Skip to main content
Erschienen in:

06.09.2022 | Original Paper

Lanceolanone A, a new biflavanone, and a chalcone glucoside from the flower heads of Coreopsis lanceolata and their aldose reductase inhibitory activity and AMPK activation

verfasst von: Yukiko Matsuo, Takuya Fujii, Hironao Kato, Kazuki Tomizawa, Haruhiko Fukaya, Katsunori Miyake, Minpei Kuroda, Yoshihiro Mimaki

Erschienen in: Journal of Natural Medicines | Ausgabe 1/2023

Einloggen, um Zugang zu erhalten

Abstract

The MeOH extract of the flower heads of Coreopsis lanceolata L. (Asteraceae) exhibited aldose reductase (AR) inhibitory activity (IC50 8.36 µg/mL). Bioassay-guided fractionation of the extract resulted in the isolation of a new biflavanone-named Lanceolanone A (1) and a chalcone glucoside (6), along with 12 known compounds (25 and 714), of which 4, 7, 9, 10, and 12 were isolated from C. lanceolata for the first time. The structures of the new compounds (1 and 6) were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and ECD calculation method. Compounds 2, 4, 11, 13, and 14 exhibited AR inhibitory activities with IC50 values between 2.40 and 9.99 µM. Furthermore, 813 at 1.0 mM activated AMPK expression in HepG2 human hepatoma cells compared to the control.

