CN107362238B - Schima superba extract and application thereof - Google Patents
Schima superba extract and application thereof Download PDFInfo
- Publication number
- CN107362238B CN107362238B CN201710495201.7A CN201710495201A CN107362238B CN 107362238 B CN107362238 B CN 107362238B CN 201710495201 A CN201710495201 A CN 201710495201A CN 107362238 B CN107362238 B CN 107362238B
- Authority
- CN
- China
- Prior art keywords
- extract
- schima superba
- compound
- layer
- schima
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- 241000610442 Schima superba Species 0.000 title claims abstract description 37
- 239000000284 extract Substances 0.000 title claims abstract description 28
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- 150000001875 compounds Chemical class 0.000 claims description 44
- 229940079593 drug Drugs 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 13
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
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- MWOHZWYDIQDYSO-CKBORDAOSA-N sanchakasaponin F Natural products CC=C(C)/C(=O)O[C@H]1[C@H](OC(=O)C(=C/C)C)[C@]2(CO)[C@H](O)[C@H](O)[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@@H]([C@@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O[C@@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)[C@H]6O[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O)C(=O)O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2CC1(C)C MWOHZWYDIQDYSO-CKBORDAOSA-N 0.000 description 3
- KHFDIHQNZXOTAA-UHFFFAOYSA-N sasanquasaponins III Natural products CC1(C)C2CCC3(C)C4(C)C(O)C(O)C5(CO)C(OC(=O)C(C)=CC)CC(C)(C)CC5C4=CCC3C2(C)CCC1OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(C(O)=O)C(O)C1OC1OC(CO)C(O)C(O)C1OC1OC(C)C(O)C(O)C1O KHFDIHQNZXOTAA-UHFFFAOYSA-N 0.000 description 3
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
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- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 2
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 210000000214 mouth Anatomy 0.000 description 1
- WWJFFVUVFNBJTN-UHFFFAOYSA-N neopolyoxin C Natural products C=1C=C(O)C=NC=1C(O)C(C)C(N)C(=O)NC(C(O)=O)C(C(C1O)O)OC1N1C=CC(=O)NC1=O WWJFFVUVFNBJTN-UHFFFAOYSA-N 0.000 description 1
- WWJFFVUVFNBJTN-VHDFTHOZSA-N nikkomycin Z Chemical compound N1([C@@H]2O[C@@H]([C@H]([C@H]2O)O)[C@H](NC(=O)[C@@H](N)[C@H](C)[C@H](O)C=2N=CC(O)=CC=2)C(O)=O)C=CC(=O)NC1=O WWJFFVUVFNBJTN-VHDFTHOZSA-N 0.000 description 1
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- MWOHZWYDIQDYSO-UHFFFAOYSA-N yuchasaponin A Natural products C12CC(C)(C)C(OC(=O)C(C)=CC)C(OC(=O)C(C)=CC)C2(CO)C(O)C(O)C(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(C(O)=O)C(O)C1OC1OC(CO)C(O)C(O)C1OC1OC(C)C(O)C(O)C1O MWOHZWYDIQDYSO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/82—Theaceae (Tea family), e.g. camellia
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Botany (AREA)
- Biotechnology (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Reproductive Health (AREA)
- Physiology (AREA)
- Alternative & Traditional Medicine (AREA)
- Urology & Nephrology (AREA)
- Gynecology & Obstetrics (AREA)
- Medical Informatics (AREA)
- Nutrition Science (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses application of a schima superba extract in preparing a medicine or a health-care product or a cosmetic with an antifungal effect. The part of the schima superba is preferably roots and/or stems. The extract comprises water extract or ethanol extract, and the ethanol is preferably 95% ethanol.
Description
Technical Field
The invention relates to the field of medicinal materials, in particular to a schima superba extract and application thereof.
