CN102232942B - Antrodia camphorata cyclohexenone compound for suppressing growth of lymphoma tumor cells - Google Patents
Antrodia camphorata cyclohexenone compound for suppressing growth of lymphoma tumor cells Download PDFInfo
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- CN102232942B CN102232942B CN 201010174717 CN201010174717A CN102232942B CN 102232942 B CN102232942 B CN 102232942B CN 201010174717 CN201010174717 CN 201010174717 CN 201010174717 A CN201010174717 A CN 201010174717A CN 102232942 B CN102232942 B CN 102232942B
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Abstract
The invention relates to a new use of a compound. In the invention, (4-hydroxy-2,3-dimethoxy-6-methy-5(3,7,11-trimethyl-dodeca-2,6,10-trienyl)-cyclohex-2-enone is obtained from extract of Antrodia camphorata by separation and purification, and the cyclohexenone compound can be used for suppressing the growth of lymphoma tumor cells and can also be used in medical composition for suppressing the growth of the lymphoma tumor cells.
Description
Technical field
The invention relates to a kind of new application of chemical compound, especially about a kind of purposes that is suppressed the lymphatic cancer growth of tumour cell by the chemical compound of institute's separation and purification in Antrodia Camphorata (Antrodia cinnamomea) extract of utilizing.
Background technology
After the lymphocyte that is characterized as normal configuration of lymphatic cancer (Lymphoma) is damaged, replace jejune lymph corpuscle.Lymphatic cancer is to be apt to occur in the malignant tumor (malignant tumor) that the body endolymphatic system comprises lymphocyte, lymphatic vessel and lymph gland; On the other hand, be responsible for the lymphocyte of lymphocytic manufacturing, storage and the differentiation division of labor and regulate the pathological changes that organ comprises bone marrow, spleen and thymus, also can bring out lymphatic cancer.Clinically often according to the difference of cancer pathology organizational patterns with lymphatic cancer why divide outstanding Jin Shi lymphatic cancer (Hodgkin ' sdisease) and two kinds of non-Hodgkin's lymphatic cancers (Non-Hodgkin ' s lymphoma), wherein common with the non-Hodgkin's lymphatic cancer again.
The possible cause that lymphatic cancer occurs comprises the use of immune disappearance, viral infection, lonizing radiation or medicine and heredity etc.Research points out that lymphatic cancer is very average in the sickness rate of each age level, and men and women's number of the infected ratio is equal approximately, lymphatic cancer is the most normal with lymphadenopathy early symptom greatly, especially be apt to occur in the lymph node at the positions such as cervical region, oxter or groin, and often be the lymph node enlargement of Silent Neuritis bunchiness, the general symptom can appear in some patient, such as fever, Sleep hyperhidrosis, lose weight, long-term taediumvitae or powerlessness, skin are itched the signs such as dermexanthesis; In addition, the onset focus of 1/3rd lymphatic cancers of having an appointment is at lymph gland, and betides internal organs, and such as vertical diaphragm chamber of stomach, intestine and small intestine, lung etc., its symptom comprises stomachache, gastrorrhagia, intestinal obstruction or pulmonary's dyspnea etc.
The treatment of lymphatic cancer is different according to its cancer pathology kenel and clinical stages; the treatment major way comprises radiation cure, chemotherapy and bone marrow transplantation or peripheral blood stem cell transplantation etc.; generally speaking; lower and the patient that belongs to initial stage regional nodes's cancer of grade of malignancy; be fit to carry out radiation cure; and grade of malignancy is high and belong to the patient of middle and advanced stage; due to illness feelings worsen very fast; and scatter easily whole body; so take chemotherapy as main; no matter yet be radiation cure or chemotherapy, often can cause many side effect or malaise symptoms.Therefore, if can find the effectively natural therapeutant that has no side effect, must more promote lymphatic cancer treatment effect and other malaise symptoms of avoiding deriving.
Antrodia Camphorata (Antrodia cinnamomea), among the peoplely in Taiwan be called again wild rice, Antrodia camphorata or red Camphor tree in Camphor tree mushroom, Camphor tree wild rice, the Camphor tree, be the exclusive medicinal mushrooms of this province, it belongs to the perennial mushroom fungus class of Aphyllophorales (Aphyllophorales), Polyporaceae (Polyporaceae).Because Antrodia camphorata only parasitizes on the dried hollow heartwood interior wall tissue of Taiwan distinctive child care class Cinnamomum kanahirai hay ebon at occurring in nature, add artificial felling trees unlawfully, more shape is rare so that parasitize the wild Antrodia Camphorata quantity that wherein can grow, and because the growth phase of Antrodia camphorata sporophore is worked as slowly under naturalness, so wild Antrodia camphorata quantity is rare and expensive.
