結論

香蘭 (Pandanus amaryllifolius) 葉部氯仿層及正丁醇層藉由矽膠管柱層析、

高效能液相層析、薄層層析等方法進行細部分離後，共得到 26 個化合物，經

¹

H-NMR、UV、IR、EI-MS 與文獻比對確認，分別為 8 個苯環類、3 個紫羅蘭酮類、

2 個 單 萜 類 、 2 個 黃 酮 類 、 5 個 脂 肪 族 類 、 6 個 其 他 類 。 其 中 (5S)-1,1,3-Trimethylcyclohex-3-en-5-ol (eq) (80)與(5S)-1,1,3-(5S)-1,1,3-Trimethylcyclohex-3-en-5-ol (ax)

(81)為首次從天然物中分離得到。另外 Pinoresinol (88)、5-Hydroxymethyl furfural (90)、4-Hydroxybenzoic acid (70)、Dehydrovomifoliol

(77)、(E)-4-(3-Methoxyprop-1-en-1-yl) phenol (76)、3,4-Dihydroxybenzoic acid (72)、Blumenol-C (78)、Uridine

(91)、Methyl 3,4-dihydroxybenzoate

(71)、3β-Hydroxy-5α,6α-epoxy-7-megastigmen-9-one (79)、Methyl paraben (69)、Ethyl (E)-4-Hydroxycinnamate (73)、Ethyl (Z)-4-Hydroxycinnamate (74) 、 4-Methoxycinnamic acid (75) 、 Kaempferol 3-O-β-D-glucopyranoside (82) 、 Quercitrin (83) 、 2-Deoxy-D-ribonolactone (89) 、 Methyl linoleate (84)、Palmitic acid (85)、Methyl stearate (86)、Triacontanol (87)為首次從 香蘭植物中分離得到。

本研究在活性試驗結果顯示在 1.0 mg/mL 的濃度下，分離得到的化合物對 於抑制酪胺酸酶表現上，4-Hydroxybenzoic acid (70)、3,4-Dihydroxybenzoic acid

(72)、(5S)-1,1,3-Trimethylcyclohex-3-en-5-ol (eq) (80)有極佳抑制活性，另外中

4-Hydroxybenzoic acid (70)、(5S)-1,1,3-Trimethylcyclohex-3-en-5-ol (eq) (80)有與正 向對照相當的抑制效果。而在抑制 α-葡萄糖苷酶活性表現上 4-Hydroxybenzoic acid (70)、3,4-Dihydroxybenzoic acid (72)有極佳抑制活性。

本研究透過系統性的分析及活性研究，於試驗結果顯示出多種成分具有良好 之美白及降血糖活性，顯示出香蘭葉在美白及降血糖方面之開發潛力。

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附錄一 光譜數據

Linoleic acid (63) Colorless oil

Molecular formula: C

18

H

32

O

2

EI-MS (rel. int.) : m/z 256 (8), 213 (6), 129 (23), 105 (27) UV λ _max^MeOH: 210 nm

IR νmax cm

^-1

: 3400, 2922, 2855, 1717

1

H-NMR (CDCl

3

, 400 MHz):

δ 5.41 (4H, m, H-9, 10, 12, 13) δ 2.82 (2H, m, H-11)

δ 2.31 (2H, t, J = 7.6 Hz, H-2) δ 2.09 (4H, m, H-8, 14) δ 1.25 (16H, m)

δ 0.99 (3H, t, J = 7.2 Hz, H-18)

β-Sitosterol (65) White crystal

Molecular formula: C

29

H

50

O

EI-MS (rel. int.) : m/z 414 ([M]

⁺

, 50), 329 (40), 255 (70), 213 (70), 145 (85), 107 (80), 95 (89), 81 (100)

UV λ _max^MeOH: 210 nm

IR νmax cm

^-1

: 3400, 2939, 2853, 1460, 1384

1

H-NMR (CDCl

3

, 400 MHz):

δ 5.40 (1H, d, J = 5.6 Hz, H-6) δ 3.59 (1H, m, H-3)

δ 0.99 (3H, s, H-19) δ 0.91 (3H, m, H-21)

δ 0.75~0.87 (9H, m, H-26, 27, 29) δ 0.67 (3H, s, H-18)

