Growth Inhibition and Apoptotic Effect of Pine Extract and Abietic Acid on MCF-7 Breast Cancer Cells via Alteration of Multiple Gene Expressions Using In Vitro Approach

In vitro anti-proliferative activity of Pinus palustris extract and its purified abietic acid was assessed against different human cancer cell lines (HepG-2, MCF-7 and HCT-116) compared to normal WI-38 cell line. Abietic acid showed more promising IC50 values against MCF-7 cells than pine extract (0.06 µg/mL and 0.11 µM, respectively), with insignificant cytotoxicity toward normal fibroblast WI-38 cells. Abietic acid triggered both G2/M cell arrest and subG0-G1 subpopulation in MCF-7, compared to SubG0-G1 subpopulation arrest only for the extract. It also induced overexpression of key apoptotic genes (Fas, FasL, Casp3, Casp8, Cyt-C and Bax) and downregulation of both proliferation (VEGF, IGFR1, TGF-β) and oncogenic (C-myc and NF-κB) genes. Additionally, abietic acid induced overexpression of cytochrome-C protein. Furthermore, it increased levels of total antioxidants to diminish carcinogenesis and chemotherapy resistance. P. palustris is a valuable source of active abietic acid, an antiproliferative agent to MCF-7 cells through induction of apoptosis with promising future anticancer agency in breast cancer therapy.

Characteristics and Kinetics Study of Glycerolabietate from Glycerol and Abietic Acid from Rosin

Rosin is a natural resin from the coniferous tree sap, which separated from its oil content (terpenes). Rosin is brittle. Therefore modifications are needed to improve its mechanical properties. The main content of rosin is abietic acid which has a carboxylic group, so it can form an ester group when reacted with polyhydric alcohol (polyalcohol) such as glycerol. The research aimed to study the kinetics of the esterification reaction between the hydroxyl group in glycerol and the carboxylic group in abietic acid from rosin at various reaction temperatures and reactant compositions. This reaction is carried out in a three-neck flask at atmospheric pressure without a catalyst. The reaction temperatures used were 180˚C, 200˚C, and 220˚C, and the ratio of rosin and glycerol was 1:1, 1:3, and 1:5. The reaction kinetics calculations were analyzed with acid number data over the reaction time using three different models. The calculations showed that this reaction involves positioning a hydroxyl group on glycerol, which the primary and secondary hydroxyl groups contribute to forming a rosin ester (glycerolabietate). The rate of reaction constants of primary hydroxyl of glycerol and abietic acid were in the range 6.25x10-4 - 3.90x10-3 g/(mgeq.min), while reaction rate constants of secondary hydroxyl and abietic acid were in the range 1.06x10-5 - 1.15x10-4 g/(mgeq.min). FTIR analysis showed a change in the hydroxyl, carboxylate, and ester groups which were assigned by a shift of wavenumber and a difference of intensity at 3200-3570 cm-1, 1697.36 cm-1, and 1273.02 cm-1.

Chiral Quaternary Ammonium Salt Derived from Dehydroabietylamine: Synthesis and Application to Alkynylation of Isatin Derivatives Catalyzed by Silver

Abietic acid and its derivatives have broadly been used in fine chemicals and are renewable resources. Its inherent chiral rigid tricyclic phenanthrene skeleton is unique. Its utilities in asymmetric catalysis remain to be explored. A series new amide-type chiral quaternary ammoniums bearing dehydroabietylamine were designed, and prepared by two convenient steps. Acylation of dehydroabietylamine with bromoacetyl chloride afforded amide holding bromoacetyl group in higher yields using triethyl amine as base. Subsequent quaternization reaction gave the desired amide-type chiral quaternary ammoniums. The new chiral quaternary ammoniums can be used as phase-transfer catalyst (PTC) for the transition metal-catalysed alkynylation of isatin derivatives.

