CN102267884B - 化合物及其在制备抗肿瘤药物中的应用 - Google Patents
化合物及其在制备抗肿瘤药物中的应用 Download PDFInfo
- Publication number
- CN102267884B CN102267884B CN2011101486282A CN201110148628A CN102267884B CN 102267884 B CN102267884 B CN 102267884B CN 2011101486282 A CN2011101486282 A CN 2011101486282A CN 201110148628 A CN201110148628 A CN 201110148628A CN 102267884 B CN102267884 B CN 102267884B
- Authority
- CN
- China
- Prior art keywords
- compound
- chondrosterin
- antitumor
- medicaments
- application
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title abstract description 10
- 239000003814 drug Substances 0.000 title abstract description 10
- 230000000259 anti-tumor effect Effects 0.000 title abstract description 8
- 238000002360 preparation method Methods 0.000 title abstract description 4
- CJYQFZYTBTVSGC-NWANDNLSSA-N (3aS,3bS,6aS)-6a-hydroxy-3a,5,5-trimethyl-3-methylidene-3b,4,6,7-tetrahydrocyclopenta[a]pentalen-2-one Chemical compound O=C1C(=C)[C@@]2(C)[C@@H]3CC(C)(C)C[C@]3(O)CC2=C1 CJYQFZYTBTVSGC-NWANDNLSSA-N 0.000 claims abstract description 24
- 239000000243 solution Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 239000002775 capsule Substances 0.000 claims abstract description 3
- 239000000839 emulsion Substances 0.000 claims abstract description 3
- 238000009472 formulation Methods 0.000 claims abstract description 3
- 238000002347 injection Methods 0.000 claims abstract description 3
- 239000007924 injection Substances 0.000 claims abstract description 3
- 239000006187 pill Substances 0.000 claims abstract description 3
- 239000003826 tablet Substances 0.000 claims abstract description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 14
- 239000002246 antineoplastic agent Substances 0.000 claims description 5
- 229940041181 antineoplastic drug Drugs 0.000 claims description 5
- 230000000118 anti-neoplastic effect Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000375 suspending agent Substances 0.000 claims description 2
- 210000004881 tumor cell Anatomy 0.000 abstract description 7
- 210000004027 cell Anatomy 0.000 abstract description 6
- 206010009944 Colon cancer Diseases 0.000 abstract description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 abstract description 4
- 206010061306 Nasopharyngeal cancer Diseases 0.000 abstract description 4
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 201000005202 lung cancer Diseases 0.000 abstract description 4
- 208000020816 lung neoplasm Diseases 0.000 abstract description 4
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 230000003013 cytotoxicity Effects 0.000 abstract description 2
- 231100000135 cytotoxicity Toxicity 0.000 abstract description 2
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 abstract 1
- 208000029742 colonic neoplasm Diseases 0.000 abstract 1
