CN102558277A - Synthesis method of titerpene saponin compound stryphnoside A - Google Patents

Synthesis method of titerpene saponin compound stryphnoside A Download PDF

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CN102558277A
CN102558277A CN2010106085217A CN201010608521A CN102558277A CN 102558277 A CN102558277 A CN 102558277A CN 2010106085217 A CN2010106085217 A CN 2010106085217A CN 201010608521 A CN201010608521 A CN 201010608521A CN 102558277 A CN102558277 A CN 102558277A
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stryphnoside
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杜宇国
吕迅
魏国华
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Research Center for Eco Environmental Sciences of CAS
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Abstract

The invention relates to a synthesis method of a titerpene saponin compound, belonging to the technical field of organic chemistry. Stryphnoside A molecule is synthesized by using a 'convergent' synthesis strategy and applying a multi-step selective coupling method, and shows remarkable biological activity on the aspects of cancer prevention, diabetes suppression and the like.

Description

The compound method of triterpene saponin compound stryphnoside A
Technical field
The present invention relates to a kind of compound method of natural triterpene saponin compound, belong to the technique of organic chemistry category.
Background technology
Saponin(e (saponins) claim saponin again, is glucosides (Glycoside) compound of one type of complicacy.See that from molecular structure saponin(e is linked to each other through carbon oxygen covalent linkage with triterpene, steroidal or tetrahydroisoquinoline alkaloid by sugar chain and forms.Sugar chain in the saponin(e is generally shorter, contain 2-5 glycosyl, but its structural changes is very many, and the free hydroxyl on the saponin(e sugar chain often has the base of modification simultaneously, so the variety of sugar chain structure has brought many difficulties for the saponin(e molecular studies in the saponin(e.
Recent two decades comes; People separate the saponin(e that has obtained millions of novel structures from natural phant; Many results of study show that saponin(e has multiple physiologically active and good pharmacological action; As anticancer, regulate immunologic function, prevent and treat cardiovascular disorder, hypotensive, antibiotic, anti-inflammatory, diuresis, antiviral etc., they still are the particularly activeconstituentss of herbal medicine of a lot of traditional medicinal plants.
The Akihito Yokosuka study group of Japan studies for a long period of time to each kind of plant of Brazil, has extracted the natural product of a lot of steroidal classes, and these saponin(es mostly have good biological activity.This study group has extracted the triterpenoid of 6 kinds of saponinses in the plant of a kind of Stryphnodendron of being called fissuratum recently, and the fruit of this kind of plant can cause ox sudden death disease, and stryphnoside A is exactly that wherein structure is comparatively simply a kind of.Pertinent literature proves that the saponins compound with similar structures generally has good biological activity, and based on this, we design and have synthesized stryphnoside A molecule, and it is anticancerly studied with the biological activity that suppresses aspect such as mellitus.
Summary of the invention
The objective of the invention is to utilize the synthesis strategy of " convergence type ", synthetic stryphnoside A molecule, and study it anticancer, the biological activity of aspects such as inhibition mellitus.
The present invention relates to a kind of compound method of natural triterpene saponin compound, belong to the technique of organic chemistry category.We utilize the synthesis strategy of " convergence type ", use multistep selectivity link coupled method, have synthesized stryphnoside A molecule, and for further studying it anticancer, the biological activity of aspects such as inhibition mellitus provides the raw material basis.The structural formula of stryphnoside A (1) is as follows:
Figure BSA00000401422600011
Below, in conjunction with instance the present invention is carried out detailed explanation.
1H NMR by Bruker ARX 400 at CDCl 3In record, be interior mark with tetramethylsilane.Mass spectrum adopts VG PLATFORM mass spectrograph, with ESI technology sample introduction.Thin-layer chromatography (TLC) is by HF 254Sulfuric acid methanol solution or ultraviolet (UV) detector with 30% (v/v) on the silica-gel plate detect.Column chromatography adopts 100-200 purpose silica gel, with ETHYLE ACETATE-sherwood oil (60-90 ℃) or ETHYLE ACETATE-methyl alcohol as leacheate, solution underpressure distillation the time less than 60 ℃, but below the compound that do not specify all be commercially available or the material for preparing of reference literature.
