Caffeoylquinic acids in leaves of selected Apocynaceae species: Their isolation and content

Wong, Siu Kuin; Lim, Yau Yan; Ling, Sui Kiong; Chan, Eric Wei Chiang

doi:10.4103/0974-8490.122921

Cited by 28 publications

(7 citation statements)

References 36 publications

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“…The methanol extract, BK(B), exhibited IC 50 values of ≤20 µg/mL for three of the cancer cell lines used in the in vitro anti-cancer study, indicating very potent anti-cancer effects [33,34]. The isolation and subsequent purification activities of the BK(B) extract identified four compounds known as 4-O-caffeoyl quinic acid (2) [35], 5-O-caffeoyl quinic acid (chlorogenic acid) (3) [36,37], epi-catechin (4) [38], and procyanidin B2 (5) [39-41] by 1 H and 13 C spectroscopic analyses and comparison with the values in the literature or standard compounds (Figure 3).…”

Section: Isolation Purification and Identification Of Compoundmentioning

confidence: 99%

Phytochemicals from Rhizophora mucronata Propagules, Its In Vitro Anti-Cancer and In Silico Drug-Likeness Potential

et al. 2021

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This is the first report to identify the presence of 3-O-caffeoyl quinic acid (1), 4-O-caffeoyl quinic acid (2), 5-O-caffeoyl quinic acid (3), epi-catechin (4), and procyanidin B2 (5) in the young propagules of Rhizophora mucronata. Compounds 2–5 were purified and then treated against breast, colorectal, and ovarian cancer cell lines for 72 h and the results of the Sulphorhodomine-B (SRB) assay were evaluated for percent cell viability and IC50 values. Epi-catechin, 4-O-caffeoyl quinic acid, 5-O-caffeoyl quinic acid and procyanidin B2 showed strong to moderate inhibitory effects when treated on breast (T47D), colorectal (HT29), and ovarian (A2780, SKOV3) cancer cell lines with IC50 values ranging from 16.77 ± 0.58 to 28.28 ± 0.89 μg/mL. In silico evaluation was performed to evaluate the drug-likeness and toxicological effects of these compounds using Molinspiration calculation and OSIRIS program. It was found that compounds 2, 3, and 4 have the potential to be orally active and have a low risk in exerting the mutagenic, tumorigenic, irritant, and reproductive effects.

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Section: Isolation Purification and Identification Of Compoundmentioning

confidence: 99%

Phytochemicals from Rhizophora mucronata Propagules, Its In Vitro Anti-Cancer and In Silico Drug-Likeness Potential

et al. 2021

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“…These findings greatly enrich the compound diversity of H. citrina. Their structures were identified by the comparison of their spectroscopic data with literature values and were assigned as (E)-p-coumaric acid (1) [25], (Z)-p-coumaric acid ( 2 (11) [33], neochloro-genic acid (12) [34], crypto-chlorogenic acid (13) [35], chlorogenic acid ( 14) [36], 3-O-(E)feruloylquinic acid (15) [37], quercetin (16) [38], quercetin-3-O-α-L-arabinopyranoside (17) [39], quercetin-3-O-β-D-galactpyranoside ( 18 (11) [33], neochlorogenic acid (12) [34], cryptochlorogenic acid (13) [35], chlorogenic acid ( 14) [36], 3-O-(E)-feruloylquinic acid (15) [37], quercetin (16) [38], quercetin-3-O-α-L-arabinopyranoside (17) [39], quercetin-3-O-β-Dgalactpyranoside (18) [40], quercetin-3-O-β-D-glucopyranoside (19) (37) [53]. As far as we know, the nuclear magnetic data of compound 10 was reported for the first time.…”

Section: Enrichment Of Phenylpropanoids and Flavonoidsmentioning

confidence: 99%

An Investigation of the Anti-Depressive Properties of Phenylpropanoids and Flavonoids in Hemerocallis citrina Baroni

