CN103641839B - There is in green onion lotus the compound of antitumor action and method for separating and preparing thereof and application - Google Patents

There is in green onion lotus the compound of antitumor action and method for separating and preparing thereof and application Download PDF

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Publication number
CN103641839B
CN103641839B CN201310560305.3A CN201310560305A CN103641839B CN 103641839 B CN103641839 B CN 103641839B CN 201310560305 A CN201310560305 A CN 201310560305A CN 103641839 B CN103641839 B CN 103641839B
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candidine
compound
green onion
onion lotus
chloroform
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CN103641839A (en
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张勇慧
姚广民
王富乾
张锦文
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Huazhong University of Science and Technology
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Huazhong University of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/20—Spiro-condensed systems

Abstract

The invention discloses separation obtains from green onion lotus the compound with antitumor action and method for separating and preparing thereof and application, specifically disclose activity and the structure of the alkaloid compound deriving from plant green onion lotus, comprise preparation method for separating and purifying and the related activity of anti-tumor activity good compound N-styroyl crinidine alkali and Candidine A and green onion lotus B.Research confirms that it has inhibit activities to leukemia HL-60, K562, lung cancer A-549, liver cancer HepG2 and colorectal carcinoma HT-29 tumor cell proliferation, can as the medicine of the tumor diseases such as treatment leukemia, lung cancer, liver cancer, colorectal carcinoma.

