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WO2024016142A1 - Utilisation d'une composition de bergaptène, de quercétine et de flavone dans la préparation d'un médicament pour le traitement du cancer - Google Patents

Utilisation d'une composition de bergaptène, de quercétine et de flavone dans la préparation d'un médicament pour le traitement du cancer Download PDF

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Publication number
WO2024016142A1
WO2024016142A1 PCT/CN2022/106383 CN2022106383W WO2024016142A1 WO 2024016142 A1 WO2024016142 A1 WO 2024016142A1 CN 2022106383 W CN2022106383 W CN 2022106383W WO 2024016142 A1 WO2024016142 A1 WO 2024016142A1
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Prior art keywords
cancer
bergamot
quercetin
lactone
preparation
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PCT/CN2022/106383
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English (en)
Chinese (zh)
Inventor
张新勇
王海波
郭振超
鲁佳雯
窦金凤
周丽丽
方艳夕
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Anhui University of Science and Technology
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Anhui University of Science and Technology
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Priority to PCT/CN2022/106383 priority Critical patent/WO2024016142A1/fr
Publication of WO2024016142A1 publication Critical patent/WO2024016142A1/fr
Anticipated expiration legal-status Critical
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
    • A61K31/37—Coumarins, e.g. psoralen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Definitions

  • the present invention relates to the technical field of anti-cancer drug preparation, and in particular to the application of a composition of bergamot lactone and quercetin flavonoids in the preparation of cancer treatment drugs.
  • Radiochemotherapy has little effect in clinical use due to its major side effects.
  • the probability of recurrence and metastasis is still relatively high. Therefore, patients need regular examinations and appropriate adjustments to their lifestyle and diet. .
  • Standard postoperative adjuvant chemotherapy and radiotherapy can reduce the recurrence and metastasis of cancer or prolong the time of recurrence and metastasis, but there is still the possibility of recurrence and metastasis.
  • cancer patients After surgery, cancer patients need to be reviewed every 3 to 4 months, given anti-cancer drugs intravenously, and hospitalized for about 10 days. This frequency should be maintained for at least two years; after two years, it can be changed to once every six months, and then continued Three years, so a total of five years of treatment is required.
  • cancer surgery combined with radiotherapy and chemotherapy, the body is very weak. Generally speaking, it is difficult to prevent recurrence and restore health after cancer surgery.
  • the object of the present invention is to provide the application of the composition of bergamot lactone and quercetin flavonoids in the preparation of cancer treatment drugs to solve the problems existing in the prior art.
  • the present invention provides the following solutions:
  • One of the objects of the present invention is to provide the application of the composition of bergamot lactone and quercetin flavonoid in the preparation of cancer treatment drugs.
  • the bergamot lactone is a natural substance isolated from the hand of bergamot; the quercetin flavonoid It is a natural substance isolated from Sophora japonica;
  • the mass ratio of bergamot lactone and quercetin flavonoids in the composition of bergamot lactone and quercetin flavonoids is 1:3 to 8;
  • the cancer is lung cancer, liver cancer, cervical cancer or prostate cancer;
  • the preparation method of bergamot lactone includes the following steps:
  • the application also includes the preparation of drugs for auxiliary treatment of tumors and the preparation of anti-cancer reversal agents, that is, the application of drugs in enhancing the efficacy and reducing toxicity of tumor chemotherapy drugs, sensitizing tumor radiotherapy, and enhancing the immune function of the body.
  • the therapeutically effective dose of the combination of bergamot lactone and quercetin flavonoids is 5 to 50 mg/kg.
  • the therapeutically effective dose of the combination of bergamot lactone and quercetin flavonoids is 10 to 25 mg/kg.
  • the second object of the present invention is to provide an anti-cancer drug, which uses a composition of bergamot lactone and quercetin flavonoids as active ingredients, and also contains a pharmaceutically acceptable carrier.
  • the bergamot lactone is isolated from bergamot. Obtained natural substances;
  • the quercetin flavonoid is a natural substance isolated from Sophora japonica
  • the mass ratio of bergamot lactone and quercetin flavonoids in the composition of bergamot lactone and quercetin flavonoids is 1:3 to 8;
  • the cancer is lung cancer, liver cancer, cervical cancer or prostate cancer.
  • the therapeutically effective amount of the composition of bergamot lactone and quercetin flavonoids is 2.5-100 mg/kg, and the purity is greater than 80%.
  • the bergamot lactone involved in the present invention is a high-purity natural compound bergamot lactone isolated from the fruit of the Rutaceae plant Citrus medica L. var. sarcodactylis Swingle. Its structures are:
  • Quercetin flavonoid is a natural substance isolated from Sophora japonica. Its structures are:
  • Quercetin (molecular formula: C 15 H 10 O 7 ).
