海藻抗肿瘤抗细菌生物活性物质的研究
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摘要
我们系统采集了山东沿海的几十种海藻，建立了细胞毒和抗菌活性筛选模型，对一百多个海藻样品进行了商通量(HTS)活性筛选，发现了几种具有较强生物活性的海藻：小粘膜藻、多管藻、萱藻、海萝、松节藻，酸藻等。并对其中生物量较大的松节藻、萱藻进行了先导化合物的分离纯化和结构鉴定，从中分离纯化出色素、甾醇、甘油酯和溴酚类化合物30多个，并运用一维核磁共振(~1HNMR、~(13)CNMR、DEPT)、二维核磁共振(~1H-~1Hcosy、HMBC、HMQC)、红外光谱(IR)、质谱(EI/MS、FAB/MS)等现代波谱分析技术分析鉴定了化合物15个，其中15个为新化合物，1个为首次从自然界中分离得到。运用MTT法对所分离的化合物进行了细胞毒活性的检测，得到了9个有选择性细胞毒活性的化合物。
对近四年来海洋抗肿瘤药物的研究现状和大型海藻天然产物的研究现状进行了简要的综述。概述了近年来世界各国的海藻抗肿瘤筛选方面的工作进展；总结了近年来从蓝藻、甲藻、红藻、褐藻、绿藻中分离的活性化合物，其中包括已经进入临床研究阶段的Scytophycin、Halomon、Cryptophycin、Malyngamide、Tolytoxin等。综述了近四年来从大型海藻中分离的约100年天然化合物，其中大部分具有重要的生物活性。
以采自山东沿海的39种海藻的96个样品为材料，进行了较系统的抗肿瘤生物活性的筛选，共发现了8种有选择性抗肿瘤活性的海藻，它们是红藻门的鸭毛藻(Symphyocladia latiuscula)、松节藻(Rhodomela confervoides)、多管藻(Polysiphonia urcedata)、海萝(Gloiopellis furcata)，褐藻门的小粘膜藻(Leathesia difformes)、萱藻(Scytosiphon lomentarius)、点叶菜(Punctaria latifolia)、叉开网翼藻(Dictyopteris divaricata)。其中多管藻的酒精、氯仿提取物，萱藻的酒精提取物，叉开网翼藻的正已烷提取物对人口腔上皮鳞癌KB细胞具有强选择性活性，它们的IC_(50)均小于4.40μg/ml。萱藻的酒精提取物还对HT-29肿瘤细胞具有很细的选择性活性，其IC_(50)=1.49μg/ml
运用薄层层析方法对10种海藻提取物的抗金黄色葡萄球菌和大肠杆菌活性进行了研究，发现褐藻提取物的抗菌活性最高，红藻的抗菌活性较低，而绿藻
沟拢抗肿痈抗圳肉丫物恬付物顶的叽穴
I”川h个几丁没行沽州：。红藻门的松节藻、帅毛藻I］“·定的沂叮。灿纵］的肋妊
和沏黍］”沂叮较高。酸藻和海黍子的3 个强仇涮R性带对久负色渐萄球物f！（］抑
泊阳川？分别为33；nm、门＊m和门．5 m；们，酸藻水相的2个沂V叫们中能抑M人
肠什峋，f帅川岗圈0径分别为21＊m和16；1。；n。
村山乐沿海分介量较大的两种海藻进h‘了光导化合物的分离纯化和乡’个J鉴
人n几以计藻为村例进行了先导化合物分肉条件的模索，从小分离纯化了卜多
个化广叫扣，分别属厂色素、＊醇、脂肋酸和什川！酯类物质，c鉴定川2 个化八
物：卜水来二 隶（oA3R｝p，p一＊＊r川e。1e一3”．3一＊ 且）平1六藻手地mooskr（。10 ＊松
竹i们川上厂儿V化合物的分离纯化，从一丫Kul7个化合物，凸鉴定了14个，
且 十 5 个为新化合物，分别足3七roffiO－4，5－his（2、3－LlbO（；1ilo－4、5．
。Illlydl·OXyhCllZyl）l，2－bCflZCflCdOll（X叉12（））、3－bfolllO－4－［2．3－dibOOlll（。－4．5－
。Illl＼。11·（。（VPlllllylllllltlly－5－（11ydl”OXyXlltll＼，I）1，2－hlllllllld（）11（XllZI）、2－1111III＼l－
3（2、3－dlhlolllO－4，5－dlllydtOXy）－PXOPyloldollydl（XIJ26）、2－11tllyl－3（2、3－dlbl（）。11O－
4、5－dlllydl‘oxy）－propllal methyl henllacetal（X【号28）、3－bromo－4－［2、3－dibrolllo－4、5－
。11llVdl·OXV…11llyllllltllyl－5－（lthOXyXXtllyl）－1、2－bll。ZZZZdoil（XU29），））‘个化 八物
工吕I·：，111X和一4、多一山！lydl·：｝Xy一卜XlllolC CCId ill区叫 1。Ill·（xN25）为汁次从rI然W 吾讣风
川士山门．
X上八放不时公H藻中得至帅勺纯化合物利以它粕提物进订了纠恻对入〔们；【’山价
测、纠以分闪管藻小有＊个且羽IB卜15！叼个纯化土物具丫IW较强的选抒什纠HM衍5．厂
川－；松V热小订7 个纯化合物（＊川6、X［门8、XU22、m记4、＊U二5、川口6、
X【］二8）H何 回定的选抒件细胞得活州－。：冻xt门8外的6个化穴物刑以何村KB
训1地们5人汁，化合物XU16、XU24、xU25 s人选抒性刊收u 8d74口2和AS的肿
爪Z纠川过！’山作川。
Tens of algae along Shandong coast were collected, and their cytotoxic and antibacterial activities were screened with high throughout screening methods (UTS). As a result, some algae with high activities against tumor cells or bacteria were found. The algae were Leathesia difformes, Polysiphonia urcedala, Scytosiphon lomentarius. Ciloiopcliis furcctla, Rhodomela confervoides etc. The work of isolating, purifying and identifying new leading compounds from Rhodomela confervoides and Scylosiphon lomcnkirins were completed. More than 30 compounds were isolated from them, among which 15 were identified by the combination of IR. MS, and ID. 2D NMR modern spectrum methods. There were 5 new compounds and 1 pure natural compound among the 15 compounds. Furthermore, the cytotoxic activities of these compounds were fulfilled by MTT method, and 9 of them were found to be with selective cytotoxic activities.
