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CHEMOTAXONOMY of the CUPRESSACEAE. by P. A. GADEK School of Botany University of New South Wales February, 1986. Thesis Submitte

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CHEMOTAXONOMY of the CUPRESSACEAE. by P. A. GADEK School of Botany University of New South Wales February, 1986. Thesis Submitte CHEMOTAXONOMY OF THE CUPRESSACEAE. by P. A. GADEK School of Botany University of New South Wales February, 1986. Thesis submitted for the degree of Doctor of Philosophy. DECLARATION. "I hereby declare that this thesis is my own work and that, to the best of my knowledge and belief, it contains no material previously published or written by another person nor material which to a substantial extent has been accepted for the award of any other degree or diploma of a university or other institute of higher learning, except where due acknowledgement is made in the text of the thesis." ABSTRACT. The aim of this thesis was to extend the data base of the Cupressaceae s.s. by a survey of leaf biflavonoids, and to apply this, with other available data, to a critical reassessment of the current tribes and subfamilies. The biflavonoids in ethanolic leaf extracts of representatives of all genera were analysed by thin layer chromatography. Compounds were identified by chromatographic comparisons with a range of standards, by colour of fluorescence after spraying with an ethanolic solution of AlCu, shifts in UV absorption spectra, as well as permethylation. TLC of permethylated raw extracts proved to be a sensitive method of detecting the range of biflavonoid skeletons present in each species. While there was a high degree of uniformity in the biflavonoid series present in most genera, marked discontinuities were detected within Calocedrus, Chamaecyparis and Thuja. A reassessment of these genera on a broad -range of available data led to the resurrection of two genera, Heyderia and Callitropsis, a redefinition of Thuja as a monotypic genus and the erection of a new genus, Neothuja, to encompass the species removed from Thuja. Outgroup comparisons indicate that the presence of the amentoflavone series is pleisomorphic in the family, while the presence of the cupressuflavone and taiwaniaflavone series, and the absence of the hinokiflavone series are apomorphs. Marked discontinuities in biflavonoid patterns did not correlate with current tribal and subfamily groupings, but allowed the recognition of 4 groups, 3 of which are defined by synapomorphs. A consideration of available data indicated some support for these groups, but there are many gaps in the data base which must be filled before a more satisfactory taxonomy can be constructed. A method for the localisation of biflavonoids in fresh leaf sections using aluminium chloride-induced fluorescence is described. This revealed that biflavonoids accumulated in the cuticle and the cutinised outer periclinal and anticlinal walls of the epidermis in a broad range of biflavone-containing taxa. Confirmation was gained by chromatographic analysis of epidermal peels, cuticular scrapings and middle-leaf tissue fractions in Agathis robust& It is postulated that biflavones serve a protective role against invasion of the leaf by microorganisms and/or attack by leaf-eating insects. ACKNOWLEDGEMENTS. I am indebted to Dr C. J. Quinn for his advice, assistance and considerable encouragement which enabled this thesis to be completed. Thanks are due also to: Assoc. Prof. A. E. Ashford for assistance and advice on GMA sectioning and histochemical staining; Dr I. McFarlane for advice on the techniques of HPLC, Mass Spectroscopy and Nuclear Magnetic Resonance Spectroscopy; Dr L. A. S. Johnson, Director, for permission to sample specimens in the Royal Botanic Gardens and the National Herbarium of NSW; Mr D. Symon, Waite Institute, University of Adeliade, South Australia, for providing specimens from the Waite Arboretum; Dr G. D. McPherson, Herbarium, Missouri Botanic Gardens, USA, for collections of Neocallitropsis; and to the staff and postgraduate students of the School of Botany, University of New South Wales. STATEMENT. It should be noted that, according to article 29 of the International Code of Botanical Nomenclature, this thesis does not qualify as an effective and valid publication. Therefore, descriptions of new genera or new combinations contained herein are not validly published. TABLE OF CONTENTS. Declaration. Abstract. Acknowledgements. Statement. 1. TAXONOMIC HISTORY. 2. BIFLAVONOIDS. 2.1 Introduction. 2.2 Distribution and use in Taxonomy. 2.3 Distribution in the Cupressaceae. 3. TECHNIQUES. 3.1 Plant material. 3.2 Extraction and Isolation. 3.2.1 Thin Layer Chromatography. 3.2.2 High Performance Liquid Chromatography. 3.3 Identification. 3.3.1 Reference Compounds. 3.3.2 Determination of Interflavonoid Linkage. 3.3.2.1 Reaction with Aluminium Chloride. 3.3.2.2 Permethylation. 3.3.2.3 Reference Permethyl Ethers. 