scholarly journals (E)-2,6,10-Trimethyldodec-8-en-2-ol: An Undescribed Sesquiterpenoid from Copaiba Oil

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4456
Author(s):  
Mohammed F. Hawwal ◽  
Zulfiqar Ali ◽  
Mei Wang ◽  
Jianping Zhao ◽  
Joseph Lee ◽  
...  
Keyword(s):  
Chemical Constituents ◽  
2D Nmr ◽  
The United States ◽  
Mass Spectral Data ◽  
Herbal Supplements ◽  
Ongoing Research ◽  
Mass Spectral ◽  
Copaiba Oil ◽  
Positive Effect

The use of copaiba oil has been reported since the 16th century in Amazon traditional medicine, especially as an anti-inflammatory ingredient and for wound healing. The use of copaiba oil continues today, and it is sold in various parts of the world, including the United States. Copaiba oil contains mainly sesquiterpenes, bioactive compounds that are popular for their positive effect on human health. As part of our ongoing research endeavors to identify the chemical constituents of broadly consumed herbal supplements or their adulterants, copaiba oil was investigated. In this regard, copaiba oil was subjected to repeated silica gel column chromatography to purify the compounds. As a result, one new and seven known sesquiterpenes/sesquiterpenoids were isolated and identified from the copaiba oil. The new compound was elucidated as (E)-2,6,10-trimethyldodec-8-en-2-ol. Structure elucidation was achieved by 1D- and 2D NMR and GC/Q-ToF mass spectral data analyses. The isolated chemical constituents in this study could be used as chemical markers to evaluate the safety or quality of copaiba oil.

scholarly journals Chemical Constituents of Phoebe poilanei and Their Cytotoxic Activity

2019 ◽  
Vol 14 (5) ◽  
pp. 1934578X1985096
Author(s):  
Nguyen Thi Viet Thanh ◽  
Tran Thi Minh ◽  
Dinh Thi Thu Hien ◽  
Ho Duc Cuong ◽  
Yohan Seo ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
High Resolution ◽  
Cytotoxic Activity ◽  
Spectral Data ◽  
Chemical Constituents ◽  
Flavonol Glycosides ◽  
Ionization Mass ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Chemical Structures

Two new flavonol glycosides, rhamnocitrin 3- O-α-L-rhamnopyranosyl-(1→6)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (1) and quercetin 3- O-6- Z- p-coumaroyl-β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranoside (2), along with 3 flavonol glycosides, isoquercitrin (3), rutin (4), and quercetin 3- O-α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranoside (5), and two known sesquiterpenes, alismol (6) and spathulenol (7), were isolated from the leaves of Phoebe poilanei Kosterm. Their chemical structures were elucidated by analyses of their high-resolution electrospray ionization mass spectral data and nuclear magnetic resonance spectral data and comparison with those reported in the literature. Two sesquiterpenes 6 and 7 were found to exhibit moderate cytotoxic activity with IC50 values ranging from 21.6 to 29.8 µM.

scholarly journals Three New Aaptamines from the Marine Sponge Aaptos sp. and Their Proapoptotic Properties

2010 ◽  
Vol 5 (12) ◽  
pp. 1934578X1000501 ◽  
Author(s):  
Larisa K. Shubina ◽  
Tatyana N. Makarieva ◽  
Sergey A. Dyshlovoy ◽  
Sergey N. Fedorov ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Detailed Analysis ◽  
Spectral Data ◽  
Marine Sponge ◽  
2D Nmr ◽  
Human Leukemia ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Induced Apoptosis

Three new aaptamine-type alkaloids, 2,3-dihydro-2,3-dioxoaaptamine (1), 6 -( N-morpholinyl)-4,5-dihydro-5-oxo-demethyl(oxy)aaptamine (2) and 3-(methylamino)demethyl(oxy)aaptamine (3), along with known aaptamines were isolated from the sponge Aaptos sp. Their structures were determined on the basis of detailed analysis of their 1D and 2D NMR spectroscopic and mass spectral data. The isolated compounds induced apoptosis in human leukemia THP-1 cells.

scholarly journals Aureobasidin, New Antifouling Metabolite from Marine-Derived Fungus Aureobasidium sp

2009 ◽  
Vol 4 (3) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Ahmed Abdel-Lateff ◽  
Ehab S. Elkhayat ◽  
Mostafa A. Fouad ◽  
Tatsufumi Okino
Keyword(s):  
Escherichia Coli ◽  
Bacillus Subtilis ◽  
Candida Albicans ◽  
Spectral Data ◽  
2D Nmr ◽  
Enoic Acid ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Fungistatic Activity ◽  
Aureobasidium Sp

Two antifouling compounds, aureobasidin (1), a new ester with an unusual 4,6-dihydroxydecanoic acid residue, and (3 R,5 S)-3,5-dihydroxydecanoic acid (2), were isolated from the marine-derived fungus Aureobasidium sp., in addition to (5 R,3 Z)-5-hydroxydec-3-enoic acid (3) and ( R)-3-hydroxydecanoic acid (4). The structures were unambiguously established by IR, 1D and 2D NMR spectroscopic and mass spectral data. Compounds 1-3 were found to be active against Bacillus subtilis, Escherichia coli and Staphyllococcus aureus. Compound 3 showed fungistatic activity against Candida albicans.