Stigmasterol (66) White crystal

Molecular formula: C

29

H

48

O

EI-MS (rel. int.) : m/z 412 ([M]

⁺

, 20), 329 (40), 255 (70), 213 (70), 145 (85), 107 (80), 95 (89), 81 (100)

UV λ _max^MeOH: 210 nm

IR νmax cm

^-1

: 3400, 2939, 2853, 1460, 1384

1

H-NMR (CDCl

3

, 400 MHz):

δ 5.33 (1H, m, H-6)

δ 5.17 (1H, dd, J = 15.2, 8.4 Hz, H-22) δ 5.04 (1H, dd, J = 15.2, 8.4 Hz, H-23) δ 3.50 (1H, m, H-3)

δ 0.90 (3H, d, J = 8.4 Hz, CH

3

-21) δ 0.99 (3H, s, CH

3

-19)

δ 0.67 (3H, s, CH

3

-18)

δ 0.81-0.84 (9H, m, CH

3

-29, 26, 27) Methyl paraben (69)

Colorless oil

Molecular formula: C

8

H

8

O

3

EI-MS (rel. int.) : m/z 152 ([M]

⁺

, 5), 121 (14) UV λ _max^MeOH: 215, 235 nm

IR νmax cm

^-1

: 3412, 1560

1

H-NMR (CDCl

3

, 400 MHz):

δ 7.96 (2H, d, J = 9.2 Hz, H-3, 5) δ 6.87 (2H, d, J = 9.2 Hz, H-2, 6) δ 3.88 (3H, s, 7-OCH

3

)

4-Hydroxybenzoic acid (70) Brown oil

Molecular formula: C

7

H

6

O

3

EI-MS (rel. int.) : m/z 138 ([M]

⁺

, 20), 121 (35) UV λ _max^MeOH: 260 nm

IR νmax cm

^-1

: 3393, 1698, 1601

1

H-NMR (DMSO-d

6

, 400 MHz) δ 7.77 (2H, d, J = 8.4 Hz, H-2, 6) δ 6.80 (2H, d, J = 8.4 Hz, H-3, 5) δ 10.18 (1H, br., OH)

Methyl 3,4-dihydroxybenzoate (71) Colorless oil

Molecular formula: C

8

H

8

O

4

EI-MS (rel. int.) : m/z 168 ([M]

⁺

, 70), 153 (85), 125 (32), 97 (34) UV λ _max^MeOH: 260, 302 nm

IR νmax cm

^-1

: 3500~3000, 1555

1

H-NMR (CDCl

3

, 400 MHz):

δ 7.70 (1H, d, J = 8.0 Hz, H-6) δ 6.97 (1H, d, J = 8.0 Hz, H-5) δ 7.57 (1H, s, H-2)

δ 3.95 (3H, s, 7-OCH

3

)

3,4-Dihydroxybenzoic acid (72) Brown oil

Molecular formula:C

7

H

6

O

4

EI-MS (rel. int.) : m/z 154 ([M]

⁺

, 35), 137 (55) UV λ _max^MeOH: 260, 310 nm

IR νmax cm

^-1

: 2400~3400, 1568, 1408

1

H-NMR (DMSO-d

6

, 400 MHz) δ 7.31 (1H, d, J = 2.0 Hz, H-2) δ 7.25 (1H, dd, J = 8.4, 2.0 Hz, H-6) δ 6.74 (1H, d, J = 8.4 Hz, H-5) Ethyl (E)-4-Hydroxycinnamate (73) Colorless oil

Molecular formula: C

11

H

12

O

3

EI-MS (rel. int.) : m/z 192 ([M]

⁺

, 35), 147 (63) UV λ _max^MeOH: 227, 314 nm

IR νmax cm

^-1

: 3350, 1689, 1607, 1518

1

H-NMR (CDCl

3

, 400 MHz):

δ 7.44 (2H, d, J = 8.8 Hz, H-2, 6) δ 6.84 (2H, d, J = 8.8 Hz, H-3, 5) δ 7.60 (1H, d, J = 16.0 Hz, H-7) δ 6.31 (1H, d, J = 16.0 Hz, H-8) δ 4.19 (2H, m, H-1′)

δ 1.31 (3H, t, J = 6.8 Hz, H-2′) Ethyl (Z)-4-Hydroxycinnamate (74) Colorless oil

Molecular formula: C

11

H

12

O

3

EI-MS (rel. int.) : m/z 192 ([M]

