CN105906500A - Filicinic acid compounds with lipase inhibition effect, and application thereof - Google Patents
Filicinic acid compounds with lipase inhibition effect, and application thereof Download PDFInfo
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- CN105906500A CN105906500A CN201610255786.0A CN201610255786A CN105906500A CN 105906500 A CN105906500 A CN 105906500A CN 201610255786 A CN201610255786 A CN 201610255786A CN 105906500 A CN105906500 A CN 105906500A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
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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
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- 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)
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Abstract
The invention provides filicinic acid compounds sarothralen A, Rxj-43 and Rxj-19 or medicinal salts thereof, a medicinal composition comprising the filicinic acid compounds as an effective component and at least one pharmaceutically acceptable carrier, a preparation method of the filicinic acid compounds, and an application of the compounds in the preparation of lipase inhibition medicines. The sarothralen A is a known structure, the Rxj-43 and the Rxj-19 are new compounds filicinic acids (phloroglucinol dimer derivatives), and the sarothralen A, the Rxj-43 and the Rxj-19 have good in-vitro lipase inhibition activity, and have many advantages as lipase inhibition medicines.
Description
Technical field:
The invention belongs to technical field of pharmaceuticals, specifically, relate to filicinic acid compounds sarothralen A, Rxj-43, the Rxj-19 and preparation method thereof with lipase inhibiting activity, the pharmaceutical composition with this compound as active component, and its application in treatment obesity.
Background technology:
Pancreas and gastric lipase are that in intestinal, fat digestion absorbs necessary.Fat in food is absorbed at intestinal after being hydrolyzed to monoacylglycerol and free fatty, recombines fat the most in vivo, causes athero, ultimately results in obesity.Application lipase inhibitor can effectively suppress the lipase decomposition catalytic action to fat in intestinal, reaches to reduce fat absorption, controls and treat the purpose of obesity.Therefore, the effective lipase inhibitor of development and application is paid close attention to by people.
Hypericum (Hypericum) is a big genus of Guttiferae (Guttiferae), about 400 kinds of the whole world, except the low extraterrestrial world in polar region, north and south two or desert ground and the major part torrid zone blazons.China there are about 55 kind of 8 subspecies, several all parts of the country of originating in, but is concentrated mainly on southwest.Except being used for viewing and admiring, hypericum has the multiple pharmacologically actives such as antidepressant, antiviral, antibacterial and antitumor.
Herba Hyperici Japonici (H.japonicum Thunb.): " Chinese medicine voluminous dictionary " records kind, calls Herba Hyperici Japonici, Stellaria alsine Grim..Annual herb, originates in the ground such as Jiangsu, Zhejiang, Sichuan, Yunnan.There is the effects such as clearing away heat-damp and promoting diuresis, subduing swelling and detoxicating, for jaundice pyretic stranguria, toxic swelling, venom.Document reports that the chemical composition of this plant has flavone, xanthone etc..Up to now, prior art does not has the bioactive report that lipase is suppressed by filicinic acid compounds sarothralen A, Rxj-43, Rxj-19.
Summary of the invention:
Present invention aim at providing filicinic acid compounds sarothralen A, Rxj-43, Rxj-19 of isolated from Herba Hyperici Japonici (H.japonicum), its preparation method, the particularly application in treatment obesity medicine in medicine.
In order to realize this brightest above-mentioned purpose, the invention provides following technical scheme:
Following compound R xj-43, Rxj-19 shown in structural formula or its pharmaceutical salts.
Filicinic acid compounds Rxj-43, Rxj-19 containing therapeutically effective amount any one or two kinds of mixture or its pharmaceutical salts and the pharmaceutical composition of pharmaceutically acceptable carrier.
Following compound Sarothralen A, Rxj-43, Rxj-19 shown in structural formula or the application in preparing lipase inhibitor of its pharmaceutical salts,
Compound SarothralenA, Rxj-43, Rxj-19 or the application in the medicine of preparation treatment obesity of its pharmaceutical salts.
