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Two new triucallane triterpenoids, polystanin F (1) and polystanin G (2), along with eight known compounds (3-10) were isolated from the fruits of Aphanamixis polystachya. Their structures were established on the basis of extensive spectroscopic analysis. Moreover, eight compounds were evaluated for their in vitro cytotoxicity against three cancer cell lines (liver cancer RT112, colon cancer HCT-116 and breast cancer M231) using the MTT method. Compound 7 showed significant cytotoxic activity against HCT-116 with IC50 1.27 µM.

Three new mexicanolide limonoids were obtained from the 90% ethanol extract of the seeds of Khaya senegalensis. Their structures were elucidated as senegalenines A-C (1-3) by analysing their 1D/2D NMR and MS spectroscopic analysis. In addition, the isolated limonoids were tested in vitro for antimicrobial potentials against 5 pathogenic microorganisms. Consequently, compounds 1-3 exhibited antimicrobial activity against the tested Gram negative bacteria at the minimum inhibitory concentration values less than 40 µg/ml.

Phytochemical investigation on the 90% EtOH extract of the seeds of Cipadessa cinerascensa led to the isolation of three new limonoids, cinerascenoids A-C (1-3). Structural elucidation of all the c...

Four undescribed highly oxidized and rearranged limonoids, secotrijugins A-D, were purified from the leaves and twigs of Trichilia sinensis. Within them, secotrijugin A was characterized as a rare 30-nortrijugin-type limonoid with an unusual cleavage of 1,14-ether bond, secotrijugins B and C represented new examples with the cleavage of δ-lactone ring D, and secotrijugin D was a rare trijugin-type limonoid with an unusual 2,6-oxygen bridge. The structures of limonoids were characterized by means of spectroscopic analysis and ECD calculations. The cellular screening revealed that secotrijugin B was the most active against LPS-stimulated NO production in BV-2 cells, which played an anti-inflammatory role by downregulating COX-2 and iNOS protein expression. The further in vivo experiments confirmed that secotrijugin B had strong in vivo anti-inflammatory effect via suppressing NO and ROS generation.

An ethnobotanical study of Buru Community Forest was conducted using Participatory Rural Appraisal techniques. A total of 91 species of plants belonging to 43 Families with high endemicity were recorded. The dominant families were Fabaceae, Euphorbiaceae, and Meliaceae. Many species such as Tetrapleura tetrapetra, Phyllanthus mullerianus, Sarcocephalus latifolius and Aframomum melegueta had multiple uses. The three major uses of the species are for medicinal (39 species), edible (33 species) and construction purposes (30 species). Keywords: Buru community forest, Ethnobotanical, Participatory Rural Appraisal technique.

Fusarium pseudocircinatum is the main causal agent of big-leaf mahogany malformation disease (BLMMD) of mahogany (Swietenia macrophylla) in Mexico. Although, BLMMD is the most important disease for this high-value timber species, there is a lack of information on the genetic variation present in geographically diverse isolates of F. pseudocircinatum. The objective of this study was to determine the genetic diversity of populations of F. pseudocircinatum causing BLMMD in the central western region of Mexico. A total of 611 big-leaf mahogany trees were inspected at eight sites in four states (Colima, Guerrero, Jalisco and Michoacán); of these, 42.7% showed malformation symptoms similar to those of BLMMD. Of 374 Fusarium isolates that were recovered, 277 were identified as F. pseudocircinatum, 56 were F. mexicanum, and 41 were Fusarium spp. An ISSR analysis of the F. pseudocircinatum isolates generated 51 bands of which 38 were polymorphic (76.8%) with a mean of 17 bands per primer. A total of 87 multilocus genotypes (MLGs) were identified. Nei's genetic diversity analysis showed that the isolates had a high genetic diversity average (0.147), with values ranging from 0.070 to 0.365 depending of the geographical location. An analysis of molecular variance revealed that the variation within the populations was low (27.36%), while the variation within MLGs was significant (72.64%), indicating genetic flow. Overall, the genetic variability of F. pseudocircinatum populations was high and the MLGs from Colima (Colima) and Gabriel Zamora (Michoacán) were placed centrally, which possibly is evidence of ancestry and indicates its dispersion routes in the central western region of Mexico.

Introduction Melia toosendan Sieb. et Zucc. has been used as a Chinese folk medicine for roundworm treatment since ancient times. Many diverse limonoids have been isolated from Meliaceae plants, but it remains difficult to isolate and identify other limonoids because of their small natural concentrations. Objective This study was performed to overcome the difficulties associated with fast and accurate identification of limonoids and establish a reliable and sensitive method for the analysis of minor limonoids in M. toosendan fruits. Methods An efficient strategy for enrichment, detection, and identification of minor limonoids from M. toosendan fruits using solid-phase extraction with high-performance liquid chromatography-quadrupole time-of-flight tandem mass spectrometry (SPE-HPLC-Q-TOF-MS/MS) was developed herein. Results Characteristic fragmentations and fragmentation ions containing trichilin-, nimbin-, and vilasinin-class limonoid skeletons were initially studied, and characteristic diagnostic ions involved retro Diels-Alder (RDA) reactions or homolytic cleavages, which were used to identify minor limonoids. In total, 13 limonoids, including four new ones, were identified. Conclusion This is the first report on the analysis of M. toosendan fruits to identify limonoids. This novel analysis method may stimulate further research regarding the identification of limonoids in other plant species.

A seco-apotirucallane-type triterpenoid, namely angustifolianin (1), along with three dammarane-type triterpenoids, (20S, 24S)-epoxy-dammarane-3β,25-diol (2), 3-epi-cabraleahydroxylactone (3), and ...

A new andirobin-type limonoid with modified furan ring, khaysenelide K (1), together with a known analogue (2), was isolated from the stem barks of Khaya senegalensis. The structure and absolute configuration of 1 were elucidated by a combination of 1D and 2D NMR, HRESIMS, and single-crystal X-ray diffraction using mirror Cu-Kα radiation. Compound 1 showed moderate NO inhibitory activity in LPS-activated RAW 264.7 macrophages with IC50 value of 27.74 ± 0.68 μM.[Formula: see text].