3.3.2.4 High Performance Liquid Chromatography. 3.3.2.5 Centrifugally Accelerated Thin Layer Chromatography. 3.3.2.6 Autofluorescence. 3.3.2. 7 Mass Spectroscopy. 3.3.2.8 Nuclear Magnetic Resonance Spectroscopy. 3.3.3 Determination of Methylation Patterns. 3.3.3.1 Partial Demethylation. 3.3.3.2 UV-Spectroscopy. 4. DISTRIBUTION OF BIFLAVONOIDS IN THE CUPRESSACEAE. 4.1 Reliability of Biflavonoid Pattern within Species. 4.2 Definition of Character-states. 4.3 Biflavonoid Patterns. 5. CHEMOTAXONOMY. 5.1 Polarity of chemical characters. 5.2 Correlation with existing generic boundaries. 5.3 Biflavonoid Patterns in relation to Taxonomy above the Generic Level. 6. OTHER DATA SOURCES. 6.1 Introduction. 6.2 Leaf characters. 6.3 Cone morphology. 6.4 Reproductive Biology. 6.5 Wood Histology. 6.6 Chemistry 6.6.1 Tropolones. 6.6.2 Terpenes. 6.6.3 Flavonoids. 6.7 Pollen Morphology. 7. CONCLUSIONS. 8. LOCALISATION OF BIFLAVONOIDS IN LEAVES. 8.1 Introduction. 8.2 Materials and Methods. 8.2.1 Leaf Anatomy 8.2.2 Fluorescence Microscopy. 8.2.3 Extraction of Biflavonoids. 8.3 Results. 8.3.1 Leaf anatomy of Agathis robusta. 8.3.2 Fluorescence Microscopy. 8.3.2.1 Autofluorescence. 8.3.2.2 Aluminium Chloride Induced Fluorescence. 8.3.3 Chromatography of Extracts. 8.3.4 Survey of Other Taxa. 8.4 Discussion. REFERENCES. APPENDIX. PUBLICATIONS. TABLES. 1. Examples of Taxonomic Groupings ••••••••••••••••••••••••••• Section 1. 2. Occurrence of Biflavonoids in the Coniferales ••••••••.••••••••••. 2.2 3. Distribution of Biflavonoids in the Cupressaceae ••••••••••••••••• 2.3 4. Chromatographic Characteristics and Sources of Reference Samples of Parental Compounds and their Partial Methyl Ethers •••••....••••.•..•••••.••••••••.....•••••. 3.2.1 5. HPLC of Methyl Ethers of Amentoflavone and Hinokiflavone using a Diol column .•••.••••...•.•.••..••••.••••• 3.2.2 6. Chromatographic and Spectral Characteristics of Permethy 1 Ethers. • . • . 3. 3. 2. 3 7. HPLC of Permethyl Ethers using Reverse Phase (C1s) and Normal Phase (silica) columns .•••.•••••.••••••••••••••••••• 3.3.2.4 8. Chemical Shifts of Protons in Cupressuflavone HexaJDethy 1 Ether. • . • . • . • . • . • • . • • . • . • . • • . • 3. 3. 2. 8 9. Reliability of Biflavonoid Pattern ••.•.•••••••••••••••••••••••••• 4.1 10. Biflavonoid Derivatives Detected in Leaf Extracts ••••••••••••••• 4.3 11. Biflavonoid Permethyl Ethers Detected in the Permethylated Raw Leaf Extracts •.•••••..•••..••••••••••••••••• 4.3 12. Generic Groupings suggested by Biflavones ••••••••••••••.••••.••• 5.3 13. Distribution of Character-states of Other Data Sources •••••••••• 6.2 14. Results Obtained from two-dimensional Paper Chromatography of extracts of Agathis robusta leaves •••••••••• 8.3.3 15. Occurrence of Biflavonoid Permethyl Ethers in the Permethylated Raw Extracts of Agathis robusta leaves ••••...... 8.3.3 FIGURES. 1. Examples of the Different Interflavonyl Linkages of Biflavonoids ......................................... 2.1 2. Biosynthetic Pathways of Biflavonoids •••••••....•••••••••••••••••• 2.1 3. HPLC trace of the Permethylated Raw Extract of Cal ocedrus decurrens. 3. 3. 2. 4 4. H-NMR trace of Cupressuflavone Hexamethyl Ether •••••.••••••••••••• 3.3.2.8 5. Products from Partial Demethylation ••••••••••••••••••.•.••••••.••• 3.3.3.l 6. UV spectral data of Cupressuflavone 77" dimethyl ether •••••••••••• 3.3.3.2 7. UV spectral data of Amentoflavone 7"4"' dimethyl ether •••••••••••• 3.3.3.2 8a. Leaf margin of Agathis robusta as seen in transverse sect ion. 8. 3. 1 8b. Diagram illustrating the epidermal and hypodermal wall systems of the adaxial surface of the leaf of Agathis robusta ................................................ B. 3.1 9-14 Light microscopy of the adaxial region of Agathis robusta leaves in transverse section •.•••••••••...••••• 8.3.l 15-20 Fluorescence microscopy of fresh transections or. epidermal peels from the adaxial surface of Agathis robusta leaves •••••••••.••.••••••....••••••...••.•.•• 8. 3. 2 21-28 Fluorescence microscopy of fresh sections of leaves of other taxa. 8. 3. 4 29-34 Colour photographs of induced fluorescence ••••.•••••••••••.••.. 8.3.4 TABLE 1. EXAMPLES OF TRIBAL AND SUBFAMILY GROUPINGS. ENDLICHBR (1847) SAXTON ( 1913a) Pll,CllR (1926) *>SELEY (1943) Junip@r inee Juniperua CupreHoideae f'buja Juniperoideae Pil1er Arceutboa Juniperoideae Juniperua Libocedl"UII Juaiperw Arceutbos • Cuprea•ineae Cupre••us JuniperU11 ( = Juniperus in part) Cha.aecyparis ~tr11clinia Cuprea•oide- Pil1er CupruaU11 /llicrobiota t Cupre11aus * C-"-ecyparia Thuiopeideae Biota Biota * Cuprea•oideae Cupressus (• Platyclatlin) (; Platycladus) Tbujoicleae Pil1er Actinoatrobua l'ha.recyparis Thuja Cha.aecyparis * Cal]itria 1'hujopais rhujopai!I • Tetraclinis Thujoideae Libocedrus Cellitro,wis Biota Actinoatrobeae Nfr/ddn1to11111 Callitroideae liiddrin,tonia ( = NeocallUropais) ("' Platycl11dus) Frenela ActinOlltrobus liiddrin,toni11 Tetraclinis (- Callitri• in part) Callitri!I
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