(±)-Emodin bianthrone   中文名称: 反式-大黄素二蒽酮

Natural product

从土壤真菌Hamigera avellana BCC 17816中分离出两种新型环丙基二酮hamavellone A（1）和B（2），两种新型14元非酮大内酯hamigeromycin A（3）和B。通过NMR和MS数据分析确定了新化合物的结构。3的绝对立体化学是通过与5的化学相关性来解决的。Hamavellone B（2）表现出抗疟疾活性，IC50为5.2μg/mL，同时也表现出相当的细胞毒性[1]。

使用微培养放射性同位素技术对恶性疟原虫（K1，耐多药菌株）的活性进行测定。17使用绿色荧光蛋白微板测定（GFPMA）对结核分枝杆菌H37Ra的生长抑制活性和对Vero细胞（非洲绿猴肾成纤维细胞）的细胞毒性进行测定。18使用雷沙苏林微板测定评估对白色念珠菌的抗真菌活性和对KB细胞（口腔人类表皮样癌）、MCF7细胞（人类癌症）和NCI-H187细胞（人类小细胞肺癌）的抗癌活性[1]。

[1]. Novel cyclopropyl diketones and 14-membered macrolides from the soil fungus Hamigera avellanea BCC 17816. Tetrahedron. 2008; 64(49): 11028-11033.

(10S)-1,3,8-trihydroxy-6-methyl-10-[(9S)-2,4,5-trihydroxy-7-methyl-10-oxo-9H-anthracen-9-yl]-10H-anthracen-9-one has been reported in Rhamnus prinoides with data available.

---

Pseurotin A (6) was first described from Pseudeurotium ovalis S2269/F,3a and it has been isolated from various fungi such as Aspergillus species4, 12 and Pochonia chlamydosporia var. catenulata.13 Emodin (7) and its hydroxy analogue 8 are commonly occurring as constituents of plants and fungi. Emodin bianthrones (9 and 10) and structurally related bianthrones have been known as constituents of plants.5, 6, 6(a), 6(b), 6(c) To the best of our knowledge, this is the first report of the isolation of 9 and 10 as fungal secondary metabolites. There have been only a few other reports on the new metabolites of Hamigera species, such as the cyclopentapeptides, avellanins A and B from H. avellanea14 and their analogues PF1171A–PF1171E from H. avellanea PF1171,15 and polyketide metabolites, hamigerone and dihydrohamigerone from H. avellanea NN005492.16, 16(a), 16(b) In the present study four different chemical classes of polyketide metabolites, comprising 10 compounds, have been isolated from H. avellanea BCC 17816, demonstrating that fungi in this genus are potent sources of bioactive compounds. All isolated compounds were subjected to our in vitro biological protocols, inclusive of antimalarial (Plasmodium falciparum K1), antitubercular (Mycobacterium tuberculosis H37Ra), and antifungal (Candida albicans) activities, and cytotoxicity against three human cancer cell-lines (KB, MCF7, and NCI-H187 cells) and noncancerous Vero cells (Table 3). Hamavellone B (2) exhibited moderate antimalarial activity, while it also showed cytotoxic activities. Among 14-membered macrolides, only compound 5 exhibited moderate cytotoxicity, and no other biological activities were shown in this class of compounds. It should be noted that emodin bianthrones (9 and 10) strongly inhibited the proliferation of the malarial parasite, although they showed comparable cytotoxicity to Vero cells.[1]

C30H22O8

510.49

61281-20-7

12096290

Typically exists as solid at room temperature

1.585±0.06 g/cm3(Predicted)

773.7±60.0 °C(Predicted)

5.8

156 Ų

6

8

1

38

865

2

C1(C2(c3c([H])c(O[H])c([H])c(O[H])c3C(=O)c3c(c(c(c([H])c23)C([H])([H])[H])[H])O[H])[H])(c2c([H])c(O[H])c([H])c(O[H])c2C(=O)c2c(c(c(c([H])c12)C([H])([H])[H])[H])O[H])[H]

