第一章 緒論
第三節 桃實百日青植物介紹
羅漢松科 (Podocarpaceae)為常綠喬木或灌木。在全世界約有 20 屬，超過 120 種，分布於熱帶、亞熱帶和溫帶地區。主要以南半球為 主，僅少許分布於北半球僅其中多分布在菲律賓、印尼、馬來西亞印 度和中國大陸長江以南各省份。台灣地區本科原生種則有2 屬共 7 種 植物，依照1994 年第二版台灣植物誌第ㄧ卷所述，1分別隸屬於竹柏 屬(Nageia Gaerth.) 和羅漢松屬(Podocarpus L, H. erit ex Pers.)。前者有 長葉竹柏(N. fleuryi)及竹柏(N. nagi) 2 種，而後者包含蘭嶼羅漢松(P.
costalis)、大葉羅漢松 (P. macrophyllus var. macrophyllus)、小葉羅漢 松(P. macrophyllus var. maki )、叢花百日青(P. fasciculus) 和桃實百日 青(P. nakaii)等 5 種。其中叢花百日青和桃實百日青為台灣特有種，所 以在地理分布上有其特殊意義。
桃實百日青 (圖二)，主要分布在台灣中部中低海拔的闊葉林中
18，所以有許多的俗名，例如：土杉仔、百日青仔、山相思仔、百日 青、山相思樹、埔里羅漢松、埔里百日青及台灣羅漢松。桃實百日青 為常綠喬木，樹幹比直，樹高可達 15~20 餘公尺，樹幹直徑可達 60 公分，樹皮為灰紅褐色且有細長條的剝落，枝光滑，新芽略呈淡紅色，
葉為互生、細長、短柄或無柄、葉緣光滑且無毛、中脈明顯無側脈、
葉長披針型或寬線型約5~10 公分，葉寬約 8~12 公厘。桃實為雌雄異 株雄株約1-3 個雄毬花簇生，雌株開花期主要在秋季，種子約在夏季 成熟，先端的突起歪斜如桃子ㄧ般，種實球形，直徑約8 mm，生於 肥大之種托上。種托為倒錐狀圓柱形，長約1.5 cm， 成熟的種實，
種子著生在紅色的肉質種托上且種子表面有白色粉狀物，成熟時呈紅
外也有驅風、活血、解熱和解毒的功用。
另外，為了更了解本植物可能所含的化學成分，茲將本屬-羅漢 松屬 (Podocarpus)植物之文獻研究整理如下表(見表一)所示。羅漢松 科 植 物 現 有 發 現 的 化 合 物 中 ， 包 含 ；Fatty acids 、 Aromatics 、 Monoterpene 、 Sesquiterpenoids 、 Diterpenoids 、 Podolactones 、 Flavonoids、Biflavonoids 、Catechins、Steroids 和 Lignans 等不同骨 架的化合物，其中具有抗氧化、抗蟲和抗癌等功效。
圖一、桃實百日青植物外觀及其果實(黃士元 攝)
表一、羅漢松 (Podocarpus) 屬植物化合物之化學研究
Compound 化合物名稱 Source 基源 A. Fatty acids
Heptacosane (1) P. dacrydioides20 Hentriacontane (2) P. saligna21 Nonacosane (3) P. dacrydioides20 Eicosa-5c,11c,14c-trienoic acid (4) P. nagi22
Triacontane (5) P. saligna21 Ditetradecyl-carbinol (6) P. ferrugineos23 B. Aromatics
Benzene-1,4-diol (7) P. saligna21 Coumaric acid (8) P.macrophylla24 C. Monoterpene
(+)-Limonen (9) P. spicata25 D. Sesquiterpenoids
Atractylon (10) P. spicatus26 Curzerenone (11) P. spicatus26 Longifolene (12) P. spicatus26 γ-Muurolen (13) P. ferrugineus27 Bicyclogermacren (14) P. ferrugineus27 Selin-11-en-4α-ol (15) P. ferrugineus27 Selinadiene (16) P. spicatus26 δ-Cadinene (17) P. spicatus26 E. Diterpenoids
5β-Hydroxy-6-oxasugiyl methyl ether (23) P. ferrugineus29 Pimaradiene (24) P. spicatus26 (+)-Ferruginol (25) P. spicatus26 2-Ketoferruginol (26) P. ferrugineus29
表一、羅漢松 (Podocarpus) 屬植物化合物之化學研究(續) Compound 化合物名稱 Source 基源
6-Dehydroroyleanon (31) P. ferrugineus29 12-Acetoxysugiyl methyl ether (32) P. gracilior30 2β-Acetoxysugiyl methyl ether (33) P. ferrugineus29 5-Dehydrosugiol (34) P. ferrugineos23 19-Oxototarol (35) P. nagi31
