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 neo-Clerodane Diterpenoids from Scutellaria galericulata

2014 ◽  
Vol 9 (3) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Petko I. Bozov ◽  
Plamen N. Penchev ◽  
Josep Coll
Keyword(s):  
Acetone Extract ◽  
Aerial Parts ◽  
Nmr Data ◽  
Clerodane Diterpenoids ◽  
New Compounds ◽  
First Time

Four neo-clerodane diterpenoids, neoajugapyrin A, scutegalerins A and B and scutecolumnin C have been isolated from the acetone extract of the aerial parts of Scutellaria galericulata. Neoajugapyrin A and scutecolumnin C are reported in this species for the first time, whereas scutegalerins A and B are new compounds. NMR data of neoajugapyrin A are discussed in detail to support the proposed revised structure of ajugapyrin A.

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 Oleanane-type Triterpene Glycosides from Glycyrrhiza Uralensis

2007 ◽  
Vol 2 (3) ◽  
pp. 1934578X0700200 ◽  
Author(s):  
Jinwei Li-Yang ◽  
Jun-ichiro Nakajima ◽  
Nobuhito Kimura ◽  
Kazuki Saito ◽  
Shujiro Seo
Keyword(s):  
Natural Products ◽  
Spectroscopic Data ◽  
2D Nmr ◽  
Mass Spectrometric ◽  
Triterpene Glycosides ◽  
Glycyrrhiza Uralensis ◽  
Nmr Data ◽  
Nmr Methods ◽  
First Time ◽  
C Nmr

Chemical investigation of the roots of Glycyrrhiza uralensis resulted in the isolation of six oleanane-type triterpene glycosides (1 – 6), including one new saponin (1) and two (2 and 3) obtained as natural products for the first time. The new licorice saponin (1) was identified as 22β–acetoxylglycyrrhizin from [α]D, mass spectrometric, and UV, IR, and NMR spectroscopic data.. Full assignments of 1H and 13C-NMR data for compounds 2, 3, 4, 5 and 6 were made for the first time according to 2D NMR methods.

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 Saccharpiscinols A–C: Flavans with Potential Inflammatory Activities from One Actinobacteria Saccharomonospora piscinae

Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4909
Author(s):  
Yung-Shun Su ◽  
Jih-Jung Chen ◽  
Ming-Jen Cheng ◽  
Chee-Yin Chai ◽  
Aij-Lie Kwan ◽  
...  
Keyword(s):  
Data Analysis ◽  
Chromatographic Separation ◽  
Spectroscopic Data ◽  
2D Nmr ◽  
No Production ◽  
Raw 264.7 ◽  
Phytochemical Investigation ◽  
Inhibitory Activities ◽  
New Compounds ◽  
First Time

Phytochemical investigation and chromatographic separation of extracts from the actinobacteria strain Saccharomonospora piscinae that was isolated from dried fishpond sediment of Kouhu township, in the south of Taiwan, led to the isolation of three new compounds, saccharpiscinols A–C (1–3, respectively), and three new natural products, namely (2S)-5,7,3′,4′-tetrahydroxy-6,8-dimethylflavanone (4), methyl-4-hydroxy-2-methoxy-6-methylbenzoate (5), and (±)-7-acetyl-4,8-dihydroxy-6-methyl-1-tetralone (6). Compounds 4–6 were reported before as synthesized products, herein, they are reported from nature for the first time. The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic data analysis (1D- and 2D-NMR, MS, and UV) and comparison with literature data. The effect of some isolates on the inhibition of NO production in lipopolysaccharide-activated RAW 264.7 murine macrophages was evaluated. Saccharpiscinol A showed inhibitory activities against LPS-induced NO production.

scholarly journals Bioactive Capnosanes and Cembranes from the Soft Coral Klyxum flaccidum

Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 461
Author(s):  
Tseng ◽  
Ahmed ◽  
Huang ◽  
Tsai ◽  
Tai ◽  
...  
Keyword(s):  
Superoxide Anion ◽  
Spectroscopic Data ◽  
Cytochalasin B ◽  
Soft Coral ◽  
Biological Activities ◽  
Human Neutrophils ◽  
Data Comparison ◽  
Spectroscopic Analyses ◽  
New Compounds ◽  
First Time

Two new capnosane-based diterpenoids, flaccidenol A (1) and 7-epi-pavidolide D (2), two new cembranoids, flaccidodioxide (3) and flaccidodiol (4), and three known compounds 5 to 7 were characterized from the marine soft coral Klyxum flaccidum, collected off the coast of the island of Pratas. The structures of the new compounds were determined by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and spectroscopic data comparison with related structures. The rare capnosane diterpenoids were isolated herein from the genus Klyxum for the first time. The cytotoxicity of compounds 1 to 7 against the proliferation of a limited panel of cancer cell lines was assayed. The isolated diterpenoids also exhibited anti-inflammatory activity through suppression of superoxide anion generation and elastase release in the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-stimulated human neutrophils. Furthermore, 1 and 7 also exhibited cytotoxicity toward the tested cancer cells, and 7 could effectively inhibit elastase release. It is worth noting that the biological activities of 7 are reported for the first time in this paper.

scholarly journals New Thiodiketopiperazine and 3,4-Dihydroisocoumarin Derivatives from the Marine-Derived Fungus Aspergillus terreus

Marine Drugs ◽  
2020 ◽  
Vol 18 (3) ◽  
pp. 132 ◽  
Author(s):  
Jing-Shuai Wu ◽  
Xiao-Hui Shi ◽  
Guang-Shan Yao ◽  
Chang-Lun Shao ◽  
Xiu-Mei Fu ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
Aspergillus Terreus ◽  
Inhibitory Concentration ◽  
Tyrosine Phosphatase ◽  
Inhibitory Effect ◽  
Lipid Lowering ◽  
Ionization Mass ◽  
One Dimensional ◽  
New Compounds ◽  
First Time

