Limonoids from Aphanamixis polystachya Leaves and Their Interaction with Hsp90

Planta Medica ◽  
2018 ◽  
Vol 84 (12/13) ◽  
pp. 964-970 ◽  
Author(s):  
César Muñoz Camero ◽  
Antonio Vassallo ◽  
Marinella De Leo ◽  
Abeer Temraz ◽  
Nunziatina De Tommasi ◽  
...  
Keyword(s):  
Molecular Chaperone ◽  
Natural Compounds ◽  
Spectroscopic Methods ◽  
Phytochemical Study ◽  
Phenolic Derivatives ◽  
New Compounds ◽  
Type 3 ◽  
First Time

AbstractA phytochemical study of n-hexane, CHCl3, and CHCl3-MeOH extracts of Aphanamixis polystachya leaves led to the isolation of 10 compounds. Five of them turned out to be new natural compounds, including two mexicanolide-type (1, 2) and three polyoxyphragmalin-type (3–5) limonoids, together with two known andirobin-type limonoids (6, 7) and three phenolic derivatives. The structures of the new compounds were established on the basis of spectroscopic methods to be 8-hydro-14,15-en-cabralin (1), 3-deacetyl-8-hydro-cabralin-14,15-en-3-one (2), 20,22-dihydroxy-21,23-dimethoxytetrahydrofuran khayanolide A (3), 1-deacetyl-3-dehydroxy-3-oxokhaysenelide E (4), and meliaphanamixin A (5). All compounds were isolated for the first time from this species. The ability of the isolated limonoids to interact with the molecular chaperone Hsp90 was tested. Compounds 6 and 7 were the most active.

scholarly journals Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae)

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4412 ◽  
Author(s):  
Yves Salomon Makong ◽  
Gervais Mouthé Happi ◽  
Judith Liliane Djouaka Bavoua ◽  
Jean Duplex Wansi ◽  
Lutfun Nahar ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Ethyl Acetate ◽  
Propionic Acid ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Phytochemical Study ◽  
Methanolic Extracts ◽  
New Compounds ◽  
Soluble Fractions ◽  
Mcf 7

A phytochemical study of the root and bark of Brucea antidysenterica J. F. Mill. (Simaroubaceae) afforded three new compounds, including a stilbene glycoside bruceanoside A (1), and two canthinone alkaloids bruceacanthinones A (3) and B (4), along with ten known secondary metabolites, rhaponticin (2), 1,11-dimethoxycanthin-6-one (5), canthin-6-one (6), 1-methoxycanthin-6-one (7), 2-methoxycanthin-6-one (8), 2-hydroxy-1,11-dimethoxycanthin-6-one (9), β-carboline-1-propionic acid (10), cleomiscosin C (11), cleomiscosin A (12), and hydnocarpin (13). The structures of all the compounds were determined using spectrometric and spectroscopic methods including 1D and 2D NMR, and HRSEIMS. The identities of the known compounds were further confirmed by comparison of their data with those reported in the literature. The root and bark methanolic extracts, the dichloromethane and ethyl acetate soluble fractions, and the isolated compounds (3–13), were assessed for their cytotoxicity against the cancer cell lines A-549, MCF-7, and PC-3. The results suggested that compounds in the extracts might possess a synergic action in their cytotoxicity.

Triazene derivatives of (1,x)-diazacycloalkanes. Part VII. Synthesis of a series of 1-aryl-2-[3-(3-[2-aryl-1-diazenyl]-1,3-diazepan-1-ylmethyl)-1,3-diazepan-1-yl]-1-diazenes from the reaction of diazonium salts with mixtures of formaldehyde and 1,4-diaminobutane

2006 ◽  
Vol 84 (10) ◽  
pp. 1434-1441
Author(s):  
Reid Tingley ◽  
Keith Vaughan
Keyword(s):  
Diazonium Salt ◽  
Diazonium Salts ◽  
The Novel ◽  
Cage Structure ◽  
X Ray Crystallography ◽  
New Compounds ◽  
Type 3 ◽  
Bicyclic Molecules

