CN104478939B - A kind of metal rhodium compound and its production and use - Google Patents
A kind of metal rhodium compound and its production and use Download PDFInfo
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- CN104478939B CN104478939B CN201410658206.3A CN201410658206A CN104478939B CN 104478939 B CN104478939 B CN 104478939B CN 201410658206 A CN201410658206 A CN 201410658206A CN 104478939 B CN104478939 B CN 104478939B
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Abstract
The invention discloses a kind of metal rhodium compound and its production and use, it is (the 1E of a chlorine one, 6E) 1,7 two (hydroxy phenyl of 3 methoxyl group 4) 4 (to ethylphenyl vinyl) 1,6 heptadiene 2,5 diketone First Five-Year Plan methyl cyclopentadienyls close rhodium (III), and it can be as the application for preparing treating cancer and anti-parasite medicine, its structural formula：
Description
Technical field
The present invention relates to chemical medicine field, especially a kind of metal rhodium compound and its production and use.
Technical background
Cis-platinum is a kind of heavy metal complex, and it is in the world for one of most commonly used 3 kinds of medicine for the treatment of cancer.It is suitable
Platinum can suppress the reproduction process of cell DNA, can suppress the synthesis of RNA and protein during high concentration, for treating cancer
When, the duplication of tumour cell, and the structure of damaging cells film can be suppressed, so as to kill tumour cell.Rhodium metal complex compound and
Cis-platinum is all heavy metal complex, and it can suppress the duplication of tumour cell as cis-platinum, at present to rhodium metal complex compound
Research is also less, but existing Research foundation shows rhodium metal complex compound in exploitation pharmaceutically with very big potentiality.
Curcumin chemical compounds have the effect such as reducing blood lipid, antitumor, anti-inflammatory, cholagogic, anti-oxidant, and curcumin
Compound is numerous due to its coordination site, it is easy to metal with a variety of coordination modes formation complex.Therefore the present invention is attempted with turmeric
Chlorins compound is that main part prepares metal rhodium compound, in theory, due to cooperateing with for metal rhodium and curcumin part
Effect, described metal rhodium compound is compared with pure curcumin, and antitumor cell ability and anti parasitic ability are stronger.At present with
Curcumin chemical compounds have no report for the rhodium complex of main part.
The content of the invention
It is an object of the invention to the deficiency for general chemicals, there is provided a kind of metal rhodium compound and its preparation side
Method and purposes, a kind of metal rhodium compound that can be applied as chemicals and preparation method thereof, utilize curcumin chemical combination
Thing coordination site is numerous, it is easy to which the characteristics of forming complex with metal with a variety of coordination modes and heavy metal rhodium compound can press down
The characteristics of DNA of tumor cell processed is replicated, makes rhodium compound combine to form a kind of new anticancer with curcumin chemical compounds and resist and posts
The stronger metal rhodium compound of infested ability, its can as anticancer and anti parasitic medicinal application.
The technical scheme that the present invention is provided is：
A kind of metal rhodium compound, wherein：
The chemical name of the metal rhodium compound is：(3- methoxyl group -4- the hydroxy benzenes of one chlorine, one (1E, 6E) -1,7- bis-
Base) -4- (to ethylphenyl vinyl) -1,6- heptadiene -2,5- diketone First Five-Year Plans methyl cyclopentadienyl conjunction rhodium (III)；
The structural formula of the metal rhodium compound is：
Preferably, in described metal rhodium compound, the compound is orange crystal and is soluble in organic solvent, its
Hydrogen nuclear magnetic resonance modal data is1H NMR：(ppm, CDCl3) δ=1.400 (6H, d, J=6.9Hz), 2.355 (3H, s), 2.92
(1H, m, J=6.8Hz), 5.43 (2H, d, J=6.5Hz), 5.58 (2H, d, J=6.2Hz), 7.85 (s, 1H), 7.78 (d, J=
15.5Hz, 1H), 7.47 (d, J=16.3Hz, 1H), 7.45 (d, J=8.3Hz, 2H), 7.13-7.16 (m, 3H), 7.05 (d, J
=1.6Hz, 1H), 7.08 (dd, J=8.3,1.6Hz, 1H), 6.92 (d, J=1.7Hz, 1H), 6.91 (d, J=15.5Hz,
1H), 6.91 (d, J=8.5Hz, 1H), 6.89 (d, J=8.5Hz, 1H), 6.82 (d, J=16.5Hz, 1H), 3.93 (s, 3H),
3.85 (s, 3H), 2.66 (q, J=7.55Hz, 2H), 1.23 (t, J=7.62Hz, 3H).