Aims: This study was designed to evaluate the antidiabetic effects of aqueous and ethanolic extracts of Trichilia emetica (TE) stem bark in albinos rats. Methodology: 24 rats of comparable weight were divided into 2 lots, including a control lot of 3 rats and a test lot of 21 rats. Diabetes was induced by injecting Alloxan® intraperitoneally (125 mg/kg bw) for 7 days. After the onset of diabetes, the animals were divided into several groups and given the extracts of Trichilia emetica and Diastabol® orally for 6 days according to the following protocol: Normal Control (NC) received normal saline, group diabetic control (DC) it consists of untreated diabetic, group DD10 and DD20 was comprised of diabetic animals treated with Diastabol® at a doses of 10 and 20 mg/kg bw respectively , group DTEE100 and DTEE200 it consists of diabetic animals treated with ethanolic extract at a doses of 100 and 200 mg/kg bw respectively, group DTEA100 and DDTEA 200 was comprised of diabetic animals treated with aqueous extract at a same dose (100 and 200 mg/kg bw). At the end of experimentation, some blood was collected for the determination of some biochemical parameters such as insulin, blood glucose, AST, ALT, urea and creatinine. Systolic blood pressure (SBP), diastolic blood pressure (DBP), cardiac frequency (CF) were also recorded. Results: The results showed a significant (P

Chukrasia velutina is an enthnomedicinally used plant reported to have significant medicinal values. The present study aimed to explore the pharmacological activities of bark methanol extract using in vitro, in vivo and in silico models.The study was designed to investigate the pharmacological effects of methanol extract of Chukrasia velutina bark (MECVB) through in vitro, in vivo and in silico assays. Analgesic activity was tested using formalin-induced nociception and acetic acid-induced writhing assays while the antipyretic effect was tested using yeast-induced hyperthermia in mice model. The antioxidant effect was tested using the DPPH and reducing power assay and the cytotoxic screening was tested using the brine shrimp lethality bioassay. In addition, in silico studies were conducted using computer aided methods.In the acetic acid-induced writhing assay, the extract showed 28.36% and 56.16% inhibition of writhing for doses of 200 and 400 mg/kg, respectively. Moreover, a dose-dependent formalin-induced licking response was observed in both early and late phase. In yeast-induced pyrexia, the MECVB exhibited (p 0.05) antipyretic effect. The extract demonstrated an ICThe bark of Chukrasia velutina showed significant analgesic and antipyretic properties and is a potential source of natural anti-oxidative agents.

From the stem bark of Entandrophragma angolense, six undescribed compounds were isolated, including seco-tirucallane type triterpenoids, limonoids, and a catechin glucoside, along with nineteen known structures. All structures were determined by interpretation of spectroscopic and HRMS data, and absolute configuration was confirmed with the aid of electronic circular dichroism. The isolated compounds were tested for LPS-induced NO inhibition in RAW 264.7 macrophages and EC

Three new sesquiterpene phenol dimers, bidysoxyphenols A-C (2-4), along with two known compounds, namely sesquiterpene phenol (1) and ionone derivatives (5), were isolated from the leaves of Dysoxylum parasiticum (Osbeck) Kosterm. The structures of these new compounds, including their absolute configurations, were elucidated by nuclear magnetic resonance spectroscopy, ultraviolet spectroscopy, infrared spectroscopy, high-resolution electrospray ionization time-of-flight mass spectrometry, and electronic circular dichroism. Compounds 1 and 2 showed cytotoxicity against human promyelocytic leukemia cells, with IC

Three new limonoids, walsurauias A-C (1-3), along with four known ones, were isolated from the leaves and twigs of Walsura yunnanensis C. Y. Wu. Their structures were determined on the basis of comprehensive spectroscopic data analysis. The new limonoids were screened for their cytotoxic activity (IC

Plant-originated triterpenes are important insecticidal molecules. The research on insecticidal activity of molecules from Meliaceae plants has always received attention due to the molecules from this family showing a variety of insecticidal activities with diverse mechanisms of action. In this paper, we discuss 102 triterpenoid molecules with insecticidal activity of plants of eight genera (Aglaia, Aphanamixis, Azadirachta, Cabralea, Carapa, Cedrela, Chisocheton, and Chukrasia) in Meliaceae. In total, 19 insecticidal plant species are presented. Among these species, Azadirachta indica A. Juss is the most well-known insecticidal plant and azadirachtin is the active molecule most widely recognized and highly effective botanical insecticide. However, it is noteworthy that six species from Cedrela were reported to show insecticidal activity and deserve future study. In this paper, a total of 102 insecticidal molecules are summarized, including 96 nortriterpenes, 4 tetracyclic triterpenes, and 2 pentacyclic triterpenes. Results showed antifeedant activity, growth inhibition activity, poisonous activity, or other activities. Among them, 43 molecules from 15 plant species showed antifeedant activity against 16 insect species, 49 molecules from 14 plant species exhibited poisonous activity on 10 insect species, and 19 molecules from 11 plant species possessed growth regulatory activity on 12 insect species. Among these molecules, azadirachtins were found to be the most successful botanical insecticides. Still, other molecules possessed more than one type of obvious activity, including 7-deacetylgedunin, salannin, gedunin, azadirone, salannol, azadiradione, and methyl angolensate. Most of these molecules are only in the primary stage of study activity; their mechanism of action and structure–activity relationship warrant further study.

Three previously undescribed metabolites named argyrotoxins A-C, were isolated, together with the well known porritoxinol, its closely related phthalide, a phthalide derivative, zinniol, alternariol and its 4-methyl ether from Alternaria argyroxiphii E.G. Simmons & Aragaki, the causal agent of leaf spot on African mahogany trees, Khaya senegalensis A. Juss. (Meliaceae). The known compounds were identified comparing their physical and spectroscopic properties to those previously reported in literature. Argyrotoxins A-C were characterized essentially by NMR (1H, 13C, COSY, HSQC, HMBC and NOESY NMR spectra) and HRESIMS spectra as 4-(7-methoxy-6-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yloxy)-2-methyl-butyric acid, 5-but-2-enyloxy-N-(2-hydroxyethyl)-2-hydroxymethyl-3-methoxy-4-methyl-benzamide and 1-(5-(hydroxymethyl)-3-methoxy-4-(methoxymethyl)-2-methylphenoxy)-3-methylbutane-2,3-diol, respectively. The absolute configuration of argyrotoxin A was determined through electronic circular dichroism, by applying the biphenyl chiroptical probe approach. The phytoxicity of all metabolites isolated was evaluated by leaf puncture assay at concentration of 1 mg/mL. Zinniol proved to be the most active compound causing necrotic lesions on young leaves of Hedera elix L., Phaseolus vulgaris L. and Quercus ilex L. Argirotoxins A and B were found active, to a minor extent, on Phaseolus vulgaris L. leaves, while porritoxinol exhibited activity on holm oak leaves. The other secondary metabolites herein reported for A. argyroxiphii were inactive.