Embodiment 1:
Figure BSA00000401422600021
Under-60 ℃, compound 2 (2.4 grams, 10.0 mmoles) is dissolved in methylene dichloride (50 milliliters), and the adding zinc chloride (0.5 milliliter, 0.5 mmole; The diethyl ether solution of 1 mol), is reflected at-60 ℃ and stirred 30 minutes down, be warming up to 0 ℃, continue to stir 30 minutes, add the saturated sodium bicarbonate solution cancellation; Use dichloromethane extraction, merge organic phase, drying concentrates; Residuum is used the silica gel chromatography column purification, with petroleum ether-ethyl acetate drip washing in 2: 1, obtains white solid 3 (2.2g, 92%). 1H?NMR(400MHz，CDCl 3)：δ4.76(t，1H，J?9.1Hz，H-2)，δ4.40(d，1H，J?9.4Hz，H-1)，δ4.08(m，1H，H-4)，δ3.53-3.74(m，4H)，δ3.27(t，1H，J10.1Hz，H-3)，δ2.67(m，2H，SCH 2CH 3)，δ2.13(s，3H，Ac)，δ1.25(t，SCH 2CH 3).Anal.Calcd?forC 9H 16O 5S：C，47.75；H，6.83；Found：C，47.91；H，6.88.
Embodiment 2:
Figure BSA00000401422600022
Compound 3 (236 milligrams, 1.0 mmoles) is dissolved in the anhydrous methylene chloride (5mL), adds trimethylsilyl trifluoromethanesulfonate (TMSOTf successively under-15 ℃; 18 microlitres; 0.10 mmole), compound 4 (463 milligrams, 1.1 mmoles); Reaction mixture is stirring reaction after 1 hour with this understanding, with the triethylamine neutralization and concentrate.Crude product adds pyridine (5 milliliters), acetic anhydride (5 milliliters), and stirring at room is evaporate to dryness after 2 hours, and residuum is used the silica gel chromatography column purification, with petroleum ether-ethyl acetate drip washing in 2: 1, obtains white foam shape solid 5 (392 milligrams, productive rate 73%). 1H?NMR(400MHz，CDCl 3)：δ5.22(m，1H，H-4II)，δ5.20(t，1H，J8.8Hz)，δ5.02-5.04(m，2H)，δ4.92(t，1H，J?9.2Hz，H-2 I)，δ4.50(d，1H，J?5.0Hz，H-1 II)，δ4.47(d，1H，J?9.2Hz，H-1 I)，δ4.01(m，1H)，δ3.98(m，1H)，δ3.85(m，1H)，δ3.61(dd，1H，J?12.4，2.4Hz)，δ3.34(dd，1H，J?3.2，11.6Hz)，δ2.66(m，2H，SCH 2CH 3)，δ2.03-2.10(5s，15H，5×Ac)，δ1.26(t，SCH 2CH 3).Anal.Calcdfor?C 22H 32O 13S：C，49.25；H，6.01；Found：C，49.36；H，6.01.
Embodiment 3:
Under 0 ℃, with compound 6 (561 milligrams, 1.0 mmoles), N, (0.52 milliliter of N-diisopropyl ethyl amine; 3.0 mmole), be dissolved in methylene dichloride (30 milliliters), add chloromethyl ether (0.44 milliliter, 6.0 mmoles), reaction is 3 hours under the room temperature; Use extracted with diethyl ether, organic phase is washed with saturated sodium bicarbonate, and drying concentrates; Residuum is used the silica gel chromatography column separating purification, with petroleum ether-ethyl acetate drip washing in 30: 1, obtains syrup compound 7 (532mg, 88%). 1H?NMR(400MHz，CDCl 3)：δ7.30-7.35(m，5H，PhH)，δ5.28(t，1H，J3.5Hz，H-12)，δ5.07(dd，2H，12.5Hz，PHCH 2)，δ4.70(s，2H，CH 3OCH 2)，δ4.54(m，1H，H-2)，δ3.38(s，3H，CH 3OCH 2)，δ2.92(dd，1H，J3.8，4.3Hz，H-18)，δ0.60，0.89，0.90，0.92，1.10，1.20(7s，7×3H，7CH 3).Anal.Calcd?for?C 39H 56O 5：C，77.44；H，9.33；Found：C，77.54；H，9.52.
