Two new limonoids from Melia toosendan

Two new limonoid-type triterpenoids, named 12-o-ethyl-l-deacetylnimbolinin B and 1-o-tigloyl-1-o-debenzoylohchinal, have been isolated from the fruit of Melia toosendan Sieb. et Zucc. Their structures were elucidated by spectral methods, including 2D-NMR spectra.

New limonoids from the fruits of Melia toosendan

Two new limonoids,1α-tigloyloxy-3α-acetoxyl-7α-hydroxyl-12α-ethoxyl nimbolinin（1） and lα-benzoyloxy-3α-acetoxyl-7α- hydroxyl-12α-ethoxyl nimbolinin（2）,were isolated from the fruits of Melia toosendan.Their structures were established on the basis of various NMR spectroscopic analyses,including 2D-NMR techniques（HSQC,HMBC,NOESY） and HR-ESI-MS.

Cipatrijugin G,a new trijugin-type limonoid bearing an uncommonγ-hydroxybutenolide unit from the aerial parts of Cipadessa cinerascens

A new trijugin-type limonoid,cipatrijugin G(1),together with the related known cipatrijugin A(2),were isolated from the aerial parts of Cipadessa cinerascens.The structure of the new compound was determined by extensive analysis of its spectroscopic data and by comparison of its NMR data with those reported in the literature.Compound 1 showed cytotoxicity against tumor cell line A549 with an IC_(50) value of 9.78μM.This is the first report of a trijugin-type limonoid bearing aγ-hydroxybutenolide unit,in comparison to the common furan unit as ring E.

Highly Oxygenated Limonoids and Lignans from Phyllanthus flexuosus

Two new highly oxygenated limonoids,flexuosoids A(1)and B(2),and three new arylnaphthalene lignan glycosides,phyllanthusmins D–F(3–5),were isolated from the roots of Phyllanthus flexuosus,in addition to three known lignans,phyllanthusmin C,arabelline,and(?)-diasyringaresinol.Their structures were elucidated on the basis of detailed spectroscopic analysis and chemical methods.Compounds 1 and 2,two new decaoxygenated limonoids with a C-19/29 lactol bridge and heptaoxygenated substituents at C-1,C-2,C-3,C-7,C-11,C-17,and C-30,represent the second example of limonoids in the Euphorbiaceae family.Most of the isolates were tested for their antifeedant,anti-herpes simplex virus 1,and cytotoxic activities.The new limonoids 1 and 2 showed promising antifeedant activity against the beet army worm(Spodoptera exigua)with EC50 values of 25.1 and 17.3 lg/cm2,respectively.In addition,both of them displayed moderate cytotoxicity against the ECA109 human esophagus cancer cell line,along with the known lignan glycoside,phyllanthusmin C,with the IC50 values of 11.5(1),8.5(2),and 7.8(phyllanthusmin C)lM,respectively.

Five new mexicanolide type limonoids from Heynea trijuga

Five new mexicanolide-type limonoids,heytrijunolides A-E(1-5)were isolated from the branches and leaves of Heynea trijuga.The structures of these new compounds were elucidated on the basis of extensive spectroscopic analysis.Compound 3 showed weak cytotoxicity against HL-60,SMMC-7721 and A-549 human tumor cell lines with the IC50 values of 21.88,20.66 and 12.70μM,respectively.

A New Limonoid from the seed of Aphanamixis polystachya

A new limonoid named rohituka-15 1, with a known limonoid dregeana-1 2, was isolated from the seed of Aphanamixis polystachya (Meliaceae). The 13C NMR data assignment of dregeana-1 2 and the structural elucidation of the new compound 1 were based on spectral analysis including 1H-1H COSY, HMQC and HMBC experiments.

Limonoids and triterpenoids from the twigs and leaves of Dysoxylum hainanense

Four new limonoids,dysohainanins A-D(1-4),and two new triterpenoids,dysohainanins E and F(5 and 6),together with seven known ones were isolated from the twigs and leaves of Dysoxylum hainanense Merr.The structures of the new compounds were determined by a variety of spectroscopic methods.The cytotoxic activities of these compounds were evaluated,and the known compound ent-19-nor-4,16,18-trihydroxy-8(14)-pomaren-15-one(13)showed in vitro cytotoxicity against HL-60,A-549,MCF-7,and SW480 cells,with IC50 values of 24.3,28.1,30.7,and 22.5mM,respectively.Compounds 2 and 3 were tested their insecticidal activities using brine shrimp and both of them were inactive.