  • the pharmaceutically acceptable carrier includes one or more of fillers, binders, disintegrants, lubricants, flavoring agents and antioxidants.
  • the filler includes mannitol, lactose or polyethylene glycol; the binder includes starch or microcrystalline cellulose; the disintegrant includes carboxymethyl cellulose or low-substituted hydroxypropyl cellulose. ; The lubricant includes talc or magnesium stearate.
  • the mass ratio of the filler to the antioxidant is 2 to 5:1.
  • anti-cancer drug dosage forms are oral preparations, injection oil preparations or external preparations.
  • the oral preparation is a tablet, capsule, sustained-release tablet or dropping pill
  • the external preparation is a cream, ointment, oil or glycerin preparation.
  • the preparation method of the tablet is: weigh 10 to 70% of the composition of bergamot lactone and quercetin flavonoids in terms of mass percentage, add 30 to 90% of an acceptable carrier, and stir and mix. Granulate, dry at 60-70°C for 24 hours, and press to obtain the tablets, each tablet containing 2.5-20 mg of bergamot lactone and quercetin flavonoids, preferably 2.5 mg, 5 mg, 10 mg, 15 mg and 20 mg.
  • the preparation method of the capsule is: weighing 10 to 70% of the composition of bergamot lactone and quercetin flavonoids in terms of mass percentage, adding 30 to 90% of an acceptable carrier, and stirring and mixing to prepare the capsule.
  • the capsules are dried at 60 to 70° C. for 24 hours, and then filled into empty capsule shells to obtain the capsules.
  • Each capsule contains 2 to 20 mg of bergamot lactone and quercetin flavonoids.
  • the preparation method of the injection oil is: weighing 1 to 10% of the composition of bergamot lactone and quercetin flavonoids and 90 to 99% of the injection oil in terms of mass percentage, and then packaging.
  • the injection oil is prepared by sterilization, and the injection oil is soybean oil or camellia oil for injection.
  • the preparation method of the dripping pills is: weighing 10 to 60% of the composition of bergamot lactone and quercetin flavonoids in terms of mass percentage, adding 40 to 90% of an acceptable carrier, and heating and melting. , the melting temperature is 100-150°C, the raw materials and auxiliary materials are fully mixed and dropped into pills to obtain the dripping pills, each of which contains 2.5-20 mg of the composition of bergamot lactone and quercetin flavonoids.
  • composition containing bergamot lactone and quercetin flavonoids of the present invention shows that it has obvious pharmacological activities such as anti-lung cancer, anti-liver cancer, anti-cervical cancer, etc.
  • the composition is expected to be developed into a low-toxicity, high-efficiency and multi-functional New cancer prevention and treatment drugs, anti-cancer reversal agents and tumor auxiliary treatment drugs with pharmacological effects of natural traditional Chinese medicine ingredients.
  • the material-liquid ratio of chayote powder and ethanol solution is 0.03g/mL.
  • the sample solution is directly passed through the X-8 macroporous adsorption resin.
  • the amount of raw solution is 110% of the static saturated adsorption capacity of bergamot lactone by the macroporous adsorption resin; the column diameter and column height ratio of the macroporous adsorption resin is 1:5.
  • Quercetin flavonoid extraction method Add 200 ml of 0.4% boric acid aqueous solution to 20 g of sophora rice powder, and adjust the pH value to 8 to 9 with milk of lime. Stir and extract under slightly boiling conditions for 30 minutes. Adjust the filtrate to a pH value of 2 to 3 with concentrated hydrochloric acid. Let it stand for 12 hours and then centrifuge. The precipitate is washed once with concentrated hydrochloric acid of a pH value of 1 to 2, and washed with distilled water until neutral. The precipitate is washed with The crude rutin product was obtained by vacuum drying at 65°C. After purifying rutin, take 1 g, use 80 ml of 2% sulfuric acid solution, and heat and reflux for 90 minutes to convert it into quercetin flavonoids.
  • Preparation of tablets In terms of mass percentage, weigh 50wt.% of the composition of bergamot lactone and quercetin flavonoids (the mass ratio of bergamot lactone and quercetin flavonoids in the composition is 1:5), Add 50wt.% mannitol, starch, carboxymethyl cellulose, and talc (the mass ratio of mannitol: starch: carboxymethyl cellulose: talc is 1:2:3:2), stir, mix and granulate. Dry at 70°C for 24 hours and press into tablets. Each tablet contains 10 mg of bergamot lactone and quercetin flavonoids.