The recent development of marine antitumor drugs and natural products from macroalgae were briefly reviewed. The studies of antitumor screening in recent years were covered. The bioactive substances in blue algae, dinoflagellate. red algae, brown algae and green algae were summarized, some of them had been applied to preclinic study, such as Scytophycin. Ilalomon, Cryptophycin. Malyngamide and Tolytoxin. About 100 natural products newly isolated from macroalgae in recent four years were also covered, almost all of which showed significant activities.
The antitumor activity screening of 96 crude extracts of 39 species of algae was enclosed. Fight species including Symphyocludiii laliuscula. Rhodomela confervoides. I'olvsiphonia urcedala, Gloiopellis furcald. Leathesia difformes, Scylosiphon lomenlarius, Punctcirid latifolia and Diclyopleris divaricala showed potent selectively anlincoplastic activities. The ethanol and chloroform extracts of Polysiphonia nrccc/diii. the ethanol extracts of Scylosiphon lomenlarius and the hexane extracts of Dictyopteris divaricala all showed powerful selectively cytotoxic activities, and their IC50 were less than 4.40 ug/ml. The ethanol extracts of Scylosiphon lomenlarius had also showed strong activities against HT-29 tumor cell, and the IC50 was 1.49 ug/ml.
Thin layer chrotnatography (TLC) method was used to study the antibacterial activities against two kinds of bacteria, Excherichifi coli and Sltiphylococcus aureris. The activities of five seaweed extracts were detected, of which brown algae displayed the highest activities. Three bands from Desmiirestiu viridis and Sargassum kjelimanianum(Phaeophyta) exhibited powerful activities against Siaphylococaix utiivnx, the diameter of inhibition cycle was 33mm. 17mm and 17.5 mm. respectively. Two bands from Desmareslia viridix could inhibit the growth of Excherichici coli vigorously. The higher activity was detected in red algae. In comparision with browm and red algae, the activities of green algae were almost negligible.
Two species of marine algae, Seytosiphon lomentarius and Rhodomela confervoides. were used to isolate and purify new leading compounds from them. More than ten compounds were isolated from Scvloxiphon lomentarius and identified as pigments, sterols, fatty acids and glycerides. Among them two were identified as (3R,3R')-p p-carotene-3 ,3-diol and fucosterol. respectively. Seventeen compounds were isolated from Rhodomela confervoidc and 14 were identified. Among them. 5 compounds. 3-bromo-4.5-bis(2,3-dibromo-4.5-dihydroxyben7.yl)1.2-ben7,enedoil (Xt'20). 3-broino-4-[2,3-dibromo-4,5-dihydroxyphenyl] methyl-5-(hydroxymethyl) 1,2-bcn/enedoil (XU21). 2-methyl-3(2.3-dibromo-4,5-dihydroxy)-propylaldehyde (XI126). 2-methyl-3
(2,3-dibromo-4,5-dihydroxy)-propnal methyl hemiacetal(XU28). 3-bromo-4-|2,3-dibromo-4,5-dihydroxyphenvl]methyl-5-(ethoxymethyl)-l. 2-ben/ene -doil (XU29). were all new. Another compound. 3-bromo-4.5-dihydroxy-ben/.oic acid methyl ester was isolated from natural resources for the first time.
