Norway Spruce Balm: Phytochemical Composition and Ability to Enhance Re-epithelialization In Vitro

AbstractThe balm of the Norway spruce (Picea abies) is a well-known traditional herbal medicine used to cure wounds. Even though clinical trials have confirmed its empirical use, the active constituents, their mode of action, and the exact composition of this natural product are still unknown. In this study, the balm was subjected to fractionated extraction and further purified employing flash chromatography, HPLC-PDA-ELSD, preparative and analytical TLC. Hydroxycinnamic acids ( 1– 3), the lignan pinoresinol ( 4), four hydroxylated derivatives of dehydroabietic acid (DHAA) ( 5 – 8), and dehydroabietic acid ( 9) were isolated. Their structures were elucidated by LC-MS, 1D- and 2D-NMR. Four extracts, two commercially available resin acids–pimaric acid ( 10) and isopimaric acid ( 11)–and the isolated compounds were tested for increased re-epithelialization of cell-free areas in a human adult low calcium high temperature keratinocytes monolayer. Lysophosphatidic acid (10 µM) served as positive control and ranged between 100% and 150% rise in cell-covered area related to the vehicle control. Two extracts containing carboxylic acids and non-acidic apolar constituents, respectively, boosted wound closure by 47% and 36% at 10 and 3 µg/mL, respectively. Pinoresinol, DHAA, three of its hydroxylated derivatives, and pimaric and isopimaric acid as well as defined combinations of the hydroxylated DHAA derivatives led to a significantly enhanced wound closure by up to 90% at concentrations between 1 and 10 µM. Overall, lignans and diterpene resin acids, main constituents of Norway spruce balm, are able to increase migration or proliferation of keratinocytes in vitro. The presented data link the phytochemistry of this natural wound healing agent with boosted re-epithelialization.

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Trypanocidal Activity of Oleoresin and Terpenoids Isolated from Pinus oocarpa

Zeitschrift für Naturforschung C ◽

10.1515/znc-2005-9-1009 ◽

2005 ◽

Vol 60 (9-10) ◽

pp. 711-716 ◽

Cited By ~ 16

Author(s):

Julieta Rubio ◽

José S. Calderón ◽

Angélica Flores ◽

Clementina Castro ◽

Carlos L. Céspedes

Keyword(s):

Methyl Ester ◽

Trypanosoma Cruzi ◽

Acute Infection ◽

Acid Methyl Ester ◽

Positive Control ◽

Dehydroabietic Acid ◽

Isopimaric Acid ◽

Acid Methyl ◽

Pinus Oocarpa

Abstract Fractionation with n-hexane/ethyl acetate (1:1 v/v) by open column chromatography of the oleoresin from Pinus oocarpa Schiede yielded two diterpenes, pimaric acid (1) and dehydroabietic acid (5), the sesquiterpene longifolene (3) and a diterpenic mixture containing pimaric acid (1), isopimaric acid (4) and dehydroabietic acid (5). Subsequently, the isolated compounds, the mixture of 1, 4 and 5, the oleoresin and the dehydroabietic acid methyl ester (2), were tested in vitro against epimastigotes of Trypanosoma cruzi, the causative agent of Chagas disease. The most active compounds were 1, 3 and the oleoresin, being as active as nifurtimox, a drug effective in the treatment of acute infection by American trypanosomiasis and used in this work as positive control.

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Homoadamantane and Adamantane Acylphloroglucinols from Hypericum hirsutum

Planta Medica ◽

10.1055/a-1617-7573 ◽

2021 ◽

Author(s):

Julianna Max ◽

Jörg Heilmann

Keyword(s):

