Antiproliferative and Antimalarial Sesquiterpene Lactones from <i>Piptocoma antillana</i> from Puerto Rico [1]

Y, Liu; Lh, Rakotondraibea; Pj, Brodie; Jd, Wiley; Cassera, MB; Goetzc, M; Dg, Kingstona

doi:10.1177/1934578x1400901002

Cited by 4 publications

(4 citation statements)

References 19 publications

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“…The EtOAc-soluble fraction obtained from a liquid–liquid partition of the EtOH extract (100 mg) showed antiplasmodial activity. Dereplication as previously described 21 indicated that the extract contained at least one new bioactive compound, so a larger sample was investigated. Fractionation of the EtOAc-soluble fraction of this sample by chromatography on Sephadex LH-20, reverse-phase SPE, normal-phase silic-gel column chromatography, and C 18 HPLC yielded compounds 1 and 6 – 8 , together with fractions that were mixtures of 5,6-dihydro-α-pyrones and bicyclic tetrahydro-α-pyrones.…”

Section: Resultsmentioning

confidence: 99%

Antimalarial 5,6-Dihydro-α-pyrones from Cryptocarya rigidifolia: Related Bicyclic Tetrahydro-α-Pyrones Are Artifacts1

et al. 2015

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Antimalarial bioassay-guided fractionation of an EtOH extract of the root wood of Cryptocarya rigidifolia (Lauraceae) led to the isolation of the five new 5,6-dihydro-α-pyrones cryptorigidifoliols A–E (1–5) and the six bicyclic tetrahydro-α-pyrone derivatives cryptorigidifoliols F–K (6–11). The structure elucidations of all compounds were made on the basis of the interpretation of spectroscopic data and chemical derivatization, and the relative and absolute configurations were determined by NOESY, electronic circular dichroism (ECD), and 1H NMR analysis of α-methoxyphenylacetyl (MPA) derivatives. The bicyclic tetrahydro-α-pyrone derivatives were identified as products of acid-catalyzed intramolecular Michael addition of the 5,6-dihydro-α-pyrones in the presence of silica gel. A structure–activity relationship study suggested that the presence of an α,β-unsaturated carbonyl moiety is not essential for potent antimalarial activity.

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Section: Resultsmentioning

confidence: 99%

Antimalarial 5,6-Dihydro-α-pyrones from Cryptocarya rigidifolia: Related Bicyclic Tetrahydro-α-Pyrones Are Artifacts1

et al. 2015

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“…Another antiplasmodial germacranolide, 15- O -methylgoyazensolide ( 206 ), was isolated from the leaf and twig extract of Piptocoma antillana (Asteraceae). It was equally active against the Dd2 strain and A2780 human ovarian cancer cells, indicating a non-selective antiplasmodial activity [132]. Antiplasmodial screening of 12 plants used in traditional medicine against malaria in Benin resulted in an extract of the aerial parts of Acanthospermum hispidum (Asteraceae) with potent activity against 3D7 and W2 parasites (IC 50 = 7.5 and 4.8 µg/mL, respectively) [133].…”

Section: Terpenesmentioning

confidence: 99%

Antiplasmodial natural products: an update

Tajuddeen

Heerden

2019

Malar J

127

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BackgroundMalaria remains a significant public health challenge in regions of the world where it is endemic. An unprecedented decline in malaria incidences was recorded during the last decade due to the availability of effective control interventions, such as the deployment of artemisinin-based combination therapy and insecticide-treated nets. However, according to the World Health Organization, malaria is staging a comeback, in part due to the development of drug resistance. Therefore, there is an urgent need to discover new anti-malarial drugs. This article reviews the literature on natural products with antiplasmodial activity that was reported between 2010 and 2017.MethodsRelevant literature was sourced by searching the major scientific databases, including Web of Science, ScienceDirect, Scopus, SciFinder, Pubmed, and Google Scholar, using appropriate keyword combinations.Results and DiscussionA total of 1524 compounds from 397 relevant references, assayed against at least one strain of Plasmodium, were reported in the period under review. Out of these, 39% were described as new natural products, and 29% of the compounds had IC50 ≤ 3.0 µM against at least one strain of Plasmodium. Several of these compounds have the potential to be developed into viable anti-malarial drugs. Also, some of these compounds could play a role in malaria eradication by targeting gametocytes. However, the research into natural products with potential for blocking the transmission of malaria is still in its infancy stage and needs to be vigorously pursued.

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“…Dereplication of an active EtOAc-soluble fraction obtained from liquid–liquid partition of the extract (100 mg) as previously described 13 indicated that it contained at least one new bioactive compound, so a larger sample was investigated. Fractionation of this extract yielded an antiproliferative EtOAc fraction, which was further subjected to size-exclusion column chromatography on Sephadex LH-20 followed by reversed-phase solid-phase extraction (SPE).…”

Section: Resultsmentioning

confidence: 99%

Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest1

Liu¹,

Young²,

Rakotondraibe³

et al. 2015

J. Nat. Prod.

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The two new lignans 3α-O-(β-d-glucopyranosyl)desoxypodophyllotoxin (1) and 4-O-(β-d-glucopyranosyl)dehydropodophyllotoxin (2) were isolated from Cleistanthus boivinianus, together with the known lignans deoxypicropodophyllotoxin (3), (±)-β-apopicropodophyllin (4), (−)-desoxypodophyllotoxin (5), (−)-yatein (6), and β-peltatin-5-O-β-d-glucopyranoside (7). The structures of all compounds were characterized by spectroscopic techniques. Compounds 1, 4, and 5 showed potent antiproliferative activities against the A2780 ovarian cancer cell line, with IC50 values of 33.0 ± 3.6, 63.1 ± 6.7, and 230 ± 1 nM, respectively. Compounds 2 and 7 showed only modest A2780 activities, with IC50 values of 2.1 ± 0.3 and 4.9 ± 0.1 μM, respectively, while compounds 3 and 6 had IC50 values of >10 μM. Compound 1 also had potent antiproliferative activity against the HCT-116 human colon carcinoma cell line, with an IC50 value of 20.5 nM, and compound 4 exhibited modest antiproliferative activity against the A2058 human caucasian metastatic melanoma and MES-SA human uterine sarcoma cell lines, with IC50 values of 4.6 and 4.0 μM, respectively.

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Antiproliferative and Antimalarial Sesquiterpene Lactones from Piptocoma antillana from Puerto Rico [1]

Cited by 4 publications

References 19 publications

Antimalarial 5,6-Dihydro-α-pyrones from Cryptocarya rigidifolia: Related Bicyclic Tetrahydro-α-Pyrones Are Artifacts1

Antimalarial 5,6-Dihydro-α-pyrones from Cryptocarya rigidifolia: Related Bicyclic Tetrahydro-α-Pyrones Are Artifacts1

Antiplasmodial natural products: an update

Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest1

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