日本産植物フシグロSilene firma、クロタキカズラHosiea japonica およびベトナム産植物Heliciopsis terminalisの成分研究

概要

༤ኈㄽᩥ

᪥ᮏ⏘᳜≀ࣇࢩࢢࣟ Silene firmaࠊࢡࣟࢱ࢟
࢝ࢬࣛ Hosiea japonica ࠾ࡼࡧ࣋ࢺࢼ࣒⏘᳜
≀ Heliciopsis terminalis ࡢᡂศ◊✲

2020
ᗈᓥ኱Ꮫ኱Ꮫ㝔
་ṑ⸆ಖ೺Ꮫ◊✲⛉  ⸆Ꮫ⛉ᑓᨷ
⏕⸆Ꮫ◊✲ᐊ
ᖹᡂ 29 ᖺᗘධᏛ  NGUYEN HOANG UYEN
୺ᣦᑟᩍဨ

ᯇᾉ ຾⩏

┠ḟ
➨ 1 ❶ ᗎㄽ ·······················································································1
➨ 2 ❶ ᪥ᮏ⏘᳜≀ࣇࢩࢢࣟ Silene firma ࡢᡂศ◊✲ ····································2
➨ 1 ⠇ ᪥ᮏ⏘᳜≀ࣇࢩࢢࣟ Silene firma ࡟ࡘ࠸࡚ ·································2
➨ 2 ⠇ ᢳฟࠊศ㞳ཬࡧ⢭〇 ·····························································3
➨ 3 ⠇ ᪂つ໬ྜ≀࡟ࡘ࠸࡚ ·····························································5
➨ 1 㡯 ᪂つ໬ྜ≀ Compound 2 ࡢᵓ㐀Ỵᐃ ·····································5
➨ 2 㡯 ᪂つ໬ྜ≀ Compound 11 ࡢᵓ㐀Ỵᐃ ·································· 10
➨ 4 ⠇ ᪤▱໬ྜ≀࡟ࡘ࠸࡚ ··························································· 15
➨ 1 㡯 ᪤▱໬ྜ≀ Compound 1 ࡢᵓ㐀Ỵᐃ ··································· 16
➨ 2 㡯 ᪤▱໬ྜ≀ Compound 3 ࡢᵓ㐀Ỵᐃ ··································· 18
➨ 3 㡯 ᪤▱໬ྜ≀ Compound 4 ࡢᵓ㐀Ỵᐃ ··································· 19
➨ 4 㡯 ᪤▱໬ྜ≀ Compound 5 ࡢᵓ㐀Ỵᐃ ··································· 21
➨ 5 㡯 ᪤▱໬ྜ≀ Compound 6 ࡢᵓ㐀Ỵᐃ ··································· 23
➨ 6 㡯 ᪤▱໬ྜ≀ Compound 7 ࡢᵓ㐀Ỵᐃ ··································· 25
➨ 7 㡯 ᪤▱໬ྜ≀ Compound 8 ࡢᵓ㐀Ỵᐃ ··································· 27
➨ 8 㡯 ᪤▱໬ྜ≀ Compound 9 ࡢᵓ㐀Ỵᐃ ··································· 29
➨ 9 㡯 ᪤▱໬ྜ≀ Compound 10 ࡢᵓ㐀Ỵᐃ ·································· 31
➨ 10 㡯 ᪤▱໬ྜ≀ Compound 12 ࡢᵓ㐀Ỵᐃ ·································· 33
➨ 11 㡯 ᪤▱໬ྜ≀ Compound 13 ࡢᵓ㐀Ỵᐃ ·································· 35
➨ 12 㡯 ᪤▱໬ྜ≀ Compound 14 ࡢᵓ㐀Ỵᐃ ·································· 37
➨ 13 㡯 ᪤▱໬ྜ≀ Compound 15 ࡢᵓ㐀Ỵᐃ ·································· 39
➨ 14 㡯 ᪤▱໬ྜ≀ Compound 16 ࡢᵓ㐀Ỵᐃ ·································· 40
➨ 15 㡯 ᪤▱໬ྜ≀ Compound 17 ࡢᵓ㐀Ỵᐃ ·································· 42
➨ 16 㡯 ᪤▱໬ྜ≀ Compound 18 ࡢᵓ㐀Ỵᐃ ·································· 44
➨ 17 㡯 ᪤▱໬ྜ≀ Compound 19 ࡢᵓ㐀Ỵᐃ ·································· 45
➨ 18 㡯 ᪤▱໬ྜ≀ Compound 20 ࡢᵓ㐀Ỵᐃ ·································· 47
➨ 3 ❶ ᪥ᮏ⏘᳜≀ࢡࣟࢱ࢟࢝ࢬࣛ Hosiea japonica ࡢᡂศ◊✲ ···················· 49
➨ 1 ⠇ ᪥ᮏ⏘᳜≀ࢡࣟࢱ࢟࢝ࢬࣛ Hosiea japonica ࡟ࡘ࠸࡚ ················· 49
➨ 2 ⠇ ᢳฟࠊศ㞳ཬࡧ⢭〇 ··························································· 50
➨ 3 ⠇ ᪂つ໬ྜ≀࡟ࡘ࠸࡚ ··························································· 52
➨ 1 㡯 ᪂つ໬ྜ≀ Compound 21 ࡢᵓ㐀Ỵᐃ ·································· 52