8(14)-Sandaracopimaren-2α,15ξ,16,18-tetrol (36) P. halli32 Royleanon (37) P. ferrugineus29 Abietatriene-(8.11.13) (38) P. ferrugineus27 Rimuene (39) P. saligna21 Isopimaradiene (40) P. spicatus26 17-Isophyllocladenol (41) P. lambertius33 Totarol (42) P. totara34 Hydroxytotarol (43) P. totara34 19-Hydroxytotarol (44) P. nagi31 Phylloclad-15-ene (45) P. spicatus26 Isopimarol (46)
Isopimaradiene (47)
P. spicatus26 P. ferrugineus29 19-Hydroxyferruginol (48) P. ferrugineus35 Totaryl acetate (49) P. gracilior30 Methyl podocarpate (50) P. totara34
4β-Carboxy-17-hydroxy-19-nortotarol (51) P. macrophyllus36 Phyllocladen (52) P. spicatus26
Isopimara-8,15-diene (53) P. spicatus26 Pimara-8(14),15-diene (54) P. spicatus26 3β-Hydroxytotarol (55) P. nagi31 Podocarpic acid (56) P. lambertius33 Lambertic acid (57) P. lambertius33 Pododacric acid (58) P. lambertius33 8,9-Abieten-15-ol (59) P. lambertius33 Sempervirol (60) P. gracilior30 8-Hydroxy-isopimarene (61) P. spicatus26
表一、羅漢松 (Podocarpus) 屬植物化合物之化學研究(續) Compound 化合物名稱 Source 基源
Totaral (66) P. nagi38 16-Hydroxy-totarol (67) P. nagi38
Abieta-6,8,11,13-tetraen-12-ol (68) P. dacrydioides20 Cupressene (69) P. dacrydioides20 Kaurane (70) P. macrophyllus36 Phyllocladene (71) P. ferruginea37 Isokaurene (72) P. spicatus26 Rosadiene (73) P. spicatus26 Sandaracopimaradienes (74) P. spicatus26 Carnosol (75) P. ferrugineus35 19-Acetate (76) P. ferrugineus35 Totaradiol (77) P. nagi38
4β-Carboxy-19-nortotarol (78) P. macrophyllus36 Macrophyllinoic acid (79) P. ferrugineus35 F. Podolactones
Inumakilactone (80) P. macrophyllus39 Hallacton A (81) P. hallii40
Nagilactone B (82) P. macrophyllus41 1-Deoxy-2,3-dehydronagilactone (83) P. nagi42
Nagilalacton A (84) P. nagi43 Podolacto E (85) P. neriifolius44 Nagilactone A (86) P. macrophyllus41 LactoneA (87) P. saligna45 15-Methoxycarbonyl-Nagilactone D (88) P. nagi46 Nubilacton A (89) P. nubigena47 Nagilalacton E (90) P. nagi43 Nagilactone F (91) P. nagi43 Nagilactone B (92) P. nagi46 Nagilactone D (93) P. nagi46
1-Deoxy-3β-hydroxy-nagilactone B (94) P. macrophyllus41 17-Hydroxy-3-deoxy-2,3-didehydro-nagilactone E (95) P. nagi46
表一、羅漢松 (Podocarpus) 屬植物化合物之化學研究(續) Compound 化合物名稱 Source 基源
Podolacton A (99) P. neriifolius48 Podolacton B (100) P. neriifolius48 2β,3β-Epoxy-podolid (101) P. neriifolius48 Inumakilactone B (102) P. neriifolius44 2,3-Dehydro-16-hydroxynagilactone F (103) P. nagi49 16-Hydroxynagilactone E (104) P. nagi49 Nagilactone I (105) P. nagi49 Nagilactone A (106) P. nagi49 Nagilactone C (107) P. nagi49 3-Deoxy-2α-hydroxynagilactone E (108) P. nagi49 