VIETNAM NATIONAL UNIVERSITY - HO CHI MINH CITY UNIVERSITY OF SCIENCE  ĐỖ THỊ MỸ LIÊN STUDY ON CHEMICAL CONSTITUENTS AND BIOLOGICAL ACTIVITIES OF SOME PLANTS OF BOERHAAVIA GENUS (NYCTAGINACEAE) Subject: Organic chemistry Code number: 62 44 27 01 The first reviewer: Assoc Prof Trần Hùng The second reviewer: Assoc Prof Phạm Đình Hùng The third reviewer: Assoc Prof Trần Công Luận The first independent reviewer: Assoc Prof Nguyễn Thị Hoàng Anh The second independent reviewer: Dr Nguyễn Lê Bảo Khánh SUPERVISORS: PROF NGUYỄN KIM PHI PHỤNG PROF DOMINIQUE GUILLAUME Ho Chi Minh City, 2014 TABLE OF CONTENTS ACKNOWLEDGEMENTS i TABLE OF CONTENTS iii LIST OF ABBREVIATIONS v LIST OF TABLES vii LIST OF FIGURES AND SCHEMES ix Chapter 1: LITERATURE REVIEW 1.1 Boerhaavia genus – Generic description 1.1.1 Boerhaavia coccinea M 1.1.2 Boerhaavia diffusa L 1.1.3 Boerhaavia erecta L 1.1.4 Boerhaavia repens L 1.2 Boerhaavia genus- Pharmacological studies 1.2.1 Boerhaavia coccinea M 1.2.2 Boerhaavia diffusa L 1.2.3 Boerhaavia erecta L 1.3 Boerhaavia genus- Chemical studies 1.3.1 Boerhaavia coccinea M 1.3.2 Boerhaavia diffusa L 1.3.3 Boerhaavia erecta L 10 1.3.4 Boerhaavia repens L 10 1.4 Aim of the study 15 Chapter 2: EXPERIMENTAL 16 2.1 Instrumental material 16 2.2 Plant material 19 2.3 Extraction and isolation procedures 21 iii 2.4 Biological assays 25 Chapter 3: RESULTS & DISCUSSION 3.1 Chemical structure elucidation 31 3.1.1 Chemical structure of 12a-hydroxyrotenoids 31 3.1.2 Chemical structure of dehydrorotenoids 41 3.1.3 Chemical structure of coumaronochromonoids 59 3.1.4 Chemical structure of flavonoids 68 3.1.5 Chemical structure of nitrogen compounds 78 3.1.6 Chemical structure of phenolic compounds 83 3.1.7 Chemical structure of steroids and terpenoids 101 3.1.8 Chemical structure of other compounds 110 3.2 Biological activities of extracts and isolated compounds 117 Chapter 4: CONCLUSION 121 LIST OF PUBLICATIONS 127 REFERENCES 128 APPENDICES iv LIST OF ABBREVIATIONS 1D/2D-NMR : One/Two Dimensional – Nuclear Magnetic Resonance AchE : Acetylcholinesterase B : Boerhaavia brd : Broad doublet brs : Broad singlet Bu : n-Butanol C : Chloroform calcd : calculated CC : Silica gel Column Chromatography CD : Circular Dichroism COSY : Correlated spectroscopy d : Doublet dd : Doublet of doublet ddd : Doublet of doublet of doublet DMSO : Dimethyl sulfoxide DEPT : Distortionless Enhancement by Polarization Transfer EA : Ethyl acetate H : n-Hexane HIV : Human Immunodeficiency Virus HMBC : Heteronuclear Multiple Bond Coherence HSQC : Heteronuclear Single Quantum Correlation HPLC : High Performance Liquid Chromatography HR-ESI-MS : High Resolution - Electrospray Ionization - Mass Spectrometry J : Coupling constant GC-MS : Gas Chromatography - Mass Spectrometry LC : Liquid Chromatography m : Multiplet m/z : Mass to charge ratio M : Methanol Me : Methyl NMR : Nuclear Magnetic Resonance PE : Petroleum ether ppm : Part per million p-TLC : preparative Thin Layer Chromatography Rf : Retardation factors RP – C18 : Reverse Phase silica gel C18 s : Singlet TLC : Thin-Layer Chromatography t : Triplet UV : Ultraviolet [α]D : Specific rotation o : Degree Celcius C vi LIST OF TABLES Table 3.1: H–NMR spectroscopic data of the known compounds 11, 21 and the new compounds 54, 55, 56 Table 3.2: 13 C–NMR spectroscopic data of the known compounds 11, 21 and the new compounds 54, 55, 56 Table 3.3: 13 13 13 65 C–NMR spectroscopic data of the known compounds 62, 18 and the new compounds 63, 64 Table 3.9: 66 H–NMR spectroscopic data of the known compounds 65, 39, 36, 67 and 31 Table 3.10: 69 H–NMR spectroscopic data of the known compounds 62, 36, 33 and 58 Table 3.11: 58 H–NMR spectroscopic data of the known compounds 62, 18 and the new compounds 63, 64 Table 3.8: 57 C–NMR spectroscopic data of compounds 59, 60, 61 and the hydrolyzed aglycone of 60 Table 3.7: 45 H–NMR spectroscopic data of the new compounds 59, 60, 61 and the hydrolyzed aglycone of 60 Table 3.6: 44 C–NMR spectroscopic data of the known compounds 9, 10, 15, 16, 20 and the new compounds 57, 58 Table 3.5: 33 H–NMR spectroscopic data of the known compounds 9, 10, 15, 16, 20 and the new compounds 57, 58 Table 3.4: 32 13 70 C–NMR spectroscopic data of the known compounds 65, 39, 36, 67, 31, 62, 36, 33 and 68 Table 3.12: NMR spectroscopic data of the known compounds 69 and 70 Table 3.13: H and 13C–NMR data of the known compound 71 Table 3.14: 71 79 H–NMR spectroscopic data of the new compound 72, and the known compounds 73, 74, 75, 76, 77, 78, 79 Table 3.15: 13 82 91 C–NMR spectroscopic data of the new compound 72, and the known compounds 73, 74, 75, 76, 77, 78, 79 vii 92 Table 3.16: H–NMR spectroscopic data of the known