⁺

, 35), 147 (63) UV λ _max^MeOH: 227, 314 nm

IR νmax cm

^-1

: 3350, 1689, 1607, 1518

1

H-NMR (CDCl , 400 MHz):

δ 7.62 (2H, d, J = 8.8 Hz, H-2, 6) δ 6.79 (2H, d, J = 8.8 Hz, H-3, 5) δ 6.84 (1H, d, J = 12.8 Hz, H-7) δ 5.84 (1H, d, J = 12.8 Hz, H-8) δ 4.19 (2H, m, H-1′)

δ 1.26 (3H, t, J = 7.2 Hz, H-2′) 4-Methoxycinnamic acid (75) Colorless oil

Molecular formula: C

10

H

10

O

3

EI-MS (rel. int.) : 178 ([M]

⁺

, 80), 147 (98) UV λ _max^MeOH: 312 nm

IR νmax cm

^-1

: 3400, 2926, 2857, 1719

1

H-NMR (CDCl

3

, 400 MHz):

δ 3.79 (3H, s, 1-OCH

3

)

δ 7.44 (2H, d, J = 8.8 Hz, H-3, H-5) δ 6.85 (2H, d, J = 8.8 Hz, H-2, H-6) δ 7.66 (1H, d, J = 16.0 Hz, H-7) δ 6.32 (1H, d, J = 16.0 Hz, H-8)

(E)-4-(3-Methoxyprop-1-en-1-yl) phenol (76) Colorless oil

Molecular formula: C

10

H

12

O

2

EI-MS (rel. int.) :119 ([M-CH

2

OCH

3

]

⁺

, 30) UV λ _max^MeOH: 261 nm

IR νmax cm

^-1

: 3400

1

H-NMR (CDCl

3

, 400 MHz):

δ 7.29 (2H, d, J = 8.8 Hz, H-2, H-6) δ 6.79 (2H, d, J = 8.8 Hz, H-3, H-5) δ 6.51 (1H, d, J = 15.6 Hz, H-7) δ 6.14 (1H, dd, J = 16.0, 6.4 Hz, H-8) δ 4.07 (2H, d, J = 6.4 Hz, H-9) δ 3.37 (3H, s, 10-OCH

3

) Dehydrovomifoliol (77) Colorless oil

Molecular formula: C

13

H

18

O

3

EI-MS (rel. int.) : m/z 166 ([M-C

4

H

8

]

⁺

, 44)

UV λ _max^MeOH: 250 nm

IR νmax cm

^-1

: 3465, 1657, 1611

1

H-NMR (CDCl

3

, 400 MHz):

δ 1.02 (3H, s, H-11) δ 1.10 (3H, s, H-12) δ 1.88 (3H, s, 13-CH

3

) δ 5.95 (1H, s, H-4)

δ 2.35 (1H, d, J = 17.2 Hz, H-2a) δ 2.52 (1H, d, J = 17.2 Hz, H-2b) δ 6.48 (1H, d, J = 15.6 Hz, H-8) δ 6.84 (1H, d, J = 15.6 Hz, H-7) δ 2.30 (3H, s, 10-CH

3

)

Blumenol-C (78) Colorless oil

Molecular formula: C

13

H

22

O

2

EI-MS (rel. int.) : m/z 170 ([M-C

3

H

4

]

⁺

, 40) UV λ _max^MeOH: 247 nm

IR νmax cm

^-1

: 3400, 1657

1

H-NMR (CDCl

3

, 400 MHz):

δ 1.05 (3H, s, H-13) δ 1.09 (3H, s, H-12) δ 2.02 (3H, s, 11-CH

3

) δ 5.84 (1H, s, H-4)

δ 2.24 (1H, d, J = 18.0 Hz, H-2a) δ 2.54 (1H, d, J = 18.0 Hz, H-2b) δ 1.23 (3H, d, J = 6.0 Hz, 10-CH

3

) δ 3.82 (1H, m, H-9)

δ 1.92 (1H, m, H-6) δ 1.89 (1H, m, H-7a)

δ 1.51~1.56 (3H, m, H-8a 8b, H-7b)

3β-Hydroxy-5α,6α-epoxy-7-megastigmen-9-one (79) Colorless oil

Molecular formula: C

13

H

20

O

3

EI-MS (rel. int.) : m/z 224 ([M]