A new series of bistriazenes, the 1-aryl-2-[3-(3-[2-aryl-1-diazenyl]-1,3-diazepan-1-ylmethyl)-1,3-diazepan-1-yl]-1-diazenes (8), has been synthesized from the reaction of diazonium salts with a mixture of 1,4-diaminobutane and formaldehyde. All new compounds of series 8 have been characterized by IR and NMR spectroscopy, and the elemental composition of selected examples has been verified by elemental analysis. The connectivity of the series has been unequivocally determined by X-ray crystallography. The new bistriazenes are important because the structure contains the novel saturated heterocycle, 1,3-diazepane. The general conclusion of this study is that alkanediamines with three or four carbon atoms in the spacer link between the nitrogen atoms give rise to the linear bicyclic molecules of type 2, in contrast to the case of ethylenediamine (two carbon atoms in spacer link), which affords molecules of type 3, which exemplify the cage structure of type 1.Key words: diazonium salt, triazene, bistriazene, diazepane, formaldehyde, nuclear magnetic resonance.

Lupane-Triterpene Esters from the Leaves of Ceriops decandra (Griff.) Ding Hou

2005 ◽  
Vol 58 (8) ◽  
pp. 615 ◽  
Author(s):  
Chanita Ponglimanont ◽  
Pakakrong Thongdeeying
Keyword(s):  
Ursolic Acid ◽  
Betulinic Acid ◽  
Spectroscopic Methods ◽  
Ceriops Decandra ◽  
New Compounds ◽  
First Time ◽  
Triterpene Esters

Two novel triterpene esters were isolated from the leaves of Ceriops decandra in addition to 16 known triterpenes: lupenone 3, lupeol 4, betulinaldehyde 5, 3β-Z-coumaroyllupeol 6, 3β-E-coumaroyllupeol 7, 3-epi-betulinic acid 8, betulin 9, betulinic acid 10, 3β-E-feruloylbetulin 11, 30-nor-lup-3β-ol-20-one 12, 3β-E-caffeoyllupeol 13, lup-20(29)-en-3β,30-diol 14, 3β-hydroxylupan-29-oic acid 15, 3β,20-dihydroxylupane 16, and a mixture of oleanolic and ursolic acid 17 and 18. The new compounds were determined by spectroscopic methods to be 3β-E-feruloyllupeol 1 and 3β-Z-feruloyllupeol 2. Compounds 3 and 5–16 were reported for the first time as metabolites of C. decandra.

scholarly journals Antileishmanial Phenylpropanoids from the Leaves ofHyptis pectinata(L.) Poit

2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Rosangela A. Falcao ◽  
Patricia L. A. do Nascimento ◽  
Silvana A. de Souza ◽  
Telma M. G. da Silva ◽  
Aline C. de Queiroz ◽  
...  
Keyword(s):  
Rosmarinic Acid ◽  
Bacterial Infections ◽  
Ethanol Extract ◽  
Spectroscopic Methods ◽  
Etoh Extract ◽  
Promastigote Form ◽  
Water Fractions ◽  
New Compounds ◽  
First Time

Hyptis pectinata, popularly known in Brazil as “sambacaitá” or “canudinho,” is an aromatic shrub largely grown in the northeast of Brazil. The leaves and bark are used in an infusion for the treatment of throat and skin inflammations, bacterial infections, pain, and cancer. Analogues of rosmarinic acid and flavonoids were obtained from the leaves ofHyptis pectinataand consisted of two new compounds, sambacaitaric acid (1) and 3-O-methyl-sambacaitaric acid (2), and nine known compounds, rosmarinic acid (3), 3-O-methyl-rosmarinic acid (4), ethyl caffeate (5), nepetoidin A (6), nepetoidin B (7), cirsiliol (8), circimaritin (9), 7-O-methylluteolin (10), and genkwanin (11). The structures of these compounds were determined by spectroscopic methods. Compounds1–5, and7were evaluatedin vitroagainst the promastigote form ofL. braziliensis, and the ethanol extract. The hexane, ethyl acetate, and methanol-water fractions were also evaluated. The EtOH extract, the hexane extract, EtOAc, MeOH:H2O fractions; and compounds1,2and4exhibited antileishmanial activity, and compound1was as potent as pentamidine. In contrast, compounds3,5, and7did not present activity against the promastigote form ofL. braziliensisbelow 100 µM. To our knowledge, compounds1and2are being described for the first time.

