滇桑、蚕沙化学成分及生物活性的研究
摘要
滇桑(Morus yunnanensis Koidz)为桑科Moraceae,桑属Morus植物,分布于云南西北。桑属植物化学成分及生物活性研究均较为丰富,脂溶性部分以酚性化合物为主,生物活性主要集中在抗高血压,抗病毒,抗菌,抗氧化,抗炎,抗肿瘤等;水溶性部分以多羟基生物碱和氨基酸为主,多羟基生物碱主要具有降血糖活性。
蚕沙(Faeces bombycis)为昆虫家蚕蛾Bobyx mori L幼虫的干燥粪便,记载于《本草纲目》。蚕沙有祛风除湿、清热明目、活血定痛的功能。主治风热目痛、风湿性心脏病、关节炎、肢体麻木、风疹瘙痒、头痛头风等症,在一些治疗糖尿病的复方中经常使用。蚕沙60%乙醇提取物有效部位经我所药理室筛选,表明具有较强抑制α-葡萄糖苷酶活性。
本论文运用色谱和波谱技术并结合化学方法,以生物活性为指标,对上述中药蚕沙及滇桑茎皮进行了系统的化学成分研究,并对其粗提物及单体成分进行了药理活性筛选。
从滇桑Morus yunnanensis Koidz茎皮95%乙醇提取物乙酸乙酯及氯仿洗脱部分共得到47个化合物。这些化合物分别为Yunanensol A(1),Yunanensol B(2),Yunanensin B(3),Yunanensin A(4),Yunanensin C(5),Yunanensin D(6),YunanensinE(7),Kuwanon H(8),Kuwanon G(9),Kuwanon O(10),Sanggenol M(11),Mongolicin F(12),Guangsangon J(13),Mulberrofuran J(14),Guangsangon B(15),Guangsangon L(16),Kuwanon X(17),Kuwanon P(18),Mulberrofuran E(19),Mulberrofuran O(20),Chalcomoracin(21),Mulberrofuran K(22),Sorocein A(23),Mulberrofuran F(24),Kuwanol A(25),Albanol B(26),Mulberrofuran Q(27),Mongolicin C(28),Moracin P(29),Moracin M(30),Mulberroside C(31),AustrafuranC(32),3',5',2,4-tetrahydroxy-4-(3-methyl-1butenyl)Stibene(33),Resveratrol(34),Oxyresveratrol(35),Morachalcone A(36),2',4',7-trihydroxy-(2S)-flavone(37),5,7,2',4'-tetrahydlroxy-3-gerany flavone(38),Norartocarpetin(39),Isolicoflavonol(40),Kaempferol(41),Sitosteryl 3β-glucoside 6'-O-palmitate(42),正丁酸(n-butanoicacid,43),β-daucosterol(44),β-sitosterol(45),Betulinic acid(46),Lupeol(47)。在这些化合物中,Diels-Alder型加合物26个(3-28),二苯乙烯和苯骈呋喃类化合物7个(29-35),黄酮类化合物8个(1,2,36-41),三萜类化合物(46,47)2个及其他化合物4个(42-45)。其中,化合物1,2为新黄酮类化合物,化合物3-7为新Diels-Alder型化合物。
所有47个分离得到的化合物均为首次从滇桑中得到。
从蚕沙(Faeces bombycis)60%乙醇提取物、95%乙醇提取物共得到29个化合物。这些化合物分别为Scopoletin(1),Umbelliferone(2),Esculetin(3),二氢尿嘧啶(Dihydro uracil,4),尿嘧啶(Uracil,5),(6S,9R)-Vomifoliol(6),(6S,9S)-Vomifoliol(7),Loliolide(8),苯甲酸(Benzoic acid,9),9,16-Dioxo-10,12,14-octadecatrienoic acid(10),1-doexynojirimycin(11),Fagomine(12),丙氨酸(Alanine,13),谷氨酸(Glutamic acid,14),甜菜碱(Betaine,15),异亮氨酸(Isoleucine,16),亮氨酸(Leucine,17),苯丙氨酸(Phenylalanine,18),L-哌可啉酸(L-pipecolinic acid,19),3S,5R-dihydroxy-6R,7-megstigmadien-9-one(20),3S,5R-dihydroxy-6S,7-megstigmadien-9-one(21),(6R,9R)-3-Oxo-α-ionolβ-D-glucopyranoside(22),(6R,9S)-3-Oxo-α-ionolβ-D-glucopyranoside(23),BlumenolC glucoside(24),Byzantionoside B(25),Alangionoside L(26),叶黄素(Lutein,27),β-sitosterol(28),β-daucosterol(29)。