Much research has been conducted in an attempt to fit the so-called plant secondary substances into the general framework of plant metabolism. Though some success has been achieved in this area, e.g., chlorogenic acid as a regulator of plant metabolic systems under stress21, most such studies have met with a conspicuous lack of success. Possible metabolic roles for the plant alkaloids as intermediate metabolites have probably received the greatest such attention and it was concluded at an early stage44 that, since a definitive metabolic role could not be assigned to alkaloids, they best be considered as plant waste products. More recent workers in the field of alkaloid biochemistry have concurred with this evaluation44,83 and the “waste product hypothesis” has been expanded, principally by Muller (1969, 1970), to include plant secondary substances in general.

Toward a general theory of plant. antiherbivore chemistry

A crude MeOH extract of Syzygium aromaticum (clove) exhibited preferential growth-inhibitory activity against Gram-negative anaerobic periodontal oral pathogens, including Porphyromonas gingivalis and Prevotella intermedia. By means of bioassay-directed chromatographic fractionation, eight active compounds were isolated from this extract and were identified as 5,7-dihydroxy-2-methylchromone 8-C-beta-D-glucopyranoside, biflorin, kaempferol, rhamnocitrin, myricetin, gallic acid, ellagic acid, and oleanolic acid, based on spectroscopic evidence. The antibacterial activity of these pure compounds was determined against Streptococcus mutans, Actinomyces viscosus, P. gingivalis, and P. intermedia. The flavones, kaempferol and myricetin, demonstrated potent growth-inhibitory activity against the periodontal pathogens P. gingivalis and P. intermedia.

Compounds from Syzygium aromaticum possessing growth inhibitory activity against oral pathogens

Occurrence and distribution of free flavonoid aglycones in plants

The aim of this review is to summarize the various naturally occurring chalcone compounds which have been isolated from different plants. Chalcones considered as obligate intermediated in flavonoid biosynthesis but they do not accumulate to appreciable degree in most plants. The largest number of natural chalcones has been isolated from species of the Leguminosae, Asteraceae and Moraceae families. Chalcone accumulating plants have often been used in traditional medicine and chalcones have therefore been studied and reported to possess many beneficial biological effects including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and chemopreventive activities. Previously published reviews on this topic survey the biological activities of natural and synthetic chalcones but there are no comprehensive contributions on occurrence and biological activities of natural chalcones. The present study provides an overview of hydroxy or/and methoxy-substituted chalcones, methylated, prenylated, geranylated and other monomeric derivatives, chromeno- and furanochalcones, dimeric chalcones and dihydrochalcone derivatives focusing on their biosynthesis, natural sources and biological activities. On the basis of 608 references, this review covers the phytochemistry and biological activity of natural chalcones, describing 646 compounds have been appeared in the literature since 1975. The summary is aimed to initiate further pharmacobotanical, biotechnological and medicinal studies on the field of chalcone research. This contribution reviews some of the general aspects of naturally occurring chalcones including their chemical categories, focusing on plant sources and biological activities. The review covers the major works appeared in the literature from 1975 up to 2014, relating to 608 references and 646 compounds.

Naturally occurring chalcones and their biological activities

Most reports on the identification of known flavonoids in new plant sources as well as those on novel flavonoids naturally deal with the two most abundant classes, the flavones and flavonols. For this chapter we have listed all references to the occurrence of flavone and flavonol aglycones which have appeared from 1975 to 1980, and also include such earlier references as were overlooked in the relevant chapters of The Flavonoids’ (1975). Emphasis is given to the natural distribution of these compounds. The data are collected in Tables 4.1 and 4.2 which cite substances, plant sources and references. Since 1974, some 50 flavones and 60 flavonols with common substitution patterns have been described as novel compounds. Many are simply new methyl ethers of known compounds. The structures are arranged throughout the Tables by number and arrangement of substituents in ring A, followed by ring B. Wherever possible, the plant organs from which the compounds have been isolated are cited. In cases where authors have extracted the ‘whole plant’ or ‘aerial parts’, it does not necessarily follow that the compound is present in all parts, since these substances are often specifically located in certain organs only. In all cases where free aglycones are encountered, especially highly methylated flavonoids, it is likely that they occur externally, or are associated with secretory structures and are correlated with the production of other lipophilic secondary compounds, mainly of terpenoid origin.

Masayuki Sakakibara

Papers

Flavonoid methyl ethers on the external leaf surface of Larrea tridentata and L. Divaricata

New 8-hydroxyflavonols from Larrea tridentata

Asebotin and its aglucone from three species of Rhododendron

6,8-di-C-glucosylflavones from Larrea trident at a (Zygophyllaceae)