Ethnobotanical Survey of Dracaena cinnabari and Investigation of the Pharmacognostical Properties, Antifungal and Antioxidant Activity of Its Resin

Dracaena cinnabari Balf. f. (Dracaenaceae) is an important plant endemic to Soqotra Island, Yemen. Dragon’s blood (Dam Alakhwin) is the resin that exudes from the plant stem. The ethnobotanical survey was carried out by semi-structured questionnaires and open interviews to document the ethnobotanical data of the plant. According to the collected ethnobotanical data, the resin of D. cinnabari is widely used in the traditional folk medicine in Soqotra for treatment of dermal, dental, eye and gastrointestinal diseases in humans. The resin samples found on the local Yemeni markets were partly or totally substituted by different adulterants. Organoleptic properties, solubility and extractive value were demonstrated as preliminary methods to identify the authentic pure Soqotri resin as well as the adulterants. In addition, the resin extracts and its solution in methanol were investigated for their in vitro antifungal activities against six human pathogenic fungal strains by the agar diffusion method, for antioxidant activities using the DPPH assay and for cytotoxic activity using the neutral red uptake assay. The crude authentic resin dissolves completely in methanol. In comparison with different resin extracts, the methanolic solution of the whole resin showed the strongest biological activities. It showed strong antifungal activity, especially against Microsporum gypseum and Trichophyton mentagrophytes besides antioxidant activities and toxicity against FL-cells. These findings confirm and explain the traditional uses of the resin for the treatment of skin diseases and mouth fungal infections.

Related papers:

title: Raman spectroscopy of coloured resins used in antiquity: dragon's blood and related substances.
abstract: Dragon's blood is a deep red resin which has been used for centuries by many cultures and much prized for it's rarity, depth of colour and alchemical associations. The original source of dragon's blood resin is believed to be Dracaena cinnabari from Socotra in Africa, but since mediaeval times there have been several alternatives from different geographical locations from the Canary Islands to the East Indies. Here, the Raman spectra of dragon's blood resins from Dracaena draco Liliacae trees growing in several different locations bordering the Mediterranean and Middle East are compared with the resins from alternative botanical sources such as Daemonorops draco, Dracaena cinnabari and Eucalyptus terminalis, which all generically come under the description of dragon's blood. Key vibrational spectroscopic marker bands are identified in the Raman spectra of the resins, which are suggested for adoption as a protocol for the identification of the botanical and possible geographical sources of modern dragon's blood resins. The Raman spectra of materials, which are falsely attributed to dragon's blood resin are also shown for comparison and identification purposes. Changes in the Raman spectra of genuine dragon's blood resin specimens arising from simple processing treatment during the preparation of the resins for sale are also identified, which suggests a possible attribution characteristic for unknown samples.

title: Raman spectroscopic analysis of dragon's blood resins-basis for distinguishing between Dracaena(Convallariaceae), Daemonorops(Palmae) and Croton(Euphorbiaceae).
abstract: "Dragon[prime or minute]s blood" is the name applied to the deep-red coloured resin obtained from various plants. The original source in Roman times, used by many cultures and esteemed for its depth of colour and mystical association, was the dragon tree Dracaena cinnabari(Convallariaceae), found only on the Indian Ocean island of Socotra, (Yemen). Additional sources emerged later, including another species of Dracaena, D. draco, from the Canary Islands and Madeira, and species in the genera Daemonorops(Palmae) from South East Asia and Croton(Euphorbiaceae) from tropical parts of both the New and Old Worlds. In this study, examples of dragon's blood resins from the Economic Botany Collections at the Royal Botanic Gardens, Kew, dating from 1851 to 1993, have been analysed non-destructively using Raman spectroscopy. The Raman spectra of well-documented, provenanced specimens have been used to establish the source of specimens of questionable or unknown origin. It has also been possible from the Raman spectra to indicate whether processing of the resins has been undertaken in the preparation of the specimens before their deposition at Kew.

title: Identification and differentiation of dragon's blood in works of art using gas chromatography/mass spectrometry
abstract: AbstractDragon's blood is a common but non-specific name for red-coloured resins that are produced by various plants, particularly exudations from plant species belonging to the genera Dracaena and Daemonorops. Although dragon's blood is mentioned in historic sources as a colourant, it has hardly ever been identified in real artworks. This paper reports the identification and discrimination of dragon's blood produced by Dracaena cinnabari, Dracaena draco as well as Daemonorops draco and Daemonorops micracantha by means of gas chromatography/mass spectrometry (GC/MS) within the context of a routine analysis of binding media used in works of art. The detection of specific flavonoid marker compounds in both underivatised and methylated methanol extracts provided the first evidence for the use of dragon's blood from all four species in various works of art from the fifteenth to nineteenth centuries. Dragon's blood was mainly used as a red colourant in gold lacquers as well as translucent glazes and paints, e.g. in reverse-glass paintings (Hinterglasmalerei).
 FigureSplendid and colourful Hinterglasmalerei in the Amelierung technique with gold foils on two panels of the Corning House Altar, ca. 1560–1580, before restoration. The red paints contain dragon’s blood from Dae. draco. The width of the altar with closed wings is 19.5 cm.  Simone Bretz, Oberau,

