CN113480510A - 桃金娘果中间苯三酚衍生物的快速制备及应用 - Google Patents
桃金娘果中间苯三酚衍生物的快速制备及应用 Download PDFInfo
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Abstract
本发明涉及天然有机化学领域，提供了间苯三酚衍生物的快速制备及应用，特别涉及桃金娘果中间苯三酚衍生物的快速制备及应用。其特征在于：桃金娘果粉碎物乙醇提取、萃取后得到的正己烷部浸膏、乙酸乙酯部浸膏、正丁醇部浸膏、水部浸膏，通过一些手段检测确定间苯三酚富集的部位为正己烷部，正己烷部通过硅胶柱梯度洗脱，得到的组分经过检测确定间苯三酚富集的部位再进行分离，通过可以快速分离到间苯三酚衍生物，仅从一个间苯三酚富集的小组分中就分离到了7个间苯三酚衍生物。该发明首次发现了桃金娘果提取物含有间苯三酚衍生物且具有抗S.aureus(革兰氏阳性菌)的活性，为制备治疗MASA提供了新的安全植物和天然化合物，为制备抗MASA的药物或药物组合物提供有力的技术支持。该发明提供了快速制备、分离间苯三酚衍生物的方法，大大提高了分离的效率。
Description
技术领域
本发明涉及间苯三酚衍生物的快速制备及应用，特别涉及桃金娘果中间苯三酚衍生物的快速制备及应用。
背景技术
桃金娘科(Myrtaceae)桃金娘属(Rhodomyrtus)植物全世界约有18种，主要分布于亚洲热带地区及大洋洲，我国仅有桃金娘(Rhodomyrtus tomentosa(Ait)Hassk)1种。桃金娘喜欢湿润高温的气候环境，原产于亚洲南部和东南部，分布在印度、中国东部到南部、菲律宾、南部到马来西亚和苏拉威西岛。桃金娘在中国民间特别是南方地区常被用作中草药治疗或预防疾病。最早在唐代人们就发现其具有良好的药用价值，《本草纲目》中也有收录。公元1765年，清代赵学敏的著作《本草纲目拾遗》中记载：“粤志：草花之以娘名者，有桃金娘，丛生野间，似梅而末微锐，似桃而色倍，中茎纯紫，丝缀深黄如金粟，名金桃娘，八、九月实熟，青绀若牛乳状，产桂林，今广州亦多有之。粤歌云：携手南山阳，采花香满筐，外家爱留求子，郎爱桃金娘。花镜：金丝桃一名桃金娘，出桂林郡，花似桃而大，其色更，中茎纯紫，心吐黄须，铺散花外，俨似金丝，八、九月实熟。青绀若牛乳状，味甘，可入药用。如分种，当从根下劈开，仍以土复之，至来年移植便活。花行血。子味甘入脾，养血明目。”1975年版(第二版)《全国中草药汇编》中记载：“根：祛风活络，收敛止泻；用于急、慢性肠胃炎，胃痛，消化不良，肝炎，痢疾，风湿性关节炎，腰肌劳损，功能性子宫出血，脱肛；外用治烧烫伤。叶：收敛止泻，止血。用于急性胃肠炎，消化不良，痢疾，外用治外伤出血。果：补血，滋养，安胎。用于贫血，病后体虚，神经衰弱，耳鸣，遗精。”1999年，宋立人的著作《中华本草》中记载：“养血止血，涩肠固精。主血虚体弱，吐血，鼻衄，劳伤咳血，便血，崩漏，遗精，带下，痢疾，脱肛，烫伤，外伤出血。”越南的传统医学中也有相关药用记载，如未成熟的果实被用来治疗腹泻或痢疾，成熟的果实被用来刺激免疫系统等(佛罗里达搜寻数据库)。桃金娘被广泛种植在热带和亚热带地区，在中国和越南，它的果实被用来酿酒，也被制成果冻，或是加了糖浆的新鲜罐头，供人食用。这种果实也可以用来做馅饼、果酱。近年来，由于其花色美丽的外观，植株高矮合适，其应用范围正由药用植物向观赏植物扩展。此外，它还被证明是一种有希望的阻燃剂，用于喜马拉雅山脉的防火工段。