在这些化合物中,香豆素类化合物3个(1-3),降倍半萜及其苷类化合物10个(6-8,20-26),多羟基生物碱化合物2个(11,12),氨基酸类化合物5个(13,14,16-18),含N类其它化合物4个(4,5,15,19)及其他化合物5个(9,10,16-18)。
在分离得到的化合物中,有21个为首次从蚕沙中得到,分别为化合物1-12,15,20-17。
药理筛选结果:
(1)滇桑茎皮95%乙醇提取物及从中分离得到的单体化合物的活性。
①抗肿瘤活性:采用MTT法,滇桑茎皮95%乙醇提取物的氯仿和乙酸乙酯部分对五种人癌细胞(A549,人肺腺癌细胞;Bel-7402,人肝癌细胞;BGC-823,人胃癌细胞;HCT-8,人结肠癌细胞;A2780,人卵巢癌细胞)表现弱的抗肿瘤活性;20个单体化合物(包括1个新Diels-Alder型加合物),其中8个Dids-Alder型加合物和1个三萜酸对五种癌细胞都具有抑制作用;另外4个Diels-Alder型加合物,4个二苯乙烯和苯骈呋喃类化合物及3个黄酮类化合物显示对部分人癌细胞的抑制作用,IC_(50)在0.092到9.806μg/mL之间。
②抗氧化活性:滇桑茎皮95%乙醇提取物的乙酸乙酯部分显示明显的抗氧化活性;从滇桑乙酸乙酯部分得到的23个酚性成分显示抗氧化活性:其中Diels-Alder型加合物19个(包括4个新化合物),二苯乙烯和苯骈呋喃类化合物3个及1个黄酮类化合物对Fe~(2+)-半胱氨酸诱导的肝微粒体脂质过氧化物的抑制率均大于50%,其中10个化合物的抑制率达到90%以上。
③抗炎活性:10个化合物对PAF刺激的多形核白细胞β葡萄糖苷酸酶释放表现了抑制作用,显示抗炎活性:尤其2个Diels-Alder型加合物与2个黄酮类化合物(包括1个新黄酮类化合物)的抑制率均在90%以上。
(2)蚕沙化合物的抑制α-葡萄糖苷酶活性
通过以体外抑制α-葡萄糖苷酶为指标,对蚕沙60%乙醇提取物的分离过程进行活性追踪,从中发现了2个单体化合物具有较好的降糖活性,为多羟基生物碱类化合物,化合物1-doexynojirimycin与Fagomine,抑制α-葡萄糖苷酶IC_(50)分别为0.014and 1.368μg/mL;对它们进一步进行α-麦芽糖酶、α-蔗糖酶、α-淀粉酶抑制活性的测定;并积累了足够量,进行小鼠体内抗糖尿病活性作用机理的研究,分别进行正常小鼠蔗糖负荷、正常小鼠淀粉负荷、正常小鼠葡萄糖负荷、Alloxan高血糖小鼠蔗糖负荷、Alloxan高血糖小鼠淀粉负荷试验,体内试验结果表明化合物1-doexynojirimycin可抑制小鼠蔗糖或淀粉负荷后血糖水平的增高,但对于葡萄糖负荷后没有抑制作用。机理为它在小肠抑制了α-葡萄糖苷酶,延迟了其将双糖水解为单糖,从而推迟了葡萄糖吸收进入血液。
因此,可以得出结论,化合物1-doexynojirimycin确实是蚕沙的强降糖作用的活性成分。
Morus yunnanensis Koidz belongs to the the genus Morus of the family Moraceae, distributed in the northwest of Yunnan province. Many various bio-components were isolated from the genus Morus: the alcohol soluble part is mainly phenolic compounds which have antihypertension, antivirus, antibacterial, antifungi, antioxidation, anti-inflammation, and anticancer activities; the water soluble compounds are mostly amino acids, and polyhydroxylated alkaloids which have antiglycemia activity.
