第一章 緒論
第四節 石斛之化學成分考察
依據文獻報導(5,29-105)，世界各地已完成的石斛屬植物之化學成分 研究，依其結構類別共分為 24 類，分別敘述如下：
(一) Phenanthrene
植物學名 化學成分 文獻
D. chryseum confusarin moscatin
29 30
D. chrysotoxum chrysotoxene confusarin
2,7-dihydroxy-3,4,6-trimethoxyphenanthrene
31 31 32
D. densiflorum 2,6-dihydroxy-1,5,7-trimethoxyphenanthrene moscatin
33 33
D. fimbriatum confusarin 34
D. loddigesii moscatin 35
D. moscatum moscatin 36
D. nakaharai bulbophyllanthrin confusarin
D. plicatile epheranthol B
3-hydroxy-2,4,7-trimethoxyphenanthrene nudol
plicatol A
plicatol B(moscatin)
37 38 38 39 39
D. rotundatum 2,7-dihydroxy-3,4,6-trimethoxyphenanthrene moscatin
nudol
40 40 40
D. sonia confusarin nudol
41 41
(二) Phenanthraquinones
植物學名 化學成分 文獻
D. densiflorum cypripedin densiflorol B
33 33
D. moniliforme denbinobin 42,43
D. nakaharai denbinobin nakaquinone
5 5
D. nobile denbinobin 44
D. sonia denbinobin 41
(三) Phenanthradiquinones
植物學名 化學成分 文獻
D. moniliforme moniliquinone 42
(四) Phenanthropyran
植物學名 化學成分 文獻
D. fimbriatum fimbriatone ( 2,7-dihydroxy-8-methoxy-5H-phenanthro [ 4,5-bcd ]pyran-5-one)
34
(五) 9,10-Dihydrophenanthrenes
植物學名 化學成分 文獻
D. chrysotoxum erianthridin
2,4,7-trihydroxy-9,10-dihydrophenanthrene
45 32
D. densiflorum lusianthridin 33
D. nobile lusianthridin
4,5-dihydroxy-3,7-dimethoxy -9,10-dihydrophenanthrene
44 46
D. plicatile 2,5-dihydroxy-4-methoxy -9,10-dihydrophenanthrene 3,7-dihydroxy-2,4-dimethoxy -9,10-dihydrophenanthrene erianthridin
7-hydroxy-2,3,4-trimethoxy -9,10-dihydrophenanthrene lusianthridin
plicatol C
38
D. rotundatum 2,7-dihydroxy-3,4,6-trimethoxy-9,10-dihydrophenanthrene rotundatin(plicatol C)
40 40
D. sonia lusianthridin 41
(六) 9,10-Dihydrophenanthraquinones
植物學名 化學成分 文獻
D. nakaharai nakaharaiquinone 5
D. plicatile ephemeranthoquinone 37
(七) 9,10-Dihydrophenanthropyrans
植物學名 化學成分 文獻
D. anoenum amoenumin(flaccidin) imbricatin
47 48
D. herbaceum imbricatin 48
D. pierardi flavidin 48
(八) Bidihydrophenanthrene
植物學名 化學成分 文獻
D. plicatile 2,2'-dimethoxy-4,4',7,7'-tetrahydroxy- 9,9',10,10'-tetrahydro-1,1'-biphenanthrene
37
(九) Bibenzyls
植物學名 化學成分 文獻
D. anoenum amoenylin batatasin-III
D. chrysanthum batatasin-III 48
D. chryseum chrysotobibenzyl chrysotoxin moscatilin
29 29 30
D. chrysotoxum chrysotobibenzyl chrysotoxine
D. crepidatum crepidatin 51
D. cumulatum cumulating tristin
52 52
D. densiflorum batatasin-III gigantol
D. fimbriatum chrysotobibenzyl chrysotoxine
D. graminifolium batatasin-III 48
D. herbaceum batatasin-III 48
D. lituiflorum batatasin-III 48
D. loddigesii dendrophenol (moscatilin) gigantol
55,35 56
D. moscatum moscatilin 57
D. nobile batatasin-III
4,5-dihydroxy-3,3'-dimethoxybibenzyl
D. plicatile batatasin
3-O-methylgigantol
37 37
3,3',5-trihydroxybibenzyl 38
D. rotundatum batatasin-III 40
D. sonia gigantol
3-O-methylgigantol
41 41
D. spathaceum batatasin-III 48
D. terminale batatasin-III 48
(十) Phenolic esters
植物學名 化學成分 文獻
D. chryseum defuscin
n-octacosyl trans-ferulate
