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Extracts and compounds with anti-diabetic complications and anti-cancer activity from Castanea mollissina Blume (Chinese chestnut).

Zhang L, Gao HY, Baba M, Okada Y, Okuyama T, Wu LJ, Zhan LB - BMC Complement Altern Med (2014)

Bottom Line: CI-B was found to show a significant inhibitory effect in above biological screenings.Compounds 3-6, 8, and 9 showed stronger inhibitory effects than amino guanidine (positive control) on AGEs production.Our results suggest that flavonoids and polyphenolic acids possesses anti-diabetes complications and anti-cancer properties, and they were presumed to be the bioactive components of Castanea mollissima Blume.

View Article: PubMed Central - PubMed

Affiliation: Academy of Integrative Medicine, Dalian Medical University, No, 9, Western Section of South Road in Lvshun, Dalian 116044, China. sypugaohy@163.com.

ABSTRACT

Background: Castanea mollissima Blume (Chinese chestnut), as a food product is known for its various nutrients and functional values to the human health. The present study was carried out to analyze the anti-diabetic complications and anti-cancer activities of the bioactive compounds present in C. mollissima.

Methods: The kernels (CK), shells (CS) and involucres (CI) parts of C. Blume were extracted with 90% alcohol. The water suspension of these dried alcohol extracts were extracted using EtOAc and n-BuOH successively. The n-BuOH fraction of CI (CI-B) was isolated by silica gel column, Sephadex LH 20 column and preparative HPLC. The isolated compounds were identified by 1H-NMR, 13C-NMR, HMBC, HMQC and ESI-Q-TOF MS, All the fractions and compounds isolated were evaluated on human recombinant aldose reductase (HR-AR) assay, advanced glycation end products (AGEs) formation assay and human COLO 320 DM colon cancer cells inhibitory assay.

Results: CI-B was found to show a significant inhibitory effect in above biological screenings. Six flavonoids and three polyphenolic acids were obtained from CI-B. They were identified as kaempferol (1), kaempferol-3-O-[6''-O-(E)-p-coumaroyl]-β-D-glucopyranoside (2), kaempferol-3-O-[6''-O-(E)-p-coumaroyl]-β-D-galactopyranoside (3), kaempferol-3-O-[2''-O-(E)-p-coumaroyl]-β-D-glucopyranoside (4), kaempferol-3-O-[2", 6"-di-O-(E)-p-coumaroyl]-β-D-glucopyranoside (5) and kaempferol-3-O-[2", 6"-di-O-(E)-p-coumaroyl]-β-D-galactopyranoside (6), casuariin (7), casuarinin (8) and castalagin (9). Compounds 2-9 were found to show higher activity than quercetin (positive control) in the AR assay. Compounds 3-6, 8, and 9 showed stronger inhibitory effects than amino guanidine (positive control) on AGEs production. Compounds 4-6, 7, and 8 showed much higher cytotoxic activity than 5-fluorouracil (positive control) against the human COLO 320 DM colon cancer cells.

Conclusions: Our results suggest that flavonoids and polyphenolic acids possesses anti-diabetes complications and anti-cancer properties, and they were presumed to be the bioactive components of Castanea mollissima Blume.

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Related in: MedlinePlus

Inhibition ratio of all parts of the kernel (CK-A, CK-B, CK-W, CK), shell (CS-A, CS-B, CS-W, CS) and involucre (CI-A, CI-B, CI-W, CI) (10 μg/mL) in the AR assay, AGEs production and COLO 320DM proliferation. Positive Control (PC): Quercetin (3.3 μg/mL) for AR assay, AG (amino guanidine, 0.2 mM) for AGEs production and 5-Fu (5-fluorouracil, 50 μg/mL) for COLO 320DM proliferation, respectively.
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Fig3: Inhibition ratio of all parts of the kernel (CK-A, CK-B, CK-W, CK), shell (CS-A, CS-B, CS-W, CS) and involucre (CI-A, CI-B, CI-W, CI) (10 μg/mL) in the AR assay, AGEs production and COLO 320DM proliferation. Positive Control (PC): Quercetin (3.3 μg/mL) for AR assay, AG (amino guanidine, 0.2 mM) for AGEs production and 5-Fu (5-fluorouracil, 50 μg/mL) for COLO 320DM proliferation, respectively.