Petroleum Ether Extract ◽

2D Nmr ◽

Positive Control ◽

Ionization Mass ◽

2D Nmr Spectroscopy ◽

Vitro Assay ◽

Ionization Mass Spectroscopy ◽

Ic50 Values ◽

Adamantane Skeleton

Abstract 1H NMR-guided fractionation of the petroleum ether extract of the aerial parts from Hypericum hirsutum yielded to the isolation of 19 polyprenylated polycyclic acylphloroglucinols. Structure elucidation based on 1D and 2D NMR spectroscopy together with high-resolution electrospray ionization mass spectroscopy revealed 14 acylphloroglucinols with a homoadamantane scaffold (1–14), while 5 further compounds showed an adamantane skeleton (15–19). Except for hookerione C (15), all isolated metabolites are hitherto unknown. While structurally-related metabolites have been isolated from other Hypericum species, it is the first report of admantan and homoadamantan type acylphloroglucinols in section Taeniocarpium Jaub. & Spach (Hypericaceae). The isolated compounds have been tested in a crystal violet-based in vitro assay on their properties to reduce the proliferation of human microvascular endothelial cells compared to hyperforin as the positive control. They showed a moderate reduction of proliferation with IC50 values in the range ~ 3 – 22 µM, with the homoadamantane-based compounds 2 and 4 being the most active. In addition, inhibition of the TNF-α-induced ICAM-1 expression was determined for 1 – 5, 7, and 10 – 12. Substances 3 and 12 reduced the ICAM-1 expression significantly (to 46.7% of control for 3, 62.3% for 12, at 50 µM).

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Comparative Study of Synthesis, Structural and Antioxidant Activity In Vitro of Some New Carboxylic α,α-diaminodiesters Derivatives

European Journal of Advanced Chemistry Research ◽

10.24018/ejchem.2021.2.3.64 ◽

2021 ◽

Vol 2 (3) ◽

pp. 6-13

Author(s):

Oumaima Karai ◽

Sara Hajib ◽

Serigne Abdou Khadir Fall ◽

Salaheddine Boukhssas ◽

Khadim Dioukhane ◽

...

Keyword(s):

Radical Scavenging ◽

Reducing Power ◽

2D Nmr ◽

Positive Control ◽

Alkylation Reaction ◽

X Ray Diffraction ◽

2D Nmr Spectroscopy ◽

Antioxidant Power ◽

Chemical Structures

Considering the richness of heterocyclic chemistry, and the diversity of applications it possesses, in the present work we were interested in preparing new polyfunctional α,α-diaminodiesters derived from glycine, via the N-alkylation reaction of methyl 2-azido-2-benzamidoacetate with a series of heterocyclic and non-heterocyclic carboxylic aminoesters, using different bases. The structures of the synthesized molecules were characterized by 1D and 2D NMR spectroscopy, mass spectrometry (MS-ESI) and elemental analysis. Two compounds from this series were isolated as single crystals and their chemical structures were determined by X-ray diffraction. The antioxidant effect of the synthesized compounds was tested in vitro using the free radical scavenging power (DPPH) and reducing power (FRAP) tests. The results show that the different extracts tested have a relatively high antioxidant power compared to the positive control considered, especially for the compound methyl 2-benzamido-2-(2-methoxy-2-oxo-1-phenylethyl)amino)acetate, which showed a very strong antiradical power and reducing power.

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Antibacterial Activity of Ethyl Acetate and Cream Formulation of Coleus atropurpureus leaves Against Staphylococcus aureus

Pharmaceutical Journal of Indonesia ◽

10.21776/ub.pji.2021.007.01.1 ◽

2021 ◽

Vol 7 (1) ◽

pp. 1-8

Author(s):

Indra Lasmana Tarigan ◽

◽

Afidatulx Muadifah ◽

Nindita Clourisa Clourisa Amaris Susanto ◽

Choirul Huda ◽

...

Keyword(s):

