Phytochemical Characterization of the Australian (Aboriginal) Medicinal Plant Dolichandrone heterophylla and Influence of Selected Isolated Compounds on Human Keratinocytes
Free accessResearch articleFirst published online September, 2008
Phytochemical Characterization of the Australian (Aboriginal) Medicinal Plant Dolichandrone heterophylla and Influence of Selected Isolated Compounds on Human Keratinocytes
The Miriwoong Aboriginal people of Eastern Kimberley, Western Australia use the leaves and bark of Dolichandrone heterophylla (R. Br.) F. Muell., Bigoniaceae, to treat sores, rashes, grazes, scabies, boils and wounds. Bioassay guided fractionation of an aqueous extract of the leaves and twigs led to the isolation of the known compounds caffeic acid, the phenylethanoids isoacteoside (1) and acteoside (2), and the flavonoids chrysoeriol and luteolin. The structures of these compounds were determined using mass spectrometric and 1D- and 2D-NMR spectroscopic data and verified by comparison with those in the literature. Studies of the effect of isoacteoside (1) and chrysoeriol on HaCaT keratinocytes using the MTT assay revealed that chrysoeriol had growth inhibitory properties towards the cell line in a dose dependent manner (IC50 = 31 μM) whereas 1 was well tolerated up to 50 μM. On the other hand, 1 inhibited the growth of Pseudomonas aeruginosa.
WheelerJR, RyeBL, KochBL, WilsonAJG. (1992) Flora of the Kimberly region. (Department of Conservation and Land Management, Western Australia), 1327pp.
2.
WightmanG. (1994) Gurindji Ethnobotany: Aboriginal plant use from Daguragu, Northern Australia. (Darwin: Conservation Commission of the Northern Territory), 76p.
3.
SinaphetB, NoiarsaP, RujirawatS, OtsukaH, KanchanapoomT. (2006) Dolichandroside, a new phenolic triglycoside from Dolichandrone serrulata WC.) Seem. Journal of Natural Medicines, 60, 251–254.
4.
PrakashL, SinghR. (1980) Chemical constituents of the stem bark and stem heartwood of Dolichandrone Crispa seem. Pharmazie, 35, 122–123.
5.
PearnJ. (2005) The world's longest surviving paediatric practices: Some themes of Aboriginal medical ethnobotany in Australia. Journal of Paediatrics and Child Health, 41, 284–290.
6.
LatzP ed. (1999) A Field Guide to the Plants of Central Australia and their Traditional Uses, Volume 5 (Alice Springs: IAD Press).
7.
HoughtonPJ, HylandsPJ, MensahAY, HenselA, DetersAM. (2005) In vitro tests and ethnopharmacological investigations: Wound healing as an example. Journal of Ethnopharmacology, 100, 100–107.
8.
BoukampP, PetrussevskaRT, BreitkreutzD, HornungJ, MarkhamA, FusenigNE. (1988) Normal keratinization in a spontaneously immortalized aneuploid human keratinocyte cell-line. Journal of Cell Biology, 106, 761–771.
9.
LeeER, KangYJ, KimJH, LeeHT, ChoSG. (2005) Modulation of apoptosis in HaCaT keratinocytes via differential regulation of ERK signaling pathway by flavonoids. Journal of Biological Chemistry, 280, 31498–31507.
10.
PaivaNL. (2000) An introduction to the biosynthesis of chemicals used in plant-microbe communication. Journal of Plant Growth Regulation, 19, 131–143.
11.
WeisshaarB, JenkinsGI. (1998) Phenylpropanoid biosynthesis and its regulation. Current Opinion in Plant Biology, 1, 251–257.
12.
KurkinVA. (2003) Phenylpropanoids from medicinal plants: Distribution, classification, structural analysis, and biological activity. Chemistry of Natural Compounds, 39, 123–153.
13.
AbeF, NagaoT, OkabeH. (2002) Antiproliferative constituents in plants 9. Aerial parts of Lippia dulcis and Lippia canescens. Biological & Pharmaceutical Bulletin, 25, 920–922.
14.
Winkel-ShirleyB. (2002) Biosynthesis of flavonoids and effects of stress. Current Opinion in Plant Biology, 5, 218–223
15.
KyleJ, DuthieG. (2006) Nutritional relevance of flavonoids in disease prevention. Natural Product Communications, 1, 1049–1060.
16.
HatanoT, KusudaM, InadaK, OgawaTO, ShiotaS, TsuchiyaT, YoshidaT. (2005) Effects of tannins and related polyphenols on methicillin-resistant Staphylococcus aureus. Phytochemistry, 66, 2047–2055.
LeeER, KangYJ, KimJH, LeeHT, ChoSG. (2005) Modulation of apoptosis in HaCaT keratinocytes via differential regulation of ERK signaling pathway by flavonoids. Journal of Biological Chemistry, 280, 31498–31507.
19.
LeeER, KimJH, KangYJ, ChoSG. (2007) The anti-apoptotic and anti-oxidant effect of eriodictyol on UV-induced apoptosis in keratinocytes. Biological & Pharmaceutical Bulletin, 30, 32–37.
GrisebachH, BilhuberW. (1967) On the biosynthesis of apigenin and chrysoeriol in parsley. Zeitschrift fur Naturforschung. Teil B: Chemie, Biochemie, Biophysik, Biologie, 22, 746–751.
22.
Baerheim SvendsenA. (1951) On the occurrence of chlorogenus and caffeic acid in the plant family of Umbelliferae; phytochemical analysis with paper chromatography. Pharmaceutica acta Helvetiae, 26, 253–258.
ParisR. (1955) Presence of a luteolin glycoside in weld (Reseda luteola). Annales pharmaceutiques francaises, 13, 485–487.
25.
MosmannT. (1983) Rapid colorimetric assay for cellular growth and survival - Application to proliferation and cyto-toxicity assays. Journal of Immunological Methods, 65, 55–63.
26.
GormannR, KalogaM, FerreiraD, MaraisJPJ, KolodziejH. (2006) Newbouldiosides A-C, phenylethanoid glycosides from the stem bark of Newbouldia laevis. Phytochemistry, 67, 805–811.
SubramanianSS, NairAGR. (1966) Occurrence of chrysoeriol in Rungia repens Nees. flowers. Indian Journal of Chemistry, 4, 461–465.
29.
CemeliE, SchmidTE, AndersonD. (2004) Modulation by flavonoids of DNA damage induced by estrogen-like compounds. Environmental and Molecular Mutagenesis, 44, 420–426.
30.
ChaeS, KimJS, KangKA, BuHD, LeeY, SeoYR, HyunJW, KangSS. (2005) Antioxidant activity of isoacteoside from Clerodendron trichotomum. Journal of Toxicology and Environmental Health-Part α-Current Issues, 68, 389–400.
31.
HartwigUA, MaxwellCA, JosephCM, PhillipsDA. (1990) Chrysoeriol and luteolin released from alfalfa seeds induce Nod genes in Rhizobium-Meliloti. Plant Physiology, 92, 116–122.
32.
ChoiDY, LeeJY, KimMR, WooER, KimYG, KangKW. (2005) Chrysoeriol potently inhibits the induction of nitric oxide synthase by blocking AP-1 activation. Journal of Biomedical Science, 12, 949–959.
33.
RaahaveD. (1974) Paper disk-agar diffusion assay of penicillin in presence of streptomycin. Antimicrobial Agents and Chemotherapy, 6, 603–605.