Field trials were conducted at two locations in Samaru (110 11'' N, 070 38'' E and 686m above sea level) and Maigana (110 10'' N, 070 37'' E and 675m above sea level) both in Northern Guinea Savannah ecological zone of Nigeria during the 2016 wet season to determine the effects of three concentration of aqueous Khaya seed extract (KSE) (20%w/v, 30%w/v and 40%w/v) on damage on cotton (SAMCOT 9) by bollworms. The experimental design was strip plot fitted into randomized complete block design. A total of four sprays at two weeks interval beginning from 9WAS (which corresponded to the period of formation of first square to the detection of first flower) were applied. Data were recorded on the number of terminal shoot damage, number of damaged shed squares, number of damaged shed cotton bolls and number of matured green bolls damaged by bollworms. There was no significant difference in the number of terminal shoot damaged by spiny bollworm (Earias spp.) from spray application of Lambda cyhalothrin, KSE and the untreated control. Significant reduction in the number of shed cotton squares, shed cotton bolls and matured green bolls damaged by bollworms were observed on Lambda cyhalothrin and 40%w/v KSE sprayed plots than the other treatments and the untreated control.

Khaya senegalensis is one of the largest and most majestic trees in Africa. Overexploited for its precious wood and medicinal values, the natural stands of this species are in danger of extinction in Cote d'Ivoire. Its sustainable management through regeneration techniques and assessment of its degree of adaptation to the changing climate is necessary. The aim of this study is to evaluate the effect of different environments on seedling germination and development in Khaya senegalensis. A total of 2160 seeds from different mother plants and 540 individuals from seed germination were selected and evaluated. The trials were conducted on three sites that were distinct by their microclimate (two nurseries in Cote d'Ivoire and one greenhouse in France). Analysis of variance showed that germination and morphology parameters were not influenced by the characteristics of the mother plants used (p > 0.05), but rather by the study sites (P < 0.05). The stable and controlled greenhouse climate was more advantageous for latency time (12.66 ± 0.80 days), germination delay (16.96 96 ± 0.54 days), germination speed (19.66 ± 2.95 days), germination duration (10.83 ± 2.27 days) and germination rate (88.88 ± 7.97) with more vigorous sowing than the other two sites. The results showed in general that the higher the height of the seedlings, the thicker the diameter of the seedlings (r = 0.796) and the higher the number of leaves (r = 0.946). This savannah species is native to the arid zones of Africa, but this study highlighted its adaptive potential to changing and different climates. These results are decision support tools for the regeneration of native pioneer forest species with high agroforestry potential and socio-economic importance such as Khaya senegalensis. This study could be extended to other species in order to restore disturbed ecosystems.

“Azadirachta indica” commonly called as neem, nimtree or Indian lilac, is a tree representing plant family “Meliaceae”. It is commonly and natively found in tropical and semi-tropical regions. It has high industrial demand due to its immediate application as an eco-friendly, biodegradable pesticides and immediate availability. The only trading and commercialized way to produce neem is extraction of seeds from the plant, but the seed availability is very limited as the tree flowers once in a year. Also due to firm and harsh out-breeding nature of the plant, seeds are heterozygous, resulting in the production of inconsistent metabolite. But now a day the production of azadirachta has been influenced by various strategies which involve androgenic cultures, beta cell generation, callus cultures, leaf, ovary, zygotic embryo cultures or many other ways. A.indica has been now used as a supplement for drug industry, cosmetics, photochemical, pharmacological and as a therapeutic because of the high content of antioxidant. It is used for the treatment of skin disorders with the help of various commercial products. Azadirachta indica also possesses anticancer activity and as a wound healer. There are many products available in market that can be used for various purposes either it can be for human use or for agricultural or poultry use or as biopesticides, certified by the government. They do not have any side effects and only target the micro-organisms for which they are designed. During pandemic covid-19 also Azadirachta indica has been recommended for different purposes to minimize the infection rate. The present review is to highlight the importance of A.indica, commercialization and with special focus on regeneration protocol development to multiply and enhance the important phytochemicals within it.

Three new diterpenes were isolated from the stems of Dysoxylum lukii Merr and characterized on the basis of spectral data. Neoclerod-13Z-ene-3α, 4β, 15-triol (3) exhibited the inhibition of lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages with an IC50 value of 25.49 μM.

Compared with the numerous natural enemies against insect pests that have been identified, the commercialization of natural biological control resources remains very limited. To increase the use of natural enemies for biological control, determining how to improve the low efficacy, slow speed, and high cost of natural enemies is very important. Mediterranean species of The whitefly, Bemisia tabaci (Gennadius) (Hemiptera: Aleyrodoidea), increasingly threatens many crops in China, and control primarily depends on chemical insecticides. Here, the effect of ethanol extracts from two plants, Agrimonia pilosa (Ledeb) (Rosales: Rosaceae) and Melia azedarach (Linn) (Meliaceae: Melia), on predominant natural enemies of B. tabaci was investigated using a leaf dipping or spraying method. The results showed that the ethanol extract of A. pilosa significantly improved the infectivity of the fungus Isaria javanica (Friedrichs & Bally) (Ascomycota: Hypocreales), and the mortality of whiteflies caused by the combination of fungus (105 spores/mL) with the extract of A. pilosa (2 mg/mL dried powder of A. pilosa containing 0.0942 mg/mL total polyphenols) was 81.6%, which was significantly higher than that caused by the fungus only. However, the ethanol extract of M. azedarach had no effect on fungus infectivity. Additionally, insecticide tolerance of the predator Pardosa pseudoannulata was also significantly improved by the extract of A. pilosa. The longevity of the parasitoid Encarsia formosa was not affected by the extracts. These findings indicate that the extract of A. pilosa played a dual role that included improving pathogenic fungi infectivity and insecticidal tolerance of a predator and thus could be a synergist in the biological control of B. tabaci.