Background
Fungal infections, particularly deep fungal infections and fungal resistance, are major problems facing human health and are one of the leading causes of human morbidity and mortality. In recent years, with the wide use of immunosuppressive agents, radiotherapy and chemotherapy of tumors are widely carried out, particularly, the incidence of fungal infection, particularly deep fungal infection, is rapidly increased due to the increasing number of aids patients. Statistical data show that in a certain three hospitals in China, the death rate caused by fungal infection in hospitals reaches 12.88% between 2012 and 2014. Fungal infections have been one of the leading causes of death in patients with the above-mentioned serious diseases of immune hypofunction. When the antifungal medicines are widely applied to clinic for a long time, the drug resistance phenomenon of fungi is more and more common, the drug resistance degree is higher and higher, and the drug resistance becomes the main reason of failure of clinical antifungal treatment. Candida is the most common deep pathogenic fungus and has become a major cause of pathogenic fungal infections of the respiratory, digestive and urinary tracts. Among the secondary infections in aids patients, candida infections are often the most common and first to occur. In addition, the morbidity and mortality associated with advanced systemic candida infections and local infections have also become major health problems. According to studies, nearly 70% of women have a history of vaginal candida infections, with repeated infections occurring in 20% of them. In this repeatedly infected population, about half of the patients have multiple attacks per year. The most common pathogenic bacteria in the candida are candida albicans, and the research results in recent years in China show that the candida albicans accounts for 37.1-76.5 percent of clinically isolated pathogenic bacteria and 64.8-86.3 percent of clinically isolated candida, and the visible candida albicans is the most important invasive opportunistic pathogenic fungi.
The treatment of fungal infections has hitherto been completely dependent on drug therapy. At present, the antifungal drugs used clinically have limited structural types (mainly polyene amphotericin B and derivatives thereof, azole drugs, echinocandins, nikkomycin and the like), relatively single action mechanism and target points, and various toxic and side effects and increasingly severe drug resistance problems of the antifungal drugs. Therefore, there is still an urgent need for new antifungal agents, especially those with new structural types, new mechanisms of action or (and) targets of action.
The Schima superba is root bark of Schima superba (Schima Reinw.) belonging to Schima of Theaceae (Theaceae). The schima superba is also called lotus, mugwort and the like, is subtropical evergreen big arbor and is mainly distributed in Guangdong, Fujian, Zhejiang, Jiangsu, Anhui, Yunnan and the like. The plant is a toxic plant recorded in a Chinese plant map database. In folk Zhejiang, the stem bark of Zhejiang was boiled with kusnezoff monkshood root, and the decoction was applied to arrowheads to kill wild animals such as tigers. When people touch the stem skin, symptoms such as red swelling, itching and the like can be generated. The schima superba root bark is pungent, warm and toxic, has the efficacy of clearing heat and removing toxicity, and is used for treating furuncle, nameless sores and the like by external application. In the prior art, no report is provided about the antibacterial biological activity of the schima superba extract.
Disclosure of Invention
The invention aims to provide application of an ethanol extract of a schima superba rhizome in preparation of a drug or a health-care product or a cosmetic with an antifungal effect.
Wherein, the medicine comprises a washing product.
Wherein, the washing products include, but are not limited to, washing products for oral cavity, vaginitis or urinary tract infection, and the like.
In one embodiment, the preparation method of the ethanol extract of schima superba is as follows: 1 part of dry coarse powder of the schima superba, heating and refluxing for 2 to 4 times by using 6 to 10 times of ethanol, mixing extracting solutions each time for 1 to 3 hours, and concentrating under reduced pressure to obtain a total extract.
Wherein, the schima superba is the root and/or stem of the schima superba.
Wherein the ethanol extract is a 95% ethanol extract.
An antifungal agent, characterized by: the medicine contains an ethanol extract of the schima superba.
Wherein the ethanol extract is a 95% ethanol extract.
