Dendrobine
(Synonyms: 石斛碱) 目录号 : GC38120
A sesquiterpenoid with anticancer activity
Cas No.:2115-91-5
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
Dendrobine is a sesquiterpenoid that has been found in D. nobile and has anticancer activity.1,2 It decreases viability of A549 cells when used at concentrations ranging from 2.5 to 15 ?g/ml.2 It induces apoptosis in A549 cells when used at concentrations ranging from 1 to 10 ?g/ml, as well as increases JNK phosphorylation and sensitizes A549 cells to cisplatin at 10 ?g/ml. Dendrobine (50 mg/kg per day) reduces tumor growth in an A549 mouse xenograft model with an additive effect when used in combination with cisplatin.
1.Meng, C.-W., He, Y.-L., Peng, C., et al.Picrotoxane sesquiterpenoids from the stems of Dendrobium nobile and their absolute configurations and angiogenesis effectFitoterapia121206-211(2017) 2.Song, T.-H., Chen, X.-X., Lee, C.K.-F., et al.Dendrobine targeting JNK stress signaling to sensitize chemotoxicity of cisplatin against non-small cell lung cancer cells in vitro and in vivoPhytomedicine5318-27(2019)
| Cas No. | 2115-91-5 | SDF | |
| 别名 | 石斛碱 | ||
| Canonical SMILES | O=C1O[C@]2([H])[C@@H](C(C)C)[C@@]1([H])[C@@](CC3)([H])[C@]4(C)[C@@]3([H])CN(C)[C@]24[H] | ||
| 分子式 | C16H25NO2 | 分子量 | 263.38 |
| 溶解度 | DMSO : 33.33 mg/mL (126.55 mM; Need ultrasonic) | 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 | 3.7968 mL | 18.984 mL | 37.968 mL |
| 5 mM | 0.7594 mL | 3.7968 mL | 7.5936 mL |
| 10 mM | 0.3797 mL | 1.8984 mL | 3.7968 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。
Dendrobine attenuates osteoclast differentiation through modulating ROS/NFATc1/ MMP9 pathway and prevents inflammatory bone destruction
Phytomedicine 2022 Feb;96:153838.PMID:34801352DOI:10.1016/j.phymed.2021.153838.
Background: Osteolytic diseases share symptoms such as bone loss, fracture and pain, which are caused by over-activated osteoclasts. Targeting osteoclast differentiation has emerged as a therapeutic strategy clinically. Dendrobine is an alkaloid isolated from Chinese herb Dendrobium nobile, with knowing effects of analgesia and anti-inflammation. The roles of Dendrobine on osteoclasts and osteolysis remain unclear. Purpose: Herein, the possible roles of Dendrobine in osteoclastogenesis, inflammatory osteolysis and the underlying mechanism were explored. Methods: Bone marrow-derived macrophages (BMMs) and RAW264.7 cells were employed to evaluate the roles of Dendrobine on osteoclastogenesis, bone absorption and the underlying mechanism in vitro. LPS injection was used to cause inflammatory osteolysis in vivo. Results: Dendrobine repressed osteoclastogenesis, bone resorption induced by receptor activator of nuclear factor kappa B ligand (RANKL) in vitro. Mechanistically, Dendrobine inhibited RANKL-upregulated intracellular (ROS), p-p38, c-Fos expression and nuclear factor of activated T cells (NFATc1) nuclear translocation. Osteoclastic genes were reduced, and among them matrix metalloproteinase 9 (MMP9) mRNA was dramatically blocked by Dendrobine. Moreover, it substantially suppressed MMP9 protein expression during osteoclastogenesis in vitro. Accordingly, oral 20 mg/kg/day Dendrobine was capable of preventing LPS-induced osteolysis with decreased osteoclasts in vivo. Conclusion: Taken together, Dendrobine suppresses osteoclastogenesis through restraining ROS, p38-c-Fos and NFATc1-MMP9 in vitro, thus attenuates inflammatory osteolysis in vivo. This finding supports the discover of Dendrobine as a novel osteoclast inhibitor for impeding bone erosion in the future.
Dendrobine-type alkaloids from Dendrobium nobile
Nat Prod Res 2022 Nov;36(21):5393-5399.PMID:34930072DOI:10.1080/14786419.2021.2019731.
Six dendrobine-type alkaloids were isolated from the tubes of Dendrobium nobile by silica gel, Sephadex LH-20 gel column chromatography, and preparative HPLC. Compound 1 is a new alkaloid containing a pair of amide tautomers, whereas compound 2 is a new dendrobine-type alkaloid. By using spectroscopic techniques including 1 D and 2 D NMR, the structures of compounds 1‒6 were identified as N-methoxylcarbonyldendrobine (1), dendronboic acid (2), Dendrobine (3), 6-hydroxyldendrobine (4), Dendrobine N-oxide (5), and denrine (6). The cytotoxic effects of the isolated compounds on two human tumour cell lines (HCT-116 and SW1990) were evaluated using MTT assay.
Transcriptome Analysis of Dendrobine Biosynthesis in Trichoderma longibrachiatum MD33
Front Microbiol 2022 Aug 1;13:890733.PMID:35979500DOI:10.3389/fmicb.2022.890733.