Faeces bombycis, the larvae of silkworm (Bobyx mon L)'s dried dejecta, are written in Compendium of Materia Medica. According to the theories of traditional Chinese medicine, they are slightly bitter in taste, mild in nature, and attributive to the liver meridian. In traditional Chinese medicine, their pharmacological actions are to expel wind, dredge the meridians, and ease joint pains. And they are often contributed in folk medicine for treatment of diabetes. Our experimental results show that 60% alcohol extract of Faeces bombycis has the effects of anα-glucosidase inhibitor.
By means of chromatographic and spectrographic technologies as well as chemical methods, the two medical materials mentioned above were studied systemically in chemistry and related bioassays.
Forty seven compounds were obtained from 95 % alcohol extract (CH_3COOC_2H_5 and CHCl_3 extract) of the stem bark of M. yunnanensis Koidz. They were identified as follows: Yunanensol A (1), Yunanensol B (2), Yunanensin B (3), Yunanensin A (4), Yunanensin C (5), Yunanensin D (6), Yunanensin E (7), Kuwanon H (8), Kuwanon G (9), Kuwanon O (10), Sanggenol M (11), Mongolicin F (12), Guangsangon J (13), Mulberrofuran J (14), Guangsangon B (15), Guangsangon L (16), Kuwanon X (17), Kuwanon P (18), Mulberrofuran E (19), Mulberrofuran O (20), Chalcomoracin (21), Mulberrofuran K (22), Sorocein A (23), Mulberrofuran F (24), Kuwanol A (25), Albanol B (26), Mulberrofuran Q (27), Mongolicin C (28), Moracin P (29), Moracin M (30), Mulberroside C (31), Austrafuran C (32), 3',5',2,4-tetrahydroxy-4-(3-methyl-lbutenyl) Stibene (33), Resveratrol (34), Oxyresveratrol (35), Morachalcone A (36), 2',4',7-trihydroxy-(2S)-flavone (37), 5,7,2',4'-tetrahydroxy-3-gerany flavone (38), Norartocarpetin (39), Isolicoflavonol (40), Kaempferol (41), Sitosteryl 3β-glucoside 6'-O-palmitate (42), n-butanoic acid (43),β-daucosterol (44),β-sitosterol (45), Betulinic acid (46), Lupeol (47). Among them, compounds 1 and 2 are new flavones, compounds 3-6 were new Diels-Alder adducts, and 7 is a new natural product. And there are twenty-six Diels-Alder adducts (3-28), seven stilbenes (29-35), eight flavones (1, 2, 36-41), two triterpenoids (46,47) and four other compounds (42-45).
Among them, all the forty seven were isolated from the stem bark of M. yunnanensis Koidz for the first time.
Twenty nine compounds were obtained from 60% alcohol extract and 95% alcohol extract of Faeces bombycis. They were identified as follows: Scopoletin (1), Umbelliferone (2), Esculetin (3), Dihydro uracil (4), Uracil (5), (6S,9R)-Vomifoliol (6), (6S,9S)-Vomifoliol (7), Loliolide (8), Benzoic acid (9), 9,16-Dioxo-10,12,14-octadecatrienoic acid (10), 1-doexynojirimycin (11), Fagomine (12), Alanine (13), Glutamic acid (14), Betaine (15), Isoleucine (16), Leucine (17), Phenylalanine (18), L-pipecolinic acid (19),3S,5S-dihydroxy-6R, 7-megstigmadien-9-one (20),3S, 5R-dihydroxy-6S,7-megstigmadien-9-one (21), (6R,9R)-3-Oxo-α-ionolβ-D-glucopyranoside (22), (6R, 9S)-3-Oxo-α-ionolβ-D-glucopyranoside (23), Blumenol C glucoside (24), Byzantionoside B (25), Alangionoside L (26), Lutein (27),β-sitosterol (28),β-daucosterol (29). Among them, there are three coumarins (1-3), ten nor-sesquiterpenoids and glycosides (6-8, 20-26), two polyhydroxylated alkaloids (11, 12), five amino acids (13, 14, 16-18), four containing N compounds (4, 5, 15, 19) and four other compounds (42-45).
