L'apigenina è un flavonoide naturale presente in varie piante, in particolare in erbe come il prezzemolo, la camomilla, il sedano, in verdure, frutta, origano, tè, germogli di grano. È conosciuta per le sue proprietà antiossidanti, antinfiammatorie e potenzialmente anticancerogene. Nelle formulazioni cosmetiche, l'apigenina è apprezzata per la sua capacità di lenire la pelle, ridurre il rossore e proteggere dai fattori di stress ambientale. La sua incorporazione nei prodotti per la cura della pelle aiuta a promuovere un incarnato più sano e radioso.

Composizione Chimica e Struttura

L'apigenina è caratterizzata da:

• Formula Chimica: C₁₅H₁₀O₅
• Struttura: Un flavone con uno scheletro composto da un sistema ad anello benzopirano, contenente gruppi idrossilici (-OH) che contribuiscono alla sua attività antiossidante.

La struttura unica dell'apigenina le consente di neutralizzare efficacemente i radicali liberi e fornire vari benefici per la salute.

Proprietà Fisiche

• Aspetto: Tipicamente una polvere cristallina da giallo pallido a bianco.

• Solubilità: Solubile in solventi organici; leggermente solubile in acqua.

• Punto di Fusione: Generalmente fonde a circa 334–335°C (633–635°F).

• Odore: Inodore.

• Stabilità: Stabile in condizioni normali di conservazione; deve essere protetta da calore eccessivo e luce.

Processo di Produzione

1. Estrazione: L'apigenina viene estratta da fonti vegetali utilizzando metodi come l'estrazione con solvente o la distillazione a vapore per ottenere il flavonoide in forma concentrata.

2. Purificazione: L'estratto viene purificato per rimuovere impurità e garantire un prodotto di alta qualità.

3. Formulazione: L'apigenina purificata viene incorporata in vari prodotti cosmetici per migliorarne le proprietà lenitive e protettive.

Applicazioni

• Cosmetici: Comunemente utilizzata in sieri, creme e lozioni per i suoi benefici antiossidanti e antinfiammatori. Aiuta a calmare la pelle irritata, ridurre il rossore e migliorare la salute della pelle nel complesso.

Funzioni INCI:

Agente antiossidante. Ingrediente che contrasta lo stress ossidativo e che evita danni cellulari. I radicali liberi, i processi infiammatori patologici, le specie reattive dell'azoto e le specie reattive dell'ossigeno sono responsabili del processo di invecchiamento e di molte malattie causate dall'ossidazione.

Agente condizionante per capelli. Nelle formulazioni di shampoo per capelli possono coesistere una quantità rilevante di ingredienti con scopi specifici e mirati: detergenti, condizionanti, addensanti, opacizzanti, sequestranti, fragranze, conservanti, additivi particolari. Tuttavia gli ingredienti indispensabili sono i detergenti ed i condizionanti in quanto necessari e sufficienti per la pulizia e la gestibilità dei capelli. Gli altri hanno funzioni accessorie commerciali e non indispensabili come: aspetto estetico, profumo, colorazione ecc. Gli agenti condizionanti per i capelli hanno il compito di aumentarne la lucentezza, la maneggevolezza ed il volume, ridurne l'elettricità statica soprattutto dopo trattamenti quali colorazione, stiratura, ondulazione, asciugatura e spazzolatura. Sono, in pratica, dispersori che possono contenere tensioattivi cationici, addensanti, emollienti, polimeri. La tipologia degli agenti condizionatori per capelli comprende: condizionatori intensivi, condizionatori istantanei, condizionatori addensanti, condizionatori per l'asciugatura. Possono svolgere il loro compito generalmente accompagnati da altri diversi ingredienti.

CAS 520-36-5

EC number 208-292-3

• Farmaceutici: Esplorata per i suoi potenziali effetti terapeutici in varie applicazioni legate alla salute (1), inclusa la sua funzione nel trattamento del cancro (2), come antinfiammatorio (3), cardioprotettivo (4), come contrasto alla progressione delle cellule tumorali della prostata (5) e come neuroprotettivo (6)

• Integratori Alimentari: Talvolta inclusa negli integratori per le sue proprietà antiossidanti.

Considerazioni Ambientali e di Sicurezza

L'apigenina è generalmente considerata sicura per l'uso nei cosmetici quando applicata secondo le linee guida raccomandate. È ben tollerata dalla maggior parte dei tipi di pelle, comprese le pelli sensibili. Pratiche di approvvigionamento e formulazione responsabili sono essenziali per garantire che l'ingrediente sia privo di contaminanti nocivi e prodotto in modo sostenibile.

