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Chemical constituents from frankincense

乳香的化学成分研究



全 文 :中草药 Chinese Traditional and Herbal Drugs 第 42 卷 第 7 期 2011 年 7 月

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乳香的化学成分研究
王 峰 1, 2,华会明 2,王淑美 1,梁生旺 1
1. 广东药学院中药学院,广东 广州 510006
2. 沈阳药科大学中药学院,辽宁 沈阳 110016
摘 要:目的 研究橄榄科植物卡氏乳香树 Boswellia carterii 的树脂氯仿提取物的化学成分。方法 利用色谱方法对乳香化
学成分进行分离纯化,并根据理化性质和波谱数据鉴定化合物的结构。结果 从乳香氯仿提取物中分离得到 14 个化合物,
分别鉴定为 α-香树素(1)、β-乳香酸(2)、乙酰 11α-甲氧基-β-乳香酸(3)、11-羰基-β-乳香酸(4)、乙酰 11-羰基-β-乳香酸
(5)、9, 11-去氢-β-乳香酸(6)、乙酰 α-乳香酸和乙酰 β-乳香酸(7)、α-乳香酸(8)、9, 11-去氢-α-乳香酸(9)、α-乙酰榄香
醇酸(10)、3α-羟基甘遂-8, 24-二烯-21-酸(11)、榄香酮酸(12)、3α-羟基甘遂-7, 24-二烯-21-酸(13)、α-棕榈酸甘油酯(14)。
结论 化合物 1 和 9 为首次从该属植物中分离得到。
关键词:卡氏乳香树;乳香;三萜;α-香树素;9, 11-去氢-α-乳香酸
中图分类号:R284.1 文献标志码:A 文章编号:0253 - 2670(2011)07 - 1293 - 04
Chemical constituents from frankincense
WANG Feng1, 2, HUA Hui-ming2, WANG Shu-mei1, LIANG Sheng-wang1
1. School of Chinese Materia Medica, Guangdong Pharmaceutical University, Guangzhou 510006, China
2. School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China
Key words: Boswellia carterii Birdw.; frankincense; triterpenoids; α-amyrin; 9, 11-dehydro-α-boswellic acid

乳香为橄榄科植物卡氏乳香树 Boswellia
carterii Birdw. 的树脂。主产于红海沿岸的索马里和
埃塞俄比亚。此外尚有同属植物鲍达乳香树 B.
bhaw-dajiana Birdw.及野乳香树 B. neglecta M.
Moore 等数种。现代药理研究表明,乳香中的乳香
酸类化合物具有抗炎作用和对肿瘤细胞有抗增殖、
分化诱导和凋亡诱导作用[1],郭辉等[2]报道了乳香
中抗哮喘有效部位的化学成分。本课题组采用多种
色谱技术,从卡氏乳香树树脂的氯仿提取物中,分
离得到 14 个化合物,分别鉴定为 α-香树素
(α-amyrin,1)、β-乳香酸(β-boswellic acid,2)、
乙酰 11α-甲氧基-β-乳香酸(acetyl 11α-methoxy-
β-boswellic acid,3)、11-羰基-β-乳香酸(11-keto-β-
boswellic acid,4)、乙酰 11-羰基-β-乳香酸(acetyl
11-keto-β-boswellic acid,5)、9, 11-去氢-β-乳香酸(9,
11-dehydro-β-boswellic acid,6)、乙酰 α-乳香酸和
乙酰 β-乳香酸(acetyl α-boswellic acid 和 acetyl
β-boswellic acid,7)、α-乳香酸(α-boswellic acid,
8)、9, 11-去氢-α-乳香酸(9, 11-dehydro-α-boswellic
acid,9)、α-乙酰榄香醇酸(α-acetyl elemolic acid,
10)、3α-羟基甘遂-8, 24-二烯-21-酸(3α-hydroxy-
tirucalla-8, 24-dien-21-oic acid, 11)、榄香酮酸
(elemonic acid,12)、3α-羟基甘遂烷-7, 24-二烯-21-
酸(3α-Hydroxytirucalla-7, 24-dien-21-oic acid,13)、
α-棕榈酸甘油酯(α-glyceryl palmitate,14)。
1 仪器和材料
