Dicentrine
(Synonyms: 荷苞牡丹碱) 目录号 : GC38527
Dicentrine 是从 Lindera megaphylla 中分离出的一种天然产物，具有降压作用。Dicentrine 是 α1- 肾上腺素能受体拮抗剂，对人类增生的前列腺有效。
Cas No.:517-66-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Dicentrine is a natural product isolated from the plant Lindera megaphylla with antihypertensive effect. Dicentrine is an α1-adrenoceptor antagonist which has effective against human hyperplastic prostates[1].
[1]. Sheu-Meei Yu, et al. Effects of dicentrine, a novel α1-adrenoceptor antagonist, on human hyperplastic prostates. European Journal of Pharmacology. 1994 Jan; 252(1):29-34.
| Cas No. | 517-66-8 | SDF | |
| 别名 | 荷苞牡丹碱 | ||
| Canonical SMILES | CN1[C@]2([H])C3=C(C4=C(OCO4)C=C3CC1)C5=C(C=C(OC)C(OC)=C5)C2 | ||
| 分子式 | C20H21NO4 | 分子量 | 339.39 |
| 溶解度 | Soluble in DMSO | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.9465 mL | 14.7323 mL | 29.4646 mL |
| 5 mM | 0.5893 mL | 2.9465 mL | 5.8929 mL |
| 10 mM | 0.2946 mL | 1.4732 mL | 2.9465 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Dicentrine Potentiates TNF-α-Induced Apoptosis and Suppresses Invasion of A549 Lung Adenocarcinoma Cells via Modulation of NF-κB and AP-1 Activation
Molecules 2019 Nov 13;24(22):4100.PMID:31766230DOI:10.3390/molecules24224100.
Numerous studies have indicated that tumor necrosis factor-alpha (TNF-α) could induce cancer cell survival and metastasis via activation of transcriptional activity of NF-κB and AP-1. Therefore, the inhibition of TNF-α-induced NF-κB and AP-1 activity has been considered in the search for drugs that could effectively treat cancer. Dicentrine, an aporphinic alkaloid, exerts anti-inflammatory and anticancer activities. Therefore, we investigated the effects of Dicentrine on TNF-α-induced tumor progression in A549 lung adenocarcinoma cells. Our results demonstrated that Dicentrine effectively sensitizes TNF-α-induced apoptosis in A549 cells when compared with Dicentrine alone. In addition, Dicentrine increases caspase-8, -9, -3, and poly (ADP-ribose) polymerase (PARP) activities by upregulating the death-inducing signaling complex and by inhibiting the expression of antiapoptotic proteins including cIAP2, cFLIP, and Bcl-XL. Furthermore, Dicentrine inhibits the TNF-α-induced A549 cells invasion and migration. This inhibition is correlated with the suppression of invasive proteins in the presence of Dicentrine. Moreover, Dicentrine significantly blockes TNF-α-activated TAK1, p38, JNK, and Akt, leading to reduced levels of the transcriptional activity of NF-κB and AP-1. Taken together, our results suggest that Dicentrine could enhance TNF-α-induced A549 cell death by inducing apoptosis and reducing cell invasion due to, at least in part, the suppression of TAK-1, MAPK, Akt, AP-1, and NF-κB signaling pathways.
Dicentrine production from a hairy roots culture of Stephania suberosa
Z Naturforsch C J Biosci 2009 Sep-Oct;64(9-10):692-6.PMID:19957438DOI:10.1515/znc-2009-9-1014.
A hairy roots culture of Stephania suberosa was established using Agrobacterium rhizogenes ATCC15834. The production of Dicentrine was found to be (8.92 +/- 0.07) mg/g dry wt on day 35 of culture. Effects of sucrose content, tyrosine, and medium strength on growth and Dicentrine production of S. suberosa were investigated. 6% (w/v) sucrose was an optimum content for the growth and Dicentrine accumulation in S. suberosa hairy roots. The utilization of a precursor from tyrosine feeding enhanced the Dicentrine production. The medium with 1.0 mM of tyrosine had the highest effect on Dicentrine accumulation in hairy roots at day 40 of culture [(14.73 +/- 0.47) mg/g dry wt]. In addition, 1/4 Murashige and Skoog medium was suitable for biomass and Dicentrine production in hairy roots. This culture system has a potential to produce Dicentrine from hairy roots of S. suberosa.
Dicentrine Analogue-Induced G2/M Arrest and Apoptosis through Inhibition of Topoisomerase II Activity in Human Cancer Cells
Planta Med 2015 Jul;81(10):830-7.PMID:26158522DOI:10.1055/s-0035-1546128.
