Podocarpic acid
(Synonyms: 罗汉松酸) 目录号 : GC33675
Podocarpicacid是一种天然产物，为TRPA1的激活剂，具有多种功效。
Cas No.:5947-49-9
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
Podocarpic acid is a natural product, which has the best all-round positive effect and acts as a novel TRPA1 activator.
Podocarpic acid anhydride acts as a 1 nM agonist of LXRalpha and beta receptors. It shows over 8-10-fold better activator of LXR receptors compared to one of the natural ligands, 22-(R)-hydroxy cholesterol, in HEK-293 cells[2].
Podocarpic acid activates SKN-1 in C. elegans, similar to known Nrf2 activators such as α-lipoic acid (LA). Podocarpic acid- or LA-induced SKN-1 activation also requires TRPodocarpic acid-1: trPodocarpic acid-1 knockdown in glod-4;gst-4p::gfp animals reduces expression of gst-4 to wild-type levels. A and LA supplementation results in a robust Ca2+ flux, which is significantly reduces when the Ca2+-impermeable TRPodocarpic acid-1E1018A channel is present, suggesting that TRPodocarpic acid-1 activation is key for these drugs' function. Finally, Podocarpic acid and LA alleviate the Podocarpic acidthogenic phenotypes of glod-4 animals by reverting the high endogenous MGO and GO to almost wild-type-like levels[1].
[1]. Baraka HN. Microbial transformation of podocarpic acid and evaluation of transformation products for antioxidant activity. Planta Med. 2010 May;76(8):815-7. [2]. Singh S, et al. Discovery and development of dimeric podocarpic acid leads as potent agonists of liver X receptor with HDL cholesterol raising activity in mice and hamsters. Bioorg Med Chem Lett. 2005 Jun 2;15(11):2824-8.
| Cas No. | 5947-49-9 | SDF | |
| 别名 | 罗汉松酸 | ||
| Canonical SMILES | O=C([C@@]1(C)CCC[C@]2(C)C3=C(CC[C@@]12[H])C=CC(O)=C3)O | ||
| 分子式 | C17H22O3 | 分子量 | 274.35 |
| 溶解度 | DMSO: ≥ 100 mg/mL (364.50 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 | 3.645 mL | 18.2249 mL | 36.4498 mL |
| 5 mM | 0.729 mL | 3.645 mL | 7.29 mL |
| 10 mM | 0.3645 mL | 1.8225 mL | 3.645 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。
Valorisation of the diterpene Podocarpic acid - Antibiotic and antibiotic enhancing activities of polyamine conjugates
Bioorg Med Chem 2022 Jun 15;64:116762.PMID:35477062DOI:10.1016/j.bmc.2022.116762.
As part of our search for new antimicrobials and antibiotic adjuvants, a series of podocarpic acid-polyamine conjugates have been synthesized. The library of compounds made use of the phenolic and carboxylic acid moieties of the diterpene allowing attachment of polyamines (PA) of different lengths to afford a structurally-diverse set of analogues. Evaluation of the conjugates for intrinsic antimicrobial properties identified two derivatives of interest: a PA3-4-3 (spermine) amide-bonded variant 7a that was a non-cytotoxic, non-hemolytic potent growth inhibitor of Gram-positive Staphylococcus aureus (MRSA) and 9d, a PA3-8-3 carbamate derivative that was a non-toxic selective antifungal towards Cryptococcus neoformans. Of the compound set, only one example exhibited activity towards Gram-negative bacteria. However, in the presence of sub-therapeutic amounts of either doxycycline (4.5 µM) or erythromycin (2.7 μM) several analogues were observed to exhibit weak to modest antibiotic adjuvant properties against Pseudomonas aeruginosa and/or Escherichia coli. The observation of strong cytotoxicity and/or hemolytic properties for subsets of the library, in particular those analogues bearing methyl ester or n-pentylamide functionality, highlighted the fine balance of structural requirements and lipophilicity for antimicrobial activity as opposed to mammalian cell toxicity.
Microbial transformation of Podocarpic acid and evaluation of transformation products for antioxidant activity
Planta Med 2010 May;76(8):815-7.PMID:20072957DOI:10.1055/s-0029-1240738.
Podocarpic acid was metabolized by Mucor ramannianus ATCC 9628, and Beauveria bassiana ATCC 7159 to afford two new metabolites, 2 alpha-hydroxy Podocarpic acid and 11-hydroxy Podocarpic acid, along with the known metabolite 13-hydroxy podocarbic acid. The identity of these metabolites was verified using different spectral methods. The antioxidant activity of the metabolites was tested, and comparable results to those observed for ascorbic acid were obtained.
A review on chemistry, source and therapeutic potential of lambertianic acid
Z Naturforsch C J Biosci 2021 Apr 8;76(9-10):347-356.PMID:33826808DOI:10.1515/znc-2020-0267.
Lambertianic acid (LA) is a diterpene bioactive compound mainly purified from different species of Pinus. It is an optical isomer of another natural compound daniellic acid and was firstly purified from Pinus lambertiana. LA can be synthesized in laboratory from Podocarpic acid. It has been reported to have potential health benefits in attenuating obesity, allergies and different cancers including breast, liver, lung and prostate cancer. It exhibits anticancer properties through inhibiting cancer cell proliferation and survival, and inducing apoptosis, targeting major signalling components including AKT, AMPK, NFkB, COX-2, STAT3, etc. Most of the studies with LA were done using in vitro models, thus warranting future investigations with animal models to evaluate its pharmacological effects such as antidiabetic, anti-inflammatory and neuroprotective effects as well as to explore the underlying molecular mechanisms and toxicological profile. This review describes the chemistry, source, purification and therapeutic potentials of LA and it can therefore be a suitable guideline for any future study with LA.
Investigation of the antitumor activity of Podocarpic acid derivatives
J Pharm Sci 1984 May;73(5):694-6.PMID:6737247DOI:10.1002/jps.2600730528.
As a class, octahydrophenanthrene lactones, podolactones , and related Podocarpic acid derivatives have been reported to possess a wide variety of biological activities, including antileukemic activity, inhibition of plant cell growth, and hormonal and anti-inflammatory properties. In the present study, a series of synthetic intermediates derived from Podocarpic acid have been prepared and evaluated with respect to their ability to inhibit human epidermoid carcinoma of the nasopharynx in vitro. The significant cytotoxicity demonstrated by methyl 6 alpha-bromo-7-oxo-O- methylpodocarpate (50% inhibition of cells at 8.85 X 10(-9) M) was markedly higher than that of the other derivatives examined. Further evaluation against L1210 and P388 lymphoid leukemias in mice failed to demonstrate significant antitumor activity.
Design, synthesis, and structure-activity relationship of Podocarpic acid amides as liver X receptor agonists for potential treatment of atherosclerosis
Bioorg Med Chem Lett 2005 Oct 15;15(20):4574-8.PMID:16125384DOI:10.1016/j.bmcl.2005.06.100.
A series of Podocarpic acid amides were identified as potent agonists for Liver X receptor alpha and beta subtypes, which are members of a nuclear hormone receptor superfamily that are involved in the regulation of a variety of metabolic pathways including cholesterol metabolism. We recently reported Podocarpic acid anhydride and imide dimers as potent LXR agonists. Through parallel organic synthesis, we rapidly identified a series of new podocarpate leads with stable structures exemplified by adamantyl- and phenylcyclohexylmethyl-podocarpic acid amides (14 and 18). Compound 18 exhibited LXRalpha/beta 50/20 nM (binding affinity) and 33.7/35.3-fold receptor inductions. Synthesis, SAR, and biological activities of new podocarpate analogs are discussed.