CN108601847A - 天然防腐剂和抗微生物剂,包括其组合物 - Google Patents
天然防腐剂和抗微生物剂,包括其组合物 Download PDFInfo
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- CN108601847A CN108601847A CN201680078387.XA CN201680078387A CN108601847A CN 108601847 A CN108601847 A CN 108601847A CN 201680078387 A CN201680078387 A CN 201680078387A CN 108601847 A CN108601847 A CN 108601847A
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- magnolia
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- albizia
- extract
- albizzia
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Abstract
本文公开了包含至少一种合欢属(Albizia)提取物和木兰属(Magnolia)提取物的混合物的组合物。在一些实施方案中,所述组合物包含至少一种富集一种或多种大环生物碱的合欢属提取物和至少一种富集一种或多种木脂素的木兰属提取物的混合物。
Description
该美国PCT申请要求2015年11月9日提交且题目为“天然防腐剂和抗微生物剂”的美国临时专利申请序列号:62252987,和2016年11月7日提交且题目为“天然防腐剂和抗微生物剂,包括其组合物”的美国发明申请序列号:15/345,006的优先权,其全部内容通过引用共同拥有且并入本文。
主题领域
本主题的领域涉及可用作防腐剂、抗微生物剂,或其组合的组合物及相关的方法。预期的实施方案涉及从源自苦味合欢(Albizia amara)种子和厚朴(Magnolia officinalis)树皮的提取物衍生的防腐剂,其可用来保存食品、化妆品、保健品、口腔卫生产品和药品。
背景
防腐剂是一种加入到产品,例如食品、药品、化妆品、生物样品等中,以防止由微生物生长或由不良化学变化所致分解的物质。抗-微生物防腐剂防止由细菌所致的降解,并抑制细菌、真菌和其它微生物的生长以保持产品质量并延长保质期。防腐剂可原样使用或它可与其它用于保存的物理技术包括脱水、UV-C辐射、冷冻干燥、冷藏等组合。抗-氧化剂防腐剂通常用于食品工业,特别是具有高脂肪含量的食品。普通的抗-氧化剂包括苯酚衍生物BHT(丁羟甲苯)和BHA (丁羟茴醚)。其它防腐剂包括甲醛、戊二醛、乙醇和甲基氯异噻唑啉酮。
化学防腐剂和物理保存通常结合。普通抗-微生物防腐剂包括针对不同产品的硝酸钠、亚硝酸钠、亚硫酸盐(二氧化硫、亚硫酸氢钠和亚硫酸氢钾)、苯甲酸/苯甲酸钠、山梨酸/山梨酸钠、丙酸/丙酸钙/丙酸钠,和EDTA二钠。许多合成的防腐剂的功效、安全性和毒性是在学术界和监管机构的详细审查下,因为来自用户的负面报道和关注,例如对羟基苯甲酸酯及其类似物,其已在欧洲以及一些亚洲国家中被禁止。天然防腐剂被认为是用于微生物感染的更安全且更环保的替代品,具有广泛范围的结构多样化的生物活性化合物,例如生物碱、类黄酮、芳香萜类和皂苷。
天然物质例如盐、糖、醋、茶提取物、草本植物精油和有机酸作为传统防腐剂是完全可接受的。例如,来自柠檬或其它柑桔汁的柠檬酸和抗坏血酸通常在水果和果汁行业中用作抗-褐变和抗-氧化剂以改进食品质量。然而,与合成的防腐剂,特别是抗微生物防腐剂比较,目前的天然防腐剂可能是昂贵的或具有不太有效的功效,这限制了它们在食品、化妆品和其它生物产品行业中的广泛应用。有效的、有针对性的和适当的防腐剂对于延长产品保质期、保持产品质量、在整个过程和运输中在很多方面获益以改进产品安全性都是至关重要的。因此,发现和利用一种具有有效针对广谱微生物的抗微生物活性的特殊天然组合物的想法是实际的和吸引人的。
因此,对替代天然防腐剂和抗微生物剂存在需求。为开发天然防腐剂,进行了一种高通量抗-大肠杆菌(E. coli)测定以筛选超过10,216种有机提取物(OE)和水性提取物(AE)的植物库,其从世界各地收集的药用植物生成,苦味合欢(Albizia amara)种子提取物被鉴定为最佳先导,表现出具有40 ug/mL的MIC值的有效抗-革兰氏阴性抑制作用。生物测定-指导的分离和鉴定确认活性成分是如在图1中所示的布木柴胺C (budmunchimaine C),及其类似物。
合欢属(Albizia)是主要在亚洲、非洲、马达加斯加、美洲和澳洲的亚热带和热带地区,但主要是在旧世界热带地区分布的约超过150个物种的属。许多种类已在印度和南部非洲国家用作感冒、腹泻、头痛、肠道疾病、胃癌、喉咙痛和胃痛的民间药物。例如A.schimperiana的茎皮在当地被用于治疗细菌和寄生虫感染,且更通常用于针对发热和缓解疼痛。
这些植物的现代研究显示抗微生物、抗寄生虫、抗锥体虫和杀灭蚊虫幼虫的活性。这些合欢属植物的进一步的研究导致独特类型的、由布木柴胺A-I和其它类似物代表的大环生物碱的发现(Dixit 1995; Assis 1999; Misra, 1995; Ovenden 2002; Samoylenko2009)。已经报道了来自苦味合欢(Albizia amara)、阔荚合欢(Albizzia lebbek)的种子,含胶合欢(Albizzia gummifera)、Albizia schimperana、雨树(Albizia saman/Samaneasaman)、Albizia schimperiana、Albizia adinocephala的茎皮或树皮,Albizziainopinata、雨树(Pithecolobium saman=Albizia saman)的树叶的、具有各种抗-微生物、抗-寄生虫和抗癌活性的这种特征性类型的大环生物碱(Samoylenko 2009; Geyid 2005;Thippeswamy 2015; Mar 1991; Pezzutoa 1992)。
图1. 布木柴胺C的化学结构
厚朴,通常在中国称为“厚朴(houpu)”,是具有非常广泛应用的中医药的普通成分之一,是木兰属(Magnolia)的中国本土物种,主要生长于四川和湖北省。厚朴指的是其厚的树皮,其可从茎、枝条和根剥离。传统适应症是治疗中风、冻伤、头痛、对抗气滞和血瘀。木兰属树皮已被用来治疗痛经、腹痛、腹胀和气胀、恶心和消化不良。树皮也是一种用于治疗咳嗽和哮喘的配方中的成分。含有木兰属树皮的许多制剂被用于治疗肺病例如包括咳嗽和哮喘或肠道感染和痉挛,缓解各种原因的腹部肿胀和水肿。
现代的研究发现了这种草药对抗各种微生物的有效的抗微生物和抗真菌活性,而双酚木脂素被鉴定为担负抗微生物效果的主要活性成分。厚朴酚(Magnolol)以及和厚朴酚(honokiol),如在图2中所示的,是木兰属树皮中发现的两个主要的多酚化合物并被报道具有不同的药理学活性和功能,例如抗氧化剂、抗-炎症,和抗肿瘤(Park 2004)。和厚朴酚的抗癌研究已扩大到几种不同的实体瘤类型例如乳腺、前列腺、胃,和卵巢癌,具有提高现有的抗癌治疗方案的潜力(Fried 2009)。和厚朴酚也减轻炎症和氧化应激,提供在神经保护和葡萄糖调节方面的有益作用,具有巨大潜力作为炎性疾病的治疗剂。特别是,已知厚朴酚及和厚朴酚表现出针对革兰氏阳性和革兰氏阴性细菌以及真菌,例如丙酸杆菌(Propionibacterium sp.)和金黄色葡萄球菌(S. aureus)的有效抗微生物活性,显示出其作为有效对抗更多的感染耐药性微生物的抗微生物剂的潜力(Ho 2001; Bang 2000; Kim2015)。和厚朴酚及厚朴酚在市售的木兰属树皮提取物中的含量可在1至99%之间变化。
图2. 厚朴酚及和厚朴酚的化学结构
有许多参考文献有助于提供关于为什么这些成分的一些可被认为是重要的背景。US8329095公开了用于化妆品制剂的包含从厚朴的超临界流体提取物获得的百里酚、单月桂酸甘油酯及厚朴酚的防腐剂组合物。US 7592025公开了用于包含与表面活性剂组合的木兰属树皮提取物的口腔护理的媒介和方法。
CN 101516364公开了包含羟基酪醇和/或橄榄苦苷和至少一种额外组分的组合物,所述额外组分选自额外组分如藁本内酯、橄榄苦苷苷元、厚朴酚,和Park苯酚、染料木黄酮、白藜芦醇、EGCG、木兰属树皮提取物、腰果果实提取物和Glycyrrhiza foetida,预期的实施方案也涉及作为药物组合物,尤其是作为用于治疗病症,治疗或预防炎症的药物组合物的用途。
CN 1103756公开了通过混合90-99.7%的厚朴(official magnolia)树皮的提取粉末及其余的大黄提取粉末制得的天然防腐剂。
CN 100544597公开了厚朴(magnolia)、铁线莲、葎草、藿香作为原料(根据每味中草药的不同特性)的中草药防腐剂。
CN 103416480公开了用于植物来源的复合橙防腐剂(complex Orangepreservatives):植物提取物、食品防腐剂、稳定剂和酸度调节剂复合材料的方法。主要的技术特征:主要成分含有防腐剂厚朴(magnolia)提取物10-15%、20-30%丁香提取物、山梨酸钾10-20%、10-20%对羟基苯甲酸丙酯、2-5%柠檬酸、1-5%稳定剂,其性状为褐色乳液。
WO 2006069209公开了提供一种有效的抗菌和抗-炎性口腔组合物,其具有包含一种或多种来自木兰属(magnolia)的提取物和蛇麻草(hop)的提取物的活性化合物的活性成分组合。
WO 2014131191公开了包含抗微生物活性的和厚朴酚和/或厚朴酚和羧酸的组合物。也提供其使用方法。然而,这些参考文献没有一个解决了本领域对用作防腐剂、抗微生物剂或其组合的组合物的需求。
本公开内容的简述
本文公开了包含至少一种合欢属(Albizia)提取物和木兰属(Magnolia)提取物的混合物的组合物。在一些实施方案中,所述组合物包含至少一种富集一种或多种大环生物碱的合欢属提取物和至少一种富集一种或多种木脂素(lignan)的木兰属提取物的混合物。
附图简述
图1. 布木柴胺C的化学结构
图2. 厚朴酚及和厚朴酚的化学结构
图3. 1 mg/mL的416-145-50的菌落计数
图4. 500 ug/mL的416-145-50的菌落计数
图5. 在0.5%离子o/w乳液系统中对1940601的菌落计数
图6. 在0.1%离子o/w乳液系统中对1940602的菌落计数
详细描述
简言之,本公开内容和预期的实施方案涉及可用作防腐剂和抗-微生物剂的化合物和组合物,包括所公开化合物的立体异构体、药学上或保健上可接受的盐、互变异构体、糖苷和前药,并涉及相关的方法。预期的实施方案涉及从源自苦味合欢(Albizia amara)种子和厚朴树皮的提取物衍生的防腐剂,其可用来保存食品、化妆品、保健品、口腔卫生产品和药品。
预期的化合物和组合物源自或包含至少一种植物提取物,其中植物提取物可能是或可能不是富集的。作为这种开发的一部分,经常利用可接受的测定来测试预期的化合物和组合物。
特别地,公开了用于防腐剂和抗微生物组合物的组合物、化合物和方法,其包含植物提取物的混合物,其中植物提取物包含至少一种苦味合欢(Albizia amara)种子和至少一种厚朴树皮。
一个预期的实施方案包括防腐剂混合物或组合物,其包含至少一种合欢属提取物和至少一种木兰属提取物的混合物。另一个预期的实施方案包括包含至少一种富集一种或多种大环生物碱的合欢属提取物和至少一种富集一种或多种木脂素的木兰属提取物的混合物的组合物。在预期的实施方案中,组合物被认为是防腐剂、抗微生物剂或其组合。
一些预期的实施方案包括至少一种来自植物材料或其它来源的合欢属提取物和至少一种来自植物材料或另一种来源的木兰属提取物的混合物,其中至少一种合欢属提取物与植物材料或另一种来源的至少一种合欢属提取物中的一种或多种大环生物碱的量或活性比较,具有一种或多种大环生物碱的量或活性的增加,且其中至少一种木兰属提取物与植物材料或另一种来源的至少一种木兰属提取物中的一种或多种木脂素的量或活性比较,具有一种或多种木脂素的量或活性的增加。
