CN1255494A - Polyacetyl acetogenins for eliminating HIV virus and treating AIDS - Google Patents

Polyacetyl acetogenins for eliminating HIV virus and treating AIDS Download PDF

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CN1255494A
CN1255494A CN 99117242 CN99117242A CN1255494A CN 1255494 A CN1255494 A CN 1255494A CN 99117242 CN99117242 CN 99117242 CN 99117242 A CN99117242 A CN 99117242A CN 1255494 A CN1255494 A CN 1255494A
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aids
thf
tetrahydrofuran
ring
immune deficiency
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杨仁洲
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Abstract

The present invention discloses an acetogenins with tetrahydrofuran ring structure, which have strong suppression and elimination action to SIV or HIV-1 viruses and have high curative action to influence and common cold caused by influenza virus and nasal virus, so it is going to be a new medicine for HIV virus and AIDS.

Description

Remove the poly-acetyl genin of HIV virus, treatment acquired immune deficiency syndrome (AIDS)
The present invention relates to a kind of peaceful compounds of poly-acetyl that contains tetrahydrofuran (THF) ring and lactone ring five membered feature structure.
Annona lactone (Annonaceous acetogenins) is the poly-acetyl genin compounds of a class annonaceae plant specific, first compound uvaricin[Joladet al. of this compounds, J.org.Chem., 47:3151-3153, (1982)] be found since, so far nearly 200 compounds are found, these compounds have one, two or three tetrahydrofuran (THF) rings and a saturated or unsaturated lactone ring five membered, and performance has pair cotten aphid, insects such as mosquito larvae nematode have insecticidal activity, to the KB cell, qPS, 3PS, A-549, MCF-7, JEG-3 such as L-1210 have stronger restraining effect.Mikolajczak etc. successively obtained two U.S.'s patent of invention [U, S.Patent NO.4721727, Jan.26,1988 that are used for Pest Control in 1988 and 1989; U.S.Patent NO.4855319, Aug.8,1989], Mclaughlin etc. obtained a treatment tumor chemotherapeutic drug in 1993 the U.S. uses patent [U, S.PatentAppl., serial no.07/336233, field April, 11.1989].Its patent of invention compound pattern is as follows
Figure A9911724200041
The desirable following form of A
Figure A9911724200042
With
Figure A9911724200043
R 1R 2Can choose: H, H; H, OH; H, OAC and=0.R 1R 2Oxidation replaces sum≤6.
M=9～15, n=10～18, r=, w=1 or 2.
Since finding the first acquired immune deficiency syndrome (AIDS) case the eighties, acquired immune deficiency syndrome (AIDS) spreads in the whole world, is called as " century plague ".Die from nearly 1,400 ten thousand people of number of HIV infection/acquired immune deficiency syndrome (AIDS) and related complication during the last ten years, 4,000 ten thousand HIV infection/AIDS patient still has an appointment at present.The inhibitor of clinical treatment HIV infection/AIDS patient's medicine such as viral reverse transcription, viral DNA integrase inhibitor, hiv protease inhibitor etc. all are the medicines at virus particle at present, can not remove the viral DNA that is integrated in the host cell chromosome DNA chain, therefore patient's medication throughout one's life is with the control virus replication, because these medicines have injury equally to normal cell, the bigger effect of paying is arranged; HIV virus escapes or resists the effect of medicine by suddenling change, promptly long-term prescription HVI virus will develop immunity to drugs to medicine.
Order of the present invention is to provide a kind of poly-acetyl genin of the HIV of removing viral therapy acquired immune deficiency syndrome (AIDS), its mechanism of action is different from present clinical treatment HIV infection/acquired immune deficiency syndrome (AIDS) and other viral infection treatment of diseases medicines fully, the effect that the cell that this medicine infects SIV (acute simian immunodeficiency virus), HIV has intensive to suppress virus replication, remove virus.