Graphical abstract

Anhänge
Nur mit Berechtigung zugänglich
Literatur
1.
Zurück zum Zitat Mahapatra DK, Asati V, Bharti SK (2015) Chalcones and their therapeutic targets for the management of diabetes: structural and pharmacological perspectives. Eur J Med Chem 92:839–865CrossRef Mahapatra DK, Asati V, Bharti SK (2015) Chalcones and their therapeutic targets for the management of diabetes: structural and pharmacological perspectives. Eur J Med Chem 92:839–865CrossRef
2.
Zurück zum Zitat Ramirez MA, Borja NL (2008) Epalrestat: an aldose reductase inhibitor for the treatment of diabetic neuropathy. Pharmacotherapy: J Human Pharmacol Drug Therapy 28: 646–655 Ramirez MA, Borja NL (2008) Epalrestat: an aldose reductase inhibitor for the treatment of diabetic neuropathy. Pharmacotherapy: J Human Pharmacol Drug Therapy 28: 646–655
3.
Zurück zum Zitat Kuroda M, Ohshima T, Kan C, Mimaki Y (2016) Chemical constituents of the leaves of Tussilago farfara and their aldose reductase inhibitory activity. Nat Prod Comm 11:1661–1664 Kuroda M, Ohshima T, Kan C, Mimaki Y (2016) Chemical constituents of the leaves of Tussilago farfara and their aldose reductase inhibitory activity. Nat Prod Comm 11:1661–1664
4.
Zurück zum Zitat Iguchi T, Kuroda M, Akiyama N, Hashimoto M, Mimaki Y (2022) Chemical constituents and aldose reductase inhibitory activities of Betula alba bark and leaves. Nat Prod Res 36:1004–1008CrossRef Iguchi T, Kuroda M, Akiyama N, Hashimoto M, Mimaki Y (2022) Chemical constituents and aldose reductase inhibitory activities of Betula alba bark and leaves. Nat Prod Res 36:1004–1008CrossRef
5.
Zurück zum Zitat Iguchi T, Kuroda M, Narita K, Mimaki Y (2019) Chemical constituents from the aerial parts of Achillea millefolium and their aldose reductase inhibitory activity. Shoyakugaku Zasshi 73:91–92 Iguchi T, Kuroda M, Narita K, Mimaki Y (2019) Chemical constituents from the aerial parts of Achillea millefolium and their aldose reductase inhibitory activity. Shoyakugaku Zasshi 73:91–92
6.
Zurück zum Zitat Iguchi T, Kuroda M, Kan C, Fujii T, Mimaki Y (2020) Chemical constituents in the whole-plant extract of Agrimonia eupatoria and their aldose reductase inhibitory activities. Shoyakugaku Zasshi 74:60–61 Iguchi T, Kuroda M, Kan C, Fujii T, Mimaki Y (2020) Chemical constituents in the whole-plant extract of Agrimonia eupatoria and their aldose reductase inhibitory activities. Shoyakugaku Zasshi 74:60–61
7.
Zurück zum Zitat McGaw LJ, Omokhua-Uyi AG, Finnie JF, Van Staden J (2022) Invasive alien plants and weeds in South Africa: a review of their applications in traditional medicine and potential pharmaceutical properties. J Ethnopharmacol 283:114564CrossRef McGaw LJ, Omokhua-Uyi AG, Finnie JF, Van Staden J (2022) Invasive alien plants and weeds in South Africa: a review of their applications in traditional medicine and potential pharmaceutical properties. J Ethnopharmacol 283:114564CrossRef
8.
Zurück zum Zitat Shang YF, Oidovsambuu S, Jeon JS, Nho CW, Um BH (2013) Chalcones from the flowers of Coreopsis lanceolata and their in vitro antioxidative activity. Planta Med 79:295–300CrossRef Shang YF, Oidovsambuu S, Jeon JS, Nho CW, Um BH (2013) Chalcones from the flowers of Coreopsis lanceolata and their in vitro antioxidative activity. Planta Med 79:295–300CrossRef
9.
Zurück zum Zitat Kim BR, Paudel SB, Nam JW, Jin CH, Lee IS, Han AR (2020) Constituents of Coreopsis lanceolata flower and their dipeptidyl peptidase IV inhibitory effects. Molecules 25:4370CrossRef Kim BR, Paudel SB, Nam JW, Jin CH, Lee IS, Han AR (2020) Constituents of Coreopsis lanceolata flower and their dipeptidyl peptidase IV inhibitory effects. Molecules 25:4370CrossRef
10.
Zurück zum Zitat Fang JB, Jia W, Gao WY, Yao Z, Teng J, Zhao AH, Duan HQ (2007) Antitumor constituents from Alternanthera philoxeroides. J Asian Nat Prod Res 9:511–515CrossRef Fang JB, Jia W, Gao WY, Yao Z, Teng J, Zhao AH, Duan HQ (2007) Antitumor constituents from Alternanthera philoxeroides. J Asian Nat Prod Res 9:511–515CrossRef