Diterpenoids and Limonoids from the Leaves and Twigs of Swietenia mahagoni

Three new compounds,including two diterpenoids,nemoralisins H and I(1 and 2),and a limonoid,2-methoxy khayseneganin E(3),along with four known constituents(4-7),were isolated from the leaves and twigs of Swietenia mahagoni.Their chemical structures were elucidated by means of spectroscopic analysis.The cytotoxities of these isolated constituents were assayed.

Limonoid and Steroidal Saponin from Azadirachta indica

A new limonoid,17-(5-methoxy-2-oxofuran-3-yl)-28-deoxonimbolide(1),and a new C21 steroidal saponin,2a,4a-dihydroxy-pregn-5-en-16-one-3a-O-D-glucopyranoside(2),together with 11 known compounds were isolated from the methanol extract of the leaves of Azadirachta indica.The structures were elucidated by means of spectroscopic analysis and putative biosynthetic origins.All the compounds were evaluated for their antibacterial activities against six bacterial strains.

Four New Limonoids from the Barks of Toona ciliata

Four new limonoids,toonayunnanaes F−I(1−4),and six known compounds(5−10)were isolated from the barks of Toona ciliata.Their structures were elucidated by thoroughly analyzing of NMR and HRMS data,and single-crystal X-ray diffraction of 1.The oxetane ring moiety in 1 was rare in limonoids and other natural products.Compound 1 showed nitric oxide(NO)inhibitory effect with an IC5038.45±0.41μM in lipopolysaccharide(LPS)-activated RAW 264.7 macrophages.

<i>Seco</i>-limonoid 11<i>α</i>,19<i>β</i>-dihydroxy-7-acetoxy-7- deoxoichangin promotes the resolution of <i>Leishmania panamensis</i>infection

The high morbidity generated by the infection caused by parasites of the genus Leishmania, make of this infection into one of the vector-borne infectious diseases most relevant worldwide, which added to the fact that the drugs used for its treatment are far from be optimal and considering that prophylactic approaches (such as the development of a vaccine) still seems far from being achieved, make of the search for new therapeutic alternatives for safe and effective treatment of this disease one of the most accurate approaches to the control of this disease. In this study we evaluated the antileishmanial and immunomodu- latory activity of the compound 11α,19β-dihydroxy- 7-acetoxy-7-deoxoichangin (a seco-limonid molecule) through: 1) evaluation of its cytotoxicity over promastigotes and axenic amastigotes of L. (V) panamensis, 2) determination of its ability to induce the control of in vitro infection, using infected murine cells (J774.2) and human dendritic cells (hDCs), 3) quantifying the levels of pro-inflammatory cytokines, (iv) evaluating the expression of cell markers associated with hDCs maturation, and (v) determinating the production of nitric oxide free radicals (NO). In this regard, this seco-limonoid exhibited an antileishmanial activity represented in the reduction of in vitro infection in J774.2 cells and hDCs, with a EC50 of 7.9 μM (4.48 μg/mL) and 25.5 μM (14.39 μg/mL), respectively, and additionally, we observed an increase on the production of IL-12p70, TNF-α and NO, as also, in the number of hDCs HLA-DR-positive in treated infected hDCs. These findings suggest that anti-lei- shmanial activity of this compound could be associated with the potential “reactivation” of phagocytic cell that is “paralyzed” by the infection, generating an immune phenotype associated with protection.

4种柑橘籽油脂肪酸组成及生物活性成分

以瓯柑籽、椪柑籽、香橙籽、胡柚籽为原材料,通过索氏提取法提取油脂,利用气相色谱和高效液相色谱分别对4种油脂样品的脂肪酸以及主要的柠檬苦素类化合物、类黄酮类化合物含量进行测定分析。结果表明,4种柑橘籽油的脂肪酸主要由油酸(19.7%~49.0%)、亚油酸(17.93%~45.93%)、棕榈酸(23.04%~27.73%)以及少量的亚麻酸(1.327%~5.103%)和硬脂酸(3.437%~4.797%)组成。生物活性成分柠檬苦素、诺米林、奥巴叩酮、橙皮苷、柚皮苷含量分别为24.79~753.75、266.57~915.62、61.95~496.08、15.61~17.57、27.84~30.01μg/g。柑橘籽油不仅脂肪酸比例合理,还含有较丰富的黄酮及柠檬苦素类化合物,作为植物油原料具有开发潜力。

New limonoids isolated from the bark of Melia toosendan

Two new limonoids, 12-ethoxynimbolinins G and H(compounds 1 and 2), and one known compound, toosendanin(Chuanliansu)(compound 3), were isolated from the bark of Melia toosendan. Their structures were elucidated by spectroscopic analysis and X-ray techniques. The absolute configuration of toosendanin(3) was established by single-crystal X-ray diffraction. Compounds 1-3 were evaluated for their cytotoxicity against five tumor cell lines.

