Comparative chromatographic patterns of leaf exudate components from shrubby aloes

As an aid to taxonomic discussions, patterns of leaf exudate compounds separated by two-dimensional thin-layer chromatography and revealed by staining with Fast Blue B have been obtained for all but one of the Aloe species in Reynolds' Group 19 and Series Arborescentes. Plants in these two subdivisions of the genus are linked by their affinity to A. Arborescens , a widespread species which occurs in both groupings. Three types of compounds can be distinguished by their staining reactions and u.v.fluorescence, the anthrone C-glycosides (yellow, green, blue, grey to brown colour reaction), the chromones (orange colour reaction) and a large mixed group of phenolic compounds, including phenylpyrones (staining various shades of purple).On the basis of patterns containing these chromatographic zones, the shrubby aloes were divided into four arbitary divisions although at this stage no taxonomic implications are claimed, the classification being purely chemical and reflecting differences in their biosynthetic constitution. One species, A.pluridens was peculiar in having an exudate with none of the staining compounds present, although the supposedly secretory 'aloin' cells were prominent in the leaveS. Determination of the partition coefficients of the three main anthrone C-glycosides demonstrates that homonataloin is more lipophilic than barbaloin and might be expected to accumulate in more hydrophobic regions of the cell.     

Secretory tissues in the East African shrubby aloes

Examination of Aloe leaf sections revealed the presence of three types of cells at the phloem pole of the vascular bundles, aloin cells, outer bundle sheath cells and fibres. Three species contain fibres alone and produce a sparse exudate with few components staining purple with Fast Blue B on thin-layer chromatograms. The majority of species have aloin cells of various sizes and in the tetraploid species these produce a copious exudate containing anthraquinone and chromone derivatives. It is suggested that the aloin cells act as storage tissue and that the compounds are synthesized in the surrounding layer of cells of smaller diameter, many of which can be seen to contain globules of unknown constitution. Anatomical observations support the idea that the shrubby tetraploid Aloe species are derived from a form similar to the diploid Aloe morijensis. Two forms of this species have been described, one with fibres only and few exudate components and another with both fibres and aloin cells and an exudate containing compounds of the tetraploid species. A line of diploid plants similar in anatomy and chemistry to the first form is represented by A. fibrosa and A. babatiensis while a line of tetraploids with affinities to the second form is represented by A. nyeriensis, A. cheranganiensis, A. elgonica, A. dawei and A.yavellana.     

A chemotaxonomic and morphological appraisal of Aloe series Purpurascentes, Aloe section Anguialoe and their hybrid, Aloe broomii

Evidence is presented to suggest the hybrid origin of Aloe broomii, with the one putative parent belonging to Aloe series Purpurascentes and the other a member of Aloe series Anguialoe. A chemotaxonomic and morphological assessment is presented for both infrageneric groups and their hypothesised hybrid. Four of the species belonging to the series Purpurascentes display a characteristic leaf exudate profile containing the chemotaxonomic marker microstigmin. Aloe gariepensis and A. succotrina lack the diagnostic leaf exudate compounds. The distinct morphological apomorphies for Aloe section Anguialoe are supported on the chemical level reinforcing the monophyly of this group.     

Comparative chromatographic patterns of leaf exudate components from Aloe Section Pachydendron Haw

Leaf exudates from individuals of 29 species included in Aloe Section Pachydendron have been separated by TLC and HPLC to reveal their phenolic components. All the zones are described by their chromatographic behaviour and UV absorption properties, but not all can be identified as known compounds so are distinguished by an arbitrary code. Section Pachydendron has been shown to be chemically heterogeneous akhough there are some correlations between species said to be taxonomically related. Without attaching taxonomic significance four chemical groupings can be discerned: (1) species in which chromones are prominent; (2) species in which andirone and anthraquinone glycosides are prominent; (3) species containing mainly purple-staining phenolic compounds; and (4) species with few leaf exudate phenolic compounds. This survey emphasizes the uncertain taxonomy of the Section and the need for more extensive collection and analysis.     