A kind of preparation method of metal rhodium compound, wherein, comprise the following steps：
Step 1: by 2,4- pentanediones, Vanillin, diboron trioxide is dissolved in concentration 90- jointly
After 100% DMF solution, nitrogen protection lower 70-90 DEG C of reaction 5-7 hour, and mixed in hydrochloric acid, standing precipitation obtain (1E, 3Z,
6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -3- hydroxyls -1,3,6- heptantriene -5- ketone, structural formula is as follows：
Step 2: by p-ethylbenzaldehyde and (1E, 3Z, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -3- hydroxyls -
1,3,6- heptantriene -5- ketone is dissolved in concentration 90-100% toluene, and then the acetic acid with concentration 90-100% is mixed, 100-150
DEG C reaction 5-10h, stand separate out (1E, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -4- (to ethylphenyl vinyl) -
1,6- heptadiene -2,5- diketone, structural formula is as follows：
Step 3: by (1E, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -4- (to ethylphenyl vinyl) -1,
6- heptadiene -2,5- diketone and dichloro (pentamethylcyclopentadiene base) close rhodium (III) dimer and are dissolved in absolute dichloromethane, and heating is stirred
Mix backflow 10-20 hours, after the completion of reaction solution be evaporated to it is a certain amount of obtain concentrated liquid, by the concentrated liquid of gained with it is dense
90-100% ether mixing is spent, orange crystal, the as (3- methoxyl group -4- hydroxyls of one chlorine of product, one (1E, 6E) -1,7- bis- is separated out
Base phenyl) -4- (to ethylphenyl vinyl) -1,6- heptadiene -2,5- diketone First Five-Year Plans methyl cyclopentadienyl conjunction rhodium (III).
Preferably, in the preparation method of described metal rhodium compound, each component consumption used difference in step one
For：2,4- pentanedione 0.05-0.5g, Vanillin 0.1-1g, diboron trioxide 0.1-5mmol, DMF 5-
20ml and 0.1-0.5M hydrochloric acid 1-10ml.
Preferably, in the preparation method of described metal rhodium compound, each component consumption used is respectively in step 2：
P-ethylbenzaldehyde 15-30mg, (1E, 3Z, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -3- hydroxyls -1,3,6- heptan three
Alkene -5- ketone 20-100g, toluene 5-20ml and acetic acid 0.1-1mg.
Preferably, in the preparation method of described metal rhodium compound, each component consumption used is respectively in step 3：
(1E, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -4- (to ethylphenyl vinyl) -1,6- heptadiene -2,5- diketone
20-50mg, dichloro (pentamethylcyclopentadiene base) close rhodium (III) dimer 30-60mg, absolute dichloromethane 5-10ml, concentrate
Body 1-5ml and ether 10-20ml.
A kind of purposes of metal rhodium compound, wherein, the metal rhodium compound is used to prepare treating cancer and parasite
The application of infection medicine.
A kind of purposes of metal rhodium compound, wherein, the metal rhodium compound can be made into injection, tablet, pill, glue
The form of wafer, suspending agent or emulsion.
The invention has the advantages that：First, there is metal rhodium compound of the present invention good suppression to swell
Oncocyte active effect, its medium effective concentration to tumour cell is between 2-5umol/mL, and pure curcumin is to tumour cell
Medium effective concentration between 20-40umol/mL, compound on tumor cell of the present invention has more preferable by contrast
Inhibition, its form that can be made into injection, tablet, pill, capsule, suspending agent or emulsion is used as cancer therapy drug.