现代药理研究则表明：桃金娘具有抗菌、抗肿瘤、抗疟疾等多种药理活性。然而，其在2015年版的《中华人民共和国药典》中并未收录。这说明，桃金娘的中药、西药的研究价值与潜力很大，并且其中西药用价值还有待被开发。除此之外，桃金娘还具有广泛的应用价值。进一步的研究发现桃金娘的活性成分为间苯三酚类化合物。但桃金娘的果子中是否含有此类化合物，如何高效分离制备得到新的、具有相应药物活性的间苯三酚类衍生物，目前未见技术报道。
发明内容
本发明的目的是提供桃金娘果中间苯三酚衍生物的快速制备及应用。
本发明的目的是提供桃金娘果中间苯三酚衍生物的快速制备及应用是通过以下的技术方案实现的：
间苯三酚衍生物，指的是具有通式Ⅰ骨架的化合物如所示：
如上述间苯三酚衍生物的快速制备方法为：
桃金娘果粉碎物经乙醇浸泡四次，浓缩得乙醇浸膏。然后用正己烷、乙酸乙酯、正丁醇各萃取三次，得到正己烷部浸膏、乙酸乙酯部浸膏、正丁醇部浸膏、水部浸膏。
经活性检测可知石油醚部浸膏抗S.aureus(革兰氏阳性菌)的活性较好，可知石油醚部中含有间苯三酚多于乙酸乙酯部、正丁醇部、水部，因此选取石油醚部进行接下来的实验。
进一步地，已知绝大多数间苯三酚衍生物的抗S.aureus(革兰氏阳性菌)的活性较好，因此重点关注S.aureus(革兰氏阳性菌)的活性，将它作为粗提物中间苯三酚衍生物含量的一个指标。
取将正己烷部浸膏过用正相硅胶柱正己烷：乙酸乙酯(100：0-0：100)，乙酸乙酯：甲醇(20：1-0： 100)梯度洗脱得Fr.A-Fr.K共11个组分。
进一步地，合并的时候，重点关注紫外，合并紫外和TLC显色相同的组分。
进一步地，薄层色谱(TLC)鉴定方法为：紫外灯254nm下观察，有明显的紫外，显色剂采用浓硫酸- 香草醛，浸润后于120℃吹风机加热直至出现斑点，还原的斑点为红色的为间苯三酚衍生物。
将Fr.A-Fr.K11个组分经活性检测，可知Fr.D、Fr.E、Fr.F、Fr.G的抗S.aureus(革兰氏阳性菌)活性可达到nm级别，因此优先做这几个部位。
Fr.D、Fr.E、Fr.F、Fr.G，综合运用正相硅胶色谱、反相硅胶色谱、凝胶色谱、HPLC等分离手段，结合薄层色谱(TLC)鉴定，分离单体化合物，分离出的单体化合物通过质谱、紫外光谱、红外光谱、核磁共振等对单体化合物的结构进行分析和鉴定。
仅从Fr.E组分中得到如下化合物：
本发明桃金娘果中间苯三酚衍生物的快速制备及应用。相对于现有技术，桃金娘果中间苯三酚衍生物的快速制备及应用，具有显著的优势：
本发明首次发现桃金娘果及其提取物可以用作天然的抗S.aureus(革兰氏阳性菌)的活性，且正己烷部粗提物活性最高，其抗S.aureus(革兰氏阳性菌)的主要成分是间苯三酚衍生物。
本发明提供了一种快速定位间苯三酚衍生物的方法，传统的通过分辨TLC紫外吸收情况和浓硫酸香草醛显色情况粗略检测有间苯三酚衍生物结构，如果含有杂质太多，通过简单的TLC根本发现不了间苯三酚衍生物的存在；如果将粗提物直接通过HPLC检测，样品所含杂质太多会将HPLC柱子堵塞，并且植物粗提物的杂质相对于间苯三酚衍生物的含量较多，少量样品可能检测不到间苯三酚衍生物的存在，并且粗提物成分复杂，仅通过紫外和保留时间很难判断是否为间苯三酚衍生物。
本发明采用抗S.aureus(革兰氏阳性菌)活性作为指标，通过分辨TLC紫外吸收情况和浓硫酸香草醛显色情况，定位更加直观、明确，在提取过程中大大加快了提取、分离速度。