Molecular Formula  C₁₅H₁₀O₅

Molecular Weight  270.24 g/mol

CAS     520-36-5

UNII    7V515PI7F6

EC Number  208-292-3

DTXSID6022391

Synonyms:

Apigenol

Versulin

Bibliografia__________________________________________________________________________

(1) Salehi B, Venditti A, Sharifi-Rad M, Kręgiel D, Sharifi-Rad J, Durazzo A, Lucarini M, Santini A, Souto EB, Novellino E, Antolak H, Azzini E, Setzer WN, Martins N. The Therapeutic Potential of Apigenin. Int J Mol Sci. 2019 Mar 15;20(6):1305. doi: 10.3390/ijms20061305.

Abstract. Several plant bioactive compounds have exhibited functional activities that suggest they could play a remarkable role in preventing a wide range of chronic diseases. The largest group of naturally-occurring polyphenols are the flavonoids, including apigenin. The present work is an updated overview of apigenin, focusing on its health-promoting effects/therapeutic functions and, in particular, results of in vivo research. In addition to an introduction to its chemistry, nutraceutical features have also been described. The main key findings from in vivo research, including animal models and human studies, are summarized. The beneficial indications are reported and discussed in detail, including effects in diabetes, amnesia and Alzheimer's disease, depression and insomnia, cancer, etc. Finally, data on flavonoids from the main public databases are gathered to highlight the apigenin's key role in dietary assessment and in the evaluation of a formulated diet, to determine exposure and to investigate its health effects in vivo.

(2) Yoon JH, Kim MY, Cho JY. Apigenin: A Therapeutic Agent for Treatment of Skin Inflammatory Diseases and Cancer. Int J Mol Sci. 2023 Jan 12;24(2):1498. doi: 10.3390/ijms24021498. 

Abstract. The skin is the main barrier between the body and the environment, protecting it from external oxidative stress induced by ultraviolet rays. It also prevents the entrance of infectious agents such as viruses, external antigens, allergens, and bacteria into our bodies. An overreaction to these agents causes severe skin diseases, including atopic dermatitis, pruritus, psoriasis, skin cancer, and vitiligo. Members of the flavonoid family include apigenin, quercetin, luteolin, and kaempferol. Of these, apigenin has been used as a dietary supplement due to its various biological activities and has been shown to reduce skin inflammation by downregulating various inflammatory markers and molecular targets. In this review, we deal with current knowledge about inflammatory reactions in the skin and the molecular mechanisms by which apigenin reduces skin inflammation.

Naponelli V, Rocchetti MT, Mangieri D. Apigenin: Molecular Mechanisms and Therapeutic Potential against Cancer Spreading. Int J Mol Sci. 2024 May 20;25(10):5569. doi: 10.3390/ijms25105569. 

Abstract. Due to its propensity to metastasize, cancer remains one of the leading causes of death worldwide. Thanks in part to their intrinsic low cytotoxicity, the effects of the flavonoid family in the prevention and treatment of various human cancers, both in vitro and in vivo, have received increasing attention in recent years. It is well documented that Apigenin (4',5,7-trihydroxyflavone), among other flavonoids, is able to modulate key signaling molecules involved in the initiation of cancer cell proliferation, invasion, and metastasis, including JAK/STAT, PI3K/Akt/mTOR, MAPK/ERK, NF-κB, and Wnt/β-catenin pathways, as well as the oncogenic non-coding RNA network. Based on these premises, the aim of this review is to emphasize some of the key events through which Apigenin suppresses cancer proliferation, focusing specifically on its ability to target key molecular pathways involved in angiogenesis, epithelial-to-mesenchymal transition (EMT), maintenance of cancer stem cells (CSCs), cell cycle arrest, and cancer cell death.

(3) Charrière K, Schneider V, Perrignon-Sommet M, Lizard G, Benani A, Jacquin-Piques A, Vejux A. Exploring the Role of Apigenin in Neuroinflammation: Insights and Implications. Int J Mol Sci. 2024 May 6;25(9):5041. doi: 10.3390/ijms25095041. 

Abstract. Neuroinflammation, a hallmark of various central nervous system disorders, is often associated with oxidative stress and neuronal or oligodendrocyte cell death. It is therefore very interesting to target neuroinflammation pharmacologically. One therapeutic option is the use of nutraceuticals, particularly apigenin. Apigenin is present in plants: vegetables (parsley, celery, onions), fruits (oranges), herbs (chamomile, thyme, oregano, basil), and some beverages (tea, beer, and wine). This review explores the potential of apigenin as an anti-inflammatory agent across diverse neurological conditions (multiple sclerosis, Parkinson's disease, Alzheimer's disease), cancer, cardiovascular diseases, cognitive and memory disorders, and toxicity related to trace metals and other chemicals. Drawing upon major studies, we summarize apigenin's multifaceted effects and underlying mechanisms in neuroinflammation. Our review underscores apigenin's therapeutic promise and calls for further investigation into its clinical applications.