核磁共振波谱仪为 Bruker ARX 300 NMR
spectrometer和Bruker ARX 600 NMR Spectrometer,
TMS 做内标;质谱仪为 Shimadzu GCMS―QP5050A,
Agilent 1100 SL,Autospec-Ultima ETOF。色谱柱硅
胶(200~300 目)和薄层色谱用硅胶 H、GF254 购
于青岛海洋化工厂;ODS、Sephadex LH-20 购于
GE Healthcare。
乳香购于辽宁省药材公司,经沈阳药科大学中
药学院药用植物教研室孙启时教授鉴定为卡氏乳
香树Boswellia carterii Birdw. 的树脂,标本(20070918)

收稿日期:2010-11-02
基金项目:广东省中医药局项目(2009420)
作者简介:王 峰(1977—),男,理学博士,从事活性天然产物的研究。Tel: (020)39352181 E-mail: wfeng1230@163.com
中草药 Chinese Traditional and Herbal Drugs 第 42 卷 第 7 期 2011 年 7 月

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保存于沈阳药科大学中药学院。
2 提取与分离
乳香树脂 1 kg,经粉碎后,以氯仿回流提取 3
次,合并 3 次提取液,浓缩干燥,得浸膏 678 g。
进行硅胶柱色谱(200~300 目)分离,以石油醚-
醋酸乙酯梯度洗脱,将各个梯度所得流份合并,再
经反复硅胶、Sephadex LH-20 及反相 ODS 开放柱
色谱分离,并重结晶得化合物 1(18 mg)、2(6 mg)、
3(7 mg)、4(5 mg)、5(1 700 mg)、6(8 mg)、7
(3 432 mg)、8(9 mg)、9(8 mg)、10(3 173 mg)、
11(7 mg)、12(1 500 mg)、13(9 mg)、14(30 mg)。
3 结构鉴定
化合物 1:白色无定形粉末(丙酮),10%硫酸
乙醇溶液显色为红色。1H-NMR (300 MHz, CDCl3)
δ: 0.79 (6H, s), 0.80 (3H, s), 0.96 (3H, s), 1.00 (6H, s),
1.01 (3H, s), 1.07 (3H, s), 3.25 (1H, dd, J = 10.1, 4.5
Hz, H-3), 5.31 (1H, br s, H-12);13C-NMR (75 MHz,
CDCl3) δ: 38.8 (C-1), 27.3 (C-2), 79.1 (C-3), 38.8
(C-4), 55.2 (C-5), 18.3 (C-6), 32.9 (C-7), 40.0 (C-8),
47.7 (C-9), 36.9 (C-10), 23.3 (C-11), 124.4 (C-12),
139.6 (C-13), 42.0 (C-14), 28.7 (C-15), 26.6 (C-16),
33.7 (C-17), 59.1 (C-18), 39.6 (C-19), 39.6 (C-20), 31.2
(C-21), 41.5 (C-22), 28.1 (C-23), 15.6 (C-24), 15.6
(C-25), 16.9 (C-26), 23.3 (C-27), 28.1 (C-28), 17.5
(C-29), 21.4 (C-30)。以上数据与文献报道一致[3],
故鉴定化合物 1 为 α-香树素。
化合物 2:无色针晶(丙酮),10%硫酸乙醇溶
液显色为红色。1H-NMR (300 MHz, CDCl3) δ: 0.80
(6H, s), 0.90 (6H, s), 1.04 (3H, s), 1.09 (3H, s), 1.35
(3H, s), 4.08 (1H, br s, H-3), 5.14 (1H, br s, H-12);
13C-NMR (75 MHz, CDCl3) δ: 33.9 (C-1), 26.2 (C-2),
70.7 (C-3), 47.3 (C-4), 49.1 (C-5), 19.7 (C-6), 33.1
(C-7), 40.0 (C-8), 46.8 (C-9), 37.5 (C-10), 23.4
(C-11), 124.5 (C-12), 139.6 (C-13), 42.3 (C-14), 26.5
(C-15), 28.1 (C-16), 33.8 (C-17), 59.2 (C-18), 39.7
(C-19), 39.6 (C-20), 31.3 (C-21), 41.5 (C-22), 24.2
(C-23), 182.7 (C-24), 13.3 (C-25), 16.9 (C-26), 23.2
(C-27), 28..8 (C-28), 17.4 (C-29), 21.4 (C-30)。以上数