Mentions: All crude materials and soluble fractions (EtOAc, n-BuOH and water part) of kernels (CK, CK-A, CK-B, CK-W), shells (CS, CS-A, CS-B, CS-W) and involucres (CI, CI-A, CI-B, CI-W) were evaluated on AR, AGEs and the growth inhibitory activity aginst human COLO 320 DM colon cancer cells. Among these fractions, the n-BuOH soluble fraction of involucres (CI-B) was found to be significantly more active than others (Figure 3), and its inhibitory rates were 88.6 ± 2.3% in AR, 77.0 ± 5.8% in AGEs, and 81.3 ± 3.7% in cytotoxic assay respectively. Effective compounds from CI-B were further studied. Six flavonoids, kaempferol (1), kaempferol-3-O-[6"-O-(E)-p-coumaroyl]-β-D-glucopyranoside (2), kaempferol-3-O-[6"-O-(E)-p-coumaroyl]-β-D-galatopyranoside (3), kaempferol-3-O-[2"-O-(E)-p-coumaroyl]-β-D-glucopyranoside (4), kaempferol-3-O-[2", 6"-di-O-(E)-p-coumaroyl]-β-D-glucopyranoside (5), kaempferol-3-O-[2", 6"-di-O-(E)-p-coumaroyl]-β-D-galactopyranoside (6), and three polyphenolic acids, casuariin (7), casuarinin (8), and castalagin (9) were obtained. Structures of compounds (see Figure 1) were elucidated by the spectroscopic methods, including UV, ESI-MS, NMR experiments, and comparing their spectral data with reported in the references [3, 16, 17]. The inhibitory activities of compounds 1–9 were shown in Table 2.Figure 3


Extracts and compounds with anti-diabetic complications and anti-cancer activity from Castanea mollissina Blume (Chinese chestnut).

Zhang L, Gao HY, Baba M, Okada Y, Okuyama T, Wu LJ, Zhan LB - BMC Complement Altern Med (2014)

Inhibition ratio of all parts of the kernel (CK-A, CK-B, CK-W, CK), shell (CS-A, CS-B, CS-W, CS) and involucre (CI-A, CI-B, CI-W, CI) (10 μg/mL) in the AR assay, AGEs production and COLO 320DM proliferation. Positive Control (PC): Quercetin (3.3 μg/mL) for AR assay, AG (amino guanidine, 0.2 mM) for AGEs production and 5-Fu (5-fluorouracil, 50 μg/mL) for COLO 320DM proliferation, respectively.
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4226895&req=5

Fig3: Inhibition ratio of all parts of the kernel (CK-A, CK-B, CK-W, CK), shell (CS-A, CS-B, CS-W, CS) and involucre (CI-A, CI-B, CI-W, CI) (10 μg/mL) in the AR assay, AGEs production and COLO 320DM proliferation. Positive Control (PC): Quercetin (3.3 μg/mL) for AR assay, AG (amino guanidine, 0.2 mM) for AGEs production and 5-Fu (5-fluorouracil, 50 μg/mL) for COLO 320DM proliferation, respectively.
Mentions: All crude materials and soluble fractions (EtOAc, n-BuOH and water part) of kernels (CK, CK-A, CK-B, CK-W), shells (CS, CS-A, CS-B, CS-W) and involucres (CI, CI-A, CI-B, CI-W) were evaluated on AR, AGEs and the growth inhibitory activity aginst human COLO 320 DM colon cancer cells. Among these fractions, the n-BuOH soluble fraction of involucres (CI-B) was found to be significantly more active than others (Figure 3), and its inhibitory rates were 88.6 ± 2.3% in AR, 77.0 ± 5.8% in AGEs, and 81.3 ± 3.7% in cytotoxic assay respectively. Effective compounds from CI-B were further studied. Six flavonoids, kaempferol (1), kaempferol-3-O-[6"-O-(E)-p-coumaroyl]-β-D-glucopyranoside (2), kaempferol-3-O-[6"-O-(E)-p-coumaroyl]-β-D-galatopyranoside (3), kaempferol-3-O-[2"-O-(E)-p-coumaroyl]-β-D-glucopyranoside (4), kaempferol-3-O-[2", 6"-di-O-(E)-p-coumaroyl]-β-D-glucopyranoside (5), kaempferol-3-O-[2", 6"-di-O-(E)-p-coumaroyl]-β-D-galactopyranoside (6), and three polyphenolic acids, casuariin (7), casuarinin (8), and castalagin (9) were obtained. Structures of compounds (see Figure 1) were elucidated by the spectroscopic methods, including UV, ESI-MS, NMR experiments, and comparing their spectral data with reported in the references [3, 16, 17]. The inhibitory activities of compounds 1–9 were shown in Table 2.Figure 3

