosynthesis. Full article

Four new constituents, as 5, 7-dihydroxy-4′-methoxyflavonol-3-O-β-d-arabinopyranosyl-(2′′→1′′′)-O-β-d-arabinopyrnosyl-2′′′-O-3′′′′, 7′′′′-dimethylnonan-1′′′′-oate (1), 5-hydroxy-7, 4′-dimethoxyflavone-5-O-α-d-arabinopyranosyl-(2"→1′′′)-O-α-d-arabinopyranosyl-2′′′-O-3′′′′, 7′′′′-dimethylnonan-1′′′′-oate (2), 5-hydroxy-7, 4′-dimethoxyflavone-5-O-β-d-arabinofuranosyl-(2"→1′′′)-O-β-d-arabinopyranosyl-2′′′-O-lanost-5-ene (3) and 4′,4′′-diferuloxy feruloyl-O-α-d-arabinopyranosyl-(2a→1b)-O-α-d-arabinopyranosyl-(2b→1c)-O-α-d-arabinopyranosyl-(2c→1d)-O-α-d-arabinopyranosyl-(2d→1e)-O-α-d-arabinopyranosyl-2e-3′′′, 7′′′-dimethylnonan-1′′′-oate (4), along with three known compounds (5–7) were isolated from Oryza sativa leaves and straw. The structures of new and known compounds were elucidated by 1D (¹H and ¹³C NMR) and 2D NMR spectral methods, viz: COSY, HMBC, and HSQC aided by mass techniques and IR spectroscopy. The cytotoxicity of these constituents was assessed by using (RAW 264.7) mouse macrophage cell line, and allelopathic effects of compounds (1–7) on the germination and seedling growth characteristics such as seedling length and root length of barnyardgrass (Echinochloa oryzicola) were evaluated. Significant inhibitory activity was exhibited by compounds comprising flavone derivatives such as (1–3) on all of seed germination characteristics. The allelopathic effect of flavone derivatives were more pronounced on seedling length and root length than the germination characteristics. The higher concentration of flavone derivatives showed stronger inhibitory effects, whereas the lower concentrations showed stimulatory effects in some cases. Full article