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Medicinal Plant Research in Africa

Medicinal Plant Research in Africa

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1
Monoterpenes and RelatedCompounds from the MedicinalPlants of Africa
Michel Kenne Tchimene
a
 , Christopher O. Okunji 
a ,
 ,Maurice Mmaduakolam Iwu
a
and Victor Kuete
b
a
International Centre for Ethnomedicine and Drug Development, Nsukka,Nigeria,
 b
Department of Biochemistry, University of Dschang, Dschang,Cameroon,
 c
USP Headquarter, Rockville, MD
1.1 Introduction
Monoterpenes are a class of terpenes that consist of two isoprene units and havethe molecular formula C
10
H
16
. They are predominantly products of the secondarymetabolism of plants, although specialized classes occur in some animals andmicroorganisms, and are usually isolated from the oils obtained by steam distilla-tion or solvent extraction of leaves, fruits, some heartwoods, and, rarely, roots, andbark  [1]. In favorable cases they occur to the extent of several percent of the wetweight of the tissue. Conjugated nondistillable forms, e.g., terpene-
β
-
D
-glucoside,are also frequently found, especially in the floral organs. They are the most repre-sentative molecules, constituting 90% of the essential oils, and have a great varietyof structures. Monoterpenes may be linear (acyclic) or they may contain rings.Biochemical modifications such as oxidation or rearrangement produce the relatedmonoterpenoids. They are known for their many biological activities such as anti-microbial, hypotensive, antiinflammatory, antipruritic, antigerminative, antiplasmo-dial, antiesophageal cancer, and anticandidal. The compounds are inexpensive andhave been widely used in flavoring and fragrances since the beginning of the nine-teenth century. More recently, they have played a great role in the pharmaceuticalindustry because of their potential. Monoterpenes are also included in the categoryof nutraceuticals, which represent an industry in excess of US$75.5 billion withprospects of growing to US$167 billion by 2010 [1].
1.2 Biosynthesis and Structural Diversity
Modern methods of separation and structure determination, as well as the advent of radioisotope techniques, have led to a very rapid advance in knowledge of the routeof biosynthesis of this class and the other types of terpenoids over the last 30 years.
Medicinal Plant Research in Africa. DOI: http://dx.doi.org/10.1016/B978-0-12-405927-6.00001-1
©
2013 Elsevier Inc. All rights reserved.
 
Several reviews, of differing completeness, have outlined the routes to terpenoidsand steroids [2
8] in general and monoterpenes in particular [9,10]. One important conclusion that emerges is the accuracy with which chemical theory can predictthe course of the biochemical processes. Enzymes exploit the innate reactivity of their substances, and the biosynthetic routes can be dissected into unit steps suchas elimination, electrophilic addition, and Wagner
Meerwein rearrangement thatare controlled by the stereoelectronic factor known to operate in nonbiologicalsystems. Even the reactivity of apparently nonactivated atoms can usually berationalized in terms of conformational and electronic changes imposed bypostulated substrate
enzyme or substrate
cofactor linkages. The well-establishedpatterns found can be used to asses feasible structures for novel terpenoids and todesign biogenetic-type synthesis.
1.2.1 Biosynthetic Pathways
1.2.1.1 Isoprene Rule
The earliest attempt to rationalize the pattern of structures of the monoterpenes wasthe rule proposed by Wallach in 1887, who envisaged such compounds as beingconstructed from an isoprene unit (
1
) (Figure 1.1). Thirty years later, Robinson extended this isoprene rule by pointing out that in monoterpenes, and such higherterpenes as were then known, the units were almost invariably linked in a head-to-tail fashion, as shown for limone (
2
) and camphor (
3
). However, many higherterpenes and a few monoterpenes were later found not to obey this amended rule,and Ruzicka and his collaborators [11,12] proposed a biogenetic isoprene rule. Thisgeneralization, which is now universally accepted, states that naturally occurringterpenoids are derived either directly or by way of predictable stereospecific cycli-zation, rearrangement, and dimerizations form acyclic C-10, C-15, C-20, and C-30precursors geraniol, farnesol, geranylgeraniol, and squalene, respectively. This ruleimplies a common pathway of biosynthesis for the whole family and any proposalfor irregular biogenetic routes must be treated with reservations.Although isoprene has been formed on pyrolytic decomposition of some mono-terpenes, it is not found in plants, and much speculation has occurred around thenature of the active isoprene of the condensing unit, ranging from apiose to tiglicacid. The C-5 unit was also postulated to arise from degradation of carbohydrates,proteins, amino acids, and many other classes of plant metabolites or by elaborationof acetic acid, ethyl acetoacetate, or acetone. These early views have been well
O
1 2 3
Figure 1.1
 Chemical structure of isoprene unit (
1
),limone (
2
), and camphor (
3
).
2 Medicinal Plant Research in Africa