Embodiment 4:
Figure BSA00000401422600032
Under 0 ℃,, be dissolved in THF (20 milliliters) with compound 7 (605 milligrams, 1.0 mmoles); Ethanol (4 milliliters) adds Peng Qinghuana (45 milligrams, 1.2 mmoles), and 0 ℃ was reacted 12 hours down; Add the hydrochloric acid soln of 1 mol, organic phase is washed with saturated sodium bicarbonate, and drying concentrates; Residuum is used the silica gel chromatography column separating purification, with petroleum ether-ethyl acetate drip washing in 30: 1, obtains white solid 8 (498 milligrams, 82%). 1HNMR(400MHz，CDCl 3)：δ7.30-7.34(m，5H，PhH)，δ5.28(t，1H，J?3.5Hz，H-12)，δ5.07(dd，2H，12.5Hz，PHCH 2)，δ4.73(dd，2H，J?6.8Hz?CH 3OCH 2)，δ3.53(m，H-2)，δ3.40(s，3H，CH 3OCH 2)，δ3.07(d，1H，J9.4Hz，H-3)，δ2.92(dd，1H，J3.8，4.3Hz，H-18)，δ0.59，0.83，0.90，0.92，0.93，1.06，1.12(7s，7×3H，7CH 3).Anal.Calcd?for?C 39H 58O 5：C，77.19；H，9.63；Found：C，77.14；H，5.72.
Embodiment 5:
Figure BSA00000401422600041
Compound 8 (61 milligrams, 0.10 mmole) is dissolved in exsiccant methylene dichloride (5 milliliters), under-42 ℃, adds trimethylsilyl trifluoromethanesulfonate (TMSOTf successively; 0.9 microlitre, 0.050 mmole), (46 milligrams of compounds 9; 0.11 mmole), N-iodo succimide (37 milligrams, 0.16 mmole); Reaction mixture is stirring reaction after 1 hour with this understanding, with the triethylamine neutralization and concentrate.Residuum is used the silica gel chromatography column purification, with petroleum ether-ethyl acetate drip washing in 3: 1, obtains white foam shape solid 10 (81 milligrams, productive rate 78%). 1H?NMR(400MHz，CDCl 3)：δ7.20-7.36(m，20H，5×PhH)，δ5.29(t，1H，J?3.5Hz，H-12)，δ5.07(dd，2H，12.5Hz，PHCH 2)，δ4.81-4.95(m，4H，2×PHCH 2)，δ4.55-4.61(m，4H)，δ4.48(d，1H，7.2Hz，H-1 II)，δ3.68-3.77(m，3H)，δ3.56-3.61(m，3H)，δ3.45(m，H-2I)，δ3.30(s，3H，CH 3OCH 2)，δ3.24(d，1H，J9.5Hz，H-3)，δ2.92(dd，1H，J?3.8，4.3Hz，H-18)，δ2.54(d，1H，J?1.6Hz)，δ0.59，0.87，0.91，0.93，0.96，1.08，1.11(7s，7×3H，7CH 3).Anal.Calcd?for?C 66H 86O 10：C，76.27；H，8.34；Found：C，76.14；H，8.50.
Embodiment 6:
Figure BSA00000401422600042
With compound 10 (208 milligrams, 0.20 mmole), (129 milligrams of compounds 5; 0.24 mmole), N-iodo succimide (81 milligrams, 0.36 mmole); Be dissolved in exsiccant methylene dichloride (10 milliliters); Add down trimethylsilyl trifluoromethanesulfonate (2.2 microlitres, 0.012 mmole) reaction mixtures stirring reaction after 30 minutes with this understanding at-42 ℃, with the triethylamine neutralization and concentrate.Residuum is used the silica gel chromatography column purification, with petroleum ether-ethyl acetate drip washing in 2: 1, obtains white foam shape solid 11 (239 milligrams, productive rate 87%). 1H?NMR(400MHz，CDCl 3)：δ7.20-7.41(m，20H，5×PhH)，δ5.30(t，1H，J?3.5Hz，H-12I)，δ5.22(d，2H，1.5Hz)，δ5.00-5.13(m，6H)，δ4.79-4.91(m，4H)，δ4.74(d，1H，J?10.0Hz)，δ4.54-4.63(m，4H)，δ4.47(d，1H，J?3.2Hz)，δ4.41(d，1H，J?7.6Hz)，δ3.98(m，2H)，δ3.58-3.80(m，8H)，δ3.38(d，1H，J7.7Hz)，δ3.29(s，3H)，δ3.11(t，2H)，δ2.92(dd，1H，J3.8，4.3Hz)，δ2.66(m，2H，SCH 2CH 3)，δ2.04-2.12(5s，15H，5×Ac)，δ0.60，0.88，0.91，0.93，0.96，1.07，1.12(7s，7×3H，7CH 3).Anal.Calcd?for?C 86H 112O 23：C，68.23；H，7.46；Found：C，68.14；H，7.40.