本发明可以应用于其他植物间苯三酚衍生物科学研究工作，加速科学研究间苯三酚衍生物；本发明的快速制备方法可以应用于工业生产中，有助于企业获得纯度较高、活性较好的间苯三酚衍生物抗菌提取物，大大加快了工业生产的进度；鉴于间苯三酚衍生物广泛的生物活性，抗菌、抗肿瘤、抗病毒、抗炎、抗疟、抗胃溃疡、抗氧化、抗风湿、抗紫外线及护肤、牛皮癣、降糖、抗神经炎、促成骨细胞分化等，本发明也可广泛应用于各个制备领域。
附图说明
图1为Rhodomyrtone的结构式；
图2为Rhodomyrtone的1H-NMR的图；
图3为Rhodomyrtone的1C-NMR的图；
图4为Tomentodione C的结构式；
图5为Tomentodione C的1H-NMR的图；
图6为Tomentodione C的1C-NMR的图；
图7为Tomentodione B的结构式；
图8为Tomentodione B的1H-NMR的图；
图9为Tomentodione B的1C-NMR的图；
图10为Calliviminone E的结构式；
图11为Calliviminone E的1H-NMR的图；
图12为Calliviminone E的1C-NMR图；
图13为8a-hydroxy-3,3,6,6,8,8-hexamethyl-8,8a-dihydrobenzo[c][1,2]dioxine-5,7(3H,6H)-dione的结构式；
图14为8a-hydroxy-3,3,6,6,8,8-hexamethyl-8,8a-dihydrobenzo[c][1,2]dioxine-5,7(3H,6H)-dion的1H-NMR 的图；
图15为8a-hydroxy-3,3,6,6,8,8-hexamethyl-8,8a-dihydrobenzo[c][1,2]dioxine-5,7(3H,6H)-dion的1C-NMR 的图；
图16为Callistenone B的结构式；
图17为Callistenone B的1H-NMR的图；
图18为Callistenone B的1C-NMR的图；
图19为Isomyrtucommulone B的结构式；
图20为Isomyrtucommulone B的1H-NMR的图；
图21为Isomyrtucommulone B的1C-NMR的图；
具体实施方式
以下结合较佳的实施例，对依据本发明提出的桃金娘果中间苯三酚衍生物的快速制备及应用作详细介绍。
实施例1我们在中国江西省赣州市采得桃金娘的果实(湿)100kg左右，用小型烘干机烘干后放在太阳光下反复晾晒三天，得桃金娘干果35kg，用小型粉碎机粉碎得粗粉，后用95％的乙醇(75L)提取四次，前三次12h，最后一次24h，将提取液用旋转蒸发仪旋干的总浸膏约3kg。接着分别用石油醚、乙酸乙酯、正丁醇萃取得石油醚部浸膏(441.6g)、乙酸乙酯部浸膏、正丁醇浸膏、水部浸膏。
试验例：桃金娘果的提取的总粗提物、石油醚部、乙酸乙酯部、正丁醇部、水部的体外抗菌活性。
阳性对照药品：卡那霉素(Kanamycin)、万古霉素(Vancomycin)。
阴性对照药品：空白、DMSO
指示剂：刃天青(Sigma)。
供试菌株：S.aureus(CMCC 26003)、E.coli(ATCC 8739)购于广东微生物所。
培养基：MH(水解酪蛋白胨)培养基
实验试剂：DMSO、超纯水(美国MILLIPORE公司)、琼脂。
实验仪器：分析天平(德国SARTORIUS公司)、超净工作台(上海智城分析仪器制造有限公司)、压力蒸汽灭菌锅(上海三申医疗器械有限公司)、恒温培养箱(日本SANYO公司)、恒温振荡培养箱(上海一恒科技有限公司)、普通冰箱(青岛海尔电器有限公司)、紫外可见分光光度计(上海元析仪器有限公司)、 96孔细胞培养板(美国CORNING公司)等。