Secondly, the present invention has excellent anti parasitic effect, and its medium effective concentration to plasmodium is 6-10umol/
ML, compared to the 30-40umol/mL of pure curcumin, compound of the present invention has more preferable insecticidal effect to plasmodium, can
To be used as antiparasitic medicine.
Finally, the preparation method of metal rhodium compound of the present invention is simple, and raw material is easy to get, with low excellent of cost
Gesture, compared to traditional anticancer anti-parasite medicine, cost reduction by more than 30%.
Embodiment
The present invention is elaborated with reference to embodiment, to make those of ordinary skill in the art refer to after this specification
It can implement according to this.
A kind of metal rhodium compound, wherein：
The chemical name of the metal rhodium compound is：(3- methoxyl group -4- the hydroxy benzenes of one chlorine, one (1E, 6E) -1,7- bis-
Base) -4- (to ethylphenyl vinyl) -1,6- heptadiene -2,5- diketone First Five-Year Plans methyl cyclopentadienyl conjunction rhodium (III)；
The structural formula of the metal rhodium compound is：
In described metal rhodium compound, the compound is orange crystal and is soluble in organic solvent, its nuclear magnetic resonance
Hydrogen modal data is1H NMR：(ppm, CDCl3) δ=1.400 (6H, d, J=6.9Hz), 2.355 (3H, s), 2.92 (1H, m, J=
6.8Hz), 5.43 (2H, d, J=6.5Hz), 5.58 (2H, d, J=6.2Hz), 7.85 (s, 1H), 7.78 (d, J=15.5Hz,
1H), 7.47 (d, J=16.3Hz, 1H), 7.45 (d, J=8.3Hz, 2H), 7.13-7.16 (m, 3H), 7.05 (d, J=1.6Hz,
1H), 7.08 (dd, J=8.3,1.6Hz, 1H), 6.92 (d, J=1.7Hz, 1H), 6.91 (d, J=15.5Hz, 1H), 6.91 (d,
J=8.5Hz, 1H), 6.89 (d, J=8.5Hz, 1H), 6.82 (d, J=16.5Hz, 1H), 3.93 (s, 3H), 3.85 (s, 3H),
2.66 (q, J=7.55Hz, 2H), 1.23 (t, J=7.62Hz, 3H).
A kind of preparation method of metal rhodium compound, wherein, comprise the following steps：
Step 1: by 2,4- pentanediones, Vanillin, diboron trioxide is dissolved in concentration 90- jointly
After 100% DMF solution, preferably pure DMF solution, nitrogen protection lower 70-90 DEG C of reaction 5-7 hours, wherein it is preferred that 80 DEG C and 6 small
When, then with mixed in hydrochloric acid, stand precipitation obtain (1E, 3Z, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -3- hydroxyls -
1,3,6- heptantriene -5- ketone, structural formula is as follows：
Step 2: by p-ethylbenzaldehyde and (1E, 3Z, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -3- hydroxyls -
1,3,6- heptantriene -5- ketone is dissolved in concentration 90-100% toluene, preferably pure toluene, and then the acetic acid with concentration 90-100% is mixed
Close, wherein it is preferred that pure acetic acid, 100-150 DEG C of reaction 5-10h, wherein it is preferred that 100 DEG C and 6h, standing separate out (1E, 6E) -1,7- bis-
(3- methoxyl group -4- hydroxy phenyls) -4- (to ethylphenyl vinyl) -1,6- heptadiene -2,5- diketone, structural formula is as follows：
Step 3: by (1E, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -4- (to ethylphenyl vinyl) -1,
6- heptadiene -2,5- diketone and dichloro (pentamethylcyclopentadiene base) close rhodium (III) dimer and are dissolved in absolute dichloromethane, and heating is stirred
Mix backflow 10-20 hour, preferably 15 hours, after the completion of reaction solution be evaporated to it is a certain amount of obtain concentrated liquid, addition concentration
90-100% ether, separates out orange crystal, the as (3- methoxyl group -4- hydroxy benzenes of one chlorine of product, one (1E, 6E) -1,7- bis-
Base) -4- (to ethylphenyl vinyl) -1,6- heptadiene -2,5- diketone First Five-Year Plans methyl cyclopentadienyl conjunction rhodium (III).
