Strictosidinic acid
目录号 : GC61742
Strictosidinicacid是一种具有口服活性的，从Psychotriamyriantha叶中分离的糖苷吲哚单萜生物碱，抑制5-HT生物合成的前体酶并降低5-HT含量。Strictosidinicacid在小鼠中具有外周镇痛和解热活性。
Cas No.:150148-81-5
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
Strictosidinic acid, an orally active glycoside indole monoterpene alkaloid isolated from Psychotria myriantha leaves, inhibits precursor enzymes of 5-HT biosynthesis and reduces the 5-HT levels. Strictosidinic acid has peripheral analgesic and antipyretic activities in mice[1][2].
Strictosidinic acid (20 μg/μl; intra-hippocampal injection) causes a significance of 83.5% reduction in 5-HT levels. Strictosidinic acid (10 mg/kg; i.p.) causes a 63.4% reduction in 5-HT levels and a 67.4% reduction in DOPAC values in male Wistar rats, weighing 200-250 g[1].
[1]. F M Farias, et al. Strictosidinic Acid, Isolated From Psychotria Myriantha Mull. Arg. (Rubiaceae), Decreases Serotonin Levels in Rat Hippocampus. Fitoterapia. 2012 Sep;83(6):1138-43. [2]. F M Farias, et al. Monoamine Levels in Rat Striatum After Acute Intraperitoneal Injection of Strictosidinic Acid Isolated From Psychotria Myriantha Mull. Arg. (Rubiaceae). Phytomedicine. 2010 Mar;17(3-4):289-91.
| Cas No. | 150148-81-5 | SDF | |
| Canonical SMILES | O=C(C1=CO[C@@H](O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)[C@H](C=C)[C@@H]1C[C@@H]3NCCC4=C3NC5=C4C=CC=C5)O | ||
| 分子式 | C26H32N2O9 | 分子量 | 516.54 |
| 溶解度 | 储存条件 | 4°C, stored under nitrogen | |
| 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 | 1.936 mL | 9.6798 mL | 19.3596 mL |
| 5 mM | 0.3872 mL | 1.936 mL | 3.8719 mL |
| 10 mM | 0.1936 mL | 0.968 mL | 1.936 mL |
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| 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 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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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。
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Strictosidinic acid, isolated from Psychotria myriantha Mull. Arg. (Rubiaceae), decreases serotonin levels in rat hippocampus
Fitoterapia 2012 Sep;83(6):1138-43.PMID:22546150DOI:10.1016/j.fitote.2012.04.013.
Psychotria is a complex genus whose neotropical species are known by the presence of glucosidic monoterpene indole alkaloids. These compounds are able to display a large range of effects on the central nervous system, such as anxiolytic, antidepressant, analgesic, and impairment of learning and memory acquisition. The aims of this study were to investigate the effects displayed by Strictosidinic acid, isolated from Psychotria myriantha Mull. Arg. (Rubiaceae) leaves, on monoamine levels in rat hippocampus and on monoamine oxidase activity. A significance (p<0.01) of 83.5% reduction in 5-HT levels was observed after intra-hippocampal injection (20 μg/μl). After treatment by intraperitoneal route (10 mg/kg), a 63.4% reduction in 5-HT levels and a 67.4% reduction in DOPAC values were observed. The results indicate that Strictosidinic acid seems to act on 5-HT system in rat hippocampus, possibly inhibiting precursor enzymes of 5-HT biosynthesis. The decrease verified in DOPAC levels suggests a role of Strictosidinic acid in the dopaminergic transmission, probably due to an inhibition of monoamine oxidase activity, confirmed by the enzymatic assay, which demonstrated an inhibitory effect on MAO A in rat brain mitochondria.
Divergent camptothecin biosynthetic pathway in Ophiorrhiza pumila
BMC Biol 2021 Jun 16;19(1):122.PMID:34134716DOI:10.1186/s12915-021-01051-y.
