Homoisoflavonoids from Caesalpinia spp.: A Closer Look at Chemical and Biological Aspects

Baldim, João L.; Rosa, Welton; Santos, Mário Ferreira Conceição; Chagas‐Paula, Daniela Aparecida; Lago, João Henrique G.; Soares, Marisi G.

doi:10.5772/67723

Cited by 6 publications

(5 citation statements)

References 33 publications

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“…This result in line withBaldim et al (2017), species from genus Caesalpinia produce unique compounds named homoisoflavonoids. The most common class of homoisoflavonoids in the genus Caesalpinia is the sappanin-type which presents a 3-benzyl chromanone unit.…”

supporting

confidence: 56%

“…Based on LC-MS chromatogram (Figure 1), there were four highest compounds identified in combined extract. The most abundant compound in combined extract was 13 Homoisoflavonoids are oxygen heterocyclic compounds with two aromatic rings, and an additional carbon between the B and C rings on the isoflavonoid skeleton. This class is rare and unique subclass of flavonoids.…”

Section: Lc-ms Analysismentioning

confidence: 99%

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Alpha-glucosidase and DPP-IV Inhibitory Activities of Ethanol Extract from Caesalpinia sappan, Andrographis paniculata, and Syzygium cumini

Robbani¹,

Elya²,

Iswandana³

2022

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Syzygium cumini (synonym: Syzygium jambolanum or Eugenia cumini) is an original plant from India and the Asian sub-continent. Ayurvedic and Indian Folk Medicine have elaborated the use of this plant for diabetic treatment before the advent of insulin. 5 Based on the biochemical screening of methanolic and aqueous leaves extracts of Syzygium cumini, it showed that those extracts contained alkaloids, saponins, carbohydrates, flavonoids, terpenoids, glycosides and proteins. 6 Moreover, four types of flavonoid compounds are present in leaf extract of Syzygium cumini, quercetin, rutin, ellagic acid and kaempferol. The ethanolic leaf extract showed the highest quantity of quercetin. 7 Caesalpinia sappan L., commonly known as sappan wood or heartwood, is a plant of the Leguminosae family with various medicinal properties, such as skin rashes and excessive body heat, heartburn and indigestion, blood purifier, and diabetes. The pharmacological activity of sappan wood has been proven in various studies, including antioxidant, antibacterial, anti-acne, anti-inflammatory, antihypoglycemic and hepatoprotective. The most abundant water-soluble flavonoid in heartwood is Brazilin which gives red color in the extract. Therefore, sappan wood is also used as a coloring agent for the food, beverages, or textile industry. 8

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supporting

confidence: 56%

Section: Lc-ms Analysismentioning

confidence: 99%

Alpha-glucosidase and DPP-IV Inhibitory Activities of Ethanol Extract from Caesalpinia sappan, Andrographis paniculata, and Syzygium cumini

Robbani¹,

Elya²,

Iswandana³

2022

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“…Similar structures have been isolated in the Caesalpinia genus, such as, sappanol, episappanol, caesalpinianone, and 3′-deoxy-4-Omethylsappanol. In fact, sappanins are the most common homoisoflavonoids in this genus (Baldim et al 2017).…”

Section: Resultsmentioning

confidence: 99%

“…They are restricted only to some plant species including those from Fabaceae and Asparagaceae. These compounds have been isolated of several species of the genus Caesalpinia, such as, C. pulcherrima, C. echinata, C. bonduc, C. sappan, C. japonica, and C. milletti (Baldim et al 2017). Biological properties such as antimicrobial, antioxidant, anti-inflammatory, antitumoral, hypoglycemic, and hemostatic have been associated with the presence of homoisoflavonoids in the genus Caesalpinia (Zanin et al 2012).…”

Section: Introductionmentioning

confidence: 99%

A New Homoisoflavonoid from Caesalpinia bahamensis

González

Gaitén

Lizama

et al. 2020

Rev. Bras. Farmacogn.

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Homoisoflavonoids constitute a rare subclass of flavonoids restricted to only some plant species, including members of the genus Caesalpinia. This research focused on homoisoflavonoids from Caesalpinia bahamensis Lam., Fabaceae, a medicinal plant used in Cuban traditional medicine and known as "brasilete." An hydroalcoholic extract was prepared from the stem, followed by liquid-liquid partition and further chromatographic separations, resulting in the isolation and structure elucidation by nuclear magnetic resonance spectroscopy and mass spectrometry of an undescribed 3-(2-hydroxy-4-methoxybenzyl)chromane-4,7-diol, for which the name metasappanin was proposed.

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“…He had proposed that 2'-methoxy chalcones are the biosynthetic precursors of HIFs. The addition of C-9carbon (C-9) in 2'-methoxy chalcones is catalyzed by S-adenosyl-L-methionine-dependent methyltransferase (SAM)(Baldim et al 2017) and leads to formation of 16 carbon, 3'benzylchroman-4-one structure. Bonducellin is (E)-7-hydroxy-3-(4-methoxybenzylidene) chroman-4-one which is formed by transferring methyl group to the 3'-benzylchroman-4-one structures.…”

mentioning

confidence: 99%

De novo assembly and annotation of Caesalpinia bonducella L. seed transcriptome identifies key genes in the biosynthesis of bonducellin, a homoisoflavonoid

Veerapandiyan,

Ravichandiran,

N. Patra

et al. 2024

Natural Product Research

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Caesalpinia bonducella L. is a traditional medicinal plant containing a potential homoisoflavonoid, bonducellin, with therapeutic values against polycystic ovary syndrome, oxidative damage, pathogenic bacteria, irregular menstrual cycle, ovarian cancer and diabetes.Owing to the multi-therapeutic properties of bonducellin, knowledge of its biosynthetic pathway genes will help understand its regulatory mechanism and thus improve the yield. This study sequenced C. bonducella seed mRNA transcriptome to identify the genes in bonducellin biosynthesis. Before this, the presence of bonducellin in the seed samples was analysed by HPLC using the chemically synthesized bonducellin as the standard. Seven key genes encoding enzymes involved in the synthesis of bonducellin via the phenylpropanoid pathway were identified. The expression of selective genes from the bonducellin biosynthetic pathway was S2 validated using qRT-PCR and comparable with RNA-Seq data. Here, we put forth the sequences of 67,560 genes from C. bonducella and highlight the bonducellin biosynthetic pathway genes.

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Homoisoflavonoids from Caesalpinia spp.: A Closer Look at Chemical and Biological Aspects

Cited by 6 publications

References 33 publications

Alpha-glucosidase and DPP-IV Inhibitory Activities of Ethanol Extract from Caesalpinia sappan, Andrographis paniculata, and Syzygium cumini

Alpha-glucosidase and DPP-IV Inhibitory Activities of Ethanol Extract from Caesalpinia sappan, Andrographis paniculata, and Syzygium cumini

A New Homoisoflavonoid from Caesalpinia bahamensis

De novo assembly and annotation of Caesalpinia bonducella L. seed transcriptome identifies key genes in the biosynthesis of bonducellin, a homoisoflavonoid

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