Among them, twenty-one compounds (1-12, 15, 20-17) were isolated from Faeces bombycis for the first time.
The results of bioassays displayed:1. (1) By MTT, twenty compounds (including one new Diels-Alder adduct), which were obtained from the 95% ethanol extract of M. yunnanensis Koidz, showed moderate anticancer activity against five human cancer cell lines (A549, Bel-7402, BGC-823, HCT-8, A2780) with IC_(50) ranging from 3.9-9.5μg/mL.
(2) Twenty three phenolic compounds, isolated from the EtOAc soluble part of M. yunnanensis Koidz, inhibited the production of the lipid peroxide induced by Fe~(2+)-Cys system in the liver microsomal obviously, with inhibitory rates more than 50% at a concentration of 10~(-5) mol/L,and even some of them with inhibitory rates more than 90%.
(3) On the pharmacological model of release ofβ-glucuronidase from rat PMNs induced by PAF, ten compounds, isolated from M. yunnanensis Koidz, were revealed the anti-inflammation activity with the inhibitory rates more than 50% at a concentration of 10~(-5) mol/L. Especially two Diels-Alder adducts and two flavones (including one new flavone) revealed the inhibitory rates more than 90%.2. Two known polyhydroxy alkaloids, 1-deoxynojirimycin (11) and fagomine (12), have been isolated from the 60 % ethanol extract of Faeces bombycis by bioassay-guided fractionation using the a-glucosidase inhibitory assay. Compounds 11 and 12 exhibited IC_(50) values (concentration at which 50 % a-glucosidase are inhibited) of 0.014 and 1.368μg/mL,respectively. In the sucrose and starch tolerance tests, administration of 11 resulted in the hypoglycemic effect in normal and alloxan-induced diabetic mice at 9 mg/kg when dosed orally.
The results from present study show that 1-deoxynojirimycin inhibits the rises of plasma glucose levels after sucrose and starch loading in mice, but no effect after glucose loading. The mechanism is that it delays the hydrolization of disaccharide into monosaccharides by inhibiting a-glucosidase on small intestine, thus delays the absorption of glucose into blood. Moreover, our study shows that compounds 11 is a selective disaccharidase inhibitor, therefore it leaves theα-amylase activity nearly unaffected and there would be less subjective symptoms for clinical use.
Referring to the results in vitro it is concluded that compounds 11 is indeed the active principle of Faeces bombycis for their potent hypoglycemic effect.
蚕沙(Faeces bombycis)为昆虫家蚕蛾Bobyx mori L幼虫的干燥粪便,记载于《本草纲目》。蚕沙有祛风除湿、清热明目、活血定痛的功能。主治风热目痛、风湿性心脏病、关节炎、肢体麻木、风疹瘙痒、头痛头风等症,在一些治疗糖尿病的复方中经常使用。蚕沙60%乙醇提取物有效部位经我所药理室筛选,表明具有较强抑制α-葡萄糖苷酶活性。
本论文运用色谱和波谱技术并结合化学方法,以生物活性为指标,对上述中药蚕沙及滇桑茎皮进行了系统的化学成分研究,并对其粗提物及单体成分进行了药理活性筛选。