Tithoniaquinone A and Tithoniamide B: A New Anthraquinone and a New Ceramide from Leaves of Tithonia diversifolia

2006 ◽  
Vol 61 (1) ◽  
pp. 78-82 ◽  
Author(s):  
Meffo Yemele Bouberte ◽  
Karsten Krohn ◽  
Hidayat Hussain ◽  
Etienne Dongo ◽  
Barbara Schulz ◽  
...  
Keyword(s):  
2D Nmr ◽  
Antibacterial Activities ◽  
Tithonia Diversifolia ◽  
Mass Spectral Data ◽  
Substitution Pattern ◽  
Microbotryum Violaceum ◽  
Mass Spectral ◽  
Antibacterial And Antifungal ◽  
First Time ◽  
Unusual Substitution

From the leaves of Tithonia diversifolia, four compounds were isolated and identified. Two of them, the anthraquinone tithoniquinone A (1) with an unusual substitution pattern on the anthraquinone skeleton, and the ceramide, named tithoniamide B (2a), are reported for the first time as natural products. Their structures were determined by comprehensive analyses of their 1D and 2D NMR and electron impact (EI) mass spectral data. The remaining two known compounds were identified as psoralen and l-quebrachitol. Preliminary studies showed that tithoniaquinone A (1) is strongly antibacterial and antifungal against Gram-positive Bacillus megaterium and Microbotryum violaceum, respectively, while psoralen has strong algicidal, fungicidal, and antibacterial activities.

scholarly journals Phenylisoxazole-3/5-Carbaldehyde Isonicotinylhydrazone Derivatives: Synthesis, Characterization, and Antitubercular Activity

2021 ◽  
Vol 2021 ◽  
pp. 1-14
Author(s):  
Fernando Carrasco ◽  
Wilfredo Hernández ◽  
Oscar Chupayo ◽  
Patricia Sheen ◽  
Mirko Zimic ◽  
...  
Keyword(s):  
Antitubercular Activity ◽  
2D Nmr ◽  
Basis Set ◽  
Isomeric Form ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Computational Calculations ◽  
Ft Ir ◽  
Antituberculous Activity

Eight new phenylisoxazole isoniazid derivatives, 3-(2′-fluorophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (1), 3-(2′-methoxyphenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (2), 3-(2′-chlorophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (3), 3-(3′-clorophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (4), 3-(4′-bromophenyl)isoxazole-5-carbaldehyde isonicotinylhydrazone (5), 5-(4′-methoxiphenyl)isoxazole-3-carbaldehyde isonicotinylhydrazone (6), 5-(4′-methylphenyl)isoxazole-3-carbaldehyde isonicotinylhydrazone (7), and 5-(4′-clorophenyl)isoxazole-3-carbaldehyde isonicotinylhydrazone (8), have been synthesized and characterized by FT-IR, 1H-NMR, 13C-NMR, and mass spectral data. The 2D NMR (1H-1H NOESY) analysis of 1 and 2 confirmed that these compounds in acetone-d6 are in the trans(E) isomeric form. This evidence is supported by computational calculations which were performed for compounds 1–8, using DFT/B3LYP level with the 6-311++G(d,p) basis set. The in vitro antituberculous activity of all the synthesized compounds was determined against the Mycobacterium tuberculosis standard strains: sensitive H37Rv (ATCC-27294) and resistant TB DM97. All the compounds exhibited moderate bioactivity (MIC = 0.34–0.41 μM) with respect to the isoniazid drug (MIC = 0.91 μM) against the H37Rv sensitive strain. Compounds 6 (X = 4′-OCH3) and 7 (X = 4′-CH3) with MIC values of 12.41 and 13.06 μM, respectively, were about two times more cytotoxic, compared with isoniazid, against the resistant strain TB DM97.