Bottom Line: CI-B was found to show a significant inhibitory effect in above biological screenings.Compounds 3-6, 8, and 9 showed stronger inhibitory effects than amino guanidine (positive control) on AGEs production.Our results suggest that flavonoids and polyphenolic acids possesses anti-diabetes complications and anti-cancer properties, and they were presumed to be the bioactive components of Castanea mollissima Blume.

View Article: PubMed Central - PubMed

Affiliation: Academy of Integrative Medicine, Dalian Medical University, No, 9, Western Section of South Road in Lvshun, Dalian 116044, China. sypugaohy@163.com.

ABSTRACT

Background: Castanea mollissima Blume (Chinese chestnut), as a food product is known for its various nutrients and functional values to the human health. The present study was carried out to analyze the anti-diabetic complications and anti-cancer activities of the bioactive compounds present in C. mollissima.

Methods: The kernels (CK), shells (CS) and involucres (CI) parts of C. Blume were extracted with 90% alcohol. The water suspension of these dried alcohol extracts were extracted using EtOAc and n-BuOH successively. The n-BuOH fraction of CI (CI-B) was isolated by silica gel column, Sephadex LH 20 column and preparative HPLC. The isolated compounds were identified by 1H-NMR, 13C-NMR, HMBC, HMQC and ESI-Q-TOF MS, All the fractions and compounds isolated were evaluated on human recombinant aldose reductase (HR-AR) assay, advanced glycation end products (AGEs) formation assay and human COLO 320 DM colon cancer cells inhibitory assay.

Results: CI-B was found to show a significant inhibitory effect in above biological screenings. Six flavonoids and three polyphenolic acids were obtained from CI-B. They were identified as kaempferol (1), kaempferol-3-O-[6''-O-(E)-p-coumaroyl]-β-D-glucopyranoside (2), kaempferol-3-O-[6''-O-(E)-p-coumaroyl]-β-D-galactopyranoside (3), kaempferol-3-O-[2''-O-(E)-p-coumaroyl]-β-D-glucopyranoside (4), kaempferol-3-O-[2", 6"-di-O-(E)-p-coumaroyl]-β-D-glucopyranoside (5) and kaempferol-3-O-[2", 6"-di-O-(E)-p-coumaroyl]-β-D-galactopyranoside (6), casuariin (7), casuarinin (8) and castalagin (9). Compounds 2-9 were found to show higher activity than quercetin (positive control) in the AR assay. Compounds 3-6, 8, and 9 showed stronger inhibitory effects than amino guanidine (positive control) on AGEs production. Compounds 4-6, 7, and 8 showed much higher cytotoxic activity than 5-fluorouracil (positive control) against the human COLO 320 DM colon cancer cells.

Conclusions: Our results suggest that flavonoids and polyphenolic acids possesses anti-diabetes complications and anti-cancer properties, and they were presumed to be the bioactive components of Castanea mollissima Blume.

Show MeSH
Related in: MedlinePlus