Filicinic acid compounds Rxj-43 as mentioned, Rxj-19, Sarothralen A or its pharmaceutical salts, wherein said pharmaceutical salts is for referring to pharmaceutically acceptable salt, it is the salt formed with organic acid, described organic acid is tartaric acid, formic acid, acetic acid, ethanedioic acid, butanoic acid, maleic acid, succinic acid, adipic acid, alginic acid, citric acid, aspartic acid, benzenesulfonic acid, dextrocamphoric acid., camphorsulfonic acid, didextrose acid, Pentamethylene. propanoic acid, lauryl sulphate acid, ethyl sulfonic acid, glucoheptonic acid, phosphoglycerol, enanthic acid, caproic acid, Fumaric acid, 2 ethylenehydrinsulfonic acids, lactic acid, methanesulfonic acid, nicotinic acid, 2 LOMAR PWA EINECS 246-676-2, flutter acid, pectinic acid, 3 phenylpropionic acids, neopentanoic acid, propanoic acid, p-methyl benzenesulfonic acid and hendecanoic acid.
The method of filicinic acid compounds Rxj-43, Rxj-19 described in preparation, takes Herba Hyperici Japonici and is dried herb, pulverizes, with merceration 2 times under methanol room temperature, each 24 hours, united extraction liquid, decompression distillation and concentration, obtain extractum, extractum 100-200 mesh silica gel mixed sample, silica gel column chromatography, chloroform section is afforded with chloroform, sample mixed by the chloroform section polyamide of 1.5 times amount, crosses MCI post, with the MeOH-H of 7:3-10:02O carries out gradient elution, obtains 5 big sections A-E, and B section, through silica gel column chromatography, carries out gradient elution with the petroleum ether-acetone of 1:0-0:1, obtains 4 segment B1-B4, and wherein B3 section is through preparation HPLC, methanol-water, obtains sarothralen A after 95:5 is isolated and purified；Equally, B4 part is through preparation HPLC, methanol-water, obtains Rxj-19, C section 100-200 mesh silica gel mixed sample after 95:5 is isolated and purified, silica gel column chromatography, carrying out gradient elution with the petroleum ether-acetone of 1:0-0:1, obtain 5 parts C1-C5, wherein C2 part is through preparation HPLC, methanol-water, obtains Rxj-43 after 95:5 is isolated and purified.
The method preparing filicinic acid compounds sarothralen A, takes Herba Hyperici Japonici and is dried herb, pulverizes, with merceration 2 times under methanol room temperature, each 24 hours, united extraction liquid, decompression distillation and concentration, obtain extractum, extractum 100-200 mesh silica gel mixed sample, silica gel column chromatography, chloroform section is afforded with chloroform, sample mixed by the chloroform section polyamide of 1.5 times amount, crosses MCI post, with the MeOH-H of 7:3-10:02O carries out gradient elution, obtains 5 big sections A-E, and B section, through silica gel column chromatography, carries out gradient elution with the petroleum ether-acetone of 1:0-0:1, obtains 4 segment B1-B4, and wherein B3 section is through preparation HPLC, methanol-water, obtains sarothralen A after 95:5 is isolated and purified.
Sarothralen A is known structure, Rxj-43 and Rxj-19 is noval chemical compound filicinic acid class (dimerization phloroglucinol analog derivative), has preferable external lipase inhibiting activity, has more advantage as lipase inhibitors thing.SarothralenA, Rxj-43, Rxj-19 have stronger inhibitory action to lipase, can be used for preparing slimming medicine preparation as active component, have preferable medical value.
Accompanying drawing illustrates:
Figure 1Structural representation for the compounds of this invention sarothralen A, Rxj-43, Rxj-19Figure。
Detailed description of the invention:
Below in conjunction withAccompanying drawing, further illustrate the essentiality content of the present invention with embodiments of the invention, but do not limit the present invention with this.