The phytochemical profile and identification of main phenolic compounds from the leaf exudate of Aloe secundiflora by high-performance liquid chromatography-mass spectroscopy

The phytochemical profile of Aloe secundiflora (Aloeaceae) and the identity of eight major compounds, including the two main constituents, have been determined from the leaf exudate of this ethnoveterinary used species from Kenya and Tanzania. Analytical HPLC-MS studies of the exudate have revealed that it comprises a mixture of phenolic compounds, mainly anthrones (aloenin, aloenin B, isobarbaloin, barbaloin and other aloin derivatives), chromones and phenylpyrones with a low content of polysaccharides and aliphatic compounds. The high percentage of anthrones in the exudate could provide a first line of evidence for the use of the plant in ethnoveterinary practices.     

Chromones and anthrones from Aloe marlothii and Aloe rupestris

A phytochemical investigation of the leaf exudate of Aloe marlothii has resulted in the isolation of a new chromone (7-O-methylaloeresin A) and a new anthrone (5-hydroxyaloin A 6'-O-acetate). Furthermore 7-O-methylaloesin was isolated as a natural product for the first time from the leaf exudate of Aloe rupestris. The structure elucidation of these compounds was based on spectral data including 2D NMR. The chemotaxonomic value of 7-O-methylaloesin in Aloe series Asperifoliae and section Pachydendron is discussed.     

Identification of major metabolites in Aloe littoralis by high-performance liquid chromatography-nuclear magnetic resonance spectroscopy

Examination of the leaf exudate of the South African species Aloe littoralis by reversed-phase HPLC revealed the presence of two major metabolites. The identification of the two compounds without isolation was attempted by HPLC-NMR based on separation using a C18 column eluting with a deuterium oxide:acetonitrile solvent gradient and an inverse HPLC-NMR probe. For each compound, one-dimensional proton spectra, and two-dimensional homonuclear COSY and TOCSY, and heteronuclear HSQC and HMBC, spectra were collected. On the basis of the data obtained, the metabolites were characterised as 10-hydroxyaloin B and deacetyllittoraloin.     

Distribution and chemotaxonomic significance of flavonoids inAloe (Asphodelaceae)

A chemotaxonomic study of practically all the species of the genusAloe showed that flavonoids occur as major compounds in 31 out of a total of 380 species investigated. Flavanones and dihydroflavonols are present in the exudate of species inAloe ser.Rhodacanthae andSuperpositae and also in a number of the endemic species from Madagascar. Flavones occur as the only major compound in the leaf extracts of the sects.Leptoaloe andGraminialoe. In ser.Macrifoliae and inLomatophyllum, the sister genus ofAloe, isovitexin co-occurred with theC-glucosylanthrone aloin. The chemotaxonomic implication of these results are discussed together with the significance of the taxonomic and chemogeographical distribution of flavonoids inAloe. With a few rare exceptions, the leaf compounds from two different biogenetic pathways (polyketide pathway and flavonoid pathway) are mutually exclusive. Since flavonoids are restricted to the basal groups inAloe, we conclude that flavonoids are plesiomorphic characters inAloe reflecting ancient phylogenetic and biogeographic links.     

The chemotaxonomic significance of the phenyl pyrone aloenin in the genus Aloe

The phenyl pyrone, aloenin was positively identified in 16 species in a greater chemotaxonomic study on 380 species of Aloe. A large number of species have previously been suggested to be related on the basis of their macromorphological characters. The leaf exudate composition of the 16 species are presented together with a summary of the salient morphological characters. The possible taxonomic relationships between aloenin producing species, not previously thought to be associated with one another are discussed and illustrates the need to explore additional characters of taxonomic value in this large genus of ca. 420 species where no natural classification system exists.     

