Caesalpanins A–C, Three Dimeric Cassane Diterpenoids from the Seeds of <i>Caesalpinia sappan</i> L.

Rutaceae plants are known for being a rich source of coumarins. Preliminary molecular docking showed that there was no significant difference for coumarins in Clausena and Murraya, both of which had high scoring values and showed good potential inhibitory activity to the MAO-B enzyme. Overall, 32 coumarins were isolated from Murraya exotica L., including a new coumarin 5-demethoxy-10′-ethoxyexotimarin F (1). Their structures were elucidated on the basis of a comprehensive analysis of 1D and 2D NMR and HRMS spectroscopic data, and the absolute configurations were assigned via a comparison of the specific rotations and the ECD exciton coupling method. The potential of new coumarin (1) as a selective inhibitor of MAO-B was initially evaluated through molecular docking and pharmacophore studies. Compound (1) showed selectivity for the MAO-B isoenzyme and inhibitory activity in the sub-micromolar range with an IC50 value of 153.25 ± 1.58 nM (MAO-B selectivity index > 172).

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“…The Nitric oxide (NO) production inhibition of the compounds ( 1 ) was determined using a procedure described before [ 45 ].…”

Section: Methodsmentioning

confidence: 99%

5-Demethoxy-10′-ethoxyexotimarin F, a New Coumarin with MAO-B Inhibitory Potential from Murraya exotica L.

et al. 2022

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“…as aromatic compounds (9), homoisoflavonoids (10) phenolic compounds (11), protosappanins (12) and diterpenoids (13). Biological studies such as anticancer (14), antibacterial (15), analgesic (16), immunomodulatory (17) antioxidant, anthelmintic properties (18) and toxicological studies (19) have been already documented.…”

Section: Research Articlementioning

confidence: 99%

Histological and in vitro seed culture studies on Biancaea sappan (L.) Tod. (Caesalpiniaceae)

Ebbie

Grace²,

Shanker³

et al. 2022

Plant Sci. Today

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Establishment of a tissue culture protocol for clonal regeneration is an essential prerequisite for the potential and economically important plant species Biancaea sappan (L.) Tod. (syn. Caesalpinia sappan L.; Caesalpiniaceae). This plant is a valuable dye-yielding legume shrub native to Indomalayan and is used in India by the local people of Kerala and Tamil Nadu States for its biological potential. The present study evaluated seed development both in vivo and in vitro through histological analysis. The mature seed was used as explants and cultured on modified Murashige and Skoog (MS) medium supplemented with 2, 4-D, BAP, GA3 and IBA. The cultures showed direct regeneration of shoots from nodular structures in the shoot apical meristem (SAM) region. During in vitro regeneration, the callus cells exhibited ballooning of cells, and the morphogenetic seed developed parenchymatous, polygonal cells filled with polyphenols. Histological studies indicated that in vitro plant regeneration involved the organogenic pathway that leads to de novo shoot primordia development.

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“…The latter two compounds do not show significant inhibitory activity against nitric oxide ( Zhao et al, 2014 ), a vasodilator found in blood vessels. The seeds of C. sappan are rich in diterpenoids, including caesalsappanin A−N, R and S ( Ma et al, 2015 ; Bao et al, 2016 ; Zhu et al, 2017 ; Wang et al, 2020 ); phanginin A−K and R‒T ( Yodsaoue et al, 2008 ; Bao et al, 2016 ); and ester glycosides, namely caesateroside A−C ( Wang et al, 2020 ). Oleanolic acid, a triterpenoid, has also been isolated from the plant ( Zheng et al, 2020 ).…”

Section: Caesalpinia Sappan and Its Bioactive Metabolitesmentioning

confidence: 99%

Protective Effects of Caesalpinia sappan Linn. and Its Bioactive Compounds on Cardiovascular Organs

2021

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Cardiovascular diseases are the leading cause of death worldwide. The long-term aim of cardiovascular disease therapy is to reduce the mortality rate and decelerate the progression of cardiovascular organ damage. Current therapies focus on recovering heart function and reducing risk factors such as hyperglycemia and dyslipidemia. However, oxidative stress and inflammation are important causes of further damage to cardiovascular organs. Caesalpinia sappan Linn. (Fabaceae), a flowering tree native to tropical Asia, has antioxidant and anti-inflammatory properties. It is used as a natural dye to color food and beverages and as a traditional treatment for diarrhea, diabetes, and blood stasis. The phytochemical compounds in C. sappan, mainly the homoisoflavonoids brazilin, sappanone A, protosappanin, and hematoxylin, can potentially be used to protect cardiovascular organs. This review aims to provide updates on recent developments in research on C. sappan in relation to treatment of cardiovascular diseases. Many studies have reported protective effects of the plant’s bioactive compounds that reduce cardiac damage and enhance vasorelaxation. For example, brazilin and sappanone A have an impact on molecular and cellular changes in cardiovascular disease pathogenesis, mainly by modulating oxidative, inflammatory, and apoptotic signaling pathways. Therefore, bioactive compounds of C. sappan have the potential to be developed as therapeutic agents to combat cardiovascular diseases like myocardial infarction and vascular disease. This review could help further the understanding of the possible modulatory role of the compounds in cardiovascular diseases, thereby facilitating future studies.

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Caesalpanins A–C, Three Dimeric Cassane Diterpenoids from the Seeds of Caesalpinia sappan L.

Cited by 16 publications

References 19 publications

5-Demethoxy-10′-ethoxyexotimarin F, a New Coumarin with MAO-B Inhibitory Potential from Murraya exotica L.

5-Demethoxy-10′-ethoxyexotimarin F, a New Coumarin with MAO-B Inhibitory Potential from Murraya exotica L.

Histological and in vitro seed culture studies on Biancaea sappan (L.) Tod. (Caesalpiniaceae)

Protective Effects of Caesalpinia sappan Linn. and Its Bioactive Compounds on Cardiovascular Organs

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