UUXPVUHOWQPCSC-ZEQRLZLVSA-N

InChI=1S/C30H22O8/c1-11-3-15-23(17-7-13(31)9-21(35)27(17)29(37)25(15)19(33)5-11)24-16-4-12(2)6-20(34)26(16)30(38)28-18(24)8-14(32)10-22(28)36/h3-10,23-24,31-36H,1-2H3/t23-,24-/m0/s1

(10S)-1,3,8-trihydroxy-6-methyl-10-[(9S)-2,4,5-trihydroxy-7-methyl-10-oxo-9H-anthracen-9-yl]-10H-anthracen-9-one

Trans-Emodin bianthrone; ( inverted exclamation markA)-Emodin bianthrone; CHEMBL464711;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

注意: 如下所列的是一些常用的体内动物实验溶解配方，主要用于溶解难溶或不溶于水的产品（水溶度<1 mg/mL）。 建议您先取少量样品进行尝试，如该配方可行，再根据实验需求增加样品量。

---

注射用配方1: DMSO : Tween 80： Saline = 10 : 5 : 85 (如： 100 μL DMSO → 50 μL Tween 80 → 850 μL Saline)
*生理盐水/Saline的制备：将0.9g氯化钠/NaCl溶解在100 mL ddH ₂ O中，得到澄清溶液。
注射用配方 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL DMSO → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)
注射用配方 3: DMSO : Corn oil = 10 : 90 (如： 100 μL DMSO → 900 μL Corn oil)
示例: 以注射用配方 3 (DMSO : Corn oil = 10 : 90) 为例说明, 如果要配制 1 mL 2.5 mg/mL的工作液, 您可以取 100 μL 25 mg/mL 澄清的 DMSO 储备液，加到 900 μL Corn oil/玉米油中, 混合均匀。

View More

注射用配方 4: DMSO : 20% SBE-β-CD in Saline = 10 : 90 [如：100 μL DMSO → 900 μL (20% SBE-β-CD in Saline)]
*20% SBE-β-CD in Saline的制备（4°C，储存1周）：将2g SBE-β-CD (磺丁基-β-环糊精) 溶解于10mL生理盐水中，得到澄清溶液。
注射用配方 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (如： 500 μL 2-Hydroxypropyl-β-cyclodextrin (羟丙基环胡精)→ 500 μL Saline)
注射用配方 6: DMSO : PEG300 : Castor oil : Saline = 5 : 10 : 20 : 65 (如： 50 μL DMSO → 100 μL PEG300 → 200 μL Castor oil → 650 μL Saline)
注射用配方 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (如： 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
注射用配方 8: 溶解于Cremophor/Ethanol (50 : 50), 然后用生理盐水稀释。
注射用配方 9: EtOH : Corn oil = 10 : 90 (如： 100 μL EtOH → 900 μL Corn oil)
注射用配方 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL EtOH → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)

---

口服配方 1: 悬浮于0.5% CMC Na (羧甲基纤维素钠)
口服配方 2: 悬浮于0.5% Carboxymethyl cellulose (羧甲基纤维素)
示例: 以口服配方 1 (悬浮于 0.5% CMC Na)为例说明, 如果要配制 100 mL 2.5 mg/mL 的工作液, 您可以先取0.5g CMC Na并将其溶解于100mL ddH2O中，得到0.5%CMC-Na澄清溶液；然后将250 mg待测化合物加到100 mL前述 0.5%CMC Na溶液中，得到悬浮液。

View More

口服配方 3: 溶解于 PEG400 (聚乙二醇400)
口服配方 4: 悬浮于0.2% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 5: 溶解于0.25% Tween 80 and 0.5% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 6: 做成粉末与食物混合

---

注意: 以上为较为常见方法，仅供参考， InvivoChem并未独立验证这些配方的准确性。具体溶剂的选择首先应参照文献已报道溶解方法、配方或剂型，对于某些尚未有文献报道溶解方法的化合物，需通过前期实验来确定（建议先取少量样品进行尝试），包括产品的溶解情况、梯度设置、动物的耐受性等。

---

请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。