Ten undescribed phragmalin-type limonoids (Chuktabularoids A-J, 1–10) and four known compounds (11–14) were isolated from the fruit shells of Chukrasia tabularis A. Juss. Their chemical structures were elucidated through a combination of HRESIMS, NMR, and ECD experiments. Their frameworks differed mainly in D-ring, including C-15-acyl, 16-nor C-15 acyl, C-13/14/18-cyclopropane, and Δ14, 15 types. The majority of the isolated compounds were investigated for multidrug resistance (MDR) reversal activity against doxorubicin-resistant human breast carcinoma (MCF-7/DOX) cells, compounds 11 and 12 exhibited a 5.6-fold and 19.7-fold enhancing effect on doxorubicin susceptibility at 30 μM, respectively.

Three new limonoids, walsucochinones A-C (1–3), along with eight known compounds, were isolated from an ethyl acetate extract of the bark of Walsura cochinchinensis. Their structures were determined using spectroscopic techniques, mainly 1-D and 2-D NMR. The ethyl acetate extract showed cytotoxic activity against MCF-7 human breast cancer cells and cytotoxicity of the isolated compounds were evaluated in vitro using the SRB assay. Walsucochinone C (3) exhibited the most active effect with IC50 value of 16.4 ± 0.2 μM.

An investigation on the extract from the plant Trichilia sinensis Bentv. led to the isolation of 13 new limonoids (1−13), in which two were of khayalactone skeleton and 11 were phragmalin-type limonoids, and eight known phragmalin-type limonoids (14–21). Their structures were elucidated by using spectroscopic techniques and HRESIMS experiment. Compounds 6 and 17 displayed potent protein tyrosine phosphatase 1B inhibitory activity with IC50 values of 1.2 ± 0.1 and 8.1 ± 0.5 μM, respectively.

Agledulines A-K, eleven previously undescribed limonoids, including eight biogenic A/D-rings-seco limonoid analogs (agledulines A-H), one D-ring-seco limonoid (agleduline I) and two A-ring-seco limonoids with a rare Δ

Aims Swietenia macrophylla have been considered for the treatment of various diseases, including anticancer activity. This study aimed to investigate the anticancer activity of S. macrophylla leaves extract and its isolated compound towards human colorectal cancer cell line. Main methods Hexanic extract of S. macrophylla leaves demonstrated relevant cytotoxicity only against colon cancer cell line HCT116. Key findings Our results showed significant DNA damage and apoptosis after treatment with the hexanic extract of S. macrophylla. Moreover, no toxicity was noticed for the animal model. The isolated compound limonoid L1 showed potent cytotoxicity against cancer cell lines with IC50 at 55.87 μg mL−1. Limonoid L1 did not trigger any cell membrane rupture in the mice erythrocytes suggesting no toxicity. The antiproliferative effect of L1 was confirmed in colorectal cancer cells by clonogenic assay, inducing G2/M arrest, apoptosis, and DNA damage in cancer-type cells. Significance L1 reduced BCL2 and increased ATM, CHK2, TP53, ARF, CDK1, CDKN1A, and CASP3 in the colorectal cancer cell line. These findings suggest that limonoid L1 isolated from S. macrophylla can be a promising anticancer agent in managing colorectal cancer.

Doxorubicin (DOX) is an anthracycline antibiotic used in the fight against many types of cancer. Although it is quite effective for this purpose, its clinical use is limited by its severe side effects, highlighting the relevance of efforts to identify substances that act to minimize these effects. In this work, we sought to verify the ability of andiroba oil (AO) and a nanoemulsion of andiroba oil (AN) to lessen the side effects of DOX. The animals were separated into 7 groups with 6 animals each: mice treated with AO (2000 mg/kg), AN (2000 mg/kg), the antineoplastic agent DOX (40 mg/kg), AO+DOX, AN+DOX and solvent controls was used of negative control (corn oil and nanoemulsion surfactant). AO and AN were administered for 14 consecutive days orally by gavage and on the 13th day, applied DOX by intraperitoneal route (i.p.), in order to evaluate the protective potential of andiroba. The animals were euthanized on the 15th day. Hematological, biochemical, histological, and immunohistochemical parameters were analyzed. Andiroba reduced several aspects of the severity of lesions caused by DOX, decreasing hematotoxicity and the severity of histological changes in the liver and kidneys, and reducing the frequency of apoptotic cell death. In many cases, AN showed greater efficacy than AO alone, reflecting the feasibility of using this nanotechnology to improve the pharmacokinetics of lipid compounds in the body. The study sheds new light on the therapeutic benefits of andiroba and suggests new ways for investigating how the quantity and quality of lipid compounds affect exposed organisms.

Eleven undescribed limonoids, cipacinerasins A-K, involving of four diverse carbon skeletal types, along with fifteen known analogues, were isolated from the branches and leaves of Cipadessa baccifera. Within them, cipacinerasins A and B feature a rearranged tetrahydropyranyl ring B formed between C-8 and C-30, are unusual miscellaneous-type limonoids. Cipacinerasins E and F are rare trijugin-type limonoids, of which the D-ring δ-lactone is cleaved. Their structures were elucidated on the basis of extensive spectroscopic data (HRESIMS, NMR, UV and IR), electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. All compounds were evaluated in vitro cytotoxicity against five human tumor cell lines (K562, HeLa, PC3, LN-Cap and Hell), and cipacinerasin E showed moderate antitumor activity with IC

Three prieurianin-type limonoids (1-3), including two new compounds (1 and 2) and one known compound (3) were isolated from Munronia henryi. These compounds were tested for their activities against tobacco mosaic virus (TMV) by the conventional half-leaf method and the outcomes were analyzed by western blotting and RT-PCR assays. The three tested compounds, at 100 μg/mL, showed strong antiviral activities in the pretreated tobacco plants with inhibition rates ranging from 70.5% to 81.3%, which were significantly higher than that of the positive control, ningnanmycin (55.6%). Their potential of inducing systemic acquired resistance (SAR) was also evaluated, in which compound 1 showed excellent induction activities. Furthermore, it was found that potentiation of defense-related enzyme activity and the contents of SA was increased. Compound 1 could also inhibit the expression of TMV CP and up-regulate the expression of defense-related genes. This work revealed that these limonoids, especially compound 1 could induce resistance in tobacco plants against the viral pathogen TMV. Meanwhile, compounds 1-3 could down-regulate the expression of NtHsp70-1 and Nthsp70-261 genes, indicating that these limonoids possibly inhibit TMV infection by suppressing NtHsp70-1 and Nthsp70-261 expression. This study is the first to report antiviral compounds with two different mechanisms of action.