Chemical Constituents of Adesmia Boronioides and Evaluation of their Antioxidant Activity

2015 ◽  
Vol 8 (3) ◽  
pp. 2919-2223
Author(s):  
Orlando Muñoz ◽  
C Delporte
Keyword(s):  
Chemical Constituents ◽  
Antioxidant Properties ◽  
2D Nmr ◽  
Isolation And Identification ◽  
Ongoing Research ◽  
Phytochemical Investigation ◽  
Kaempferol Glycoside ◽  
Pharmacologically Active ◽  
Pharmacologically Active Compounds ◽  
First Time

As part of our ongoing research into the pharmacologically active compounds of Chilean flora, here we did phytochemical investigation of Adesmia boronioides Hook.f (fabaceae). (Papilonaceae) leaves. This effort has led to isolation and identification of liqueritigenin, isoliquiritigenin, sesamin, isodrimenin and a kaempferol glycoside, kaempferol 3-O-β-D-[galactopyranosyl  (1–2) rhamnoside]-7-O –α-L-rhamnopyranoside.Compound structures were identified by 1D- and 2D-NMR experiments, mass and UV spectrometry and comparison with data from the literature. This is the first time these compounds have been isolated from this plant’s leaves.These active constituents have been studied further pharmacologically. Antioxidant properties in A. boronioides leaves were determined.

scholarly journals Lathyrane Diterpenes from the Latex of Euphorbia laurifolia

2017 ◽  
Vol 12 (5) ◽  
pp. 1934578X1701200
Author(s):  
María Jesús Durán-Peña ◽  
María Eugenia Flores-Giubi ◽  
José Manuel Botubol-Ares ◽  
Felipe Escobar-Montaño ◽  
Antonio J. Macías-Sánchez ◽  
...  
Keyword(s):  
Detailed Analysis ◽  
Spectral Data ◽  
2D Nmr ◽  
Mass Spectral Data ◽  
Mass Spectral

Two new macrocyclic diterpenes, 2- epi-latazienone (4) and 15β-acetoxy-7β-nicotinoyloxy-3β8α-di-(2-methylpropanoyloxy)–4αH,9αH,11αH-lathyra-5 E,12 E-dien-14-one (5), and three known lathyrane-type diterpenes (1-3) were isolated from Euphorbia laurifolia latex. Their structures were determined on the basis of a detailed analysis of their 1D and 2D NMR spectroscopic and mass spectral data.

scholarly journals Furostanol Saponin and Diphenylpentendiol from the Roots of Asparagus racemosus

2012 ◽  
Vol 7 (8) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Upendra Sharma ◽  
Neeraj Kumar ◽  
Bikram Singh
Keyword(s):  
Detailed Analysis ◽  
Spectral Data ◽  
Ursolic Acid ◽  
2D Nmr ◽  
Asparagus Racemosus ◽  
Steroidal Saponin ◽  
Mass Spectral Data ◽  
First Report ◽  
Mass Spectral

A new furostanol steroidal saponin, shatavaroside C (1), and a new diphenylpentendiol, shatavarol (2), together with five known compounds, shatavarin IV (3), racemoside A (4), β-sitosterol (5) stigmasterol (6) and ursolic acid (7), have been isolated from the roots of Asparagus racemosus. This is the first report on the isolation of racemoside A (4) from roots of the plant. Structures of isolated compounds were determined on the basis of detailed analysis of their 1D, 2D NMR and mass spectral data.

scholarly journals Degradation Products of Rubusoside under Acidic Conditions

2015 ◽  
Vol 10 (4) ◽  
pp. 1934578X1501000
Author(s):  
Indra Prakash ◽  
Cynthia Bunders ◽  
Krishna P. Devkota ◽  
Romila D. Charan ◽  
Rachael M. Hartz ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Spectral Data ◽  
Degradation Products ◽  
2D Nmr ◽  
Structural Elucidation ◽  
Mass Spectral Data ◽  
2D Nmr Spectroscopy ◽  
Mass Spectral ◽  
Temperature Conditions ◽  
Acidic Conditions

A natural sweetener, Rubusoside (1), subjected to extreme pH and temperature conditions, resulted in the isolation and structural elucidation of one novel rubusoside degradant (7), together with seven known degradants (2-6 and 8-9). 1D and 2D NMR spectroscopy (1H, 13C, COSY, HSQC-DEPT, HMBC, and NOESY) and mass spectral data were used to fully characterize the degradant 7.

scholarly journals TERPENOIDS FROM THE LEAVES AND STEMS OF DYSOXYLUM TPONGENSE

2019 ◽  
Vol 57 (2) ◽  
pp. 139
Author(s):  
Pham Ngoc Khanh ◽  
Bui Huu Tai ◽  
Tran Thu Huong ◽  
To Dao Cuong ◽  
Young Ho Kim ◽  
...  
Keyword(s):  
Spectral Data ◽  
Chemical Constituents ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Chemical Structures

Study on chemical constituents from the leaves and stems of Dysoxylum tpongense Pierre resulted in the isolation of six known compounds (1–6). The chemical structures of isolated compounds were identified as cabraleahydroxylactone (1), cabraleahydroxylactone-3-acetate (2), (+) spathulenol (3), b-sitosterol (4), stigmasterol (5), and stigmast-4-en-3-one (6) by comparison of the physicochemical, interpretation of NMR and mass spectral data with that reported in the literature.

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