Lindera megaphylla has been traditionally used as an antineoplastic and wound healing remedy. We previously demonstrated the antitumor effects of D-dicentrine, a natural aporphine alkaloid from the root of L. megaphylla. To generate analogues, series of phenanthrene alkaloids from D-dicentrine were synthesized by degradation with ethyl chloroformate in pyridine, base hydrolysis, and N-alkylation. In this study, we demonstrated that one of the synthesized D-dicentrine analogues (here after designated as analogue 1) exhibited more potent cytotoxic effects than D-dicentrine in colon adenocarcinoma, hepatoma, leukemia, and epidermoid carcinoma cells. We performed cell cycle and apoptotic analysis by flow cytometry, an apoptotic DNA detection ELISA assay, and topoisomerase II activity by the kinetoplast DNA concatenation assay for studying their cytotoxic mechanisms. We found that both D-dicentrine and analogue 1 induced apoptosis and G2/M arrest in HL-60 leukemia cells. The percentage of apoptotic cells induced by analogue 1 was 4.5-fold higher than that induced by D-dicentrine as evident from measuring the amount of histone-bound DNA fragments. Moreover, we found that analogue 1 was 28-fold more potent than D-dicentrine for inhibition of topoisomerase II activity by the kinetoplast DNA concatenation assay. Our findings indicate that D-dicentrine analogue 1 is very promising as a potential antitumor agent for future study.
Dicentrine, a novel antiplatelet agent inhibiting thromboxane formation and increasing the cyclic AMP level of rabbit platelets
Biochem Pharmacol 1992 Jan 22;43(2):323-9.PMID:1310852doi
Dicentrine is an antiplatelet agent isolated from the Chinese herb Lindera megaphylla. We examined the in vitro effects of Dicentrine on various aspects of platelet reactivity. Dicentrine inhibited the aggregation and ATP release of washed rabbit platelets induced by arachidonic acid (AA), collagen, ADP, platelet-activating factor (PAF), thrombin and U46619. Dicentrine also inhibited the thromboxane B2 formation caused by AA, collagen and thrombin in washed intact platelets or that induced by AA in lysed platelet homogenate, while prostaglandin D2 formation caused by AA was not increased. The generation of inositol monophosphates (in the presence of indomethacin) caused by thrombin, collagen and PAF was not suppressed significantly, nor did Dicentrine suppress fibrinogen-induced aggregation of elastase-treated platelets. Dicentrine inhibited the intracellular Ca2+ increase in quin-2/AM-loaded platelets caused by thrombin, PAF, collagen and AA. The cyclic AMP level was elevated by Dicentrine in a concentration-dependent manner. These data indicate that the inhibitory effect of Dicentrine on platelet aggregation and ATP release was due to the inhibition of thromboxane formation and the elevation of the level of cyclic AMP.
Dicentrine, an alpha-adrenoceptor antagonist with sodium and potassium channel blocking activities
Naunyn Schmiedebergs Arch Pharmacol 1994 Jan;349(1):42-9.PMID:7908125DOI:10.1007/BF00178204.
To elucidate the electrophysiological effect of Dicentrine, an alkaloid isolated from Lindera megaphylla, we examined action potential and membrane currents in single cardiac cells. The tight-seal whole cell clamp technique was used. In the current clamp condition, 3 microM Dicentrine prolonged rat ventricular action potential duration (APD50) from 38.9 +/- (SEM)9.8 ms to 147.8 +/- 19.7 ms (n = 12) and reduced its maximal rate of depolarization (Vmax) from 220.5 +/- 20.3 V/s to 37.0 +/- 4.0 V/s. The same concentration of quinidine increased APD50 from 42.5 +/- 5.2 ms to 182.8 +/- 15.6 ms (n = 6) and decreased the Vmax from 225.4 +/- 19.5 V/s to 32.2 +/- 3.0 V/s. Voltage clamp study revealed that Dicentrine (1 to 100 microM) inhibited the integral of the transient outward current (Ito-I200) dose-dependently with a KD value of 3.0 +/- 0.5 microM. At 50 mV, the suppression of Ito by 3 microM Dicentrine was accompanied by shortening of its inactivation time constant from 41.0 +/- 4.9 ms to 18.8 +/- 2.1 ms. V0.5 for the steady state inactivation curve of Ito was shifted from -25.5 +/- 2.8 mV to -40.6 +/- 2.1 mV. Compared to Dicentrine, quinidine exerted stronger but the same mode of inhibition of Ito. 4-Aminopyridine, however, blocked Ito without modification of its inactivation time constant. In addition to the inhibition of Ito, the late outward current (Ilo) was significantly reduced by 10 microM each of Dicentrine and quinidine to 60.0 +/- 13.3% and 37.5 +/- 6.3%, respectively. 4-Aminopyridine (2 mM) failed to inhibit this current.(ABSTRACT TRUNCATED AT 250 WORDS)