A Carapa guianensis, conhecida popularmente como andiroba, pertence à família das plantas Meliaceae. O óleo extraído da semente da andiroba é espesso, de cor amarelo-escura, e é utilizado como matéria-prima para iluminação de lamparinas e na indústria de cosméticos para fabricação de loções, xampus, cremes e sabonetes. Além disso, a andiroba também possui atributos terapêuticos e farmacológicos, com propriedades genotóxicas, anti-helmínticas, cicatrizantes, tripanocidas, leishmanicidas, repelentes, larvicidas, antialérgicas, anti-inflamatórias, acaricidas, antimaláricas, antioxidantes e antitumorais. O presente trabalho revisou as propriedades médicas, terapêuticas e farmacológicas de Carapa guianensis. Quanto à atividade genotóxica, não foi encontrada toxicidade ao DNA dos animais testados. Os compostos responsáveis pela atividade curativa no óleo de semente foram tanininos, saponinas e alcalóides. Não foram encontrados compostos responsáveis pela atividade tripanocida. Os compostos responsáveis pela atividade leishmanicida foram ácidos graxos e compostos fenólicos. Não foram encontrados compostos responsáveis pela atividade repelente e larvicida. Tetranortriterpenóides foram considerados responsáveis pela atividade anti-alérgica e anti-inflamatória. Não foram encontrados compostos responsáveis pela atividade acaricida. 6α- acetoxiquedunina foi o composto responsável pela atividade antimalárica. Na atividade antioxidante e antitumoral do óleo de semente não foram encontrados compostos envolvidos.

Six rocaglaol derivatives were isolated from Dysoxylum gotadhora, and those compounds showed good cytotoxic activity with IC50 values ranging from 10 to 350 ng/mL against five different cancer cells. Obviously, further total synthesis of rocaglaol derivatives for medical chemistry study is of great significance. Then, twenty six rocaglaol derivatives including 25 new compounds were designed, synthesized, and evaluated for their cytotoxic activities against three human cancer cell lines: human colon cancer cells (HCT116), colorectal cancer stem cells (P6C), and human red leukocyte leukemia cells (HEL), using MTT assay. Most of derivatives showed good cytotoxic activities, with the lowest IC50 being 3.2 nM for HEL cells, which was 169 times stronger than that of the positive control (doxorubicin). Further mechanism study indicated that 11k could significantly suppress MAPK pathway in HCT116 cells, which may responsible for induction of apoptosis and cell cycle arrest.

Eleven undescribed triterpenoids (pentandrucines A to K) were isolated from the n-hexane extract of the stem bark of Chisocheton pentandrus (Blanco) Merr. These comprised ten undescribed dammarane-type triterpenoids and one undescribed apotirucallane-type triterpenoid. Additionally, two dammarane-type triterpenoids, four apotirucallane-type triterpenoids and two tirucallane-type triterpenoids were also isolated. The chemical structures of pentandrucine A-K, were fully elucidated using 1D and 2D-NMR, and high resolution MS. All of the compounds were evaluated for cytotoxic activity against MCF-7 breast cancer cells in vitro. Melianodiol proved to be the most active with an IC50 of 16.84 μM comparing favourably with Cisplatin (13.2 μM).

Les graines de Entandrophragma cylindricum germent difficilement entre 5 jours et un mois et atteignent rarement des pourcentages de germination de 30 %. La detegumentation des graines ameliore la germination. L'embryon isole place dans les memes conditions de germination peut atteindre des valeurs de 50 % en trois semaines. Les traitements par l'acide sulfurique ameliorent le pourcentage de germination de ces graines. Il en est de meme pour l'acide gibberellique qui non seulement stimule la capacite germinative, mais raccourcit les delais de germination. Le pourcentage de germination le plus eleve est obtenu au bout de 15 jours avec l'acide gibberellique alors qu'il faut plus de temps avec le temoin (eau distillee). Les traitements combinant l'acide sulfurique, l'acide gibberellique et la cellulase suivis d'un sechage se revelent etre les meilleurs traitements. Ils ont permis d'atteindre 91 % des graines germees.

Eleven previously uncharacterized steroids, along with three analogs were isolated from Aglaia lawii leaves. Their structures were definitely characterized by the methods of NMR, MS, IR, ECD and X-ray crystallography study. Among these unreported compounds, 3-epi-dyscusin C, 3-epi-lansisterone E and (Z)-2α-hydroxyaglawone were C-21 pregnane steroids incorporating a highly oxygenated ring A, while others were Δ5-3β-hydroxy-7-ketosteroids bearing different ring D and C-17 aliphatic chains. All isolates were evaluated for nitric oxide (NO) inhibitory activities. 3-Epi-dyscusin C, 3-epi-lansisterone E, (Z)-2α-hydroxyaglawone and 17(20)E-dyscusin B showed significant anti-inflammatory activities with IC50 values of NO inhibition less than 10 μM (in the range from 4.47 ± 0.36 to 7.67 ± 0.46 μM).