Embodiment 1:
1, the preparation of compound sarothralen A, Rxj-43, Rxj-19 and structured data:
Herba Hyperici Japonici is dried herb (14kg), pulverizes, and with merceration 2 times under methanol room temperature, each 24 hours, united extraction liquid, reduced pressure distillation and concentration, obtains extractum 2.5kg.Crude extract 100-200 mesh silica gel mixed sample, silica gel column chromatography, afford chloroform section (164.2g) with chloroform.Sample mixed by the chloroform section polyamide of 1.5 times amount, crosses MCI post, with MeOH-H2O (7:3-10:0) carries out gradient elution, obtains 5 big sections (A-E).B section (25.5g), through silica gel column chromatography, carries out gradient elution with petroleum ether-acetone (1:0-0:1), obtains 4 segments (B1-B4).Wherein B3 section (3.0g) obtains sarothralen A (520mg) after preparation HPLC (methanol-water, 95:5) is isolated and purified；Equally, B4 part (6.4g) obtains Rxj-19 (230mg) after preparation HPLC (methanol-water, 95:5) is isolated and purified.C section (25.5g) 100-200 mesh silica gel mixed sample, silica gel column chromatography, gradient elution is carried out with petroleum ether-acetone (1:0-0:1), obtain 5 parts (C1-C5), wherein C2 part (3.2g) finally obtains Rxj-43 (850mg) after preparation HPLC (methanol-water, 95:5) is isolated and purified.
The structure elucidation of compound R xj-43, Rxj-19:
Compound R xj-43, colorless gum.It is m/z 581 [M-H] that ESI-MS spectrum provides quasi-molecular ion peak-, in conjunction with high-resolution anion HRESI-MS (m/z [M-H]-581.3117, calcd for 581.3114) and13C and DEPT H NMR spectroscopyFigureThe information provided, determines that its molecular formula is C34H46O8, calculating degree of unsaturation is 12.UV spectrum has absorption at 204 (4.45), 225 (4.32), 305 (4.27), 340 (4.11) places, illustrates to there is longer conjugated system in molecule.Analyze1H and13C H NMR spectroscopy, shows containing 34 carbon signals in compound 1 in conjunction with hsqc spectrum, including 9 methyl, 5 methylene, 4 methines (including 2 olefinic carbons), 16 quaternary carbons (wherein 1 saturated quaternary carbon).Carefully analyze these data and show that Rxj-43 is filicinic acid compounds, and much like with known compound sarothralen A.Finally, Rxj-43 is confirmed as the derivant of sarothralen A, and in sarothralen A, C-7 position isopropyl is replaced by the sec-butyl in 2.Compound R xj-19 is the 15' oxidation product of compound 2, and along with the formation of 16', 17' double bond, what C-7 position carbonyl carried is a sec-butyl.Compound1H and13C H NMR spectroscopy dataSuch as table 1Shown in 2.
Table 1. the NMR of compound R xj-43 and Rxj-1913C modal data (acetone)
Table 2. the NMR of compound R xj-43 and Rxj-191H modal data (acetone)
Embodiment 2
The lipase inhibiting activity of Sarothralen A, Rxj-43, Rxj-19:
Reagent source: porcine pancreatic lipase (PPL) is purchased from Aladdin Reagent Company；P-nitrophenyl butyrate (p-NPB), Orlistat are purchased from Sigma company；D-PBS is purchased from Hyclone company；Anhydrous calcium chloride is Chengdu Ke Long chemical reagent factory product.
Experimental technique: in 96 hole ELISA Plate, be sufficiently mixed with PPL solution by testing compound, each concentration all sets 3 repeating holes, 37 DEG C, 15min；Adding p-NPB, mix homogeneously, 37 DEG C, 15min, microplate reader measures OD value (400nm/630nm), and detection wavelength is 400nm, and reference wavelength is 630nm.Experiment arranges blank control wells and Orlistat Positive control wells simultaneously.
Computing formula:
PPL maximum inhibition (%)=(1 sample OD value/experiment contrast hole OD value) × 100%
IC50(50%concentration of inhibition) presses Reed&Muench method and calculates.Testing result is shown inTable 3Shown in.
Table 3, Sarothralen A, Rxj-43, Rxj-19 lipase suppression IC50Value
ByTable 3Visible: Sarothralen A, Rxj-43, Rxj-19 have stronger inhibitory action to lipase, can be used for preparing slimming medicine preparation as active component, there is preferable medical value.