据与文献报道一致[4],故鉴定化合物 2 为 β-乳香酸。
化合物 3:无色针晶(丙酮),10%硫酸乙醇溶
液显色为红色。EI-MS m/z: 528 [M]+, 496, 323, 248
(100), 119。1H-NMR (300 MHz, CDCl3) δ: 0.81 (3H,
s, Me-28), 0.90 (3H, d, J = 5.8 Hz, Me-29), 0.93 (3H,
s, Me-30), 1.03 (3H, s, Me-25), 1.09 (3H, s, Me-26),
1.20 (3H, s, Me-27), 1.24 (3H, s, Me-23), 2.06
(CH3CO), 3.28 (3H, s, CH3O), 3.82 (1H, dd, J = 9.0,
3.0 Hz, H-11), 5.28 (1H, br s, H-3), 5.36 (1H, d, J =
3.0 Hz, H-12);13C-NMR (75 MHz, CDCl3) δ: 35.6
(C-1), 23.7 (C-2), 73.2 (C-3), 46.7 (C-4), 50.4 (C-5),
19.4 (C-6), 33.1 (C-7), 42.2 (C-8), 51.4 (C-9), 38.5
(C-10), 77.0 (C-11), 124.0 (C-12), 143.5 (C-13), 42.8
(C-14), 26.6 (C-15), 27.9 (C-16), 33.6 (C-17), 58.6
(C-18), 39.5 (C-19), 39.3 (C-20), 31.1 (C-21), 41.3
(C-22), 24.0 (C-23), 182.2 (C-24), 14.4 (C-25), 18.1
(C-26), 22.4 (C-27), 28.7 (C-28), 17.3 (C-29), 21.3
(C-30), 54.5 (CH3O), 170.4 (CH3CO), 21.3 (CH3CO)。
以上数据与文献报道一致[5],故鉴定化合物 3 为乙
酰 11α-甲氧基-β-乳香酸。
化合物 4:无色针晶(丙酮),10%硫酸乙醇溶
液不显色。1H-NMR (300 MHz, CDCl3) δ: 0.79 (3H,
d, J = 6.3 Hz), 0.82 (3H, s), 0.94 (3H, s), 1.13 (3H,
s), 1.18 (3H, s), 1.31 (3H, s), 1.35 (3H, s), 4.08 (1H,
br s, H-3), 5.55 (1H, br s, H-12);13C-NMR (75 MHz,
CDCl3) δ: 33.9 (C-1), 23.5 (C-2), 73.4 (C-3), 45.1
(C-4), 48.8 (C-5), 18.3 (C-6), 32.6 (C-7), 43.7 (C-8),
60.4 (C-9), 37.4 (C-10), 200.6 (C-11), 130.4 (C-12),
165.2 (C-13), 45.0 (C-14), 27.5 (C-15), 27.3 (C-16),
33.9 (C-17), 58.9 (C-18), 39.2 (C-19), 39.2 (C-20), 30.9
(C-21), 40.9 (C-22), 24.4 (C-23), 182.2 (C-24), 13.1
(C-25), 18.3 (C-26), 21.1 (C-27), 28.8 (C-28), 17.4
(C-29), 20.5 (C-30)。以上数据与文献报道一致[5],
故鉴定化合物 4 为 11-羰基-β-乳香酸。
化合物 5:无色针晶(丙酮),10%硫酸乙醇溶
液不显色。EI-MS m/z: 512 [M]+, 497, 453, 273 (100),
232, 135。1H-NMR (300 MHz, CDCl3) δ: 0.78 (3H, d,
J = 6.4 Hz, CH3-29), 0.80 (3H, s, CH3-28), 0.93 (3H,
br s, CH3-30), 1.12 (3H, s, CH3-25), 1.18 (3H, s,
CH3-26), 1.22 (3H, s, CH3-23), 1.33 (3H, s, CH3-27),
2.07 (3H, s, CH3CO), 5.28 (1H, br s, H-3), 5.54 (1H,
s, H-12);13C-NMR (75 MHz, CDCl3) δ: 34.6 (C-1),
23.5 (C-2), 73.1 (C-3), 46.5 (C-4), 50.4 (C-5), 18.7
(C-6), 32.8 (C-7), 45.1 (C-8), 60.3 (C-9), 37.4 (C-10),