30 30
D. chrysotoxum defuscin
n-octacosyl trans-ferulate
60 60
D. clavatum LINDL. var. aurantiacum
ferulic esters 61
D. fimbriatum n-alkyl cis-cinnamates(C24-32) n-alkyl trans-cinnamates(C24-32) defuscin
n-octacosyl ferulate
62 62 62 34
D. fuscescens defuscin 63
D. loddigesii n-docosyl trans-ferulate n-hexacosyl trans-ferulate n-octacosyl trans-cinnamate n-octacosyl trans-ferulate
64 64 64 64
D. moniliforme alkyl ferulate
alkyl 4'-hydroxy-cis-cinnamates alkyl 4'-hydroxy-trans-cinnamates
43 43 43
D. nakaharai alkyl ferulate
alkyl 4'-hydroxy-cis-cinnamates alkyl 4'-hydroxy-trans-cinnamates
5 5 5
(十一) Coumarins
植物學名 化學成分 文獻
D. chryseum coumarin 13
D. clavatum LINDL. var. aurantiacum
coumarin
p-hydroxycinnamates
61 61
D. densiflorum ayapin (6,7-methylenedioxycoumarin) psoralene
scopoletin
scopoletin methyl ether (scoparone)
65,33 66 65,33 65,33
D. farmerii aesculatin dimethyl ether (6,7-dimethoxycoumarin) ayapin (6,7-methylenedioxycoumarin)
67 67
D. fimbriatum ayapin (6,7-methylenedioxycoumarin) scopoletin methyl ether (scoparone)
34 34
D. thyrsiflorum ayapin (6,7-methylenedioxycoumarin) coumarin
6,7-dimethoxycoumarin
scopoletin (7-hydroxy-6-methoxycoumarin)
68
D. chrysotoxum chrysotoxone dendroflorin
D. densiflorum dendroflorin dengibsin
(十三) Alkaloid salts
植物學名 化學成分 文獻
D. anosmum octahydrodipyrido [1, 2-a: 1', 2'-c] imidazol-10-ium bromide
71
D. friedricksianum N-isopentenyldendroxinium chloride
N-isopentenyl-6-hydroxydendroxinium chloride
72
D. hildebrandii N-isopentenyldendroxinium chloride
N-isopentenyl-6-hydroxydendroxinium chloride
72
D. lohohense betaine 73-75
D. nobile dendrobine N-oxide
N-isopentenyldendrobinium bromide N-isopentenyldendroxinium chloride
N-isopentenyl-6-hydroxydendroxinium chloride N-methyldendrobinium iodide
76,77 76 76 76 76
D. parishii octahydrodipyrido [1, 2-a: 1', 2'-c] imidazol-10-ium bromide
71
D. pierardii betaine 75
D. wardianum dendrowardine 78
(十四) Dendrobine-type alkaloids
植物學名 化學成分 文獻
D. findlayanum dendrobine
2-hydroxydendrobine
79 79
D. friedricksianum dendramine 72
D. hildebrandii dendramine 80
D. moniliforme dendrobine 43
D. nobile dendramine (6-oxydendrobine) dendrine
D. Snowflake “Red Star”
(十五) Dendroxine-type alkaloids
植物學名 化學成分 文獻
D. nobile dendroxine
4-hydroxy-dendroxin 6-oxydendroxin
82 87 83
(十六) Indolizine alkaloids
植物學名 化學成分 文獻
D. chrysanthum hygrine 88
D. crepidatum crepidamine crepidine dendrocrepin
89 89 89
D. loddigesii monool shihunidine
64 55
D. primulinum dendroprimine hygrine
90 88
(十七) Nobiline-type alkaloids
植物學名 化學成分 文獻
D. findlayanum nobiline(nobilonine) 79
D. friedricksianum 6-hydroxynobiline nobiline(nobilonine)
72 72
D. hildebrandii 6-hydroxynobiline nobiline(nobilonine)
72 72
D. nobile nobilonine 91
(十八) Spirophthalides (phthalide- pyrrolidine alkaloids)
植物學名 化學成分 文獻
D. loddigesii shihunine 55
D. pierardii pierardine shihunine
75,92 75,92
(十九) Sesquiterpenes
植物學名 化學成分 文獻