在一些实施方案中,至少一种合欢属提取物和至少一种木兰属提取物以范围从约10:1至1:10的重量比共混。在其它实施方案中,至少一种合欢属提取物和至少一种木兰属提取物以约1:1的重量比共混。可利用预期的防腐剂、组合物和混合物保存食品、化妆品、保健品和药品。这些预期的防腐剂、组合物和混合物可以范围从总组合物的约0.001%至约10%重量提供。在一些实施方案中,范围是总组合物的从约0.01%至约5%重量。在其它实施方案中,范围是总组合物的从约0.1%至约1%重量。
此外,公开了用于防腐剂和抗微生物组合物的包含植物提取物的混合物的组合物、化合物和方法,其中植物提取物包含至少一种富集一种或多种大环生物碱的苦味合欢(Albizia amara)种子提取物和富集一种或多种双酚木脂素的木兰属树皮提取物。
发现具有增强的抗微生物活性的化合物和提取物的独特共混物的构思借用自抗生素组合的实践。抗生素的协同作用的组合领域是极其广泛的且一些固定的组合在关于其对治疗具有耐药性的感染的作用方面已在商业上成功开发。通过高通量抗-大肠杆菌筛选超过10,216种有机提取物和水性提取物的植物库,其从世界各地收集的药用植物生成,苦味合欢(Albizia amara)种子提取物被鉴定为最佳先导,表现出具有40 ug/mL的MIC值的有效抗-革兰氏阴性抑制作用。生物测定-指导的分离和鉴定确认活性成分是布木柴胺C及其类似物。
苦味合欢(Albizia amara)种子提取物显示出有效的针对革兰氏阳性和革兰氏阴性菌的抑制作用,但针对白色念珠菌(Candida albicans)或巴西曲霉(Aspergillus brasiliensis)具有温和的抗-真菌活性。为寻找在USP章节<51>中类别2防腐所需的有效对抗革兰氏阳性、革兰氏阴性和真菌,主要是针对提高抗-真菌活性,特别是对抗白色念珠菌(C. albicans)和巴西曲霉(A. brasiliensis)的组合物,苦味合欢(Albizia amara)种子提取物与木兰属树皮提取物一起配制达到意想不到的增强效果。
令人惊讶且出乎意料地,木兰属树皮提取物的加入引起其针对白色念珠菌和巴西曲霉二者的抗-真菌活性的极大的增加,因此意味着这两种材料的组合的重要性。合并这两种植物材料的优点被确定,且对抗白色念珠菌和巴西曲霉二者的意想不到的协同作用被观察到,基于FCI指数分析,有益的效果超过了相加的相互作用。总之,认为以特定的比率放入这两种植物为组合物提供了新颖性,如其显著的抗菌活性和效果所证实的。
当苦味合欢(Albizia amara)种子提取物与木兰属树皮提取物按1:3和1:1的比率共混时,发现了一种有趣的协同作用。这两种植物以前从未以特定的比率合并在一起以产生预期的和公开的生物活性,这一般被理解为在这些预期的实施方案中的独特的组合。
组合物1A:1M的抗菌活性和功效,其中A代表苦味合欢(Albizia amara)种子提取物和M代表木兰属树皮提取物,按照USP <51>指南评价。组合物1A:1M,其为1:1比率的苦味合欢(Albizia amara)种子提取物和木兰属树皮提取物,在1 mg/mL的浓度时,显著地减少铜绿假单胞菌(P. aeruginosa)和巴西曲霉的计数(Log10减少分别在5.58和4.1),并且在48 h后显著地(如果不是完全地)消除金黄色葡萄球菌、大肠杆菌和白色念珠菌,并且对于全部5种微生物在7天、14天和28天后没有观察到细菌或真菌生长。事实上,所述成分中没有一个在量级方面显示出等效于预期的包含苦味合欢(Albizia amara)和木兰属的化合物或组合物所示活性的如此有效和广泛的抗微生物活性。此外,预期的和独特的约1A:1M的比率提供这种组合物对抗全部5种微生物,包括大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌、巴西曲霉和白色念珠菌的证实效果。
预期合欢属源自、得自或选自以下的至少一种 – 单独或彼此组合:苦味合欢(Albizia amara)、Albizia schimperiana、阔荚合欢 (Albizia lebbek)、含胶合欢(Albizia gummifera)、Albizzia inopinata、雨树(Albizia saman, Samanea saman=Pithecolobium saman), 热非合欢(Albizia adianthifolia)、Albizia adinocephala、灌木合欢(Albizia anthelmintica)、Albizia antunesiana、Albizia chevalieri、天香藤(Albizia corniculata)、白花合欢(Albizia crassiramea)、巧家合欢(Albiziaduclouxii)、Albizia glabra、合欢(Albizia julibrissin)、山合欢(Albizia kalkora)、缅甸合欢(Albizia lebbekoides)、Albizia myriophylla、Albizia nigricans、香合欢(Albizia odoratissima)、Albizia peterisana、Albizia poilanei、黄豆树(Albiziaprocera)、Albizia tanganyicensis、Albizia vialeana Pierre、西非合欢(Albiziazygia)、Aphelandra fuscopunctata、麻黄属(Ephedra spp.)、Verbascum pseudonobile、角蒿(Incarvillea sinensis)、紫毛蕊花(Verbascum phoenicum)、黑毛蕊花(Verbascumnigrum)、布氏大青(Clerodendrum buchneri)或金脉单药花(Aphelandra squarrosa)。
公开的苦味合欢(Albizia amara)提取物是可用作目标化合物或组合物的部分的预期的组分或成分。苦味合欢(Albizia amara)提取物可得自、源自或选自一种或多种任何合适的来源,包括Albizia schimperiana、阔荚合欢 (Albizia lebbek)、含胶合欢(Albizia gummifera)、Albizzia inopinata、雨树(Albizia saman, Samanea saman=Pithecolobium saman), 热非合欢(Albizia adianthifolia)、Albizia adinocephala、灌木合欢(Albizia anthelmintica)、Albizia antunesiana、Albizia chevalieri、天香藤(Albizia corniculata)、白花合欢(Albizia crassiramea)、巧家合欢(Albiziaduclouxii)、Albizia glabra、合欢(Albizia julibrissin)、山合欢(Albizia kalkora)、缅甸合欢(Albizia lebbekoides)、Albizia myriophylla、Albizia nigricans、香合欢(Albizia odoratissima)、Albizia peterisana、Albizia poilanei、黄豆树(Albiziaprocera)、Albizia tanganyicensis、Albizia vialeana Pierre、西非合欢(Albiziazygia)、Aphelandra fuscopunctata、麻黄属(Ephedra spp.)、Verbascum pseudonobile、角蒿(Incarvillea sinensis)、紫毛蕊花(Verbascum phoenicum)、黑毛蕊花(Verbascumnigrum)、布氏大青(Clerodendrum buchneri)、金脉单药花(Aphelandra squarrosa)或其组合。
苦味合欢(Albizia amara)提取物可富集一种或多种如本文预期的大环生物碱。在一些预期的实施方案中,合欢属提取物包含约0.01%-99.9%的大环生物碱。从合欢属或苦味合欢(Albizia amara)提取物分离的预期的生物碱用任何合适的溶剂,包括水、甲醇、乙醇、醇,水-混合的溶剂或其组合,或用超临界流体提取。在预期的实施方案中,苦味合欢(Albizia amara)提取物包含约0.01%至约99.9%大环生物碱。从苦味合欢(Albizia amara)提取物分离的预期的生物碱是布木柴胺A、B、C、D、E、F、G、H、I、J、K、布木柴胺L1、L2、L3、L4、L5、L6、13-去甲布木柴胺K、9-去甲布木柴胺K、1-去甲布木柴胺K、6'-羟基-9-去甲布木柴胺K、6'-羟基布木柴胺K、Felipealbizine A、Felipealbizine B、6′-羟基布木柴胺C、猴耳环碱、原甲碱(Protomethine)、Verbamethine、Verbametrine、Isoverbametrine、Isoverbamethine、Verbamekrine、Isoverbamekrine、Verbascine、Verbacine、Verbasitrine、Verballocine、Isoverbasitrine、Verballoscenine、Isoverbasikrine、N1-(Z)-对-甲氧基肉桂酰buchnerine、Buchnerine、Verbamedine、Verbascenine、Verbascenine、Isoverbamedine、Schweinine、Prelandrine、Incasine B’、Incasine B或其组合。
木兰属提取物是一种可用作目标化合物或组合物的部分的预期的组分或成分。木兰属提取物可从任何合适的来源获得,包括厚朴(Magnolia officinalis)、黄花木兰(Magnolia acuminate)、望春玉兰(Magnolia biondii)、夜香木兰(Magnolia coco)、白玉兰(Magnolia denudate)、望春花(Magnolia fargesii)、泰国木莲(Magnolia garrettii)、广玉兰(Magnolia grandiflora)、大叶木兰(Magnolia henryi)、紫玉兰(Magnolialiliflora)、恒春厚朴(Magnolia kachirachirai)、日本玉兰(Magnolia Kobus)、日本厚朴木兰(Magnolia obovata)、日本辛夷(Magnolia praecocissima)、百合木兰(Magnoliapterocarpa)、塔形木兰(Magnolia pyramidata)、有喙木兰(Magnolia rostrate)、柳叶木兰(Magnolia salicifolia)、天女木兰(Magnolia sieboldii)、二乔木兰(Magnoliasoulangeana)、星花木兰(Magnolia stellate)、弗吉尼亚木兰(Magnolia virginiana)、桦树木质素的降解产物(prod. of degradation of birch lignin)、小花老鼠簕(Acanthusebracteatus)、Aptosimum spinescens、里白葱木(Aralia bipinnata)、巴西松(Araucariaangustifolia)、猴爪杉(Araucaria araucana)、中亚苦蒿(Artemisia absinthium)、尖叶芸香草(Haplophyllum acutifolium)、大叶芸香(Haplophyllum perforatum)、北美鹅掌楸(Liriodendron tulipifera)、海风藤(Krameria cystisoides)、紫苏(Perillafrutescens)、散沫花(Lawsonia inermis)、肉豆蔻(Myristica fragrans) (nutmeg))、云南拟单性木兰(Parakmeria yunnanensis) (优选属名木兰属)、日本鳄梨(Perseajaponica)、风藤(Piper futokadsura)、Piper wightii、Rollinia mucosa、台湾檫木(Sassafras randaiense)、Scrophularia albida-colchica、瑞香狼毒(Stellerachamaejasme)、关东丁香(Syringa velutina)、海南蒲桃(Syzygium cumini)、Talaumagloriensis、Virola elongate、Urbanodendron verrucosum、Wikstroemia sikokiana或其组合。
