Pterocarpans and isoflavones from the root bark of Millettia micans and of Millettia dura

Makungu, Marco; Deyou, Tsegaye; Gruhonjic, Amra; Holleran, John; Duffy, Sandra; Heydenreich, Matthias; Firtzpatrick, Paul A.; Landberg, Göran; Koch, Andreas; Derese, Solomon; Avery, Vicky M.; Erdélyi, Máté; Yenesew, Abiy

doi:10.1016/j.phytol.2017.07.012

Cited by 16 publications

(17 citation statements)

References 22 publications

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“…Compound 1 was obtained as an amorphous powder, whose molecular formula C 21 H 25 O 6 was determined based on HRESIMS ([M + Na] + m / z 395.1467, calcd 395.1471) and NMR (Table ) analyses. Its NMR spectra (Figures S1–S4, Supporting Information) showed signals characteristic for a pterocarpan (δ H 5.50, 4.22, 3.61, and 3.56) skeleton − and closely resembled those reported for 3-hydroxy-10-(3-hydroxy-3-methylbutyl)-9-methoxypterocarpan, except for the signals of the C-10 substituent. Based on their HMBC cross-peaks (Table S1, Figure S5, Supporting Information), the five aromatic protons were deduced to belong to rings A (δ H 7.35, 6.51, and 6.31) and D (δ H 7.13 and 6.51) of the pterocarpan skeleton, with their multiplicities (Table ) revealing their regiochemistry.…”

Section: Resultsmentioning

confidence: 99%

Flavonoids from Erythrina schliebenii

et al. 2017

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Prenylated and O-methylflavonoids including one new pterocarpan (1), three new isoflavones (2-4), and nineteen known natural products (5-23) were isolated and identified from the root, stem bark, and leaf extracts of Erythrina schliebenii. The crude extracts and their constituents were evaluated for antitubercular activity against Mycobacterium tuberculosis (H37Rv strain), showing MICs of 32-64 μg mL and 36.9-101.8 μM, respectively. Evaluation of their toxicity against the aggressive human breast cancer cell line MDA-MB-231 indicated EC values of 13.0-290.6 μM (pure compounds) and 38.3 to >100 μg mL (crude extracts).

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Section: Resultsmentioning

confidence: 99%

Flavonoids from Erythrina schliebenii

et al. 2017

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“…The crude CH 2 Cl 2 /CH 3 OH (1:1) extract of the roots of Tephrosia aequilata resulted in 100% growth inhibition of the chloroquine-sensitive (3D7) strain of Plasmodium falciparum at 10 µg/mL. The compounds isolated from this extract were also tested for antiplasmodial activity using a previously established protocol [ 27 , 28 ]. Compound 3 showed good (IC 50 < 5 µM), while all other compounds showed moderate (IC 50 6–9 µM) [ 29 ] antiplasmodial activities ( Table 4 ).…”

Section: Resultsmentioning

confidence: 99%

Three Chalconoids and a Pterocarpene from the Roots of Tephrosia aequilata

et al. 2017

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In our search for new antiplasmodial agents, the CH2Cl2/CH3OH (1:1) extract of the roots of Tephrosia aequilata was investigated, and observed to cause 100% mortality of the chloroquine-sensitive (3D7) strain of Plasmodium falciparum at a 10 mg/mL concentration. From this extract three new chalconoids, E-2′,6′-dimethoxy-3′,4′-(2′′,2′′-dimethyl)pyranoretrochalcone (1, aequichalcone A), Z-2′,6′-dimethoxy-3′,4′-(2′′,2′′-dimethyl)pyranoretrochalcone (2, aequichalcone B), 4′′-ethoxy-3′′-hydroxypraecansone B (3, aequichalcone C) and a new pterocarpene, 3,4:8,9-dimethylenedioxy-6a,11a-pterocarpene (4), along with seven known compounds were isolated. The purified compounds were characterized by NMR spectroscopic and mass spectrometric analyses. Compound 1 slowly converts into 2 in solution, and thus the latter may have been enriched, or formed, during the extraction and separation process. The isomeric compounds 1 and 2 were both observed in the crude extract. Some of the isolated constituents showed good to moderate antiplasmodial activity against the chloroquine-sensitive (3D7) strain of Plasmodium falciparum.

