New Hypocholesterolemic Abietamide Derivatives. II. Synthesis and Hypocholesterolemic Activity of N-Phenyl-.DELTA.8-dihydroabietamides.

Fujita, Yukio; Yoshikuni, Yoshiaki; Sotomatsu, Tomoko; Mori, Tamiki; Ozaki, Takayuki; Sempuku, Kenji; Ogino, Akio; Kise, Masahiro; Enomoto, Hiroshi

doi:10.1248/cpb.39.1193

Cited by 10 publications

(3 citation statements)

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“…Reports have appeared on effects of abietic (15) and dehydroabietic (27) acids on serum cholesterol levels (84) that have induced the search for hypocholesterolemic derivatives more potent than natural ones (85). Thus, the primary amides of tetrahydroabietic and A8-dihydroabietic (1) acids do not display hypocholesterolemic activity and the N-alkyl secondaries lead to increases in serum cholesterol levels, whereas the presence of benzene rings in the substituent increases the hypocholesterolemic activity to a considerable extent (86). Additionally, the antiarrhythmic effect of N-12-(diethylamino)ethyl]dehydroabietamide is higher than that of procainamide, although it is less effective than guanidine.…”

Section: Cardiovascular Activitiesmentioning

confidence: 99%

Abietane Acids: Sources, Biological Activities, and Therapeutic Uses

Feliciano¹,

Gordaliza²,

Salinero³

et al. 1993

Planta Med

115

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Biological Activities and Uses The use of pine resin as a whole or its derivatives, essence, and colophony as expectorants, modifiers of bronchial secretions, and antiseptics for the urinary tract, as weli as rubefacients and vessicants in poultices and creams in veterinary practice is described in several Pharmacognosy and Medicinal Plant treatises (66, 67). In recent years (i967-i992), studies on the biological activities of abietane acids have been performed with pure compounds and activities like antimicrobial, antiulcer, cardiovascular, allergenic, antiallergic, and many uses in cosmetics and dermatologic preparations have been reported for some of them. Antimicrobial Activity The antimicrobial activity of pisiferic acid (48) and its derivatives has been established against Pseudomonas, Proteus, and Klebsiella (68) as have its antibacterial actions against Gram-positive microorganisms, its antifungal activity, and its activity in experimental carcinoma of the uterus (HeLa-S3 cells) (55, 58). In the systems assayed, pisiferic acid (48) was active against Proteus vulgaris, Staphylococcus aureus, Bacillus subtilis, Pyricularia oryzae, and HeLa-S3 celis, while methylation of the

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Section: Cardiovascular Activitiesmentioning

confidence: 99%

Abietane Acids: Sources, Biological Activities, and Therapeutic Uses

Feliciano¹,

Gordaliza²,

Salinero³

et al. 1993

Planta Med

115

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“…Rosin is produced by removing turpentine from oleoresin of Pinus species and it is a commonly used medicine in TCM [ 6 ]. Besides its applications in chemical industries, the biological activities have been revealed in recent decades [ 7 , 8 ]. DHA is one of the main resin acids and it is a promising template for synthetic modifications.…”

Section: Introductionmentioning

confidence: 99%

Dehydroabietic Acid Derivative QC4 Induces Gastric Cancer Cell Death via Oncosis and Apoptosis

Luo

et al. 2016

BioMed Research International

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Aim. QC4 is the derivative of rosin's main components dehydroabietic acid (DHA). We investigated the cytotoxic effect of QC4 on gastric cancer cells and revealed the mechanisms beneath the induction of cell death. Methods. The cytotoxic effect of QC4 on gastric cancer cells was evaluated by CCK-8 assay and flow cytometry. The underlying mechanisms were tested by administration of cell death related inhibitors and detection of apoptotic and oncosis related proteins. Cytomembrane integrity and organelles damage were confirmed by lactate dehydrogenase (LDH) leakage assay, mitochondrial function test, and cytosolic free Ca2+ concentration detection. Results. QC4 inhibited cell proliferation dose- and time-dependently and destroyed cell membrane integrity, activated calpain-1 autolysis, and induced apoptotic protein cleavage in gastric cancer cells. The detection of decreased ATP and mitochondrial membrane potential, ROS accumulation, and cytosolic free Ca2+ elevation confirmed organelles damage in QC4-treated gastric cancer cells. Conclusions. DHA derivative QC4 induced the damage of cytomembrane and organelles which finally lead to oncosis and apoptosis in gastric cancer cells. Therefore, as a derivative of plant derived small molecule DHA, QC4 might become a promising agent in gastric cancer therapy.

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“…Rosin acids including isopimaric acid (IPA), sandaracopimaric acid, and pimaric acid are major bioactive derivatives of Pinus genus member plants. Pharmacological activities of these acids have shown them to exhibit diverse effects including hypocholesterolemic activity [1], antigastric ulcer activity [2], blood glucose lowering activity [3], and macrocyte clumping activity [4]. IPA is a diterpenoid containing a double bond and methyl and ethenyl residues at C-12 that has previously been reported to exhibit antibacterial [5], antitumor [6,7], and hypocholesterolemic activity [8], in addition to being able to prevent high blood pressure via the activation of a large conductance Ca 2+ and K + channel [9,10].…”

Section: Introductionmentioning

confidence: 99%

The LC‐MS/MS‐Based Measurement of Isopimaric Acid in Rat Plasma and Application of Pharmacokinetics

Huang

Cheng

Jun-qin

et al. 2021

BioMed Research International

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Isopimaric acid (IPA) exhibits a diverse array of pharmacological activities, having been shown to function as an antihypertensive, antitumor, antibacterial, and hypocholesterolemic agent. However, few studies of the pharmacokinetics of IPA have been performed to date, and such analyses are essential to explore the in vivo mechanisms governing the biological activity of this compound. As such, we herein designed a selective LC-MS approach capable of quantifying serum IPA levels in model rats using an Agilent HC-C18 column ( 250 mm × 4.6 mm , 5 μm) via isocratic elution with a mobile phase composed of methanol 0.5% formic acid (91 : 9, v/v) at a 1 mL/min flow rate. Ion monitoring at m/z 301.2 [M-H]- was used to quantify IPA levels in plasma samples from these rats, while internal standard (IS) levels were assessed at m/z 455.3 [M-H]-. After validation, this approach was employed to conduct a pharmacokinetic analysis of rats administered IPA via the oral (p.o. 50, 100, or 200 mg/kg) and intravenous (i.v. 5 mg/kg) routes. Analyses of noncompartmental pharmacokinetic parameters revealed that IPA underwent secondary absorption following oral administration to these animals, with the two tested oral doses (50 and 100 mg/kg) being associated with respective absolute bioavailability values of 11.9% and 17.5%. In summary, this study may provide a foundation for future efforts to explore the mechanistic basis for the pharmacological activity of IPA, offering insights to guide its subsequent clinical utilization.

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New Hypocholesterolemic Abietamide Derivatives. II. Synthesis and Hypocholesterolemic Activity of N-Phenyl-.DELTA.8-dihydroabietamides.

Cited by 10 publications

References 0 publications

Abietane Acids: Sources, Biological Activities, and Therapeutic Uses

Abietane Acids: Sources, Biological Activities, and Therapeutic Uses

Dehydroabietic Acid Derivative QC4 Induces Gastric Cancer Cell Death via Oncosis and Apoptosis

The LC‐MS/MS‐Based Measurement of Isopimaric Acid in Rat Plasma and Application of Pharmacokinetics

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