⁺

, 1) UV λ _max^MeOH: 211, 279 nm

IR νmax cm

^-1

: 3306, 1641

1

H-NMR (CDCl

3

, 400 MHz):

δ 1.19 (6H, s, 11,12-CH

3

) δ 0.98 (3H, s, 13-CH

3

)

δ 6.30 (1H, d, J = 15.6 Hz, H-8) δ 7.04 (1H, d, J = 15.6 Hz, H-7) δ 2.28 (3H, s, 10-CH

3

)

δ 3.89 (1H, dd, J = 5.6, 5.2 Hz, H-3) δ 2.41 (1H, dd, J = 14.0, 5.6 Hz, H-2) δ 1.63 (1H, dd, J = 12.8, 5.2 Hz, H-4) δ 1.26 (1H, dd, J = 12.8, 5.2 Hz, H-4) δ 1.66 (1H, dd, J = 14.0, 5.6 Hz, H-2)

(5S)-1,1,3-Trimethylcyclohex-3-en-5-ol (eq) (80) Colorless oil

Molecular formula: C

9

H

16

O

EI-MS (rel. int.) : m/z 140 ([M]

⁺

, 25) IR νmax cm

^-1

: 3442

[ɑ]

_D ²⁷

= +4.6 (c 0.11, MeOH)

1

H-NMR (CDCl

3

, 400 MHz):

δ 1.26 (3H, s, 7-CH

3

) δ 1.31 (3H, s, 8-CH

3

) δ 1.58 (3H, s, 9-CH

3

) δ 5.71 (1H, s, H-2)

δ 1.50 (1H, t, J = 12.0 Hz, H-4) δ 1.32 (1H, t, J = 12.0 Hz, H-6) δ 2.04 (1H, dd, J = 12.0, 4.0 Hz, H-6) δ 2.55 (1H, dd, J = 12.0, 4.0 Hz, H-4) δ 4.11 (1H, tt, J = 12.0, 4.0 Hz, H-5)

(5S)-1,1,3-Trimethylcyclohex-3-en-5-ol (ax) (81) Colorless oil

Molecular formula: C

9

H

16

O

EI-MS (rel. int.) : m/z 140 ([M]

⁺

, 10), 125 (85) IR νmax cm

^-1

: 3416

[ɑ]

_D ²⁷

= +8.5 (c 0.05, MeOH)

1

H-NMR (CDCl

3

, 400 MHz):

δ 1.27 (3H, s, 7-CH

3

) δ 1.46 (3H, s, 8-CH

3

)

δ 1.78 (3H, s, 9-CH

3

) δ 5.69 (1H, s, H-2)

δ 1.95 (1H, dt, J = 14.0, 3.2 Hz, H-6) δ 2.43 (1H, dt, J = 14.0, 2.8 Hz, H-4) δ 4.33 (1H, tt, J = 3.2, 2.8 Hz, H-5) δ 1.81 (1H, dd, J = 14.0, 2.8 Hz, H-4) δ 1.52 (1H, dd, J = 14.0, 3.2 Hz, H-6) Kaempferol 3-O-β-D-glucopyranoside (82) Brown oil

Molecular formula: C

21

H

20

O

11

EI-MS (rel. int.) : m/z 286 ([M-C

6

H

10

O

5

]

⁺

, 75) UV λ _max^MeOH: 270, 350 nm

IR νmax cm

^-1

: 3360, 1650

1

H-NMR (DMSO-d

6

, 400 MHz):

δ 6.87 (2H, d, J = 7.2 Hz, H-3′, 5′) δ 7.97 (2H, d, J = 7.2 Hz, H-2′, 6′) δ 6.19 (1H, s, H-6)

δ 6.40 (1H, s, H-8)

δ 5.30 (1H, d, J = 6.8 Hz, H-1′′) Quercitrin (83)

Yellow oil

Molecular formula: C

21

H

20

O

11

UV λ _max^MeOH: 266 nm

IR νmax cm

^-1

: 3412, 2361, 2345, 1685

1

H-NMR (DMSO-d

6

, 400 MHz):

δ 7.53~7.51 (2H, d, J = 8.0 Hz, H-2′,6′) δ 6.83 (1H, d, J = 8.0 Hz, H-5′)