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“…( 2017 ) 93 2'- O -Methylisoauriculatin M. extensa stems Thailand, Raksat et al ( 2018 ) 94 Durmillone M. griffoniana; M. dielsiana; M. dura Root bark; Stems; Seed pod Cameroon, China, Kenya Yankep et al ( 2003 ); Yankep et al ( 1997 ); Ye et al ( 2014 ); Yenesewe et al ( 1996 ) 95 Calopogoniumisoflavone B M. griffoniana Root barks Cameroon, Kenya Yankep et al ( 1997 ); Marco et al ( 2017 ) 96 Jamaicin M. usaramensis; M. dura; M. griffoniana Root bark; Seed pods; root bark Kenya, Cameroon Deyou et al ( 2015 ); Yenesew et al ( 1997 ); Yankep et al ( 1997 ) 97 Ichthynone M. dielsiana Stems China Ye et al ( 2014 ) 98 6'',6''-Dimethyl-5-hydroxy-3'-methoxy-4'-hydroxypyrano[2,'',3'':7,6]isoflavone M. pachycarpa Seeds China Ye et al ( 2012a , b ) 99 4',5'-Dimethoxy-6,6-dimethylpyranoisoflavone M. pachycarpa Seeds China Tu et al ( 2019 ...…”

Section: Structural Diversity Of Millettia Isoflav...mentioning

confidence: 99%

“…Maackiain ( 149 ) was isolated from M. brandisiana and M. extensa roots, as well as M. nitida stems (Pailee et al 2019 ; Raksat et al 2018 ; Ye et al 2012a , b ) . On the other hand, (-)-medicarpin ( 148 ) and brandisianin F ( 147 ) were isolated from the leaves and roots of M. brandisiana , whereas erycristagallin ( 150 ) and 3- O -prenylmaackiain ( 151 ) were isolated from M. extensa leaves and M. duara root bark, respectively (Kikuchi et al 2007 ; Marco et al 2017 ; Pailee ete al. 2019 ; Raksat et al 2019 ).…”

Section: Structural Diversity Of Millettia Isoflav...mentioning

confidence: 99%

Millettia isoflavonoids: a comprehensive review of structural diversity, extraction, isolation, and pharmacological properties

Desta

El‐Aty

2022

Phytochem Rev

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There are approximately 260 known species in the genus Millettia , many of which are used in traditional medicine to treat human and other animal ailments in various parts of the world. Being in the Leguminosae (Fabaceae) family, Millettia species are rich sources of isoflavonoids. In the past three decades alone, several isoflavonoids originating from Millettia have been isolated, and their pharmacological activities have been evaluated against major diseases, such as cancer, inflammation, and diabetes. Despite such extensive research, no recent and comprehensive review of the phytochemistry and pharmacology of Millettia isoflavonoids is available. Furthermore, the structural diversity of isoflavonoids in Millettia species has rarely been reported. In this review, we comprehensively summarized the structural diversity of Millettia isoflavonoids, the methods used for their extraction and isolation protocols, and their pharmacological properties. According to the literature, 154 structurally diverse isoflavonoids were isolated and reported from the various tissues of nine well-known Millettia species. Prenylated isoflavonoids and rotenoids were the most dominant subclasses of isoflavonoids reported. Other subclasses of reported isoflavonoids include isoflavans, aglycone isoflavones, glycosylated isoflavones, geranylated isoflavonoids, phenylcoumarins, pterocarpans and coumaronochromenes. Although some isolated molecules showed promising pharmacological properties, such as anticancer, anti-inflammatory, estrogenic, and antibacterial activities, others remained untested. In general, this review highlights the potential of Millettia isoflavonoids and could improve their utilization in drug discovery and medicinal use processes. Supplementary Information The online version contains supplementary material available at 10.1007/s11101-022-09845-w.

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Pterocarpans and isoflavones from the root bark of Millettia micans and of Millettia dura

Cited by 16 publications

References 22 publications

Flavonoids from Erythrina schliebenii

Flavonoids from Erythrina schliebenii

Three Chalconoids and a Pterocarpene from the Roots of Tephrosia aequilata

Millettia isoflavonoids: a comprehensive review of structural diversity, extraction, isolation, and pharmacological properties

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