2035-15-6

Usage

Uses

Used in Agricultural Applications:
(-)-Maackiain is used as a natural fungicide for protecting plants from fungal infections. Its antimicrobial action makes it an effective tool in controlling and preventing the spread of fungal diseases in crops.
Used in Pharmaceutical Applications:
(-)-Maackiain is used as a potential antimicrobial agent for developing new drugs to combat fungal infections in humans. Its effectiveness against fungi suggests that it could be a promising candidate for the treatment of various fungal diseases.
Used in Food Preservation:
(-)-Maackiain is used as a natural preservative to prevent fungal growth in food products, thereby extending their shelf life and maintaining their quality. Its antimicrobial properties can help in reducing the risk of food spoilage caused by fungal contamination.

InChI:InChI=1/C16H12O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,11,16-17H,6-7H2/t11-,16-/m0/s1

Upstream product

• 76240-26-1 (+/-)-3-benzyloxy-8,9-methylenedioxyprerocarpan 
• 61080-20-4 2-(chloromercurio)-4,5-(methylenedioxy)phenol 
• 76240-25-0 7-benzyloxy-2H-1-benzopyran 
• 70371-58-3 1-(benzyloxy)-3-(prop-2-yn-1-yloxy)benzene 
• 108-46-3 recorcinol 
• 76240-24-9 7-benzyloxy-3,4-dihydro-2H-1-benzopyran-4-ol 
• 533-31-3 Sesamol 
• 6941-70-4 2-bromo-4,5-methylenedioxyphenol 
• 76240-23-8 3-(3-Hydroxyphenoxy)propanenitrile 
• 76240-27-2 7-hydroxy-2,3-dihydro-4H-chromen-4-one 
• 31042-20-3 7-(benzyloxy)chroman-4-one 

Downstream Products

• 61218-44-8 6a-hydroxymaackiain 
• 133067-72-8 (-)-sophorol 
• 524-08-3 (-)-7,2′-dihydroxy-4′,5′-methylenedioxyisoflavanone 
• 6807-83-6 trifolirhizin 
• 245678-49-3 (+)-3[1-S-N(1-methyl)benzyl-carbamoyl]-6aS,11aS-maackiain 
• 245678-56-2 (-)-3[1-S-N(1-methyl)benzylcarbamoyl]-6aR,11aR-maackiain 
• 84297-59-6 rac-cabenegrin A-I 

Relevant academic research and scientific papers

(+)-Pisatin biosynthesis: From (-) enantiomeric intermediates via an achiral 7,2′-dihydroxy-4′,5′-methylenedioxyisoflav-3-ene

(+)-Pisatin, produced by peas (Pisum sativum L.), is an isoflavonoid derivative belonging to the pterocarpan family. It was the first chemically identified phytoalexin, and subsequent research has demonstrated that most legumes produce pterocarpans with the opposite stereochemistry. Studies on the biosynthesis of (+)-pisatin have shown that (-) enantiomeric compounds are intermediates in (+)-pisatin synthesis. However, the steps from the (-)-7,2′-dihydroxy-4′,5′-methylenedioxyisoflavanone [(-)-sophorol] intermediate to (+)-6a-hydroxymaackiain intermediate are undetermined. Chemical reduction of (-)-sophorol using sodium borohydride (NaBH4) produced two isomers of (-)-7,2′-dihydroxy-4′, 5′-methylenedioxyisoflavanol [(-)-DMDI] with optimal UV absorbance at 299.3 and 300.5 nm, respectively. In contrast, enzymatic reduction of (-)-sophorol by the pea enzyme sophorol reductase (SOR) produced only the 299.3 nm (-)-DMDI isomer. Proton nuclear magnetic resonance (1H NMR) analysis of the 299.3 nm (-)-DMDI isomer demonstrated that this isomer had the same NMR spectrum as previously reported for cis-isoflavanol isomers, indicating that cis-(-)-DMDI is an intermediate in (+)-pisatin biosynthesis. Enzyme assays using protein extracts from pea tissue treated with CuCl2 as an elicitor converted the cis-(-)-DMDI isomer into an achiral isoflavene, 7,2′-dihydroxy-4′,5′-methylenedioxyisoflav-3-ene (DMDIF), and the trans-(-)-DMDI isomer was not metabolized by the same protein preparation. A comparison of the enzyme activities on cis-(-)-DMDI with protein preparations from elicited tissue versus non-elicited tissue showed a threefold increase in the amount of activity in the proteins from the elicited tissue. Proteins from the elicited tissues of alfalfa, bean, and chickpea converted cis-(-)-DMDI into either (-)-maackiain and/or (-)-sophorol, while proteins from the elicited tissues of broccoli and pepper produced no detectable product. These results are consistent with the involvement of cis-(-)-DMDI and the achiral DMDIF as intermediates in (+)-pisatin biosynthesis.

