Terphenyllin
(Synonyms: 三联苯曲菌素) 目录号 : GC34835
A fungal metabolite with antibacterial properties
Cas No.:52452-60-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Terphenyllin is a flavonoid metabolite originally isolated from A. candidus that has antibacterial and cytotoxic properties.1,2 It is active against methicillin-resistant S. aureus 1 (MRSA-1), MRSA-2, and V. vulnificus (MICs = 31.27-31.47 ?g/ml) and cytotoxic to HeLa, A549, and HepG2 cells (IC50s = 18.87, 12.33, and 21.2 ?M, respectively).2 Terphenyllin inhibits HIV-1 integrase in coupled and strand transfer assays with IC50 values of 17.7 ?M and 47.7 ?M.3
1.Marchelli, R., and Vining, L.C.Terphenyllin, a novel p-terphenyl metabolite from aspergillus candidusJ. Antibiot. (Tokyo)28(4)328-331(1975) 2.Wang, W., Liao, Y., Tang, C., et al.Cytotoxic and antibacterial compounds from the coral-derived fungus Aspergillus tritici SP2-8-1Mar. Drugs15(11)E348(2017) 3.Singh, S.B., Jayasuriya, H., Dewey, R., et al.Isolation, structure, and HIV-1-integrase inhibitory activity of structurally diverse fungal metabolitesJ. Ind. Microbiol. Biotechnol.30(12)721-731(2003)
| Cas No. | 52452-60-5 | SDF | |
| 别名 | 三联苯曲菌素 | ||
| Canonical SMILES | OC1=CC=C(C=C1)C2=C(C(O)=C(C(OC)=C2)C3=CC=C(C=C3)O)OC | ||
| 分子式 | C20H18O5 | 分子量 | 338.35 |
| 溶解度 | DMSO : 83.33 mg/mL (246.28 mM) | 储存条件 | Store at -20°C |
| 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 | 2.9555 mL | 14.7776 mL | 29.5552 mL |
| 5 mM | 0.5911 mL | 2.9555 mL | 5.911 mL |
| 10 mM | 0.2956 mL | 1.4778 mL | 2.9555 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。
Terphenyllin Suppresses Orthotopic Pancreatic Tumor Growth and Prevents Metastasis in Mice
Front Pharmacol 2020 Apr 8;11:457.PMID:32322210DOI:10.3389/fphar.2020.00457.
Pancreatic cancer (PC) is an aggressive and fatal disease with high incidences of metastasis and recurrence. However, there are no effective treatment options for the majority of PC patients, especially for those with locally advanced tumors and metastatic diseases. Therefore, it is urgently needed to develop safe and effective anti-PC therapeutic agents. We have recently identified a novel marine-derived natural product Terphenyllin with potent anti-PC activity. The present study was designed to investigate the efficacy and mechanisms of action of Terphenyllin in several human PC cell lines and an orthotopic PC mouse model. The results showed that Terphenyllin significantly inhibited the viability of all PC cell lines with minimal effects on a normal human pancreatic cell line (HPNE). We next demonstrated the effects of Terphenyllin on colony formation, apoptosis, migration, and invasion in both Panc1 and HPAC cell lines in a concentration-dependent manner. Terphenyllin also suppressed the tumor growth and metastasis in the Panc1 orthotopic mouse model. We further showed the profound effects of Terphenyllin on the expression of apoptosis-associated proteins, including Bax, Bad, Puma, BimL, Bcl-2, phos-Bcl-2 (Ser70), Bcl-xL, caspase 7, and PARP, which contributed to its anti-PC activity. In summary, Terphenyllin suppressed the PC cell growth and metastasis in vitro and in vivo and may be developed as an anti-PC therapeutic agent in the future.
Inhibition of STAT3 Signaling Pathway by Terphenyllin Suppresses Growth and Metastasis of Gastric Cancer
Front Pharmacol 2022 Mar 25;13:870367.PMID:35401187DOI:10.3389/fphar.2022.870367.
Gastric cancer is a common type of malignant tumor with a relatively poor prognosis and presents a serious threat to global health. Signal Transducer and Activator of Transcription-3 (STAT3) has been strongly implicated in many cancers, and its constitutive activation promotes growth, angiogenesis, inflammation, and immune evasion. Therefore, considerable efforts have been put into developing effective and safe STAT3 inhibitors. In this study, we performed a virtual screening by molecular docking and found that Terphenyllin, a marine-derived natural product, directly interacted with STAT3. We further found that Terphenyllin inhibited the phosphorylation and activation of STAT3 and decreased the protein levels of STAT3-dependent target genes, including c-Myc and Cyclin D1. Subsequently, we demonstrated that Terphenyllin exerted its potent anticancer efficacy against gastric cancer in vitro and in vivo. Terphenyllin concentration-dependently inhibited growth, proliferation, and colony formation and induced cell cycle arrest and apoptosis of gastric cancer cells in vitro. Moreover, Terphenyllin treatment suppressed the tumor growth and metastasis in a gastric cancer orthotopic mouse model without notable toxicity in vivo. Taken together, our results indicated that Terphenyllin exerts its anticancer activity by inhibiting the STAT3 signaling pathway and may serve as a potent STAT3 inhibitor for gastric cancer treatment.
