Inhibition of HIV Infection by Caffeoylquinic Acid Derivatives

Abstract

The caffeoylquinic acids 3,4,5-tri-O-caffeoylquinic acid (1) and 4,5-di-O-caffeoylquinic acid (2), as well as caffeic acid (4) and synapoic acid (5) were isolated from the plant Securidaka longipedunculata (polygalaceae). 1 exhibited a greater selective inhibition of HIV replication than 2 which had an anti-HIV activity similar to that of 3,4,5-tri-O-galloylquinic acid (3), isolated from Guiera senegalensis (combretaceae); 4 and 5 were ineffective and the structurally related compound rosmarinic acid (6) had only slight anti-HIV activity. Studies of the actions of these compounds suggest that inhibition of the viral reverse transcriptase in vitro is non-specific and that they act by specific binding to gp120 which prevents its interaction with CD4 on T-lymphocytes and thus inactivates virus infectivity.

Review of the genus Ipomoea: traditional uses, chemistry and biological activities

“…This research opens the possibility for the use of these substances as a food additive and a remedy for the prevention and treatment of diabetes and obesity (Okudaira et al, 2005). Isochlorogenic acids a, b and c (24-26) are also found in other species of Ipomoea, such as I. batatas and I. pes-caprae and exhibited colagenase inhibitory and were almost nocytotoxic (Teramachi et al, 2005), beyond to showed radical scavenging activities (Islam et al, 2003) and inhibition of HIV infection (Mahmood et al, 1993;Islam et al, 2002a). Isochlorogenic acids a (24) presents still antifungal activity (Stange et al, 2001) and significant anti-spasmodic activity (Trute et al, 1997).…”

“…Chlorogenic acid (23) and 3,4,5-tri-O-caffeoylquinic acid (27) were also found in I. batatas. These compounds are also inhibitors of HIV replication (Mahmood et al, 1993) and present hypoglycaemic (Okudaira et al, 2005), radical scavenging (Islam et al, 2003) and antimutagenic (Yoshimoto et al, 2002) activities. Chlorogenic acids were not detected in the root.…”

Enzymatic Production of Caffeic Acid by Koji from Plant Resources Containing Caffeoylquinic Acid Derivatives

“…4,17,18) The koji extract also hydrolyzed the crude polyphenolic extract of sweetpotato, burdock, and mugwort leaves to CA (Fig. 3).…”

Chlorogenic Acid Profiles and Antioxidant Potentials of 17 Sweet Potato Varieties Cultivated in Korea: Impact of Extraction Condition and Classification by Hierarchical Clustering Analysis

“…Sweet potatoes have been reported to have a range of beneficial functionalities due to high contents of chlorogenic acids. The chlorogenic acids extracted from sweet potato were found to inhibit the growth of human colon, leukemia, and stomach cancer cells, to ameliorate diabetes in humans, and to inhibit growth of viruses and fungi [3][4][5][6]. Caffeoyl quinic acids isolated from Japanese sweet potato leaves exhibited antimutagenic activities J ournal of Food Chemistry & Nanotechnology Impact of solvent system on the chlorogenic acids extraction from sweet potatoes Sweet potatoes were first sliced into thin pieces, then freeze-dried and ground to make fine powder to pass through a 150 mm sieve.…”