2α-Hydroxynagilactone F (109) P. nagi49 3-Epinagilactone C (110) P. nagi49 Nagilactone J (111) P. nagi50 Salignone H (112) P. saligna51 Salignone A (113) P. saligna51 α,β-Unsaturatedδ-laction (114) P. urbanii52 Urbalactone (115) P. urbanii52 Inumakilactone A (116) P. neriifolius44 1-Deoxynagilactone A (117) P. nagi42 2,3-Dehydronagilactone (118) P. nagi42 Salignone M (119) P. saligna53 Nagilactone (120) P. nagi42 Salignone I (121) P. saligna53 Salignone K (122) P. saligna53 Salignone L (123) P. saligna53 Salignone J (124) P. saligna53 Salignone A (125) P. saligna53 Inumakilactone D (126) P. saligna53 Rakanmakilactone I (127) P. macrophyllus36 Rakanmakilactone H (128) P. macrophyllus36 Rakanmakilactone G (129) P. macrophyllus36
表一、羅漢松 (Podocarpus) 屬植物化合物之化學研究(續) Compound 化合物名稱 Source 基源
Podolacton C (133) P. macrophyllus54 Hallacton B (134) P. hallii40
Podolacton D (135) P. macrophyllus54 Rakanmakilactone A (136) P. macrophyllus54 Rakanmakilactone C (137) P. macrophyllus54 Rakanmakilactone D (138) P. macrophyllus54 Rakanmakilactone B (139) P. macrophyllus54 Rakanmakilactone F (140) P. macrophyllus54 Hallactone B (141) P. macrophyllus54 Podolactone C (142) P. macrophyllus54 Rakanmakilactone E (143) P. macrophyllus54 G. Biflavonoids
Hinokiflavone (144) P. elongata55 Amentoflavone (145) P. macrophylla24 Isoginkgetin (146) P. gracilior24 4',4''',7,7''-Tetra-methylamentoflavone(147) P. urbanii52 Amentoflavone hexa-acetate (148) P. urbanii52 Hexa-O-methylcupressuflavone (149) P. elongatus56 Ketoflavone (150) P. elongatus57 Heveaflavone (151) P. taxifolia58 Sotetsuflavone (152) P. elongatus57 Podocarpus-flavon A (153) P. urbanii52 II 4׳-Methylamentoflavone (154) P. taxifolia58 I 7, II 4׳-Dimethylamentoflavone (155) P. taxifolia58 Podocarpus flavone A (156) P. urbanii52 Podocarpusflavanone (157) P. taxifolia58 H. Flavonoids
Katuranin (158 ) P. spicatus59 Dihydroquercetin (159) P. spicatus60 Apigenin (160) P. macrophylla24 Kaempferol (161) P. spicatus59
表一、羅漢松 (Podocarpus) 屬植物化合物之化學研究(續) Compound 化合物名稱 Source 基源
Biochanin A (165) P. andina28 Irisolidone (166) P. andina28 Podospicatin (167) P. spicatus60 Taxifolin 7-O-β-glucoside (168) P. nivalis61 Luteolin 3'-O-β-xyloside (169) P. nivalis61 Co-occurring glycoside (170) P. nivalis61 5-O-β-D-Glucopyranoside (171) P. nivalis61 Luteolin 7-O-βglucoside-3'-O-β-xyloside(172) P. nivalis61 Orientin 2"-O-βglucopyranoside (173) P. nivalis61 Vitexin-2"-O-glucoside (174) P. nivalis61 I. Catechins