Embodiment 7:
Figure BSA00000401422600051
Compound 11 (151 milligrams, 0.10 mmole) is dissolved in methyl alcohol (15 milliliters), and 0 ℃ adds tosic acid (76 milligrams, 0.40 mmole) down, and reaction was at room temperature stirred 4 hours, and the neutralization of adding triethylamine also concentrates.Crude product is dissolved in methylene dichloride (5 milliliters) and methyl alcohol (5 milliliters), adds palladium hydroxide/carbon (25 milligrams), and hydrogenation reaction is after 4 hours under normal pressure; Filtering and concentrating, residuum are used the silica gel chromatography column purification, with ETHYLE ACETATE drip washing; Obtain white foam shape solid 12 (101 milligrams, productive rate 91%). 1H?NMR(400MHz，CDCl 3)：δ7.22-7.38(m，20H，5×PhH)，δ5.26(t，1H，J3.5Hz，H-12I)，δ5.18(m，1H)，δ4.94-5.08(m，6H)，δ4.82-4.87(m，2H)，δ4.74(t，2H，J?11.2Hz)，δ4.52-4.57(m，2H)，δ4.42-4.45(m，2H)，δ4.28(d，1H，J7.8Hz)，δ3.87-3.95(m，2H)，δ3.70-3.80(m，3H)，δ3.54-3.64(m，5H)，δ3.47(m，1H)，δ3.11(t，1H，J?11.4Hz)，δ2.88(d，1H，J9.2Hz)，δ1.98-2.07(5s，15H，5×Ac)，δ0.57，0.85，0.86，0.88，0.91，1.05，1.07(7s，7×3H，7CH 3).MALDITOF-MS：calcd?forC 56H 84O 22：1468.7[M] +；found，1491.9[M+Na] +，11507.9[M+K] +.Anal.Calcd?for?C 84H 108O 22：C，568.64；H，7.41；Found：C，68.72；H，7.40.
Embodiment 8:
Compound 12 (11 milligrams, 0.01 mmole) is dissolved in methylene dichloride (5 milliliters), adds pyridine (1 milliliter) and acetic anhydride (1 milliliter); Stirring at room concentrated after 18 hours, and residuum is used the silica gel chromatography column purification, with ETHYLE ACETATE drip washing; Obtain white foam shape solid 13 (10 milligrams, productive rate 81%). 1H?NMR(400MHz，CDCl 3)：δ5.27(t，1H，J3.5Hz)，δ5.19(m，2H)，δ4.97-5.07(m，3H)，δ4.91(t，1H，J9.7Hz)，δ4.78(t，1H，J8.2Hz)，δ4.59(d，1H，J8.0Hz)，δ4.67(d，1H，J5.3Hz)，δ4.43(d，1H，J?7.7Hz)，δ4.10-4.18(m，2H)，δ3.92-3.98(m，2H)，δ3.72-3.87(m，4H)，δ3.57(dd，1H，J?10.3，2.0Hz)，δ3.23(t，1H，J?11.4Hz)，δ2.92(d，1H，J?9.2Hz)，δ2.80(dd，1H，J?10.1，3.5Hz)，δ1.98-2.06(m，24H，8×Ac)，δ0.74，0.87，0.89，0.92，0.97，1.05，1.11(7s，7×3H，7CH 3).MALDITOF-MS：calcd?for?C 62H 90O 25：1234.6[M] +；found，1257.6[M+Na] +.Anal.Calcdfor?C 62H 90O 25：C，60.28；H，7.34；Found：C，60.39；H，7.30.