scholarly journals A Pair of Novel Sulfonyl-Containing N-Acetyldopamine Dimeric Enantiomers From Aspongopus chinensis

2020 ◽  
Vol 15 (3) ◽  
pp. 1934578X2091127
Author(s):  
Li Liao ◽  
Yong-Ming Yan ◽  
Te Xu ◽  
Hou-Lin Xia ◽  
Yong-Xian Cheng
Keyword(s):  
High Performance Liquid Chromatography ◽  
Biological Activity ◽  
Liquid Chromatography ◽  
Renal Fibrosis ◽  
High Performance ◽  
Racemic Mixture ◽  
Spectroscopic Methods ◽  
Liquid Chromatography Separation ◽  
New Compounds ◽  
First Time

A pair of novel sulfonyl-containing N-acetyldopamine dimer enanitomers, (±)-aspongamide E (1), a new ester 2-aminoethyl ( E)-hex-2-enoate (2), along with 3 known compounds (3-5) were isolated from Aspongopus chinensis. Their structures were determined by spectroscopic methods. Compound 1 is a racemic mixture, chiral high-performance liquid chromatography separation followed by electronic circular dichroism calculations assigned the absolute configurations of 2 enantiomers of 1. Compounds 3-5 were isolated from A. chinensis for the first time. The biological activity of the selected new compounds against renal fibrosis was evaluated.

scholarly journals PHYTOCHEMICAL STUDY OF THE ARIAL PARTS OF Cleome rutidosperma DC PLANT

2010 ◽  
Vol 8 (3) ◽  
pp. 459-462 ◽  
Author(s):  
S. M. Mizanur Rahman ◽  
Serajum Munira ◽  
M. Amzad Hossain
Keyword(s):  
Spectral Analysis ◽  
Carboxylic Acid ◽  
Petroleum Ether ◽  
13C Nmr ◽  
Mass Spectral Data ◽  
Phytochemical Study ◽  
Mass Spectral ◽  
New Compounds ◽  
First Time ◽  
Cleome Rutidosperma

Two new compounds were identified as 2-ethyl-cyclohex-2-ene-6-hydroxy-methylene-1-carboxylic acid and 3b-hydroxy-lup-20(29)-en-28-oic acid, respectively, from the petroleum ether extracts of Cleome rutidosperma plant. These two constituents is the first time occurrence in this plant. The structures of the two different type of compounds are elucidated with the help of UV, IR, 1H-NMR, 13C-NMR, COSY, DEPT 90, DEPT 135 and mass spectral data.   Keywords: Cleome rutidosperm DC; isolation; spectral analysis

scholarly journals Improved Security Bounds for Generalized Feistel Networks

2020 ◽  
pp. 425-457
Author(s):  
Yaobin Shen ◽  
Chun Guo ◽  
Lei Wang
Keyword(s):  
Coupling Analysis ◽  
Random Functions ◽  
Feistel Networks ◽  
Type 3 ◽  
Tweakable Blockciphers ◽  
First Time

We revisit the security of various generalized Feistel networks. Concretely, for unbalanced, alternating, type-1, type-2, and type-3 Feistel networks built from random functions, we substantially improve the coupling analyzes of Hoang and Rogaway (CRYPTO 2010). For a tweakable blockcipher-based generalized Feistelnetwork proposed by Coron et al. (TCC 2010), we present a coupling analysis and for the first time show that with enough rounds, it achieves 2n-bit security, and this provides highly secure, double-length tweakable blockciphers.

scholarly journals Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 256 ◽  
Author(s):  
Xuchao Jia ◽  
Dan Yang ◽  
Yue Yang ◽  
Haihui Xie
Keyword(s):  
Spectroscopic Data ◽  
Structure Identification ◽  
Accurate Information ◽  
Phytochemical Study ◽  
Averrhoa Carambola ◽  
Nmr Data ◽  
Star Fruit ◽  
Flavor Precursors ◽  
New Compounds ◽  
First Time