➨ 2 㡯 ᪂つ໬ྜ≀ Compound 22 ࡢᵓ㐀Ỵᐃ ·································· 57
➨ 4 ⠇ ᪤▱໬ྜ≀࡟ࡘ࠸࡚ ··························································· 61
➨ 1 㡯 ᪤▱໬ྜ≀ Compound 23 ࡢᵓ㐀Ỵᐃ ·································· 62
➨ 2 㡯 ᪤▱໬ྜ≀ Compound 24 ࡢᵓ㐀Ỵᐃ ·································· 64
➨ 3 㡯 ᪤▱໬ྜ≀ Compound 25 ࡢᵓ㐀Ỵᐃ ·································· 66
➨ 4 㡯 ᪤▱໬ྜ≀ Compound 26 ࡢᵓ㐀Ỵᐃ ·································· 68
➨ 5 㡯 ᪤▱໬ྜ≀ Compound 27 ࡢᵓ㐀Ỵᐃ ·································· 70
➨ 6 㡯 ᪤▱໬ྜ≀ Compound 28 ࡢᵓ㐀Ỵᐃ ·································· 72
➨ 7 㡯 ᪤▱໬ྜ≀ Compound 29 ࡢᵓ㐀Ỵᐃ ·································· 74
➨ 8 㡯 ᪤▱໬ྜ≀ Compound 30 ࡢᵓ㐀Ỵᐃ ·································· 76
➨ 9 㡯 ᪤▱໬ྜ≀ Compound 31 ࡢᵓ㐀Ỵᐃ ·································· 78
➨ 10 㡯 ᪤▱໬ྜ≀ Compound 32 ࡢᵓ㐀Ỵᐃ ·································· 80
➨ 11 㡯 ᪤▱໬ྜ≀ Compound 33 ࡢᵓ㐀Ỵᐃ ·································· 82
➨ 12 㡯 ᪤▱໬ྜ≀ Compound 34 ࡢᵓ㐀Ỵᐃ ·································· 84
➨ 13 㡯 ᪤▱໬ྜ≀ Compound 35 ࡢᵓ㐀Ỵᐃ ·································· 86
➨ 14 㡯 ᪤▱໬ྜ≀ Compound 36 ࡢᵓ㐀Ỵᐃ ·································· 88
➨ 15 㡯 ᪤▱໬ྜ≀ Compound 37 ࡢᵓ㐀Ỵᐃ ·································· 90
➨ 16 㡯 ᪤▱໬ྜ≀ Compound 38 ࡢᵓ㐀Ỵᐃ ·································· 92
➨ 17 㡯 ᪤▱໬ྜ≀ Compound 39 ࡢᵓ㐀Ỵᐃ ·································· 94
➨ 18 㡯 ᪤▱໬ྜ≀ Compound 40 ࡢᵓ㐀Ỵᐃ ·································· 96
➨ 19 㡯 ᪤▱໬ྜ≀ Compound 41 ࡢᵓ㐀Ỵᐃ ·································· 98
➨ 20 㡯 ᪤▱໬ྜ≀ Compound 42 ࡢᵓ㐀Ỵᐃ ································· 100
➨ 21 㡯 ᪤▱໬ྜ≀ Compound 43 ࡢᵓ㐀Ỵᐃ ································· 102
➨ 22 㡯 ᪤▱໬ྜ≀ Compound 44 ࡢᵓ㐀Ỵᐃ ································· 104
➨ 23 㡯 ᪤▱໬ྜ≀ Compound 45 ࡢᵓ㐀Ỵᐃ ································· 106
➨ 24 㡯 ᪤▱໬ྜ≀ Compound 46 ࡢᵓ㐀Ỵᐃ ································· 108
➨ 25 㡯 ᪤▱໬ྜ≀ Compound 47 ࡢᵓ㐀Ỵᐃ ································· 110
➨ 26 㡯 ᪤▱໬ྜ≀ Compound 48 ࡢᵓ㐀Ỵᐃ ································· 112
➨ 27 㡯 ᪤▱໬ྜ≀ Compound 49 ࡢᵓ㐀Ỵᐃ ································· 114
➨ 28 㡯 ᪤▱໬ྜ≀ Compound 50 ࡢᵓ㐀Ỵᐃ ································· 116
➨ 29 㡯 ᪤▱໬ྜ≀ Compound 51 ࡢᵓ㐀Ỵᐃ ································· 118
➨ 30 㡯 ᪤▱໬ྜ≀ Compound 52 ࡢᵓ㐀Ỵᐃ ································· 120
➨ 31 㡯 ᪤▱໬ྜ≀ Compound 53 ࡢᵓ㐀Ỵᐃ ································· 122
➨ 32 㡯 ᪤▱໬ྜ≀ Compound 54 ࡢᵓ㐀Ỵᐃ ································· 124
➨ 4 ❶ ࣋ࢺࢼ࣒⏘᳜≀ Heliciopsis terminalis ࡢᡂศ◊✲
➨ 1 ⠇ ࣋ࢺࢼ࣒⏘᳜≀ Heliciopsis terminalis ࡟ࡘ࠸࡚························· 126