In the preparation method of described metal rhodium compound, each component consumption used in step one is respectively：2,4- penta
Diketone 0.05-0.5g, Vanillin 0.1-1g, diboron trioxide 0.1-5mmol, DMF 5-20ml and
0.1-0.5M hydrochloric acid 1-10ml, wherein it is preferred that 2,4- pentanedione 0.095g, Vanillin 0.12g, three oxygen
Change two boron 1mmol, DMF 10ml and 0.5M hydrochloric acid 8ml.
In the preparation method of described metal rhodium compound, each component consumption used is respectively in step 2：To ethylo benzene
Formaldehyde 15-30mg, (1E, 3Z, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -3- hydroxyls -1,3,6- heptantriene -5- ketone
20-100g, toluene 5-20ml and acetic acid 0.1-1mg, wherein it is preferred that p-ethylbenzaldehyde 20mg, (1E, 3Z, 6E) -1,7- bis-
(3- methoxyl group -4- hydroxy phenyls) -3- hydroxyls -1,3,6- heptantriene -5- ketone 40g, toluene 10ml and acetic acid 0.5mg.
In the preparation method of described metal rhodium compound, each component consumption used is respectively in step 3：(1E, 6E)-
1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -4- (to ethylphenyl vinyl) -1,6- heptadiene -2,5- diketone 20-50mg,
Dichloro (pentamethylcyclopentadiene base) close rhodium (III) dimer 30-60mg, dichloromethane 5-10ml, concentrated liquid 1-5ml and
Ether 10-20ml, wherein it is preferred that (1E, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -4- (to ethylphenyl vinyl) -
1,6- heptadiene -2,5- diketone 30mg, dichloro (pentamethylcyclopentadiene base) close rhodium (III) dimer 40mg, dichloromethane
8ml, concentrated liquid 3ml and ether 15ml.
A kind of purposes of metal rhodium compound, wherein, the metal rhodium compound is used to prepare treating cancer and parasite
The application of infection medicine.
A kind of purposes of metal rhodium compound, wherein, the metal rhodium compound can be made into injection, tablet, pill, glue
The form of wafer, suspending agent or emulsion.
Embodiment 1
First, prepared by product
0.095g 2 is weighed, 4- pentanediones, 0.12g Vanillins, 1mmol diboron trioxides are common
Be dissolved in 10ml DMF solutions, after lower 80 DEG C of reactions of nitrogen protection 6 hours, add 8ml 0.5M hydrochloric acid, stand precipitation obtain (1E,
3Z, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -3- hydroxyls -1,3,6- heptantriene -5- ketone；By 20mg to ethylo benzene
Formaldehyde and 40mg (1E, 3Z, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -3- hydroxyls -1,3,6- heptantriene -5- ketone are molten
In 10ml toluene, 0.5mg acetic acid is added, 150 DEG C of reaction 8h stand and separate out (3- methoxyl group -4- the hydroxy benzenes of (1E, 6E) -1,7- bis-
Base) -4- (to ethylphenyl vinyl) -1,6- heptadiene -2,5- diketone；By 30mg (1E, 6E) -1,7- bis- (3- methoxyl groups -
4- hydroxy phenyls) -4- (to ethylphenyl vinyl) -1,6- heptadiene -2,5- diketone and 40mg dichloro (pentamethylcyclopentadienes
Base) to close rhodium (III) dimer and be dissolved in 8ml dichloromethane, heating stirring is flowed back 16 hours, and solution is evaporated surplus after the completion of reaction
3ml liquid, adds 15ml ether, separates out orange crystal, the as (3- methoxyl group -4- hydroxyls of one chlorine of product, one (1E, 6E) -1,7- bis-
Base phenyl) -4- (to ethylphenyl vinyl) -1,6- heptadiene -2,5- diketone First Five-Year Plans methyl cyclopentadienyl conjunction rhodium (III).
2nd, anti tumor activity in vitro is tested
Experimentation：Using MTT methods, vitro cytotoxicity measure is carried out.By metal rhodium compound obtained above with
The cell lines of stomach cancer SGC 7901 and liver cancer BEL-7404 cell lines 72 hours action time of difference, then measure metal rhodium compound
To the medium effective concentration (IC of tumor cell line50).Pure curcumin is tested using same experimental method, turmeric is obtained
Medium effective concentration of the element to tumor cell line.