Compared with the prior art, the invention has the advantages that:
aiming at the defects of the current antifungal drug species, provides the application of the schima superba extract as the antibacterial drug. The experimental results of the examples show that the schima superba extract has good antibacterial effect.
Drawings
FIG. 1 shows the results of example 1, wherein the bacteriostatic results of the schima superba alcohol extract are shown in the left; the right part shows the bacteriostatic result of the water extract of schima superba.
FIG. 2 shows the bacteriostatic effect of each compound (100. mu.g) in example 4.
Detailed Description
Example 1
In vitro anti-candida albicans activity test for schima superba extract
The experiment takes candida albicans sensitive strains and candida albicans drug-resistant strains as indicator bacteria, and the antibacterial activity of the schima superba extract is determined by adopting an oxford cup method in-vitro drug sensitivity experiment.
Water extract of Schima superba
Crushing the schima superba root bark properly, sieving by a 40-mesh sieve, taking 200g of the schima superba root bark, adding 500mL of water, heating, refluxing and extracting for 3 times, each time for 1 hour, combining extracting solutions, and concentrating under reduced pressure to obtain 18.6g of extract.
Schima superba alcohol extract
Crushing the root bark of schima superba appropriately, sieving with a 40-mesh sieve, taking 200g of the crushed schima superba, adding 500mL of 95% ethanol water, heating, refluxing and extracting for 3 times, each time for 1 hour, combining extracting solutions, and concentrating under reduced pressure to obtain 12.3g of extract.
Experimental methods
Activation of the strain: candida albicans stored in a refrigerator at-80 ℃ is placed on a culture medium plate and cultured in a thermostat at 34 ℃ for 48 hours to activate the Candida albicans.
Oxford cup method in vitro drug sensitivity experiment
Preparation of sample solution: about 20mg of the extract was taken and precisely weighed. Dissolving the water extract of Schima superba with appropriate amount of water to obtain a concentration of 200mg/mL, and dissolving the alcohol extract of Schima superba with appropriate amount of water to obtain a concentration of 200 mg/mL.
Sucking 1mL of the solution to be tested in an Oxford cup by a pipette, and placing the solution in the prepared Sabouraud's solid culture medium (the bacterial content is about 2 multiplied by 10) containing the Candida albicans6mu.L), using water and methanol as blank control, culturing at constant temperature of 34 ℃ for 24h, taking out and measuring the diameter of the inhibition zone, and recording data.
Example 2
4.5kg of dry coarse powder of the schima superba stems is heated and refluxed for 3 times by 95% ethanol (8 times of the amount of the medicinal materials) for 2 hours each time, and the extracting solutions for 3 times are combined and concentrated under reduced pressure to obtain 200g of total extract.
Dissolving the total extract with 50% methanol water, dispersing, sequentially extracting with petroleum ether, chloroform, ethyl acetate and n-butanol to obtain 50g petroleum ether layer, 35g chloroform layer, 22g ethyl acetate layer, 20g n-butanol layer and 45g water layer. The ethyl acetate fraction was subjected to silica gel column chromatography using chloroform-methanol system (100: 0; 90: 10; 80: 20; 70: 30; 60: 40; 50: 50; 30: 70; 0:100) to obtain Fr.1-20 fractions. Wherein, the fraction Fr.12(3.3g) is subjected to ODS reverse phase column chromatography (180g, 3.5cm x40 cm) in a water-methanol system (80: 20; 70: 30; 60: 40; 40: 60; 20: 80; 0:100) to obtain the fraction Fr.12-1-13. Then the compound is obtained by preparative or semi-preparative high performance liquid chromatography.
Semi-preparative high performance liquid chromatography is performed on fraction Fr.12-10 with a flow rate of 3ml/min in a 45% acetonitrile-water system to obtain compound SS-9(50 mg);
fraction Fr.12-12 by HPLC with 37% acetonitrile-water system at flow rate of 7ml/min to obtain compound SS-10(13 mg);
fraction Fr.12-9 high performance liquid chromatography was performed in a 45% acetonitrile-water system at a flow rate of 7ml/min to obtain compound SS-14(13mg) and compound SS-15(6 mg).
