Thạc Sĩ Thành phần hóa học của cây lá xuân hoa mạng pseuderanthemum reticulatum radlk họ ô rô (acanthaceae)

ĐẠI HỌC KHOA HỌC TỰ NHIÊN
LUẬN VĂN THẠC SĨ KHOA HỌC HÓA HỌc
2011

TABLE OF CONTENTS

ABSTRACT i
ACKNOWLEDGEMENTS iii
TABLE OF CONTENTS iv
LIST OF ABBREVIATIONS vi
LIST OF TABLES viii
LIST OF FIGURES AND SCHEMES ix

Chapter 1: LITERATURE REVIEW & AIM OF STUDY 1
1.1. General information of Pseuderanthemum 1
1.1.1. Generic description 1
1.1.1.1. P. acuminatissimum (Miq.) Kuntze. 1
1.1.1.2. P. bracteatum Imlay. 4
1.1.1.3. P. carruthersii 4
1.1.1.3.1. P. carruthersii (Seem.) Guill. var. atropurpureum
(Bull.) Fosb. 4
1.1.1.3.2. P. carruthersii var. ovatifolium (Brem.) Brem. 4
1.1.1.4. P. palatiferum (Nees) Radlk. 4
1.1.1.5. P. reticulatum Radlk. 5
1.1.2. Pharmaceutical studies of Pseuderanthemum 5
1.1.2.1. In vitro assays 5
1.1.2.2. In vivo assays 6
1.1.3. Chemical studies of Pseuderanthemum 7
1.1.3.1. Eranthemum pulchellum 7
1.1.3.2. P. carruthersii atropurpureum 7
1.1.3.3. P. latifolim 8
1.1.3.4. P. palatiferum 8
1.2. Aim of study 11

Chapter 2: EXPERIMENTAL 12
2.1. Materials 12
2.2. Plant material 12
2.3. Extraction and isolation procedures 12
2.4. Analysis of fatty acid of two glycoglycerolipids 13
Chapter 3: RESULTS & DISCUSSION 16
3.1. Structure elucidation of compound RE-EA1 16
3.2. Structure elucidation of compound RE-EA3 16
3.3. Structure elucidation of compound RE-EA4 17
3.4. Structure elucidation of compound RE-EA6 18
3.5. Structure elucidation of two diastereomers RE-EA7 and RE-EA8,
which were isolated from RE-EA2 20
3.5.1. Structure elucidation of compound RE-EA7 21
3.5.2. Structure elucidation of compound RE-EA8 23
3.6. Structure elucidation of compound RE-Bu2 24
3.7. Structure elucidation of compound RE-Bu3 28
3.8. Structure elucidation of compound RE-Bu4 30
3.9. Structure elucidation of compound RE-PE1 34
3.10. Structure elucidation of compound RE-PE2 35
Chapter 4: CONCLUSION 40
LIST OF PUBLICATIONS 42
REFERENCES 43
APPENDICES


LIST OF TABLES

Table 1: The content of some major and trace minerals in the leaves of P. palatiferum
Table 2: The NMR data of RE-EA1 and comparison of its ones with those of tyrosol
Table 3: The NMR data of RE-EA3 and comparison of its ones with those of uracil
Table 4: The NMR data of RE-EA4 and comparison of its ones with those of stigmasterol, β-sitosterol and β-D-glucopyranose
Table 5: The NMR data of RE-EA6 22
Table 6: The NMR data of RE-EA8 and RE-EA7 and comparison of their ones with those of (6S,9S)-vomifoliol
Table 7: The comparison of 13C-NMR data of RE-EA7, RE-EA8 and the aglycon of RE-EA6 with those of the aglycons of four roseoside diastereomers 26
Table 8: The NMR data of RE-Bu2 and comparison of its ones with those of salidroside
Table 9: The NMR data of RE-Bu3 and comparison of its ones with those of uridine
Table 10: The NMR data of RE-Bu4 and comparison of its ones with those of apigenin 7-O-β-D-rutinoside Table 11: The NMR data of RE-PE1 and comparison of its ones with those of 1-linolenoyl-2-palmitoyl-3-galactosylglycerol
Table 12: The NMR data of RE-PE2 39


