Chemical Constituents of the Stem Bark of the Hybrid Plant Citrus × paradisi Macfad. (Rutaceae)

Chemical Constituents of the Stem Bark of the Hybrid Plant Citrus × paradisi Macfad. (Rutaceae)

The stem bark of Citrus × paradisi Macfad. (Rutaceae) gave (23S)‐isolimonexic acid (1), limonin (2), citracridone II (3), citpressine II (4), citpressine I (5), grandisine (6), 2‐hydroxynoracronycine (7), citracridone I (8), 5‐methoxyseselin (9), umbelliferone (10), scopoletin (11), naringenin (12),...

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Bibliographic Details
Published in:Chemistry & biodiversity Vol. 19; no. 7; pp. e202101033 - n/a
Main Authors: Essombe Malolo, Fanny‐Aimée, Bellier Tabekoueng, George, Dongmo Tekapi Tsopgni, Willifred, Nguemdjo Chimeze, Valery Wilfried, Kenmogne Kouam, Ariane, Mas‐Claret, Eduard, Langat, Moses K., Ndom, Jean Claude, Frese, Marcel, Sewald, Norbert, Duplex Wansi, Jean
Format: Journal Article
Language:English
Published: Switzerland Wiley Subscription Services, Inc 01-07-2022
Subjects:
Adenocarcinoma
Alveoli
Bark
Cancer
Citrus paradise
Citrus paradisi
Cytotoxicity
Doxorubicin
Epithelial cells
Epithelium
hydrogenation
limonoids
Naringenin
NMR
Nuclear magnetic resonance
Prostate
Rutaceae
Toxicity
Tumor cell lines
Umbelliferone
Citrus paradise
limonoids
hydrogenation
cytotoxicity
Rutaceae
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Summary:The stem bark of Citrus × paradisi Macfad. (Rutaceae) gave (23S)‐isolimonexic acid (1), limonin (2), citracridone II (3), citpressine II (4), citpressine I (5), grandisine (6), 2‐hydroxynoracronycine (7), citracridone I (8), 5‐methoxyseselin (9), umbelliferone (10), scopoletin (11), naringenin (12), apigenin (13), friedelin (14), agrostophyllinone (15) and stigmasterol‐3‐O‐β‐D‐glucopyranoside (16). The structures of the compounds were determined using NMR and MS spectroscopic data, and by comparison with published data. The relative configuration of 1 was proposed as (23S)‐isolimonexic acid using NOE studies. Hydrogenation reaction of compound 3 led to the new derivative 3’,4’‐dihydrocitracridone II (3a). Cytotoxicity activities against the human adenocarcinoma alveolar basal epithelial cell lines A549 and the Caucasian prostate adenocarcinoma cell lines PC3, using the MTT assays showed that the methanol crude extract was significant with IC50 values of 30.1 and 31.7 μg/mL, respectively, with the positive control, doxorubicin giving an IC50 of 0.9 μM. In addition, compounds 3, 7 and 8 gave moderate cytotoxic activities with IC50 values of 33.1, 31.2 and 32.5 μM for A549 cells and 35.7, 33.8 and 34.9 μM for PC3 cells, respectively. The hydrogenated 3a was less active than 3, suggesting that the presence of the double bond in pyrans is important for structure‐activity relationship.
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content type line 23
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.202101033