A multi-analytical approach for the identification of the natural resin from the Ming tomb in Shaanxi, China

Several well-preserved polychrome lacquered coffins were found in Zhang Dong family’s tombs in Shaanxi, China, rare in the history of archaeological excavation. In the lacquered coffins, a large amount of dark solid of suspected natural resin was unearthed with mysterious compositions and uses, exerting a tremendous fascination on archaeologists. In this work, a new method was explored for the identification of the suspected natural resin, mainly based on thermogravimetry (TG), elemental analysis (EA), scanning electron microscopy-energy dispersive spectrometry (SEM-EDS), matrix-assisted laser desorption ionisation time-of-flight mass spectrometry (MALDI-TOF-MS) and Fourier transform infrared spectrometry (FT-IR). The results suggested that the sample was mainly composed of organics with a content of 81.66% and little inorganics with a content of 2.21% by water excluded. Rosin with the main component of abietic acid (molecular formula C20H30O2) was identified as the principal component of the sample. Dehydrogenated abietic acid (DHA) and other oxides were also tested out. FT-IR confirmed the identification results. SEM revealed the rough surfaces evenly covered with holes of similar sizes. The use of this method directly obtained integral quasi-molecular ion fragments and molecular components of the sample. As a result, intricate multi-stage mass spectrometry is avoidable, which dramatically simplifies the analysis procedure. This approach is simple and effective for the identification of precious relic samples, requires no references, and has potential for the analysis of these kinds of unknown samples. Especially, for the first time, EA is used to identify natural resins from archaeological sites.

Rheological Characterization of Emulsified Bitumen from Industrial Waste

Emulsified bitumen is an aqueous mixture of bitumen and can be used in insulation and coating applications. In this study, used automotive oil was utilized as a component in bitumen emulsion formulation. Five formulations of bitumen emulsion comprising different ratios of neat bitumen and recycled automotive oil were formulated, namely EMB01–EMB05. The formulation utilized 1 g of abietic acid (C20H30O2) as an emulsifier. The formulated bitumen was characterized for penetration, softening point, differential scanning calorimetry, viscosity, and oscillatory test, and the results were compared to commercial bitumen emulsion (ATLAS bitumen emulsion). The results show that EMB05 has softer consistency, high viscosity, temperature susceptibility, higher thermal stability, and an adaptable viscoelastic range compared to other formulations that provide suitable properties for coating and insulation of wall waterproof material.

Synergistic Effect of Abietic Acid with Oxacillin against Methicillin-Resistant Staphylococcus pseudintermedius

Resin acids are valued in traditional medicine for their antiseptic properties. Among these, abietic acid has been reported to be active against methicillin-resistant Staphylococcus aureus (MRSA) strains. In veterinary healthcare, the methicillin-resistant Staphylococcus pseudintermedius (MRSP) strain is an important reservoir of antibiotic resistance genes including mecA. The incidence of MRSP has been increasing, and treatment options in veterinary medicine are partial. Here, we investigated the antimicrobial and antibiofilm properties of abietic acid against three MRSP and two methicillin-susceptible Staphylococcus pseudintermedius (MSSP) strains, isolated from diseased pet animals and human wound samples. Abietic acid showed a significant minimal inhibitory concentration (MIC) value ranging from 32 to 64 μg/mL (MRSPs) and 8 μg/mL (MSSP). By checkerboard method we demonstrated that abietic acid increased oxacillin susceptibility of MRSP strains, thus showing a synergistic interaction with oxacillin. Abietic acid was also able to contrast the vitality of treated MSSP and MRSP1 biofilms at 20 μg/mL and 40 μg/mL, respectively. Finally, the compound moderately reduced mecA, mecR1 and mec1 gene expression. In conclusion, the results here reported demonstrate the antimicrobial activity of abietic acid against MRSP and support the use of this compound as a potential therapeutic agent to be used in combinatorial antibiotic therapy.

Thermally Conductive Film Fabricated Using Perforated Graphite Sheet and UV-Curable Pressure-Sensitive Adhesive

Thermally conductive films play a crucial role in expanding the lifetime of electronics by dissipating concentrated heat to heatsinks. In this work, a thermally conductive film (g-TC film) was manufactured using a perforated graphite sheet (p-GS) and a UV-curable pressure-sensitive adhesive (PSA) by lamination. A novel UV-curable PSA was prepared by incorporating a UV-curable abietic acid ester into a PSA composition. The UV-curable PSA became a tack-free film upon UV irradiation; thus, a flexible g-TC film with a 52-μm thickness was obtained. The defects in the g-TC film caused by air bubbles were removed by treating the p-GS with oxygen plasma. As the UV-cured PSA made a joint through the holes in the p-GS, cleavage of the graphite was not observed after 10,000 U-folding test cycles with a folding radius of 1 mm. The calculated in-plane thermal conductivity of the fabricated g-TC film was 179 W∙m−1K−1, which was stable after the U-folding tests.