  • Preparation of capsules In terms of mass percentage, weigh 10 wt.% of the composition of bergamot lactone and quercetin flavonoids (the mass ratio of bergamot lactone and quercetin flavonoids in the composition is 1:5), and add 90wt.% lactose, microcrystalline cellulose, low-substituted hydroxypropyl cellulose, magnesium stearate and flavoring (lactose, microcrystalline cellulose, low-substituted hydroxypropyl cellulose, magnesium stearate and flavoring
  • the mass ratio of the agent is 1: 2:1:2:1), stir, mix and granulate, dry at 70°C for 24 hours, and then fill into empty capsule shells.
  • Each capsule contains bergamot lactone and quercetin flavonoids. 5mg.
  • the flavoring agent is aspartame and lemon essence with a mass ratio of 40:1.
  • Preparation of oil In terms of mass percentage, weigh 10 wt.% of the composition of bergamot lactone and quercetin flavonoids (the mass ratio of bergamot lactone and quercetin flavonoids in the composition is 1:5) and Mix 90wt.% injection oil, pack and sterilize to prepare the oil.
  • Preparation of dripping pills In terms of mass percentage, weigh 60wt.% of the composition of bergamot lactone and quercetin flavonoids (the mass ratio of bergamot lactone and quercetin flavonoids in the composition is 1:5), Add 40wt.% polyethylene glycol and antioxidant (the mass ratio of polyethylene glycol and antioxidant is 4:1) for heating and melting. The melting temperature is 150°C. Drop it into pills. Each pill contains bergamot. Lactone and quercetin flavonoids 20mg.
  • the antioxidants are vitamin C and sodium metabisulfite with a mass ratio of 4:1.
  • composition of bergamot lactone and quercetin flavonoids has the following properties: it appears as light yellow needle-like crystals under a microscope and exhibits brown-yellow fluorescence under ultraviolet light.
  • the TLC ratio shift value Rf is: 0.538 (petroleum ether:ethyl acetate 8:2).
  • IR ⁇ KBr max (cm -1 ): 3370 (broad peak, OH), 1655 (keto group C O), 1600, 1560, 1510 (phenyl).
  • the invention discloses that a composition containing bergamot lactone and quercetin flavonoids (the mass ratio of bergamot lactone and quercetin flavonoids in the composition is 1:5) can be used to prepare anti-tumor drugs and anti-cancer reversal agents.
  • Applications, including anti-tumor activity include: applications in preparing drugs for the treatment of lung cancer, liver cancer, and cervical cancer.
  • Inoculate cells Take logarithmic growth phase cells, digest them with 0.02% EDTA, add RPMI-1640 solution containing 10 to 15% fetal calf serum, dilute the cells into a single cell suspension, count and adjust the cell number, and Inoculate into a 96-well plate, and culture the inoculated cells in a 37°C carbon dioxide incubator for 24 hours.
  • MTT MTT is dissolved in RPMI-1640, and 50ul is added to each well. Then place it at 37°C and continue culturing for 4 hours before taking it out.
  • Hydroxycamptothecin produced by Hubei Huangshi Feiyun Pharmaceutical Co., Ltd.
  • Lung adenocarcinoma spc-A-1 tumor line was provided by Shanghai Cancer Institute.
  • DR-70 kit Lung cancer enzyme-linked quantitative kit, purchased from Beijing Medic Corporation.
  • spc-A-1 cells were routinely cultured in cells containing 12% newborn calf serum, 0.25mmol/L Hepes, 100U/ml penicillin and 100U/ml chain In RP-MI1640 culture medium containing mycomycin, adjust the cell number to 5 ⁇ 10 5 /ml. After trypan blue staining, the cell viability was greater than 95%. Take 0.2ml of cell suspension and inoculate it subcutaneously on the back of nude mice.
  • Tumor inhibition experiment 50 nude mice were subcutaneously inoculated with lung adenocarcinoma spc-A-1 cells and randomly divided into 5 groups, namely the treatment group (positive control group), the tumor control group (negative control group) and the experimental group (I - Group III), 10 animals in each group.
  • the equivalent dose is 0.75mg/kg, 1.50mg/kg, 2.25mg/kg, and continue to administer for 10 days.
  • the tumor control group was not given any medication and was only injected with the same volume of normal saline; the treatment group (positive control group) was given intraperitoneal injection of hydroxycamptothecin (OPT) 1.5 mg/kg for 10 consecutive days. After stopping the drug, the animals were sacrificed, the tumors were separated, the tumor weight and body weight were measured using an electronic balance, and the changes in body weight were recorded.