Structure-Activity Relationships and Potent Cytotoxic Activities of Terphenyllin Derivatives from a Small Compound Library
Chem Biodivers 2020 Jul;17(7):e2000207.PMID:32367656DOI:10.1002/cbdv.202000207.
A small library of 120 compounds was established with seventy new alkylated derivatives of the natural product Terphenyllin, together with 45 previous reported derivatives and four natural p-terphenyl analogs. The 70 new derivatives were semi-synthesized and evaluated for cytotoxic activities against four cancer cell lines. Interestingly, 2',4''-diethoxyterphenyllin, 2',4,4''-triisopropoxyterphenyllin, and 2',4''-bis(cyclopentyloxy)Terphenyllin showed potent activities with IC50 values in a range from 0.13 to 5.51 μM, which were similar to those of the positive control, adriamycin. The preliminary structure-activity relationships indicated that the introduction of alkyl substituents including ethyl, allyl, propargyl, isopropyl, bromopropyl, isopentenyl, cyclopropylmethyl, and cyclopentylmethyl are important for improving the cytotoxicity.
A new p-terphenyl derivative from the insect-derived fungus Aspergillus candidus Bdf-2 and the synergistic effects of Terphenyllin
PeerJ 2020 Jan 2;8:e8221.PMID:31915570DOI:10.7717/peerj.8221.
A new p-terphenyl derivative 4″-deoxy-2'-methoxyterphenyllin (1), along with six known p-terphenyl derivatives (2-7), a known flavonoid derivative dechlorochlorflavonin (8) and a known fellutanine A (9), were isolated from the insect-derived strain of the fungus Aspergillus candidus Bdf-2, associated with Blaptica dubia. The structure of 1 was established by the analysis of the 1D and 2D NMR and HR-ESI-MS spectra. Compounds 1-9 were evaluated for antibacterial activities against Staphylococcus aureus ATCC29213, Escherichia coli ATCC25922 and Ralstonia solanacearum, and for antioxidant activities. Synergistic effects of compound 2 with the other compounds were also investigated. As a result, compound 6 displayed the best antibacterial activities in all single compound with MIC value of 32 µg/mL against S. aureus ATCC29213 and R. solanacearum, respectively. However, no antibacterial effect against E. coli ATCC25922 was detected from any single compound. The combination of 2 + 6 exhibited obvious synergistic effect against S. aureus ATCC29213 and the MIC value was 4 µg/mL. Compound 6 also showed the best antioxidant activity as a single compound with an IC50 value of 17.62 µg/mL. Combinations of 5 + 6, 2 + 4 + 5 and 2 + 4 + 5 + 6 displayed synergistic effect and their antioxidant activities were better than that of any single compound.
Anti-inflammatory and anticancer p-terphenyl derivatives from fungi of the genus Thelephora
Bioorg Med Chem 2022 Sep 15;70:116935.PMID:35901638DOI:10.1016/j.bmc.2022.116935.
Fungi from the genus Thelephora have been exploited to identify bioactive compounds. The main natural products characterized are para-terphenyl derivatives, chiefly represented by the lead anti-inflammatory compound vialinin A isolated from species T. vialis and T. terrestris. Different series of p-terphenyls have been identified, including vialinins, ganbajunins, terrestrins, telephantins and other products. Their mechanism of action is not always clearly identified, and different potential molecule targets have been proposed. The lead vialinin A functions as a protease inhibitor, efficiently targeting ubiquitin-specific peptidases USP4/5 and sentrin-specific protease SENP1 which are prominent anti-inflammatory and anticancer targets. Protease inhibition is coupled with a powerful inhibition of the cellular production of tumor necrosis factor TNFα. Other mechanisms contributing to the anti-inflammatory or anti-proliferative action of these p-terphenyl compounds have been invoked, including the formation of cytotoxic copper complexes for derivatives bearing a catechol central unit such vialinin A, terrestrin B and telephantin O. These p-terphenyl compounds could be further exploited to design novel anticancer agents, as evidenced with the parent compound Terphenyllin (essentially found in Aspergillus species) which has revealed marked antitumor and anti-metastatic effects in xenograft models of gastric and pancreatic cancer. This review shed light on the structural and functional diversity of p-terphenyls compounds isolated from Thelephora species, their molecular targets and pharmacological properties.