11.
Zurück zum Zitat Mondino A, Yaneselli K, Ingold A, Echeverry C, Raffaelli S, Vázquez Á, García y Santos C (2022) Cytotoxic effect of Senecio madagascariensis (Asteraceae) extracts on cancer derived cell lines. Agrociencia Uruguay 26:e425CrossRef Mondino A, Yaneselli K, Ingold A, Echeverry C, Raffaelli S, Vázquez Á, García y Santos C (2022) Cytotoxic effect of Senecio madagascariensis (Asteraceae) extracts on cancer derived cell lines. Agrociencia Uruguay 26:e425CrossRef
12.
Zurück zum Zitat Viollet B, Lantier L, Devin-Leclerc J, Hébrard S, Amouyal C, Mounier R, Andreelli F (2009) Targeting the AMPK pathway for the treatment of Type 2 diabetes. Front Biosci (Landmark Ed) 14:3380–3400CrossRef Viollet B, Lantier L, Devin-Leclerc J, Hébrard S, Amouyal C, Mounier R, Andreelli F (2009) Targeting the AMPK pathway for the treatment of Type 2 diabetes. Front Biosci (Landmark Ed) 14:3380–3400CrossRef
13.
Zurück zum Zitat Pardede A, Mashita K, Ninomiya M, Tanaka K, Koketsu M (2016) Flavonoid profile and antileukemic activity of Coreopsis lanceolata flowers. Bioorg Med Chem Lett 26:2784–2787CrossRef Pardede A, Mashita K, Ninomiya M, Tanaka K, Koketsu M (2016) Flavonoid profile and antileukemic activity of Coreopsis lanceolata flowers. Bioorg Med Chem Lett 26:2784–2787CrossRef
14.
Zurück zum Zitat Hoffmann B, Hölzl J (1988) New chalcones from Bidens pilosa. Planta Med 54:52–54CrossRef Hoffmann B, Hölzl J (1988) New chalcones from Bidens pilosa. Planta Med 54:52–54CrossRef
15.
Zurück zum Zitat Tanimoto S, Miyazawa M, Inoue T, Okada Y, Nomura M (2009) Chemical constituents of Coreopsis lanceolata L. and their physiological activities. J Oleo Sci 58:141–146CrossRef Tanimoto S, Miyazawa M, Inoue T, Okada Y, Nomura M (2009) Chemical constituents of Coreopsis lanceolata L. and their physiological activities. J Oleo Sci 58:141–146CrossRef
16.
Zurück zum Zitat Nakabo D, Okano Y, Kandori N, Satahiro T, Kataoka N, Akamatsu J, Okada Y (2018) Molecules 23:1671CrossRef Nakabo D, Okano Y, Kandori N, Satahiro T, Kataoka N, Akamatsu J, Okada Y (2018) Molecules 23:1671CrossRef
17.
Zurück zum Zitat Calanasan CA, MacLeod JK (1998) A diterpenoid sulphate and flavonoids from Wedelia asperrima. Phytochemistry 47:1093–1099CrossRef Calanasan CA, MacLeod JK (1998) A diterpenoid sulphate and flavonoids from Wedelia asperrima. Phytochemistry 47:1093–1099CrossRef
18.
Zurück zum Zitat Nacer A, Bernard A, Boustie J, Touzani R, Kabouche Z (2006) Aglycone flavonoids of Centaurea tougourensis from Algeria. Chem Nat Compd 42:230–231CrossRef Nacer A, Bernard A, Boustie J, Touzani R, Kabouche Z (2006) Aglycone flavonoids of Centaurea tougourensis from Algeria. Chem Nat Compd 42:230–231CrossRef
19.
Zurück zum Zitat Özgen U, Mavi A, Terzi Z, Kazaz C, Asçi A, Kaya Y, Seçen H (2011) Relationship between chemical structure and antioxidant activity of luteolin and its glycosides isolated from Thymus sipyleus subsp. sipyleus var. sipyleus. Rec Nat Prod 5:12–21 Özgen U, Mavi A, Terzi Z, Kazaz C, Asçi A, Kaya Y, Seçen H (2011) Relationship between chemical structure and antioxidant activity of luteolin and its glycosides isolated from Thymus sipyleus subsp. sipyleus var. sipyleus. Rec Nat Prod 5:12–21
20.
Zurück zum Zitat Park Y, Moon BH, Yang H, Lee Y, Lee E, Lim Y (2007) Complete assignments of NMR data of 13 hydroxymethoxyflavones. Magn Reson Chem 45:1072–1075CrossRef Park Y, Moon BH, Yang H, Lee Y, Lee E, Lim Y (2007) Complete assignments of NMR data of 13 hydroxymethoxyflavones. Magn Reson Chem 45:1072–1075CrossRef
21.
Zurück zum Zitat Benabderrahmane W, Amrani A, Benaissa O, Lores M, Lamas JP, de Miguel T, Benayache S (2020) Chemical constituents, in vitro antioxidant and antimicrobial properties of ethyl acetate extract obtained from Cytisus triflorus l’Her. Nat Prod Res 34:1586–1590CrossRef Benabderrahmane W, Amrani A, Benaissa O, Lores M, Lamas JP, de Miguel T, Benayache S (2020) Chemical constituents, in vitro antioxidant and antimicrobial properties of ethyl acetate extract obtained from Cytisus triflorus l’Her. Nat Prod Res 34:1586–1590CrossRef