Nine new limonoids, named thaixylomolins S–Z (1–8) and 2-O-acetylthaixylomolin Z (9), were isolated from seeds of the mangrove, Xylocarpus moluccensis, collected in the mangrove swamp of Trang Province, Thailand. Thaixylomolin S (1) is the fourth member of the khayalactone class of limonoids containing a hexahydro-2H-2,5- propanocyclopenta[b]furan motif. Thaixylomolins T–Y (2–7) are structurally diverse mexicanolides; whereas thaixylomolin Z (8) and 2-O-acetylthaixylomolin Z (9) are phragmalin 8,9,30-orthoesters. The structures of these compounds were established by HRESIMS and extensive 1D and 2D NMR investigations. The absolute configurations of thaixylomolins S (1), U (3), and Z (8) were unambiguously established by single-crystal X-ray diffraction analyses, conducted with Cu Kα radiation; whereas that of 2-O-acetylthaixylomolin Z (9) was determined to be the same as that of thaixylomolin Z (8) by the accurate fit of their experimental electronic circular dichroism spectra. Thaixylomolin S (1), featuring the presence of a 30-(2′-methyl)butyryloxy group, is the first limonoid of the khayalactone class, whose constitution and absolute configuration are unequivocally determined by X-ray crystallography. The inhibitory activities of all the compounds, except for the epimers 4, were assayed against human carboxylesterase 2. All the tested compounds exhibited inhibition rates in the range of 16–65% at the concentration of 100.0 μM.

The phytochemical exploration of the Entandrophragma candollei stem bark extract led to the isolation and identification of twenty compounds including three undescribed phragmalin-class limonoids named encandollens C-E (1-3), the undescribed protolimonoid 5 together with sixteen known compounds. The structures of all the isolated compounds were determined by interpretation of their spectroscopic and spectrometric data including HRMS, 1D and 2D NMR analyses. The assignment of the absolute and relative stereochemistry of the undescribed compounds was achieved using SC-XRD analyses as well as NOESY experiments. The previously reported structure of odoratone (5a) was corrected as 23R,24S-dihydroxy-22S,25-epoxytirucall-7-en-3-one (5) based on its NMR and SC-XRD data. Prieurianin (4) exhibited high cytotoxic activity on KB3-1cell lines with an IC50 of 1.47muM compared to the reference griseofulvin (IC50=17-21muM). The results of the in silico docking of compound 4 supported and delivered further insights on its cytotoxicity. Copyright © 2020 Elsevier Ltd. All rights reserved.

Toona sinensis (A.Juss.) M.Roem., a multi-purpose tree of Meliaceae, is widely distributed and intensively cultivated in Asia, yet its high yielding, lipid-rich seeds are rarely exploited. The present study systematically analyzed the differences and correlations of seed morphological characteristics and fatty acid (FA) profiles of 62 representative T. sinensis germplasms distributed across northern to southern China. T. sinensis seeds were rich in total FAs (TFA, 107.03-176.18 mg/g). Additionally, linoleic acid (54.69-100.59 mg/g), α-linolenic acid (ALA, 22.47-45.02 mg/g), oleic acid (OA, 5.12-23.94 mg/g), palmitic acid (6.87-14.14 mg/g), stearic acid (SA, 3.13-6.57 mg/g) and elaidic acid (1.70-2.88 mg/g) were the major FAs measured by GC/MS analysis. Size (average width of 3.94±0.01 mm and length of 5.79±0.02 mm) and mass (average thousand-seed weight of 10.52±0.17 g) were greater in T. sinensis seeds collected south than north of 30° latitude. These traits were also positively correlated with unsaturated FA content and negatively related to SA and saturated FA contents (P

The aim of this study was to evaluate the effects of Pterorhachis zenkeri (Meliaceae) on sex organ growth in immature male rats and, oxidative stress and apoptosis markers in CCL-97 (R2C) Leydig cells. For the in vivo studies, 70 immature male Wistar rats (n = 10/group) were treated for 2 or 4 weeks with: distilled water (10 ml/kg, per os) plus soya oil (1 ml/kg, sc), bicalutamide (10 mg/kg, per os), aqueous or methanol extract of P. zenkeri (10 mg/kg or 62 mg/kg, per os) or testosterone propionate (3 mg/kg, sc). After each treatment period, body and sexual organ weights, plasmatic testosterone, total proteins and total cholesterol levels were measured. In the in vitro test, the effects of the methanol extract of P. zenkeri on cell viability, apoptosis, reactive oxygen species (ROS) production, intracellular calcium release and caspases 3/9 were assessed using CCL-97 Leydig cells. Pterorhachis zenkeri extracts decreased sex organ weights, plasmatic testosterone and protein levels in rats. In the in vitro studies, P. zenkeri inhibited apoptosis, ROS production, calcium release and caspase 3/9 activities. These results suggest that P. zenkeri has anti-androgenic, anti-oxidant and anti-apoptotic activities with methanol extract being the most active and could be an effective alternative for the management of androgen-related diseases.

Three previously undescribed limonoids, fulvifomins A-C, together with two known compounds, 6-deoxydetigloyl-swietenine acetate and methyl angolensate, were isolated from fruiting bodies of the wood-rot fungus Fulvifomes xylocarpicola (Hymenochaetaceae), growing on the mangrove tree Xylocarpus granatum (Meliaceae). The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data, and X-ray crystallographic analysis (for fulvifomin A). A number of similar limonoids have been isolated from higher plants of the family Meliaceae, including X. granatum. The present study represents a unique evidence that the associated basidiomycete also contains these limonoids. Fulvifomin B exhibited moderate antimalarial and antitubercular activites.

Toosendanin, bearing a furan ring, is a limonoid belonging to the group of tetranortriterpenoids. Toosendanin is a phytochemical found in the medicinal plant Melia toosendan Sieb. et Zucc. of the Meliaceae family. Toosendanin and its derivatives demonstrate high insecticidal activity and are important pesticides derived from plants. Despite intensive investigation of limonoids over several decades, the biosynthetic pathway of these triterpenoids is less understood. To identify the key enzymes involved in the toosendanin biosynthetic pathway, we analyzed the contents of toosendanin in various plant tissues and parts and found that the highest level of toosendanin was found in the developing fruit and gradually decreased as the fruit matured. More than 346 116 transcripts were assembled based on 394 million paired-end Illumina reads and 6 million PacBio reads from the pooled RNA samples of fruits, leaves and young barks. A total of 186 263 genes were predicted. Six 2,3-oxidosqualene cyclase (OSC) genes were identified by analyzing the association between gene expression and metabolite profiles. Functional analyses using the Nicotiana benthamiana transient expression assay showed that MtOSC1 catalyzed 2,3-oxidosqualene to produce a tetracyclic triterpene skeleton, tirucalla-7,24-dien-3β-ol, which is predicted as the precursor for toosendanin biosynthesis. We identified another OSC, MtOSC6, which is a lupeol synthase. Using synthetic biology methods, these identified enzymes could be used to model a biosynthetic pathway to produce large quantities of toosendanin.