Aspergillus terreus has been reported to produce many secondary metabolites that exhibit potential bioactivities, such as antibiotic, hypoglycemic, and lipid-lowering activities. In the present study, two new thiodiketopiperazines, emestrins L (1) and M (2), together with five known analogues (3–7), and five known dihydroisocoumarins (8–12), were obtained from the marine-derived fungus Aspergillus terreus RA2905. The structures of the new compounds were elucidated by analysis of the comprehensive spectroscopic data, including high-resolution electrospray ionization mass spectrometry (HRESIMS), one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR), and electronic circular dichroism (ECD) data. This is the first time that the spectroscopic data of compounds 3, 8, and 9 have been reported. Compound 3 displayed antibacterial activity against Pseudomonas aeruginosa (minimum inhibitory concentration (MIC) = 32 μg/mL) and antifungal activity against Candida albicans (MIC = 32 μg/mL). In addition, compound 3 exhibited an inhibitory effect on protein tyrosine phosphatase 1 B (PTP1B), an important hypoglycemic target, with an inhibitory concentration (IC)50 value of 12.25 μM.

scholarly journals Stereochemistry and NMR Data Assignment of Cyclopeptide Alkaloids from Zizyphus Oxyphylla

2010 ◽  
Vol 5 (8) ◽  
pp. 1934578X1000500
Author(s):  
Muhammad Nisar ◽  
Waqar Ahmad Kaleem ◽  
Achyut Adhikari ◽  
Zulfiqar Ali ◽  
Nusrat Hussain ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
Mass Spectrometric ◽  
Mass Spectrometric Data ◽  
Spectrometric Data ◽  
Nmr Data ◽  
Cyclopeptide Alkaloids ◽  
First Time ◽  
C Nmr

The structures of (3 S,7 R,13 S)-6-[2-(dimethylamino)-3-phenylpropanoyl]-19-methoxy-2-oxa-6,9,15-triazatetracyclo[16.3.1.03,7. 09,13]docosa-1-(22),16,18,20-tetraene-8,14-dione (1), nummularin-C (2) and nummularin-R (3) have been previously determined mainly based on mass spectrometric data. Stereochemistry and complete 1H and 13C NMR spectroscopic data assignments of these compounds are now described. Compounds 1 and 2 are reported for the first time from

scholarly journals New Eudesmane-Type Sesquiterpene Glycosides from the Leaves of Aster koraiensis

Plants ◽  
2020 ◽  
Vol 9 (12) ◽  
pp. 1811
Author(s):  
Ji-Young Kim ◽  
Young Hye Seo ◽  
Im-Ho Lee ◽  
He Yun Choi ◽  
Hak Cheol Kwon ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
2D Nmr ◽  
Isolation Procedure ◽  
Pge2 Production ◽  
Raw 264.7 Cells ◽  
Inhibitory Effects ◽  
Etoh Extract ◽  
Chemical Structures ◽  
New Compounds ◽  
First Time

Four new eudesmane-type sesquiterpenoids, (1R,5S,6R,7S,9S,10S)-1,6,9-trihydroxy-eudesm-3-ene-1,6-di-O-β-d-glucopyranoside (1), (1R,5S,6S,7R,9S,10S)-1,6,9,11-tetrahydroxy-eudesm-3-ene-1,6-di-O-β-d-glucopyranoside (3), (1R,5S,6R,7S,9S,10R)-9-O-(Z-p-coumaroyl)-1,6,9-trihydroxy-eudesm-3-ene-6-O-β-d-glucopyranoside (6), and (1R,5S,6R,7S,9S,10R)-9-O-(E-feruloyl)-1,6,9-trihydroxy-eudesm-3-ene-6-O-β-d-glucopyranoside (7), were isolated from a 95% EtOH extract of the leaves of Aster koraiensis by repeated chromatography. Moreover, three sesquiterpenoids (2, 4, and 5) and two caffeoylquinic acids (8 and 9) having previously known chemical structures were isolated during the isolation procedure. The four new compounds (1, 3, 6, and 7) were elucidated by spectroscopic data (1D- and 2D-NMR, MS, and ECD) interpretation and hydrolysis. Moreover, the absolute configurations of 2, 4, and 5 were determined for the first time in this study. The compounds isolated were tested for their viability on nitric oxide (NO) and prostaglandin E2 (PGE2) production on LPS-stimulated RAW 264.7 cells. Among them, only 7 presented weak inhibitory effects on both NO and PGE2 production.

scholarly journals Tangutidines A–C, Three Amphoteric Diterpene Alkaloids from Aconitum tanguticum

2021 ◽  
Author(s):  
Hao-Yi Li ◽  
Bing-Chao Yan ◽  
Li-Xin Wei ◽  
Han-Dong Sun ◽  
Pema-Tenzin Puno
Keyword(s):  
Spectroscopic Data ◽  
Cytotoxic Activities ◽  
Diterpene Alkaloids ◽  
Nmr Data ◽  
Whole Plant ◽  
Detailed Interpretation ◽  
First Time

AbstractThree new diterpene alkaloids, tangutidines A–C (1–3), and four known alkaloids (4–7) were isolated from the whole plant of Aconitum tanguticum, from which amphoteric diterpene alkaloids (1–3) were obtained for the first time. The structures of 1–3 were elucidated by detailed interpretation of spectroscopic data, including MS and NMR data. All of them were evaluated for their cytotoxic activities. Graphic Abstract

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