全 文 :研究论文· A RTICLE
Marine Sciences/ Vo l.32 , No.11/ 2008
鸭毛藻内生真菌 Hypocreales sp.的化学成分研究
李冬利1 , 2 ,李晓明1 ,崔传明1 ,王斌贵1
(1.中国科学院 海洋研究所 实验海洋生物学重点实验室 ,山东 青岛 266071;2.中国科学院 研究生院 ,北京
100049)
摘要:从采自大连近海的红藻鸭毛藻(S ym phyocladia latiuscula)中分离到一株肉座菌目真菌(H ypocreales
sp.),对其发酵代谢产物的化学成分进行了研究。利用正相硅胶柱层析 、葡聚糖凝胶 Sephadex LH-20 柱层
析 、制备薄层层析(PT LC)以及重结晶等分离手段 , 并通过一维 、二维核磁共振技术 、质谱技术等从该菌发酵
液中分离鉴定了 10 个化合物:双酚 A(1);邻羟基苯甲酸(2);吲哚甲酸(3);吲哚乙酸(4);N-乙酰色胺(5);
(22E , 24R)-麦角甾-7 , 9 , 22-三烯-3β-醇(6);过氧化麦角甾醇(7);(22E , 24R)-5α, 6α-环氧麦角甾-8 , 22-二烯-
3β , 7α-二醇(8);(22E , 24R)-麦角甾-7 , 22-二烯-6β-甲氧基-3β , 5α-二醇(9);啤酒甾醇(10)。这些化合物均为首
次从该菌中分离得到 ,其中化合物 1 为首次作为天然产物分离得到。
关键词:鸭毛藻(Symphyocladia latiuscula);内生真菌;肉座菌;化学成分
中图分类号:Q58 文献标识码:A 文章编号:1000-3096(2008)11-0051-05
所谓内生真菌(Endophyt ic fungus)是指内共生
在宿主体内 ,但不至引起明显症状的一类真菌 ,其与
宿主之间存在着相互依赖的互利共生关系[ 1] 。在与
宿主共生与进化的相互作用过程中可产生丰富的具
有生物活性的次生代谢产物 ,因此成为天然活性物
质的重要来源[ 2] 。同时内生真菌具有生长周期短 ,
代谢易于调控 ,可通过发酵实现大规模生产的特点 ,
因此内生真菌的活性代谢产物用于新药的研究开
发 ,不仅前景广阔 ,而且有利于将来实现产业化。内
生真菌不仅分布于陆地环境中 ,也广泛分布于各种
海洋生物 ,如海绵 、海藻 、红树林以及软体动物等[ 3] 。
近年来对于海藻来源的内生真菌次级代谢产物的研
究报道越来越多[ 3 ~ 5] ,本研究组也曾报道过一些海藻
来源的内生真菌的次级代谢产物的研究[ 6 ~ 11] 。作者
从采自大连近海的红藻鸭毛藻(S ymphyocladia
lat iuscula)中分离到的一株肉座菌目真菌(Hypoc-
reales sp.)的发酵培养物中分离并鉴定了 10 个化合
物的结构。这些化合物均为首次从该菌中分离得
到 ,其中化合物 1为首次作为天然产物分离得到。
1 材料与方法
1.1 材料
1.1.1 菌种
Hypocreales sp.是由本实验室分离自大连近海
采集的鸭毛藻的内生真菌。通过克隆真菌核糖体
rDNA 基因转录间隔序列(I TS1-5.8S-ITS2 全长序
列)、测序并与GenBank中已知真菌菌株相应序列比
对结果鉴定为肉座菌目真菌(Hypocreales sp.)。
1.1.2 菌种培养
菌种以琼脂-麦芽膏培养基 ,4℃保存 。发酵培养
基为酵母膏 3 g/ L ,麦芽糖 20 g/L ,山梨醇 20 g/ L ,
味精 10 g/ L , 色氨酸 0.5 g/L , KH 2 PO 4 0.5 g/ L ,
MgSO 4 ·7H 2O 0.3 g/ L ,pH 6.5。1 000 mL 三角烧
瓶 ,每瓶装液体培养基 300 mL ,115℃灭菌 20 min后
接种。共接种液体培养基 30 L ,室温培养 30 d ,过
滤 ,分别收集菌丝体和发酵液。
1.2 仪器与试剂
SGW X-4 显微熔点仪(温度未校正);Bruker
Avance 500 MHz 核磁共振仪 , TMS 内标;VG Au-
toSpec 3000型质谱仪;薄层色谱硅胶 GF254和柱色
谱硅胶(200 ~ 300目)为青岛海洋化工厂分厂产品;
显色剂为茴香醛硫酸溶液;所用有机溶剂为重蒸的
工业级溶剂 。
收稿日期:2008-02-20;修回日期:2008-06-10
基金项目:国家自然科学基金项目(30530080);山东省科技发展计划
项目(2006GG2205023);海洋药物教育部重点实验室开放基金项目
[ KLMD(OUC)2004]
作者简介:李冬利(1980-),女 ,博士 ,湖南耒阳人 ,主要从事天然产物
化学研究 ,电话:0532-82898890 , E-mail:yichen802003@yah oo.com.
cn;王斌贵 , 通讯作者 , 电话:0532-82898553 , E-mai l:w angbg @ms.