δ 6.37 (1H, d, J = 2.0 Hz, H-8) δ 6.18 (1H, d, J = 2.0 Hz, H-6) δ 5.26 (1H, s, H-1′′)

δ 3.90~3.18 (4H, m)

δ 0.97 (3H, d, J = 6.0 Hz, H-6′′) Methyl linoleate (84)

Yellow oil

Molecular formula: C H O

EI-MS (rel. int.) : m/z 294 ([M]

⁺

, 5), 279 (15), 167 (52), 149 (95), 83 (74) UV λ _max^MeOH: 211 nm

IR νmax cm

^-1

:3400 ,2929, 2859, 1737

1

H-NMR (CDCl

3

, 400 MHz):

δ 5.35 (4H, m, H-9, 10, 12, 13) δ 3.66 (3H, s, O-CH

3

)

δ 2.79 (2H, t, J = 6.4 Hz, H-11) δ 2.30 (2H, t, J = 7.6 Hz, H-2) δ 2.07 (4H, m, H-8, 14) δ 1.33 (16H, m)

δ 0.89 (3H, t, H-18) Palmitic acid (85)

White amorphous powder Molecular formula: C

16

H

32

O

2

EI-MS (rel. int.) : m/z 256 ([M]

⁺

, 26), 213 (15), 185 (18), 129 (32) UV λ _max^MeOH: 210 nm

IR νmax cm

^-1

: 3300, 2918, 2851, 1639

1

H NMR (CD

3

OD, 400 MHz):

δ 2.23 (2H, t, J = 7.2 Hz, H-2) δ 1.61 (2H, m, H-3)

δ 1.28 (24H, s, H-4~H-15) δ 0.89 (3H, t, J = 6.8 Hz, H-16) Methyl stearate (86)

Colorless oil

Molecular formula: C

19

H

38

O

2

EI-MS (rel. int.) : m/z267 ([M-OCH

3

]

⁺

, 5), 185 (20), 155 (25), 142 (32), 125 (31), 111 (48), 97 (53)

UV λ _max^MeOH: 212 nm

IR νmax cm

^-1

: 3393, 2929, 2859, 1737,1655 δ 3.66 (3H, s, O-CH

3

)

δ 2.31 (2H, t, J = 7.2 Hz, H-2) δ 1.25 (30H, m)

δ 0.89 (3H, t, J = 6.8 Hz, H-18) Triacontanol (87)

White crystal

Molecular formula: C

30

H

62

O

EI-MS (rel. int.) : m/z 313 (1), 239 (1), 125 (4), 111 (6) UV λ _max^MeOH: 213 nm

IR νmax cm

^-1

: 3300, 2918, 2851

1

H NMR (CDCl

3

, 400 MHz):

δ 3.65 (2H, t, J = 6.4 Hz, H-1) δ 1.57~1.55 (2H, s, H-2) δ 1.25 (54H, H-3~H-29)

δ 0.88 (3H, t, J = 6.4 Hz, H-30) Pinoresinol (88)

Colorless oil

Molecular formula：C

20

H

22

O

6

EI-MS (rel. int.) : m/z 358 ([M]

⁺

, 25) UV λ _max^MeOH: 230, 280 nm

IR νmax cm

^-1

：3400, 1520

1

H-NMR (CDCl

3

, 400 MHz):

δ 3.10 (2H, m, H-8, 8′)

δ 3.86 (2H, dd, J = 9.2, 4.0 Hz, H-9a, 9a′) δ 3.90 (6H, s, 2 OCH

3

)

δ 4.26 (2H, dd, J = 9.2, 6.8 Hz, H-9b, 9b′) δ 4.73 (2H, d, J = 4.0 Hz, H-7, 7′)

δ 5.60 (2H, s, 2 OH)

δ 6.83 (2H, dd, J = 8.0, 2.0 Hz, H-6, 6′) δ 6.88 (2H, d, J = 8.0 Hz, H-5, 5′) δ 6.89 (2H, d, J = 2.0 Hz, H-2, 2′) 2-Deoxy-D-ribonolactone (89) Colorless oil

Molecular formula：C

5

H

8

O

4

EI-MS (rel. int.) : m/z 133 ([M+1]

⁺

, 4), 115 (16), 101(15) IR νmax cm

^-1

：3388, 1024

1

H-NMR (CDCl

3

, 400 MHz):