实验方法：本实验采用刃天青显色法来测定化合物的抑菌能力，用最低抑菌浓度值(MIC)来反应化合物的抑菌效果。刃天青是一种蓝色非荧光氧化还原指示剂，活细胞中的各种还原酶能够使刃天青指示剂从蓝色变为粉红色，但是无活性的细胞因其无代谢能力而不能还原，通过观察菌液颜色的变化来测定化合物的抗菌能力。将指示剂、化合物与菌液共培养一定时间后，若菌液变为红色则表明化合物没有抑菌活性，维持蓝色则具有抑菌活性。
实验步骤：复苏菌种：将已冻存的各种菌种分别涂布于MHB固体培养基，放于37℃恒温培养箱中过夜培养。
供试菌液的培养：挑选单个菌落接种于MHB液体培养基中，然后置于37℃恒温振荡培养箱中培养12 小时。将繁殖生长的菌株用MHB培养基稀释，用紫外分光光度计调节OD600值至0.07左右，得到1.25+106 CFU/mL的菌液。梯度稀释法：首先将刃天青指示剂与纯化水溶液按比例混合至浓度为100μg/mL，将配制好的刃天青溶液与待测菌液以1.5：1的比例混匀，化合物用DMSO配制浓度为500mg/mL，第一排加入180μL 的混匀物和20μL的化合物，剩余每排加入100μL，然后按梯度稀释。最后将96孔板置于37℃恒温培养箱中培养10～12小时，观察颜色变化。
粗提物抗革兰氏阳性菌和革兰氏阴性菌的结果：
再选取对石油醚部浸膏进行分离。将石油醚部浸膏过用正相硅胶柱正己烷：乙酸乙酯(100：0-0：100)，乙酸乙酯：甲醇(20：1-0：100)梯度洗脱得Fr.A-K11个组分。
试验例：桃金娘果的分离的石油醚部组分Fr.A、Fr.B、Fr.C、Fr.D、Fr.E、Fr.F、Fr.G、Fr.H、Fr.I、Fr.J、Fr.K的体外抗菌活性。
阳性对照药品：卡那霉素(Kanamycin)、万古霉素(Vancomycin)。
实验方法依然采用刃天青显色法来测定化合物的抑菌能力。
Fr.A-K抗革兰氏阳性菌和革兰氏阴性菌的结果
Fr.A再用TLC薄层色谱、香草硫酸醛显色检测可知大部分为脂肪链。、Fr.B、Fr.C再经过TLC薄层色谱、香草硫酸醛显色检测可知大部分为脂肪酸。
仅挑选一个活性中等的Fr.E组分分离就得到了如下间苯三酚衍生物：
Rhodomyrtone，其化学结构如图1所示；分子式：C26H34O6。如图2所示，核磁1H NMR(CD3Cl3,500 MHz):δH 6.15(1H,s,H-5),4.30(1H,s,9-H),3.01(2H,m,J＝3Hz,H-2'),2.30(1H,m,J＝2.30Hz,H-3'),1.57 (3H,s,4-CH3),1.46(3H,s,4-CH3),1.43(3H,s,2-CH3),1.40(3H,s,2-CH3),0.90(6H,d,J＝1.01Hz,H-3,H-4'), 0.85(6H,dd,J＝0.9Hz,H-3",H-4")；如图3所示，13C-NMR(CD3Cl3,125MHz):δC 212.09(C-3),206.53 (C-1'),198.11(C-1),167.31(C-4a),162.63(C-8),158.58(C-6),155.66(C-10a),114.27(C-9a),107.69(C-7),106.53 (C-8a),94.85(C-5),56.05(C-2),53.19(C-2'),47.22(C-4),45.83(C-1"),25.24(C-9),25.19(C-2"),25.14(C-4), 24.74(C-4),24.60(C-2),24.17(C-2),23.52(C-2"),23.19(C-3'),22.81(C-3'),22.75(C-2").