➨ 2 ⠇ ᢳฟࠊศ㞳ཬࡧ⢭〇 ·························································· 127
➨ 3 ⠇ ᪂つ໬ྜ≀࡟ࡘ࠸࡚ ·························································· 129
➨ 1 㡯 ᪂つ໬ྜ≀ Compound 55 ࡢᵓ㐀Ỵᐃ ································· 129
➨ 2 㡯 ᪂つ໬ྜ≀ Compound 56 ࡢᵓ㐀Ỵᐃ ································· 132
➨ 2 㡯 ᪂つ໬ྜ≀ Compound 57 ࡢᵓ㐀Ỵᐃ ································· 136
➨ 4 ⠇ ᪤▱໬ྜ≀࡟ࡘ࠸࡚ ·························································· 140
➨ 1 㡯 ᪤▱໬ྜ≀ Compound 58 ࡢᵓ㐀Ỵᐃ ································· 141
➨ 2 㡯 ᪤▱໬ྜ≀ Compound 59 ࡢᵓ㐀Ỵᐃ ································· 143
➨ 3 㡯 ᪤▱໬ྜ≀ Compound 60 ࡢᵓ㐀Ỵᐃ ································· 145
➨ 4 㡯 ᪤▱໬ྜ≀ Compound 61 ࡢᵓ㐀Ỵᐃ ································· 147
➨ 5 㡯 ᪤▱໬ྜ≀ Compound 62 ࡢᵓ㐀Ỵᐃ ································· 149
➨ 6 㡯 ᪤▱໬ྜ≀ Compound 63 ࡢᵓ㐀Ỵᐃ ································· 151
➨ 7 㡯 ᪤▱໬ྜ≀ Compound 64 ࡢᵓ㐀Ỵᐃ ································· 153
➨ 8 㡯 ᪤▱໬ྜ≀ Compound 65 ࡢᵓ㐀Ỵᐃ ································· 155
➨ 9 㡯 ᪤▱໬ྜ≀ Compound 66 ࡢᵓ㐀Ỵᐃ ································· 157
➨ 10 㡯 ᪤▱໬ྜ≀ Compound 67 ࡢᵓ㐀Ỵᐃ ································· 159
➨ 11 㡯 ᪤▱໬ྜ≀ Compound 68 ࡢᵓ㐀Ỵᐃ ································· 161
➨ 12 㡯 ᪤▱໬ྜ≀ Compound 69 ࡢᵓ㐀Ỵᐃ ································· 163
➨ 13 㡯 ᪤▱໬ྜ≀ Compound 70 ࡢᵓ㐀Ỵᐃ ································· 165
➨ 5 ❶ DPPH ࣛࢪ࢝ࣝ㝖ཤάᛶヨ㦂 ···················································· 166
➨ 1 ⠇ DPPH ࣛࢪ࢝ࣝ㝖ཤάᛶヨ㦂࡟ࡘ࠸࡚ ······································· 166
➨ 2 ⠇ DPPH ࣛࢪ࢝ࣝ㝖ཤάᛶヨ㦂ἲ ················································ 167
➨ 3 ⠇ DPPH ࣛࢪ࢝ࣝ㝖ཤάᛶヨ㦂ࡢ⤖ᯝ ·········································· 168
➨ 6 ❶ Tyrosinase 㜼ᐖάᛶヨ㦂 ··························································· 169
➨ 1 ⠇ Tyrosinase 㜼ᐖάᛶヨ㦂࡟ࡘ࠸࡚ ············································· 169
➨ 2 ⠇ Tyrosinase 㜼ᐖάᛶヨ㦂ἲ ······················································ 170
➨ 3 ⠇ Tyrosinase 㜼ᐖάᛶヨ㦂ࡢ⤖ᯝ ················································ 171
➨ 7 ❶ α-Amylase 㜼ᐖάᛶヨ㦂··························································· 172
➨ 1 ⠇ α-Amylase 㜼ᐖάᛶヨ㦂࡟ࡘ࠸࡚ ············································· 172
➨ 2 ⠇ α-Amylase 㜼ᐖάᛶヨ㦂ἲ ······················································ 173
➨ 3 ⠇ α-Amylase 㜼ᐖάᛶヨࡢ⤖ᯝ ··················································· 174
➨ 8 ❶ A549 ⒴⣽⬊ቑṪᢚไάᛶヨ㦂 ·················································· 175
➨ 1 ⠇ A549 ⒴⣽⬊ቑṪᢚไάᛶヨ㦂࡟ࡘ࠸࡚ ····································· 175
➨ 2 ⠇ A549 ⒴⣽⬊ቑṪᢚไάᛶヨ㦂ἲ ·············································· 176