Experimental result：
Medium effective concentration (the IC of the metal rhodium compound of table 1 and curcumin to tumor cell line50)(umol/mL)
| SGC-7901 | BEL-7404 | |
| Compound of the present invention | 4.5±1.7 | 3.2±2.7 |
| Curcumin | 25.3±3.4 | 22.1±3.9 |
From the results shown in Table 1, metal rhodium compound of the invention shows through anticancer experiment in vitro, the compound
With strong antitumor activity, and compared with pure curcumin, medium effective concentration is much lower, and effect is more obvious.The present invention is
The new antineoplastic of research and development provides new thinking.
3rd, anti parasitic is tested
Experimentation：This hair is assessed using the plasmodium cultivation of the quantitative red blood cell of fluorecyte classification analysis (FACS)
The Antiparasitic Activity of bright product.The metal rhodium compound that embodiment 1 is obtained is dissolved in 1mlDMSO, then with by
25mmol/L 4- hydroxyethyl piperazineethanesulfonic acid buffer solutions, 32mmol/L NaHCO3The RPMI 1640 being made into 10% human plasma
Cell culture medium dilutes 200 times.Sample solution is then made into 11 kinds of various concentrations with the method for 2 times of dilutions successively, by 1ml, 2
×106/ ml plasmodium is added in solution, and 5%CO is put at 37 DEG C248h is cultivated in incubator.Add the diamidino benzene of 1ml 3%
Base indoles solution, is further cultured for 18h, determines red blood cell number with fluorecyte classification analysis instrument, it can be deduced that various concentrations sample pair
The inhibiting rate of plasmodium, calculates IC50Value.Curcumin is tested using same experimental method, and calculates IC50Value.
Experimental result：
Medium effective concentration (the IC of the metal rhodium compound of table 2 and curcumin to parasite50)(umol/mL)
| Plasmodium | |
| Compound of the present invention | 8.2±1.9 |
| Curcumin | 30.8±3.4 |
From the results shown in Table 2, metal rhodium compound of the invention shows through anti parasitic experiment, compound tool
There is strong Antiparasitic Activity, and compared with pure curcumin, Antiparasitic Activity effect is more obvious.
Although embodiment of the present invention is disclosed as above, it is not restricted in specification and embodiment listed
With it can be applied to various suitable the field of the invention completely, can be easily for those skilled in the art
Other modification is realized, therefore under the universal limited without departing substantially from claim and equivalency range, the present invention is not limited
In specific details and shown here as the legend with description.
Claims (4)
1. a kind of preparation method of metal rhodium compound, it is characterised in that：
The chemical name of the metal rhodium compound is：One chlorine one (1E, 6E) -1,7- two (3- methoxyl group -4- hydroxy phenyls) -4-
(to ethylphenyl vinyl) -1,6- heptadiene -2,5- diketone First Five-Year Plans methyl cyclopentadienyl closes rhodium (III)；
The structural formula of the metal rhodium compound is：
And be made by the following method：
Step 1: by 2,4- pentanediones, Vanillin, diboron trioxide is dissolved in concentration 90-100% jointly
DMF solution, after nitrogen protection lower 70-90 DEG C of reaction 5-7 hour, with mixed in hydrochloric acid, standing precipitation obtains (1E, 3Z, 6E) -1,
7- bis- (3- methoxyl group -4- hydroxy phenyls) -3- hydroxyls -1,3,6- heptantriene -5- ketone, structural formula is as follows：