Embodiment 3:
Prepare compound Sarothralen A, Rxj-43, Rxj-19 by embodiment 1, in compound Sarothralen A, Rxj-43, Rxj-19 any one or appoint several mixing and the excipient weight ratio than 1:1 or 1:2 to add excipient, pelletizing press sheet.
Embodiment 4:
Compound Sarothralen A, Rxj-43, Rxj-19 is prepared by embodiment 1, capsule preparations method makes capsule routinely.
Embodiment 5:
First prepare compound Sarothralen A, Rxj-43, Rxj-19 by embodiment 1, then make tablet as follows.
Tablet: compound Sarothralen A, Rxj-43, Rxj-19 any one or appoint several mixing 100mg, starch is appropriate, Semen Maydis pulp in right amount, Magnesium Stearate proper quantity.Preparation method: mixed with auxiliary agent by compound, sieves, and uniformly mixes in suitable container, the granulating mixture tabletting obtained.
Embodiment 6:
Capsule: compound Sarothralen A, Rxj-43, Rxj-19 any one or appoint several mixing 100mg, starch in right amount, Magnesium Stearate proper quantity.
Preparation method: by compound 1-4 any one or appoint several mixing mix with auxiliary agent, sieve, uniformly mix in suitable container, the mixture loading obtained firmlyGelatinCapsule.
Embodiment 7:
Tablet: embodiment 1 gained compound Sarothralen A, Rxj-43, Rxj-19 any one or appoint several mixing 10mg, lactose 180mg, starch 55mg, magnesium stearate 5mg；
Preparation method: by compound Sarothralen A, Rxj-43, Rxj-19 any one or appoint several mixing, breast sugar and starch mixing, uniformly moisten with water, mixture after moistening is sieved and is dried, after sieve, add magnesium stearate, then by mixture tabletting, every tablet weight 250mg, compounds content is 10mg.
Embodiment 8:
Ampulla: embodiment 1 gained compound Sarothralen A, Rxj-43, Rxj-19 any one or appoint several mixing 2mg, sodium chloride 10mg；
Preparation method: by compound Sarothralen A, Rxj-43, Rxj-19 any one or appoint several mixing and sodium chloride to be dissolved in appropriate water for injection, filter gained solution, aseptically load in ampoule bottle.
Embodiment 9:
Capsule: embodiment 1 gained compound Sarothralen A, Rxj-43, Rxj-19 any one or appoint several mixing 10mg, lactose 187mg, magnesium stearate 3mg；
Preparation method: by compound Sarothralen A, Rxj-43, Rxj-19 any one or appoint several mixing mix with auxiliary agent, sieve, uniformly mix, the mixture loading obtained firmlyGelatinCapsule, each capsule weight 200mg, active component content is 10mg.
Claims (7)
1. following compound R xj-43, Rxj-19 shown in structural formula or its pharmaceutical salts.
2. contain the filicinic acid compounds shown in the claim 1 of therapeutically effective amount any one or two kinds of mixture or
Its pharmaceutical salts and the pharmaceutical composition of pharmaceutically acceptable carrier.
3. following compound Sarothralen A, Rxj-43, Rxj-19 shown in structural formula or its pharmaceutical salts are preparing lipase
Application in inhibitor,
4. compound Sarothralen A, Rxj-43, Rxj-19 or its pharmaceutical salts answering in the medicine of preparation treatment obesity
With.
