Three cytotoxic Annonaceous acetogenins from the seeds of Annona squamosa

Miao, Yunjie; Shi, Yue; Xu, Xiaofang; Chen, Yong; Chen, Jianwei; Li, Xiang

doi:10.1016/j.phytol.2016.03.006

Cited by 9 publications

(5 citation statements)

References 24 publications

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“…Over 500 AAs have been described to date; these compounds are characterized by a long aliphatic chain with an α, β-unsaturated γ-lactone ring and 0–3 tetrahydrofuran (THF) rings (Yuan et al, 2015), and have shown cytotoxic activity against different human cancer cell lines (i.e., lung, breast, colon, kidney, pancreas, prostate, liver, and bladder) (reviewed in Zeng et al, 1996; Chávez and Mata, 1998; Wang et al, 2002; Yuan et al, 2003; Mangal et al, 2016; Miao et al, 2016a; Miao et al, 2016b) besides in vivo antitumor activity (Chen et al, 2012a; Chen et al, 2012b). Herein, we reviewed the most recent reports about AAs in the drug discovery–oncology field.…”

Section: Introductionmentioning

confidence: 99%

Selective Acetogenins and Their Potential as Anticancer Agents

et al. 2019

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The Kingdom Plantae has provided several successful drugs for the treatment of different diseases, including cancer, and continues to be a source of new possible therapeutic molecules. For example, the annonaceous acetogenins (AAs) are secondary metabolites found in the Annonaceae family, which are plants employed in traditional medicine for the treatment of cancer and various other diseases. These polyketides are inhibitors of Complex I in the respiratory chain of tumor cells, a process that is closely related to tumor metabolism, cell death, apoptosis, and autophagy. The goal of this review is to update readers on the role of the AAs as antitumor agents using in vitro and in vivo studies to demonstrate their importance in the area of oncology drug discovery. For this purpose, we performed a literature search in the PubMed scientific database using a range of keywords, including acetogenins and cancer, acetogenins antitumor activity, acetogenins and cytotoxicity, and acetogenins mechanism of action, among others. As a result, we found that the AAs are cytotoxic compounds that can induce apoptosis, cell cycle arrest, and autophagy in vitro , in addition to exhibiting tumor growth inhibition in vivo . The functional group related to their antineoplastic activity is suggested to be the mono or bis tetrahydrofuran ring accompanied by two or more hydroxy groups. The versatility of the AA bioactivity therefore renders them potential therapeutic agents for cancer treatment. It is therefore apparent that nature is worth further examination to aid in the discovery of more effective, accurate, and less harmful therapies in the fight against cancer.

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Section: Introductionmentioning

confidence: 99%

Selective Acetogenins and Their Potential as Anticancer Agents

et al. 2019

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“…34,35 More recently, three new ACGs-squamocin-IV, squamocin-V, and squamoxinone-E-were isolated from the seeds of A. squamosa and evaluated for their cytotoxic activity. 36 Squamoxinone-E was the most active, with IC 50 values of 0.103, 0.43, and 0.687 g/mL against H460, Hep G2, and BGC-803 human cancer cell lines, respectively. Squamocin-IV showed a selective cytotoxic activity against the lung carcinoma H460 cell line, with an IC 50 value of 0.049 g/mL.…”

Section: Annonaceous Acetogeninsmentioning

confidence: 94%

“…More recently, three new ACGs—squamocin‐IV, squamocin‐V, and squamoxinone‐E—were isolated from the seeds of A. squamosa and evaluated for their cytotoxic activity . Squamoxinone‐E was the most active, with IC 50 values of 0.103, 0.43, and 0.687 μg/mL against H460, Hep G2, and BGC‐803 human cancer cell lines, respectively.…”

Section: Annonaceous Acetogeninsmentioning

confidence: 99%

Annona species (Annonaceae): a rich source of potential antitumor agents?

Tundis

Xiao

Loizzo

2017

Annals of the New York Academy of Sciences

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Plants have provided the basis of traditional medicine systems throughout the world for thousands of years and continue to yield molecules for new remedies. We analyzed studies published from 2009 to 2016 on the Annona species (Annonaceae), including A. coriacea, A. crassifolia, A. hypoglauca, A. muricata, A. squamosa, A. sylvatica, and A. vepretorum, as sources of potential antitumor agents. Here, we report and discuss the mechanisms of action and structure-activity relationships of the most active Annona constituents. Annonaceous acetogenins are one of the most promising classes of natural products, owing to their potential antitumor activity. However, their neurotoxicity should not be underestimated.

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“…Muricin O Seed (30) 5 Squamocin-V Seed (31) 6 Squamosten B Seed (30) 7 Squamocin P Seed (28) 8 Squamocin-IV Seed (31) 9 Squamotin A Seed (30) 10 Squamotin B Seed (30) Squamotin C Seed (30) 12 Squamotin D Seed (30) 13…”

Section: Phytochemical Literature Of Amentioning

confidence: 99%

“…Squamoxinone-E Seed (31) 14 Annosquatin-III Seed (28) 15 Annosquatin-IV Seed (30) 16 Annosquatin-V Seed (30)…”

Section: Phytochemical Literature Of Amentioning

confidence: 99%

Annona squamosa L.: A promising herbal remedy - Insights into its biological activities and phytochemical composition

Shokr,

Elsohafy,

Darwish

et al. 2024

Journal of Advanced Pharmaceutical Sciences

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Annonaceae is a large, prominent family within the Magnoliales order, containing many genera. Among these, the genus Annona holds significance for its substantial diversity and traditional medicinal value. Annona squamosa L. is one of the most common species of this genus. This tropical species, commonly known as the sugar apple, exhibits distinct morphological features. Phytochemical investigations of A. squamosa revealed the presence of acetogenins, alkaloids, diterpenes, and cyclopeptides in various plant parts. Acetogenins, found mainly in seeds and representing the major active constituents, possess distinctive structures and biological activities. Alkaloids, predominantly isolated from leaves, represent the second major class of A. squamosa active constituents. A. squamosa exhibits a wide array of pharmacological activities encompassing anti-tumor, anti-inflammatory, antioxidant, antidiabetic, antimicrobial, antiviral, immunomodulatory, and wound-healing properties. This comprehensive review highlights the botanical characteristics, phytochemical composition, and diverse pharmacological activities of A. squamosa and aims to be a guide for further research on A. squamosa.

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Three cytotoxic Annonaceous acetogenins from the seeds of Annona squamosa

Cited by 9 publications

References 24 publications

Selective Acetogenins and Their Potential as Anticancer Agents

Selective Acetogenins and Their Potential as Anticancer Agents

Annona species (Annonaceae): a rich source of potential antitumor agents?

Annona squamosa L.: A promising herbal remedy - Insights into its biological activities and phytochemical composition

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