D. aduncum aduncin(4-hydroxy-6-deoxydihydropicrotoxin) 93 D. anoenum amoenin
amotin
94 94
D. nobile nobilomethylene dendrobane A
87 58
D. Snowflake “Red Star”
flakinin A flakinin B
86 86
(二十) Steroids
植物學名 化學成分 文獻
D. chryseum ß-sitosterol 19
D. chrysotoxum ß-sitosterol 21
D. clavatum LINDL. var. aurantiacum
phytosterol (ß-sitosterol, stigmasterol, campesterol) stigmast-4-en-3-one
61 61
D. densiflorum ß-sitosterol 66
D. fimbriatum denfigenin diosgenin
D. gibsonii ß-sitosterol 70
D. loddigesii stigmast-4-en-3-one 64
D. moniliforme ergosterol
ergosterol peroxide
phytosterol (ß-sitosterol, stigmasterol, campesterol) stigmast-4-en-3-one
43 43 43 43
D. nakaharai phytosterol (ß-sitosterol, stigmasterol, campesterol) 5
D. superbum ß-sitosterol 96
(二十一) Flavonoid
植物學名 化學成分 文獻
D. densiflorum homoeriodictyol naringenin
33 33
D. nakaharai vitexin 5
(二十二) Glycosides
植物學名 化學成分 文獻
D. chryseum daucosterol 30
D. chrysotoxum daucosterol 45
D. densiflorum densifloroside
densifloroside[cis isomer]
97 97
D. fimbriatum daucosterol 54
D. nakaharai nakaharoside A nakaharoside B
5 5
D. nobile dendroside A dendroside B dendroside C dendroside D dendroside E dendroside F dendroside G dendronobilosides A dendronobilosides B dendronobilosides C dendronobilosides D dendronobilosides E
7998
D. ochreatum dendrosteroide epi-ochreasteroide ochreasteroide
100 100 101
D. Pompadour quercetin 3-glucoside quercetin 3-rutinoside quercetin 7-glucoside
quercetin 3-rutinoside-7-glucoside
kaempferol 3-rhamnosyl(1→6) galactoside kaempferol 3-rutinoside
kaempferol 7-glucoside
kaempferol 3-neohesperidoside-7-glucoside kaempferol 3-rutinoside-7-glucoside
quercetin 3-ferulylrutinoside-7-glucoside
102
(二十三) Acylated anthocyanins
植物學名 化學成分 文獻
D. Pompadour cyanidin 3-O-[6-O-(malonyl)-β-D-glucopyranoside]
-7,3'-O-di-[6-O-(trans-sinapyl)-
β-D-glucopyranoside]and its demalonyl derivative
102
D.‘Pramot’ cyanidin-3-O-[6-O-(malonyl)-β-D-glucopyranoside]
-7,3'-di-O-[6- O-(4-O-(β-D-glucopyranosyl)oxybenzoyl)-β-D-glucopyranoside]
cyanidin-3-O-[β-D-glucopyranoside]
-7,3'-di-O-[6-O-(4-O-(β-D-glucopyranosyl)oxybenzoyl)-β-D-glucopyranoside]
103
104
(二十四) Others
植物學名 化學成分 文獻
D. chryseum 2,4-dihydroxy-3,6-dimethyl methyl benzoate 2,6-dimethoxybenzoquinone
30 30
D. chrysotoxum protocatechuic acid（3,4-dihydroxy-benzoic acid） 32 D. clavatum LINDL.
var. aurantiacum
aliphatic alcohols 61
D. densiflorum oleanolic acid 66
D. farmerii p-hydroxyphenyl propionic acid 66
D. fimbriatum aloe-emodin chrysophanol
n-dotriacontanoic acid emodin
physcion rhein
(-)-shikimic acid
54
D. fuscescens (-)-shikimic acid 105
D. gibsonii aurantiamide acetate dimethyl terephthalate
70 70
D. moniliforme heptacosane
heptatriaconsanoic acid linoleic acid
methyl and ethyl linolenates 4-methoxybenzoaldehyde octacosanyl hexadecanoate vanillin
D. nakaharai protocatechuic acid（3,4-dihydroxy-benzoic acid）
trans-ß-carotene
5 5
D. superbum 4-(4-hydroxyphenyl)-2-butanone 96