The sporophore of Antrodia Camphorata is perennial, and stockless is suberin to wooden, and the Lignum cinnamomi camphorae fragrance that its tool is strong, and changeableization of form have tabular, mitriform, horse-hof shape or tower-like.Nascent is platypelloid type and is cerise that its periphery can present radiation warp shape afterwards, and to expansion growth all around, color also changes light red brown or khaki into, and many pores are arranged, and it is the abundantest position of medical value of Antrodia Camphorata.
In the Taiwan folk custom medically, Antrodia Camphorata has that the circulation of qi promoting of dispeling the wind, blood stasis dispelling are invigorated blood circulation, the effect of warming middle-JIAO removing food stagnancy, removing toxic substances and promoting subsidence of swelling and sedation-analgesia, and be considered as first-class antidote, all alimentary toxicosis, diarrhoea, vomiting, pesticide intoxication all has Detoxication, all has adjuvant treatment efficacy to improving liver, stomach malfunction and blood circulation disease in addition.Antrodia Camphorata as the gill fungus mushrooms of edible medicinal, composition with many complexity, in the known physiologically active ingredient, comprise: triterpenoid compound (triterpenoids), polysaccharide body (polysaccharides, such as callose), adenosine (adenosine), vitamin is (such as vitamin B, niacin), protein (containing immunoglobulin), sudismase (superoxide dismutase, SOD), trace element (as: calcium, phosphorus, germanium), nucleic acid, steroid and blood pressure stabilization material (such as antodia acid) etc., these a little physiologically active ingredients are considered to have antitumor, increase immunocompetence, antiallergic, Anti-bacterium, resisting hypertension, the multiple efficacies such as blood sugar lowering and cholesterol reducing, and help the treatment of hepatoprotective and liver related disease.
The composition Study of relevant Antrodia camphorata, mostly focus on macromolecular polysaccharide body (polysaccharides) and micromolecular triterpenes (triterpenoids) and steroid (steroids), wherein, Antrodia camphorata contains macromolecular polysaccharide body, form with different monosaccharide and to be present in its sporophore and the mycelium, but after spectrum analysis, all contain the callose (β-D-glucans) of tool physiologically active; Triterpenoid compound is the general name that is combined into hexagon or pentagon native compound by 30 carbons, and the bitterness of Antrodia Camphorata institute tool is namely mainly from this composition of triterpenes, and it also is studied maximum composition.The triterpenoid compound that obtains from sporophore has antrocin, 4,7-dimethoxy-5-methyl isophthalic acid, 3-benzo dioxy ring (4,7-dimethoxy-5-methy-1,3-benzodioxole) and 2,2 ', 5,5 '-tetramethoxy-3,4,3 ', 4 '-two-methylene-dioxy-6,6 '-dimethyl diphenyl (2,2 ', 5,5 '-teramethoxy-3,4,3 ', 4 '-bi-methylenedioxy-6,6 '-dimethyl biphenyl) (Chiang et al., 1995), the new triterpenoid compound antcinA take lumistane (ergostane) as skeleton, antcin B, antcin C antcin E, antcin F, methyl antcinate G and methyl antcinateH (Cherng et al., 1995,1996).The chemical compound that sporophore contains in addition take lumistane as skeleton comprises Zhankuic acid A, B and C zhankuic acid D and zhankuic acid E (Chen and Yang, 1995; Yang 1996), noval chemical compound 15 α take lanostane (lanostane) as skeleton-acetyl-dehydrosulphurenic acid (15 α-acetyl-dehydrosulphurenic acid), dehydroeburicoic acid (dehydroeburicoic acid) and the sulfurenic acid (dehydrasulphurenic acid) that anhydrates.