Four previously undescribed steroids, identified as (3S,7S,8S,9S,10R,13S,14S,16S,17R,20S)-7α-methoxy-ergosta-5,24(28)-dien-3β,16β,20-triol (1), ergosta-5,24(28)-dien-3β,7α,16β-triol (2), ergosta-5,25-dien-3β,7α,16β,20-tetrol (3) and 7α,16β,24α-trihydroxy-varninasterol (4), as well as five known analogues (5–9), were isolated from the leaves and twigs of Dysoxylum pallens Hiern (Meliaceae). Their structures were elucidated based on extensive spectroscopic analysis such as HR-ESI-MS, 1D and 2D NMR, UV, and IR. The absolute configuration of compound 1 was determined by X-ray diffraction analysis. Selected compounds were evaluated for their cytotoxic activities. Compounds 1, 2, and 8 exhibited moderate cytotoxic activity against HL-60, Hela, and HepG2 tumor cell lines with IC50 ranged from 11.09 to 17.51 μM.

BackgroundConcomitant exposure to environmental/occupational toxicants such as aflatoxin B1 (AFB1) and arsenic in some regions of the world has been well reported. Therefore, this calls for the assessment of the efficacy of agents such as phytochemicals, which are already known for their ethno-medicinal uses in prophylaxis/remediation. We investigated the possible cytotoxic bio-interactions between AFB1 and sodium arsenite (SA) in urinary bladder cells. We also assessed the cytoprotective effects of curcumin and the ethanol stem bark extract of Khaya senegalensis (K2S).MethodsThe cells were exposed to graded levels of AFB1, SA, curcumin, and K2S for 24, 48, and 72 h. Subsequently, using optimum toxic concentrations of AFB1 and SA, respectively, the influence of non-toxic levels of curcumin and/or K2S was tested on exposure of the cells to AFB1 and/or SA. Hoechst 33342/propidium iodide staining technique was used to determine the end-points due to cytotoxicity with changes in adenosine triphosphate (ATP) levels determined using Promega’s CellTiter-Glo luminescent assay.ResultsCo-treatment of the cells with AFB1 and SA resulted in synergy in cytotoxic effects. Cytotoxicity was reduced by 3.5- and 2.9-fold by pre-treatment of the cells with curcumin and K2S before treatment with AFB1, while post-treatment resulted in 1.1- and 2.6-fold reduction, respectively. Pre-exposure of the cells with curcumin and K2S before treatment with SA ameliorated cytotoxicity by 3.8- and 3.0-fold, but post-treatment caused a 1.2- and 1.3-fold reduction, respectively.ConclusionsPre-treatment of the cells with either curcumin or K2S exhibited cytoprotective effects by ameliorating AFB1- and SA-induced cytotoxicity with inferred tendencies to prevent carcinogenesis.

Aglaia is the largest genus in the Meliaceae family (also known as Mahagoni in Indonesia), consisting of over 150 species, of which 65 are indigenous to Indonesia. These species spread through the tropical regions, especially Southeast Asia as well as the Nothern part of Australia, and have been used in traditional medicine for the treatment of several diseases. However, preliminary chemical researches commenced in 1965, where dammarane-type triterpenoids, aglaiol was isolated, and the structure was determined by chemical reaction and spectroscopic methods. Several studies have been carried out on the stembark, bark, leaves, seeds and leaves in the last fifty five years, and about 291 metabolites have been isolated from the sesquiterpenoid, diterpenoid, triterpenoid, limonoid, steroid, lignan, and alkaloid groups, as well as flavagline, which known to be the largest. This specifically amounts to 34% of Aglaia species, reported to show cytotoxic and insecticidal potentials, and also the tendency for use as chemical markers for this species. The extracts and compounds obtained from Aglaia species are evaluated for potential biological activities, including cytotoxicity, insecticidal, anti-inflammatory, antifungal, molluscicidal, antituberculosis and antiviral effects. In addition, flavagline (rocaglamide) derivatives have been confirmed to exhibit exceptional cytotoxicity, and are, thus, considered lead compounds for further development. Therefore, the results support the concept of utilizing Aglaia species as a potential source for the production of biologically active compounds.

In many Asian countries, herbs are used to treat disease. However, herbs also have adverse effects. Herb-induced liver injury has become a serious public health problem requiring urgent attention. The seeds of Swietenia macrophylla, a member of the family Polygonaceae, are often called skyfruit. We recently encountered a case of liver injury caused by skyfruit. The patient suffered from hepatocellular injury. We applied the updated Roussel Uclaf Causality Assessment Method (RUCAM) and the results indicated a highly probable relationship with skyfruit (total score 10). Moreover, we summarize another six cases of skyfruit-induced liver injury from the literature. The aim of our report is to help clinicians become more aware of the potential hepatotoxic effects of skyfruit and to accurately describe the clinical and laboratory characteristics of skyfruit-induced liver injury.

Neem fruit (Azadirachta indica A. Juss.) are popularly used to treat infections, diarrhea, fever, bronchitis, skin diseases, infected burns and hypertension. Although the antinociceptive and anti-inflammatory potential of A. indica has already been investigated in experimental models of pain and inflammation in mice, the current research is the first to report the evaluation of the capacity of A. indica fruit ethanolic extract (EtFrNeem) in acute pain attenuation using the adult zebrafish (Danio rerio) as an alternative model to the use in rodents. EtFrNeem was submitted to antioxidant action, preliminary chemical prospecting, FT-IR and determination of phenol and flavonoid content tests. Subsequently, EtFrNeem was tested for acute nociception and abdominal inflammation, locomotor activity, and acute toxicity in adult zebrafish. Possible neuromodulation mechanisms were also evaluated. EtFrNeem showed low antioxidant activity, but was shown to be rich in flavonoids. EtFrNeem showed no anti-inflammatory action, did not alter the locomotor system, and it was not toxic. However, EtFrNeem significantly reduced the nociceptive behavior induced by formalin, glutamate and acidic saline, when compared to the control group. These effects of EtFrNeem were significantly similar to those of morphine, used as a positive control. The antinociceptive effect of EtFrNeem was inhibited by naloxone, ketamine and amiloride. EtFrNeem has the pharmacological potential for acute pain treatment and this effect is modulated by the opioid system, NMDA receptors and ASICs channels. These results lead us to studies of isolation and characterization of EtFrNeem bioactive principles, using adult zebrafish as an experimental model.