Two new phragmalin-type limonoids orthoesters from Entandrophragma candollei

Two new phragmalin-type limonoids orthoesters, encandollens A and B(1 and 2), were isolated from the stem barks of Entandrophragma candollei collected in Ghana. The structures of these compounds were elucidated on the basis of HR-ESI-MS, ~1 H and ^(13) C NMR, HSQC, HMBC, and ROESY data. Compound 1 was a rare C-15 enolic acyl phragmalin-type limonoid orthoester. Compounds 1 and 2 exhibited weak inhibitory effects on NO production in lipopolysaccharide(LPS)-induced RAW 264.7 cells.

Two new limonoids isolated from the fuits of Melia toosendan

In the present study, two new limonoids, 1α, 7α-dihydroxyl-3α-acetoxyl-12α-ethoxylnimbolinin(1) and 1α-tigloyloxy-3α-acetoxyl-7α-hydroxyl-12β-ethoxylnimbolinin(2), together with other four known limonoids(3-6), were isolated from the fruits of Melia toosendan. Their structures were elucidated by means of extensive spectroscopic analyses(NMR and ESI-MS) and comparisons with the data reported in the literature. The isolated compounds were evaluated for their antibacterial activities. Compound 4 exhibited significant antibacterial activity against an oral pathogen, Porphyromonas gingivalis ATCC 33277, with an MIC value of 15.2 μg·m L-1. Compound 2 was also active against P. gingivalis ATCC 33277, with an MIC value of 31.25 μg·m L-1. In conlcusion, our resutls indicate that these compounds may provide a basis for future development of novel antibiotics.

Four New Limonoids from Aphanamixis grandifofia

Four new limonoids, named aphanagranins A-D （1-4）, were isolated from the fruits ofAphanamixis grandi- folia. The new structures were determined by spectroscopic methods especially 1D and 2D NMR analysis, Aphana- granin A （1） possessed a rare four membered oxygen heterocyclic ring and its absolute configurations were deter- mined on the basis of the signal crystal X-ray diffraction analysis. Furthermore, compounds 1 and 2 showed weak activity toward brine shrimp （Artemia salina）.

Cipaferoids A-C, Three Limonoids Represent Two Different Scaffolds from Cipadessa baccifera

Three limonoids cipaferoids A-C （1-3） representing two different scaffolds were isolated from Cipadessa baccifera. Their structures were completely assigned by spectroscopic data, CD exciton chirality method, and X-ray crystallography. Compounds 2 and 3 exhibited moderate antimalarial activity with IC50 values of 9.3±0.1 and 14.7±4.8 μmol·L^-1, respectively.

Dysoxylumasins A--F＂ Six New Limonoids from Dysoxylum mollissimum BI.

Six new mexicanolide-type limonoids, dysoxylumasins A-F （1-6）, together with eight known compounds, namely litseagermacrane, 15-methoxyisodauc-3-ene-1β, 5α-diol, isodauc-6-ene-10β,14-diol, 4-epi-isodauc-6-ene- 10β,14-diol, 2a,3a,4β-trihydroxypregnan-16-one, 1,7-phenanthrenedimethanol, spicatin, and aurantiamide, were isolated from the leaves and twigs of Dysoxylum mollissimum B1. Their structures were established by the analyses of spectroscopic data.

A new cytotoxic salannin-class limonoid alkaloid from seeds of Azadirachta indica A. Juss

A new cytotoxic salannin-class limonoid alkaloid, azadiramide A（1）,was isolated from seeds of Azadirachta indica A. Juss. Its structure was elucidated by extensive analysis of spectroscopic data and quantum chemical calculation. Compound 1 is a rare salannin-class limonoid alkaloid. To our best knowledge, only two compounds belonging to this type were so far found. It showed inhibitory activity against human breast cancer MDA-MB-231 cell line with IC_（50） value of 2.70±0.63 μmol/L.

Highly oxygenous trichilin-type limonoids from Trichilia sinensis

Six new trichilin-type limonoids(1-6)with C-19/29 lactol or acetal bridge and a new ring intact limonoid(7)were isolated from the desiccative ripe fruits of Trichilia sinensis.Their structures were determined by extensive spectroscopic methods including 1 H NMR,13 C NMR,HSQC,HMBC,ROESY experiments as well as HRESI-MS data.All isolated compounds were evaluated for toxicities against human pulmonary carcinoma A549 and Hela cell lines by sulforhodamine B(SRB)method.Compound 7 showed weak inhibitory activity in Hela cell line at 40μmol·L^-1.