Four New ent-Kaurane Diterpenoids from the Fruits of Annona cherimola

Miyashita, Hiroyuki; Nishida, Masaki; Okawa, Masafumi; Nohara, Toshihiro; Yoshimitsu, Hitoshi

doi:10.1248/cpb.58.765

Cited by 18 publications

(8 citation statements)

References 6 publications

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“…18.5-58.9 mg of kaurenoic acid per 100 g of fresh fruit. These values, although lower than the one reported for A. squamosa (90 mg per 100 g of fresh fruit) from the Amazon (Andrade et al, 2001), are significantly higher than those found for the specie A. cherimola (2.03 mg per 100 g of fresh fruit) (Miyashita et al, 2010) and A. glabra (3.9 mg per 100 g of fresh fruit) (Hsieh et al, 2004). The role of kaurenoic acid is mostly associated with the inhibition of inflammatory pain (Mizokami et al, 2012), antibacterial activity (Okoye et al, 2012) and anticonvulsant effect (Okoye, Akah, Omeje, Okoye, & Nworu, 2013), among other properties (Ambrosio, Tirapelli, da Costa, & de Oliveira, 2006).…”

Section: Composition Of the Lipophilic Extractscontrasting

confidence: 70%

“…As evoked above, two kaurene diterpenes (597-1560 mg kg À1 DW) are the most abundant lipophilic compounds present in the ripe cherimoya mesocarps, which account for 42.2% ('Mateus III') and 59.6% ('Funchal') of the total lipophilic extractives identified. This family of compounds have already been reported in the leaves, bark and fruits of A. glabra (Chang, Yang, Lin, Lee, & Wu, 1998;Hsieh, Wu, Chen, Huang, & Chen, 2004;Oliveira, Sant'Ana, & Bastos, 2002), in the fruit of A. cherimola (Miyashita, Nishida, Okawa, Nohara, & Yoshimitsu, 2010), in the leaves of A. reticulata (Thang et al, 2013) and in the stem bark of A. vepretorum (Dutra et al, 2014).…”

Section: Composition Of the Lipophilic Extractssupporting

confidence: 60%

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Profiling of lipophilic and phenolic phytochemicals of four cultivars from cherimoya (Annona cherimola Mill.)

et al. 2016

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The lipophilic and phenolic extractives of the ripe mesocarp of four cherimoya cultivars ('Perry Vidal', 'Mateus I', 'Mateus III' and 'Funchal') from Madeira Island, were studied for the first time. The predominant lipophilic compounds are kaurene diterpenes (42.2-59.6%), fatty acids (18.0-35.6%) and sterols (9.6-23.7%). Kaur-16-en-19-oic acid is the major lipophilic component of all cultivars accounting between 554 and 1350mgkg(-1) of dry material. The studied fruits also contain a high variety of flavan-3-ols, including galloylated and non-galloylated compounds. Five phenolic compounds were identified for the first time: catechin, (epi)catechin-(epi)gallocatechin, (epi)gallocatechin, (epi)afzelechin-(epi)catechin and procyanidin tetramer. 'Mateus I' and 'Mateus III' cultivars present the highest content of phenolic compounds (6299 and 9603mgkg(-1) of dry weight, respectively). These results support the use of this fruit as a rich source of health-promoting components, with the capacity to prevent or delay the progress of oxidative-stress related disorders.

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Section: Composition Of the Lipophilic Extractscontrasting

confidence: 70%

Section: Composition Of the Lipophilic Extractssupporting

confidence: 60%

Profiling of lipophilic and phenolic phytochemicals of four cultivars from cherimoya (Annona cherimola Mill.)

et al. 2016

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“…In addition, to treat gastrointestinal disorders such stomach pain, diarrhea, and dysentery; at present, it is used to treat diabetes. [ 16 19 20 ] Phytochemical investigations revealed the presence of alkaloids, flavonoids, sterols,[ 20 21 22 23 24 ] terpenoids,[ 25 26 27 ] cyclic peptides,[ 28 29 ] and acetogenins. [ 30 31 ] With regard to pharmacological investigations have been reported that A. cherimola extracts possess genotoxic, cytotoxic,[ 31 32 33 ] antihypercholesterolemic,[ 23 ] antihyperlipidemic[ 34 ] antidepressant,[ 22 ] cryoprotective,[ 35 ] anxiolytic,[ 25 ] antiprotozoal,[ 36 ] antisecretory,[ 37 ] antiarthritic,[ 38 ] antibacterial,[ 17 20 ] antifungal,[ 17 ] anti-inflammatory, antioxidant,[ 39 40 ] and inhibitor of mitochondrial complex I properties.…”