Although can learn that by at present many experiments the Antrodia Camphorata extract has aforementioned effect, and its ingredient is also analyzed successively to be gone out, but which kind of effective ingredient in the extract can be facilitated the inhibition cancer effect of Antrodia Camphorata actually, do not deliver concrete relevant effective ingredient, remaining further experiment research differentiates, if so can find out the composition of contained real establishment tumor growth in this extract, to be conducive to Antrodia Camphorata and press down the research that cancer is shut down mutually and turned, and Antrodia Camphorata is applied to cancer, and for example treatment and the prevention of lymphatic cancer there are greatest help.
Summary of the invention
For be that what composition has the effect that presses down cancer in the clear Antrodia Camphorata extract actually, the present invention provides the chemical compound of following structural (1) by separation and purification in the Antrodia Camphorata extract;
Wherein, X is oxygen (O) or sulfur (S), and Y is oxygen or sulfur; R1 is hydrogen base (H), methyl (CH
3) or (CH
2) m-CH
3, R
2Hydrogen base, methyl or (CH
2) m-CH
3, R
3Hydrogen base, methyl or (CH
2) m-CH
3, m=1～12; N=1～12.
In the chemical compound suc as formula (1) structural formula, the preferably is the chemical compound of formula as follows (2):
The chemical compound of formula (2), its chemistry 4-hydroxyl-2 by name, 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene (4-hydroxy-2,3-dimethoxy-6-methy-5 (3,7,11-trimethyl-dodeca-2,6,10-trienyl)-cyclohex-2-enone), molecular formula is C
24H
38O
4, outward appearance is the pale yellow powder shape, molecular weight is 390.
The chemical compound of Chinese style of the present invention (1), formula (2) is that separation and purification is from Antrodia Camphorata water extract or organic solvent extraction thing, organic solvent can comprise alcohols (for example methanol, ethanol or propanol), esters (for example ethyl acetate), alkanes (for example hexane) or alkyl halide (for example chloromethanes, ethyl chloride), but not as limit, wherein the preferably is alcohols, and better person is ethanol.
By aforesaid compound, the present invention is applied in the inhibition tumor cell growth, enables further to use during the medicine that is included in the treatment cancer forms part the therapeutic effect of gain cancer.The scope that the present invention must use this chemical compound comprises the growth inhibited for the lymphatic cancer tumor cell, by suppressing the ramp of these tumor cells, and then suppresses the hypertrophy of tumor, and delays the deterioration of tumor.Wherein, better chemical compound is the 4-hydroxyl-2 of formula (2), 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene.
On the other hand, also the chemical compound of formula (1) or/and formula (2) can be used among the present invention in the composition of the medical composition that suppresses the lymphatic cancer growth of tumour cell.Aforementioned medical composition still can comprise pharmaceutically acceptable carrier except the chemical compound of the formula that comprises effective dose (1) or/and formula (2).Carrier can be excipient (such as water), filler (such as sucrose or starch), adhesive (such as cellulose derivative), diluent, disintegrating agent, absorption enhancer or sweeting agent, but does not only limit to this.Medical composition of the present invention can be manufactured according to the preparation method of general known pharmacy, with formula (1) or/mix mutually with more than one carrier with formula (2) effective ingredient dosage, prepare required dosage form, this dosage form can comprise lozenge, powder, granule, capsule or other liquid preparation, but not as limit.
Below will further specify embodiments of the present invention; following cited embodiment illustrates the present invention; be not to limit scope of the present invention; anyly have the knack of this skill person; without departing from the spirit and scope of the present invention; when can doing a little change and retouching, so protection scope of the present invention is as the criterion when looking accompanying the claim person of defining.
The specific embodiment
Through extraction Antrodia Camphorata water extract or organic solvent extraction thing later, can be further by in addition separation and purification of high performance liquid chroma-tography, again each separatory (fraction) is carried out the test of cancer resistant effect afterwards.At last, then the separatory for the tool cancer resistant effect carries out component analysis, and the composition that may produce cancer resistant effect is further done respectively the inhibition test of lymphatic cancer tumor cell.Find namely that finally the chemical compound suc as formula (1)/formula (2) has the effect that suppresses the lymphatic cancer growth of tumour cell among the present invention.