芦荟属3种植物不同叶龄、不同部位叶内蒽醌类物质含量及其变化的研究

用植物化学技术研究了3种芦荟属植物不同叶龄和不同部位叶中蒽醌类物质的含量及其变化。结果表明,被研究的芦荟属3种植物叶中主含的蒽醌类物质有：芦荟素或高那特芦荟素,芦荟宁和芦荟苦素。其中,中华芦荟和木立芦荟主含芦荟素;海莱芦荟主含高那特芦荟素。叶各部位详细分析的结果表明,蒽醌类物质在植株上部的嫩叶中的含量要高于下部老叶;同一叶中,叶尖高于叶中部,叶基含量最低;而叶缘含量高于叶的中央部分。在同一叶的横切面上,蒽醌类物质的含量在维管柬区最高,同化薄壁组织部分次之,储水组织部分最低。芦荟属植物在同一个植物体不同的叶之间,以及同一叶不同的位置间有规律的累积蒽醌类物质有重要的生物学意义。它是保证芦荟属植物在原产地的干旱和半干旱生活环境中得以良好生存的适应反应和化学防御机制。     

A contribution to the phytochemistry of the East African tetraploid shrubby aloes and their diploid allies

Compounds in the leaf exudates of a group of shrubby aloes from East Africa have been re-examined by two-dimensional thin-layer chromatography using Fast Blue B as a revealing reagent. Exudates from the most abundant taxa, the two subspecies of Aloe nyeriensis , were found to contain substances giving four distinct chromatographic patterns. One was distinguished by the presence of the anthrone C-glycoside barbaloin while two others contained instead homonataloin with or without aloenin. The fourth group contained neither of these but a similar compound of unknown constitution. Exudate patterns from the neighbouring but localized tetraploid species A. cheranganiensis , the more remote A. dawei and A. elonica , together with the diploid A. yavellana , related to one or other of the groupings of A. nyeriensis. Some plants of a localized diploid species, A. morijensis , also yielded a similar pattern but other plants of rather more slender form contained quite different compounds resembling those in the diploids A. fibrosa and A. babatiensis. This supports the hypothesis that A. morijensis is close to the putative ancestor of the tetraploid East African shrubby aloes. The other widespread shrubby species in this locality, the diploid A. rabaiensis , is unrelated taxonomically and chemically.     

<Emphasis Type="Italic">In vitro</Emphasis> antileishmanial activity of <Emphasis Type="Italic">Aloe vera</Emphasis> leaf exudate: A potential herbal therapy in leishmaniasis

Aloe vera has wide spread use in health products, and despite several reports on the whole plant and inner gel, little work has been performed on the leaf exudate. Our aim was to evaluate the in vitro efficacy of Aloe vera leaf exudate (AVL) in leishmaniasis. Irrespective of the disease manifestation, promastigotes from strains responsible for cutaneous, mucocutaneous, and visceral leishmaniasis were susceptible to AVL and their IC₅₀ ranged from 100 to 180 μg/ml. In axenic amastigotes cultured from a L. donovani strain 2001 responsible for visceral leishmaniasis, the IC₅₀ was 6.0 μg/ml. AVL caused activation of host macrophages evident by an increased release of members of reactive oxygen species that was attenuated by preincubation with free radical scavengers. Collectively, our data indicates that AVL, via its direct leishmanicidal activity which can be further enhanced by activation of host macrophages, is an effective antileishmanial agent meriting further pharmacological investigations.     