22.
Zurück zum Zitat Basnet P, Matsushige K, Hase K, Kadota S, Namba T (1996) Four di-O-caffeoyl quinic acid derivatives from propolis. Potent hepatoprotective activity in experimental liver injury models. Biol Pharm Bull 19:1479–1484CrossRef Basnet P, Matsushige K, Hase K, Kadota S, Namba T (1996) Four di-O-caffeoyl quinic acid derivatives from propolis. Potent hepatoprotective activity in experimental liver injury models. Biol Pharm Bull 19:1479–1484CrossRef
23.
Zurück zum Zitat Meng Q, Qi X, Fu Y, Chen Q, Cheng P, Yu X, Bian H (2020) Flavonoids extracted from mulberry (Morus alba L.) leaf improve skeletal muscle mitochondrial function by activating AMPK in type 2 diabetes. J Ethnopharmacol 248: 112326 Meng Q, Qi X, Fu Y, Chen Q, Cheng P, Yu X, Bian H (2020) Flavonoids extracted from mulberry (Morus alba L.) leaf improve skeletal muscle mitochondrial function by activating AMPK in type 2 diabetes. J Ethnopharmacol 248: 112326
24.
Zurück zum Zitat Al-Ishaq RK, Abotaleb M, Kubatka P, Kajo K, Büsselberg D (2019) Flavonoids and their anti-diabetic effects: cellular mechanisms and effects to improve blood sugar levels. Biomolecules 9:430CrossRef Al-Ishaq RK, Abotaleb M, Kubatka P, Kajo K, Büsselberg D (2019) Flavonoids and their anti-diabetic effects: cellular mechanisms and effects to improve blood sugar levels. Biomolecules 9:430CrossRef
25.
Zurück zum Zitat Varshney R, Mishra R, Das N, Sircar D, Roy P (2019) A comparative analysis of various flavonoids in the regulation of obesity and diabetes: an in vitro and in vivo study. J Funct Foods 59:194–205CrossRef Varshney R, Mishra R, Das N, Sircar D, Roy P (2019) A comparative analysis of various flavonoids in the regulation of obesity and diabetes: an in vitro and in vivo study. J Funct Foods 59:194–205CrossRef
26.
Zurück zum Zitat Matsuo Y, Iguchi T, Kuroda M, Ishiguro M, Nara T, Takatori K, Mimaki Y (2020) Identification of flavone C-glycosides from Glycyrrhiza uralensis seeds and their effects on AMPK activation. Shoyakugaku Zasshi 74:108–109 Matsuo Y, Iguchi T, Kuroda M, Ishiguro M, Nara T, Takatori K, Mimaki Y (2020) Identification of flavone C-glycosides from Glycyrrhiza uralensis seeds and their effects on AMPK activation. Shoyakugaku Zasshi 74:108–109
27.
Zurück zum Zitat Janda E, Martino C, Riillo C, Parafati M, Lascala A, Mollace V, Boutin JA (2021) Apigenin and luteolin regulate autophagy by targeting NRH-Quinone oxidoreductase 2 in liver cells. Antioxidants 10:776CrossRef Janda E, Martino C, Riillo C, Parafati M, Lascala A, Mollace V, Boutin JA (2021) Apigenin and luteolin regulate autophagy by targeting NRH-Quinone oxidoreductase 2 in liver cells. Antioxidants 10:776CrossRef
28.
Zurück zum Zitat Si Q, Shi Y, Huang D, Zhang N (2020) Diosmetin alleviates hypoxia-induced myocardial apoptosis by inducing autophagy through AMPK activation. Mol Med Rep 22:1335–1341CrossRef Si Q, Shi Y, Huang D, Zhang N (2020) Diosmetin alleviates hypoxia-induced myocardial apoptosis by inducing autophagy through AMPK activation. Mol Med Rep 22:1335–1341CrossRef
29.
Zurück zum Zitat He WS, Wu Y, Ren MJ, Yu ZY, Zhao XS (2022) Diosmetin inhibits apoptosis and activates AMPK induced autophagy in myocardial damage under hypoxia environment. Kaohsiung J Med Sci 38:139–148CrossRef He WS, Wu Y, Ren MJ, Yu ZY, Zhao XS (2022) Diosmetin inhibits apoptosis and activates AMPK induced autophagy in myocardial damage under hypoxia environment. Kaohsiung J Med Sci 38:139–148CrossRef
Metadaten
Titel
Lanceolanone A, a new biflavanone, and a chalcone glucoside from the flower heads of Coreopsis lanceolata and their aldose reductase inhibitory activity and AMPK activation
verfasst von
Yukiko Matsuo
Takuya Fujii
Hironao Kato
Kazuki Tomizawa
Haruhiko Fukaya
Katsunori Miyake
Minpei Kuroda
Yoshihiro Mimaki
Publikationsdatum
06.09.2022
Verlag
Springer Nature Singapore
Erschienen in
Journal of Natural Medicines / Ausgabe 1/2023
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-022-01651-0