Description

There is in green onion lotus the compound of antitumor action and method for separating and preparing thereof and application
Technical field
The invention belongs to medical art, relate to antineoplastic compound compound, be specifically related to antineoplastic compound compound separation purge process, structural identification, the contents such as anti-tumour cell proliferative effect experiment.
Background technology
People early acute young grain leukemia is based on the acute leukemia of promyelocyte hyperplasia, is a kind of specific type of acute myelocytic leukemia (AML), is decided to be acute myelocytic leukemia M3 type by FAB cooperative groups.Acute promyelocytic leukemia is much clinically, and morbidity crowd is based on young person between 30 ~ 38 years old.China sickness rate exceed 10% than western countries, some areas (oil field, northeast) sickness rate in AML proportion up to 20% ~ 30%.
The herb of green onion lotus (Zephyranthescandida) Shi Suan section Zephyranthes per nnial herb green onion lotus (Zephyranthescandida (Lindl.) Herb).In Japan also known as " beautiful curtain ", originate in South America, the extensive introducing culture of south China, aboundresources.Among the peoplely to be used as medicine with complete stool, to have function that is calming the liver to stop the wind, heat radiation removing toxic substances; For acute infantile convulsion wind, epilepsy; Red and swollen for carbuncle sore outward.The plant Zephyranthesparul belonged to together in Peru is used as treating tumour, and green onion lotus is widely used in treating diabetes as medicinal plant in Africa.
Summary of the invention
We are under the guidance of antitumor activity screening, systematic study has been carried out to green onion lotus antitumor activity component, separation obtains compound 1-16, and wherein N-methylcrinasiadine, N-ethoxycarbonylethyl crinasiadine, N-ethoxycarbonylpropyl crinasiadine, N-phenethyl crinasiadine, N-isopentenyl crinasiadine, O-methylnerinine, 3-methyl-3,4-dihydroplicane, Candidine A and Candidine B are new compound.Structural formula is as shown in (I).By these 16 compounds to 5 kinds of human body tumour cell antitumor activities, find that compound 3,5,6,7,8 pairs of leukemia HL-60, K562, lung cancer A-549, liver cancer HepG2 and colorectal carcinoma HT-29 tumor cell propagation have inhibit activities.
The present invention relates to related alkaloids compound in green onion lotus separation preparation and it have suppress leukemia HL-60, K562, lung cancer A-549, liver cancer HepG2 and colorectal carcinoma HT-29 tumor cell propagation activity.Can as the medicine of the tumor diseases such as treatment leukemia, lung cancer, liver cancer, colorectal carcinoma.
Task of the present invention is to provide the compound had with structure shown in Formula Il,
Wherein
R 1can be following aromatic ring or heterocycle: pyrroline, 2-pyrroline, 1-pyrroline, 2-oxazoline, 3-oxazoline, 2-tetrahydroglyoxaline, pyrazoline, pyrroles, imidazoles, benzoglyoxaline, pyrazoles, indazole, pyridine, dihydro-pyrimidin, pyrimidine, phenyl ring;
R 2-R 10can be identical or different, can to distinguish, simultaneously or be hydrogen, hydroxyl, alkyl containing 1-8 carbon, halogen, nitro, the alkoxyl group of a 1-8 carbon, carbonyl, carboxyl, aldehyde radical or amino separately;
N is the number of methylene radical, can be 0-7.
Another task of the present invention is to provide the compound with structure shown in following formula III,
Wherein
R 1can be following aromatic ring or heterocycle: pyrroline, 2-pyrroline, 1-pyrroline, 2-oxazoline, 3-oxazoline, 2-tetrahydroglyoxaline, pyrazoline, pyrroles, imidazoles, benzoglyoxaline, pyrazoles, indazole, pyridine, dihydro-pyrimidin, pyrimidine, phenyl ring;
R 1-R 10can be identical or different, can to distinguish, simultaneously or be hydrogen, hydroxyl, alkyl containing 1-8 carbon, halogen, nitro, the alkoxyl group of a 1-8 carbon, carbonyl, carboxyl, aldehyde radical or amino separately;
X can be the acid ion of any one halogen or organic acid acid ion or mineral acid, and described organic acid acid ion or the acid ion of mineral acid can be SO 4 2-, NO 3 -, PO 3 2-, HCO 2 -, CH 3cO 2 -, CO 2 2-, oxalate denominationby, citrate ion, malate ion or lactate ion.
Another task of the present invention is to provide tool compound N-styroyl crinidine alkali, Candidine A and Candidine B, and its structural formula is respectively:
Above-claimed cpd provided by the invention has antitumor action, can be used for preparing antitumor drug, specifically can be used for the medicine preparing treatment leukemia, lung cancer, liver cancer or colorectal carcinoma.
Present invention also offers the plant origin of compound 1-16 and the structure of separation purification method and derivative and analogue thereof.