The structural pattern of The compounds of this invention is:
Figure A9911724200051
F can choose following form With
Figure A9911724200053
X, Y can choose: H, H; H, OH; H, OAC and=0
A=4～12, B=5～15, D=1,2 or 3
Be included in the structural pattern (I), its compound can obtain from sweetsop (Annona sqamosaL.) corossol (Annona muricata L.), Australia sweetsop (Annonacherimolia, ex squamosa), Hainan brother receive the seed of perfume (or spice) (Goniothalamus howii Merr.etChun) or leaf.They contain a tetrahydrofuran (THF) ring or two adjacent tetrahydrofuran (THF) rings or three tetrahydrofuran (THF) rings that are linked to be wire arrangement adjacency, the five-ring lactone that α who has a methyl, β one are unsaturated or saturated or have the five-ring lactone of acetonyl, and by 5～15 CH 2The carbochain of forming links together, and has hydroxyl, ketone group, the replacement of acetoxyl group group on the carbochain of both sides usually.Their chemical structural formula is as follows:
R 1=H, R 2The peaceful first of=OH Arnold (AnnoninI) (II)
R 1=OH, R 2(AnnoninVI) (III) rather for=H Arnold
Sweetsop Xi Ningjia (squamosinin A)
Neo-annoacin-10-one (neo-annoacin-10-one)
Figure A9911724200064
Hainan GONIOTHALAMIN is heptan (howiicin FG)
The anti-HIV of compound of the present invention infects, its mechanism of action of treatment acquired immune deficiency syndrome (AIDS) is to attack the coenzyme system of infected cell (cell antigen), it is synthetic to block its ATP, make that to be in ATP originally synthetic vigorous, the metabolism that massive duplication virus also expends the infected cell of a large amount of ATP changes the scarce external energy immediately into, the anoxybiotic endogenous metabolism, follow the exhaustion that ATP stores in the born of the same parents, infected cells inevitable trend apoptosis, startup along with the apoptosis process, the endogenous dna restriction endonuclease of cell, protein decomposition enzymes etc. are the DNA of virus, RNA, functional proteins etc. are degraded one by one, remove.Therefore, compound of the present invention not only suppresses duplicating of virus, and can also dispose the viral DNA that is integrated in the host cell chromosome.Use the viral therapy of drug-induced infected cells apoptosis removing that the present invention makes, the patient might reach clinical cure through the treatment of medication after a while.
The effect test-results of the external anti-SIV of compounds more of the present invention sees Table 1.Wherein the peaceful first of compound Arnold (II), Arnold the effect of (III) is best rather, (II) 10 -5Ug/ml (1.61 * 10 -5UM) to cell antigen inhibiting rate 94.3%, suitable with the effect of AZT2uM the time, restraining effect (II) is equivalent to 10 of AZT2uM 5Doubly, virus titer descends and is better than AZT, and culturing cell is not found pathologies such as cavity, synplasm, is better than the AZT that contrasts yet.
Table 1, the dense rare pair cell cell antigen virus of the external anti-SIV activity test catalogue number(Cat.No.) of The compounds of this invention is dripped the cytopathy result
Degree is released toxicity inhibiting rate (%) degree decline (CPE) and is judged
Degree log2
1ug/ml 10 -5+ 94.3 2 8-highly suppress (II) 10 -6+ 53.9 2 5+ moderate suppresses
10 -7-20.0 2 0+++unrestraint
1ug/ml 10 -5+ 85.7 2 7-highly suppress (III) 10 -6+ 59.6 2 5+ moderate suppresses
10 -7-26.1 2 0+++unrestraint
1ug/ml 10 -3-48.6 2 1+ unrestraint or light (V) degree suppress
10 -4-34.4 2 0+++unrestraint
10 -5-5.7 2 0++ ++ unrestraint
1ug/ml 10 -3-31.4 2 0+ unrestraint (VI) 10 -4-25.7 2 0++ ++ unrestraint
10 -5-2.9 2 0++ ++ AZT 2 μ M-94.1 2 7+ highly suppress
Experiment cell CEM X174 cells, SIV virus adds simultaneously with medicine.
The dense rare pair cell cell antigen virus of the external anti-SIV activity test of the present invention (continuing) catalogue number(Cat.No.) is dripped the cytopathy result
Degree is released toxicity inhibiting rate (%) degree decline (CPE) and is judged
Degree log2
1ug/ml 10 -4-57.1 2 7++ moderate suppresses (II) 10 -6-20.0 2 0++, +++unrestraint (III) 1ug/ml 10 -4+ 82.9 2 8+ highly suppress
10 -6-57 2 1++, +++unrestraint (V) 1ug/ml 10 -4+ 57.1 2 4++ moderate suppresses
10 -6-34.3 2 0+++unrestraint
1ug/ml 10 -4-80.0 2 5+ moderate suppresses (VI) 10 -6-22.9 2 2++ the unrestraint experimental cell is CEM X174 cells.The SIV adherent cell just adds medicine after 4 hours.
Below in conjunction with embodiment the present invention is described in detail.