- 238000007918 intramuscular administration Methods 0.000 abstract 1
- 238000001990 intravenous administration Methods 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 238000013271 transdermal drug delivery Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000855 fermentation Methods 0.000 description 6
- 230000004151 fermentation Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 244000061456 Solanum tuberosum Species 0.000 description 5
- 235000002595 Solanum tuberosum Nutrition 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 239000002207 metabolite Substances 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 3
- 208000002454 Nasopharyngeal Carcinoma Diseases 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 201000010989 colorectal carcinoma Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 201000011216 nasopharynx carcinoma Diseases 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 2
- 241000124001 Alcyonacea Species 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 241000512743 Sarcophyton <anthozoan> Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 229940115088 sea soft Drugs 0.000 description 2
- 238000011218 seed culture Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 102000029749 Microtubule Human genes 0.000 description 1
- 108091022875 Microtubule Proteins 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 101710183280 Topoisomerase Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000007541 cellular toxicity Effects 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229930004610 hirsutane Natural products 0.000 description 1
- 125000000869 hirsutane group Chemical group 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
本发明公开了化合物ChondrosterinA及其在制备抗肿瘤药物中的应用。本发明研究发现化合物ChondrosterinA对多种肿瘤细胞系显示出强效的细胞毒性,如:对肺癌(A549)、鼻咽癌(CNE2)和结肠癌(Lovo)3种肿瘤细胞的IC50值分别为2.452,4.963,5.49μM。表明ChondrosterinA可用于制备抗肿瘤药物,可与其他药物制成抗肿瘤药物组合物,可与药学可以接受的辅料制成注射剂、片剂、丸剂、胶囊剂、溶液、悬浮剂和乳剂等剂型;其给药途径可为经口服、静脉、肌肉或皮肤给药。
Description
技术领域
本发明涉及化合物Chondrosterin A的新用途。
背景技术
恶性肿瘤是一种严重危害人类生命健康的常见病,已成为仅次于心脑血管病的第二位死因,而且肿瘤发病率还在逐年增加。寻找和开发高效低毒的抗肿瘤药物仍然是目前攻克肿瘤的主要途径。
海洋真菌,资源丰富,它们适应了高盐低营养的海洋环境,有独特的代谢途径和遗传背景,也为人类提供了大量的陆地微生物所不能提供的活性代谢产物。近二十年来,从海洋真菌的代谢产物中分离得到了一大批新结构的化合物,结构类型有萜类、醚类、大环内酯类、生物碱类、肽类、酰胺类以及醌类等,有些具有强效抗肿瘤活性化合物,抗肿瘤机制有作用于DNA、微管、拓扑异构酶以及其他酶,作用于细胞通路诱导肿瘤细胞凋亡,诱导免疫反应或是通过改变机体内环境酸碱平衡从而抑制癌细胞生长等,这些活性物质药用前景明显,部分化合物还进入了临床前或临床试验。
我们近年开展了南海软珊瑚的共附生真菌及其活性物质研究,发现软珊瑚共附生真菌的菌株资源非常丰富,而且从中发现活性物质的几率很高。倍半萜类化合物Chondrosterin A是南海扭曲肉芝软珊瑚Sarcophyton tortuosum中分离得到的真菌Chondrostereum sp.经发酵培养产生的。化合物Chondrosterin A是新化合物,其抗肿瘤活性未见报道。
发明内容
本发明的目的在于提供一种海洋真菌新的代谢产物Chondrosterin A。
本发明所述的化合物Chondrosterin A,是具有hirsutane骨架结构的、新的倍半萜化合物,是海洋真菌Chondrostereum sp.的一个主要代谢产物。
Chondrosterin A的结构式为:
(Ⅰ)
本发明的化合物Chondrosterin A 可以从真菌,例如南海海洋软珊瑚Sarcophyton tortuosum的内生真菌Chondrostereum sp.的培养液中提取分离而得到。
本发明化合物Chondrosterin A由真菌Chondrostereum sp.发酵制备方法包括以下步骤:
a. 海洋真菌Chondrostereum sp.的种子培养:
选用PDA (potato dextro se agar) 培养基,其培养基组成为:马铃薯 200 g,葡萄糖 20 g,琼脂 20 g,海水 1 L;制成试管斜面,挑取菌株接入斜面,25-28℃培养5-7天;
b. 海洋真菌Chondrostereum sp.的发酵培养:
发酵培养基成分配比按重量比为:马铃薯 50-500,葡萄糖5-40,酵母提取物0.5-5,蛋白胨1-10,粗海盐2-50,水1000;将斜面中培养好的菌株挑入发酵培养基,于室温25-30℃静置10-40天;
c. 将上述培养好的发酵液过滤,滤除菌体,收集发酵液;
d. 发酵液用乙酸乙酯提取,合并提取液,浓缩得到总提取物;
e. 用乙酸乙酯溶解提取物,溶解物在硅胶柱中进行色谱分离,以石油醚-乙酸乙酯-甲醇梯度淋洗;
f. 收集石油醚-乙酸乙酯(2:1)得到的洗脱组分,经高效液相色谱,以乙腈-水(60:40)纯化得到化合物Chondrosterin A。
本发明研究发现化合物Chondrosterin A对多种肿瘤细胞系显示出强效的细胞毒性,如:对肺癌(A549)、鼻咽癌(CNE2)和结肠癌(Lovo)3种肿瘤细胞的IC50值分别为2.452,4.963,5.49 μM。表明化合物Chondrosterin A可用于制备抗肿瘤药物,可与其他药物制成抗肿瘤药物组合物,可与药学可以接受的辅料制成注射剂、片剂、丸剂、胶囊剂、溶液、悬浮剂和乳剂等剂型;其给药途径可为经口服、静脉、肌肉或皮肤给药。
具体实施方式
下面结合实施例对本发明作进一步说明。
实施例1:化合物Chondrosterin A的制备
a. 海洋真菌Chondrostereum sp.的种子培养:
菌种以PDA为培养基,组成为:马铃薯 200 g的水煮液,葡萄糖 10 g,琼脂 20 g,水 1 L。制成试管斜面,挑取菌株接入斜面,25-28℃培养7天后于4℃保存。
b. 海洋真菌Chondrostereum sp.的发酵培养:
发酵培养基组成为:马铃薯 200 g的水煮液,葡萄糖 10 g,粗海盐23 g,水1 L;将斜面中培养好的菌株挑入发酵培养基,于室温25-28℃静置培养30天;
c. 将上述培养好的发酵液过滤,滤除菌体,收集培养液;
d. 培养液用体积比为1:1的乙酸乙酯萃取3次,合并提取液,40℃水浴旋转蒸发浓缩得到总提取物;
e. 用乙酸乙酯溶解提取物,溶解物在硅胶柱中进行色谱分离,以石油醚-乙酸乙酯-甲醇梯度淋洗;
f. 收集由石油醚-乙酸乙酯(2:1)洗脱得到的组分,蒸除溶剂后,经高效液相色谱,以乙腈-水(60:40)纯化得到无色透明油状化合物Chondrosterin A。
化合物Chondrosterin A的试验数据:
元素分析(w %, C15H20O2):C 77.58,H 8.75,O 13.82,N 0.000;计算值:C, 77.55; H, 8.68; O, 13.77。[α]20 D = +112.5° (c = 0.024,MeOH)。UV nm (MeOH) λmax (log ε):249 (4.06)。IR υ/cm-1 (KBr):3433, 2951, 2867, 1693, 1622, 1462, 1377, 1312, 1259, 1211, 1156, 1123, 1037, 941, 864, 649, 570。LR EI MS: m/z 232, 217, 206, 199, 189, 176, 171, 165, 161, 147, 133, 122 (100%), 115, 111, 107, 91, 77, 69, 55。NMR实验数据如表1所示。
Chondrosterin A的结构与碳的位置编号
表1 Chondrosterin A的NMR数据(1H, 500MHz, 13C, 125MHz; CDCl3, TMS)
实施例2:化合物Chondrosterin A的抗肿瘤活性试验
a. 细胞株:肺癌(A549)、鼻咽癌(CNE2)和结肠癌(Lovo)3种肿瘤细胞。
b.取对数生长的上述肿瘤细胞株加入96孔板中,每孔200 μL含有3000-8000个细胞。
c.再加入药物,设8个药物浓度梯度,分别为0.06、0.025、0.098、0.391、1.563、6.25、25、100 μM,另设DMSO溶剂对照组。
d.每组设5个平行孔,置37℃培养72小时。实验终止前4小时加入10 μL 5 mg/mL MTT液,再培养4小时,弃去培养液,加入0.1 mL DMSO。
e.待结晶溶解后在酶联检测仪上双波长(570 nm,655 nm)检测每孔的OD值。按下列公式求出生长抑制率,再按BLISS法计算机程序求出半数抑制率〔IC50值〕,实验结果见表2。
细胞生长抑制率=(1-用药组平均OD值/对照组孔OD值)×100%
表2 化合物Chondrosterin A的细胞毒性试验结果
肺癌(A549) | 鼻咽癌(CNE2) | 结肠癌(Lovo) | |
半数抑制率IC50 (μM) | 2.452 | 4.963 | 5.49 |
Claims (4)
1.化合物Chondrosterin A,其结构式如式(Ⅰ)所示:
(Ⅰ)。
2.一种抗肿瘤药物组合物,其特征在于含有权利要求1所述Chondrosterin A。
3.权利要求1所述化合物Chondrosterin A在制备抗肿瘤药物中的应用。
4.如权利要求3所述的应用,其特征在于所述抗肿瘤药物的剂型为注射剂、 片剂、丸剂、胶囊剂、溶液、悬浮剂或乳剂。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2011101486282A CN102267884B (zh) | 2011-06-03 | 2011-06-03 | 化合物及其在制备抗肿瘤药物中的应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2011101486282A CN102267884B (zh) | 2011-06-03 | 2011-06-03 | 化合物及其在制备抗肿瘤药物中的应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102267884A CN102267884A (zh) | 2011-12-07 |
CN102267884B true CN102267884B (zh) | 2013-12-11 |
Family