title: Ethnoflora of the Soqotra Archipelago
abstract: Ethnoflora of the Soqotra Archipelago is an attractive, user-friendly manual to the plants of this little-known but botanically important group of islands, situated off the Horn of Africa and governed by Yemen. Designed as a practical guide for conservationists and planners, as well as students, botanists and others interested in the plant life of the region, this comprehensive volume differs from a standard Flora in two significant ways.

title: Flavylium chromophores as species markers for dragon's blood resins from Dracaena and Daemonorops trees.
abstract: A simple and rapid liquid chromatographic method with diode-array UV-vis spectrophotometric detection has been developed for the authentication of dragon's blood resins from Dracaena and Daemonorops trees. Using this method it was discovered that the flavylium chromophores, which contribute to the red colour of these resins, differ among the species and could be used as markers to differentiate among species. A study of parameters, such as time of extraction, proportion of MeOH and pH, was undertaken to optimise the extraction of the flavyliums. This method was then used to make extracts from samples of dragon's blood resin obtained from material of known provenance. From the samples analysed 7,6-dihydroxy-5-methoxyflavylium (dracorhodin), 7,4'-dihydroxy-5-methoxyflavylium (dracoflavylium) and 7,4'-dihydroxyflavylium were selected as species markers for Daemonorops spp., Dracaena draco and Dracaena cinnabari, respectively. The chromatograms from these samples were used to build an HPLC-DAD database. The ability to discriminate among species of dragon's blood using the single marker compounds was compared with a principal components analysis of the chromatograms in the HPLC-DAD database. The results from the HPLC-DAD method based on the presence of these flavylium markers was unequivocal. The HPLC-DAD method was subsequently applied to 37 samples of dragon blood resins from the historical samples in the Economic Botany Collection, Royal Botanic Gardens, Kew. The method identified anomalies in how samples in this collection had been labelled. It is clear that the method can be used to evaluate the provenance of samples used in different areas of cultural heritage. It also could be used to monitor the trade of endangered species of dragon's blood and the species being used in complex formulations of traditional Chinese medicine.

title: Potential carcinogenicity of homoisoflavanoids and flavonoids from Resina sanguinis draconis (Dracaena cinnabari Balf.).
abstract: Polarographic behavior of three homoisoflavanoids and four flavanoids isolated from the dragon's blood (Resina sanguinis draconis. Dracaena cinnabari Balf.), collected at Sokotra, was investigated in aprotic solution and an index of potential carcinogenicity tg alpha was determined. Generally, homoisoflavanoids and flavanoids were reduced in two two-electron steps, the first being reversible and the second one irreversible. The parameter tg alpha values indicated that the majority of these compounds possesses no or only marginal potential carcinogenic activity. However, it was demonstrated that some structural modifications in basic flavonoid structure lead to changed electrochemical properties and a substantial increase of derivative potential carcinogenicity.

title: Damalachawin, a triflavonoid of a new structural type from dragon's blood of Dracaena cinnabari
abstract: A new triflavonoid, damalachawin, was isolated from dragon's blood of Dracaena cinnabari. Its structure was established mainly by NMR spectroscopy.

title: Flavonoids of dragon's blood from Dracaena cinnabari
abstract: In addition to 7-hydroxy-3-(4-hydroxybenzyl)-8-methoxychroman, 3-(4-hydroxybenzyl)-7,8-methylenedioxychroman, 7-hydroxy-3-(4-hydroxybenzyl)chroman, (±)-7,4′-dihydroxy-3′-methoxyflavan, (2 S )-7-hydroxyflavan, 4,4′-dihydroxy-2-methoxydihydrochalcone, 4,4′-dihydroxy-2′-methoxychalcone, 7,4′-dihydroxyflavone and (2 S )-7-hydroxyflavan-4-one, three new flavonoids have been isolated from the resin, called ‘dragon's blood’, of Dracaena cinnabari , the structures of which have been elucidated as 7-hydroxy-3-(3-hydroxy-4-methoxybenzyl)chroman, (2 S )-7,3′-dihydroxy-4′-methoxyflavan and 4-hydroxy-2-methoxydihydrochalcone.

title: Cinnabarone, a biflavonoid from dragon's blood of Dracaena cinnabari
abstract: A new biflavonoid, cinnabarone, was isolated from dragon's blood of Dracaena cinnabari . Its structure was established, mainly by NMR spectroscopy, as a dihydrochalcone linked by a carbon-carbon bond to a deoxotetrahydrochalcone.