从滇桑Morus yunnanensis Koidz茎皮95%乙醇提取物乙酸乙酯及氯仿洗脱部分共得到47个化合物。这些化合物分别为Yunanensol A(1),Yunanensol B(2),Yunanensin B(3),Yunanensin A(4),Yunanensin C(5),Yunanensin D(6),YunanensinE(7),Kuwanon H(8),Kuwanon G(9),Kuwanon O(10),Sanggenol M(11),Mongolicin F(12),Guangsangon J(13),Mulberrofuran J(14),Guangsangon B(15),Guangsangon L(16),Kuwanon X(17),Kuwanon P(18),Mulberrofuran E(19),Mulberrofuran O(20),Chalcomoracin(21),Mulberrofuran K(22),Sorocein A(23),Mulberrofuran F(24),Kuwanol A(25),Albanol B(26),Mulberrofuran Q(27),Mongolicin C(28),Moracin P(29),Moracin M(30),Mulberroside C(31),AustrafuranC(32),3',5',2,4-tetrahydroxy-4-(3-methyl-1butenyl)Stibene(33),Resveratrol(34),Oxyresveratrol(35),Morachalcone A(36),2',4',7-trihydroxy-(2S)-flavone(37),5,7,2',4'-tetrahydlroxy-3-gerany flavone(38),Norartocarpetin(39),Isolicoflavonol(40),Kaempferol(41),Sitosteryl 3β-glucoside 6'-O-palmitate(42),正丁酸(n-butanoicacid,43),β-daucosterol(44),β-sitosterol(45),Betulinic acid(46),Lupeol(47)。在这些化合物中,Diels-Alder型加合物26个(3-28),二苯乙烯和苯骈呋喃类化合物7个(29-35),黄酮类化合物8个(1,2,36-41),三萜类化合物(46,47)2个及其他化合物4个(42-45)。其中,化合物1,2为新黄酮类化合物,化合物3-7为新Diels-Alder型化合物。
所有47个分离得到的化合物均为首次从滇桑中得到。
从蚕沙(Faeces bombycis)60%乙醇提取物、95%乙醇提取物共得到29个化合物。这些化合物分别为Scopoletin(1),Umbelliferone(2),Esculetin(3),二氢尿嘧啶(Dihydro uracil,4),尿嘧啶(Uracil,5),(6S,9R)-Vomifoliol(6),(6S,9S)-Vomifoliol(7),Loliolide(8),苯甲酸(Benzoic acid,9),9,16-Dioxo-10,12,14-octadecatrienoic acid(10),1-doexynojirimycin(11),Fagomine(12),丙氨酸(Alanine,13),谷氨酸(Glutamic acid,14),甜菜碱(Betaine,15),异亮氨酸(Isoleucine,16),亮氨酸(Leucine,17),苯丙氨酸(Phenylalanine,18),L-哌可啉酸(L-pipecolinic acid,19),3S,5R-dihydroxy-6R,7-megstigmadien-9-one(20),3S,5R-dihydroxy-6S,7-megstigmadien-9-one(21),(6R,9R)-3-Oxo-α-ionolβ-D-glucopyranoside(22),(6R,9S)-3-Oxo-α-ionolβ-D-glucopyranoside(23),BlumenolC glucoside(24),Byzantionoside B(25),Alangionoside L(26),叶黄素(Lutein,27),β-sitosterol(28),β-daucosterol(29)。在这些化合物中,香豆素类化合物3个(1-3),降倍半萜及其苷类化合物10个(6-8,20-26),多羟基生物碱化合物2个(11,12),氨基酸类化合物5个(13,14,16-18),含N类其它化合物4个(4,5,15,19)及其他化合物5个(9,10,16-18)。
在分离得到的化合物中,有21个为首次从蚕沙中得到,分别为化合物1-12,15,20-17。
药理筛选结果:
(1)滇桑茎皮95%乙醇提取物及从中分离得到的单体化合物的活性。
①抗肿瘤活性:采用MTT法,滇桑茎皮95%乙醇提取物的氯仿和乙酸乙酯部分对五种人癌细胞(A549,人肺腺癌细胞;Bel-7402,人肝癌细胞;BGC-823,人胃癌细胞;HCT-8,人结肠癌细胞;A2780,人卵巢癌细胞)表现弱的抗肿瘤活性;20个单体化合物(包括1个新Diels-Alder型加合物),其中8个Dids-Alder型加合物和1个三萜酸对五种癌细胞都具有抑制作用;另外4个Diels-Alder型加合物,4个二苯乙烯和苯骈呋喃类化合物及3个黄酮类化合物显示对部分人癌细胞的抑制作用,IC_(50)在0.092到9.806μg/mL之间。
②抗氧化活性:滇桑茎皮95%乙醇提取物的乙酸乙酯部分显示明显的抗氧化活性;从滇桑乙酸乙酯部分得到的23个酚性成分显示抗氧化活性:其中Diels-Alder型加合物19个(包括4个新化合物),二苯乙烯和苯骈呋喃类化合物3个及1个黄酮类化合物对Fe~(2+)-半胱氨酸诱导的肝微粒体脂质过氧化物的抑制率均大于50%,其中10个化合物的抑制率达到90%以上。
③抗炎活性:10个化合物对PAF刺激的多形核白细胞β葡萄糖苷酸酶释放表现了抑制作用,显示抗炎活性:尤其2个Diels-Alder型加合物与2个黄酮类化合物(包括1个新黄酮类化合物)的抑制率均在90%以上。
(2)蚕沙化合物的抑制α-葡萄糖苷酶活性
通过以体外抑制α-葡萄糖苷酶为指标,对蚕沙60%乙醇提取物的分离过程进行活性追踪,从中发现了2个单体化合物具有较好的降糖活性,为多羟基生物碱类化合物,化合物1-doexynojirimycin与Fagomine,抑制α-葡萄糖苷酶IC_(50)分别为0.014and 1.368μg/mL;对它们进一步进行α-麦芽糖酶、α-蔗糖酶、α-淀粉酶抑制活性的测定;并积累了足够量,进行小鼠体内抗糖尿病活性作用机理的研究,分别进行正常小鼠蔗糖负荷、正常小鼠淀粉负荷、正常小鼠葡萄糖负荷、Alloxan高血糖小鼠蔗糖负荷、Alloxan高血糖小鼠淀粉负荷试验,体内试验结果表明化合物1-doexynojirimycin可抑制小鼠蔗糖或淀粉负荷后血糖水平的增高,但对于葡萄糖负荷后没有抑制作用。机理为它在小肠抑制了α-葡萄糖苷酶,延迟了其将双糖水解为单糖,从而推迟了葡萄糖吸收进入血液。