Sun

Wang

et al. 2022

Molecules

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The World Health Organization predicts that over the next several years, depression will become the most important mental health issue globally. Growing evidence shows that the flower buds of Hemerocallis citrina Baroni (H. citrina) possess antidepressant properties. In the search for new anti-depression drugs, a total of 15 phenylpropanoids and 22 flavonoids were isolated and identified based on spectral data (1D and 2D NMR, HR-ESI-MS, UV) from H. citrina. Among them, compound 8 was a novel compound, while compounds 1–4, 6, 9, 10, 15, 17, 24–26, 28, and 37 were isolated for the first time from Hemerocallis genus. To study the antidepressant activity of phenylpropanoids and flavonoids fractions from H. citrina, macroporous resin was used to enrich them under the guidance of UV characteristics. UHPLC-MS/MS was applied to identify the constituents of the enriched fractions. According to behavioral tests and biochemical analyses, it showed that phenylpropanoid and flavonoid fractions from H. citrina can improve the depressive-like mental state of chronic unpredictable mild stress (CUMS) rats. This might be accomplished by controlling the amounts of the inflammatory proteins IL-6, IL-1β, and TNF-α in the hippocampus as well as corticosterone in the serum. Thus, the monomer compounds were tested for their anti-neuroinflammatory activity and their structure–activity relationship was discussed in further detail.

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“…Apocynaceae contains about 250 genera and 2000 species [ 14 ]. Five sub-families are classified under Apocynaceae, including, Apocynoideae, Asclepiadoideae, Periplocoideae, Rauvolfioideae, and Secamonoideae.…”

Section: Introductionmentioning

confidence: 99%

“…Traditionally, species of this family have been used for the treatment of fever, malaria, gastrointestinal ailments, diabetes, and pain [ 15 ]. Additionally, some species have shown antiplasmodial and anticancer activities [ 14 ]. Several Apocynaceae MIAs have been used as anticancer, analgesic, anti-inflammatory and anti-spasmodic agents.…”

Section: Introductionmentioning

confidence: 99%

Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera

et al. 2021

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By the end of the twentieth century, the interest in natural compounds as probable sources of drugs has declined and was replaced by other strategies such as molecular target-based drug discovery. However, in the recent times, natural compounds regained their position as extremely important source drug leads. Indole-containing compounds are under clinical use which includes vinblastine and vincristine (anticancer), atevirdine (anti-HIV), yohimbine (erectile dysfunction), reserpine (antihypertension), ajmalicine (vascular disorders), ajmaline (anti-arrhythmic), vincamine (vasodilator), etc. Monoterpene Indole Alkaloids (MIAs) deserve the curiosity and attention of researchers due to their chemical diversity and biological activities. These compounds were considered as an impending source of drug-lead. In this review 444 compounds, were identified from six genera belonging to the family Apocynaceae, will be discussed. These genera (Alstonia, Rauvolfia, Kopsia, Ervatamia, and Tabernaemontana, and Rhazya) consist of 400 members and represent 20% of Apocynaceae species. Only 30 (7.5%) species were investigated, whereas the rest are promising to be investigated. Eleven bioactivities, including antibacterial, antifungal, anti-inflammatory and immunosuppressant activities, were reported. Whereas cytotoxic effect represents 47% of the reported activities. Convincingly, the genera selected in this review are a wealthy source for future anticancer drug lead.

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Caffeoylquinic acids in leaves of selected Apocynaceae species: Their isolation and content

Cited by 28 publications

References 36 publications

Phytochemicals from Rhizophora mucronata Propagules, Its In Vitro Anti-Cancer and In Silico Drug-Likeness Potential

Phytochemicals from Rhizophora mucronata Propagules, Its In Vitro Anti-Cancer and In Silico Drug-Likeness Potential

An Investigation of the Anti-Depressive Properties of Phenylpropanoids and Flavonoids in Hemerocallis citrina Baroni

Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera

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