Filicinic acid compounds Rxj-43, Rxj-19, Sarothralen the most as claimed in claim 1 or 2 or 3 or 4
A or its pharmaceutical salts, it is characterised in that described pharmaceutical salts, for referring to pharmaceutically acceptable salt, is the salt formed with organic acid,
Described organic acid be tartaric acid, formic acid, acetic acid, ethanedioic acid, butanoic acid, maleic acid, succinic acid, adipic acid, alginic acid,
The acid of citric acid, aspartic acid, benzenesulfonic acid, dextrocamphoric acid., camphorsulfonic acid, didextrose, Pentamethylene. propanoic acid, lauryl sulphate acid,
Ethyl sulfonic acid, glucoheptonic acid, phosphoglycerol, enanthic acid, caproic acid, Fumaric acid, 2 ethylenehydrinsulfonic acids, lactic acid, methanesulfonic acid,
Nicotinic acid, 2 LOMAR PWA EINECS 246-676-2, flutter acid, pectinic acid, 3 phenylpropionic acids, neopentanoic acid, propanoic acid, p-methyl benzenesulfonic acid and hendecanoic acid.
6. the method for preparation filicinic acid compounds Rxj-43, Rxj-19 described in claim 1, takes Herba Hyperici Japonici and is dried
Herb, pulverizes, and with merceration 2 times under methanol room temperature, each 24 hours, united extraction liquid, reduced pressure distillation and concentration, obtains leaching
Cream, extractum 100-200 mesh silica gel mixed sample, silica gel column chromatography, afford chloroform section with chloroform, chloroform section is with 1.5 times
Sample mixed by the polyamide of amount, crosses MCI post, with the MeOH-H of 7:3-10:02O carries out gradient elution, obtains 5 big sections
A-E, B section, through silica gel column chromatography, carries out gradient elution with the petroleum ether-acetone of 1:0-0:1, obtains 4 segment B1-B4,
Wherein B3 section is through preparation HPLC, methanol-water, obtains sarothralen A after 95:5 is isolated and purified；Equally, B4 part
Through preparation HPLC, methanol-water, after 95:5 is isolated and purified, obtain Rxj-19, C section 100-200 mesh silica gel mixed sample, silica gel
Column chromatography, carries out gradient elution with the petroleum ether-acetone of 1:0-0:1, obtains 5 parts C1-C5, wherein C2 part warp
Preparation HPLC, methanol-water, obtain Rxj-43 after 95:5 is isolated and purified.
7. the side of filicinic acid compounds sarothralen A involved in application described in preparation claim 3 or 4
Method, takes Herba Hyperici Japonici and is dried herb, pulverizes, with merceration 2 times under methanol room temperature, and each 24 hours, united extraction liquid, subtract
Pressure distillation and concentration, obtains extractum, extractum 100-200 mesh silica gel mixed sample, and silica gel column chromatography affords chloroform section with chloroform,
Sample mixed by the chloroform section polyamide of 1.5 times amount, crosses MCI post, with the MeOH-H of 7:3-10:02O carries out gradient elution,
Obtaining 5 big sections A-E, B section, through silica gel column chromatography, carries out gradient elution with the petroleum ether-acetone of 1:0-0:1, obtains 4
Individual segment B1-B4, wherein B3 section is through preparation HPLC, methanol-water, obtains sarothralen A after 95:5 is isolated and purified.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106397169A (en) * | 2016-04-22 | 2017-02-15 | 中国科学院昆明植物研究所 | Filicinic acid compounds, and pharmaceutical compositions and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020039768A1 (en) * | 2000-04-07 | 2002-04-04 | Cordula Hopmann | Percyquinnin, a process for its production and its use as a pharmaceutical |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20020039768A1 (en) * | 2000-04-07 | 2002-04-04 | Cordula Hopmann | Percyquinnin, a process for its production and its use as a pharmaceutical |
Non-Patent Citations (5)
| Title |
|---|
| ISHIGURO, KYOKO等: "Sarothralen A and B, new antibiotic compounds from Hypericum japonicum", 《PLANTA MEDICA》 * |
| KYOKO ISHIGURO等: "Saroaspidin A, B, and C: Additional Antibiotic Compounds from Hypericum japonicum", 《PLANTA MEDICA》 * |
| YAMAKI, MASAE等: "Antimicrobial activity of naturally occurring and synthetic", 《PHYTOTHERAPY RESEARCH》 * |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106397169A (en) * | 2016-04-22 | 2017-02-15 | 中国科学院昆明植物研究所 | Filicinic acid compounds, and pharmaceutical compositions and application thereof |
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