因此,可以得出结论,化合物1-doexynojirimycin确实是蚕沙的强降糖作用的活性成分。
Morus yunnanensis Koidz belongs to the the genus Morus of the family Moraceae, distributed in the northwest of Yunnan province. Many various bio-components were isolated from the genus Morus: the alcohol soluble part is mainly phenolic compounds which have antihypertension, antivirus, antibacterial, antifungi, antioxidation, anti-inflammation, and anticancer activities; the water soluble compounds are mostly amino acids, and polyhydroxylated alkaloids which have antiglycemia activity.
Faeces bombycis, the larvae of silkworm (Bobyx mon L)'s dried dejecta, are written in Compendium of Materia Medica. According to the theories of traditional Chinese medicine, they are slightly bitter in taste, mild in nature, and attributive to the liver meridian. In traditional Chinese medicine, their pharmacological actions are to expel wind, dredge the meridians, and ease joint pains. And they are often contributed in folk medicine for treatment of diabetes. Our experimental results show that 60% alcohol extract of Faeces bombycis has the effects of anα-glucosidase inhibitor.
By means of chromatographic and spectrographic technologies as well as chemical methods, the two medical materials mentioned above were studied systemically in chemistry and related bioassays.
Forty seven compounds were obtained from 95 % alcohol extract (CH_3COOC_2H_5 and CHCl_3 extract) of the stem bark of M. yunnanensis Koidz. They were identified as follows: Yunanensol A (1), Yunanensol B (2), Yunanensin B (3), Yunanensin A (4), Yunanensin C (5), Yunanensin D (6), Yunanensin E (7), Kuwanon H (8), Kuwanon G (9), Kuwanon O (10), Sanggenol M (11), Mongolicin F (12), Guangsangon J (13), Mulberrofuran J (14), Guangsangon B (15), Guangsangon L (16), Kuwanon X (17), Kuwanon P (18), Mulberrofuran E (19), Mulberrofuran O (20), Chalcomoracin (21), Mulberrofuran K (22), Sorocein A (23), Mulberrofuran F (24), Kuwanol A (25), Albanol B (26), Mulberrofuran Q (27), Mongolicin C (28), Moracin P (29), Moracin M (30), Mulberroside C (31), Austrafuran C (32), 3',5',2,4-tetrahydroxy-4-(3-methyl-lbutenyl) Stibene (33), Resveratrol (34), Oxyresveratrol (35), Morachalcone A (36), 2',4',7-trihydroxy-(2S)-flavone (37), 5,7,2',4'-tetrahydroxy-3-gerany flavone (38), Norartocarpetin (39), Isolicoflavonol (40), Kaempferol (41), Sitosteryl 3β-glucoside 6'-O-palmitate (42), n-butanoic acid (43),β-daucosterol (44),β-sitosterol (45), Betulinic acid (46), Lupeol (47). Among them, compounds 1 and 2 are new flavones, compounds 3-6 were new Diels-Alder adducts, and 7 is a new natural product. And there are twenty-six Diels-Alder adducts (3-28), seven stilbenes (29-35), eight flavones (1, 2, 36-41), two triterpenoids (46,47) and four other compounds (42-45).
