Cat’s Claw

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This entry is adapted from the peer-reviewed paper 10.3390/appliedchem2010001

Cat’s claw (Uncaria tomentosa (Willd. ex Schults) DC.), a plant that is exceptionally rich in phytochemicals, has been used for centuries by the indigenous people of South and Central America as a therapeutic and is currently widely exported for medicinal purposes

cat’s claw medicinal plants antibiotics

1. Introduction

Medicinal plants and their natural products have been a source of important drug discoveries for decades. Since 1981, of the 1394 small-molecule drugs approved by the FDA, 930 of them were derived, to some extent, from a natural product, with fourteen being direct isolates from medicinal plant sources ^[1]. Many of these medicinal plants continue to be a primary therapeutic source for a large portion of the population in developing countries in Asia, South America, and Africa. The family Rubiaceae contains many of these plants, of which the genus Uncaria is prominent. This entry focuses on Uncaria tomentosa (Willd. Ex Schults) DC., commonly referred to as “cat’s claw”, a plant that is native to South and Central America. The name of this woody vine was derived from the long, cat claw-like thorns protruding from the stem at its leaf junctions.

The interest in the specific phytochemical composition of U. Tomentosa comes from the plant’s long history of medicinal use by indigenous people in the region. Peruvian tribes such as the Ashaninka, Aguarurna, Cashibo, and Shipibo have used the plant for centuries to treat a multitude of ailments. Documentation from these cultures have indicated its use as a therapeutic for allergies, arthritis, asthma, diabetes, cancer, bacterial and viral infections, and other medicinal uses ^[2]. Scientific investigations into U. tomentosa extracts and constituents have uncovered a range of biological activities, such as antioxidant, anti-inflammatory, antimicrobial, antiviral, and immunomodulating activity ^[3]^[4]^[5].

Of the biological activities and potential medicinal purposes, this review focuses on its antibacterial properties. As a traditional medicine, U. tomentosa has been documented in wound treatment, indicating potential as an antibacterial agent ^[2]. Recent investigations of the plant and its extracts have produced in vitro evidence of antibacterial activity ^[6]^[7]^[8]^[9]^[10]. Antimicrobial activity has been observed against both the latent and active forms of the bacterium Borrelia burgdorferi, the bacterium responsible for Lyme disease ^[11]^[12]. Lyme disease is a tick-borne ailment brought on by the introduction of Borrelia burgdorferi to a host through a tick bite. Recent Centers for Disease Control (CDC) investigations have indicated that as many as 300,000 Americans are affected by Lyme disease every year ^[13]^[14]. Improved antibiotic therapies capable of not only treating the initial symptoms of B. burgdorferi infections, but also preventing and treating persistent infections are needed. The in vitro anti-borrelia efficacy demonstrated by U. tomentosa warrants an investigation into the possibility of identifying the constituent or a combination of constituents responsible for this effect.

2. Alkaloids

Alkaloids are heterocyclic compounds that contain one or more nitrogen atoms in the structure. They are secondary metabolites generally derived from amino acids and found in a wide range of plants, with an estimated 12,000 molecules identified from natural sources ^[15]. The structural definition of alkaloids allows for the inclusion of structurally diverse compounds in the class, resulting in a wide range of bioactivities ^[16].

There are various systems of nomenclature used to discuss the structural diversity found in alkaloids. Biological sources, structural motifs, and biogenesis pathways are a few ways to classify alkaloids ^[17]^[18]. In this review, the grouping and discussion of alkaloids focus on using a method of chemo-molecular classification based on the structural motifs surrounding the nitrogen-containing heterocyclic portion of the molecule. The alkaloids of Uncaria tomentosa contain a variety of structures that were classified into two groups: indole alkaloids and oxindole alkaloids. These groups were further classified into subclasses defined as tetracyclic and pentacyclic indoloquinolizidine, β-carboline-type, and tetracyclic and pentacyclic oxindole alkaloids.

3. Polyphenols

The term polyphenol is a broad term that encompasses a large range of compounds. Structurally, all polyphenols contain hydroxyl groups attached to aromatic rings; however, the number of hydroxyl groups as well as the size of these compounds could range from a single benzene ring to a series of fused rings up to 4000 Daltons. This class of compounds is structurally diverse with a variety of carbon skeletal arrangements that make up several different groups of compounds including flavonoids, proanthocyanidins, and phenolic acids.

Polyphenols are found in all types of plants and can vary widely in structure and content. These compounds are all bio-generated through the shikimate/phenylpropanoid or the acetate/malonate secondary metabolic pathways ^[19]. The role of these compounds range from defensive functions such as antimicrobial and antifungal activities to cell wall strengthening and repair ^[20]. Polyphenols exhibit antioxidative capabilities as well as solubility in water ^[19]. As a result, these compounds have a diverse array of bioactivities and are generally considered key components to a healthy diet when consumed from natural plant sources ^[21]^[22]. The polyphenol fraction of U. tomentosa includes a variety of compounds.

4. Terpenes

Terpenes or terpenoids are a large and diverse group of naturally occurring compounds found in a wide variety of plants. These secondary metabolites have a history of medicinal use, as their plant sources have been utilized as folk medicines for hundreds of years ^[23]. Terpenes continue to be used for medicinal applications to this day with various bioactivities reported due in part to the wide structural diversity of these natural compounds ^[24]. Antibacterial activity has been reported for this class, especially against Gram-positive bacteria ^[25]. The mechanism for the antibacterial efficacy is likely due to their lipophilic features which allows these compounds to penetrate microbial cell walls ^[26]. However, their lipophilic features make them relatively insoluble and difficult to work with respect to medicinal applications.

All terpenes are comprised of isoprene units, a 5-carbon structural unit. These units are assembled via condensation reactions of dimethylallyl diphosphate (DMAPP) with one or more iso-pentenyl diphosphates (IPP) to afford a 10 carbon intermediate geranyl diphosphate (GPP), 15 carbon farnesyl diphosphate (FPP), or 20 carbon geranylgeranyl diphosphate (GGPP) ^[27]. Larger carbon chains can then be formed from a condensation reaction of FPP and GGPP to form intermediates for terpenoids with up to 40 carbons ^[27]. The resulting terpenoid is typically classified as a mono-, sesqui-, di-, tri-, or tetra-terpenoid based on the number of isoprene units that comprise its carbon skeleton. Acyclic terpenoids formed from these reactions are then formed into cyclic structures via a cascade reaction catalyzed by plant enzymes ^[28]. The diversity of the structures created from the biosynthesis reactions is a current topic of research and investigation. More than 100 cyclical scaffolds of triterpenes have been identified, demonstrating the large structural diversity this class of compounds has to offer ^[29].

The types of terpenoids identified and extracted from U. tomentosa to date include pentacyclic acid triterpenes of various skeletal structures including ursolic, oleanolic, quinovic, cincholic, saponins, phytosterols, and a single monoterpene. The references in which these compounds were isolated and characterized will be cited, as well as any instances of antibacterial activity noted for these compounds whether sourced from U. tomentosa or other plant sources.

References

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Zhang, Q.; Zhao, J.J.; Xu, J.; Feng, F.; Qu, W. Medicinal uses, phytochemistry and pharmacology of the genus Uncaria. J. Ethnopharmacol. 2015, 173, 48–80.
Heitzman, M.E.; Neto, C.C.; Winiarz, E.; Vaisberg, A.J.; Hammond, G.B. Ethnobotany, phytochemistry and pharmacology of Uncaria (Rubiaceae). Phytochemistry 2005, 66, 5–29.
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