Background: The anticancer drug camptothecin (CPT), first isolated from Camptotheca acuminata, was subsequently discovered in unrelated plants, including Ophiorrhiza pumila. Unlike known monoterpene indole alkaloids, CPT in C. acuminata is biosynthesized via the key intermediate Strictosidinic acid, but how O. pumila synthesizes CPT has not been determined. Results: In this study, we used nontargeted metabolite profiling to show that 3α-(S)-strictosidine and 3-(S), 21-(S)-strictosidinic acid coexist in O. pumila. After identifying the enzymes OpLAMT, OpSLS, and OpSTR as participants in CPT biosynthesis, we compared these enzymes to their homologues from two other representative CPT-producing plants, C. acuminata and Nothapodytes nimmoniana, to elucidate their phylogenetic relationship. Finally, using labelled intermediates to resolve the CPT biosynthesis pathway in O. pumila, we showed that 3α-(S)-strictosidine, not 3-(S), 21-(S)-strictosidinic acid, is the exclusive intermediate in CPT biosynthesis. Conclusions: In our study, we found that O. pumila, another representative CPT-producing plant, exhibits metabolite diversity in its central intermediates consisting of both 3-(S), 21-(S)-strictosidinic acid and 3α-(S)-strictosidine and utilizes 3α-(S)-strictosidine as the exclusive intermediate in the CPT biosynthetic pathway, which differs from C. acuminata. Our results show that enzymes likely to be involved in CPT biosynthesis in O. pumila, C. acuminata, and N. nimmoniana have evolved divergently. Overall, our new data regarding CPT biosynthesis in O. pumila suggest evolutionary divergence in CPT-producing plants. These results shed new light on CPT biosynthesis and pave the way towards its industrial production through enzymatic or metabolic engineering approaches.
Absolute configuration of Strictosidinic acid
Acta Crystallogr C 2012 Apr;68(Pt 4):m94-6.PMID:22476143DOI:10.1107/S0108270112010372.
The absolute configuration of Strictosidinic acid, (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-{[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl}-3,4-dihydro-2H-pyran-5-carboxylate, was determined from its sodium chloride trihydrate, poly[[diaqua((2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-{[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl]methyl}-3,4-dihydro-2H-pyran-5-carboxylate)sodium] chloride monohydrate], {[Na(C(26)H(32)N(2)O(9))(H(2)O)(2)]Cl·H(2)O}(n). The Strictosidinic acid molecule participates in intermolecular hydrogen bonds of the O-H...O and O-H...Cl types. The solid-state conformation was observed as a zwitterion, based on a charged pyridine N atom and a carboxylate group, the latter mediating the packing through coordination with the sodium cation.
Single mutations toggle the substrate selectivity of multifunctional Camptotheca secologanic acid synthases
J Biol Chem 2022 Sep;298(9):102237.PMID:35809640DOI:10.1016/j.jbc.2022.102237.
Terpene indole alkaloids (TIAs) are plant-derived specialized metabolites with widespread use in medicine. Species-specific pathways derive various TIAs from common intermediates, strictosidine or Strictosidinic acid, produced by coupling tryptamine with secologanin or secologanic acid. The penultimate reaction in this pathway is catalyzed by either secologanin synthase (SLS) or secologanic acid synthase (SLAS) according to whether plants produce secologanin from loganin or secologanic acid from loganic acid. Previous work has identified SLSs and SLASs from different species, but the determinants of selectivity remain unclear. Here, combining molecular modeling, ancestral sequence reconstruction, and biochemical methodologies, we identified key residues that toggle SLS and SLAS selectivity in two CYP72A (cytochrome P450) subfamily enzymes from Camptotheca acuminata. We found that the positions of foremost importance are in substrate recognition sequence 1 (SRS1), where mutations to either of two adjacent histidine residues switched selectivity; His131Phe selects for and increases secologanin production whereas His132Asp selects for secologanic acid production. Furthermore, a change in SRS3 in the predicted substrate entry channel (Arg/Lys270Thr) and another in SRS4 at the start of the I-helix (Ser324Glu) decreased enzyme activity toward either substrate. We propose that the Camptotheca SLASs have maintained the broadened activities found in a common asterid ancestor, even as the Camptotheca lineage lost its ability to produce loganin while the campanulid and lamiid lineages specialized to produce secologanin by acquiring mutations in SRS1. The identification here of the residues essential for the broad substrate scope of SLASs presents opportunities for more tailored heterologous production of TIAs.
Monoamine levels in rat striatum after acute intraperitoneal injection of Strictosidinic acid isolated from Psychotria myriantha Mull. Arg. (Rubiaceae)
Phytomedicine 2010 Mar;17(3-4):289-91.PMID:19576739DOI:10.1016/j.phymed.2009.05.008.
Strictosidinic acid 10mg/kg, isolated from Psychotria myriantha leaves, were administered intraperitoneally to Wistar male rats (n=5-6). After 60 minutes, striatum was dissected, homogenized and injected onto HPLC-ED chromatographic system. It was observed a 28.7% reduction in the 5-HT levels followed up by an increase of 5-HIAA levels (29.4%). Furthermore there was a decrease of 8.0% in DA levels and an increase in the levels of metabolites DOPAC (21.5%) and HVA (52.5%). The results indicate that Strictosidinic acid has a promising effect in the central nervous system, justifying more studies about the central actions of Psychotria compounds.