199.4 (C-11), 130.5 (C-12), 165.1 (C-13), 43.8 (C-14),
27.5 (C-15), 27.2 (C-16), 34.0 (C-17), 59.0 (C-18), 39.3
(C-19), 39.3 (C-20), 30.9 (C-21), 40.9 (C-22), 23.8
(C-23), 182.1 (C-24), 13.2 (C-25), 18.4 (C-26), 20.5
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(C-27), 28.9 (C-28), 17.4 (C-29), 21.1 (C-30), 170.3
(CH3CO), 21.3 (CH3CO)。以上数据与文献报道一致[5],
故鉴定化合物 5 为乙酰 11-羰基-β-乳香酸。
化合物 6:白色无定形粉末(甲醇),10%硫酸
乙醇溶液显色为红色。1H-NMR (300 MHz, CDCl3)
δ: 0.80 (3H, d, J = 6.3 Hz), 0.86 (3H, s), 0.93 (6H, s), 1.11
(3H, s), 1.19 (3H, s), 1.37 (3H, s), 4.09 (1H, br s, H-3),
5.46 (1H, d, J = 6.0 Hz), 5.65 (1H, d, J = 6.0 Hz);
13C-NMR (75 MHz, CDCl3) δ: 33.6 (C-1), 22.4 (C-2),
72.9 (C-3), 46.9 (C-4), 47.4 (C-5), 19.5 (C-6), 31.8 (C-7),
43.4 (C-8), 152.7 (C-9), 39.0 (C-10), 122.9 (C-11), 116.4
(C-12), 141.6 (C-13), 40.6 (C-14), 26.2 (C-15), 28.2
(C-16), 33.7 (C-17), 57.3 (C-18), 39.4 (C-19), 39.0 (C-20),
31.2 (C-21), 41.3 (C-22), 23.7 (C-23), 183.2 (C-24), 23.4
(C-25), 21.6 (C-26), 17.4 (C-27), 28.7 (C-28), 17.4
(C-29), 21.8 (C-30)。以上数据与文献报道一致[6],
故鉴定化合物 6 为 9, 11-去氢-β-乳香酸。
化合物 7:无色结晶(石油醚-醋酸乙酯),10%
硫酸乙醇溶液显色为紫色。EI-MS m/z: 498 [M]+,
483, 423, 394, 218 (100)。 1H-NMR (300 MHz,
CDCl3) δ: 0.80 ~ 1.30 (CH3 × 14), 2.11 (6H, s,
CH3COO), 5.30 (2H, br s, H-3), 5.20 (1H, br s, H-12),
5.15 (1H, br s, H-12)。以上数据与文献报道的 α-乙
酰乳香酸和 β-乙酰乳香酸混合物一致[5],故鉴定化
合物 7 为 α-乙酰乳香酸和 β-乙酰乳香酸混合物。
化合物 8:无色针晶(丙酮),10%硫酸乙醇溶
液显色为红色。EI-MS m/z: 456 [M]+, 441, 423, 395,
218 (100), 203。 MeOHmaxUV λ (nm): 205。 KBrmaxIR ν (cm−1):
3 445, 2 948, 1 696, 1 457, 1 381, 1 234, 1 194, 1 055,
1 026, 994。1H-NMR (300 MHz, CDCl3) δ: 0.83 (3H,
s, CH3-28), 0.86 (3H, s, CH3-29), 0.87 (3H, s,
CH3-30), 0.88 (3H, s, CH3-25), 1.00 (3H, s, CH3-26),
1.15 (3H, s, CH3-27), 1.34 (3H, s, CH3-23), 4.08 (1H,
br s, H-3), 5.19 (1H, br s, H-12);13C-NMR (75 MHz,
CDCl3) δ: 33.6 (C-1), 26.1 (C-2), 70.7 (C-3), 47.4
(C-4), 49.1 (C-5), 19.7 (C-6), 32.7 (C-7), 39.8 (C-8),
46.7 (C-9), 37.6 (C-10), 23.5 (C-11), 121.7 (C-12),
145.1 (C-13), 41.9 (C-14), 26.0 (C-15), 26.9 (C-16),
32.5 (C-17), 47.3 (C-18), 46.7 (C-19), 31.1 (C-20), 34.7