Phytochemistry and antiglycation activity of Aloe sinkatana Reynolds

A new anthraquinone along with 10 known compounds were isolated from the leaves of Aloe sinkatana Reynolds (Aloaceae), and their structures were elucidated as the new compound 2,8-dihydroxy-6-(hydroxymethyl)-1-methoxyanthracene-9,10-dione (1) and the known compounds Aloe-emodin (2), feralolide (3), 1-hydroxy-5-methoxy-3-methyl-9,10 dihydroanthracene 9,10-dione (4), β-sitosterol (5), β-sitosterol with glycosidic bond (6), microdontin (7), homoaloins A (8) and B (9) and aloins A (10) and B (11). Characterization of compounds 1–9 was based on spectral analyses and comparison with reported data, particularly the new compound 1 was identified by 1D- and 2D NMR, mass spectroscopic and X-ray crystallography analyses. Antiglycation activity of the extracts and isolated compounds were carried out using the hemoglobin-δ-gluconolactone and glucose–bovine serum albumin assays. The results obtained showed that MeOH and EtOAc extracts as well as compound 1 showed an inhibitory effect on early stage protein glycation. Compound 1 also showed significant inhibitory effects against glucose-induced advanced glycation end-products.     

The distribution of the phenolic metabolites barbaloin, aloeresin and aloenin as a peripheral defense strategy in the succulent leaf parts of Aloe arborescens

Aloe arborescens is a large, multi-stemmed shrub. It is used as hedge plants to protect agricultural fields or stock and as horticultural plants in gardens. In natural habitats it is one of the very common Aloe species along the Indian Ocean coast of southern Africa, from the Cape, in the south, to Zimbabwe and Malawi in the north. Secondary phenolic metabolites such as barbaloin (Rf 0.31-0.35), aloeresin (Rf 0.25-0.3) and aloenin (Rf 0.51-0.55) have been found to be distributed in the succulent leaves of Aloe arborescens in a peripheral defense strategy. The youngest leaves have the highest content. The terminal third of each leaf has the highest content and the basal third, the lowest. Along the leaf margins, on the top third and adaxial side, the content is the highest and in the base third, the lowest along the leaf center on the abaxial side. Similar relative amounts of these three secondary phenolic metabolites were found in the different leaf locations. The leaf orientation may affect the total content of these three phenols but not their relative amounts in the different parts of the leaves. It is possible that the more often the plant parts are damaged by consumption by animals such as elephants, kudu or insects, the greater the increase of their phenolic metabolites. This increase may reduce or prevent further consumption when the content of the metabolites reaches a certain level. The plants then have a chance to renew themselves.     

Three oxanthrones from Aloe littoralis

The leaf exudate of Aloe littoralis yielded, in addition to the known 10-hydroxyaloin B, two new C-glucoside oxanthrones namely 10-hydroxy-15-O-(2R,3S-nilyl)(6′-O-acetyl)aloin B (littoraloin) and 10-hydroxy-15-O-(2R,3S- nilyl)aloin B (deacetyllittoraloin). Their structures were determined by spectroscopic methods as well as by conversion to the known 10-hydroxyaloin B and nilic acid.     

The chemotaxonomic significance of two bioactive caffeic acid esters,nepetoidins A and B,in the Lamiaceae

A survey of leaf surface constituents in the family Lamiaceae using HPLC with diode array detection revealed the presence of two characteristic phenolic compounds in many species. The distribution of these phenolics in the Lamiaceae was found to be of taxonomic significance, as they were present in the great majority of species investigated for the subfamily Nepetoideae, including representatives of the well-known genera of culinary herbs, mint, rosemary, sage, thyme and basil. In contrast, they were absent from species of the other subfamilies of Lamiaceae studied and from the related families Verbenaceae, Scrophulariaceae, Acanthaceae and Buddlejaceae. The compounds were isolated from Plectranthus crassus and identified by NMR spectroscopy as the known caffeic acid esters (Z,E)-[2-(3,5-dihydroxyphenyl)ethenyl] 3-(3,4-dihydroxyphenyl)-2-propenoate and (Z,E)-[2-(3,4-dihydroxyphenyl)ethenyl] 3-(3,4-dihydroxyphenyl)-2-propenoate, for which the trivial names nepetoidins A and B are proposed. The presence of this pair of caffeic acid esters adds another character to the chemical, palynological and embryological features distinguishing the Nepetoideae from the other subfamilies of Lamiaceae and related families, and supports the view that the Nepetoideae are a specialised and monophyletic group within the family. Nepetoidin B was shown to have a greater antioxidant activity than gallic, rosmarinic and caffeic acids, and showed activity as an insect phagostimulant. Both compounds were antifungal.     