Staphylococcus Aureus ◽

Antibacterial Activity ◽

Ethyl Acetate ◽

Wound Closure ◽

Ph Value ◽

Positive Control ◽

Cream Formulation ◽

Closure Time ◽

Semi Solid

Infectious diseases caused by Staphylococcus aureus (Sa) bacteria reaching 70% of cases in Asia and can attack and survive in epithelial cells including endothelial cells. Attempts to overcome the infection caused by Sa by giving antibiotics, which work as antibacterial. Myana (Coleus atropurpureus L. Benth) leaves contain several active compounds that might act as antibacterial agents. This study aimed to analyze the antibacterial activity of Coleus Extract in vitro and to evaluate the formulation of the extract cream against the bacteria causing infection, Sa. Coleus leaves ethyl acetate extract contains alkaloids and tannins, the absorbance of Sa at the 3rd hour was getting smaller, from 0.668 to 0.552, this showed that the longer the incubation time of the extract against bacterial inoculation, the more bacteria died. Our cream formulation with criteria: the pH value, homogeneity, spreadability, adhesion, and protection power. Our cream formulation results were then evaluated based on the standard, with criteria: the pH value, homogeneity, spreadability, adhesion, and protection power. It seems that our cream is per the cream standards. It is semi-solid, brownish-white in color, smells typical of Coleus, and pH 6. Moreover, the cream is homogeneous with 5 cm of spreadability, 7 seconds for adhesion, and colorless. Moreover, we found that Coleus extract cream has better antibacterial activity than positive control with a wound closure time of 7-14 days for extract while more than 14 days for positive control.

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Metabolites of the honey mushroom, Armillariamellea

Canadian Journal of Chemistry ◽

10.1139/v87-002 ◽

1987 ◽

Vol 65 (1) ◽

pp. 7-14 ◽

Cited By ~ 24

Author(s):

William A. Ayer ◽

John B. Macaulay

Keyword(s):

Liquid Culture ◽

Fruit Production ◽

Dehydroabietic Acid ◽

Resin Acids ◽

Fungal Metabolites ◽

Isopimaric Acid ◽

Levopimaric Acid ◽

Sandaracopimaric Acid

The fungus Armillariamellea (Vahl ex. Fr.) Kummer is responsible for severe losses in timber and fruit production. The metabolites isolated when certain strains of this fungus are grown in liquid culture have been identified as diterpenoid acids possessing the abietane (1) and pimarane (2) skeletons. These compounds, known collectively as resin acids, have not been reported previously from a fungal source. In addition to the resin acids dehydroabietic acid (3), pimaric acid (4), isopimaric acid (5), and sandaracopimaric acid (6), three additional acids, levopimaric acid endo-peroxide (7), 7-oxodehydroabietic acid (9), and 7-oxo-15-hydroxydehydroabietic acid (10) were obtained. On one occasion three orange pigments, austocystin F (11), averufin (12), and averufanin (13), all previously known fungal metabolites, were isolated.

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Chemical Constituents of the Deep-Sea-Derived Penicillium solitum

Marine Drugs ◽

10.3390/md19100580 ◽

2021 ◽

Vol 19 (10) ◽

pp. 580

Author(s):

Zhi-Hui He ◽

Jia Wu ◽

Lin Xu ◽

Man-Yi Hu ◽

Ming-Ming Xie ◽

...

Keyword(s):

Deep Sea ◽

Chemical Constituents ◽

A549 Cells ◽

Acid Methyl Ester ◽

2D Nmr ◽

Positive Control ◽

Ic50 Values ◽

Penicillium Solitum ◽

New Compounds

A systematic chemical investigation of the deep-sea-derived fungus Penicillium solitum MCCC 3A00215 resulted in the isolation of one novel polyketide (1), two new alkaloids (2 and 3), and 22 known (4–25) compounds. The structures of the new compounds were established mainly on the basis of exhaustive analysis of 1D and 2D NMR data. Viridicatol (13) displayed moderate anti-tumor activities against PANC-1, Hela, and A549 cells with IC50 values of around 20 μM. Moreover, 13 displayed potent in vitro anti-food allergic activity with an IC50 value of 13 μM, compared to that of 92 μM for the positive control, loratadine, while indole-3-acetic acid methyl ester (9) and penicopeptide A (10) showed moderate effects (IC50 = 50 and 58 μM, respectively).