(C-21), 37.1 (C-22), 24.2 (C-23), 183.2 (C-24), 13.0
(C-25), 16.7 (C-26), 25.9 (C-27), 28.4 (C-28), 33.3
(C-29), 23.7 (C-30)。以上数据与文献报道一致[4],
故鉴定化合物 8 为 α-乳香酸。
化合物 9:白色无定形粉末(甲醇),易溶于氯
仿,10%硫酸乙醇溶液显色为红色。1H-NMR (300
MHz, CDCl3) δ: 0.88 (3H, s), 0.89 (3H, s), 0.90 (3H,
s), 1.03 (3H, s), 1.11 (3H, s), 1.16 (3H, s), 1.38 (3H,
s), 4.10 (1H, br s, H-3), 5.51 (1H, d, J = 6.0 Hz), 5.65
(1H, d, J = 6.0 Hz);13C-NMR (75 MHz, CDCl3) δ:
33.2 (C-1), 23.2 (C-2), 70.3 (C-3), 46.9 (C-8), 47.6
(C-5), 19.6 (C-6), 31.9 (C-7), 43.0 (C-8), 152.3 (C-9),
39.2 (C-10), 120.6 (C-11), 116.9 (C-12), 147.5 (C-13),
40.6 (C-14), 26.9 (C-15), 28.7 (C-16), 33.7 (C-17),
46.9 (C-18), 45.6 (C-19), 31.1 (C-20), 34.6 (C-21),
37.0 (C-22), 23.7 (C-23), 181.2 (C-24), 23.2 (C-25),
20.5 (C-26), 20.0 (C-27), 28.7 (C-28), 33.2 (C-29),
24.1 (C-30)。以上数据与文献报道一致[7],故鉴定
化合物 9 为 9, 11-去氢-α-乳香酸。
化合物 10:无色针晶(丙酮),10%硫酸乙醇
溶液显色为红色。1H-NMR (300 MHz, CDCl3) δ:
0.75~0.97 (CH3×5), 1.59 (3H, s), 1.68 (3H, s), 2.06
(3H, s, CH3CO), 4.65 (1H, br s, H-3), 5.10 (1H, t, J =
6.6 Hz, H-24);13C-NMR (75 MHz, CDCl3) δ: 31.2
(C-1), 27.3 (C-2), 76.5 (C-3), 37.3 (C-4), 44.3 (C-5),
20.1 (C-6), 28.9 (C-7), 133.4 (C-8), 133.2 (C-9), 37.0
(C-10), 25.1 (C-11), 31.3 (C-12), 43.7 (C-13), 49.6
(C-14), 28.4 (C-15), 28.5 (C-16), 46.9 (C-17), 19.7
(C-18), 16.6 (C-19), 47.3 (C-20), 182.5 (C-21), 22.4
(C-22), 26.5 (C-23), 123.6 (C-24), 132.7 (C-25), 17.6
(C-26), 23.7 (C-27), 24.2 (C-28), 19.2 (C-29), 26.8
(C-30), 170.3 (CH3CO), 21.7 (CH3CO)。以上数据与
文献报道一致[8-9],故鉴定化合物 10 为 α-乙酰榄香
醇酸。
化合物 11:无色针晶(丙酮),10%硫酸乙醇
溶液显色为红色。EI-MS m/z: 456 [M]+, 441 [M-
CH3], 423 [M-CH3-H2O] 。 1H-NMR (300 MHz,
CDCl3) δ: 0.79 (3H, s), 0.82 (3H, s), 0.88 (3H, s), 0.93
(3H, s), 0.97 (3H, s), 1.00 (3H, s), 1.55 (3H, s), 1.68
(3H, s), 3.25 (1H, br s, H-3), 5.09 (1H, t, J = 6.6 Hz,
H-24);13C-NMR (75 MHz, CDCl3) δ: 35.5 (C-1), 27.1
(C-2), 79.1 (C-3), 39.0 (C-4), 51.1 (C-5), 19.1 (C-6),
28.8 (C-7), 134.1 (C-8), 132.3 (C-9), 37.2 (C-10), 26.1
(C-11), 32.5 (C-12), 44.0 (C-13), 50.0 (C-14), 29.4
(C-15), 28.0 (C-16), 47.0 (C-17), 20.1 (C-18), 15.5
(C-19), 48.0 (C-20), 183.1 (C-21), 21.7 (C-22), 27.0