Example 3
1. Structure identification of compound sasanquasaponin III (SS-9)
A white amorphous powder of a crystalline substance,
(c 0.30, MeOH). The reactions of Liebermann-Burchard and Molish are positive, and the color development of concentrated sulfuric acid-vanillin is red (TLC), which is presumed to be a triterpene saponin compoundA compound (I) is provided. ESI-MS M/z1241.6[ M + Na ]]+Suggesting that the molecular weight may be 1218, binding1H NMR and13the C NMR spectrum assumed that the compound SS-9 has the formula C59H94O26。
1The H NMR spectrum showed a methyl hydrogen signal of 7 degreesH 0.81(3H,s,H-25),1.03(3H,s,H-26),1.08(3H,s,H-29),1.08(3H,s,H-24),1.30(3H,s,H-23),1.43(3H,s,H-30),1.85(3H,s,H-27)]1 alkene hydrogen signal: (H5.48, br.s), 4 terminal hydrogen signals [ alpha ], [ beta ] -n-butyl ] nH4.92(d, J ═ 7.1Hz, H-1 '), 5.95(d, J ═ 7.6Hz, H-1"),6.19(d, J ═ 7.0Hz, H-1 '"), and 6.26(br.s, H-1 ' ")]A characteristic group of angeloyl hydrogen signalsH1.88(s,H3-5″″′),2.05(d,J＝6.6Hz,H3-4″″′),5.86(d,J＝6.6Hz,H-3″″′)]。13C NMR spectrum (Table 1) showed that Compound SS-9 had 59 carbons, including 7 corner methyl carbons ((R))C33.6,27.8,25.2,21.4,18.2,16.7 and 16.0), 4 olefinic carbons ((ii)C144.5,136.8,129.5 and 124.9), 4 terminal carbons ((iii)C105.4,102.6,102.3 and 101.0).
Comparing the NMR data of compound SS-9 with that of the compound sasanquasaponin III reported in the literature, the two are found to be substantially identical, and therefore, the compound SS-9 is identified as sasanquasaponin III.
2. Structure identification of compound maetenoside B (SS-10)
A white amorphous powder of a crystalline substance,
(c 0.25, MeOH). The reactions of Liebermann-Burchard and Molish are positive, and the color development of concentrated sulfuric acid-vanillin is red (TLC), which is presumed to be a triterpenoid saponin compound. ESI-MS M/z1225.7[ M + Na ]]+Suggesting that the molecular weight may be 1202, binding1H NMR and13the C NMR spectrum assumed that the compound SS-10 has the formula C59H94O25。
1The H NMR spectrum showed a methyl hydrogen signal of 7 degreesH 0.77(3H,s,H-25),0.85(3H,s,H-26),1.03(3H,s,H-29),1.06(3H,s,H-24),1.14(3H,s,H-23),1.26(3H,s,H-30),1.94(3H,s,H-27)]1 alkene hydrogen signal: (H5.37, br.s), 4 terminal hydrogen signals [ alpha ], [ beta ] -n-butyl ] orH4.84(d, J ═ 7.0Hz, H-1 '), 5.91(d, J ═ 7.3Hz, H-1"),5.92(d, J ═ 7.1Hz, H-1'"), and 6.19(br.s, H-1 "")]A characteristic group of angeloyl hydrogen signalsH1.85(s,H3-5″″′),2.07(d,J＝6.5Hz,H3-4″″′),5.85(d,J＝6.5Hz,H-3″″′)]。13C NMR spectrum (Table 1) showed 59 carbons, including 7 corner methyl carbons ((C))C34.0,28.2,27.8,25.3,16.8,16.7 and 16.2), 4 olefinic carbons (CC144.3,137.1,130.0 and 123.7), 4 terminal carbons ((iii)C105.7,102.9,102.6 and 101.5).