Embodiment one
Vegetable material extracts
Originate in the distinctive annonaceae plant Hainan brother of Hainan Province China and receive perfume (or spice) (Gonithalamushowii Merr.et Chun) seed and smash (2.5Kg) after drying naturally to pieces, put in the percolator, add sherwood oil (bp60～90 ℃) diacolation, 20 liters of transudates (F001).The sherwood oil transudate reclaims sherwood oil, places cooling during to about 3 liters of remaining volume, adds 80% ethanol (V/V) extraction subsequently, uses 500ml at every turn, and totally 6 times, 3000ml.80% alcohol extraction partial concentration thing (F003) is merged into F004 with acetone transudate (F002) liquid enriched material, further removes solvent under reduced pressure, adds a small amount of petroleum ether degreasing, and resistates (F005) is used acetone solution, mixes and stirs with 250 gram silica gel, dries, and is standby.
The F005 column chromatography
Silica gel 1.5Kg dry column-packing, the silica gel of absorption F005 places the post upper end, use following elutriant wash-out in turn: sherwood oil, sherwood oil one ethyl acetate mixed solution (95: 5,90: 10,85: 15,80: 20,70: 30,50: 50), ethyl acetate, use ethanol elution at last, obtained howiicins D at 90: 10～50: 50 wash-out positions of sherwood oil one ethyl acetate. penta. oneself and heptan (howiicins D.E.FandG).
Hainan GONIOTHALAMIN and heptan (howiicins Fand G) mixed crystal, white needle, mp85-87 ℃, [α] D+ 8.82 ° of (C0.884, CHCl 3), C35H64O7, M=596, 1HNMR (600MH z, in CDCl 3, δ ppm, JH Z): 0.88 (3H, t, J=7), 1.39 (3H, d, J=6.6), 3.43 (1H, m), 3.82 (1H, m), 3.88 (1H, m), 3.89 (1H, m), 5.05 (1H, q, J=6.6), 7.18 (1H, brs). 13CNMR (100.614MH z, inCDCl 3, δ ppm): 174.63 (3), 151.89 (d), 131.14 (s), 81.86 (d, F), 81.81 (d, G) 79.34 (d, F), 79.33 (d, G), 78.01 (d), 74.75 (d, F), 74.53 (d), 74.42 (d, G), 74.38 (d, F), 74.29 (d, G), 69.89 (d), 37.30 (t), 35.45 (t), 33.71 (t), 33.51 (t), 33.36 (t), 32.41 (t), 31.39 (t), 30.45-29.10 (t), 28.43 (t), 26.13 (t), 25.78 (t), 25.75 (t), 25.51 (t), 22.70 (t), 19.11 (q), 14.12 (q), EI-MS.m/Z:598 (M ++ 2), 381,363,351,333,315,281,263,239,221,197.
Embodiment two.
Vegetable material extracts.
The corossol seed is cleaned and is dried, smash back sherwood oil (bp60-90 ℃) lixiviate to pieces, continue and use acetone extraction, resistates and silica-gel powder mixed and stirred and dry after the acetone leach liquor concentrated, fine ground, by sample acetone extract (doing): silica gel=1: 30 carries out silica gel column chromatography to be separated, and makes eluent with sherwood oil, different ratios sherwood oil one ethyl acetate mixed solution, successively must S 1-S 13Totally 13 crystallizations.
S 8: Neo-annoacin-10-one (neo-annonacin-10-one) colourless crystallization, mp72.5-75 ℃, [α] D+ 17.3 ° of (C=1.15, CHCl 3)+20 ° (C=1.55, CH 3OH) C 35H 62O 7(M=594).1HNMR(300MH Z，inCDCl 3，δ?ppm，JH Z)：0.84(3H，t，J＝7)，2.39(5H，m)，2.49(1H，dd，J＝14，3.2)，3.37(2H，m)，3.78(3H，m)，5.03(1H，dd，J＝6.8，1.5)，7.16(1H，d，J＝1.5)， 13CNMR(100MH Z，inCDCl 3，δ.ppm)：211.62(s)，174.6(s)，151.97(d)，131.01(s)，82.67(d，2xc)，78.04(d)，74.03(d)，73.34(d)，68.89(d)，42.62(t)，42.54(t)，19.05(q)，EI-MSm/z：594(M+)，576，558，540，465，447，429，407，395，389，379，377，359，335，325(100)，308，307，289，271，239，221，203。
Embodiment three
Sweetsop (Annona squamosa L.) seed dries naturally, smashs (2446 gram) to pieces.Put and use sherwood oil (bp60-90 °) 20 liters of cold diacolations (F001) in the percolator, continue with 20 liters of diacolations of acetone (F002).F001 is concentrated into and adds the 600ml petroleum ether dissolution again after no sherwood oil steams, and with 80% methanol extraction 5 times, each 150ml, 750ml (F003) .F003 is concentrated into no methyl alcohol and steams adding ethyl acetate 100ml dissolving, anhydrous sodium sulfate drying altogether, filter, steam in after 14.4 grams (F004).