The cyloloxic results of all purified compounds and some crude extracts were reported. Two purified compounds D4-
对近四年来海洋抗肿瘤药物的研究现状和大型海藻天然产物的研究现状进行了简要的综述。概述了近年来世界各国的海藻抗肿瘤筛选方面的工作进展；总结了近年来从蓝藻、甲藻、红藻、褐藻、绿藻中分离的活性化合物，其中包括已经进入临床研究阶段的Scytophycin、Halomon、Cryptophycin、Malyngamide、Tolytoxin等。综述了近四年来从大型海藻中分离的约100年天然化合物，其中大部分具有重要的生物活性。
以采自山东沿海的39种海藻的96个样品为材料，进行了较系统的抗肿瘤生物活性的筛选，共发现了8种有选择性抗肿瘤活性的海藻，它们是红藻门的鸭毛藻(Symphyocladia latiuscula)、松节藻(Rhodomela confervoides)、多管藻(Polysiphonia urcedata)、海萝(Gloiopellis furcata)，褐藻门的小粘膜藻(Leathesia difformes)、萱藻(Scytosiphon lomentarius)、点叶菜(Punctaria latifolia)、叉开网翼藻(Dictyopteris divaricata)。其中多管藻的酒精、氯仿提取物，萱藻的酒精提取物，叉开网翼藻的正已烷提取物对人口腔上皮鳞癌KB细胞具有强选择性活性，它们的IC_(50)均小于4.40μg/ml。萱藻的酒精提取物还对HT-29肿瘤细胞具有很细的选择性活性，其IC_(50)=1.49μg/ml
运用薄层层析方法对10种海藻提取物的抗金黄色葡萄球菌和大肠杆菌活性进行了研究，发现褐藻提取物的抗菌活性最高，红藻的抗菌活性较低，而绿藻
沟拢抗肿痈抗圳肉丫物恬付物顶的叽穴
I”川h个几丁没行沽州：。红藻门的松节藻、帅毛藻I］“·定的沂叮。灿纵］的肋妊
和沏黍］”沂叮较高。酸藻和海黍子的3 个强仇涮R性带对久负色渐萄球物f！（］抑
泊阳川？分别为33；nm、门＊m和门．5 m；们，酸藻水相的2个沂V叫们中能抑M人
肠什峋，f帅川岗圈0径分别为21＊m和16；1。；n。
村山乐沿海分介量较大的两种海藻进h‘了光导化合物的分离纯化和乡’个J鉴
人n几以计藻为村例进行了先导化合物分肉条件的模索，从小分离纯化了卜多
个化广叫扣，分别属厂色素、＊醇、脂肋酸和什川！酯类物质，c鉴定川2 个化八
物：卜水来二 隶（oA3R｝p，p一＊＊r川e。1e一3”．3一＊ 且）平1六藻手地mooskr（。10 ＊松
竹i们川上厂儿V化合物的分离纯化，从一丫Kul7个化合物，凸鉴定了14个，
且 十 5 个为新化合物，分别足3七roffiO－4，5－his（2、3－LlbO（；1ilo－4、5．
。Illlydl·OXyhCllZyl）l，2－bCflZCflCdOll（X叉12（））、3－bfolllO－4－［2．3－dibOOlll（。－4．5－
。Illl＼。11·（。（VPlllllylllllltlly－5－（11ydl”OXyXlltll＼，I）1，2－hlllllllld（）11（XllZI）、2－1111III＼l－
3（2、3－dlhlolllO－4，5－dlllydtOXy）－PXOPyloldollydl（XIJ26）、2－11tllyl－3（2、3－dlbl（）。11O－
4、5－dlllydl‘oxy）－propllal methyl henllacetal（X【号28）、3－bromo－4－［2、3－dibrolllo－4、5－
。11llVdl·OXV…11llyllllltllyl－5－（lthOXyXXtllyl）－1、2－bll。ZZZZdoil（XU29），））‘个化 八物
工吕I·：，111X和一4、多一山！lydl·：｝Xy一卜XlllolC CCId ill区叫 1。Ill·（xN25）为汁次从rI然W 吾讣风
川士山门．
X上八放不时公H藻中得至帅勺纯化合物利以它粕提物进订了纠恻对入〔们；【’山价
测、纠以分闪管藻小有＊个且羽IB卜15！叼个纯化土物具丫IW较强的选抒什纠HM衍5．厂
川－；松V热小订7 个纯化合物（＊川6、X［门8、XU22、m记4、＊U二5、川口6、
X【］二8）H何 回定的选抒件细胞得活州－。：冻xt门8外的6个化穴物刑以何村KB
训1地们5人汁，化合物XU16、XU24、xU25 s人选抒性刊收u 8d74口2和AS的肿
爪Z纠川过！’山作川。
Tens of algae along Shandong coast were collected, and their cytotoxic and antibacterial activities were screened with high throughout screening methods (UTS). As a result, some algae with high activities against tumor cells or bacteria were found. The algae were Leathesia difformes, Polysiphonia urcedala, Scytosiphon lomentarius. Ciloiopcliis furcctla, Rhodomela confervoides etc. The work of isolating, purifying and identifying new leading compounds from Rhodomela confervoides and Scylosiphon lomcnkirins were completed. More than 30 compounds were isolated from them, among which 15 were identified by the combination of IR. MS, and ID. 2D NMR modern spectrum methods. There were 5 new compounds and 1 pure natural compound among the 15 compounds. Furthermore, the cytotoxic activities of these compounds were fulfilled by MTT method, and 9 of them were found to be with selective cytotoxic activities.