compounds 80, 81, 47 and the new compound 82 Table 3.17: 13 98 C–NMR spectroscopic data of the known compounds 80, 81, 47 and the new compound 82 99 Table 3.18: NMR spectroscopic data of the known compounds 83, 103 Table 3.19: NMR spectroscopic data of the known compounds 84, 85 and the new compound 86 107 Table 3.20: H and 13C–NMR data of the known compound 87 108 Table 3.21: H–NMR spectroscopic data of the known compound 91 and the new compounds 88, 89, 90 Table 3.22: 13 113 C–NMR spectroscopic data of the known compound 91 and the new compounds 88, 89, 90 114 Table 3.23: NMR spectroscopic data of the known compounds 92 and 93 115 Table 3.24: Inhibitive activity of cytotoxic activity against three cancer cell lines of isolated compounds 118 Table 3.25: Acetylcholinesterase inhibition of some extracts and isolated compounds on acetylcholinesterase viii 119 LIST OF FIGURES AND SCHEMES Figure 1.1: Some species of Boerhaavia genus Figure 2.1: Green stem-leave Boerhaavia diffusa 17 Figure 2.2: Red-purple stem-leave Boerhaavia diffusa 17 Figure 2.3: Stem-leave Boerhaavia erecta 17 Figure 2.4: Comparison of TLC the four methanolic extracts of green stem-leave (GS), red-purple stem-leave (RS), green root (GR) and red-purple root (RR) of Boerhaavia diffusa Figure 2.5: HPLC chromatograms of (a) red-purple and (b) green B diffusa Figure 3.1 19 19 Comparison of CD and absorption spectra of compound 59 obtained by the calculations with the experiments 64 Scheme 1: Extraction and isolation procedure for Green Boerhaavia diffusa 27 Scheme 2: Extraction and isolation procedure for Red-purple Boerhaavia diffusa Scheme 3: 28 Extraction and isolation procedure for Boerhaavia erecta 29 ix CHAPTER 1: LITERATURE REVIEW Boerhaavia chinensis[w1] Boerhaavia coccinea[w2] Boerhaavia coulteria[w3] Boerhaavia diffusa[w4] Boerhaavia erecta[w5] Boerhaavia gracillima[w6] Boerhaavia herbstii[w7] Boerhaavia intermedia[w8] Boerhaavia linearifolia[w9] Boerhaavia purpurascens[w11] Boerhaavia repens[w12] Boerhaavia pterocarpa[w10] Boerhaavia scandens[w13] Boerhaavia triquetra[w15] Boerhaavia tetrendra[w14] Boerhaavia wrightii[w16] Figure 1.1 Some species of Boerhaavia genus 1.1 BOERHAAVIA GENUS – GENERIC DESCRIPTION Boerhaavia is a genus of 40 species, most of which are widely distributed in tropical and subtropical areas of the world.[19][69] Some of the species are treated as complex groups They are usually coastal plants spreading in sandy areas, gravelly plains, or on rocky slopes Owing to the polymorphism and the possible existence of hybrids between members of the complexes, many authors of regional floras have indicated that the distinctiveness at the species level, especially in the pantropical Boerhaavia diffusa complex and Boerhaavia repens complex, were rather difficult.[49][76][78] The genus Boerhaavia is characterized by elongate stems with prominent nodes, slender forking cymose or rarely racemose or spicate inflorescences with small, scale-like free bracts, small flowers with campanulate, cylindric, funnelshaped perianth limb separated by a constriction from the sulcate, enlarged lower Group C: Coumaronochromonoids Group D: Flavonoids 123 Group E: Nitrogen compounds Group F: Phenolic compounds 124 Group G: Steroids and terpenoids Group H: Other compounds BIOLOGICAL ACTIVITIES: Some extracts and some pure compounds were in vitro tested the inhibition against acetylcholineesterase and three cancer cell lines (MCF-7, NCI-H640 and Hela) The results showed that all the tested samples had no effect on acetylcholinesterase, whereas, some rotenoids (11, 21, 54, 58) showed significantly 125 activity against HeLa cell line (human epithelial carcinoma) and MCF-7 cell line (human breast cancer) This result was consistent to the published data which showed that the rotenoids from Boerhaavia genus exhibited antiproliferative effect against several lympho cell lines Future Outlook:  Studying the chemical constituents of the remaining extracts of three species  Testing the anticancer and some other inhibitory activities of isolated compounds 126 REFERENCES VIETNAMESE REFERENCES [1] Võ Văn Chi (1996) Tự điển thuốc Việt Nam NXB Y Học, Tp Hồ Chí Minh, 1029 – 1032 [2] Phạm Hoàng Hộ (2003) Cây cỏ Việt Nam- An illustrated flora of 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Hz, H-10) and 6.01 (s, H-6) The splitting of signals and coupling constants of protons at δH 8.28, 7.01 and 6.94 demonstrated two ortho-coupled protons of H–1, H–2 and H–3 of the A ring and the... Boerhaavia scandens[w13] Boerhaavia triquetra[w15] Boerhaavia tetrendra[w14] Boerhaavia wrightii[w16] Figure 1.1 Some species of Boerhaavia genus 1.1 BOERHAAVIA GENUS – GENERIC DESCRIPTION Boerhaavia