The F004 column chromatography
Silica gel 560g, F004 14.4 gram dry method upper props are used sherwood oil, sherwood oil one ethyl acetate (95: 5,90: 10,80: 20,70: 30,50: 50), vinyl acetic monomer, acetone is wash-out in succession, obtain F011 respectively, F012, F013, F043, the F044 component, the F038-F041 merging obtains 5.25g (F050).
The F050 column chromatography.
Silica gel 230 grams.F050 5.25 gram, the dry method upper prop, successively with sherwood oil, contain sherwood oil, the acetone wash-out of 5%, 8%, 10%, 20% acetone, obtain F051 respectively, F052, F063, F064, F065 component.F055, the F056 component merges after silica gel G preparation property is analysed clearly layer by layer, and developping agent is a chloroform: acetone: methyl alcohol (50: 10: 1) obtains compd A 7.
A7, sweetsop Xi Ningjia (squamocinin A). colourless amorphous substance, C36H62O8 (M=622), [α] D+24.7 ° (C=1.4, CHCl3). 1HNMR(300MH Z，inCDCl 3，δppm，JH Z)：0.85(3H，t，J＝6.9)，1.43(3H，d，J＝6.8)，3.36(1H，m)，3.75-3.90(8H，m)，5.04(1H，q，J＝6.8)，7.16(1H，br.s). 13CNMR(75MHZ，inCDCl3，δppm)：174，60(s)，151.77(d)，131.18(s)，83.22(d)，83.16(d)，82.78(d)，82.68(d)，82.50(d)，81.78(d)，77.96(d)，74.06(d)，71.32(d)，69.97(d)，19.10(d)，14.10(d)，EI-MS?m/z：622(M+)，604，586，568，551，498，451，433，415，414，381，363，345，311(100)，293，275，241，141。
Embodiment four
Sirikaya seed 4.5kg, with 95% ethanol lixiviate three times, extracting solution merges concentrating under reduced pressure after pulverizing, and resistates is successively used sherwood oil, chloroform extraction.The sherwood oil part is stripped with 85% methanol aqueous solution again, the extraction liquid evaporated under reduced pressure, and resistates separates through silica gel column chromatography, acetone one sherwood oil (5: 95,10: 90.15∶85，20∶80。30: 70) gradient elution, obtain the F1-80 component, from F42-50, obtain compound a nnonin VI (III), refining through little silicagel column, get the colourless crystallization thing in the vinyl acetic monomer.After merging, F58～72, obtain compound a nnonin I (II) again through silica gel column chromatography.
The peaceful first of Arnold (Annonin I), the amorphous or white crystals of white, mp44.5-46 °, [α] D+22.1 ° (C=0.5, CHCl3), C37H66O7 (M=622).UV go into max:211nm (E 10690, MeOH), 1HNMR (400MH Z, in CDCl3, δ ppm, JHz): 0.82 (3H, t, J=7), 1.35 (3H, d, J=6.8), 3.35 (1H, m), 3.53 (1H, m), 3.75 (1H, m), 3.80 (1H, and m) 3.83 (2H, m), 3.86 (1H, m) 4.94 (1H, dq, J=6.8,1.2), 6.94 (1H, d, J=1.2) .13CNMR (100MH Z, in CDCl3, δ ppm): 173.8 (s), 148.8 (d), 134.2 (s), 83.3 (d), 82.7 (d), 82.4 (d), 82.1 (d), 77.3 (d), 74.1 (d), 71.6 (d), 71.3 (d), 19.1 (q), 14.0 (q), EI-MS m/z:622 (M+), 604,586,568,519,501,483,465,417,399,347,329,319,295 (100), 267,239,203,195.