(C-23), 124.0 (C-24), 133.4 (C-25), 24.6 (C-26), 17.8
(C-27), 28.1 (C-28), 16.0 (C-29), 25.8 (C-30)。以上数
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据与文献报道一致[10],故鉴定化合物 11 为 3α-羟基
甘遂-8, 24-二烯-21-酸。
化合物 12:无色针晶(丙酮),10%硫酸乙醇
溶液显色为红色。EI-MS m/z: 454 [M]+, 439 [M-
CH3], 421 [M-CH3-H2O], 393, 297, 159, 133, 119
(100)。1H-NMR (300 MHz, CDCl3) δ: 0.82 (3H, s), 0.90
(3H, s), 1.03 (3H, s), 1.05 (3H, s), 1.10 (3H, s), 1.59 (3H,
s), 1.68 (3H, s), 5.09 (1H, t, J = 6.6 Hz, H-24);13C-NMR
(75 MHz, CDCl3) δ: 35.6 (C-1), 34.5 (C-2), 217.7 (C-3),
47.3 (C-4), 51.5 (C-5), 20.1 (C-6), 25.9 (C-7), 133.2 (C-8),
134.4 (C-9), 37.1 (C-10), 21.4 (C-11), 29.3 (C-12), 43.9
(C-13), 49.7 (C-14), 27.4 (C-15), 28.7 (C-16), 46.9 (C-17),
15.8 (C-18), 19.6 (C-19), 47.6 (C-20), 182.8 (C-21), 32.4
(C-22), 26.8 (C-23), 123.6 (C-24), 132.7 (C-25), 17.6
(C-26), 25.7 (C-27), 24.2 (C-28), 21.2 (C-29), 26.8
(C-30)。以上数据与文献报道一致[11],故鉴定化合
物 12 为榄香酮酸。
化合物 13:白色无定形粉末(丙酮),易溶于
氯仿,10%硫酸乙醇溶液显色为红色。1H-NMR (300
MHz, CDCl3) δ: 0.75 (3H, s), 0.90 (3H, s), 0.91 (3H,
s), 0.93 (3H, s), 0.97 (3H, s), 1.58 (3H, s), 1.71 (3H,
s), 3.49 (1H, br s, H-3), 5.09 (1H, br s, H-7), 5.25 (1H,
br s, H-24);13C-NMR (75 MHz, CDCl3) δ: 31.2 (C-1),
25.3 (C-2), 76.5 (C-3), 37.3 (C-4), 44.5 (C-5), 23.9
(C-6), 118.2 (C-7), 145.7 (C-8), 48.3 (C-9), 34.8
(C-10), 17.5 (C-11), 33.4 (C-12), 43.3 (C-13), 51.0
(C-14), 33.9 (C-15), 29.7 (C-16), 47.1 (C-17), 12.9
(C-18), 21.8 (C-19), 49.7 (C-20), 181.4 (C-21), 32.4
(C-22), 27.0 (C-23), 123.6 (C-24), 132.2 (C-25), 17.7
(C-26), 25.7 (C-27), 27.8 (C-28), 21.8 (C-29), 27.3
(C-30)。以上数据与文献报道一致[12],故鉴定化合
物 13 为 3α-羟基甘遂-7, 24-二烯-21-酸。
化合物 14:白色无定形粉末(甲醇),10%硫
酸乙醇溶液显色为红色。EI-MS m/z: 310, 299, 256,
239, 134, 98, 57, 43。1H-NMR (CDCl3) δ: 0.88 (3H,
J = 7.2 Hz, CH3), 1.25 (br s, CH2×12), 1.63 (2H, t,
J = 6.9 Hz, H-3′), 2.35 (2H, t, J = 7.5 Hz, H-2′), 3.59
(1H, dd, J = 12.0, 5.7 Hz, H-3), 3.70 (1H, dd, J = 12.0,
3.9 Hz, H-3), 3.93 (1H, m, H-2), 4.14 (1H, dd, J =
12.0, 6.2 Hz, H-1), 4.20 (1H, dd, J = 12.0, 5.0 Hz,
H-1)。以上数据与文献报道一致[13],故鉴定该化合
物 14 为 α-棕榈酸甘油酯。
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