Nine new limonoids, named krishnagranatins A–I (2–5, 6a, 6b, and 7–9), were obtained from the seeds of an Indian mangrove, Xylocarpus granatum, collected at the swamp of Krishna estuary, Andhra Pradesh, together with the known one, granatumin X (1). The structures of these limonoids were established by HRESIMS, extensive NMR spectroscopic data, and single-crystal X-ray crystallography. The absolute configurations of 1, 2, and 9 were unequivocally determined by single-crystal X-ray diffraction analyses, obtained with Cu Kα radiation. Six new limonoids, including 2–5, 6a, and 6b, belong to a small group of limonoids with a C1–O–C29 oxygen bridge. Compounds 2 and 5 possess a 9-OH group, whereas 3–5 contain endo-conjugated Δ8,30 and Δ14,15 double bonds. Compounds 6a and 6b are a pair of new limonoid C29-epimers with the different orientation of a 29-OH group, of which the methylation leads to the chiral separation in high performance liquid chromatography (HPLC) and then affords two previously reported limonoids, sundarbanxylogranin C (6'a) and moluccensin W (6'b). Compounds 7–8 are two highly acetylated phragmalin-type limonoids, whereas 9 is a phragmalin 8,9,30-ortho ester. Compounds 7–9 exhibited inhibitory activity against the activation of NF-κB induced by lipopolysaccharide (LPS), but showed no obvious toxicity on RAW264.7 macrophage cells at the concentration of 10.0 μM.

Beverages containing Trichilia catigua are commonly employed in folk medicine. T. catigua bark extracts possess antioxidant, anti-inflammatory, and bactericidal properties. These properties suggest T. catigua bark extracts as a potential treatment for inflammatory bowel diseases (IBD). Using the 2,4,6-trinitrobenzenesulphonic acid (TNBS)-induced model of colitis in rats we evaluated the effect of an ethyl-acetate fraction (EAF) of T. catigua (200 mg/kg) administered by daily oral gavage or intrarectally at different time points after TNBS challenge. TNBS treatment evoked severe colonic inflammation after 24 h that persisted for 7 days, characterized by weight loss, high levels of myeloperoxidase activity, histological and macroscopic damage, and elevated index of oxidative stress in the blood. T. catigua EAF treatment prevented the oxidative stress within 24 h and enhanced tissue recovery observed at day 7, returning histological and macroscopic damage levels to that of the control group. TNBS treatment led to loss of myenteric neurons after 28 days. T. catigua EAF was unable to prevent the neuronal loss. Oral delivery of T. catigua EAF was more effective than intrarectal administration of the extract. In conclusion, T. catigua EAF treatment normalized oxidative stress parameters in blood and reduced the degree of acute inflammation in TNBS colitis.

Polysaccharides are the main active component of the Mongolian medicine Fructus Meliae Toosendan, but their effective extraction and antioxidant effects have not been reported. Therefore, the optimization of the microwave extraction of polysaccharides from Fructus Meliae Toosendan (FMTP) using the response interface method was carried out. Single-factor tests on four main factors (the solid–liquid ratio, microwave power, extraction time, and number of extractions) affecting the polysaccharide extraction rate in the microwave extraction process were carried out. Then, using the FMTP content as a response index, central composite tests on the four factors were conducted, and an optimization analysis using the response surface method was completed. Consequently, we obtained the optimum conditions for FMTP microwave extraction: a solvent–material ratio of 30.00 mL/mg, extraction power of 700 W, extraction time of 20 min, and two extractions. The FMTP extraction rate was 15.75% at the optimum conditions, consistent with the theoretical predictions. The crude polysaccharide was further purified to obtain high-purity FMTP polysaccharide, having a weight-average molecular mass of 1288 Da. The antioxidant activities of FMTP were evaluated using the hydroxyl superoxide anion, 2,2-diphenyl-1-picrylhydrazyl (DPPH), and nitrite free radical scavenging assays and reducing power assay. The data show that FMTP has considerable antioxidant activity. Thus, polysaccharides from Fructus Meliae Toosendan could be used as a potential antioxidant agent in medicine or as a functional food.

Leishmaniasis is a complex of diseases caused by protozoa of the genus Leishmania and affects millions of people around the world. Several species of plants are used by traditional communities for the treatment of this disease, among which is Carapa guianensis Aubl. (Meliaceae), popularly known as andiroba. The objective of the present work was to conduct a chemical study of C. guianensis seed oil and its limonoid-rich fractions, with the aim of identifying its secondary metabolites, particularly the limonoids, in addition to investigating its anti-Leishmania potential. The chemical analyses of the C. guianensis seed oil and fractions were obtained by electrospray ionization mass spectrometry (ESI-MS). The cytotoxic activity was tested against peritoneal macrophages, and antileishmanial activity was evaluated against promastigotes and intracellular amastigotes of Leishmania amazonensis. All the C. guianensis seed oil samples analyzed exhibited the same pattern of fatty acids, while the limonoids 7-deacetoxy-7-hydroxygedunin, deacetyldihydrogedunin, deoxygedunin, andirobin, gedunin, 11β-hydroxygedunin, 17-glycolyldeoxygedunin, 6α-acetoxygedunin, and 6α,11β-diacetoxygedunin were identified in the limonoid-rich fractions of the oil. The C. guianensis seed oil did not exhibit antileishmanial activity, and cytotoxicity was higher than 1000 μg/mL. Three limonoid-rich oil fractions demonstrated activity against promastigotes (IC50 of 10.53±0.050, 25.3±0.057, and 56.9±0.043μg/mL) and intracellular amastigotes (IC50 of 27.31±0.091, 78.42±0.086, and 352.2±0.145 μg/mL) of L. amazonensis, as well as cytotoxicity against peritoneal macrophages (CC50 of 78.55±1.406, 139.0±1.523, and 607.7±1.217 μg/mL). The anti-Leishmania activity of the limonoid-rich fractions of C. guianensis can be attributed to the limonoids 11β-hydroxygedunin and 6α,11β-diacetoxygedunin detected in the chemical analysis.