The fruit of Averrhoa carambola L. (Oxalidaceae), commonly known as star fruit or carambola, is popular in tropical and subtropical regions. Carotenoid-derived components, mainly C13- and C15-norisoprenoids, contribute greatly to the flavor of star fruit. Previously reported norisoprenoids were tentatively identified by GC-MS analysis after enzymatic hydrolysis. To gain accurate information about glycosidically bound flavor precursors in star fruit, a phytochemical study was conducted, which led to the isolation of 16 carotenoid derivatives—One new C13-norisoprenoid glucoside, (5R,6S,7E,9R)-5,6,9-trihydroxy-7-megastigmene 9-O-β-d-glucoside (1); one new C15-norisoprenoid, (6S,7E,10S)-Δ9,15-10-hydroxyabscisic alcohol (11); and 14 known ones, of which 12 were in glucoside form. The structures of the two new compounds were elucidated on the basis of extensive spectroscopic data analysis and chemical reaction. Compound 11 was a rare C15-norisoprenoid with a double bond between C-9 and C-15, and its possible biogenetic pathway was proposed. The known compounds were identified by comparison of their mass and nuclear magnetic resonance (NMR) data with those reported in the literature. The structure identification of one new (1) and seven known (3–7, 9, and 10) C13-norisoprenoid glucosides from the genus Averrhoa for the first time enriches the knowledge of carotenoid-derived flavor precursors in star fruit.

scholarly journals Magnoflorine and Phenolic Derivatives from the Leaves of Croton xalapensis L. (Euphorbiaceae)

2009 ◽  
Vol 4 (12) ◽  
pp. 1934578X0900401 ◽  
Author(s):  
Carolina Arevalo ◽  
Cinzia Lotti ◽  
Anna Lisa Piccinelli ◽  
Mariateresa Russo ◽  
Ines Ruiz ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Cinnamyl Alcohol ◽  
Dihydroxybenzoic Acid ◽  
High Concentration ◽  
Phytochemical Study ◽  
Medicinal Properties ◽  
Phenolic Derivatives ◽  
First Time ◽  
Quantitative Hplc

The alkaloid magnoflorine 1, has been isolated for the first time from Croton xalapensis (Euphorbiaceae), in addition two phenylpropenols derivates, 3,4-dimethoxy-(E)-cinnamyl alcohol 2 and 3,4-dimethoxy-5-hydroxy-(E)-cinnamyl alcohol 3, 3,4,5-trimethoxycinnamic acid 4, gallic acid 5, methyl gallate 6 and 3,4-dihydroxybenzoic acid 7 have been also found; these compounds were identified by spectroscopic analysis particularly, 2D NMR and ESI-MS/MS techniques. The high concentration of magnoflorine, calculated with quantitative HPLC, of the aqueous extract, probably contributes to the remarkable medicinal properties of this plant. In addition this is the first phytochemical study on Croton xalapensis to be reported.

scholarly journals Phenolic Derivatives from Periplaneta americana

2017 ◽  
Vol 12 (11) ◽  
pp. 1934578X1701201
Author(s):  
Yong-Ming Yan ◽  
Hong-Jie Zhu ◽  
Bin Xiang ◽  
Jing-Jing Qi ◽  
Yong-Xian Cheng
Keyword(s):  
Nitric Oxide ◽  
Cell Proliferation ◽  
Wound Healing ◽  
Cell Migration ◽  
Periplaneta Americana ◽  
Inhibitory Effect ◽  
Spectroscopic Methods ◽  
Phenolic Derivatives ◽  
New Compounds

Periplaneta americana is a medicinal insect used for the treatment of the wound healing in China. In this study, four new compounds, named periplanols A-D (1-4), together with twelve known compounds, were isolated from the whole bodies of this species. Their structures were elucidated by extensive spectroscopic methods. All the isolates except compounds 6, 9, 11, and 14 were tested for their wound healing related activities towards nitric oxide (NO) inhibitory effect, cell proliferation in HDFs, cell migration and angiogenesis in HUVEC, respectively.

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