Arnold is (annonin VI) rather, colourless crystallization, mp77-78 °, [α] D+15.1 ° of (C=0.7, MeOH) .C37H66O 7(M=622) .UV goes into max:211.5nm (E 10631, MeOH).1HNMR(400MHz，in?CDCl3，δppm，JHz)：0.84(3H，t，J＝7.2)，1.37(3H，d，J＝6.8)，3.36(1H，m)，3.81(4H，m)，3.90(2H，m)，5.02(1H，q，J＝6.8)，6.96(1H，S).13CNMR(100MHz，in?CDCl3，δppm)：174.6(s)，151.7(d)，131.1(s)，83.2(d)，82.8(d)，82.5(d)，82.2(d)，77.9(d)，74.1(d)，71.3(d)，69.9(d)，19.1(q)，14.1(q).EI-MS?m/z：622(M+)，604，586，568，451，433，415，381，363，345，311(100)，293，275，241。
Embodiment five
The intravenous injection medication
(1) the peaceful first 1mg of Arnold
(2) soybean oil 5g
(3) Yelkin TTS 2.5g
(4) glycerine (glycerin) 2g
(5) distilled water for injection 100ml
(1) adds (2) in the last prescription, and (3) dissolving adds (4) and (5) emulsification again, obtains intravenous injection.
Embodiment six
The intravenous injection medication
(1) the peaceful 1mg of Arnold
(2) soybean oil 5g
(3) Yelkin TTS 2.5g
(4) glycerine (glycerin) 2g
(5) distilled water for injection adds to 100ml
Disposal is with embodiment five.
Embodiment seven
(1) the peaceful first 0.80mg of Arnold
(2) the peaceful 0.2mg of Arnold
(3) soybean oil 5g
(4) Yelkin TTS 2.5g
(5) glycerine (glycerin) 2g
(5) distilled water for injection adds to 100ml
After (1), (2) add (3), (4) dissolving in the last prescription, add (5) and (6) emulsification again, obtain intravenous injection (microemulsion).

Claims (3)

  1. One kind remove HIV virus, the treatment acquired immune deficiency syndrome (AIDS) poly-acetyl genin, the structural pattern that it is characterized by it is:
    Figure A9911724200021
    F can choose following form in the formula
    X, Y can choose: H, H; H, OH; H, OAC and=0
    A=4～21, B=5～15, D=1,2 or 3
  2. 2. the poly-acetyl genin of removing HIV virus according to claim 1, treatment acquired immune deficiency syndrome (AIDS), it is characterized by compound a tetrahydrofuran (THF) ring or two adjacent tetrahydrofuran (THF) rings or three tetrahydrofuran (THF) rings that connect into wire arrangement adjacency are arranged, the five-ring lactone that α who has a methyl, β one are unsaturated or saturated or have the lactone ring five membered of acetonyl, and the carbochain of being made up of 5～15 CH2 links together, usually have hydroxyl, ketone group, acetoxyl group replacement on the carbochain of tetrahydrofuran (THF) ring both sides, their chemical structure is as follows:
    Figure A9911724200023
    R 1=H, R 2The peaceful first of=OH Arnold (AnnoninI)
    R 1=OH, R 2=H Arnold is (AnnoninVI) rather
    Sweetsop Xi Ningjia (squamosinin A)
    Figure A9911724200031
    Neo-annoacin-10-one (neo-annoacin-10-one)
    Hainan GONIOTHALAMIN is heptan (howiicin FG)
  3. 3. according to claim 1 and the 2 described poly-acetyl genins of removing HIV viruses, treatment acquired immune deficiency syndrome (AIDS), it is characterized by monomeric compound, mixture or the plant extract that contains above-claimed cpd and separated part and compound preparation medicine that this medicine comprises above-claimed cpd.
CN 99117242 1999-11-24 1999-11-24 Polyacetyl acetogenins for eliminating HIV virus and treating AIDS Pending CN1255494A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004108128A1 (en) * 2003-06-05 2004-12-16 Peng Yang The use of bullatacin in manufacturing the medicaments of suppressing aids virus
CN111184032A (en) * 2020-01-10 2020-05-22 云南农业大学 Goniothalamus affinis nematode killing extract as well as preparation method and application thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004108128A1 (en) * 2003-06-05 2004-12-16 Peng Yang The use of bullatacin in manufacturing the medicaments of suppressing aids virus
CN111184032A (en) * 2020-01-10 2020-05-22 云南农业大学 Goniothalamus affinis nematode killing extract as well as preparation method and application thereof
CN111184032B (en) * 2020-01-10 2021-05-07 云南农业大学 Goniothalamus affinis nematode killing extract as well as preparation method and application thereof

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