Antifungal and Cytotoxic 2-Acylcyclohexane-1,3-diones from <i>Peperomia alata</i> and <i>P. trineura</i>

Ferreira, Edgard A.; Reigada, Juliana B.; Correia, Mauro Vicentini; Young, Maria Cláudia M.; Guimarães, Elsie Franklin; Franchi, Gilberto C.; Nowill, Alexandre E.; Lago, João Henrique G.; Yamaguchi, Lydia F.; Kato, Massuo Jorge

doi:10.1021/np500130x

Cited by 16 publications

(15 citation statements)

References 28 publications

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“…Cis geometry of double bond was confirmed on the basis of the typical shielded signals of α-olefinic carbons at δ C ∼ 26–27 while trans geometry showed around δ C ∼ 32–33. 19 The multiplet signal at δ H 2.96 (H-2′) correlated to the carbonyl carbon at δ H 206.1 (C-1′) in the HMBC experiment. The specific rotation of this compound was [ α ] 20.8 D = +37.1 ( c 0.1, MeOH) with the same sign as (+)-trineurone E. 19 The experimental ECD spectrum displayed a negative Cotton effect at 220 nm (Δ ε − 41.33) and positive Cotton effect at 237 (Δ ε + 7.13) and 288 (Δ ε + 11.00) which appropriately matched the calculated spectrum for the (6 R ) configuration.…”

Section: Discussionmentioning

confidence: 92%

Knecorticosanones C–H from the fruits of Knema globularia (Lam.) warb

et al. 2021

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Section: Discussionmentioning

confidence: 92%

Knecorticosanones C–H from the fruits of Knema globularia (Lam.) warb

et al. 2021

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“…Peperomia species have been the source of various bioactive compounds, such as aromatic compounds and polyketides [ 12 , 13 , 14 , 15 , 16 , 17 ]. Previous studies with P. obtusifolia reported the isolation of chromanes, flavonoids, and lignans [ 18 , 19 ].…”

Section: Resultsmentioning

confidence: 99%

Non-Clinical Studies for Evaluation of 8-C-Rhamnosyl Apigenin Purified from Peperomia obtusifolia against Acute Edema

Tamayose

Romoff

Toyama

et al. 2017

IJMS

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Compound 8-C-rhamnosyl apigenin (8CR) induced a moderate reduction in the enzymatic activity of secretory phospholipase A2 (sPLA2) from Crotalus durissus terrificus and cytosolic phospholipase A2 (cPLA2), but the compound also significantly inhibited the enzymatic activity of the enzyme cyclooxygenase. In vitro assays showed that the compound induced a slight change in the secondary structure of sPLA2 from Crotalus durissus terrificus snake venom. In vivo assays were divided into two steps. In the first step, the 8CR compound was administered by intraperitoneal injections 30 min prior to administration of sPLA2. In this condition, 8CR inhibited edema and myonecrosis induced by the sPLA2 activity of Crotalus durissus terrificus in a dose-dependent manner by decreasing interleukin-1β (IL-1β), tumor necrosis factor α (TNF-α), prostaglandin E2 (PGE2), and lipid peroxidation. This has been demonstrated by monitoring the levels of malondialdehyde (MDA) in rat paws after the course of edema induced by sPLA2. These results, for the first time, show that sPLA2 of Crotalus durissus terrificus venom induces massive muscle damage, as well as significant edema by mobilization of cyclooxygenase enzymes. Additionally, its pharmacological activity involves increased lipid peroxidation as well as TNF-α and IL-1β production. Previous administration by the peritoneal route has shown that dose-dependent 8CR significantly decreases the enzymatic activity of cyclooxygenase enzymes. This resulted in a decrease of the amount of bioactive lipids involved in inflammation; it also promoted a significant cellular protection against lipid peroxidation. In vivo experiments performed with 8CR at a concentration adjusted to 200 μg (8 mg/kg) of intraperitoneal injection 15 min after sPLA2 injection significantly reduced sPLA2 edema and the myotoxic effect induced by sPLA2 through the decrease in the enzymatic activity of cPLA2, cyclooxygenase, and a massive reduction of lipid peroxidation. These results clearly show that 8CR is a potent anti-inflammatory that inhibits cyclooxygenase-2 (COX-2), and it may modulate the enzymatic activity of sPLA2 and cPLA2. In addition, it was shown that Crotalus durissus terrificus sPLA2 increases cell oxidative stress during edema and myonecrosis, and the antioxidant properties of the polyphenolic compound may be significant in mitigating the pharmacological effect induced by sPLA2 and other snake venom toxins.

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“…These are secondary metabolites, derived by the repetitive condensation of acetate Anti-cancer Drugs -Nature, Synthesis and Cellunits or other short carboxylic acids catalyzed by multi-functional enzymes called polyketide synthases (PKSs) which is similar to fatty acid synthases [145]. Many polyketides suppress CML cell proliferation and induce apoptosis (Figure 3) (Table 6) [146][147][148][149][150][151][152][153][154][155].…”

Section: Polyketidesmentioning

confidence: 99%

Natural Products for Treatment of Chronic Myeloid Leukemia

Khajapeer¹,

Baskaran²

2016

Anti-Cancer Drugs - Nature, Synthesis and Cell

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Chronic myeloid leukemia (CML) is a hematological malignancy that arises due to reciprocal translocation of 3′ sequences from c-Abelson (abl) protooncogene on chromosome 9 with 5′ sequence of truncated break point cluster region (bcr) to chromosome 22. The fusion gene product BCR-ABL, a functional oncoprotein p210, is a constitutively activated tyrosine kinase that activates several cell proliferative signaling pathways. BCR-ABL-specific tyrosine kinase inhibitors (TKIs) such as imatinib, nilotinib and ponatinib potently inhibit CML progression. However, drug resistance owing to BCR-ABL mutations and overexpression is still an issue. Natural products are chemical compounds or substances produced by living organisms. They are becoming an important research area for cancer drug discovery due to their low toxicity and cost-effectiveness. Several lines of evidence show that many NPs such as alkaloids, flavonoids, terpenoids, polyketides, lignans and saponins inhibit CML cell proliferation and induce apoptosis. NPs not only differentiate CML cells into monocyte/erythroid lineage but also can reverse the multi-drug resistance (MDR) in CML cells. In this chapter, we review the anti-CML activity of various NPs.

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Antifungal and Cytotoxic 2-Acylcyclohexane-1,3-diones from Peperomia alata and P. trineura

Cited by 16 publications

References 28 publications

Knecorticosanones C–H from the fruits of Knema globularia (Lam.) warb

Knecorticosanones C–H from the fruits of Knema globularia (Lam.) warb

Non-Clinical Studies for Evaluation of 8-C-Rhamnosyl Apigenin Purified from Peperomia obtusifolia against Acute Edema

Natural Products for Treatment of Chronic Myeloid Leukemia

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