木兰属提取物可富集一种或多种如本文预期的木脂素,包括二酚木脂素。预期的从木兰属提取物分离的木脂素用任何合适的溶剂,包括水、甲醇、乙醇、醇、水-混合的溶剂或其组合或用超临界流体提取。
在预期的实施方案中,木兰属提取物包含约0.01%-约99.9%的二酚木脂素、双酚木脂素或其组合。预期的从木兰属提取物分离的木脂素是厚朴酚、和厚朴酚、望春玉兰脂素A、2,3-双(4-羟基-3-甲氧基苯基)-2-丙烯醛、Denudadione C、丁香厚朴酚、8-[2-羟基-5-(2-丙烯基)苯基]-6-(2-丙烯基)-2H-1-苯并吡喃-2-酮、Denudanolide C、Denudanolide D、Denudanolide B、Denudanolide A、Denudatin A、Denudatin B;(+)-形式,4-羟基-6'-甲氧基-3,3'-双木酚(biligna)-7,7'-二烯-9,9'-二醛、4'-甲氧基厚朴二醛、5,5'-二-2-丙烯基-[1,1'-联苯基]-2,2'-二醇、2,2'-二胡椒酚、FEMA 4559、5,5'-二烯丙基-2,2'-二羟基联苯、冰片基厚朴酚、5,5'-二烯丙基-2-(3-甲基-2-丁烯氧基)联苯基-2'-醇、5,5'-二烯丙基-2-(烯丙氧基)联苯基-2'-醇、3',5-二烯丙基-2,4'-二羟基联苯、3',5-二-2-丙烯基-2,4'-联苯基二醇、5-烯丙基-3'-(1-丙烯基)联苯基-2,4'-二醇、3'-(1-丙烯基)-5-(2-丙烯基)-2,4'-联苯基二醇、3',5-二烯丙基-2-羟基-4'-甲氧基联苯、4'-O-甲基和厚朴酚、2-羟基-4'-甲氧基-3',5-二-2-丙烯基联苯、4,4'-二烯丙基-2,3'-二羟基二苯基醚、2-[3-羟基-4-(2-丙烯基)苯氧基]-5-(2-丙烯基)苯酚、2-羟基-3-甲氧基-4',5-二-2-丙烯基二苯基醚、4',5-二烯丙基-2-羟基-3-甲氧基二苯基醚、2-甲氧基-4-(2-丙烯基)-6-[4-(2-丙烯基)苯氧基]苯酚、辛夷脂素(Fargesin)、辛夷脂素(Methyl pluviatilol)、3,4-二甲氧基-3',4'-亚甲二氧基-7,9':7',9-双环氧木脂素、Kobusin、去甲氧基刚果荜澄茄脂素(Desmethoxyaschantin)、O-甲基薄荷醇、Spinescin、(+)-辛夷脂素、Planinin、辛夷脂素(Methyl pluviatilol)、云南拟单性木兰素A (parakmerin A)、6-烯丙基-7-(3,4-二甲氧基苯基)-2,3-二甲氧基-8-甲基三环[4.2.0.0.2,8]辛-3-烯-5-酮、木兰沙灵(Magnosalin)、双辣薄荷基厚朴酚、Kachirachirol B、粗毛淫羊藿苷(Acuminatin)、利卡灵D、eudeshonokiol A、Eudesmagnolol、桉脂素(Eudesmin);(+)-形式、(+)-表桉叶明(Epieudesmin)、(-)-表桉叶明、Kachirachirol A、Eupomatenoid 13、Fargesiphenol B、Fargesiphenol C、Fargesone A、Fargesone B、4,5-二甲氧基-3',4'-亚甲二氧基-2,7'-二氧代-5,8'-木酚(ligna)-3,6,8-三烯、4-(1,3-苯并间二氧杂环戊烯-5-基)-2,3,4,5-四氢-7-甲氧基-5-甲基-8H-2,5a-亚甲基-1-苯并氧杂环庚三烯-8-酮、苯丙木质素(Garrettilignan) A、苯丙木质素B、四氢-4-(3-羟基-4,5-二甲氧基苯基)-1H,3H-呋喃并[3,4-c]呋喃-1-酮、卡奇醇(Kachiranol)、7',9-二羟基-3,3',4,4',5-五甲氧基-7,9'-环氧木脂素、Magnone B、3,3',4,4',5,9-六甲氧基-7,9'-环氧木脂素-7'-酮、Magnolenin C、3',4,7,9,9'-五羟基-3,5'-二甲氧基-8,4'-氧基新木脂素、3,3'-二甲氧基-4,5:4',5'-双(亚甲二氧基)pyramidatin、3'-羟基-3,4,4',5,5'-五甲氧基pyramidatin、pyramidatinB、3,3',4',5'-四甲氧基-4,5-亚甲二氧基pyramidatin、3,3',4,4',5,5'-六甲氧基pyramidatin、pyramidatin C、pyramidatin、pyramidatin D、3-羟基-3',4,4',5,5'-五甲氧基pyramidatin、pyramidatin A、3-羟基-3',4,5-三甲氧基-4',5'-亚甲二氧基pyramidatin、pyramidatin F、pyramidatin G、pyramidatin H、pyramidatin E、5'-羟基-3,3',4,4',5-五甲氧基pyramidatin、Magnoshinin、2',3,4,4',5,6-六甲氧基-2,7'-环木酚(lign)-7-烯、Acanthoside B、Eleutheroside E1、3-羟基-3',4,4',5,5'-五甲氧基-7,9':7',9-双环氧木脂素、(+)-Episyringaresinol、Lirioresinol A、Symplicosigenol、Kobusinol B、Fargesol、9-O-Acetylfargesol、Magnolone、Biondinin B、Biondinin E、Magnone A、7,9,9'-三羟基-3,3',4-三甲氧基-8,4'-氧基新木脂素、赤式、苏式、Magnovatin A、Magnovatin B、Oleiferin C、3,4:3',4'-双(亚甲二氧基)-7-木脂素醇、7-羟基-3,4:3',4'-双(亚甲二氧基)木脂素、Liliflodione、Denudadione B、Denudadione A、Liliflol A、Liliflol B、Denudatone、3-[2',6-二羟基-5'-(2-丙烯基)[1,1'-联苯基-3-yl]]-2-丙烯醛、Randainal、厚朴醛B、厚朴醛C、6'-O-甲基厚朴醛B、4-脱氧-6-甲氧基厚朴醛A、4-甲氧基厚朴醛B、2',6-二羟基-5'-(2-丙烯基) [1,1'-联苯基]-3-甲醛、5-烯丙基-5'-甲酰基-2,2'-二羟基联苯、厚朴醛E、6-O-甲基厚朴醛E、9-羟基-3,3',4,4',5-五甲氧基-7,9'-环氧木酚-7'-烯、9,9'-二羟基-3,3',4,4',5-五甲氧基-2,7'-环木酚-7-烯、Magnolianin、Magnolignan I、Magnolignan B、Magnolignan A、Magnolignan D、Magnolignan C 6'-葡糖苷、Magnolignan C、Magnolignan E、Magnolignan F、MagnolignanG、Magnolignan H、2-[4-羟基-3-(2-丙烯基)苯基]-2,5-环己二烯-1,4-二酮、2-(3-烯丙基-4-羟基苯基)-1,4-苯醌、Magnosalicin; (7RS,7'SR,8RS,8'RS)-形式、MagnostellinB、Magnostellin B; 7,9-二差向异构体、5-甲氧基,5-[2-羟基-5-(2-丙烯基)苯基]-2-甲基苯并呋喃、3-羟基-3',4,4',5-四甲氧基-7,9',7',9-双环氧木脂素、3-De-O-methylmagnolin、Magnolin、3-O-Demethylaschantin、3'-O-Demethylaschantin、3-羟基-4,5-二甲氧基-3',4'-亚甲二氧基-7,9':7',9-双环氧木脂素、5'-羟基-4'-O-甲基薄荷醇、Epimagnolin A、7'-羟基-3,3',4,4'-四甲氧基-7,9'-环氧木脂素、Magnostellin A、Kobusinol A、4,7'-二羟基-3,3',4'-三甲氧基-7,9'-环氧木脂素、4',5,9-三羟基-3,3'-二甲氧基-7,9'-环氧木脂素、Fargesiphenol A、Liliflone、单萜烯基厚朴酚、辣薄荷基和厚朴酚、单萜烯基和厚朴酚、Saulangianin I、Sesamin; (-)-形式、Syringinoside、Syringin 4''-葡糖苷、3,3',4,5'-四甲氧基-7,9':7',9-双环氧木脂素、3',5'-二甲氧基-3,4-亚甲二氧基-7,9':7',9-双环氧木脂素、Galgravin、2,2'-二羟基-3-甲氧基-5,5'-二-2-丙烯基联苯、3-甲氧基厚朴酚、5,5'-二烯丙基-2,2'-二羟基-3-甲氧基联苯基或其这些的任何组合。
预期的化合物、药物组合物和组合物可包含或另外地包含至少一种抗微生物成分或由至少一种抗微生物成分组成。在一些实施方案中,至少一种抗微生物成分可包含补骨脂(Psoralea corylifolia)、姜黄素(Curcumin)、姜黄(Curcuma longa)、丁香酚(Eugenol)、高良姜(Alpinia galganga)、黄连(coptidis)、印度苦楝(Azadirachtaindica)、蜂胶(Propolis)、丁香油、苦参(Sophora flavescens)、槟榔(Areca catechu)、洋甘草(Glycyrrhiza glabra)、北美乔柏(Thuja plicata)、黄柏(Cortex phellodendri)、大黄(Rheum palate)、小良姜(Alpinia officinarum)、构树(Broussonetia papyriferra)、黄栌叶荚蒾(Viburnum cotinifolium)、大飞扬草(Euphorbia hirta Linn)、黄荆(Vitexnegundo),或其组合的植物粉末或植物提取物或由它们组成。
预期的化合物, 药物组合物和组合物可包含或另外地包含至少一种或多种已知的抗微生物防腐剂、组分或成分,由它们或基本由它们组成。在一些实施方案中,至少一种抗微生物成分可包含丙酸钙、苯甲酸钠、硝酸钠、亚硝酸钠、山梨酸钾、苯甲酸、水杨酸、山梨酸、醇、苯氧基乙醇、1,2-二醇(1,2 丙二醇、1,2 丁二醇、1,2 戊二醇、1,2-己二醇 )、1,3-二醇(1,3 丙二醇、1,3 丁二醇、1,3 戊二醇、1,3-己二醇)、1,5 戊二醇、苯扎氯铵、对羟基苯甲酸酯、亚硫酸盐(二氧化硫、亚硫酸氢钠、亚硫酸氢钾等)和EDTA二钠,和BHT (丁羟甲苯)和BHA (丁羟茴醚)、甲醛(通常在溶液中)、戊二醛(杀死昆虫),和甲基氯异噻唑啉酮或由它们组成。
所述组合物还包含药学或保健上或化妆品可接受的载体、稀释剂,或赋形剂,其中药物或保健制剂包含从约0.001%重量(wt%)至约10 wt%的提取物混合物的活性成分。这些预期的活性成分可以范围从总组合物的约0.001%至约10%重量提供。在一些实施方案中,范围是总组合物的从约0.01%至约5%重量。在其它实施方案中,范围是总组合物的从约0.1%至约1%重量。
本文还涵盖所公开的化合物的防腐剂或抗微生物剂。这些产物可能由例如所给予的化合物的氧化、还原、水解、酰胺化、酯化等引起,主要是由于酶促过程。因此,所预期的化合物是通过包括将所预期的化合物或组合物给予哺乳动物足以产生其代谢产物的时间的方法产生的那些化合物。通常通过以可检测的剂量将本公开的放射性标记的化合物给予动物(例如大鼠、小鼠、豚鼠、狗、猫、猪、绵羊、马、猴或人),允许足够时间供代谢的发生,然后从尿液、血液或其它生物样品中分离其转化产物,从而鉴定这样的产物。
如本文所用,短语“稳定化合物”和“稳定结构”可互换使用,并用于指示足够稳健以便经受从反应混合物中分离至有用的纯度并经受配制成有效的治疗剂的化合物。