The recent development of marine antitumor drugs and natural products from macroalgae were briefly reviewed. The studies of antitumor screening in recent years were covered. The bioactive substances in blue algae, dinoflagellate. red algae, brown algae and green algae were summarized, some of them had been applied to preclinic study, such as Scytophycin. Ilalomon, Cryptophycin. Malyngamide and Tolytoxin. About 100 natural products newly isolated from macroalgae in recent four years were also covered, almost all of which showed significant activities.
The antitumor activity screening of 96 crude extracts of 39 species of algae was enclosed. Fight species including Symphyocludiii laliuscula. Rhodomela confervoides. I'olvsiphonia urcedala, Gloiopellis furcald. Leathesia difformes, Scylosiphon lomenlarius, Punctcirid latifolia and Diclyopleris divaricala showed potent selectively anlincoplastic activities. The ethanol and chloroform extracts of Polysiphonia nrccc/diii. the ethanol extracts of Scylosiphon lomenlarius and the hexane extracts of Dictyopteris divaricala all showed powerful selectively cytotoxic activities, and their IC50 were less than 4.40 ug/ml. The ethanol extracts of Scylosiphon lomenlarius had also showed strong activities against HT-29 tumor cell, and the IC50 was 1.49 ug/ml.
Thin layer chrotnatography (TLC) method was used to study the antibacterial activities against two kinds of bacteria, Excherichifi coli and Sltiphylococcus aureris. The activities of five seaweed extracts were detected, of which brown algae displayed the highest activities. Three bands from Desmiirestiu viridis and Sargassum kjelimanianum(Phaeophyta) exhibited powerful activities against Siaphylococaix utiivnx, the diameter of inhibition cycle was 33mm. 17mm and 17.5 mm. respectively. Two bands from Desmareslia viridix could inhibit the growth of Excherichici coli vigorously. The higher activity was detected in red algae. In comparision with browm and red algae, the activities of green algae were almost negligible.
Two species of marine algae, Seytosiphon lomentarius and Rhodomela confervoides. were used to isolate and purify new leading compounds from them. More than ten compounds were isolated from Scvloxiphon lomentarius and identified as pigments, sterols, fatty acids and glycerides. Among them two were identified as (3R,3R')-p p-carotene-3 ,3-diol and fucosterol. respectively. Seventeen compounds were isolated from Rhodomela confervoidc and 14 were identified. Among them. 5 compounds. 3-bromo-4.5-bis(2,3-dibromo-4.5-dihydroxyben7.yl)1.2-ben7,enedoil (Xt'20). 3-broino-4-[2,3-dibromo-4,5-dihydroxyphenyl] methyl-5-(hydroxymethyl) 1,2-bcn/enedoil (XU21). 2-methyl-3(2.3-dibromo-4,5-dihydroxy)-propylaldehyde (XI126). 2-methyl-3
(2,3-dibromo-4,5-dihydroxy)-propnal methyl hemiacetal(XU28). 3-bromo-4-|2,3-dibromo-4,5-dihydroxyphenvl]methyl-5-(ethoxymethyl)-l. 2-ben/ene -doil (XU29). were all new. Another compound. 3-bromo-4.5-dihydroxy-ben/.oic acid methyl ester was isolated from natural resources for the first time.
The cyloloxic results of all purified compounds and some crude extracts were reported. Two purified compounds D4-
引文
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