Comparing the NMR data of the compound SS-10 with that of the compound maetenoside B reported in the literature, the two are basically consistent, and therefore, the compound is identified as maetenoside B.
Table 3-8 13C NMR data of SS-9and SS-10
Spectra were measured in C5D5N at 100MHz for 13C NMR.
3. Structure identification of Compound sanchakasaponin F (SS-14)
A white amorphous powder of a crystalline substance,
(c 0.20, MeOH). Liebermann-Burchard and Molish reactionThe triterpene saponins are supposed to be positive and the concentrated sulfuric acid-vanillin is supposed to be red (TLC) in color. ESI-MS M/z1339.4[ M + Na ]]+Suggesting that the molecular weight may be 1316, binding1H NMR and13the C NMR spectrum assumed that the compound SS-14 has the formula C64H100O28。
Of compound SS-141The H NMR spectrum showed a 7-angle methyl hydrogen signal [ alpha ]H 0.80(3H,s,H-25),1.00(3H,s,H-26),1.05(3H,s,H-24),1.09(3H,s,H-29),1.12(3H,s,H-23),1.31(3H,s,H-30),1.84(3H,s,H-27)]1 alkene hydrogen signal: (H5.51, br.s), 4 terminal hydrogen signals [ alpha ], [ beta ] -n-butyl ] or [ beta ] -nH4.84(d, J ═ 7.8Hz, H-1 '), 5.96(d, J ═ 7.4Hz, H-1"),5.84(d, J ═ 7.1Hz, H-1'"), and 6.18(br.s, H-1 "")]An angeloyl hydrogen signal of group 2H 1.75(s,H3-5″″′),1.96(d,J＝6.4Hz,H3-4″″′),5.77(d,J＝6.4Hz,H-3″″′),2.00(s,H3-5″″″),2.08(d,J＝6.5Hz,H3-4″″″),5.96(d,J＝6.5Hz,H-3″″″)]。13C NMR spectrum (Table 2) showed that Compound SS-14 had 64 carbons, including 7 corner methyl carbons ((R))C29.7,28.1,21.2,20.4,17.8,16.9 and 15.9), 6 olefinic carbons ((s)C143.8,137.6,136.9,129.3,129.1 and 125.7), 4 terminal carbons (C: (C)C105.5,102.8,102.5 and 101.4).
The compound SS-14 was compared with the literature-reported NMR data of sanchakasaponin F, and found to be substantially identical, and thus was identified as sanchakasaponin F.
4. Structure identification of compound yucha saponin A (SS-15)
A white amorphous powder of a crystalline substance,
(c 0.31, MeOH). The reactions of Liebermann-Burchard and Molish are positive, and the color development of concentrated sulfuric acid-vanillin is red (TLC), which is presumed to be a triterpenoid saponin compound. ESI-MS M/z1339.5[ M + Na ]]+Suggesting that the molecular weight may be 1316, binding1H NMR and13the C NMR spectrum assumed that the compound SS-15 has the formula C64H100O28。
Of compound SS-151The H NMR spectrum showed a 7-angle methyl hydrogen signal [ alpha ]H 0.81(3H,s,H-25),1.03(3H,s,H-26),1.05(3H,s,H-24),1.12(3H,s,H-29),1.16(3H,s,H-23),1.32(3H,s,H-30),1.84(3H,s,H-27)]1 alkene hydrogen signal: (H5.54, br.s), 4 terminal hydrogen signals [ alpha ], [ beta ], [ alpha ] or [ beta ], [ beta ] orH4.88(d, J ═ 7.6Hz, H-1 '), 5.90(d, J ═ 7.3Hz, H-1"),5.84(d, J ═ 7.1Hz, H-1'"), and 6.23(br.s, H-1 "")]Croton acyl hydrogen signal of group 2H 1.44(d,J＝6.9Hz,H-4″″′),1.75(s,H-5″″′),6.83(d,J＝6.9Hz,H-3″″′),1.64(d,J＝6.8Hz,H-4″″″),1.83(s,H-5″″″),6.94(d,J＝6.8Hz,H-3″″″)]。13C NMR spectrum (Table 2) showed that Compound SS-15 had 64 carbons, including 7 corner methyl carbons ((R))C30.0,28.4,21.8,20.6,18.1,17.3 and 16.3), 6 olefinic carbons (CC143.8,137.6,136.9,129.3,129.1 and 125.7), 4 terminal carbons (C: (C)C105.7,102.9,102.6 and 101.4).