➨ 3 ⠇ A549 ⒴⣽⬊ቑṪᢚไάᛶヨ㦂ࡢ⤖ᯝ ········································ 177
➨ 9 ❶ ࡲ࡜ࡵ ················································································· 178
➨ 10 ❶ ᐇ㦂ࡢ㒊 ·············································································· 183
ཧ⪃ᩥ⊩ ·························································································· 194
ㅰ㎡ ································································································ 200

ᮏᩥ୰࡛౑⏝ࡋࡓ୺࡞␎ྕ
㸯

H NMR: Proton Nuclear Magnetic Resonance

13

C NMR: Carbon-13 Nuclear Magnetic Resonance

HR-ESI-MS: High Resolution Electro Spray Ionization Mass Spectroscopy
COSY: HH-Correlation Spectroscopy
HMBC: Heteronuclear Multiple Bond Connectivity
HSQC: Heteronuclear Single Quantum Coherence
IR: Infrared Spectroscopy
UV: Ultraviolet Spectroscopy
HPLC: High-Performance Liquid Chromatography
CC: Column Chromatography
TLC: Thin Layer Chromatography
ODS: Octadecylsilanized Silica gel
Cpd: Compound
fr.: fraction
br.: broad
s: singlet
d: doublet
t: triplet
q: quartet
m: multiplet