title: Dracophane, a metacyclophane derivative from the resin of Dracaena cinnabari Balf.
abstract: Dracophane, a novel structural derivative of metacyclophane, was isolated from the resin of Dracaena cinnabari Balf. The structure of this compound was determined by spectroscopic methods to be 3,12,21-trihydroxy-1,10,19-tris(4-hydroxyphenyl)-5,14,23-trimethoxy[3.3.3]metacyclophane.

title: Chemoprotective potentials of homoisoflavonoids and chalcones of Dracaena cinnabari: modulations of drug‐metabolizing enzymes and antioxidant activity
abstract: A series of homoisoflavonoids and chalcones, isolated from the endemic tropical plant Dracaena cinnabari Balf. (Agavaceae), were tested for their potential to inhibit cytochrome P4501A (CYP1A) enzymes and Fe‐enhanced in vitro peroxidation of microsomal lipids in C57B1/6 mouse liver. The effects of the polyphenolic compounds were compared with those of prototypal flavonoid modulators of CYP1A and the well‐known antioxidant, butylated hydroxytoluene. 2‐Hydroxychalcone and partly 4,6‐dihydroxychalcone were found to be strong inhibitors of CYP1A‐dependent 7‐ethoxyresorufin O‐deethylase (EROD) activity in vitro comparable to the effects of quercetin and chrysin. The first screening of flavonoids and chalcones of Dracaena cinnabari for antioxidant activity was done in an in vitro microsomal peroxidation assay. While chalcones were shown to be poor antioxidants, 7,8‐methylenedioxy‐3(4‐hydroxybenzyl) chromane, as one of the tested homoisoflavonoids, exhibited a strong antioxidant activity comparable to that of the strongest flavonol antioxidant, quercetin.

title: Medical ethnobotany of the Yucatec Maya: Healers’ consensus as a quantitative criterion
abstract: Medical Ethnobotany of the Yucatec Maya: Healers’ Consensus as a Quantitative Criterion. Economic Botany 53(2):144–160, 1999. There is an urgent need to obtain information on the relative importance of a taxon used medicinally as compared to others within the same culture. This was achieved through a documentation of the current indigenous medical uses of 320 species in three Yucatec Maya communities during 18 months of fieldwork. The 1549 individual reports documented were divided into nine groups, which classify indigenous uses. The frequency of usage of the individual plants reported was employed in the analysis of the ethnobotanical importance of the respective taxa. Species cited more frequently in a group of indigenous uses are regarded to be of greater ethnobotanical importance than those cited only by a few informants. In order to obtain information on possible biological, pharmacological and toxicological effects of some particularly important species, the scientific literature on these taxa was evaluated systematically. The study is the basis for phytochemical and pharmacological evaluations of the traditional uses.ResumenSe considera esencial la documentación de la importancia relativa que un taxon de uso medicinal tiene, en comparación con otros taxones dentro de una misma cultura. Con este propósito se realizó un estudio etnobotánico de 18 meses, investigando el uso de 320 especies en très comunidades Mayas del Estado de Yucatán (México). Se documentaron 1549 usos indigenas, que se clasificaron en 9 grupos. Se utilizó el numero de usos indígenas para determinar la importancia relativa de cada especie; así, las especies medicinales que fueron citadas con mayor frecuencia se consideran las de mayor importancia, mientras que las especies citadas con menor frecuencia son las de menor importancia. Para evaluar los usos indigenas se obtuvo información sobre efectos biológicos, farmacológicos y toxicológicos de las especies, através de una revisión sistemática de la literatura científica. Este estudio es la base para la selección de plantas que se evaluarán en estudios fitoquímicos y farmacológicos.

title: Antimicrobial activity of some medicinal plants of the island Soqotra.
abstract: Twenty-five selected plants belonging to 19 families were collected from different localities of the island Soqotra, dried and extracted with the solvents chloroform, methanol and hot water to yield 80 extracts. The extracts were tested for their antimicrobial activity against several Gram-positive and Gram-negative bacteria and against one yeast species using agar diffusion method. Antibacterial activity was demonstrated especially against Gram-positive bacteria including multiresistant Staphylococcus strains. The greatest activity was exhibited by the methanolic extracts of Boswellia elongata, Boswellia ameero, Buxus hildebrandtii, Commiphora parvifolia, Jatropha unicostata, Kalanchoe farinacea, Pulicaria stephanocarpa, Punica protopunica, Withania adunensis and Withania riebeckii. Only the methanolic extract of Buxus hildebrandtii displayed significant antifungal activity.