(-)-Epicatechin (175) P. nagi62 Cyanidin-3-rutinosid (176) P. lawrencii63 Peonidin-3,5-diglucosid (177) P. brevifolius64 Cyanidin-3-glucosid (178) P. lawrencii63 Peonidin-3-glucosid (179) P. brevifolius64 Myrtillin (180) P. totara65 Pelargonidin-3-glucosid-chlorid (181) P. brevifolius64 Delphinidin-3-glucoside-chloride (182) P. brevifolius64 Pelargonidin-3,5-diglucosid-chlorid (183) P. brevifolius64 Delphinidin-3,5-diglucoside-chloride (184) P. brevifolius64 Cyanidin-3-rutinoside (185) P. totara65 Delphinidin-3-neohesperidoside (186) P. totara65 Cyanidin 3-neohesperidoside (187) P. totara65 J. Steroids
β-Sitosterin (188) P. ferrugineos23
Stigmasterol (189) P. pivalis66 Clionasterol (190) P. totara34
20-Hydroxy-ecdysone (191) P. macrophyllus67 Ponasteron B (192) P. urbanii68 Ponasteron C (193) P. urbanii68
表一、羅漢松 (Podocarpus) 屬植物化合物之化學研究(續) Compound 化合物名稱 Source 基源
Makisteron A (197) P. macrophyllus67 3β,5α-Dihydroxy-6-stigmastanone (198) P. lambertius33 24(ξ)-Methyl-25(ξ)-cholest-5-ene-3b,26-diol (199) P. macrophylla24 24(ξ)-Ethyl-25(ξ)-cholest-5-ene-3b,26-diol (200) P. macrophylla24 Sitosterol-D-glucoside (201) P. latifolius70 K. Lignans
Matairesinol (202) P. spicatus71 Thujaplicatin methyl ether (203) P. spicatus71 L. Other
Hallol (204) P. halli32 Sequoyitol (205) P. sellowii72 Blumenol C (206) P. blume73 Blumenol B (207) P. blume73 Lauren-1-ene (208) P. halli32 Waihoensene (209) P. totara74
A. Fatty acids
1 2
4
OH
6 5
HO
3 O
B. Aromatics
HO OH
7
HO O
8 OH
C. Monoterpene
9
D. Sesquiterpenoids
22
E. Diterpenoids
O
O
OH
OH
44 45 46
47 48 49
50 51
53 54 55
OH
OH
OH
OH
OH
HOOC OH
O
OH
52
HO
OH
56 57 58
59 60 61
62 63 64
65 66 67
OH
OH O
OH OH
OH OH
OH
OH
OH
OH
OH OH
O
OH O
OH H
O
68 69 70
71 72 73
74 75 76
77 78 79
OH
OHO
OH
O
OH
O
O
HO
OH
OH
OH
O OH
O
O OH
F. Podolactones
92 93 94
95 96 97
98 99 100
101 102 103
O
104 105 106
107 108 109
110 111 112
113 114 115
O
116 117
118
119 120 121
122 123 124
125 126 127
O
128 129 130
131 132 133
134 135 136
137 138 139
O
O
140 141 142
143
G. Biflavonoids
144 145 146
147 148 149
O
150 151 152
153 154 155
156 157
H. Flavonoids
O HO
OH O OH
OH
158 159 160
O
161 162 163
164 165 166
O
167 168 169
O
170 171 172
O
173 174
175 176 177
178 179 180
181 182 183
O
O OH
J. Steroids
HO
188 189 190
191 192 193
HO HO
194 195 196
197 198 199
200
L. Other
HO
HO
OH
HO
204 205
207
206
208 209
OH HO
HO
OH OH
O O
OH
O
OH OH
圖二、羅漢松(Podocarpus)屬植物化合物之化學結構(續)