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ISOLATION AND CHEMICAL CHARACTERIZATION OF BIOACTIVE ALKALOID FROM ARGYREIA SPECIOSA LINN. HAVING ACTION ON ISOLATED RAT LEYDIG CELLS

Asian Journal of Pharmaceutical and Clinical Research ◽

10.22159/ajpcr.2019.v12i10.34789 ◽

2019 ◽

pp. 276-280

Author(s):

NIRAJ VYAS ◽

KANAN GAMIT ◽

MANAN RAVAL ◽

SAMIR PATEL

Keyword(s):

1H Nmr ◽

Leydig Cells ◽

Chemical Characterization ◽

Positive Control ◽

Flash Chromatography ◽

Spectral Studies ◽

Testosterone Synthesis ◽

Isolated Rat

Objective: Present study was aimed to isolate and chemically characterize bioactive constituent from alkaloid enriched fraction, prepared from roots of Argyreia speciosa Linn. Materials and methods: Literature review revealed presence of ergoline type of alkaloids in roots. Alkaloidal fraction was prepared and screened for its action on testosterone biosynthesis, in- vitro, using isolated rat leydig cells. Dehydroepiandosterone was used as positive control. This bioactive fraction was subjected to open column chromatography followed by flash chromatography, to isolate constituent. One compound (A1) was isolated from the fraction and its purity was ascertained using TLC and HPLC studies. A1 was chemically characterized by IR, Mass and 1H-NMR studies, to elucidate probable chemical structure. A1 was screened for action on testosterone synthesis too, using isolated rat Leydig cells model. The fraction was standardized with respect to amount of A1 present. Results: Alkaloidal fraction (1000 µg/ml) incubated Leydig cells showed nearly, 22 fold increase in testosterone content as compared to untreated cells. The studies also yielded increase in testosterone content, in cells treated with test fractions and as observed in case of positive control. TLC studies indicated that A1 might possess ergoline moiety in the structure. IR, Mass and 1H NMR spectral studies suggested that A1 might be N-methyl ergometrine. This was the first report included isolation and chemical characterization of N-methyl ergometrine from Argyreia speciosa. A1 (1000 µg/ml) was found to stimulate testosterone content, by 14.62 fold, in culture media of Leydig cells after incubation. Conclusion: The results of in vitro studies, confirmed that the standardized alkaloid fraction as well as A1 had ability to stimulate Leydig cells to secrete testosterone. A1 might be N-methyl ergometrine and being ergometrine derivative it might act through oxytocine receptors expressed on the Leydig cells and stimulates testosterone synthesis.

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THE SIBERIAN LARCH GROUP COMPOSITION AND ACID NEEDLES AT DIFFERENT VEGETATION PERIODS

chemistry of plant raw material ◽

10.14258/jcprm.2019045477 ◽

2019 ◽

pp. 207-214

Author(s):

Dar'ya Sergeyevna Mikson ◽

Viktor Ivanovich Roshchin

Keyword(s):

Fatty Acids ◽

Group Composition ◽

Siberian Larch ◽

Dehydroabietic Acid ◽

Resin Acids ◽

Hydroxy Acids ◽

Isopimaric Acid ◽

Isopropanol Extract ◽

Extractive Substances ◽

Higher Fatty Acids

The research results of the Siberian larch needle extractives are presented in paper. The content of extractive substances from green and yellow needles extracted by organic solvents with different polarities is determined. It is found out that the double increase of the yellow needle extractive substances content soluble in hydrocarbon extractant is observed, whereas it is decreased by 30 per cent when extracted with propan-2-ol. The group composition of needle extracts derived from isopropanol extract by petroleum ether is determined. The neutral substances content in both needle collections is practically the same, although the yellow needles contain less acid “bound” in the form of esters. There is a high content of waxes in the needles, which mainly consist of secondary nonacosanol-10 alcohol. The composition of free and “bound” acids in Siberian larch needles of different vegetation periods is established. The needles are dominated by groups of higher unsaturated C-18 fatty acids. Resin acids are represented by isopimaric acid (isopimaric and sandaracopimaric) and abietic acids: abietic, dehydroabietic and levopiric acids. In yellow needles, the content of dehydroabietic acid is increased quadrupled and the hydroxy acids are identified: 15-hydroxyabietic acid and 15-hydroxyhydroabietic acid. The tri- and tetraenic C-20 acids are identified among higher fatty acids.

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