title: Flavonoid dimers from the total phenolic extract of Chinese dragon's blood, the red resin of Dracaena cochinchinensis.
abstract: Eight new flavonoid dimers, named cochinchinenins I-M (1-5), including three pairs of enantiomers (1a/1b-3a/3b) and two optically pure flavonoid dimers (4-5), along with a known analogue (6), were isolated from total phenolic extract of the red resin of Dracaena cochinchinensis (Chinese dragon's blood). The planar structures of 1-5 were elucidated by extensive spectroscopic analysis including HRESIMS and 1D/2D NMR. Their absolute configurations were determined on the basis of experimental and calculated electronic circular dichroism (ECD) data. Compounds 4 and 5 exhibited significant inhibition of nitric oxide production in lipopolysaccharide-stimulated BV-2 microglial cells with IC50 value of 4.9±0.4 and 5.4±0.6μM, respectively.

title: Flavans of dragon’s blood from Dracaena draco and Dracaena tamaranae
abstract: Flavans of D. draco subsp. draco and subsp. ajgal and of D. tamaranae were isolated and identified for a chemotaxonomic survey. A major constituent of all taxa was (2 S )-4,7′-dihydroxy-8-methylflavan.

title: In vitro antifungal activity of dragon's blood from Croton urucurana against dermatophytes.
abstract: Based on ethnobotanical approach, the dragon's blood collected from Croton urucurana Baill. bark (Euphorbiaceae) was tested for antifungal activity against five dermatophytes by paper disk diffusion method. The minimal inhibitory concentration (MIC) showing no visible fungal growth was also determined, using tube dilution technique. The test dermatophytes were Tricophyton tonsurans, Trichophyton mentagrophytes, Trichophyton rubrum, Microsporum canis and Epidermophyton floccossum. The dragon's blood (0.175-3.0 mg/ml) exhibited an inhibition zone range of 7.6-26.9 mm against all the tested fungi with minimal inhibitory concentrations of 1.25-2.5 mg/ml.

title: The useful plants of Tambopata, Peru: I. Statistical hypotheses tests with a new quantitative technique
abstract: This paper describes a new, simple, quantitative technique for evaluating the relative usefulness of plants to people. The technique is then compared to the quantitative approaches in ethnobotany that have been developed recently. Our technique is used to calculate the importance of over 600 species of woody plants to non-indigenous mestizo people in Tambopata, Amazonian Peru. Two general classes of hypotheses are formulated and tested statistically, concerning (1) the relative importance of different species, and (2) the importance of different families. The plant families are compared with respect to all uses, and with respect to five broad groups of uses. Palms, Annonaceae, and Lauraceae were found to be the most useful woody plant families. On average, the 20 largest woody plant families are most important to mestizos for subsistence construction materials, followed in descending order by commercial, edible, technological, and medicinal uses.ResumenEn éste estudio se describe una nueva técnica cuantitativa para la evaluation de la relativa utilidad de plantas a la gente. Esta técnica se compara con aquellas técnicas cuantitativas recientemente desarrolladas en etnobotánica. Con ésta técnica nosotros estimamos la importantia que las plantas lenosas, más de 600 especies, tienenpara los mestizos de Tambopata de la Amazonia del Peru. Estadisticamente, se prueban dos hipótesis generates concernientes a (1) la relativa importantia de especies diferentes, y a (2) la importantia de diferentes familias. Las familias de plantas son comparadas entre ellas en relation a todos los usos, y con respecto a cinco grupos amplios de usos. Se descubrió que lasfamilias leńosas mas útiles son las palmeras, Annonaceas, y Lauraceas. En término promedio, las 20 familias mas grandes de plantas leñosas tienen prioridad como materiales de constructión de subsistencia, seguidas en orden descendiente por sus usos comerciales, comestibles, tecnológicos, y medicinales.

title: Use of a Free Radical Method to Evaluate Antioxidant Activity
abstract: The antiradical activities of various antioxidants were determined using the free radical, 2,2-Diphenyl-1-picrylhydrazyl (DPPH*). In its radical form. DPPH* has an absorption band at 515 nm which dissappears upon reduction by an antiradical compound. Twenty compounds were reacted with the DPPH* and shown to follow one of three possible reaction kinetic types. Ascorbic acid, isoascorbic acid and isoeugenol reacted quickly with the DPPH* reaching a steady state immediately. Rosmarinic acid and δ-tocopherol reacted a little slower and reached a steady state within 30 min. The remaining compounds reacted more progressively with the DPPH* reaching a steady state from 1 to 6 h. Caffeic acid, gentisic acid and gallic acid showed the highest antiradical activities with a stoichiometry of 4 to 6 reduced DPPH* molecules per molecule of antioxidant. Vanillin, phenol, γ-resorcylic acid and vanillic acid were found to be poor antiradical compounds. The stoichiometry for the other 13 phenolic compounds varied from one to three reduced DPPH* molecules per molecule of antioxidant. Possible mechanisms are proposed to explain the experimental results.