(4) Thomas SD, Jha NK, Jha SK, Sadek B, Ojha S. Pharmacological and Molecular Insight on the Cardioprotective Role of Apigenin. Nutrients. 2023 Jan 12;15(2):385. doi: 10.3390/nu15020385. PMID: 36678254; 

Abstract. Apigenin is a naturally occurring dietary flavonoid found abundantly in fruits and vegetables. It possesses a wide range of biological properties that exert antioxidant, anti-inflammatory, anticancer, and antibacterial effects. These effects have been reported to be beneficial in the treatment of atherosclerosis, stroke, hypertension, ischemia/reperfusion-induced myocardial injury, and diabetic cardiomyopathy, and provide protection against drug-induced cardiotoxicity. These potential therapeutic effects advocate the exploration of the cardioprotective actions of apigenin. This review focuses on apigenin, and the possible pharmacological mechanisms involved in the protection against cardiovascular diseases. We further discuss its therapeutic uses and highlight its potential applications in the treatment of various cardiovascular disorders. Apigenin displays encouraging results, which may have implications in the development of novel strategies for the treatment of cardiovascular diseases. With the commercial availability of apigenin as a dietary supplement, the outcomes of preclinical studies may provide the investigational basis for future translational strategies evaluating the potential of apigenin in the treatment of cardiovascular disorders. Further preclinical and clinical investigations are required to characterize the safety and efficacy of apigenin and establish it as a nutraceutical as well as a therapeutic agent to be used alone or as an adjuvant with current drugs.

(5) Shukla S, Bhaskaran N, Babcook MA, Fu P, Maclennan GT, Gupta S. Apigenin inhibits prostate cancer progression in TRAMP mice via targeting PI3K/Akt/FoxO pathway. Carcinogenesis. 2014 Feb;35(2):452-60. doi: 10.1093/carcin/bgt316.

Abstract. Forkhead box O (FoxO) transcription factors play an important role as tumor suppressor in several human malignancies. Disruption of FoxO activity due to loss of phosphatase and tensin homolog and activation of phosphatidylinositol-3 kinase (PI3K)/Akt are frequently observed in prostate cancer. Apigenin, a naturally occurring plant flavone, exhibits antiproliferative and anticarcinogenic activities through mechanisms, which are not fully defined. In the present study, we show that apigenin suppressed prostate tumorigenesis in transgenic adenocarcinoma of the mouse prostate (TRAMP) mice through the PI3K/Akt/FoxO-signaling pathway. Apigenin-treated TRAMP mice (20 and 50 μg/mouse/day, 6 days/week for 20 weeks) exhibited significant decrease in tumor volumes of the prostate as well as completely abolished distant organ metastasis. Apigenin treatment resulted in significant decrease in the weight of genitourinary apparatus (P < 0.0001), dorsolateral (P < 0.0001) and ventral prostate (P < 0.028), compared with the control group. Apigenin-treated mice showed reduced phosphorylation of Akt (Ser473) and FoxO3a (Ser253), which correlated with its increased nuclear retention and decreased binding of FoxO3a with 14-3-3. These events lead to reduced proliferation as assessed by Ki-67 and cyclin D1, along with upregulation of FoxO-responsive proteins BIM and p27/Kip1. Complementing in vivo results, similar observations were noted in human prostate cancer LNCaP and PC-3 cells after apigenin treatment. Furthermore, binding of FoxO3a with p27/Kip1 was markedly increased after 10 and 20 μM apigenin treatment resulting in G0/G1-phase cell cycle arrest, which was consistent with the effects elicited by PI3K/Akt inhibitor, LY294002. These results provide convincing evidence that apigenin effectively suppressed prostate cancer progression, at least in part, by targeting the PI3K/Akt/FoxO-signaling pathway.

Hnit SST, Yao M, Xie C, Bi L, Wong M, Liu T, De Souza P, Li Z, Dong Q. Apigenin impedes cell cycle progression at G2 phase in prostate cancer cells. Discov Oncol. 2022 Jun 7;13(1):44. doi: 10.1007/s12672-022-00505-1. 

(6) Waheed A, Zameer S, Ashrafi K, Ali A, Sultana N, Aqil M, Sultana Y, Iqbal Z. Insights into Pharmacological Potential of Apigenin through Various Pathways on a Nanoplatform in Multitude of Diseases. Curr Pharm Des. 2023;29(17):1326-1340. doi: 10.2174/1381612829666230529164321.