ID=45050367
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2011101486282A Expired - Fee Related CN102267884B (zh) | 2011-06-03 | 2011-06-03 | 化合物及其在制备抗肿瘤药物中的应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102267884B (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103724184B (zh) * | 2013-12-10 | 2015-06-10 | 中山大学 | 一种抗肿瘤化合物Chondrosterin J及其制备方法与应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101491511A (zh) * | 2009-03-03 | 2009-07-29 | 中山大学 | Hirsutanols A在制备抗肿瘤药物中的应用 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5746973A (en) * | 1980-09-04 | 1982-03-17 | Mitsubishi Yuka Yakuhin Kk | Preparation of (+-)-coriolin |
-
2011
- 2011-06-03 CN CN2011101486282A patent/CN102267884B/zh not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101491511A (zh) * | 2009-03-03 | 2009-07-29 | 中山大学 | Hirsutanols A在制备抗肿瘤药物中的应用 |
Non-Patent Citations (3)
Title |
---|
Feng Geng et al.,.Three-Component Coupling via the Squarate Ester Cascade as a Concise Route to the Bioactive Triquinane Sesquiterpene Hypnophilin.《organic letters》.2001,第4卷(第1期),71-73. |
JP昭57-46973A 1982.03.17 |
Three-Component Coupling via the Squarate Ester Cascade as a Concise Route to the Bioactive Triquinane Sesquiterpene Hypnophilin;Feng Geng et al.,;《organic letters》;20011214;第4卷(第1期);71-73 * |
Also Published As
Publication number | Publication date |
---|---|
CN102267884A (zh) | 2011-12-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104825500B (zh) | 白肉灵芝提取物、提取方法及其用途 | |
CN106008502B (zh) | 马齿苋中骨架生物碱化合物及其提取分离方法 | |
CN102516344B (zh) | 一种具有抗肿瘤活性的化合物及其制备方法和应用 | |
CN103087031A (zh) | 双四氢苯并吡喃酮二聚体类化合物在抗癌药物中的应用 | |
CN101463058A (zh) | 羊毛脂烷型三萜化合物海莲酸、其衍生物及其制备方法和用途 | |
CN102267884B (zh) | 化合物及其在制备抗肿瘤药物中的应用 | |
CN106083556B (zh) | 马齿苋中甘菊蓝结构化合物及其提取分离方法 | |
CN102908340B (zh) | 一种含异甘草黄酮醇的抗肿瘤药物及其应用 | |
CN103787953A (zh) | 化合物Aspochalasin V及其制备方法和应用 | |
CN104557841B (zh) | 两个色酮类化合物及其制备方法和在制备抗肿瘤药物中的应用 | |
CN106220587B (zh) | 马齿苋中两种生物碱化合物及其提取分离方法 | |
CN109942658A (zh) | 一类杂萜化合物及其制备方法与应用和抗肿瘤的药物 | |
CN103833823A (zh) | 二萜二聚体类化合物及其药物组合物和制备方法与应用 | |
CN107224432B (zh) | 化合物Stemphol在制备抗肿瘤药物中的应用 | |
CN106810551A (zh) | 两种新碳架生物碱化合物及其提取分离方法 | |
CN101491511B (zh) | Hirsutanols A在制备抗肿瘤药物中的应用 | |
CN107119087B (zh) | 一种细胞松弛素类化合物Aspochalasin D的制备方法及应用 | |
CN105085221B (zh) | 具有抗真菌和抗肿瘤活性的化合物及其制备方法与应用 | |
CN103724184B (zh) | 一种抗肿瘤化合物Chondrosterin J及其制备方法与应用 | |
CN105418725B (zh) | 五环三萜类化合物及其应用 | |
CN109575089B (zh) | 酰化葡萄糖类化合物及其药物组合物和制备方法与应用 | |
CN102618448B (zh) | 补身烷型倍半萜环己烯酮衍生物、其制备方法及用途 | |
CN102440985A (zh) | 双酮类化合物flbg-1108或者其药用盐在制备抗癌药物中的应用 | |
CN109867657B (zh) | 二羟二苯并[b,f][1,5]二氧杂辛环类化合物、制备方法及其药用组合物和应用 | |
CN108047043B (zh) | 分离自香茶菜属植物的化合物及其应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20131211 Termination date: 20190603 |
|
CF01 | Termination of patent right due to non-payment of annual fee |