➨ 1 ❶ ᗎㄽ

௒᪥ࡲ࡛ே㢮ࡣࠊ᳜≀ࡸື≀ࠊ㖔≀➼ࡢᵝࠎ࡞ኳ↛≀ࢆᕦࡳ࡟฼⏝ࡋࠊ⸆⏝㈨※࡜ࡋ
࡚⏝࠸࡚ࡁࡓࠋኳ↛≀ࡣࠊᡃࠎ࡟ࡣ᝿ീࡶࡘ࠿࡞࠸ࡼ࠺࡞ᵓ㐀ࡸ⸆⌮స⏝ࢆᣢࡘྍ⬟ᛶࢆ
⛎ࡵ࡚࠾ࡾࠊ⌧ᅾ⮫ᗋ࡛౑⏝ࡉࢀ࡚࠸ࡿ་⸆ရࡢ᭷ຠᡂศ࡟ࡶࠊኳ↛࠿ࡽ༢㞳ࡉࢀࡓࡶࡢࠊ
࠶ࡿ࠸ࡣࡑࢀࡽࢆ࣮ࣜࢻ໬ྜ≀࡜ࡋ࡚ྜᡂࡉࢀࡓࡶࡢࡀᑡ࡞ࡃ࡞࠸ࠋ་⸆ရ࡟㝈ࡽࡎࠊ໬
⢝ရࡸ㤶ᩱࠊ೺ᗣ㣗ရ࡞࡝ኳ↛≀ࡣᖜᗈࡃ฼⏝ࡉࢀ࡚࠾ࡾࠊᡃࠎࡢ⏕ά࡟ᐤ୚ࡋ࡚࠸ࡿࠋ
ࡑࡢࡓࡵ᪂ࡋ࠸᭷⏝㈨※ࢆ᥈⣴ࡋࠊᮍ฼⏝᳜≀ࡢᡂศ◊✲ࠊ⏕≀άᛶ࡟ࡘ࠸᳨࡚ウࢆ⾜࠺
ࡇ࡜ࡣ㔜せ࡛࠶ࡿࠋ
᪥ᮏ⏘᳜≀ࣇࢩࢢࣟ Silene firmaࠊࢡࣟࢱ࢟࢝ࢬࣛ Hosiea japonica ࠾ࡼࡧ࣋ࢺࢼ࣒⏘᳜
≀ Heliciopsis terminalis ࡟㛵ࡍࡿ໬Ꮫⓗ◊✲ࡢሗ࿌౛ࡣ࡯࡜ࢇ࡝࡞ࡃࠊࡑࡢྵ᭷ᡂศࡢ໬Ꮫ
ᵓ㐀࠾ࡼࡧ⏕≀άᛶ࡟⯆࿡ࡀᣢࡓࢀࡓࡓࡵࠊࡇࢀࡽࡢ᳜≀ࡢᡂศ◊✲ࢆ⾜࠺ࡇ࡜࡜ࡋࡓࠋ