如本文所用,术语“哺乳动物”包括人类和家养和非家养动物,家养动物例如实验室动物或家庭宠物,例如大鼠、小鼠、豚鼠、猫、狗、猪、牛、绵羊、山羊、马、兔、灵长类动物,非家养动物例如野生动物等。
如本文所使用的,术语“任选”或“任选地”可以互换使用,并且意味着随后描述的要素、组件、事件或情况可能发生或可能不发生,并且包括发生所述要素、组件、事件或情况的情形以及它们没有发生的情形。例如,“任选取代的芳基”是指芳基可以被取代或可以不被取代—换句话说,该描述包括取代的芳基和不具有取代基的芳基。
预期的化合物、药物组合物和组合物可以包含或另外包含或组成自至少一种药学上或保健上或化妆品可接受的载体、稀释剂或赋形剂。如本文所用,短语“药学上或保健上或化妆品可接受的载体、稀释剂或赋形剂”包括任何佐剂、载体、赋形剂、助流剂、甜味剂、稀释剂、防腐剂、染料/着色剂、增味剂、表面活性剂、润湿剂、分散剂、悬浮剂、稳定剂、等渗剂、溶剂或乳化剂,其已被美国食品和药物管理局批准为可接受用于人类或家养动物。
预期的化合物、药物组合物和组合物可以包含或另外包含或组成自至少一种药学上或保健上或化妆品可接受的盐。如本文所用,短语“药学上或保健上或化妆品可接受的盐”包括酸加成盐和碱加成盐。
如本文所用,短语“药学上或保健上或化妆品可接受的酸加成盐”是指保留游离碱的生物学有效性和性质的那些盐,其不是在生物学上或其它方面不希望的,并且是与无机酸和有机酸形成的,无机酸如盐酸、氢溴酸、硫酸、硝酸、磷酸等,有机酸如乙酸、2,2-二氯乙酸、己二酸、海藻酸、抗坏血酸、天冬氨酸、苯磺酸、苯甲酸、4-乙酰胺基苯甲酸、樟脑酸、樟脑-10-磺酸、癸酸、己酸、辛酸、碳酸、肉桂酸、柠檬酸、环拉酸、十二烷基硫酸、乙烷-1,2-二磺酸、乙磺酸、2-羟基乙磺酸、甲酸、富马酸、半乳糖酸、龙胆酸、葡庚糖酸、葡糖酸、葡糖醛酸、谷氨酸、戊二酸、2-氧代-戊二酸、甘油磷酸、乙醇酸、马尿酸、异丁酸、乳酸、乳糖酸、月桂酸、马来酸、苹果酸、丙二酸、扁桃酸、甲磺酸、粘酸、萘-1,5-二磺酸、萘-2磺酸、1-羟基-2-萘甲酸、烟酸、油酸、乳清酸、草酸、棕榈酸、双羟萘酸、丙酸、焦谷氨酸、丙酮酸、水杨酸、4-氨基水杨酸、癸二酸、硬脂酸、琥珀酸、酒石酸、硫氰酸、对甲苯磺酸、三氟乙酸、十一碳烯酸等。
如本文所用,短语“药学上或保健上或化妆品可接受的碱加成盐”是指保留游离酸的生物学有效性和性质的那些盐,其不是在生物学上或其它方面不希望的。这些盐通过向游离酸添加无机碱或有机碱来制备。来源于无机碱的盐包括钠、钾、锂、铵、钙、镁、铁、锌、铜、锰、铝盐等。在某些实施方案中,无机盐是铵盐、钠盐、钾盐、钙盐或镁盐。来源于有机碱的盐包括以下的盐:伯胺、仲胺和叔胺,包括天然存在的取代胺的取代胺,环胺和碱性离子交换树脂,如氨、异丙胺、三甲胺、二乙胺、三乙胺、三丙胺、二乙醇胺、乙醇胺、二甲基乙醇胺、2-二甲基氨基乙醇、2-二乙基氨基乙醇、二环己胺、赖氨酸、精氨酸、组氨酸、普鲁卡因、哈胺、胆碱、甜菜碱、苯乙苄胺、苄星、乙二胺、葡糖胺、甲基葡糖胺、可可碱、三乙醇胺、氨丁三醇、嘌呤、哌嗪、哌啶、N-乙基哌啶、聚胺树脂等。特别有用的有机碱包括异丙胺、二乙胺、乙醇胺、三甲胺、二环己胺、胆碱或咖啡因。
通常结晶产生所预期的化合物的溶剂化物或包括所预期的化合物。如本文所用,术语“溶剂化物”是指包含预期的化合物、药物组合物或组合物的一个或多个分子以及一个或多个溶剂分子的聚集体。溶剂可以是水,在这种情况下溶剂化物可以是水合物。或者,溶剂可以是有机溶剂。因此,所预期的化合物、药物组合物或组合物可作为水合物存在,包括一水合物、二水合物、半水合物、倍半水合物、三水合物、四水合物等以及相应的溶剂化形式。所预期的化合物、药物组合物或组合物可以是真溶剂化物,而在其它情况下,预期的化合物、药物组合物或组合物可以仅保留外来的水或者是水和一些外来溶剂的混合物。
防腐剂或抗微生物剂指预期的化合物、组合物或药物组合物和本领域普遍接受的用于食品、化妆品、保健品、口腔卫生产品和药品中递送抗微生物活性的介质的制剂。例如,可以将预期的防腐剂化合物,或组合物配制成或用作独立组合物,或作为处方药、非处方(OTC)药物、植物药、草药、顺势疗法药物或由政府机构审查和批准的任何其它形式的保健产品中的组分。示例性和预期的防腐剂组合物可以配制成或用作独立组合物,或者作为食物、新型食物、功能性食物、饮料、棒(bar)、食物香料、食物添加剂、药物食品、膳食补充剂或草药产品中的保健或生物活性组分。本领域通常接受的介质包括用于本领域的所有药学上或保健上可接受的载体、稀释剂或赋形剂。
在一些实施方案中,预期的组合物被配制为片剂、硬胶囊、软胶囊、粉剂、颗粒剂、液体剂、酊剂、sashay、即饮饮料单剂,或锭剂、化妆品膏、凝胶、洗剂、洗发剂、护发素、身体清洗剂、身体洗剂、染发剂、肤色剂、眼睛颜色剂、唇膏、香水、牙膏、漱口液、果汁、芦荟汁、酸奶、食品、软饮料、饮料、加工水果、奶酪产品、酒、松饼、花生酱、RTD、蛋白棒或小吃棒(snackbar)。
如本文所用,短语“富集”是指植物提取物或其它制备物具有的一种或多种活性化合物的量或活性与所述重量的提取之前的植物材料或其它来源或其它制备物中发现的所述一种或多种活性化合物的量或活性相比增加到至少约2倍直至至多约1000倍。在某些实施方案中,在提取之前的植物材料或其它来源或其它制备物的重量可以是干重、湿重或其组合。
如本文所用,“主要活性成分”或“主要活性组分”是指在植物提取物或其它制备物中发现的或在植物提取物或其它制备物中富集的一种或多种活性预期化合物,其能够产生至少一种生物活性。在某些实施方案中,富集提取物的主要活性成分将是在该提取物中富集的一种或多种活性化合物。通常,与其它提取物组分相比,一种或多种主要活性组分将直接或间接地赋予大部分(即大于50%)的一种或多种可测量的生物活性或效果。在某些实施方案中,根据提取物重量百分比的主要活性成分可以是较少组分(例如,在提取物中所含的小于约50%,25%,20%,15%,10%,5%或1%的组分),但仍提供大部分所需的生物活性。任何包含主要活性成分的预期组合物还可以含有次要活性成分,其可以或可以不有助于富集组合物的药物或保健活性,但没有达到主要活性组分的水平,并且仅次要活性成分在没有主要活性成分的情况下可能不是有效的。
如本文所用,短语“有效量”或“治疗有效量”是指所预期的化合物、药物组合物或组合物的量,当用于食品、化妆品、保健品、口腔卫生产品和药品时,足以防止细菌降解和抑制细菌、真菌和其它微生物生长。
本文使用的化学命名协议和任何结构图是I.U.P.A.C.命名系统的修改形式,使用ACD/Name Version 9.07软件程序或ChemDraw Ultra Version 11.0软件命名程序(CambridgeSoft),其中本公开的化合物在本文中被命名为中心核心结构,例如咪唑并吡啶结构的衍生物。对于本文所用的复杂化学名称,取代基在其连接的基团之前被命名。例如,环丙基乙基包含具有环丙基取代基的乙基骨架。
预期的防腐剂组合物可以是固体或液体形式。在一个方面,载体是颗粒状的,使得组合物例如呈片剂或粉末形式。载体可以是液体,其中组合物是例如口服糖浆、可注射液体或气雾剂,其可用于例如吸入给予。
当意图用于口服给予时,药物或保健组合物为固体或液体形式,其中半固体、半液体、悬浮液和凝胶形式被包括在本文认为是固体或液体的形式内。
作为用于口服给予的固体组合物,防腐剂组合物可以配制成粉末、颗粒剂、压片剂、丸剂、胶囊剂、口香糖、干胶片、棒或类似形式。这种固体组合物通常将含有一种或多种惰性稀释剂或可食用载体。另外,可以存在一种或多种以下物质:粘合剂,例如羧甲基纤维素、乙基纤维素、环糊精、微晶纤维素、黄蓍胶或明胶;赋形剂,如淀粉、乳糖或糊精;崩解剂,如海藻酸、海藻酸钠、Primojel®、玉米淀粉等;润滑剂,如硬脂酸镁或Sterotex®;助流剂,如胶体二氧化硅;甜味剂,如蔗糖或糖精;调味剂,如薄荷、水杨酸甲酯或橙味调味剂;和着色剂。
预期的防腐剂组合物可以为胶囊形式,例如明胶胶囊,除了上述类型的材料外,其还可以含有液体载体如聚乙二醇或油。
预期的防腐剂组合物可以是液体形式,例如酏剂、糖浆、凝胶、溶液、乳剂或混悬剂。作为两个例子,液体可以用于口服给予或通过注射递送。当意图用于口服给予时,除了本发明化合物之外,有用的组合物还含有甜味剂、防腐剂、染料/着色剂和增味剂的一种或多种。在意欲通过注射给予的组合物中,可以包括表面活性剂、防腐剂、润湿剂、分散剂、悬浮剂、缓冲剂、稳定剂和等渗剂中的一种或多种。
所预期的液体防腐剂组合物,无论它们是溶液、悬浮液还是其它类似形式,可以包括一种或多种以下佐剂:无菌稀释剂,例如注射用水,盐水溶液,诸如生理盐水、林格氏溶液、等渗氯化钠,可用作溶剂或悬浮介质的固定油,例如合成的甘油单酯或甘油二酯,聚乙二醇,甘油,丙二醇或其它溶剂;抗菌剂,如苯甲醇或对羟基苯甲酸甲酯;抗氧化剂,如抗坏血酸或亚硫酸氢钠;螯合剂,如乙二胺四乙酸;缓冲剂,如乙酸盐,柠檬酸盐或磷酸盐;以及调节张力的试剂,如氯化钠或葡萄糖。肠胃外制剂可以封装在安瓿、一次性注射器或由玻璃或塑料制成的多剂量小瓶中。生理盐水是通常有用的佐剂。可注射的药物或保健组合物是无菌的。
意图用于肠胃外或口服给予的预期的液体防腐剂组合物应包含一定量的预期化合物、药物组合物或组合物,以便获得合适的剂量。
预期的防腐剂组合物可以意图用于局部给予,在这种情况下,载体可以适当地包含溶液、乳液、乳膏、洗剂、软膏或凝胶基质。例如,所述基质可以包含以下一种或多种:凡士林、羊毛脂、聚乙二醇、蜂蜡、矿物油、例如水和醇的稀释剂,以及乳化剂和稳定剂。增稠剂可以存在于用于局部给予的药物或保健组合物中。如果打算用于透皮给予,组合物可以包括透皮贴剂或离子电渗装置。
预期的防腐剂组合物可以意图用于直肠给予,例如以栓剂的形式给予,其将在直肠中熔化并释放药物。用于直肠给予的组合物可以含有作为合适的非刺激性赋形剂的油性基质。这种基质包括羊毛脂、可可脂和聚乙二醇。
预期的防腐剂组合物可以包括改变固体或液体剂量单位的物理形式的各种材料。例如,组合物可以包括在活性成分周围形成包衣壳的材料。形成包衣壳的材料通常是惰性的,并且可以选自例如糖、虫胶和其它肠溶包衣剂。或者,可将活性成分装入明胶胶囊中。
所预期的固体或液体形式的防腐剂组合物可以包括与所预期的化合物结合从而有助于递送化合物的试剂。可以这种能力起作用的合适试剂包括单克隆或多克隆抗体、蛋白质或脂质体。
所预期的固体或液体形式的防腐剂组合物可以包括减小颗粒的尺寸以例如改善生物利用度。在有或没有赋形剂的情况下,组合物中的粉末、颗粒、微粒、微球等的尺寸可以是宏观的(例如,对眼睛可见或尺寸至少为100μm),微米级的(例如可以是范围从约100μm到约100nm的尺寸),纳米级的(例如,可以是不大于100nm的尺寸)以及在它们之间的任何尺寸或其任何组合以改善尺寸和堆密度。
预期的防腐剂组合物可以通过防腐剂领域众所周知的方法制备。例如,意图通过注射给予的防腐剂组合物可以通过将所预期的化合物与无菌蒸馏水组合以形成溶液来制备。可加入表面活性剂以促进形成均匀溶液或悬浮液。表面活性剂是与所预期的化合物非共价相互作用,以促进化合物在水性递送系统中的溶解或均匀悬浮的化合物。
预期的化合物、组合物和药物组合物或其药学上或保健上可接受的盐以治疗有效量给予,所述治疗有效量将根据多种因素而变化,包括所使用的具体化合物的活性;化合物的代谢稳定性和作用时间长度;患者的年龄、体重、一般健康状况、性别和饮食;给予的方式和时间;排泄率;药物组合;特定疾病或病症的严重程度;和受试者正在接受的治疗。
预期的化合物、组合物和药物组合物或其药学上或保健上可接受的衍生物也可以与一种或多种其它治疗剂的给予同时给予,或在一种或多种其它治疗剂的给予之前或之后给予。此类组合疗法包括给予含有预期的化合物和一种或多种另外的活性剂的单一药物或保健剂量制剂,以及以其自身分开的药物或保健剂量制剂给予预期的化合物和每种活性剂。例如,所预期的化合物和另一种活性剂可以以单一口服剂量组合物(例如片剂或胶囊)一起给予患者,或者每种药物可以以分开的口服剂量制剂给予。当使用分开的剂量制剂时,所预期的化合物和一种或多种另外的活性剂可在基本上相同的时间给予,即同时给予,或者在分开的交错时间给予,即依次给予;组合疗法被理解为包括所有这些方案。
应该理解的是,在本说明书中,只有当这样的贡献产生稳定的化合物时,所描述的式的取代基或变量的组合才是允许的。