Embodiment 9:
Figure BSA00000401422600061
Compound 13 (50 milligrams, 0.04 mmole) is dissolved in exsiccant methylene dichloride (5 milliliters), under-78 ℃, adds trimethylsilyl trifluoromethanesulfonate (TMSOTf successively; 4 microlitres; 0.02 mmole), compound 14 (21 milligrams, 0.048 mmole); Reaction mixture is stirring reaction after 10 minutes with this understanding, with the triethylamine neutralization and concentrate.Residuum is used the silica gel chromatography column purification, with petroleum ether-ethyl acetate drip washing in 1: 1, obtains white foam shape solid 15 (48 milligrams, productive rate 79%). 1H?NMR(400MHz，CDCl 3)：δ6.01(d，1H，J?1.8Hz)，δ5.32(br，1H)，δ5.27(dd，1H，J?3.3，10.2Hz)，δ5.19-5.21(m，3H)，δ5.12(t，1H，J?9.9Hz)，δ4.97-5.07(m，3H)，δ4.91(t，1H，J?9.8Hz)，δ4.78(t，1H，J?8.0Hz)，δ4.59(d，1H，J?7.9Hz)，δ4.46(d，1H，J?5.2Hz)，δ4.42(d，1H，J?7.7Hz)，δ4.12-4.16(m，2H)，δ3.92-3.97(m，2H)，δ3.74-3.82(m，4H)，δ3.59(dd，1H，J?10.3，2.4Hz)，δ3.23(t，1H，J?11.4Hz)，δ2.92(d，1H，J9.0Hz)，δ2.89(dd，1H，J?10.1，3.6Hz)，δ1.99-2.15(m，33H，11×Ac)，δ1.24(d，1H，J6.1Hz)，δ0.76，0.86，0.99，0.95，0.97，1.07，1.13(7s，7×3H，7CH 3).MALDITOF-MS：calcd?for?C 62H 90O 25：1506.7[M] +；found，1529.7[M+Na] +.Anal.Calcd?for?C 74H 106O 30：C，58.95；H，7.09；Found：C，?58.82；H，7.06.
Embodiment 10:
Figure BSA00000401422600071
Compound 15 (30 milligrams, 0.020 mmole) is dissolved in methyl alcohol (5 milliliters), methylene dichloride (5 milliliters); Regulate PH to 9-10 with the sodium methylate of 1 mol/methanol solution, after reaction half a hour, add the acidic resins neutralization; Concentrate, use purified, with water wash; Obtain white solid 1 (19 milligrams, productive rate 91%). 1H?NMR(400MHz，MeOD)：δ6.01(d，1H，J?1.8Hz)，δ5.29(br，1H)，δ4.60(d，1H，J7.6Hz)，δ4.39(d，1H，J?7.4Hz)，δ4.24(d，1H，J?6.9Hz)，δ3.21-3.88(m，21H)，δ2.98(d，1H，J?8.8Hz)，δ2.92(dd，1H，J?10.6，3.5Hz)，δ1.24(d，1H，J?6.1Hz)，δ0.80，0.90，0.93，0.97，1.02，1.12，1.18(7s，7×3H，7CH 3).MALDITOF-MS：calcd?for?C 62H 90O 25：1044.6[M] +；found，1067.9[M+Na] +.Anal.Calcd?for?C 52H 84O 21：C，59.75；H，8.10；Found：C，59.79；H，8.10.

Claims (9)

1. the present invention relates to a kind of compound method of natural triterpene saponin compound, belong to the technique of organic chemistry category.We utilize the synthesis strategy of " convergence type ", use multistep selectivity link coupled method, have synthesized stryphnoside A molecule, and it is anticancer, and aspects such as inhibition mellitus show significant biological activity.
2. method according to claim 1 is characterized in that, utilizes the synthesis strategy of " convergence type " to make up stryphnoside A molecule.
3. method according to claim 1 is characterized in that, stryphnoside A molecule, and it is anticancer to have a potential, suppresses aspect such as mellitus and shows significant biological activity.。
4. method according to claim 1 is characterized in that, stryphnoside A molecule complete synthesis first.
5. method according to claim 1 is characterized in that, the series of features midbody in the synthetic stryphnoside A molecular process.
6. method according to claim 1 is characterized in that, uses TMSOTf, BF in the coupling process 3Et 2Louis such as O and AgOTf acid as catalyst, consumption are the 0.001-2000 molar equivalent of reactant.
7. method according to claim 1 is characterized in that, temperature of reaction is between-100 ℃-100 ℃.
8. method according to claim 1 is characterized in that, the reaction times is between 1 minute-200 hours.
9. method according to claim 1 is characterized in that, all kinds of SOLVENTS of reaction usefulness comprises non-polar solvent and N such as methylene dichloride, toluene, N '-N isopolarity solvent.
CN2010106085217A 2010-12-17 2010-12-17 Synthesis method of titerpene saponin compound stryphnoside A Pending CN102558277A (en)

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Application publication date: 20120711