1

➨ 2 ❶ ᪥ᮏ⏘᳜≀ࣇࢩࢢࣟ Silene firma ࡢᡂศ◊✲
➨ 1 ⠇ ᪥ᮏ⏘᳜≀ࣇࢩࢢࣟ Silene firma ࡟ࡘ࠸࡚
Ꮫྡ㸸Silene firma Sieb. Et Zucc.
࿴ྡ㸸ࣇࢩࢢࣟ
⛉ྡ㸸Caryophyllaceae (ࢼࢹࢩࢥ⛉)
ᒓྡ㸸Silene (࣐ࣥࢸ࣐ᒓ)
ศᕸ㸸ᮏᕞࠊᅄᅜࠊ஑ᕞࠊᮅ㩭ࠊ୰ᅜࠊࣟࢩ࢔
ⰼᮇ㸸6㹼9 ᭶
ⲡ୔㸸50㹼100 cm
≉ᚩ㸸 ⱼࡣ┤❧ࡋࠊẟࡀᐦ⏕ࡍࡿࠋⴥࡣᑐ⏕ࡋࠊ㛗ࡉ 4㹼10 cmࠊᖜ 0.8㹼2.5 cm ࡢᢨ㔪ᙧ
㹼㛗ᴃ෇ᙧࠊ⦕ẟࡀ࠶ࡾࠊඛࡀᑤࡿࠋⱖࡣ⊃ᢨ㔪ᙧࠋⱼ㡬ࡸⴥ⭆࡟ⓑⰍ㹼ࣆࣥࢡ
ࡢᑠࡉ࡞ⰼࢆࡘࡅࡿࠋⰼ᯶ࡣ㛗ࡉ 5㹼20 mmࠋⰼᘚࡣ㛗ࡉ 2㹼3 mm ࡜ᑠࡉࡃࠊඛࡀ
2 ⿣ࡍࡿࠋ㞝ࡋ࡭ 10 ಶࠋⰼᰕ 3 ಶࠋⴟࡣ㛗ࡉ 7㹼10 mm ࡢ༸ᙧࠊඛࡀὸࡃ 5 ⿣ࡋ(5
ṑ)ࠊ10 ⬦ࡀ࠶ࡾࠊᯝ᫬࡟ࡶṧࡗ࡚㛗ࡉ 10㹼12 mm ࡜ࡸࡸ኱ࡁࡃ࡞ࡿࠋᯝᐇࡣ㛗ࡉ
8㹼11 mmࠊ⇍ࡍ࡜ඛࡀⰼᰕࡢ 2 ಸᩘࡢ 6 ಶ࡟⿣㛤ࡍࡿࠋ✀Ꮚࡣ⅊〓Ⰽࠊ㛗ࡉ⣙ 1
mmࠋ1)
ᮏ᳜≀ⴥ㒊ࠊⱼ㒊࠿ࡽࡣࠊࡇࢀࡲ࡛࡟ࣇࣛ࣎ࣀ࢖ࢻࡸࢧ࣏ࢽࣥ࡞࡝ࡀ༢㞳ࡉࢀ࡚
࠸ࡿࠋ2)

Picture: http://www.okadanouen.com/zukan/fusiguro/fusiguro23.8.13-1.jpg

2

➨ 2 ⠇ ᢳฟࠊศ㞳࠾ࡼࡧ⢭〇
ࣇࢩࢢࣟࡢᆅୖ㒊 10.6 kg ࢆ࣓ࢱࣀ࣮࡛ࣝᢳฟࡋࠊᖖἲ࡟ᚑ࠸ࠊn-࣊࢟ࢧࣥࠊ㓑㓟࢚ࢳ
ࣝࠊ1-ࣈࢱࣀ࣮ࣝࠊỈ࡛㡰ḟศ㓄ࡋࡓࠋᚓࡽࢀࡓ n-࣊࢟ࢧࣥྍ⁐⏬ศ࡜㓑㓟࢚ࢳࣝྍ⁐⏬
ศ (164.8g) ࢆ㡰┦ࠊ㏫┦ࢩࣜ࢝ࢤ࣒ࣝ࢝ࣛࢡ࣐ࣟࢺࢢࣛࣇ࢕࣮ࠊODS-HPLC ࡟ࡼࡾศ㞳ࠊ
⢭〇ࡋࠊ20 ✀㢮ࡢ໬ྜ≀ࢆ༢㞳ࡋࡓࠋࡑࡢ࠺ࡕ compound 2, 11 ࡣ᪂つ໬ྜ≀ࠊcompound 1,
3-10, 12-20 ࡣ ᪤▱໬ྜ≀࡜ྠᐃࡋࡓࠋ

 

     Dried aerial parts of Silene firma
(10.6 kg)
Extracted with MeOH
Concentrated
Partitioned with n-Hexane, EtOAc, 1-BuOH

n-Hexane layer

1-BuOH layer
(76.0 g)

EtOAc layer

(164.8 g)

3

Aq. ...

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