Sources of alpha-, beta-, gamma-, delta- and epsilon-carotenes: a twentieth century review

Fontes de alfa-, beta-, gama-, delta-, e epsilon-carotenos: uma revisão do século XX

REVISÃO

Sources of alpha-, beta-, gamma-, delta- and epsilon-carotenes: a twentieth century review

Fontes de alfa-, beta-, gama-, delta-, e epsilon-carotenos: uma revisão do século XX

José M. Barbosa-Filho^*; Adriana A. Alencar; Xirley P. Nunes; Anna C. de Andrade Tomaz; José G. Sena-Filho; Petrônio F. Athayde-Filho; Marcelo S. Silva; Maria F. Vanderlei de Souza; Emidio V. Leitão da-Cunha

Laboratório de Tecnologia Farmacêutica, Universidade Federal da Paraíba, Caixa Postal 5009, 58051-970 João Pessoa-PB, Brazil

ABSTRACT

Since humans cannot synthesize carotenoids, they depend upon the diet exclusively for the source of these micronutrients. It has claimed that they may alleviate chronic diseases such as cancers. The present communication constitutes a global review of the scientific literature on plants and others organisms that biosynthesize carotenoids, which include the series alpha-, beta-, gamma-, delta- and epsilon-carotenes. The results of the literature survey lists more than five hundred sources.

Keywords: a-Carotene, b-carotene, g-carotene, d-carotene, e-carotene, carotenoids, cancer, review.

RESUMO

Uma vez que os humanos não podem sintetizar carotenóides, dependem exclusivamente da dieta como fonte desses micronutrientes. Tem sido afirmado que eles podem aliviar doenças crônicas, tais como cânceres. O presente artigo constitui uma revisão global da literatura científica sobre plantas e outros organismos que biossintetizam carotenóides, que incluem as séries alfa-, beta-, gama-, delta-, e epsilon-carotenos. Os resultados das listas de pesquisa da literatura mostram mais de quinhentas fontes.

Unitermos: a-Caroteno, b-caroteno, g-caroteno, d-caroteno, e-caroteno, carotensides, câncer, revisão.

INTRODUCTION

The carotenoids constitute the largest class of naturally occurring pigments and have attracted the attention of chemists and biologists since 1831, when an yellow coloring agent named b-carotene was isolated from the carrot (Daucus carota) for the first time. Many treatises have been devoted to the almost 1000 cis-trans carotenoid isomers characterized in nature (Britton, 1984, 1985, 1986, 1989, 1991). Most have 40 carbon atoms, less than 10% are hydrocarbons, most have oxygen functions, and some are conjugated with sugars and other molecules. Major provitamin A in mammals are b-carotene and a-carotene, although g-carotene and approximately 50 other carotenoids also show some nutritional activity. Carotenoids are synthesized in plants from acetyl-coenzyme A by a series of well-defined condensations reactions. The synthesis of carotenoids does not occur in animal tissue; however, when those pigments are ingested in the diet, the animals deposit or modify their basic structure (Olson, 1989).

Most cancers that are common nowadays are not caused by the products of modern industry, but by the lifestyle, especially the diet. The scientific literature is consistent in evidences that it is possible to reduce the risk of acquiring some types of cancer by eating a variety of vegetables and fruits (Steinmetz & Potter, 1996; Federmann & Federmann, 2000). The types of vegetable or fruit that most often appear to be protective against cancer are raw vegetables, followed by allium, carrots, green vegetables, cruciferous vegetables, and tomatoes. Substances present in vegetables and fruit that may help protect against cancer, and their mechanisms, include, allium compounds, flavonoids, protease inhibitors, saponins, phytosterols, carotenoids, vitamins, selenium and dietary fiber. Increment in vegetable and fruit consumption, include also benefits against cardiovascular disease, diabetes, stroke, obesity, diverticulosis, and cataracts (Peto et al., 1981).

In a previous paper this research group has reviewed crude plant extracts and chemically defined molecules with potential antitumor activity for mammary (Moura et al., 2001), cervical (Moura et al., 2002) and ovarian neoplasias (Silva et al., 2003), as inhibitors of HMG CoA reductase (Gonçalves et al., 2000), central analgesic activity (Almeida et al., 2001), employed in prevention of osteoporosis (Pereira et al., 2002), for the treatment of Parkinson’s disease (Morais et al., 2003), with antileishmanial (Rocha et al., 2005), hypoglycemic (Barbosa-Filho et al., 2005), antiinflammatory activity (Falcão et al., 2005, Barbosa-Filho et al., 2006a), inhibitors of the enzyme acetylcholinesterase (Barbosa-Filho et al., 2006b), inhibitors of the angiotensin converting enzymes (Barbosa-Filho et al., 2006c), giardicidal (Amaral et al., 2006), and antileprotic activity (Barbosa-Filho et al., 2007).

This work aims at presenting the main natural sources of carotenoids, which include the series a-, b-, g- , d- and e-carotene.

MATERIAL AND METHODS

An extensive literature search was carried out using the Chemical Abstract, Biological Abstract and in the data bank of the University of Illinois in Chicago - NAPRALERT (Acronym for NAtural PRoducts ALERT), updated to March 2000.

The keywords used (in various combinations) in the search were: plants natural products, carotenoids, alpha-, beta-, gamma-, delta- and epsilon-carotene. The references found in the search were then consulted.

Consultation of various types of literature resulted in the elaboration of a list of occurrence of alpha-, beta-, gamma-, delta- and epsilon-carotene in plants and other organisms. For details the original references should be consulted.

Source of carotenoids

Carotenoids are found almost everywhere in nature, but particularly among organisms that bask in the sun. Those interesting compounds, most of which show a yellow to red color, have attracted the attention of chemists and biologists since at least the early 1800s. The colored compounds in plants and microorganisms were extracted and purified, and in time their structures were determined. Many treatises have been devoted to these compounds (Isler, 1971) the most comprehensive revision were presented by Briton (Britton, 1984, 1985, 1986, 1989, 1991).

We encountered 690 carotenes reported in the literature, 477 are found to be b-carotene, 144 a-carotene, 43 g-carotene, 22 e-carotene and 4 d-carotene, so 310 are found in Dicotyledons, 122 Monocotyledons, 76 algae, 44 Gymnosperms, 22 ferns and allies, 8 lichens, 5 fungi, 4 bacteria and 2 insects.

Orange vegetables, such as carrots, sweet potatoes, winter squash, and pumpkin, are relatively rich sources of b-carotene, as are some fruits, including papaya, mango and cantaloupe. Because of the interest of carotenoids in preventing many types of cancer, it is also important to know which specific plants keep the greatest number of them. We found that Calendula arvensis, C. officinalis, Citrus paradise, Daucus carota and Diospiros kaki biosynthesize a-, b-, g- d- and e-carotenes (Table 1).

Received 13 March 2007; Accepted 26 October 2007

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Publication Dates

• Publication in this collection
  15 Apr 2008
• Date of issue
  Mar 2008

History

• Accepted
  26 Oct 2007
• Received
  13 Mar 2007