Section: Introductionmentioning

confidence: 99%

Antihyperglycemic activity of the leaves fromAnnona cherimolamiller and rutin on alloxan-induced diabetic rats

et al. 2017

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Background:Annona cherimola, known as “chirimoya” has been reported in Mexican traditional medicine for the treatment of diabetes.Objective:The aims of the present study were to validate and assess the traditional use of A. cherimola as an antidiabetic agent.Materials and Methods:The ethanol extract from A. cherimola (300 mg/kg, EEAc), subsequent fractions (100 mg/kg), and rutin (30 mg/kg) were studied on alloxan-induced type 2 diabetic (AITD) and normoglycemic rats. In addition, oral glucose tolerance test (OGTT) and oral sucrose tolerance test (OSTT) were performed in normoglycemic rats. Molecular docking technique was used to conduct the computational study.Results:Bioassay-guided fractionation of EEAc afforded as major antihyperglycemic compound, rutin. EEAc attenuated postprandial hyperglycemia in acute test using AITD rats (331.5 mg/dL) carrying the glycemic levels to 149.2 mg/dL. Rutin after 2 h, attenuated postprandial hyperglycemia in an acute assay using AITD rats such as EEAc, with maximum effect (150.0 mg/dL) being seen at 4 h. The antihyperglycemic activities of EEAc and rutin were comparable with acarbose (151.3 mg/dL). In the subchronic assay on AITD rats, the EEAc and rutin showed a reduction of the blood glucose levels since the 1st week of treatment, reaching levels similar to normoglycemic state (116.9 mg/kg) that stayed constant for the rest of the assay. OGTT and OSTT showed that EEAc and rutin significantly lowered blood glucose levels in normoglycemic rats at 2 h after a glucose or sucrose load such as acarbose. Computational molecular docking showed that rutin interacted with four amino acids residues in the enzyme α-glucosidase.Conclusion:The results suggest that rutin an α-glucosidase inhibitor was responsible in part of the antihyperglycemic activity of A. cherimola. Its in vivo antihyperglycemic activity is in good agreement with the traditional use of A. cherimola for the treatment of diabetes.SUMMARYThe ethanol extract from Annona cherimola (300 mg/kg, EEAc), subsequent fractions (100 mg/kg) and rutin (30 mg/kg) were studied on alloxan-induced type 2 diabetic (AITD) and normoglycemic rats. The results suggest that rutin; an α-glucosidase inhibitor was responsible in part of the antihyperglycemic activity of A. cherimola. Its in vivo antihyperglycemic activity is in good agreement with the traditional use of A. cherimola for the treatment of diabetes.Abbreviations Used: EEAc: The ethanol extract from Annona cherimola, AITD: Alloxan-induced type 2 diabetic rats, OGTT: Oral glucose tolerance test, OSTT: Oral sucrose tolerance test, DM: Diabetes mellitus

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“…) was shown to be abundant in the pulp of A. squamosa (0.9 g/kg; Andrade et al , ). Isolation from the fruit of A. cherimolia was published during preparation of this manuscript (Miyashita et al , ). This molecule exerts various biological activities (Ghisalberti, ) and raised safety concerns because of its cytotoxicity and genotoxicity in various cell lines in vitro (see Garcia et al , ).…”

Section: Introductionmentioning

confidence: 99%

Kaurenoic Acid from Pulp of Annona cherimolia in regard to Annonaceae‐induced Parkinsonism

Guillopé

Escobar-Khondiker

Guérineau

et al. 2011

Phytotherapy Research

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Guadeloupean Parkinsonism has been linked epidemiologically to the consumption of Annonaceae fruits. These were proposed to be etiological agents for sporadic atypical Parkinsonism worldwide, because of their content of neurotoxins such as isoquinolinic alkaloids and Annonaceous acetogenins. The pulp of Annona cherimolia Mill. from Spain was screened for these toxic molecules using Matrix-Assisted Laser Desorption Ionisation - Time of Flight mass spectrometry (MALDI-TOF MS) and it was found not to be a source of exposure. However, kaurenoic acid, a diterpene considered to be cytotoxic, was detected in high amounts (66 mg/fresh fruit). Treatment of rat embryonic striatal primary cultures, up to a high concentration (50 µM), did not cause neuronal death nor astrogliosis, suggesting that this molecule is not at risk of implication in human neurodegenerative diseases.

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Four New ent-Kaurane Diterpenoids from the Fruits of Annona cherimola

Cited by 18 publications

References 6 publications

Profiling of lipophilic and phenolic phytochemicals of four cultivars from cherimoya (Annona cherimola Mill.)

Profiling of lipophilic and phenolic phytochemicals of four cultivars from cherimoya (Annona cherimola Mill.)

Antihyperglycemic activity of the leaves fromAnnona cherimolamiller and rutin on alloxan-induced diabetic rats

Kaurenoic Acid from Pulp of Annona cherimolia in regard to Annonaceae‐induced Parkinsonism

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