δ 2.93 (1H, dd, J = 18.0, 4.5 Hz, H-2a) δ 2.51 (1H, dd, J = 18.0, 4.5 Hz, H-2b) δ 4.67 (1H, dt, J = 6.8, 3.2 Hz, H-4) δ 4.43 (1H, dt, J = 6.8, 4.5 Hz, H-3) δ 3.95 (1H, dd, J = 12.4, 3.2 Hz, H-5a)

δ 3.84 (1H, dd, J = 12.4, 3.2 Hz, H-5b) 5-Hydroxymethyl furfural (90)

Brown oil

Molecular formula : C

6

H

6

O

3

EI-MS (rel. int.) : m/z 126 ([M]

⁺

, 50), 97 (85) UV λ _max^MeOH: 280 nm

IR νmax cm

^-1

：3401, 1685, 1020

1

H-NMR (DMSO-d

6

, 400 MHz):

δ 6.59 (1H, d, J = 3.6 Hz, H-4) δ 7.48 (1H, d, J = 3.6 Hz, H-3) δ 9.53 (1H, s, H-1)

δ 4.49 (2H, s, H-6) δ 5.54 (1H, br., OH) Uridine (91)

Brown oil

Molecular formula : C

9

H

12

N

2

O

6

EI-MS (rel. int.) : m/z 245 ([M]

⁺

, 10) UV λ _max^MeOH: 260 nm

IR νmax cm

^-1

：3380, 1687

1

H-NMR (CD

3

OD, 400 MHz) : δ 8.01 (1H, d, J = 8.4 Hz, H-3) δ 5.69 (1H, d, J = 8.4 Hz, H-2) δ 5.89 (1H, d, J = 4.8 Hz, H-1′) δ 4.16~4.14 (2H, m, H-3′, H-4′) δ 4.00 (1H, m, H-2′)

δ 3.84 (1H, d, J = 12.4 Hz, H-5′) δ 3.73 (1H, d, J = 12.4 Hz, H-5′)

附錄二 植物的萃取與分離

將香蘭葉部520.0 g 先以乙酸乙酯浸泡，進行超音波震盪萃取 5 次，再以甲

醇浸泡，進行超音波震盪5 次，所得之萃取液合併經減壓濃縮除去溶劑，得初抽

物98.6 g，再以水與氯仿進行分配萃取，得氯仿層(PALC)，以水與正丁醇進行分

配萃取，得正丁醇層(PALB)，氯仿層及正丁醇層再經管柱層析法，薄層層析法及 液相層析儀作細部分離。

氯仿層以氯仿與甲醇(19:1)為沖提液，以甲醇漸增極性進行矽膠管柱層析分

離，經收集濃縮，再由TLC 檢測合併後得到 12 個劃分。

第二個劃分以高效能液相層析儀(RP-18)透過甲醇與乙腈(20:80)之混和溶劑 為 展 開 液 進 行 分 離 經 收 集 濃 縮 得 到 Blumenol-C (78) (2.0 mg) 、 (5S)-1,1,3-Trimethylcyclohex-3-en-5-ol (eq) (80) (1.4 mg)與 Dehydrovomifoliol (77) (0.7 mg)。

第三個劃分以正己烷與丙酮(3:1)之混和溶劑為展開液，加入丙酮漸增極性沖 提，進行矽膠管柱層析分離，經收集濃縮得到各細劃分層。再利用矽膠管柱層析、

薄層層析與以甲醇來清洗結晶得到Triacontanol (87) (16.5 mg)、β-Sitosterol (65)與 Stigmasterol (66) (1039.3 mg)。

第六個劃分以正己烷與丙酮(3:2)之混和溶劑為展開液，加入丙酮漸增極性沖 提，進行矽膠管柱層析分離，經收集濃縮得到各細劃分層。再利用矽膠管柱層析、

薄層層析及高效能液相層析儀(RP-18) 得到 Methyl stearate (86) (1.6 mg)、Methyl linoleate (84) (3.0 mg)、(5S)-1,1,3-Trimethylcyclohex-3-en-5-ol (ax) (81) (4.3 mg)、