  • OPT hydroxycamptothecin
  • tumor growth inhibition rate (1-average tumor weight of the test group/average tumor weight of the control group) ⁇ 100%.
  • DR-70 Tm for healthy people ⁇ 8ug/ml
  • Inhibiting the growth of lung adenocarcinoma spc-A-1 The combination of bergamot lactone and quercetin flavonoids has a significant inhibitory effect on lung adenocarcinoma spc-A-1 at a dose of 0.75 to 2.25 mg/kg. It shows that the combination of bergamot lactone and quercetin flavonoids can significantly inhibit the growth of lung adenocarcinoma spc-A-1 in Kunming mice at a dose of 0.75-2.25 mg/kg, and the high-dose group has a tumor inhibition rate of 2.25 mg/kg.
  • the positive control group significantly reduced the weight of mice, which was significantly different from that of the blank control group.
  • the effects of the three dosage groups of bergamot lactone and quercetin flavonoid composition on the body weight of mice were significantly different from those of the blank control group. No significant difference. It shows that hydroxycamptothecin (OPT) causes greater damage to tumor-bearing mice; while the combination of bergamot lactone and quercetin flavonoids has lower toxic and side effects, which is the difference between it and chemotherapy drugs.
  • the serum DR-70 levels in the three dosage groups of bergamot lactone and quercetin flavonoid combination were significantly reduced, indicating that the bergamot lactone and quercetin flavonoid combination has a certain inhibitory effect on the infiltration of cancer tissue into the body. .
  • mice 60 Kunming mice, half male and half female, weighing 20 ⁇ 2g, purchased from the Experimental Animal Center of Nanjing University of Traditional Chinese Medicine.
  • Liver cancer H22 tumor line was provided by Shanghai Cancer Institute.
  • liver cancer H 22 tumor-bearing mice The laboratory was disinfected with ultraviolet light for 3 hours before dissection, and several passage ascites cancer mice that had grown for 6-7 days were selected. After dislocation and sacrifice, the abdomen was disinfected with alcohol and the better-growing ascites was taken out. The cancer was diluted at a ratio of 1:2, and the cancer cell count was 5.2 ⁇ 10 7 /ml. It was inoculated into the armpit of the right upper limb of the mice, and 0.2ml was inoculated into each mouse.
  • mice inoculated with liver cancer cells H22 were randomly divided into 5 groups, namely the treatment group (positive control group), the tumor control group (negative control group) and the experimental group (groups I-III). Group of 10.
  • the equivalent dose is 0.75mg/kg, 1.50mg/kg, 2.25mg/kg, and continue to administer for 10 days.
  • the tumor control group was not given any medication and was only injected with the same volume of normal saline; the treatment group (positive control group) was given an intraperitoneal injection of cisplatin 4 mg/kg, and each animal was given 0.2 ml/d ip every 1 day, 3 times.
  • tumor growth inhibition rate (1-average tumor weight of test group/average tumor weight of control group) ⁇ 100%.
  • the composition of bergamot lactone and quercetin flavonoids has a significant inhibitory effect on liver cancer H 22 at a dose of 0.75 to 2.25 mg/kg. It shows that the combination of bergamot lactone and quercetin flavonoids can significantly inhibit the growth of Kunming mouse liver cancer H22 at a dose of 0.75-2.25 mg/kg, and the tumor inhibition rate of the medium-dose group at 1.50 mg/kg reached 62.13%.
  • the bergamot lactone and quercetin flavonoid compositions at doses of 0.75 mg/kg, 1.50 mg/kg, and 2.25 mg/kg can significantly inhibit the growth of liver cancer H 22 .
  • the positive control group significantly reduced the body weight, liver weight and immune indicators (spleen index and thymus index) of tumor-bearing mice, which was significantly different from the blank control group, while the combination of bergamot lactone and quercetin flavonoids There were no significant differences in these indicators between the object group and the blank control group. It shows that cisplatin causes great damage to the organs of tumor-bearing mice; while several dosage groups of bergamot lactone and quercetin flavonoid combinations have significant effects on the body weight, liver weight, spleen index and thymus index of tumor-bearing mice. There was no obvious change, indicating that the combination of bergamot lactone and quercetin flavonoids has low toxicity and high anti-tumor activity on tumors, which is a significant feature that is different from chemotherapy drugs.
  • mice 60 Kunming mice, half male and half female, weighing 20 ⁇ 2g, purchased from the Experimental Animal Center of Nanjing University of Traditional Chinese Medicine.
  • mice inoculated with cervical cancer U 14 were randomly divided into 5 groups, namely the treatment group (positive control group), the tumor control group (negative control group) and the experimental group (groups I-III). 10 per group.