Step 2: by p-ethylbenzaldehyde and (1E, 3Z, 6E) -1,7- two (3- methoxyl group -4- hydroxy phenyls) -3- hydroxyl -1,3,
6- heptantriene -5- ketone is dissolved in concentration 90-100% toluene, and then the acetic acid with concentration 90-100% is mixed, and 100-150 DEG C anti-
5-10h is answered, stands and separates out (1E, 6E) -1,7- bis- (3- methoxyl group -4- hydroxy phenyls) -4- (to ethylphenyl vinyl) -1,6-
Heptadiene -2,5- diketone, structural formula is as follows：
Step 3: by (1E, 6E) -1,7- two (3- methoxyl group -4- hydroxy phenyls) -4- (to ethylphenyl vinyl) -1,6- heptan
Diene -2,5- diketone and dichloro (pentamethylcyclopentadiene base) close rhodium (III) dimer and are dissolved in absolute dichloromethane, and heating stirring is returned
Stream 10-20 hours, after the completion of reaction solution be evaporated to it is a certain amount of obtain concentrated liquid, by the concentrated liquid and concentration of gained
90-100% ether mixing, separates out orange crystal, the as (3- methoxyl group -4- hydroxyls of one chlorine of product, one (1E, 6E) -1,7- bis-
Phenyl) -4- (to ethylphenyl vinyl) -1,6- heptadiene -2,5- diketone First Five-Year Plans methyl cyclopentadienyl conjunction rhodium (III)；
Wherein, each component consumption used in step one is respectively：2,4- pentanedione 0.05-0.5g, 3- methoxyl group -4- hydroxy benzenes
Formaldehyde 0.1-1g, diboron trioxide 0.1-5mmol, DMF 5-20ml and 0.1-0.5M hydrochloric acid 1-10ml；
Each component consumption used is respectively in step 2：P-ethylbenzaldehyde 15-30mg, (the 3- methoxies of (1E, 3Z, 6E) -1,7- two
Base -4- hydroxy phenyls) -3- hydroxyl -1,3,6- heptantriene -5- ketone 20-100g, toluene 5-20ml and acetic acid 0.1-1mg；
Each component consumption used is respectively in step 3：(1E, 6E) -1,7- two (3- methoxyl group -4- hydroxy phenyls) -4- is (to second
Base phenyl vinyl) -1,6- heptadiene -2,5- diketone 20-50mg, dichloro (pentamethylcyclopentadiene base) close rhodium (III) dimerization
Body 30-60mg, absolute dichloromethane 5-10ml, concentrated liquid 1-5ml and ether 10-20ml.
2. the preparation method of metal rhodium compound as claimed in claim 1, it is characterised in that the compound is orange crystal
And organic solvent is soluble in, its hydrogen nuclear magnetic resonance modal data is1H NMR:(ppm,CDCl3) δ=1.400 (6H, d, J=
6.9Hz), 2.355 (3H, s), 2.92 (1H, m, J=6.8Hz), 5.43 (2H, d, J=6.5Hz), 5.58 (2H, d, J=
6.2Hz), 7.85 (s, 1H), 7.78 (d, J=15.5Hz, 1H), 7.47 (d, J=16.3Hz, 1H), 7.45 (d, J=8.3Hz,
2H), 7.13-7.16 (m, 3H), 7.05 (d, J=1.6Hz, 1H), 7.08 (dd, J=8.3,1.6Hz, 1H), 6.92 (d, J=
1.7Hz, 1H), 6.91 (d, J=15.5Hz, 1H), 6.91 (d, J=8.5Hz, 1H), 6.89 (d, J=8.5Hz, 1H), 6.82
(d, J=16.5Hz, 1H), 3.93 (s, 3H), 3.85 (s, 3H), 2.66 (q, J=7.55Hz, 2H), 1.23 (t, J=7.62Hz,
3H)。
3. a kind of purposes of metal rhodium compound made from preparation method as claimed in claim 1, it is characterised in that the gold
Category rhodium compound is used for the application for preparing treating cancer and parasitic infection medicine.
4. a kind of purposes of metal rhodium compound made from preparation method as claimed in claim 3, it is characterised in that the gold
Category rhodium compound can be made into the form of injection, tablet, pill, capsule, suspending agent or emulsion.
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| Synthesis and Identification of New 4-Arylidene Curcumin Analogues as Potential Anticancer Agents Targeting Nuclear Factor-KB Signaling Pathway;Xu Qiu等，;《J. Med. Chem.》;20101111;第53卷(第23期);第8260-8273页，尤其是第8261页图1、 * |
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