Molecular systematics and conservation of the langurs and leaf monkeys of South Asia

Numerous morphology-based classification schemes have been proposed for langurs and leaf monkeys of South Asia but there is very little agreement between them. An incorrect classification scheme when used as a basis for biogeographic studies can support erroneous hypotheses. Further, lack of taxonomic resolution will also confound conservation efforts, given that conservation biologists use traditional morphology-based-classification schemes to prioritize species for conservation. Here, I have revisited recent molecular phylogenetic studies done on langurs and leaf monkeys of South Asia. Results from these studies are in turn used to derive a rational and scientific basis for prioritizing species for conservation. Molecular data support the classification of langurs of the Indian subcontinent—Hanuman, Nilgiri and purple-faced langurs—in the genus Semnopithecus, whereas Phayre’s leaf monkey along with other Southeast Asian leaf monkeys form another distinct clade (Trachypithecus). The phylogenetic position of capped and golden langurs remains unresolved. Molecular data suggest that they are closely related to each other but this group might have evolved through past hybridization between Semnopithecus and Trachypithecus. Additionally, genetic data also support the splitting of the so-called Hanuman langurs into at least three species. The scores for taxonomic uniqueness of langurs and leaf monkeys of South Asia were revised using this molecular phylogeny-based classification. According to the revised scores, Phayres leaf monkey and golden langur are priority species for conservation followed by capped and Nilgiri langurs.     

芦荟属植物叶内蒽醌类物质的分布与其化学防御的关系

芦荟属植物是一类生长在干旱或半干旱沙漠环境的肉质植物,木立芦荟和海藻芦荟的肉质叶的植物研究结果表明,叶内含高浓度的芦荟素,高那特芦荟素,芦荟苦素和芦荟宁等蒽醌类物质,其中,海莱芦荟整叶的蒽醌类物质总含量占其泌出物干重的44．89％。两种芦荟叶内蒽醌类物质的分布有共同的规律,即幼叶的含量高于老叶;叶上部的含量高于中,基部,叶缘则高于叶的中央。但由于木立芦荟和海莱芦荟的个体形态不同,蒽醌类物质的分布在种间还存在各自的特点,根据实验结果推测,蒽醌类物质在芦荟属植物体内的累积和分布与其化学防御机制有关。     

A systematic study of the Vernonia leopoldi complex (Compositae — Vernonieae)

A systematic study of the Vernonia leopoldi complex was undertaken with the objective of determining the taxonomic status of the species involved within this group. TWo species, i.e. Vernonia leopoldi and V. bipontini have been recognized as distinct based on evidence from morphological studies accompanied by field observations and anatomical studies (particularly trichomes and petioles). Both species have 2n = 36 (first reports). Three new varieties have been recognized within V. bipontini , namely var. bipontini , var. gonderensis and var. caccaensis . A lectotype is selected for V. leopoldi .     

Observations on the phytochemistry of the Aloë leaf-exudate compounds

Exudates from the cut surfaces of Aloë leaves contain compounds, many of which can be recognized by their colour reaction with fast blue B salt after separation on thin-layer chromatograms. About 90 chromatographic zones were observed from c. 240 Aloë species. These included 24 orange-staining zones, 35 purple-staining zones and a variety of zones staining shades of grey, green, blue and brown. A few of these substances have been identified as known compounds. Each of the remaining compounds is given a code according to its colour reaction and each is referred to a standard plant source in which it is prominent. Thus a convenient basis for phytochemical discussions is provided. The distribution of the known compounds in the genus as recorded in the literature is compared with present findings. Chemical relationships often followed accepted taxonomic groupings. In particular, correlations were found among shrubby African species and a group of species from Somalia.