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Aspterric Acid

目录号 : GC40676

A plant growth regulator

Aspterric Acid Chemical Structure

Cas No.:67309-95-9

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产品描述

Aspterric acid is a carotene-type sesquiterpene, plant growth regulator, and inhibitor of pollen development originally isolated from the fungus A. terreus.[1] [2]  It inhibits pollen development, reduces stem length at first flowering, and increases the time to bolting and first flowering in A. thaliana when used at a concentration of 38 μM. Aspterric acid exerts its effects on reproductive growth in A. thaliana without inhibiting biosynthesis and transport of the plant growth regulator indole-3-acetic acid .[2]

Reference:
[1]. Shimada, A., Kusano, M., Takeuchi, S., et al. Aspterric acid and 6-hydroxymellein, inhibitors of pollen development in Arabidopsis thaliana, produced by Aspergillus terreus. Z. Naturforsch. C. 57(5-6), 459-464 (2002).
[2]. Shimada, A., Yamane, H., and Kimura, Y. The role of aspterric acid in auxin-regulated reproductive growth of Arabidopsis thaliana. Z. Naturforsch. C. 63(7-8), 554-556 (2008).

Chemical Properties

Cas No. 67309-95-9 SDF
化学名 (3R,4R,6aS,9aS)-octahydro-4-hydroxy-7-(1-methylethylidene)-1H-3,9a-methanocyclopent[c]oxocin-4-carboxylic acid
Canonical SMILES OC([C@]1(O)[C@@H](C2)OC[C@]2(CC/C3=C(C)/C)[C@@]3([H])CC1)=O
分子式 C15H22O4 分子量 266.3
溶解度 DMSO: Soluble,Methanol: Soluble 储存条件 Store at -20°C
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1 mM 3.7552 mL 18.7758 mL 37.5516 mL
5 mM 0.751 mL 3.7552 mL 7.5103 mL
10 mM 0.3755 mL 1.8776 mL 3.7552 mL
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Research Update

Artemether and Aspterric Acid induce pancreatic alpha cells to transdifferentiate into beta cells in zebrafish

Br J Pharmacol 2022 May;179(9):1962-1977.PMID:34871457DOI:10.1111/bph.15769.

Background and purpose: Recently, the antimalarial drug, artemether and the neurotransmitter GABA were identified to convert alpha cells into beta-like cells in vivo. However, some of these observations were challenged by other studies. To help address the controversy, we took advantage of zebrafish as a model to perform this study. Experimental approach: First, we performed a small-molecule screening for artemether and its skeleton analogues. Second, we used the Cre-LoxP system for lineage tracing to indicate the conversion of alpha cells into beta cells in vivo. The stable transgenic ins2:eGFP αTC1-6-cell line was used for evaluation of alpha-cell transdifferentiation in vitro. We further used multiple zebrafish transgenic and mutation lines to demonstrate beta-cell differentiation, beta-cell ablation and alpha-cell hyperplasia in this study. Key results: We showed that artemether and another sesquiterpene, Aspterric Acid, induced alpha-cell transdifferentiation into beta cells, both in zebrafish as well as using αTC1-6 cells. Furthermore, these two compounds also converted alpha cells into beta cells when beta cells were lost or alpha cells were hyperplastic in zebrafish. Unlike the previous report, the conversion of alpha cells to beta cells was mediated by increasing Pax4 expression, but not suppression of Arx expression. Conclusion and implications: Our data suggest that in zebrafish and αTC1-6 cells, both artemether and Aspterric Acid induce alpha-cell transdifferentiation. Our data, along with those of Li et al. (2017), suggested that artemether and Aspterric Acid were able to induce alpha-cell transdifferentiation, at least in zebrafish and αTC1-6 cells.

Aspterric Acid and 6-hydroxymellein, inhibitors of pollen development in Arabidopsis thaliana, produced by Aspergillus terreus

Z Naturforsch C J Biosci 2002 May-Jun;57(5-6):459-64.PMID:12132685DOI:10.1515/znc-2002-5-610.