Dendrobine is a representative component of Dendrobium nobile, and its pharmacological effects have been extensively studied. Trichoderma longibrachiatum MD33 was isolated from the stem of Dendrobium nobile which can produce Dendrobine. In order to understand the effect of Methyl Jasmonate (MeJA) on the production of Dendrobine, transcriptome analysis was performed after MeJA treatment in the MD33 and control groups. The Dendrobine production of MeJA (20 μmol/L) treatment group was 44.6% higher than that of control. In this study, the RNA sequencing technology was applied, a total of 444 differentially expressed genes (DEGs) in the control and MeJA treatment groups, including 226 up-regulated genes and 218 down-regulated genes. The Kyoto Encyclopedia of Genes and Genomes annotation showed that numbers of DEGs were associated with the putative alkaloid biosynthetic pathway in T Trichoderma longibrachiatum MD33. Several MVA pathway enzyme-coding genes (isopentenyl-diphosphate Delta-isomerase, iphosphomevalonate decarboxylase and farnesyl diphosphate synthase) were found to be differentially expressed, suggesting an active precursor supply for alkaloid biosynthesis after MeJA treatment, in other wise, Dendrobine may synthesis through the MVA pathway in MD33. Numerous MeJA-induced P450 family genes, aminotransferase genes and methyltransferase genes were identified, providing several important candidates to further elucidate the Dendrobine biosynthetic pathway of T. longibrachiatum MD33. Furthermore, several MeJA-induced transcription factors (TFs) encoding genes were identified, suggesting a complex genetic network affecting the Dendrobine in T. longibrachiatum MD33. These findings reveal the regulation mechanism underlying the MeJA-induced accumulation of Dendrobine in T. longibrachiatum MD33.
Dendrobine modulates autophagy to alleviate ox-LDL-induced oxidative stress and senescence in HUVECs
Drug Dev Res 2022 Aug;83(5):1125-1137.PMID:35417048DOI:10.1002/ddr.21937.
Dendrobine has potential advantages in suppressing atherosclerosis (AS). FK506-binding protein 1A (FKBP1A) is implicated in the regulation of autophagy, inflammation, and apoptosis. To reveal the mechanism by which Dendrobine inhibits AS by modulating autophagy, oxidative stress, apoptosis, and senescence. An in vitro AS cell model was induced by culturing human umbilical vein endothelial cells (HUVECs) with oxidized low-density lipoprotein (ox-LDL). The cells were treated with Dendrobine alone or in combination with short hairpin RNA (shRNA) targeting FKBP1A or together with 3-methyladenine (3MA), an autophagy inhibitor. Inflammatory cytokines levels tumor necrosis factor-α, interleukin-6 (IL-6), and IL-1β were analyzed and oxidative stress levels were detected by the analysis of reactive oxygen species, malondialdehyde, and superoxide dismutase levels, followed by the analysis of apoptosis levels through terminal deoxynucleotidyl transferase dUTP nick end labeling staining. Cell senescence was evaluated by senescence-associated β-galactosidase and light chain 3 (LC3) levels were detected by immunofluorescence (IF) staining. The targeting relationship of Dendrobine and FKBP1A was predicted by SwissTarget, PyMol, Autodock, and Open Babel software. Dendrobine reduced the levels of proinflammation factors, oxidative stress levels, apoptosis levels, and senescence phenotype in ox-LDL-induced HUVECs. Besides, cell viability has an opposite change. Furthermore, there was an increase in LC3 IF tensity, and LC3-II/I and Beclin1 expressions, and a decrease in p62 expression. However, these effects of Dendrobine could be markedly destroyed by shRNA silencing FKBP1A and 3MA. Dendrobine can suppress inflammatory responses, oxidative stress, apoptosis, and senescence via FKBP1A-involved autophagy ox-LDL-treated HUVECs.
Recent advances and new insights in biosynthesis of Dendrobine and sesquiterpenes
Appl Microbiol Biotechnol 2021 Sep;105(18):6597-6606.PMID:34463801DOI:10.1007/s00253-021-11534-1.
Sesquiterpenes are one of the most diverse groups of secondary metabolites that have mainly been observed in terpenoids. It is a natural terpene containing 15 carbon atoms in the molecule and three isoprene units with chain, ring, and other skeleton structures. Sesquiterpenes have been shown to display multiple biological activities such as anti-inflammatory, anti-feedant, anti-microbial, anti-tumor, anti-malarial, and immunomodulatory properties; therefore, their therapeutic effects are essential. In order to overcome the problem of low-yielding sesquiterpene content in natural plants, regulating their biosynthetic pathways has become the focus of many researchers. In plant and microbial systems, many genetic engineering strategies have been used to elucidate biosynthetic pathways and high-level production of sesquiterpenes. Here, we will introduce the research progress and prospects of the biosynthesis of artemisinin, costunolide, parthenolide, and Dendrobine. Furthermore, we explore the biosynthesis of Dendrobine by evaluating whether the biosynthetic strategies of these sesquiterpene compounds can be applied to the formation of Dendrobine and its intermediate compounds. KEY POINTS: • The development of synthetic biology has promoted the study of terpenoid metabolism and provided an engineering platform for the production of high-value terpenoid products. • Some possible intermediate compounds of Dendrobine were screened out and the possible pathway of Dendrobine biosynthesis was speculated. • The possible methods of Dendrobine biosynthesis were explored and speculated.