2021
DOI: 10.3390/m1306
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New Derivatives of Lupeol and Their Biological Activity

Abstract: The natural product lupeol (1) was isolated from Bombax ceiba leaves, which were used as starting material in the semisynthetic approach. Three new derivatives (2a, 2b, and 3) were synthesized using oxidation and aldolization. Their chemical structures were elucidated by spectroscopic analyses (HRESIMS and NMR). Compounds 3 showed significant α-glucosidase inhibition with an IC50 value of 202 µM, whereas 2a and 2b were inactive.

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Cited by 3 publications
(3 citation statements)
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“…Both B. galpinii and C. caffum exhibited the presence of lupeol at a % area of 2.99 and 3.96, respectively, while M. obtusifolia and M. undata contained phytol at a % area of 2.80 and 1.78, respectively. Besides its known antioxidant activity, Lupeol and its derivatives were reported to possess enormous anticancer, wound-healing, and anti-inflammatory activities [ 67 , 68 , 69 ]. Elsewhere, phytol was found to possess a notable immunostumulant and antimicrobial activity [ 70 ].…”
Section: Discussionmentioning
confidence: 99%
“…Both B. galpinii and C. caffum exhibited the presence of lupeol at a % area of 2.99 and 3.96, respectively, while M. obtusifolia and M. undata contained phytol at a % area of 2.80 and 1.78, respectively. Besides its known antioxidant activity, Lupeol and its derivatives were reported to possess enormous anticancer, wound-healing, and anti-inflammatory activities [ 67 , 68 , 69 ]. Elsewhere, phytol was found to possess a notable immunostumulant and antimicrobial activity [ 70 ].…”
Section: Discussionmentioning
confidence: 99%
“…So far, flavonoids are extracted from natural plant resources through separation techniques [281,282]. Recently, much progress has been made through a synthetic chemistry approach to investigate the structure-activity of flavonoid moieties [283], to promote synthetic units that control a precise interaction site within the biological system [284,285], and to modify the flavonoid backbone to achieve new functionalities [286], paving the way toward the discovery of new drugs [287].…”
Section: Flavonoids As Nutraceuticals and Prebiotics For Human Healthmentioning
confidence: 99%
“…In the ninth paper, Dr. Diana Becerra, Dr. Juan-Carlos Castillo and colleagues from Universidad Pedagógica y Tecnológica de Colombia and Universidad de los Andes (Colombia) reported the synthesis of 2-oxo-2H-chromen-7-yl 4-chlorobenzoate obtained by O-acylation of 7-hydroxy-2H-chromen-2-one [9]. Eventually, in the tenth paper, lupeol extracted from Bombax ceiba was used by Dr. Thuc-Huy Duong from the Ho Chi Minh City University of Education (Vietnam), Dr. Jirapast Sichaem from Thammasat University (Thailand), and colleagues, as a starting material to produce semi-synthetic derivatives exhibiting α-glucosidase inhibitory activity [10].…”
mentioning
confidence: 99%