Aspterric Acid, 6-Hydroxymellein, Arabidopsis thaliana, Aspergillus terreus Aspterric Acid (1) and 6-hydroxymellein (2), inhibitors of pollen development in Arabidopsis thaliana, have been isolated from the fungus Aspergillus terreus. 1 and 2 inhibited the pollen development at concentrations of 38 and 52 microM, respectively. The microscopic examination of pollen development suggested that the inhibition by the treatment with 1 caused at meiosis and the inhibition by the treatment with 2 caused at microspore stage. 1 and 2 could be useful agents for the molecular investigation of anther and pollen development in higher plants.

Interaction between Aspterric Acid and indole-3-acetic acid on reproductive growth in Arabidopsis thaliana

Z Naturforsch C J Biosci 2005 Jul-Aug;60(7-8):572-6.PMID:16163831DOI:10.1515/znc-2005-7-810.

Application of indole-3-acetic acid (IAA) with a pollen growth inhibitor, Aspterric Acid (AA), results in the recovery of normal pollen development. In contrast, application of gibberellin (GA3) with AA do not induce normal pollen growth. In addition, application of different concentrations of IAA with AA shortens the period of growth from bolting to first flowering as compared to that treated with AA alone. Furthermore, stem length and number of flower bud treated with IAA and AA were similar to those of control. These results suggest, that IAA may play an important role in reproductive growth of A. thaliana.

The role of Aspterric Acid in auxin-regulated reproductive growth of Arabidopsis thaliana

Z Naturforsch C J Biosci 2008 Jul-Aug;63(7-8):554-6.PMID:18811000DOI:10.1515/znc-2008-7-814.

Application of 100 microM Aspterric Acid (AA), a pollen growth inhibitor, with different concentrations of indole-3-acetic acid (IAA) results in the recovery of normal pollen development of Arabidopsis thaliana. Treatment with 100 microM AA plus 5 mM IAA significantly induced the normal seed production. Treatment with 100 microM N-1-naphthylphthalamic acid (NPA), a polar auxin transport inhibitor, did not reduce the pollen growth but inhibited seed production. 100 microM NPA plus 5 mM IAA did not induce any seed production. The endogenous level of IAA in stems and leaves of A. thaliana treated with 100 microM AA was similar to that of the untreated control. In contrast to AA treatment, the IAA level by the treatment with 100 microM NPA was about twice as much as that of the untreated control. These results suggest that AA affects the Arabidopsis reproductive growth without inhibiting IAA biosynthesis and transport.

Dihydroxy-Acid Dehydratases From Pathogenic Bacteria: Emerging Drug Targets to Combat Antibiotic Resistance

Chemistry 2022 Aug 4;28(44):e202200927.PMID:35535733DOI:10.1002/chem.202200927.

There is an urgent global need for the development of novel therapeutics to combat the rise of various antibiotic-resistant superbugs. Enzymes of the branched-chain amino acid (BCAA) biosynthesis pathway are an attractive target for novel anti-microbial drug development. Dihydroxy-acid dehydratase (DHAD) is the third enzyme in the BCAA biosynthesis pathway. It relies on an Fe-S cluster for catalytic activity and has recently also gained attention as a catalyst in cell-free enzyme cascades. Two types of Fe-S clusters have been identified in DHADs, i.e. [2Fe-2S] and [4Fe-4S], with the latter being more prone to degradation in the presence of oxygen. Here, we characterise two DHADs from bacterial human pathogens, Staphylococcus aureus and Campylobacter jejuni (SaDHAD and CjDHAD). Purified SaDHAD and CjDHAD are virtually inactive, but activity could be reversibly reconstituted in vitro (up to ∼19,000-fold increase with kcat as high as ∼6.7 s-1 ). Inductively-coupled plasma-optical emission spectroscopy (ICP-OES) measurements are consistent with the presence of [4Fe-4S] clusters in both enzymes. N-isopropyloxalyl hydroxamate (IpOHA) and Aspterric Acid are both potent inhibitors for both SaDHAD (Ki =7.8 and 51.6 μM, respectively) and CjDHAD (Ki =32.9 and 35.1 μM, respectively). These compounds thus present suitable starting points for the development of novel anti-microbial chemotherapeutics.