ChemInform Abstract: Analogues of Poison Ivy Urushiol. Synthesis and Biological Activity of Disubstituted n‐Alkylbenzenes.

Abstract

Ausgehend von Phenol (I), m‐ (XV) und p‐Dimethoxybenzol (XX), Veratrumaldehyd (X) und Resorcin (XVIII) werden nach dem im Schema angegebenen Reaktionsfolgen einige Isomere wie (XIV), (XIX) und (XXII) und einige Analoge wie (VII), (IX) und (XVII) des 3‐Pentadecylcatechols (XXIII) (PDC) hergestellt.

Quantification of allergenic urushiols in extracts of Ginkgo biloba leaves, in simple one‐step extracts and refined manufactured material (EGb 761)

“…Isourushiols (5), which were not quantified in this study because of the non-availability of reference compounds, are known for similar skin irritant capacities at dose levels of 3 and 10 µg (ElSohley et al, 1986). The cutaneous toxicity of long chain phenols and diphenols are also described in the work of Baer et al (1967) where doses of 11 and 22 nM for urushiol 4d and 5 were effective in the generation of erythema in 50% of the animals tested.…”

Anacardiaceae Lindl.

“…Cross -reactivity between the allergic responses solicited by various genera is common (Keil et al 1944;ElSohly et al 1986). The resin canals that contain the allergens do not open to the surface; thus, sensitization occurs only when the surface of the plant is disrupted.…”

“…All have 15 carbon monoene or diene side chains, which, as is typical of the family, are closely related chemically and allergenically to the catechol -derived urushiols in Toxicodendron (poison ivy) (Keil et al 1945b;Mitchell and Rook 1979). Species of Anacardium, Schinus, and Toxicodendron share similar toxicants, and there is considerable allergic cross -reactivity among them (Keil et al 1945a;ElSohly et al 1986). These derivatives are referred to as cardanol 15:0, 15:1, and 15:2, based upon the number of side chain carbons and double bonds.…”

“…The toxicants of Schinus are of the same type as those in these genera, and thus it is not surprising that susceptible individuals exhibit considerable cross -reactivity (Keil et al 1945a ;ElSohly et al 1986 ). The toxicants of Schinus are of the same type as those in these genera, and thus it is not surprising that susceptible individuals exhibit considerable cross -reactivity (Keil et al 1945a ;ElSohly et al 1986 ).…”

Synthesis of Sildenafil Analogues from Anacardic Acid and Their Phosphodiesterase-5 Inhibition

“…The presence of a long alkyl chain in anacardic acid is attributed to a variety of biological activities, such as antibacterial activity (10,11), antimicrobial activity (12), prostaglandin synthase inhibition (13), and tyrosinase (14) and lipoxygenase inhibition (15). To explore the potential of anacardic acid, it was extensively derivatized to drug analogues by several researchers (16,17). By considering biological and industrial application of CNSL constituents, we have developed a novel method for comprehensive isolation of all major phenolic constituents of CNSL (18).…”