The compound SS-15 was compared with the NMR data reported in the literature for yucca saponins A, and found to be substantially identical, and was thus identified as yucca saponins A.
Table 2 13C NMR data of SS-14and SS-15
Spectra were measured in C5D5N at 100MHz.
Example 4
Monomeric compounds in vitro antifungal Activity test
The experiment takes candida albicans sensitive strains and candida albicans drug-resistant strains as indicator bacteria, adopts a paper sheet method in-vitro drug sensitivity experiment to determine an active monomer compound, and then uses a direct visual turbidimetry method to determine the MIC value and the MFC value of the active monomer compound.
1. Instrument and experimental material
1.1 Main instruments and devices
AIRTECH clean bench (suzhou su cleaning equipment limited); BS200 electronic analytical balance (sydoris, germany); LDZX-40SC type vertical automatic control electric pressure steam sterilizing pot (Shanghai Shenan medical instrument factory); electromagnetic ovens (nojishi electric appliances ltd, zhongshan city); 96-well cell culture plates (CONING COSTAR, USA); precision pipette gun (Gilson corporation, france); BDS200 inverted biomicroscope (Chongqing ott optical instruments, llc).
1.2 Main test materials
Culture medium: kaolin trade of Jiangmen City, Inc
Amphotericin B drug sensitive tablets (10 μ g): guangzhou Ruita Biotechnology Ltd
DMSO, DMSO: guangdong Guanghua chemical works Ltd
Methanol: shandong Yuwang Shi Kogyo Co Ltd
1.3 test strains
Candida albicans sensitive strain: purchased from Beijing Beinan institute of Biotechnology (BNCC337321) and stored in the important laboratory of medicinal material bioengineering in Fujian provincial region of Xiamen medical school.
2. Experimental methods
2.1 activation of the Strain: candida albicans stored in a refrigerator at-80 ℃ is placed on a culture medium plate and cultured in a thermostat at 34 ℃ for 48 hours to activate the Candida albicans.
2.2 paper sheet method in vitro drug sensitivity test
2.2.1 preparation of sample solution: approximately 2mg of each compound was weighed precisely. Dissolved in an appropriate amount of methanol to give a concentration of 20 mg/mL.
2.2.2 pipette 20. mu.L, 10. mu.L and 5. mu.L of the above solutions to be assayed (diameter: 5mm) respectively, and after the solvent had evaporated, the filter paper was placed on a prepared Sabouraud's solid medium (containing about 2X 10. sup. bacteria) containing Candida albicans6μ L), each mass was done in triplicate. And (3) taking methanol as a blank control, culturing at a constant temperature of 34 ℃ for 24h, taking out and measuring the diameter of the inhibition zone, and recording data.
2.2.3 determination of MIC and MFC by visual turbidimetry
A. Preparing bacterial liquid: diluting the activated Candida albicans to about 1 × 10 with sterile 1640 culture solution6mu.L/L.
B. Preparation of sample and control solutions: about 2mg of each compound was dissolved in a small amount of DMSO (about 4 ‰), and then PBS was added to prepare sample solutions of 400. mu.M, 200. mu.M, 100. mu.M, 50. mu.M, 25. mu.M, 12.5. mu.M, 6.25. mu.M, and 3.125. mu.M. The control solutions were prepared as described above.