An embodiment provides the method for separating and preparing of N-phenethyl crinasiadine, Candidine A, Candidine B.
An alternative embodiment of the invention provides the experimental data of compound 1-16 to the inhibit activities of the active cells that blood sick HL-60, K562, lung cancer A-549, liver cancer HepG2 and colorectal carcinoma HT-29 tumor cell are bred.The anti-tumor activity of compound 1-16 is evaluated leukemia HL-60, K562, lung cancer A-549, liver cancer HepG2 and colorectal carcinoma HT-29 five kinds of human body tumour cells by mtt assay.Result shows: compound N styroyl crinidine alkali and Candidine A and Candidine B have remarkable inhibiting activity to leukemia HL-60, K562, lung cancer A-549, liver cancer HepG2 and colorectal carcinoma HT-29 five kinds of human body tumour cells, are all better than positive control drug cis-platinum.
Another embodiment of the present invention has carried out the mensuration of LD50 to compound Candidine A and Candidine B, result show compound Candidine A and Candidine B toxicity rank very low or nontoxic, oral safety.
Accompanying drawing explanation
Fig. 1: the separation preparation flow figure of N-phenethyl crinasiadine, Candidine A, Candidine B.
Fig. 2: Candidine A and Candidine B X-Ray scheme,
Embodiment
The separation preparation of embodiment 1:N-styroyl crinidine alkali, Candidine A, Candidine B
The dry herb (10kg) of green onion lotus extracts three times with 95% ethanol (containing 2%HCl) 25L cold soaking after pulverizing, 4th heating and refluxing extraction, with the aqueous solution 3L suspendible containing 2%HCl after united extraction liquid recycling design, 3L chloroform extraction four times, aqueous phase strong aqua adjusts pH value to alkalescence, again with 3L chloroform extraction four times, chloroform layer recycling design obtains total alkali.Total alkali with in press chromatographic system through silica gel column chromatography, chloroform to methanol elution gradient obtains five parts, and first part is through purification on normal-phase silica gel, and reversed-phase silica gel column chromatography, gel chromatography is separated with high performance liquid chromatography and obtains N-phenethyl crinasiadine.Part V entered reversed-phase silica gel column chromatography, and water, to methanol elution gradient, obtains three parts, and the 3rd part is obtaining the Candidine A of compound and the crystallization (in methyl alcohol) of Candidine B through silica gel column chromatography repeatedly, and schema is shown in Fig. 1.
Resolve through NMR and X-Ray test the absolute configuration (see Fig. 2) obtaining Candidine A and Candidine B, wherein the ratio of Candidine A and Candidine B is 7:3.
N-phenethyl crinasiadine (N-phenethylcrinasiadine): colourless powder, is soluble in chloroform, is insoluble to methyl alcohol.UV(CDCl 3)λmax(logε)270(4.08)，313(3.91)，341(3.76)，372(3.13)nm；IRv max2957，2924，2855，1747，1631，1600，1462，1310，1039，751cm -1；HRESIMSm/z344.1282[M+H] +(calcdforC 22H 18NO 3 +，344.12812)。
1HNMR(400MHz，CDCl 3)δ8.12(1H，dd，J＝8.0，0.8Hz，H-1)，7.93(1H，s，H-7)，7.65(1H，s，H-10)，7.52(1H，dd，J＝8.4，1.2Hz，H-3)，7.46(1H，d，J＝7.9Hz，H-4)，7.38(2H，t，J＝7.0Hz，H-15，17)，7.34(2H，d，J＝7.3Hz，H-14，18)，7.29(1H，ddd，J＝8.4，7.0，1.2Hz，H-2)，7.25(1H，t，J＝7.5Hz，H-16)，6.12(2H，s，H-OCH 2O)，4.58(2H，t，J＝8.3Hz，H-11)，3.07(2H，t，J＝8.6Hz，H-12)。
13CNMR(101MHz，CDCl 3)δ160.8(s，C-6)，152.5(s，C-9)，148.7(s，C-8)，138.8(s，C-13)，136.6(s，C-4a)，130.7(s，C-6a)，129.2(d，C-3)，129.0(d，C-14，18)，128.9(d，C-15，17)，126.9(d，C-16)，123.2(d，C-1)，122.2(d，C-2)，121.5(s，C-10b)，119.7(s，C-10a)，114.7(d，C-4)，106.7(d，C-7)，101.9(t，C-OCH 2O))，100.3(d，C-10)，44.6(t，C-11)，33.6(t，C-12)。
Candidine A and Candidine B (CandidineAandCandidineB): colourless prismatic crystal, is soluble in methyl alcohol, and water is insoluble to chloroform, and there is uv-absorbing at ultraviolet 254nm place.m.p.237℃，[α]25℃D+5.23°(c0.745，CH3OH)；UV(MeOD)λmax(logε)205(2.16)，245(1.44)，290(1.47)，360(0.51)，370(0.56)nm；IRv max3239，3003，1509，1489，1252，1132，1030，937，825cm -1；HRESIMSm/z332.1488([M-Cl -] +calcdforC 18H 23NO 5 +，332.1493).
Candidine A (CandidineA) 1hNMR (400MHz, MeOD) δ 7.03 (1H, s, H-10), 6.92 (1H, s, H-7), 6.42 (1H, m, H-1), 6.41 (1H, m, H-2), 6.04 (1H, s, H-6), 6.03 (2H, s, H-OCH 2o), 4.58 (1H, dd, J=12.7,6.1Hz, H-12 β), 4.16 (1H, dd, J=13.3,4.6Hz, H-4a), 4.04 (1H, s, H-3), 4.02 (1H, s, H-11), 3.40 (3H, s, H-OMe), 3.25 (1H, m, H-12 α), 3.23 (3H, s, H-NMe), 2.51 (1H, ddd, J=14.82,13.24,3.40, HzH-4). 13cNMR (101MHz, MeOD) δ 150.77 (C-8), 149.13 (C-9), 133.95 (C-10a), 131.09 (C-1), 126.88 (C-2), 125.22 (C-6a), 109.11 (C-7), 104.38 (C-10), 103.42 (C-OCH 2o), 96.10 (C-6), 77.94 (C-11), 72.33 (C-3), 71.72 (C-4a), 62.82 (C-12), 57.02 (C-OMe), 53.22 (C-10b), 43.69 (C-NMe), 26.1 (C-4).