For convenience of description the present invention below will be with the 4-hydroxyl-2 of formula (2), and 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-pimelie kelone compounds describes.In addition, for confirming 4-hydroxyl-2,3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-the 2-pimelie kelone compounds is to the inhibition of growth of tumour cell, is with the MTT analytic process among the present invention, according to National Cancer Institute (National Cancer Institute, NCI) antitumor drug screening pattern is carried out the test of cell survival rate to the lymphatic cancer tumor cell.Confirmed by those tests, 4-hydroxyl-2,3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-, 12 carbon triolefins)-the 2-cyclonene is for the lymphatic cancer tumor cell: U937 cell line can reduce its survival rate, relatively under and can to reduce simultaneously growth half suppression ratio desired concn (be IC
50Value), therefore must be by 4-hydroxyl-2,3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene is applied on the growth inhibited of lymphatic cancer tumor cell, and further can be used in the treatment of lymphatic cancer.Hereby aforementioned embodiments is elaborated as follows:
Embodiment 1:
4-hydroxyl-2, the separation of 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene
With Antrodia Camphorata mycelium, sporophore or the mixture of the two about 100 grams, insert in the triangular pyramidal bottle, the water and the alcohols (70%～100% alcohol solution) that add proper proportion, wherein, described alcohols is preferably ethanol, extract more than at least 1 hour in 20～25 ℃ of lower stirrings, afterwards with filter paper and 0.45 μ m membrane filtration, collect filtrate and namely get the Antrodia Camphorata extract.
Antrodia Camphorata extract with aforementioned collection, utilize high-effect liquid chromatography (LC) instrument (High PerformanceLiquid chromatography), chromatography pipe (column) with RP18 is analyzed, and with methanol (A) and 0.1%～0.5% aqueous acetic acid (B) (its solution proportion is: 0～10 minute, the B ratio was 95%～20% as mobile phase (mobile phase); 10～20 minutes, the B ratio was 20%～10%; 20～35 minutes, the B ratio was 10%～90%; 35～40 minutes, the B ratio was 10%～95%), carry in the speed undershoot of per minute 1ml, simultaneously with the long detector analysis of ultraviolet-visible light all-wave.
25 minutes to 30 minutes the extract that rushes is collected the concentrated solid product of pale yellow powder shape of getting final product to get, and this is 4-hydroxyl-2,3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene.By analysis, its molecular formula is C
24H
38O
4, molecular weight 390, fusing point (m.p.) are 48 ℃～52 ℃.Nuclear magnetic resonance, NMR (NMR) assay value is then as follows:
1H-NMR (CDCl
3) δ (ppm): 1.51,1.67,1.71,1.75,1.94,2.03,2.07,2.22,2.25,3.68,4.05,5.07 and 5.14.
13C-NMR (CDCl
3) δ (ppm): 12.31,16.1,16.12,17.67,25.67,26.44,26.74,27.00,39.71,39.81,4.027,43.34,59.22,60.59,120.97,123.84,124.30,131.32,135.35,135.92,138.05,160.45 and 197.12.
Embodiment 2:
The active testing of In Vitro Anti lymphatic cancer tumor cell
By in the further test implementation example 1 the discovery chemical compound to the inhibition of tumor cell, present embodiment will be according to National Cancer Institute (National Cancer Institute, NCI) antitumor drug screening pattern, at first get the 4-hydroxyl-2 that separates among the embodiment 1,3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-the 2-pimelie kelone compounds, add and contain in the culture fluid of human lymphatic cancer tumor cell U937, carry out the test of tumor cell viability.Wherein, the test of cell survival can be adopted known MTT analytic process and be analyzed, and lymphatic cancer tumor cell U937 is human lymphocytic cancer cell strain (human histiocytic lymphoma cell line).
The MTT analytic process is a kind of common analytical method for analysis of cells hypertrophy (cell proliferation), survival rate (percent of viable cells) and cytotoxicity (cytotoxicity).Wherein, MTT (3-[4,5-dimethylthiazol-2-yl] 2,5-diphenyltetrazolium bromide) is a yellow stain, it can be absorbed by living cells and is reduced into water insoluble by the succinic acid tetrazolium reductase (succinate tetrazoliumreductase) in the Mitochondria and be hepatic formazan, therefore whether form by formazan, can judge and calculate the survival rate of cell.