C. Respectively sucking 100 mu L of sample solution with each concentration of the compound, placing the sample solution into a 96-well plate (three duplicate wells with each concentration), adding 100 mu L of bacterial liquid into each sample well, uniformly mixing, and respectively taking 200 mu L of bacterial liquid, 200 mu L of PBS and 200 mu L of bacterial liquid containing 2 thousandth of DMSO from the other three control wells. The control was performed in the same manner.
Determination of MIC and MFC values: and (3) placing the planted plate in an incubator at 34 ℃ for 24h, determining the MIC value by visual turbidimetry, taking the MIC concentration as a boundary, sucking 100 mu L of plate fluid with the MIC concentration and above, placing the plate fluid in a Sabouraud solid culture medium, uniformly coating, and culturing at 34 ℃ for 24h, wherein the concentration of non-growing bacteria is taken as the MFC value.
3. Results of the experiment
3.1 paper sheet method in vitro drug sensitivity test results
The paper method is used for testing the in-vitro anti-candida albicans activity of 4 compounds, and the results show that the compounds SS-9, SS-10, SS-14 and SS-15 have certain inhibition effects on two bacteria beads, wherein the compound SS-14 has the best activity, and the diameter of an inhibition zone on a bacterial strain reaches 10mm at 100 mu g.
Table 3 paper sheet method in vitro drug sensitivity experiment result*(n＝3)
10 mug of amphotericin B, and the diameter of the bacteriostatic circle is 20 mm.
5.5.2 MIC and MFC results for Compounds
The experimental result (Table 4) shows that the compounds SS-14 and SS-15 both have better antifungal activity, the MIC of the anti-Candida albicans is 12.5 mu M (0.016mg/mL), the MFC is 100 mu M (0.132mg/mL), the MIC value of the positive control amphotericin B to the Candida albicans is 0.78 mu M, and the MFC is 6.25 mu M.
MIC and MFC values for Table 4 Compounds
Claims (5)
1. The application of the schima superba extract in preparing medicines or cosmetics with antifungal effect is characterized in that the schima superba extract is obtained by a method comprising the following steps:
4.5kg of dry coarse powder of the schima superba stems, heating and refluxing for 3 times by using 95% ethanol with the amount 8 times of the medicinal materials, mixing the extracting solutions for 3 times, and concentrating under reduced pressure to obtain 200g of total extract;
dissolving and dispersing the total extract with 50% methanol water, and sequentially extracting with petroleum ether, chloroform, ethyl acetate and n-butanol to obtain 50g of petroleum ether layer, 35g of chloroform layer, 22g of ethyl acetate layer, 20g of n-butanol layer and 45g of water layer; subjecting the ethyl acetate part to silica gel column chromatography with chloroform-methanol system at ratio of 100: 0; 90: 10; 80: 20; 70: 30; 60: 40; 50: 50; 30: 70; 0:100 to obtain Fr.1-20 fractions; wherein, the fraction Fr.123.3 g is processed by ODS reverse phase column chromatography, 180g, 3.5cm x40cm, and 80:20 of water-methanol system; 70: 30; 60: 40; 40: 60; 20: 80; 0:100 to obtain fraction Fr.12-1-13;
collecting fraction Fr.12-9 containing compound SS-1413 mg and compound SS-156 mg;
the compound SS-14 is:
the compound SS-15 is
2. The use of claim 1, wherein said medicament comprises a toiletry.
3. The use according to claim 2, wherein the article comprises an oral, vaginitis or urinary tract infection article.
4. Use as claimed in any one of claims 1 to 3, wherein the Schima superba is the root and/or stem of Schima superba.
5. An antifungal drug or cosmetic, characterized by: the pharmaceutical or cosmetic contains the schima superba extract of claim 1.
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