Dehydrovomifoliol (77) (3.0 mg)、3β-Hydroxy-5α,6α-epoxy-7-megastigmen-9-one (79) (0.3 mg)、Pinoresinol (88) (4.1 mg)、Palmitic acid (85) (7.2 mg)、Linoleic acid (63) (2.0 mg)、Methyl paraben (69) (0.4 mg)、(E)-4-(3-Methoxyprop-1-en-1-yl) phenol (76) (0.4 mg)、Ethyl (E)-4-Hydroxycinnamate (73)與 Ethyl (Z)-4-Hydroxycinnamate (74) (1.9 mg)。

第十一個劃分以氯仿與甲醇(19:1)之混和溶劑為展開液，加入甲醇漸增極性 沖提，進行矽膠管柱層析分離，經收集濃縮得到各細劃分層。再利用矽膠管柱層 析、薄層層析得到(5S)-1,1,3-Trimethylcyclohex-3-en-5-ol (ax) (81) (0.2 mg)。

第十二個劃分以高效能液相層析儀(RP-18)透過甲醇與乙腈(15:85)之混和溶 劑為展開液進行分離經收集濃縮得到2-Deoxy-D-ribonolactone (89) (2.3 mg)。

正丁醇層以水與甲醇(4:1)為沖提液，以甲醇漸增極性進行逆向材料(Diaion HP-20)管柱層析分離，再由 TLC 檢測合併後得到 14 個劃分。

第三個劃分透過以氯仿與甲醇(3:1)為沖提液之混和溶劑為展開液進行分離，

再 利 用 矽 膠 管 柱 層 析 、 薄 層 層 析 與 高 效 能 液 相 層 析 儀(RP-18) 得 到 5-Hydroxymethyl furfural (90) (3.5 mg)與 Uridine (91) (10.8 mg)。

第四個劃分以(C-18)逆向管柱透過水與甲醇(19:1)之混和溶劑為展開液進行

分離，再利用高效能液相層析儀(RP-18)經收集濃縮得到 Uridine (91) (15.3 mg)。

第七個劃分以高效能液相層析儀(RP-18)透過甲醇與乙腈(8:92)之混和溶劑 且加入0.05% Trifluoroacetic acid (TFA)為展開液進行分離經收集濃縮得到 Uridine

(91) (8.6 mg)。

第八個劃分透過以氯仿、甲醇與水(5:1:1)為沖提液之混和溶劑為展開液進行 分離，再利用矽膠管柱層析、薄層層析得到5-Hydroxymethyl furfural (90) (2.6 mg)。

第九個劃分透過以氯仿、甲醇(4:1)為沖提液之混和溶劑為展開液進行分離，

再 利 用 矽 膠 管 柱 層 析 、 薄 層 層 析 與 高 效 能 液 相 層 析 儀(RP-18) 得 到 5-Hydroxymethyl furfural (90) (1.4 mg)與 3,4-Dihydroxybenzoic acid (72) (9.0 mg)。

第十一個劃分透過以氯仿、甲醇(4:1)為沖提液之混和溶劑為展開液進行分離，

再利用矽膠管柱層析、薄層層析得到 4-Hydroxybenzoic acid (70) (11.0 mg)、5-Hydroxymethyl furfural (90) (2.1 mg)、3,4-Dihydroxybenzoic acid (72) (10.0 mg)。

第十二個劃分透過以氯仿、甲醇與水(5:1:1)為沖提液之混和溶劑為展開液進 行分離，再利用矽膠管柱層析、薄層層析得到4-Hydroxybenzoic acid (70) (9.3 mg)。

第十三個劃分透過以氯仿、甲醇與水(5:1:1)為沖提液之混和溶劑為展開液進 行分離，再利用矽膠管柱層析、薄層層析得到Methyl 3,4-dihydroxybenzoate (71) (2.4 mg)與 4-Methoxycinnamic acid (75) (3.7 mg)。

第十四個劃分透過以氯仿、甲醇(10:1)為沖提液之混和溶劑為展開液進行分 離 ， 再 利 用 矽 膠 管 柱 層 析 、 薄 層 層 析 與 高 效 能 液 相 層 析 儀(RP-18)得到 4- Hydroxybenzoic acid (70) (8.7 mg)、Kaempferol 3-O-β-D-glucopyranoside (82) (30.8 mg)與 Quercitrin (83) (1.6 mg)。

在文檔中 香蘭葉部萃取物之生理活性成分研究 (頁 66-83)