At first human lymphocytic cancer cell U937 is cultivated in the RPMI1640 culture medium that contains 10% hyclone (fetal bovine serum), this culture medium still comprises the dish Ni Xilin (Penicillin) of 10U/ml, and the streptomycin (Streptomycin) of 100 μ g/ml, and in 5%CO
2, cultivated 24 hours in 37 ℃ of environment.Cell after the hypertrophy is cleaned once with PBS, and process cell with 1 times trypsin-EDTA, under 1,200rpm centrifugal 5 minutes subsequently, with cell precipitation and abandon supernatant.Add afterwards the new culture fluid of 10ml, slight wobble suspends cell again, in the 96 holes trace dish that again cell is placed in.During test, organize in contrast (without total extract of purifies and separates) respectively at the Antrodia Camphorata extract that adds 30,10,3,1,0.3,0.1 and 0.03 μ g/ml in each hole; And the 4-hydroxyl-2 that in each hole, adds 30,10,3,1,0.3,0.1 and 0.03 μ g/ml, 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene is as test group, in 37 ℃, 5%CO
2Lower cultivation 48 hours.Thereafter, the MTT in add 2.5mg/ml under the environment of lucifuge in each hole reacts the lysis buffer cessation reaction that adds again 100 μ l after 4 hours in each hole.Under 570nm extinction wavelength, measure its light absorption value with Enzyme Immunoassay Analyzer at last, use the survival rate of calculating cell, and to extrapolate its half suppression ratio desired concn of growing (be IC
50Value), its result as shown in Table 1.
Table one: external test result to lymphatic cancer tumor cell survival rate
By in the table one as can be known, by 4-hydroxyl-2, the effect of 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene, it is for the IC of the human lymphatic cancer tumor cell of U937
50Value is 9.71 μ g/ml, compared to the measured IC of matched group Antrodia Camphorata extraction mixture
50Value (not showing in the table) is low many, so the 4-hydroxyl-2 in the susceptible of proof Antrodia Camphorata extract, 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-the 2-cyclonene can be used in the inhibition of lymphatic cancer growth of tumour cell really.
In sum, the 4-hydroxyl-2 of separated from Antrodia camphorate of the present invention, 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-pimelie kelone compounds, but the growth of establishment lymphatic cancer tumor cell.On the other hand, be the material of natural extraction because of antrodia camphorata cyclohexenone compound, when so it is applied to suppress lymphatic cancer, can't cause that the patient is uncomfortable or produce other side effect such as toxicity, complication, and its also can with chemotherapeutic agents and usefulness, to reduce the chemotherapeutics using dosage and to reduce the side effect that those chemotherapeutic agents are caused; In addition, also it can be prepared into the medical composition for the treatment of lymphatic cancer, wherein, this medical composition still can comprise pharmaceutically acceptable carrier except the antrodia camphorata cyclohexenone compound that comprises effective dose.Carrier can be excipient (such as water), filler (such as sucrose or starch), adhesive (such as cellulose derivative), diluent, disintegrating agent, absorption enhancer or sweeting agent, but does not only limit to this.Medical composition of the present invention can be manufactured according to the preparation method of general known pharmacy, the antrodia camphorata cyclohexenone compound of effective ingredient dosage is mixed mutually with more than one carrier, prepare required dosage form, this dosage form can comprise lozenge, powder, granule, capsule or other liquid preparation, but not as limit.Use the purpose that reaches treatment lymphatic cancer tumor disease.
Claims (2)
1. one kind with compound 4-hydroxy base-2, and 3-dimethoxy-6-methyl-5 (3,7,11-trimethyl-2,6,10-12 carbon triolefins)-2-cyclonene is used in the application that preparation suppresses the medicine of lymphatic cancer growth of tumour cell.
2. application according to claim 1, wherein, described lymphatic cancer tumor cell is U937 cell line.
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| CN101225066A (en) * | 2007-01-18 | 2008-07-23 | 国鼎生物科技股份有限公司 | Cyclohexenone extract of antrodia camphorata |
| CN101357883A (en) * | 2007-07-30 | 2009-02-04 | 国鼎生物科技股份有限公司 | Antrodia camphoratea pimelie kelone compound for treating autoimmune disease and medicine composition |
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| CN101225066A (en) * | 2007-01-18 | 2008-07-23 | 国鼎生物科技股份有限公司 | Cyclohexenone extract of antrodia camphorata |
| CN101357883A (en) * | 2007-07-30 | 2009-02-04 | 国鼎生物科技股份有限公司 | Antrodia camphoratea pimelie kelone compound for treating autoimmune disease and medicine composition |
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