Tomentodione C，其化学结构如图4所示；分子式：C26H34O6。如图5所示，1H NMR(CD3Cl3,500MHz): δH 1.54(1H,m,H-1),1.44(2H,m,H-2),2.03(2H,dd,J＝15.5,10.0Hz,H-3a),2.11(1H,m,H-5),1.72(2H,m, H-6),2.38(2H,m,H-7),2.59(1H,dd,J＝18.0,9.0Hz,H-9),1.73(2H,m,H-10),0.90(3H,s,H-12),0.99(3H,s, H-13),1.26(1H,s,H-14),4.85(2H,br,s,H-15),2.99(3H,ddd,J＝8.0,5.0,2.5Hz,H-7'),1.49(1H,m,H-8'a),1.08 (2H,ddd,H-8'b),1.67(3H,m,9'),0.97(3H,d,J＝6.5Hz,10'),0.90(1H,d,J＝6.6Hz,11'),0.90(2H,s,12'),1.38 (1H,s,13'),1.36(3H,s,14'),1.35(3H,s,15').如图6所示，13C-NMR(CD3Cl3,125MHz):δC 213.86(C-3'), 197.90(C-5'),169.40(C-1'),154.56(C-8),114.66(C-6'),109.75(C-15),85.43(C-4),56.94(C-1),55.38(C-4'),47.81 (C-2'),42.75(C-9),41.96(C-8'),41.47(C-3),38.52(C-5),38.37(C-10),36.24(C-7),33.35(C-11),29.50(C-12), 29.18(C-7'),27.45(C-9'),26.08(C-13'),25.34(C-12'),25.02(C-15'),24.15(C-10'),23.59(C-14),23.28(C-2),22.80 (C-14'),22.13(C-13'),21.81(C-11').
Tomentodione B，其化学结构如图7所示；分子式：C26H34O6。如图8所示，1H NMR(CD3Cl3,500MHz): δH 1.50(1H,m,H-1),1.56(2H,m,H-2),2.02(2H,dd,J＝15.5,10.0Hz,H-3a),1.74(1H,m,H-5),1.67(2H,m, H-6),2.34(2H,m,H-7),2.40(1H,dd,J＝18.0,9.0Hz,H-9),1.74(2H,m,H-10),0.95(3H,s,H-12),0.98(3H,s, H-13),1.34(1H,s,H-14),4.92(2H,br,s,H-15),2.89(3H,ddd,J＝8.0,5.0,2.5Hz,H-7'),1.41(1H,m,H-8'a),1.08 (2H,ddd,H-8'b),1.48(3H,m,9'),0.84(3H,d,J＝6.5Hz,10'),0.98(1H,d,J＝6.6Hz,11'),1.33(2H,s,12'),1.36 (1H,s,13'),1.34(3H,s,14'),1.35(3H,s,15')；如图9所示，13C-NMR(CD3Cl3,125MHz):δC 213.83(C-3'), 197.15(C-5'),170.28(C-1'),150.79(C-8),116.39(C-6'),111.00(C-15),86.33(C-4),58.09(C-1),55.44(C-4'),47.62 (C-2'),46.21(C-9),42.30(C-8'),40.90(C-3),39.77(C-5),36.14(C-10),35.35(C-7),34.41(C-11),29.74(C-12), 28.35(C-7'),26.59(C-9'),25.44(C-13'),25.38(C-12'),25.27(C-15'),24.89(C-15'),24.63(C-10'),24.13(C-14), 23.75(C-2),23.36(C-14'),21.78(C-13'),21.60(C-11').
Calliviminone E，其化学结构如图10所示；分子式：C25H38O3。如图11所示，1H NMR(CD3Cl3,500MHz): δH 2.30(m,H-7),1.32(m,H-8),0.71(m,H-8),1.58(m,H-9),0.86(d,J＝7.0Hz,H-10),0.88(d,J＝7.0Hz,H-11), 1.40(s,H-12),1.37(s,H-13),1.40(s,H-14),1.36(s,H-15),2.49(dd,J＝17.5,1.5Hz,H-1'),2.16(m,H-1'),5.33(br s,H-2'),2.14(m,H-4'),2.02(m,H-6'),1.94(m,H-6'),2.04(m,H-6'),5.06(t,J＝7.0Hz,H-7'),1.62(s,H-9'),1.59 (s,H-10').如图12所示，13C-NMR(CD3Cl3,125MHz):δC 212.9(C-3),208.15(C-1),208.15(C-2),136.37(C-3'), 131.58(C-8'),123.93(C-7'),115.94(C-2'),67.59(C-6),56.51(C-9),56.19(C-4),39.02(C-8),37.14(C-5'),33.90 (C-7),30.54(4'),29.31(C-1'),26.31(C-6'),26.13(C-15),25.93(C-12),25.71(9'),25.40(C-6),24.93(C-14),24.34 (C-10),24.27(C-13),20.90(C-11),17.74(10').