  • the equivalent dose is 0.75mg/kg, 1.50mg/kg, 2.25mg/kg, and continue to administer for 10 days.
  • the tumor control group was not given any medication and was only injected with the same volume of normal saline; the treatment group (positive control group) was given intraperitoneal injection of cyclophosphamide (CPP) 20 mg/kg, and each animal was given 0.3 ml/d ip for 10 consecutive days. .
  • CPP cyclophosphamide
  • tumor growth inhibition rate (1-average tumor weight of the test group/average tumor weight of the control group) ⁇ 100%.
  • Inhibiting the growth of cervical cancer U 14 The combination of bergamot lactone and quercetin flavonoids at doses of 0.75 mg/kg, 1.50 mg/kg, and 2.25 mg/kg can significantly inhibit the growth of cervical cancer U 14 .
  • the low-dose group 0.75 mg/kg had the best tumor inhibitory effect, with a tumor inhibition rate of 60.62%, indicating that the combination of bergamot lactone and quercetin flavonoids has a certain dose selectivity in inhibiting different tumors; the positive control group cyclophosphate Amide (CPP) can significantly reduce the weight of tumor-bearing mice, while there is no significant difference between the bergamot lactone and quercetin flavonoid composition group and the blank control group.
  • CPP cyclophosphate Amide
  • cyclophosphamide has certain damage to tumor-bearing mice; while several dosage groups of bergamot lactone and quercetin flavonoid composition have no significant effect on the body weight of tumor-bearing mice, indicating that bergamot lactone and quercetin
  • the cortin flavonoid composition has the characteristics of low toxicity and high efficiency.

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Abstract

L'invention concerne l'utilisation d'une composition de bergaptène, de quercétine et de flavone dans la préparation d'un médicament pour le traitement du cancer. La présente invention se rapporte au domaine technique de la préparation de médicaments anticancéreux. La composition de bergaptène, de quercétine et de flavone de la présente invention présente une activité pharmacologique considérable dans la lutte contre le cancer du poumon, le cancer du foie, le cancer du col de l'utérus et d'autres maladies analogues. La composition devrait être mise au point pour devenir un nouveau médicament de prévention et de traitement des tumeurs, un agent déactivateur anticancéreux et un médicament pour la thérapie adjuvante des tumeurs, peu toxiques et très efficaces et qui contiennent des composants naturels de médecine traditionnelle chinoise aux effets pharmacologiques variés.
PCT/CN2022/106383 2022-07-19 2022-07-19 Utilisation d'une composition de bergaptène, de quercétine et de flavone dans la préparation d'un médicament pour le traitement du cancer Ceased WO2024016142A1 (fr)

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Citations (2)

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CN111110673A (zh) * 2020-01-20 2020-05-08 东莞市滨海湾中心医院 佛手柑内酯在制备治疗结直肠癌药物中的应用
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SUN JIA, ZHHAO DONG-GENG, WANG MING-YAN, ZHAO FENG-MING, XU DONG-QING, YE LI-HONG: "Influence of Quercetin on PI3K/AKT Signal Pathway of SMMC-7721 Hepatic Cancer Cells", CHINESE JOURNAL OF EXPERIMENTAL TRADITIONAL MEDICAL FORMULAE, ZHONGGUO ZHONGYI KEXUEYUAN ZHONGYAO YANJIUSUO, CN, vol. 18, no. 18, 20 September 2012 (2012-09-20), CN , pages 223 - 226, XP009552150, ISSN: 1005-9903 *
XIE SHU-HUAN; FENG MA-LI: "Advances in pharmacological action of bergamot lactone", HAINAN YIXUEYUAN XUEBAO = JOURNAL OF HAINAN MEDICAL UNIVERSITY, HAINAN YIXUEYUAN XUEBAO ZAZHISHE,JOURNAL PRESS OF HAINAN MEDICAL UNIVERSITY, CN, vol. 28, no. 24, 7 May 2021 (2021-05-07), CN , pages 1917 - 1920, XP009552147, ISSN: 1007-1237 *
ZHAO LI-PING; WANG CHAO; TIAN NAN; FAN CHUN-LEI: "Effect of Bergapten on Apoptosis of HepG2 and Hep3B Cells Through PI3K/Akt Pathway", CHINESE JOURNAL OF EXPERIMENTAL TRADITIONAL MEDICAL FORMULAE, ZHONGGUO ZHONGYI KEXUEYUAN ZHONGYAO YANJIUSUO, CN, vol. 26, no. 6, 13 December 2019 (2019-12-13), CN , pages 73 - 78, XP009552151, ISSN: 1005-9903 *

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