本领域技术人员还应该理解的是,在本文所述的方法中,中间体化合物的官能团可能需要被合适的保护基团保护。这种官能团包括羟基、氨基、巯基和羧酸。适用于羟基的保护基包括三烷基甲烷基或二芳基烷基甲硅烷基(例如叔丁基二甲基甲硅烷基、叔丁基二苯基甲硅烷基或三甲基甲硅烷基)、四氢吡喃基、苄基等。氨基、脒基和胍基的合适保护基包括叔丁氧基羰基、苄氧基羰基等。适用于巯基的保护基包括C(O)R”(其中R”是烷基、芳基或芳基烷基)、对甲氧基苄基、三苯甲基等。羧酸的合适保护基包括烷基、芳基或芳基烷基酯。保护基可以根据本领域技术人员已知的和本文所述的标准技术添加或去除。“Green, T.W.and P.G.M. Wutz, Protective Groups in Organic Synthesis (1999), 3rd Ed.,Wiley”中详细描述了保护基的使用,其全部内容通过引用并入本文。如本领域技术人员将理解的,保护基还可以是聚合物树脂,例如Wang树脂、Rink树脂或2-氯三苯甲基氯树脂。
本领域技术人员还会理解,尽管所预期的化合物的这种被保护的衍生物本身可能不具有药理学活性,但它们可以被给予哺乳动物,然后在体内代谢以形成具有药理活性的化合物。因此这些衍生物可以被描述为“前药”。所预期的化合物的所有前药都包括在本公开的范围内。
此外,通过本领域技术人员已知的方法,通过用合适的无机或有机碱或酸处理,可以将以游离碱或酸形式存在的预期化合物转化为其药学上或保健上可接受的盐。所预期的化合物的盐可以通过标准技术转化为它们的游离碱或酸形式。
在一些实施方案中,所预期的化合物、组合物和/或药物组合物可以从植物来源分离,例如从实施例中和整个本申请的其它地方包括的那些植物分离。用于分离预期提取物和化合物的合适的植物部分包括叶、树皮、树干、树干皮、茎、茎皮、枝条、块茎、根、根皮、树皮表面(如周皮或复周皮,可包括木栓、木栓形成层、栓内层或其任何组合)、嫩枝、根状茎、种子、果实、雄蕊群、雌蕊、花萼、雄蕊、花瓣、萼片、心皮(雌蕊)、花或其任何组合。预期的植物提取物源自选自以下的至少一种植物部分:茎、茎皮、树干、树干皮、枝条、块茎、根、根皮、嫩枝、种子、根状茎、花和其它生殖器官、组织培养物和干细胞培养物、叶、其它气生部分或其组合。在一些相关的实施方案中,预期的化合物从植物来源分离并合成修饰以包含任何所述的取代基。就这一点而言,从植物中分离的预期化合物的合成修饰可以使用本领域已知的并且完全在本领域普通技术人员的知识范围内的任何数量的技术来完成。
实施例
实施例1
有机提取物的制备
将干燥研磨的植物材料(20 g)装入两个100 mL不锈钢管并于80℃和1500 psi的压力下,使用ASE 300自动提取器,用有机溶剂混合物(二氯甲烷/甲醇按1:1的比率)提取两次。自动过滤并收集提取物溶液。有机提取物溶液用旋转蒸发器蒸发,得到粗制有机提取物(OE)。不锈钢管用新鲜溶剂冲洗并用氮气吹洗至干,然后转换至在50℃水性提取。过滤水性溶液并冻干以提供水性提取物(AE)。
实施例2
针对大肠杆菌(Escherichia coli)的抗-微生物活性的高通量筛选
在96-孔微量滴定板中,对于针对大肠杆菌的抗微生物活性,对具有10,216种 OE和AE的植物库用高通量筛选法进行筛选。微生物培养物大肠杆菌KCTC2571 (= ATCC8739) 被用作试验微生物。LB肉汤被用作孔中的稀释剂或培养基。于37℃培养细菌培养物24 h。以250ug/mL的浓度,对植物库样品的每个样品按一式两份进行筛选。将180 ul大肠杆菌培养物按3 × 105 CFU/mL的接种规模加入各孔并与20 ul试验样品混合。未经处理的200 ul细菌培养物被用作对照,且200 ul LB肉汤被用作空白。于37℃培养细菌培养物24 h并对每个样品于600 nm测量OD。根据以下方程计算抑制作用。葡萄籽提取物被用作阳性对照。初步结果显示出82种提取物在250 ug/mL具有超过80%的抑制作用,在50 ug/mL对它们进行进一步的测试。11种植物提取物在50 ug/mL的浓度表现出80%或更高的抑制作用。对该11种击中(hit),使用系列稀释的相同方法测定MIC99值。基于MIC99值选择击中植物以供进一步的开发。苦味合欢(Albizia amara)种子是从该筛选选出的最高击中,其具有在12.5 ug/mL的MIC99值的有效抗-大肠杆菌活性。
实施例3
得自苦味合欢(Albizia amara)种子的有机提取物的制备
将总共100克干燥的苦味合欢(Albizia amara)种子粉末装入5个100 mL不锈钢管并于80℃和1500 psi的压力下,使用ASE 350自动提取器,用甲醇提取两次。自动过滤并收集提取物溶液。有机提取物溶液用旋转蒸发器蒸发,得到粗制有机提取物(OE) (25.1 g,25.1%)。
类似的结果使用相同的程序获得,但有机溶剂用甲醇或乙醇代替以分别提供甲醇提取物(ME)或乙醇提取物(EE), 甲醇:H2O (7:3)提取物、甲醇:H2O (1:1)提取物、甲醇:H2O(3:7)乙醇:H2O (7:3)提取物、乙醇:H2O (1:1)提取物、乙醇:H2O (3:7)提取物和水提取物。
表1:用不同溶剂提取的苦味合欢(Albizia amara)种子提取物
实施例4
得自苦味合欢(Albizia amara)种子提取物的活性化合物的分级分离、纯化和鉴定及定量
生物测定指导的分离导致活性大环生物碱布木柴胺C的分离和鉴定。将2 g合欢属种子甲醇提取物装入用MeOH和0.05%三氟乙酸在水中的混合液(55% MeOH-75% MeOH的范围)的溶剂系统洗脱的C18填充开放柱。收集9个流分。使活性流分40 mg溶于4 mL水中。然后将8mL乙酸乙酯加入到样品中。离心后,收集较低的层并重复这种程序3次。然后使样品溶于PH值11的4 mL氢氧化铵水中并用乙酸乙酯8mL洗涤3次,得到布木柴胺C (23.5 mg)。选择甲醇/乙醇作为用于提取的最终溶剂,因为甲醇或乙醇提取物显示出在最终提取中的最高的生物碱含量。
在由不同溶剂系统提取的提取物中的布木柴胺C含量可通过HPLC方法如下分析:使用RP-C18柱(Phenomenex, 4.6x250mm, 5µm),用甲醇和0.5% TFA在水中的梯度洗脱,通过UV检测器在210 nm或ELSD检测器以1 mL/min的流速检测。根据与内部分离和鉴定的标准化合物比较来鉴定布木柴胺C峰。与用水和50%甲醇/H2O提取物比较,甲醇提取物(RN368-29-01)具有最高的布木柴胺C含量,并显示出具有40 ug/mL的MIC值的最佳抗-大肠杆菌活性。这种结果与布木柴胺C及其类似物作为担负这种植物的抗-革兰氏阴性细菌活性的活性成分的发现和鉴定一致。来自不同物种、部分和从不同地点和季节收集的植物提取物中的布木柴胺含量可在0-6%范围内变化。苦味合欢(Albizia amara)种子的甲醇提取物被鉴定为布木柴胺类型生物碱的优良来源。
表2:苦味合欢(Albizia amara)种子提取物的布木柴胺C含量和对抗大肠杆菌的MIC
提取物ID | 提取 | 布木柴胺C | MIC (ug/mL) |
RN368-29-01 | 甲醇提取物 | 1.8% | 40 |
RN368-29-02 | 50%甲醇/水提取物 | 1.6% | 100 |
RN368-28-01 | 水提取物 | 1.1% | 100 |
实施例5
不同合欢属物种的抗-微生物活性
为寻找具有良好抗-革兰氏阴性菌活性的合欢属材料,不同物种和不同部分的合欢属植物从几个具有不同的地质位置的国家包括中国、印度、巴拿马、加纳和津巴布韦收集。按照如在实施例2中描述的方案评价每种合欢属材料提取物的抗-大肠杆菌活性并测定MIC值,且抗-微生物活性结果示于表3。
表3. 合欢属提取物的体外抗-大肠杆菌活性
植物物种 | 收集ID | 植物部分 | 来源国 | MIC (ug/mL) |
苦味合欢 | R00557 | 种子 | 印度 | 40 |
苦味合欢 | R00224 | 种子 | 津巴布韦 | >100 |
合欢 | R00558 | 种子 | 中国 | >100 |
阔荚合欢 | R00584 | 种子 | 印度 | >100 |
黄豆树 | R00585 | 种子 | 印度 | >100 |
A. richardiana | R00600 | 种子 | 印度 | >100 |
南洋楹(A. falcataria) | R00610 | 种子 | 印度 | >100 |
苦味合欢 | R00581 | 叶子 | 印度 | >100 |
苦味合欢 | R00582 | 树皮 | 印度 | >100 |
苦味合欢 | R00583 | 根 | 印度 | >100 |
A. petersana | R00226 | 根皮 | 津巴布韦 | >100 |
含胶合欢 | R00225 | 茎皮 | 津巴布韦 | >100 |
合欢 | R00554 | 花 | 中国 | >100 |
合欢 | R00555 | 树皮 | 中国 | >100 |
山合欢 | R00567 | 树皮 | 中国 | >100 |
阔荚合欢 | R00568 | 树皮 | 中国 | >100 |
阔荚合欢 | E1373 | 树皮 | 印度 | >100 |
苦味合欢 | R00581 | 叶子 | 印度 | >100 |
苦味合欢 | R00582 | 树皮 | 印度 | >100 |
苦味合欢 | R00583 | 根 | 印度 | >100 |
雨树 | P03417 | 叶子 | 巴拿马 | 250 |
雨树 | P01124 | 叶子 | 加纳 | >150 |
雨树 | P01125 | 根皮 | 加纳 | 150 |
雨树 | P01126 | 茎皮 | 加纳 | 150 |
实施例6
苦味合欢(Albizia amara)种子提取物和布木柴胺C的抗微生物活性
对苦味合欢(Albizia amara)种子提取物和活性标记化合物布木柴胺C针对细菌金黄色葡萄球菌、铜绿假单胞菌、大肠杆菌,和真菌巴西曲霉和白色念珠菌的最小抑制浓度进行测定。最小抑制浓度方法(MIC)按照一般微生物学方案进行以测量可抑制微生物在液体中增殖的抗微生物剂的最低水平。在液体培养基中准备用于细菌或在琼脂上准备用于真菌的试验微生物。试验微生物的悬浮液通过在适宜的肉汤溶液,通常在Mueller-Hinton肉汤中稀释实现标准化。在96-孔微量滴定板或在小的试管中,通过Mueller-Hinton肉汤或其它适宜的培养基进行几个系列的1:1稀释,制备试验物质。含有稀释的试验物质的所有孔或试管分别用试验微生物接种,导致制品在所有试验容器中的一个附加和最终的稀释。将微量滴定板或试管孵育18-24小时。在孵育期后,进行观察以确定为孔中试验物质的最低浓度的最小抑制浓度(MIC),其中未观察到浊度(指示试验微生物生长)和最低杀菌浓度(MBC)。
针对类别2要求的5种微生物,包括金黄色葡萄球菌(Staphylococcus aureus)(ATCC 6538)、大肠杆菌(Escherichia coli)(ATCC 8739)、铜绿假单胞菌(Pseudomonas aeruginosa) (ATCC 9027)、白色念珠菌(ATCC 10231)、巴西曲霉(ATCC 16404),测试了苦味合欢(Albizia amara)种子提取物RN368-31-MIX和布木柴胺C。苦味合欢(Albizia amara)种子提取物和布木柴胺C二者都显示出有效的抗-大肠杆菌活性,对于种子提取物的MIC值为62.5 ug/mL,而对于布木柴胺C为31.25。对于种子提取物和布木柴胺C观察到相对较弱的抗-真菌活性。针对6种其它微生物进一步测试了布木柴胺C,其MIC和MBC结果示于表5中。布木柴胺C显示出最有效的对抗酿脓链球菌(Streptococcus pyogenes)的功效(具有<0.97 ug/mL的MIC)。它也显示出对抗须发癣菌(Trichophyton mentagrophytes)、红色毛癣菌(Trichophyton rubrum)、痤疮丙酸杆菌(Propionibacterium acnes)和表皮葡萄球菌(Staphylococcus epidermis)的显著功效。
表4:苦味合欢(Albizia amara)种子提取物RN368-31-MIX和布木柴胺C的抗-微生物活性.