Candidine B (CandidineB) 1hNMR (400MHz, MeOD) δ 7.07 (1H, s, H-10), 6.86 (1H, s, H-7), 6.42 (1H, m, H-1), 6.41 (1H, m, H-2), 6.03 (2H, s, H-OCH 2o), 5.64 (1H, s, H-6), 4.16 (1H, dd, J=13.3,4.6Hz, H-4a), 4.20 (1H, m, H-12 β), 4.04 (1H, s, H-3), 4.02 (1H, s, H-11), 3.63 (1H, d, J=13.5Hz, H-12 α), 3.40 (3H, s, H-OMe), 3.23 (3H, s, H-NMe), 2.40 (1H, m, H-4). 13cNMR (101MHz, MeOD) δ 151.08 (C-8), 149.13 (C-9), 133.95 (C-10a), 131.27 (C-1), 126.51 (C-2), 124.15 (C-6a), 109.88 (C-7), 104.38 (C-10), 103.42 (C-OCH 2o), 96.69 (C-6), 78.06 (C-11), 72.44 (C-3), 65.26 (C-4a), 68.57 (C-12), 57.02 (C-OMe), 53.80 (C-10b), 44.28 (C-NMe), 25.5 (C-4).
Embodiment 2: compound 1-16 is to the inhibit activities of the active cells that blood sick HL-60, K562, lung cancer A-549, liver cancer HepG2 and colorectal carcinoma HT-29 tumor cell are bred.
The anti-tumor activity of compound 1-16 is evaluated leukemia HL-60, K562, lung cancer A-549, liver cancer HepG2 and colorectal carcinoma HT-29 five kinds of human body tumour cells by mtt assay.Result is as shown in table 1 below:
Table 1 compound is to half growth inhibitory concentration IC50 (μM) of different tumor cell line
Experiment conclusion: compound N styroyl crinidine alkali and Candidine A and Candidine B have remarkable inhibiting activity to leukemia HL-60, K562, lung cancer A-549, liver cancer HepG2 and colorectal carcinoma HT-29 five kinds of human body tumour cells, are all better than positive control drug cis-platinum.
Embodiment 3: the mensuration of compound Candidine A and Candidine B (7:3) LD50
The mensuration of compound Candidine A and Candidine B LD50: regular grade kunming mice 12,20 ± 2g, male and female half and half, adaptability feeds rear fasting 12 hours, is assigned to the Oral Acute Toxicity that high dose group investigates III-6 immediately, often organizes male and female half and half.Gavage, observes the diet of animal in a week, movable, the situation such as Mao Ze and living or death.After gastric infusion, normally, without any toxic reaction, none is poisoned to death for animal appearance and behavior expression.Result to show when 40 times of effective reference dose without any toxic reaction, think compound Candidine A and Candidine B toxicity rank very low or nontoxic, oral safety, no longer increasing dose does toxicity test.
Therefore, compound Candidine A and Candidine B toxicity rank very low or nontoxic, oral safety.
Embodiment 4: compound Candidine A and Candidine B (7:3) tablet are prepared and method
Main medicinal raw material comprises: active substance Candidine A and Candidine B (7:3), the thinner of medicinal tablets, tablet lubricants, tackiness agent and disintegrating agent.Thinner can select one or more combinations in micro-starch, glycosides propylhomoserin, Sodium Hydroxymethyl Stalcs; Tackiness agent can select the one in starch slurry, PVP rubber cement, gelatine size; One in the selectable talcum powder of lubricant, Magnesium Stearate.Tablet stability is good.
Get Candidine A and Candidine B (7:3) 100mg, starch 24g, Microcrystalline Cellulose 24g, Sodium Hydroxymethyl Stalcs 64g, glycine 10g be porphyrize respectively, crosses 80 mesh sieves, the addition of equivalent mixes, and makes softwood with starch slurry (5%), granulates with 30 mesh sieve filters, dry under putting 70 DEG C of conditions, add Magnesium Stearate 0.15g after filtering whole grain with 40 mesh sieves again, mix, compressing tablet, packing, to obtain final product.

Claims (1)

1. from green onion lotus, be separated the method preparing Candidine A and Candidine B, comprise: after dry for green onion lotus herb is pulverized, get the ethanol 24.5L of 95%, add 0.5L hydrochloric acid, obtain the 95% ethanol 25L containing 2% hydrochloric acid, three times are extracted with the 95% ethanol 25L cold soaking containing 2% hydrochloric acid, 4th heating and refluxing extraction, with the aqueous solution 3L suspendible containing 2%HCl after united extraction liquid recycling design, 3L chloroform extraction four times, aqueous phase strong aqua adjusts pH value to alkalescence, again with 3L chloroform extraction four times, chloroform layer recycling design obtains total alkali, total alkali with in press chromatographic system through silica gel column chromatography, chloroform to methanol elution gradient obtains five parts, Part V is through reversed-phase silica gel column chromatography, water is to methanol elution gradient, obtain three parts, 3rd part is obtaining having the compound Candidine A of following structural formula and the crystallization of Candidine B through silica gel column chromatography repeatedly:
CN201310560305.3A 2011-12-22 2011-12-22 There is in green onion lotus the compound of antitumor action and method for separating and preparing thereof and application Expired - Fee Related CN103641839B (en)

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