8a-hydroxy-3,3,6,6,8,8-hexamethyl-8,8a-dihydrobenzo[c][1,2]dioxine-5,7(3H,6H)-dione，其化学结构如图 13所示；分子式:C14H20O5。如图14所示，1H NMR(CD3Cl3,500MHz):δH1.07(3H,s,8a-CH3),1.35(3H,s, 8b-CH3),1.38(3H,s,3a-CH3),1.39(6H,s,6-CH3),1.52((3H,s,3b-CH3),7.17(1H,s,H-4).如图15所示， 13C-NMR(CD3Cl3,125MHz):δC210.65(C-5,7),198.36(C-5,7),143.05(C-4),131.66(C-4a),97.38(C-8a), 79.09(C-3),54.97(C-8,6),51.65(C-8,6),26.60(-CH3),24.07(-CH3),23.90(-CH3),23.67-CH3),20.93(-CH3), 15.17(-CH3).
Callistenone B，其化学结构如图16所示；分子式：C25H32O6。如图17所示，1H NMR(CD3Cl3,500MHz): δH 6.31(1H,s,H-7),4.29(1H,d,J＝4.3Hz,H-9),1.39(3H,s,H-10),1.33(3H,s,H-11),1.68(3H,s,H-12),1.50 (3H,s,H-13),3.27(1H,dd,J＝13.8,6.6Hz,H-2'),3.01(1H,dd,J＝13.8,6.6Hz,H-2'),2.30-2.38(1H,m,J＝4.3 Hz,H-3'),1.02(3H,d,J＝6.6Hz,H-4'),0.99(3H,d,J＝6.6Hz,H-5'),1.89-1.99(1H,m,H-1"),0.82(3H,d,J＝6.9Hz,H-2"),0.79(3H,d,J＝6.9Hz,H-3").如图18所示，13C-NMR(CD3Cl3,125MHz):δC211.83(C-3), 204.09(C-1'),198.35(C-1),168.04(C-4a),164.33(C-6),159.36(C-8),153.75(C-4b),112.27(C-9a),105.70(C-5), 103.77(C-8a),100.53(C-7),56.15(C-2),53.43(C-2'),47.47(C-4),34.79(C-1"),31.55(C-9),25.29(C-12),25.14 (C-13),24.91(C-3'),24.74(C-10),24.14(C-11),22.85(C-4'),22.68(C-5'),18.90(C-2"),18.74(C-3").
Isomyrtucommulone B，其化学结构如图19所示；分子式：C25H32O6。如图20所示，1HNMR(CD3Cl3, 500MHz):δH 6.14(1H,s,H-5),4.33(1H,d,J＝4.3Hz,H-9),3.92(1H,m,J＝6.6Hz,H-2'),2.01(1H,m,J＝3.5 Hz,H-1"),1.39(3H,s,2-CH3),1.42(3H,s,2-CH3),1.44(3H,s,4-CH3),1.48(3H,s,4-CH3),1.23(3H,d,J＝6.6 Hz,2'-CH3),1.21(3H,d,J＝6.6Hz,2'-CH3),0.80(6H,t,J＝7.2Hz,1"-CH3).如图21所示，13C-NMR(CD3Cl3, 125MHz):δC197.67(C-1),56.16(C-2),212.15(C-3),47.34(C-4),167.93(C-4a),95.07(C-5),156.41(C-10a), 106.93(C-7),162.15(C-8),105.01(C-9),111.79(C-9a),156.4(C-10a),211.02(C-1'),39.8(C-2'),34.52(C-1"), 31.94(2-CH3),25.12(C),24.57(4-CH3),23.94(),19.26(2'-CH3),19.09(C-),18.79(1"-CH3).
Claims (6)
1.桃金娘果中间苯三酚衍生物的快速制备及应用，其特征在于：快速制备桃金娘果中的间苯三酚衍生物，及其应用。
2.根据权利要求1所述的间苯三酚衍生物，其特征在于：具有式Ⅰ所示的基本骨架结构：
3.根据权利要求1所述的快速制备，其特征在于：在提取、萃取完之后，采用活性测试方法定位间苯三酚衍生物的部位。
4.根据权利要求3所述的活性测试方法，其特征在于：检测抗S.aureus的活性。
5.根据权利要求1所述的快速制备，其特征在于：在分离过程中，重点关注有紫外，TLC显色呈红色的化合物。
6.根据权利要求1所述应用，其特征在于主要应用于抗菌领域。
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