Among them, all the forty seven were isolated from the stem bark of M. yunnanensis Koidz for the first time.
Twenty nine compounds were obtained from 60% alcohol extract and 95% alcohol extract of Faeces bombycis. They were identified as follows: Scopoletin (1), Umbelliferone (2), Esculetin (3), Dihydro uracil (4), Uracil (5), (6S,9R)-Vomifoliol (6), (6S,9S)-Vomifoliol (7), Loliolide (8), Benzoic acid (9), 9,16-Dioxo-10,12,14-octadecatrienoic acid (10), 1-doexynojirimycin (11), Fagomine (12), Alanine (13), Glutamic acid (14), Betaine (15), Isoleucine (16), Leucine (17), Phenylalanine (18), L-pipecolinic acid (19),3S,5S-dihydroxy-6R, 7-megstigmadien-9-one (20),3S, 5R-dihydroxy-6S,7-megstigmadien-9-one (21), (6R,9R)-3-Oxo-α-ionolβ-D-glucopyranoside (22), (6R, 9S)-3-Oxo-α-ionolβ-D-glucopyranoside (23), Blumenol C glucoside (24), Byzantionoside B (25), Alangionoside L (26), Lutein (27),β-sitosterol (28),β-daucosterol (29). Among them, there are three coumarins (1-3), ten nor-sesquiterpenoids and glycosides (6-8, 20-26), two polyhydroxylated alkaloids (11, 12), five amino acids (13, 14, 16-18), four containing N compounds (4, 5, 15, 19) and four other compounds (42-45).
Among them, twenty-one compounds (1-12, 15, 20-17) were isolated from Faeces bombycis for the first time.
The results of bioassays displayed:1. (1) By MTT, twenty compounds (including one new Diels-Alder adduct), which were obtained from the 95% ethanol extract of M. yunnanensis Koidz, showed moderate anticancer activity against five human cancer cell lines (A549, Bel-7402, BGC-823, HCT-8, A2780) with IC_(50) ranging from 3.9-9.5μg/mL.
(2) Twenty three phenolic compounds, isolated from the EtOAc soluble part of M. yunnanensis Koidz, inhibited the production of the lipid peroxide induced by Fe~(2+)-Cys system in the liver microsomal obviously, with inhibitory rates more than 50% at a concentration of 10~(-5) mol/L,and even some of them with inhibitory rates more than 90%.
(3) On the pharmacological model of release ofβ-glucuronidase from rat PMNs induced by PAF, ten compounds, isolated from M. yunnanensis Koidz, were revealed the anti-inflammation activity with the inhibitory rates more than 50% at a concentration of 10~(-5) mol/L. Especially two Diels-Alder adducts and two flavones (including one new flavone) revealed the inhibitory rates more than 90%.2. Two known polyhydroxy alkaloids, 1-deoxynojirimycin (11) and fagomine (12), have been isolated from the 60 % ethanol extract of Faeces bombycis by bioassay-guided fractionation using the a-glucosidase inhibitory assay. Compounds 11 and 12 exhibited IC_(50) values (concentration at which 50 % a-glucosidase are inhibited) of 0.014 and 1.368μg/mL,respectively. In the sucrose and starch tolerance tests, administration of 11 resulted in the hypoglycemic effect in normal and alloxan-induced diabetic mice at 9 mg/kg when dosed orally.
The results from present study show that 1-deoxynojirimycin inhibits the rises of plasma glucose levels after sucrose and starch loading in mice, but no effect after glucose loading. The mechanism is that it delays the hydrolization of disaccharide into monosaccharides by inhibiting a-glucosidase on small intestine, thus delays the absorption of glucose into blood. Moreover, our study shows that compounds 11 is a selective disaccharidase inhibitor, therefore it leaves theα-amylase activity nearly unaffected and there would be less subjective symptoms for clinical use.
Referring to the results in vitro it is concluded that compounds 11 is indeed the active principle of Faeces bombycis for their potent hypoglycemic effect.
引文
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