表5:布木柴胺C针对其它微生物的抗-微生物活性
生物体 | MIC | MBC |
犬小孢子菌 | >0.0375% (375 ug/mL) | >0.0375% (375 ug/mL) |
须发癣菌 | 0.001172% (11.7 ug/mL) | 0.001172% (11.7 ug/mL) |
红色毛癣菌 | 0.001172% (11.7 ug/mL) | 0.004688% (46.8 ug/mL) |
痤疮丙酸杆菌 | 0.0001953% (1.95 ug/mL) | 0.00078125% (7.8 ug/mL) |
表皮葡萄球菌 | 0.003125% (31.25 ug/mL) | 0.003125% (31.25 ug/mL) |
酿脓链球菌 | <0.00009765% (<0.97 ug/mL) | <0.000097656% (<0.97 ug/mL) |
实施例7
分析木兰属茎皮提取物的分析方法
采用RP-HPLC方法,通过活性标记化合物和厚朴酚及厚朴酚的定量分析木兰属茎皮提取物。超声处理大约10分钟,制备作为甲醇溶液的提取物。使烧瓶冷却至室温并用提取方法的QS;充分混合并通过0.45 um尼龙注射器滤器过滤,注射20 µl溶液并分析。木兰属茎皮提取物中的厚朴酚及和厚朴酚含量通过RP-HPLC方法,在具有C18柱的Agilent HPLC/PDA系统(Phenomenex, USA)上定量。二元纯净水和乙腈溶剂体系被用于在35℃的柱温下,以1 mL/min的流速,用77%乙腈在水中的等度洗脱18 min,以290 nm的波长检测厚朴酚及和厚朴酚。经测定木兰属茎皮提取物(FP072312-01)中的和厚朴酚及厚朴酚含量分别为51.2%和47.2%,在提取物中的总含量为98.4%。
木兰属树皮中的和厚朴酚及厚朴酚的天然含量据报道分别在2-11%和0.3-4.6%的范围内。市售木兰属树皮提取物中的和厚朴酚及厚朴酚的总含量可以是富集的并定制为1-99%的范围。
实施例8
木兰属茎皮提取物的抗-微生物活性
中文中具有通用名厚朴的厚朴(Magnolia)树皮是具有非常广泛应用的流行的传统草药之一。含有厚朴树皮的许多制剂被用于治疗肺病例如包括咳嗽和哮喘或肠道感染和痉挛,减轻不同原因的腹部肿胀和水肿。精油被鉴定为具有两种主要标记化合物和厚朴酚及厚朴酚的活性成分。现代研究表明厚朴茎皮提取物表现出有效的抗-微生物活性。选择7种微生物以测试抗-微生物活性和厚朴作为抗-微生物剂的潜在用途,包括细菌金黄色葡萄球菌、大肠杆菌,和真菌菌株犬小孢子菌(Microsporum canis)、须发癣菌、红色毛癣菌、巴西曲霉和白色念珠菌。MIC和MBC按照如在实施例6中所述的标准方案测定,活性结果见表6。除了抗-细菌活性,厚朴茎皮提取物还显示了有效的抗-真菌活性,具有对抗白色念珠菌的80ug/mL的MIC值。
表6:厚朴茎皮提取物FP072312-01的抗-微生物活性
生物体/菌株 | MIC (ug/mL) | MBC (ug/mL) |
金黄色葡萄球菌 | 80 | * |
大肠杆菌 | 阴性 | 阴性 |
铜绿假单胞菌 | 阴性 | 阴性 |
白色念珠菌 | 80 | * |
巴西曲霉 | 400 | * |
犬小孢子菌 | * | 118 |
须发癣菌 | 59 | 59 |
红色毛癣菌 | 59 | 59 |
*未能测定
实施例9
合欢属种子提取物和木兰属树皮提取物的混合物的抗-真菌活性
为发现有效对抗在USP章节<51>的类别2防腐剂中要求的全部5种微生物,主要针对提高抗-真菌活性,特别是对抗白色念珠菌和巴西曲霉的组合物,将苦味合欢(Albizia amara)种子提取物和厚朴树皮提取物共混在一起以寻找意想不到的增强效果。
这两种材料通过混合溶于所需量甲醇中的样品,以不同的比率配制,然后真空干燥得到混合物。通过生产,苦味合欢(Albizia amara)种子提取物和厚朴树皮提取物可以所需的比率直接混合以制备合并的组合物。
组合物1A:1M和1A:3M,其中A代表苦味合欢(Albizia amara)种子提取物和M代表厚朴树皮提取物,产生具有在30 ug/mL的对抗白色念珠菌的MIC的类似抑制作用,具有在130 ug/mL对抗巴西曲霉的MIC的相对较弱活性。将第三种成分补骨脂(Psoralea corylifolia)种子提取物(P)以3P的比率加入到1A:6M组合物中,然而这种3个成分制剂(1A:6M:3P)与两成分组合物比较,未显示出更优越的活性。给出这样的事实,即1:1比率的苦味合欢(Albizia amara)种子提取物和厚朴树皮提取物组合物(416-145-50)导致对抗白色念珠菌和巴西曲霉二者的最佳的MIC。这种组合物被认为是先导组合物并被选择用于按照<USP51>章节(在实施例12详述)进一步评价抗-微生物有效性试验。
表7:对抗白色念珠菌和巴西曲霉的组合的抗-微生物活性.
实施例10
合欢属种子提取物和木兰属树皮提取物混合物的组合物的协同作用评价
体外抗真菌组合通常基于分数抑制浓度(FIC)指数评价,其代表每个测试的物质的FIC的总和。每个物质的FIC被定义为(组合中药物A的MIC/药物A单独的MIC)。FIC指数方程是基于药物自身不能相互作用,因而药物自身组合的效果将始终以FIC指数1而相加的假设。FIC指数低于或高于1表示在两种合并的药物之间的相互作用方面的协同作用或是拮抗作用。考虑到2-倍药物稀释方案,在0.5-4范围内的FIC指数被认为所述药物组合没有相互作用,即既没有相加的相互作用,也没有无差异(indifference)的相互作用。0.5或更少的截止值被提示为界定协同作用,而截止值4或以上被解释为拮抗作用(Farrar 1973; Huang 2013;Odds, 2003; Pankey, 2005)。
分数抑制浓度(FIC)用以下方程式计算:药物A的FIC (FIC A) = 组合中的药物A的MIC / 药物A单独的MIC,和药物B的FIC (FIC B) = 组合中的药物B的MIC / 药物B单独的MIC]。FIC指数(FICI),计算为每个FIC的总和(∑FIC)。对于组合研究的FIC指数如在表8中所示计算。计算的1A:1M和1A:3M对抗白色念珠菌的指数是0.187和0.292。对于巴西曲霉,类似的计算导致对于1A:1M和1A:3M的FIC指数分别为0.293和0.309。对于1A:1M组合的0.187和0.282的FCI指数显示出作为协同效应而不是相加效应的更大确定性。对于1A:3M组合,观察到对抗这两种真菌菌株的类似的协同效应(具有0.282和0.309的FIC指数)。1A:6M:3P组合具有弱的对抗白色念珠菌(C. albican)的协同效应,但对巴西曲霉没有相互作用的效应。
这种组合研究的抗-真菌活性表示以特定的比率配制这两种成分时存在协同作用。已发现1A:1M的组合具有增强的针对白色念珠菌和巴西曲霉二者的抗-真菌效果,其基于FIC指数分析(FIC指数小于0.5)被分类为协同的相互作用。将苦味合欢(Albizia amara)种子提取物和厚朴树皮提取物放在一起的优点通过其对抗白色念珠菌和巴西曲霉二者的意外的增强的抗-真菌活性证实。
表8:苦味合欢(Albizia amara)种子提取物和厚朴茎皮提取物的组合物的意外的协同抗-真菌活性
实施例11
合欢属种子提取物和木兰属树皮提取物的混合物的有效性试验
预期的防腐剂的抗菌活性和功效按照USP <51>指南评价。USP <51>试验方法是一种将抗微生物防腐剂加入到非-灭菌剂量形式中的定量评价。用于这种试验的参数由天然产物以及它适用于四个类别中的哪一类确定。典型的接触时间延长至28天,且在7天间隔中对剩余微生物含量进行观察。这种试验在传统上伴随着中和验证测定,以确认所用的中和方法适用于试验物质和微生物。使试验物质1A:1M组合(416-145-50)以1 mg/mL的浓度溶于DMSO。结果示于图3中。试验微生物金黄色葡萄球菌(ATCC 6538)、大肠杆菌(ATCC 8739)、铜绿假单胞菌(ATCC 9027)、白色念珠菌(ATCC 10231)、巴西曲霉(ATCC 16404)通过在液体中或在琼脂培养基上生长来制备。将液体培养物中生长的微生物离心并在试验之前洗涤。试验微生物的悬浮液通过在缓冲盐水溶液中稀释进行标准化。将试验和对照物质以类似的已知体积分配至无菌容器中。独立体积的试验和对照物质用各种试验微生物接种,混合并孵育。即刻收获对照物质并表示在试验开始时,或时间零存在的浓度。
在每次接触时间结束时通过化学中和来收获孵育的试验物质。存活的微生物的数目在2、7、14和28天评价,对数减少量根据在时间零时观测到的初始浓度计算。Log10减少被计算为Log (B/A),其中B = 接种后即刻在对照物质中的活的试验微生物数量,和A = 在接触时间后试验物质中的活的试验微生物数量。416-145-50显著地减少铜绿假单胞菌和巴西曲霉的计数(分别在5.58和4.1的Log10减少)并在2天后显著地(如果不是完全的话)消除金黄色葡萄球菌、大肠杆菌和白色念珠菌,并在7天、14天和28天后针对全部5种微生物均未观察到细菌或真菌生长。这项研究清楚地表明这种组合物416-145-50对抗大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌、巴西曲霉和白色念珠菌的有效性,并满足类别2要求,即14天不少于初始计数的2-Log10减少和在28天对细菌没有自14天计数的增加,以及在14和28天对酵母和霉菌没有自初始计算的计数的增加。
表9:对于1 mg/mL的416-145-50的菌落计数和Log减少
注释:该测定的检测限是5.00E+00 CFU/mL。无微生物恢复的样品在图表中被报告为<5.00E+00。
实施例12
合欢属种子提取物和木兰属树皮提取物的混合物的有效性试验
0.5 mg/mL浓度的1A:1M组合(416-145-50)针对大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌、巴西曲霉和白色念珠菌的抗菌活性和功效按照在实施例12中描述的USP <51>指南进一步评价。结果示于图4中。在48小时、7、14和28天评估存活微生物的数量并基于在时间0观察到的初始浓度计算对数减少,如于表10中所示。这项研究清楚地表明0.05%的这种组合物416-145-50对抗全部5种微生物大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌、巴西曲霉和白色念珠菌的有效性并满足类别2要求,即14天不少于初始计数的2-Log10减少和在28天对细菌没有自14天计数的增加,以及在14和28天对酵母和霉菌没有自初始计算的计数的增加。
表10:416-145-50在500 μg/mL时的菌落计数和Log减少
注释:该测定的检测限是5.00E+00 CFU/mL。无微生物恢复的样品在图表中被报告为<5.00E+00。
实施例13
合欢属种子提取物和木兰属树皮提取物的混合物的抗微生物活性
对于苦味合欢(Albizia amara)种子提取物和厚朴树皮提取物的1A:1M组合,测定对抗细菌金黄色葡萄球菌、铜绿假单胞菌和大肠杆菌的最小抑制浓度。最小抑制浓度方法(MIC)按照普通微生物学方案进行,以如实施例6中所述测量可抑制微生物在液体中的增殖的抗微生物剂的最低水平,活性结果示于表11中。针对金黄色葡萄球菌的有效的抗微生物活性被发现为20 ug/mL的MIC。对于这种苦味合欢(Albizia amara)种子提取物和厚朴树皮提取物组合,对抗革兰氏阴性菌大肠杆菌和铜绿假单胞菌二者的MIC被测定为1000 ug/mL。
表11:1A:1M组合(416-145-50)的抗-微生物活性
生物体/菌株 | MIC (ug/mL) |
金黄色葡萄球菌 | 20 |
大肠杆菌 | 1000 |
铜绿假单胞菌 | 1000 |
实施例14
苦味合欢(Albizia amara)种子提取物(在PH=3)针对大肠杆菌的抗微生物活性
对于苦味合欢(Albizia amara)种子提取物(RN368-31-mix),测定在酸性(PH=3)条件下对抗革兰氏阴性菌大肠杆菌的最小抑制浓度。
最小抑制浓度方法(MIC)按照普通微生物学方案进行,以测量可抑制微生物在液体中的增殖的抗微生物剂的最低水平。使试验物质溶于含有柠檬酸和柠檬酸钠在水中的混合液的缓冲溶液(PH=3)中,然后在96-孔微量滴定板中,通过Mueller-Hinton肉汤或其它适宜的培养基通过几个系列的1:1稀释而制备。含有稀释的试验物质的所有孔或管分别用试验微生物接种,导致在所有试验容器中的制品的一个附加的和最终的稀释液。将微量滴定板孵育18-24小时。在孵育期后,进行观察以确定为孔中试验物质的最低浓度的最小浓度(MIC),其中未观察到浊度(指示试验微生物生长)。苦味合欢(Albizia amara)种子提取物在PH=3时对抗大肠杆菌的MIC是125 ug/mL,比在中性条件下的MIC (62.5 ug/mL)活性稍弱。
实施例15
苦味合欢(Albizia amara)种子提取物和厚朴树皮提取物组合(PH=3)对抗巴西曲霉的抗真菌活性
在酸性条件(PH=3)下,测定苦味合欢(Albizia amara)种子提取物和厚朴树皮提取物组合对抗巴西曲霉的最小抑制浓度。