LIST OF FIGURES AND SCHEMES

Figure 1: Xuân Hoa Nhọn, P. acuminatissimum (Miq.) Kuntze 2
Figure 2: Xuân hoa lá-hoa, P. bracteatum Imlay. 2
Figure 3: Xuân hoa đỏ, P. carruthersii (Seem.) Guill. var. atropurpureum (Bull.) Fosb. 2
Figure 4: Nấp vũm, P. carruthersii var. ovatifolium (Brem) Brem. 2
Figure 5: P. crenulatum (Lindl.) R. Ben. 2
Figure 6: P. eberhardtii R. Ben. 2
Figure 7: Xuân hoa, P. palatiferum (Nees) Radlk. 2
Figure 8: P. poilanei R. Ben.Z 2
Figure 9: Xuân hoa mạng, P. reticulatum Radlk. 3
Figure 10: P. tonkinense R. Ben. 3
Figure 11: Eranthemum pulchellum 3
Figure 12: P. alatum 3
Figure 13: P. laxiflorum 3
Figure 14: P. sinuatum. 3
Figure 15: P. tuberculatum (Hook. f.) Radlk 3
Figure 16 P. variabile 3
Figure 17: The HMBC correlations of RE-EA6 19
Figure 18: The HMBC correlations of Re-Bu3 27
Figure 19: The HMBC correlations of RE-Bu4 30
Figure 20: The HMBC correlations of RE-PE1 35
Figure 21: The HMBC correlations of RE-PE2 37


Chapter 1

LITERATURE REVIEW & AIM OF STUDY


1.1. General information of Pseuderanthemum
Pseuderanthemum or Eranthemum[1] is a member of Acanthaceae. The genus contains about 196 species, including perennial shurbs or herbs. The characteristics of the genus are beautiful flowers and foliage, high humidity need, flowering in spring and summer.
In Vietnam, Pseuderanthemum has nine species and two varieties[1] including P.

acuminatissimum (Miq.) Kuntze. (figure 1), P. bracteatum Imlay. (figure 2), P. carruthersii (Seem.) Guill. var. atropurpureum (Bull.) Fosb. (figure 3), P. carruthersii var. ovatifolium (Brem.) (figure 4), P. crenulatum (Lindl.) R. Ben (figure 5), P. eberhardtii R. Ben (figure 6), P. palatiferum (Nees) Radlk (figure 7), P. poilanei R. Ben.Z (figure 8), P. reticulatum Radlk (figure 9) and P. tonkinense R. Ben (figure 10).
In addition, we collected pictures of some species of Pseuderanthemum from internet such as Eranthemum pulchellum (figure 11)[32], P. alatum (figure 12)[33], P. laxiflorum (figure 13)[34], P. sinuatum (figure 14)[35], P. tuberculatum (Hook. f.) Radlk (hình 15)[36] and P. variabile (figure 16).[37]

1.1.1. Generic description
In this section, the botanic morphology of some Vietnamese Pseuderanthemumspecies was described.

1.1.1.1. P. acuminatissimum (Miq.) Kuntze.[1],[2]
Vietnamese name: Xuân hoa nhọn (figure 1).
Perennial shrub. Stems terete in older positions, glabrous and tetragonal in younger positions. Leaves 10-20 cm long, 5-9 cm wide; costa and lateral veins 6 pairs, petioles 4-5 cm long; peduncle 20 cm long. Flowers in cymes, bisexual, often zygomorphic; calyx 3.5 cm long, glabrous; corolla tube 3.5 cm long. Capsule 3.5 cm long, glabrous.
The herb, a species of Java Island (Indonesia), has been planted in Singapore and Vietnam (Bảo Lộc, Sài Gòn).