Maackiain is a novel antiallergic compound that suppresses transcriptional upregulation of the histamine H1 receptor and interleukin-4 genes

Kujin contains antiallergic compounds that inhibit upregulation of histamine H1 receptor (H1R) and interleukin (IL)-4 gene expression. However, the underlying mechanism remains unknown. We sought to identify a Kujin-derived antiallergic compound and investigate its mechanism of action. The H1R and IL-4 mRNA levels were determined by real-time quantitative RT-PCR. To investigate the effects of maackiain in?vivo, toluene-2,4-diisocyanate (TDI)-sensitized rats were used as a nasal hypersensitivity animal model. We identified (?)-maackiain as the responsible component. Synthetic maackiain showed stereoselectivity for the suppression of IL-4 gene expression but not for H1R gene expression, suggesting distinct target proteins for transcriptional signaling. (?)-Maackiain inhibited of PKCδ translocation to the Golgi and phosphorylation of Tyr311 on PKCδ, which led to the suppression of H1R gene transcription. However, (?)-maackiain did not show any antioxidant activity or inhibition of PKCδ enzymatic activity per se. Pretreatment with maackiain alleviated nasal symptoms and suppressed TDI-induced upregulations of H1R and IL-4 gene expressions in TDI-sensitized rats. These data suggest that (?)-maackiain is a novel antiallergic compound that alleviates nasal symptoms in TDI-sensitized allergy model rats through the inhibition of H1R and IL-4 gene expression. The molecular mechanism underlying its suppressive effect for H1R gene expression is mediated by the inhibition of PKCδ activation.

(±)-3,4-Dihydroxy-8,9-methylenedioxypterocarpan and derivatives: Cytotoxic effect on human leukemia cell lines

Naturally occurring pterocarpans 1a,b, pterocarpan 1c, isoflavane 2 and ortho-quinone 3 were synthesized in the racemic form and their cytotoxic effect was evaluated on the human leukemia cell lines K562 (resistant to oxidative stress), Lucena-1 (MDR phenotype) and HL-60. Ortho-quinone 3 (IC50 = 1.5 μM, 1.8 μM and 0.2 μM, respectively) and catechol pterocarpan 1a (IC50 = 3.0 μM, 3.7 μM and 2.1 μM, respectively) were the most active compounds on these cells and were also evaluated on other human leukemia cell lines (Jurkat and Daudi). Ortho-quinone 3 was 2 to 10 times more potent than pterocarpan 1a, depending on the cell line considered, however, showed a greater toxicity for lymphocytes activated by PHA.

Inactivation of pea genes by RNAi supports the involvement of two similar O-methyltransferases in the biosynthesis of (+)-pisatin and of chiral intermediates with a configuration opposite that found in (+)-pisatin

(+)-Pisatin, the major phytoalexin of pea (Pisum sativum L.), is believed to be synthesized via two chiral intermediates, (-)-7,2′-dihydroxy-4′,5′-methylenedioxyisoflavanone [(-)-sophorol] and (-)-7,2′-dihydroxy-4′,5′-methylenedioxyisoflavanol [(-)-DMDI]; both have an opposite C-3 absolute configuration to that found at C-6a in (+)-pisatin. The expression of isoflavone reductase (IFR), which converts 7,2′-dihydroxy-4′,5′-methylenedioxyisoflavone (DMD) to (-)-sophorol, sophorol reductase (SOR), which converts (-)-sophorol to (-)-DMDI, and hydroxymaackiain-3-O-methyltransferase (HMM), believed to be the last step of (+)-pisatin biosynthesis, were inactivated by RNA-mediated genetic interference (RNAi) in pea hairy roots. Some hairy root lines containing RNAi constructs of IFR and SOR accumulated DMD or (-)-sophorol, respectively, and were deficient in (+)-pisatin biosynthesis supporting the involvement of chiral intermediates with a configuration opposite to that found in (+)-pisatin in the biosynthesis of (+)-pisatin. Pea proteins also converted (-)-DMDI to an achiral isoflavene suggesting that an isoflavene might be the intermediate through which the configuration is changed to that found in (+)-pisatin. Hairy roots containing RNAi constructs of HMM also were deficient in (+)-pisatin biosynthesis, but did not accumulate (+)-6a-hydroxymaackiain, the proposed precursor to (+)-pisatin. Instead, 2,7,4′-trihydroxyisoflavanone (TIF), daidzein, isoformononetin, and liquiritigenin accumulated. HMM has a high amino acid similarity to hydroxyisoflavanone-4′-O-methyltransferase (HI4′OMT), an enzyme that methylates TIF, an early intermediate in the isoflavonoid pathway. The accumulation of these four compounds is consistent with the blockage of the synthesis of (+)-pisatin at the HI4′OMT catalyzed step resulting in the accumulation of liquiritigenin and TIF and the diversion of the pathway to produce daidzein and isoformononetin, compounds not normally made by pea. Previous results have identified two highly similar "HMMs" in pea. The current results suggest that both of these O-methyltransferases are involved in (+)-pisatin biosynthesis and that one functions early in the pathway as HI4′OMT and the second acts at the terminal step of the pathway.

Absolute configuration and total synthesis of (-)-cabenegrin A-I

The total synthesis of (-)-cabenegrin A-I [(-)-1] in five steps was achieved from (-)-6aR, 11aR-maackiain [(-)-5], which in turn was prepared by the optical resolution of racemic (±)-5 using S-(-)α-methylbenzyl isocyanate as the the chiral auxiliary. The homochirality of(-)-maackiain [(- )-5] and (-)cabenegrin A-I [(-)-1] was proved by CD measurements. Synthesis of (±)maackiain [(±)-5] is also presented, starting from the readily available phenol derivatives resorcinol and sesamol, which demonstrates the synthetic utility of the Heck-type oxyarylation process for obtaining pterocarpane derivatives on a multigram scale. A new ring-opening reaction of pterocarpanes (7 → 28) is described.

SYNTHESIS OF (+/-)-CABENEGRINS A-I AND A-II

(+/-)-Cabenegrins A-I and A-II, the potent antidotes against snake venoms, have been synthesized from maakiain (9) and 2-carbomethoxy-3-benzyl maakiain (20).