最小抑制浓度方法(MIC)按照普通微生物学方案进行,以测量可抑制微生物在液体中的增殖的抗微生物剂的最低水平。使试验物质溶于含有柠檬酸和柠檬酸钠在20%DMSO/水中的混合液的缓冲溶液(PH=3)中,然后在96-孔微量滴定板中,通过Mueller-Hinton肉汤或其它适宜的培养基通过几个系列的1:1稀释而进一步制备。含有稀释的试验物质的所有孔或管分别用试验微生物接种,导致在所有试验容器中的制品的一个附加的和最终的稀释液。将微量滴定板或试管孵育18-24小时。在孵育期后,进行观察以确定为孔中试验物质的最低浓度的最小浓度(MIC),其中未观察到浊度(指示试验微生物生长)。这种1A:1M组合在PH=3时的MIC被测定为125 ug/mL。这种1A:1M组合在酸性条件下的抗真菌活性与400 ug/mL的原始MIC比较有改进。
实施例16
合欢属种子提取物和木兰属树皮提取物的混合物的制剂
1A:1M组合(B1-11202015)用非-离子o/w乳液系统分别以两个浓度0.1%和0.5%进一步配制。3% (%重量) 1,2-己二醇被用作B1-11202015的以重量计在含有PH 6.0-6.5范围内的乳液的霜剂制剂中的载体溶剂。在加入到霜剂基质之前,于50℃使B1-11202015完全分散于3%重量的1,2 己二醇中。通过于70℃混合所有成分直至其为均匀的并且所有固体材料已经熔化和混合来制备霜剂基质。在冷却至60℃后,通过加入20% NaOH溶液或20%柠檬酸溶液,将霜剂基质材料的PH值调节至6.0-6.5。在加入3% 1,2 己二醇和B1-11202105之前,将霜剂基质冷却至50℃。如果必要,将配制的材料的PH值进一步调节至6.0-6.5的范围。以相同的方式,制备具有0.5% 1A:1M组合(1940601)和0.1% 1A:1M (1940602)的两个配制的样品。
实施例17
配制的合欢属种子提取物和木兰属树皮提取物组合的有效性试验
非-离子o/w乳液配制的1A:1M组合在0.5%浓度(1940601)时针对大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌、巴西曲霉和白色念珠菌的抗菌活性和功效按照在实施例11中描述的USP <51>指南评价。结果示于图5中。在2、7、14和28天评估存活微生物的数量并基于在时间0观察到的初始浓度计算对数减少,如于表12中所示。这项研究清楚地表明0.5%的这种组合物1940601对抗全部3种细菌(大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌)和酵母白色念珠菌的有效性,在2天后,以及延长至7天、14天,和28天均未观察到细菌或真菌生长。对于巴西曲霉,1940601显示出相对较弱的抑制作用,在D2和D7的Log10减少分别为0.73和1.53。其在D14 (2.32)和在D28 (3.32)时确实达到2- LOG10减少。
这项研究清楚地表明这种组合物1940601作为通过USP51标准的类别2产品,对抗全部5种菌株大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌、巴西曲霉和白色念珠菌的有效性,该标准要求在14天不少于自初始计数的2-Log10减少和在28天对细菌没有自14天计数的增加,以及在14和28天对酵母和霉菌没有自初始计数的增加。
表12:0.5%浓度的1940601的菌落计数和Log减少
注释:该测定的检测限是50 CFU/g。在表格中观察到的低于检测限的值被注释为<5.00E+01。
实施例18
配制的合欢属种子提取物和木兰属树皮提取物组合的有效性试验
用非-离子o/w乳液系统(1940602)配制的1A:1M组合在0.1%浓度时,在攻击试验中针对5种菌株大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌、巴西曲霉和白色念珠菌的抗菌活性和功效按照在实施例11中描述的USP <51>指南进一步评价。结果示于图6中。在2、7、14和28天评估存活微生物的数量并基于在时间0观察到的初始浓度计算对数减少,如表13中所示。
这项研究清楚地表明0.1%的这种组合物1940602在第2天开始消除大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌和白色念珠菌。在全部4个接触时间点D2、D7、D14和D28均未观察到细菌生长。对于巴西曲霉,在D2未发现抑制作用,在D2后有改善。Log10减少在D7、D14和D28分别为1.02、0.23和1.33。这项研究清楚地表明这种组合物1940602有效对抗大肠杆菌、铜绿假单胞菌、金黄色葡萄球菌、巴西曲霉和白色念珠菌,并且是通过USP51标准的作为类别2产品的合格的1940602,该标准要求在14天不少于自初始计数的2-Log10减少和在28天对细菌的没有自14天计数的增加,以及在14和28天对酵母和霉菌的没有自初始计数的增加。
表13:0.1%浓度的1940602的菌落计数和Log减少
注释:该测定的检测限是50 CFU/g。在表格中观察到的低于检测限的值被注释为<5.00E+01。
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因此,已公开了用于防腐剂和抗微生物剂的化合物和组合物的具体实施方案和方法,包括公开化合物的立体异构体、药学上或保健上可接受的盐、互变异构体、糖苷和前药以及改善和维持肝脏健康的相关方法。然而,对于本领域技术人员显而易见的是,在不脱离本文的发明构思的情况下,除了已经描述的那些以外,还可以进行更多的修改。因此,本发明的主题不受限制,除了在本文公开的精神范围内。此外,在解释说明书和权利要求书时,所有术语应该以与上下文一致的最宽泛可能的方式解释。具体而言,术语“包括”和“包含”应该被解释为以非排他性方式提及元件、组分或步骤,指示所提及的元件、组分或步骤可以与未明确提及的其它元件、组分或步骤一起存在、利用或组合。
Claims (21)
1.一种组合物,其包含:至少一种合欢属(Albizia)提取物和木兰属(Magnolia)提取物的混合物。
2.权利要求1的组合物,其中所述组合物包含至少一种富集一种或多种大环生物碱的合欢属提取物和至少一种富集一种或多种木脂素的木兰属提取物的混合物。
3.一种包含权利要求1的组合物的食品、化妆品、保健品或药品,其中所述组合物是防腐剂。
4.权利要求3的组合物,其中所述组合物以食品、化妆品、保健品或药品总重量的从约0.001%至约10%重量的范围存在于食品、化妆品、保健品或药品中。
5.权利要求4的组合物,其中所述组合物以食品、化妆品、保健品或药品总重量的从约0.01%至约5%重量的范围存在于食品、化妆品、保健品或药品中。
6.权利要求1的组合物,其中合欢属提取物和木兰属提取物以范围从10:1至1:10的重量比共混。
7.权利要求6的组合物,其中合欢属提取物和木兰属提取物以1:1的重量比共混。
8.权利要求1的组合物,其中合欢属提取物包含约0.01%-99.9%的大环生物碱。
9.权利要求1的组合物,其中木兰属提取物包含约0.01%-99.9%的二酚木脂素。
10. 权利要求1的组合物,其中合欢属选自苦味合欢(Albizia amara)、Albiziaschimperiana、阔荚合欢(Albizia lebbek)、含胶合欢(Albizia gummifera)、Albizziainopinata、雨树(Albizia saman, Samanea saman=Pithecolobium saman), 热非合欢(Albizia adianthifolia)、Albizia adinocephala、灌木合欢(Albizia anthelmintica)、Albizia antunesiana、Albizia chevalieri、天香藤(Albizia corniculata)、白花合欢(Albizia crassiramea)、巧家合欢(Albizia duclouxii)、Albizia glabra、合欢(Albiziajulibrissin)、山合欢(Albizia kalkora)、缅甸合欢(Albizia lebbekoides)、Albiziamyriophylla、Albizia nigricans、香合欢(Albizia odoratissima)、Albiziapeterisana、Albizia poilanei、黄豆树(Albizia procera)、Albizia tanganyicensis、Albizia vialeana Pierre、西非合欢(Albizia zygia)、Aphelandra fuscopunctata、麻黄属(Ephedra spp.)、Verbascum pseudonobile、角蒿(Incarvillea sinensis)、紫毛蕊花(Verbascum phoenicum)、黑毛蕊花(Verbascum nigrum)、布氏大青(Clerodendrumbuchneri)、金脉单药花(Aphelandra squarrosa)或其组合。
11.权利要求2的组合物,其中至少一种富集的合欢属提取物用水、乙醇、甲醇、醇和水-混合溶剂,或通过超临界流体从合欢属植物提取。
12. 权利要求2的组合物,其中从至少一种合欢属提取物分离的生物碱包含布木柴胺A、B、C、D、E、F、G、H、I、J、K,布木柴胺L1、L2、L3、L4、L5、L6,13-去甲布木柴胺K、9-去甲布木柴胺K、1-去甲布木柴胺K、6'-羟基-9-去甲布木柴胺K、6'-羟基布木柴胺K、FelipealbizineA、Felipealbizine B、6′-羟基布木柴胺C、猴耳环碱、原甲碱(Protomethine)、Verbamethine、Verbametrine、Isoverbametrine、Isoverbamethine、Verbamekrine、Isoverbamekrine、Verbascine、Verbacine、Verbasitrine、Verballocine、Isoverbasitrine、Verballoscenine、Isoverbasikrine、N1-(Z)-对-甲氧基肉桂酰buchnerine、Buchnerine、Verbamedine、Verbascenine、Verbascenine、Isoverbamedine、Schweinine、Prelandrine、Incasine B’、Incasine B或其组合。
13.权利要求2的组合物,其中至少一种富集的木兰属提取物用水、乙醇、甲醇、醇和水混合溶剂,或通过超临界流体从木兰属植物提取。
14. 权利要求1的组合物,其中木兰属包含厚朴(Magnolia officinalis)、黄花木兰(Magnolia acuminate)、望春玉兰(Magnolia biondii)、夜香木兰(Magnolia coco)、白玉兰(Magnolia denudate)、望春花(Magnolia fargesii)、泰国木莲(Magnolia garrettii)、广玉兰(Magnolia grandiflora)、大叶木兰(Magnolia henryi)、紫玉兰(Magnolialiliflora)、恒春厚朴(Magnolia kachirachirai)、日本玉兰(Magnolia Kobus)、日本厚朴木兰(Magnolia obovata)、日本辛夷(Magnolia praecocissima)、百合木兰(Magnoliapterocarpa)、塔形木兰(Magnolia pyramidata)、有喙木兰(Magnolia rostrate)、柳叶木兰(Magnolia salicifolia)、天女木兰(Magnolia sieboldii)、二乔木兰(Magnoliasoulangeana)、星花木兰(Magnolia stellate)、弗吉尼亚木兰(Magnolia virginiana)、桦树木质素的降解产物(prod. of degradation of birch lignin)、小花老鼠簕(Acanthusebracteatus)、Aptosimum spinescens、里白葱木(Aralia bipinnata)、巴西松(Araucariaangustifolia)、猴爪杉(Araucaria araucana)、中亚苦蒿(Artemisia absinthium)、尖叶芸香草(Haplophyllum acutifolium)、大叶芸香(Haplophyllum perforatum)、北美鹅掌楸(Liriodendron tulipifera)、海风藤(Krameria cystisoides)、紫苏(Perillafrutescens)、散沫花(Lawsonia inermis)、肉豆蔻(Myristica fragrans) (nutmeg))、云南拟单性木兰(Parakmeria yunnanensis) (优选属名木兰属)、日本鳄梨(Perseajaponica)、风藤(Piper futokadsura)、Piper wightii、Rollinia mucosa、台湾檫木(Sassafras randaiense)、Scrophularia albida-colchica、瑞香狼毒(Stellerachamaejasme)、关东丁香(Syringa velutina)、海南蒲桃(Syzygium cumini)、Talaumagloriensis、Virola elongate、Urbanodendron verrucosum、Wikstroemia sikokiana或其组合。
15. 权利要求2的组合物,其中从至少一种木兰属提取物分离的木脂素包含厚朴酚、和厚朴酚、望春玉兰脂素A、2,3-双(4-羟基-3-甲氧基苯基)-2-丙烯醛、Denudadione C、丁香厚朴酚、8-[2-羟基-5-(2-丙烯基)苯基]-6-(2-丙烯基)-2H-1-苯并吡喃-2-酮、Denudanolide C、Denudanolide D、Denudanolide B、Denudanolide A、Denudatin A、Denudatin B;(+)-形式,4-羟基-6'-甲氧基-3,3'-双木酚(biligna)-7,7'-二烯-9,9'-二醛、4'-甲氧基厚朴二醛、5,5'-二-2-丙烯基-[1,1'-联苯基]-2,2'-二醇、2,2'-二胡椒酚、FEMA 4559、5,5'-二烯丙基-2,2'-二羟基联苯、冰片基厚朴酚、5,5'-二烯丙基-2-(3-甲基-2-丁烯氧基)联苯基-2'-醇、5,5'-二烯丙基-2-(烯丙氧基)联苯基-2'-醇、3',5-二烯丙基-2,4'-二羟基联苯、3',5-二-2-丙烯基-2,4'-联苯基二醇、5-烯丙基-3'-(1-丙烯基)联苯基-2,4'-二醇、3'-(1-丙烯基)-5-(2-丙烯基)-2,4'-联苯基二醇、3',5-二烯丙基-2-羟基-4'-甲氧基联苯、4'-O-甲基和厚朴酚、2-羟基-4'-甲氧基-3',5-二-2-丙烯基联苯、4,4'-二烯丙基-2,3'-二羟基二苯基醚、2-[3-羟基-4-(2-丙烯基)苯氧基]-5-(2-丙烯基)苯酚、2-羟基-3-甲氧基-4',5-二-2-丙烯基二苯基醚、4',5-二烯丙基-2-羟基-3-甲氧基二苯基醚、2-甲氧基-4-(2-丙烯基)-6-[4-(2-丙烯基)苯氧基]苯酚、辛夷脂素(Fargesin)、辛夷脂素(Methyl pluviatilol)、3,4-二甲氧基-3',4'-亚甲二氧基-7,9':7',9-双环氧木脂素、Kobusin、去甲氧基刚果荜澄茄脂素(Desmethoxyaschantin)、O-甲基薄荷醇、Spinescin、(+)-辛夷脂素、Planinin、辛夷脂素(Methyl pluviatilol)、云南拟单性木兰素A(parakmerin A)、6-烯丙基-7-(3,4-二甲氧基苯基)-2,3-二甲氧基-8-甲基三环[4.2.0.02 ,8]辛-3-烯-5-酮、木兰沙灵(Magnosalin)、双辣薄荷基厚朴酚、Kachirachirol B、粗毛淫羊藿苷(Acuminatin)、利卡灵D、eudeshonokiol A、Eudesmagnolol、桉脂素(Eudesmin);(+)-形式、(+)-表桉叶明(Epieudesmin)、(-)-表桉叶明、Kachirachirol A、Eupomatenoid 13、Fargesiphenol B、Fargesiphenol C、Fargesone A、Fargesone B、4,5-二甲氧基-3',4'-亚甲二氧基-2,7'-二氧代-5,8'-木酚(ligna)-3,6,8-三烯、4-(1,3-苯并间二氧杂环戊烯-5-基)-2,3,4,5-四氢-7-甲氧基-5-甲基-8H-2,5a-亚甲基-1-苯并氧杂环庚三烯-8-酮、苯丙木质素(Garrettilignan) A、苯丙木质素B、四氢-4-(3-羟基-4,5-二甲氧基苯基)-1H,3H-呋喃并[3,4-c]呋喃-1-酮、卡奇醇(Kachiranol)、7',9-二羟基-3,3',4,4',5-五甲氧基-7,9'-环氧木脂素、Magnone B、3,3',4,4',5,9-六甲氧基-7,9'-环氧木脂素-7'-酮、Magnolenin C、3',4,7,9,9'-五羟基-3,5'-二甲氧基-8,4'-氧基新木脂素、3,3'-二甲氧基-4,5:4',5'-双(亚甲二氧基)pyramidatin、3'-羟基-3,4,4',5,5'-五甲氧基pyramidatin、pyramidatin B、3,3',4',5'-四甲氧基-4,5-亚甲二氧基pyramidatin、3,3',4,4',5,5'-六甲氧基pyramidatin、pyramidatin C、pyramidatin、pyramidatin D、3-羟基-3',4,4',5,5'-五甲氧基pyramidatin、pyramidatin A、3-羟基-3',4,5-三甲氧基-4',5'-亚甲二氧基pyramidatin、pyramidatin F、pyramidatin G、pyramidatin H、pyramidatinE、5'-羟基-3,3',4,4',5-五甲氧基pyramidatin、Magnoshinin、2',3,4,4',5,6-六甲氧基-2,7'-环木酚(lign)-7-烯、Acanthoside B、Eleutheroside E1、3-羟基-3',4,4',5,5'-五甲氧基-7,9':7',9-双环氧木脂素、(+)-Episyringaresinol、Lirioresinol A、Symplicosigenol、Kobusinol B、Fargesol、9-O-Acetylfargesol、Magnolone、BiondininB、Biondinin E、Magnone A、7,9,9'-三羟基-3,3',4-三甲氧基-8,4'-氧基新木脂素、赤式、苏式、Magnovatin A、Magnovatin B、Oleiferin C、3,4:3',4'-双(亚甲二氧基)-7-木脂素醇、7-羟基-3,4:3',4'-双(亚甲二氧基)木脂素、Liliflodione、Denudadione B、Denudadione A、Liliflol A、Liliflol B、Denudatone、3-[2',6-二羟基-5'-(2-丙烯基)[1,1'-联苯基-3-yl]]-2-丙烯醛、Randainal、厚朴醛B、厚朴醛C、6'-O-甲基厚朴醛B、4-脱氧-6-甲氧基厚朴醛A、4-甲氧基厚朴醛B (不恰当的)、2',6-二羟基-5'-(2-丙烯基) [1,1'-联苯基]-3-甲醛、5-烯丙基-5'-甲酰基-2,2'-二羟基联苯、厚朴醛E、6-O-甲基厚朴醛E、9-羟基-3,3',4,4',5-五甲氧基-7,9'-环氧木酚-7'-烯、9,9'-二羟基-3,3',4,4',5-五甲氧基-2,7'-环木酚-7-烯、Magnolianin、Magnolignan I、Magnolignan B、Magnolignan A、Magnolignan D、Magnolignan C 6'-葡糖苷、Magnolignan C、Magnolignan E、MagnolignanF、Magnolignan G、Magnolignan H、2-[4-羟基-3-(2-丙烯基)苯基]-2,5-环己二烯-1,4-二酮、2-(3-烯丙基-4-羟基苯基)-1,4-苯醌、Magnosalicin; (7RS,7'SR,8RS,8'RS)-形式、Magnostellin B、Magnostellin B; 7,9-二差向异构体、5-甲氧基,5-[2-羟基-5-(2-丙烯基)苯基]-2-甲基苯并呋喃、3-羟基-3',4,4',5-四甲氧基-7,9',7',9-双环氧木脂素、3-De-O-methylmagnolin、Magnolin、3-O-Demethylaschantin、3'-O-Demethylaschantin、3-羟基-4,5-二甲氧基-3',4'-亚甲二氧基-7,9':7',9-双环氧木脂素、5'-羟基-4'-O-甲基薄荷醇、Epimagnolin A、7'-羟基-3,3',4,4'-四甲氧基-7,9'-环氧木脂素、Magnostellin A、Kobusinol A、4,7'-二羟基-3,3',4'-三甲氧基-7,9'-环氧木脂素、4',5,9-三羟基-3,3'-二甲氧基-7,9'-环氧木脂素、Fargesiphenol A、Liliflone、单萜烯基厚朴酚、辣薄荷基和厚朴酚、单萜烯基和厚朴酚、Saulangianin I、Sesamin; (-)-形式、Syringinoside、Syringin 4''-葡糖苷、3,3',4,5'-四甲氧基-7,9':7',9-双环氧木脂素、3',5'-二甲氧基-3,4-亚甲二氧基-7,9':7',9-双环氧木脂素、Galgravin、2,2'-二羟基-3-甲氧基-5,5'-二-2-丙烯基联苯、3-甲氧基厚朴酚、5,5'-二烯丙基-2,2'-二羟基-3-甲氧基联苯基或其组合。
16.权利要求1的组合物,其中组合物包含:
至少一种来自植物材料或其它来源的合欢属提取物,和至少一种来自植物材料或另一种来源的木兰属提取物的混合物,
其中至少一种合欢属提取物与植物材料或其它来源的至少一种合欢属提取物中的一种或多种大环生物碱的量或活性比较,具有一种或多种大环生物碱的量或活性的增加,和
其中至少一种木兰属提取物与植物材料或其它来源的至少一种木兰属提取物中的一种或多种木脂素的量或活性比较,具有一种或多种木脂素的量或活性的增加。
17.权利要求16的组合物,其中植物材料或其它来源包括茎、茎皮、树干、树干皮、树枝、块茎、根、根皮、嫩芽、种子、根状茎、花和其它生殖器官、组织培养物和干细胞培养物、叶和其它气生部分或其组合。
18. 权利要求1的组合物,其中组合物另外地包含至少一种已知的抗微生物成分、其中所述成分包含补骨脂(Psoralea corylifolia)、姜黄素(Curcumin)、丁香酚(Eugenol)、高良姜(Alpinia galganga)、黄连(coptidis)、印度苦楝(Azadirachta indica)、蜂胶(Propolis)、丁香油、苦参(Sophora flavescens)、槟榔(Areca catechu)、洋甘草(Glycyrrhiza glabra L.)、北美乔柏(Thuja plicata)、黄柏(Cortex phellodendri)、大黄(Rheum palate)、小良姜(Alpinia officinarum)、姜黄(Curcuma longa)、构树(Broussonetia papyriferra)、黄栌叶荚蒾(Viburnum cotinifolium)、大飞扬草(Euphorbia hirta Linn)、黄荆(Vitex negundo),或其组合的植物粉末或植物提取物。
19. 权利要求1的组合物,其中所述组合物还包含至少一种已知的抗微生物成分、其中所述成分包括丙酸钙、苯甲酸钠、硝酸钠、亚硝酸钠、山梨酸钾、苯甲酸、水杨酸、山梨酸、醇、苯氧基乙醇、1,2-二醇(1,2-丙二醇、1,2-丁二醇、1,2-戊二醇、1,2-己二醇)、1,3-二醇(1,3-丙二醇、1,3-丁二醇、1,3-戊二醇、1,3-己二醇)、1,5-戊二醇、苯扎氯铵、对羟基苯甲酸酯、亚硫酸盐(二氧化硫、亚硫酸氢钠、亚硫酸氢钾等)和EDTA二钠,和BHT (丁羟甲苯)和BHA(丁羟茴醚)、甲醛(通常在溶液中)、戊二醛(杀死昆虫),和甲基氯异噻唑啉酮。
20. 权利要求1的组合物,其中所述组合物还包含药学上或保健上可接受的载体、稀释剂,或赋形剂,其中药物或保健制剂包含从约0.001%重量(wt%)至约10 wt%的提取物混合物的活性成分。
21.权利要求1的组合物,其中组合物被配制为片剂、硬胶囊、软胶囊、粉剂、颗粒剂、液体剂、酊剂、sashay、即饮饮料单剂,或锭剂、化妆品膏、凝胶、洗剂、洗发剂、护发素、身体清洗剂、身体洗剂、染发剂、肤色剂、眼睛颜色剂、唇膏、香水、牙膏、漱口液、果汁、芦荟汁、酸奶、食品、软饮料、饮料、加工水果、奶酪产品、酒、松饼、花生酱、RTD、蛋白棒或小吃棒。
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CN110668985B (zh) * | 2019-09-20 | 2021-11-23 | 广东省禾基生物科技有限公司 | 厚朴酚衍生物及其制备方法和应用 |
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EP3373946A1 (en) | 2018-09-19 |
KR102131332B1 (ko) | 2020-07-07 |
US10780173B2 (en) | 2020-09-22 |
US20170173162A1 (en) | 2017-06-22 |
JP7487150B2 (ja) | 2024-05-20 |
KR20220129103A (ko) | 2022-09-22 |
JP6903656B2 (ja) | 2021-07-14 |
JP2024045242A (ja) | 2024-04-02 |
HK1256611A1 (zh) | 2019-09-27 |
KR102443442B1 (ko) | 2022-09-14 |
KR20180083353A (ko) | 2018-07-20 |
WO2017083363A9 (en) | 2017-07-13 |
KR20200083673A (ko) | 2020-07-08 |
JP2018536402A (ja) | 2018-12-13 |
JP2021168656A (ja) | 2021-10-28 |
WO2017083363A1 (en) | 2017-05-18 |
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