qdio.ac.cn
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海洋科学/ 2008 年/第 32 卷/第 11 期
1.3 提取分离
收集发酵液约 30 L ,用乙酸乙酯提取。菌丝体
粉碎后用甲醇提取。提取物经薄层层析检测结果相
似。合并两部分提取物进行硅胶柱层析 ,以石油醚-
乙酸乙酯(100∶0 ~ 0∶100)系统梯度洗脱 ,分为 7
个组分 Ⅰ ~ Ⅶ ,其中组分 Ⅲ经 Sephadex LH-20(氯
仿∶甲醇为 1∶1)凝胶柱层析得化合物 1(149.0
mg);组分 Ⅱ经 Sephadex LH-20(氯仿:甲醇为 1∶
1)凝胶柱层析得化合物 2(201.0 mg);组分 Ⅴ经
Sephadex LH-20(甲醇)凝胶柱层析和制备型薄层层
析得化合物 3(3.9 mg)和化合物 4(4.5 mg);组分 Ⅶ
经 Sephadex LH-20(氯仿∶甲醇=1∶1)凝胶柱层
析和制备型薄层层析得化合物 5(4.1 mg)、化合物 8
(4.7 mg)和化合物 10(9.6 mg);组分 Ⅰ进一步重结
晶得化合物 6(26.0 mg);组分Ⅳ经 Sephadex LH-20
(氯仿:甲醇为 1∶1)凝胶柱层析和制备型薄层层析
得化合物7(77.4 mg);组分Ⅵ经Sephadex LH-20(甲醇)
凝胶柱层析和制备型薄层层析得化合物9(10.7 mg)。
图 1 化合物 1 ~ 10 的结构
F ig.1 Structures of compounds 1~ 10
2 化合物结构鉴定
化合物 1:黄色油状物;EIM S 给出分子离子峰
228 以及失去一个甲基的碎片峰 213;1 H-NM R
(CDCl3)δ1.62(6H , s , H-1/3), 7.09(4H , d , J =8.5
Hz ,H-2′/6′),6.73(4H , d , J =8.5 Hz , H-3′/5′);表
明结构中存在对位取代的苯环及与季碳相连的甲
基。13 C-NMR(CDCl3)31.1(C-1/3), 41.7(C-2),
143.3(C-1′), 127.9(C-2′/6′), 114.7(C-3′/5′),
153.4(C-4′);HMBC 谱显示δ1.62(H-1/3)与δ31.1
(C-1/3),41.7(C-2), 127.9(C-2′/6′)存在相关。由
质谱数据和核磁数据结合推断出该化合物为对称结
构 ,2 ,2-双(4-羟基苯基)丙烷即双酚 A 。该化合物是
一种重要的工业原料 ,由苯酚和丙酮合成[ 12] 。作者
首次作为天然产物分离得到双酚 A 。
化合物 2:无色粉末;EIMS 给出一个失水峰
120;1H-NMR (CDCl3)δ6.67(1H , dd , J =8.5 , 1.6
Hz ,H-3),7.32(1H , dt , J =8.5 , 1.6 Hz ,H-4), 6.69
(1H , dt , J =8.5 , 1.6 Hz , H-5), 7.94(1H , dd , J =
8.5 ,1.6 Hz ,H-6);13 C-NMR(CDCl3)δ109.7(C-1),
151.1(C-2), 116.5(C-3), 135.1(C-4),116.8(C-5),
132.2(C-6), 173.6(C-7);其波谱数据与邻羟基苯甲
酸的文献报道值[ 13] 基本吻合 。
化合物 3:黄色粉末;1 H-NMR(CD3OD)δ7.94
(1H ,d , J =1.4 Hz , H-2), 8.06(1H , d , J =7.9 Hz ,
H-4),7.18(2H ,m ,H-5/6),7.43(1H ,d , J =8.6Hz ,
H-7);13 C-NMR(MeOD)δ133.3(C-2), 108.9(C-3),
122.0(C-4), 123.6(C-5),122.3(C-6), 112.9(C-7),
138.2(C-8), 127.6(C-9),169.2(COOH);其波谱数
据与吲哚甲酸的文献报道值[ 14] 一致。
化合物 4:黄色粉末;1 H-NMR(CD3OD)δ7.15
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Marine Sciences/ Vo l.32 , No.11/ 2008
(1H , s ,H-2), 7.55(1H , d , J =8.0 Hz , H-4), 6.98
(1H , t , J =7.3 Hz , H-5),7.06(1H , t , J =7.2 Hz ,
H-6),7.32(1H , d , J =8.1 Hz , H-7), 3.69(2H , s ,
H-10);13 C-NMR(MeOD)δ124.5(C-2), 109.8
(C-3),119.5(C-4),119.7(C-5),122.3(C-6), 112.1
(C-7),138.1(C-8),128.9(C-9),32.9(C-10), 177.0
(COOH);其波谱数据与吲哚乙酸的文献报道值[ 15]
一致 。
化合物 5:黄色粉末;1 H-NMR(CDCl3)δ7.04
(1H ,d , J =1.3 Hz , H-2),7.60(1H ,d , J =7.9 Hz ,
H-4),7.14(1H , t , J =7.2 Hz , H-5), 7.21(1H , t ,
J =7.2 Hz ,H-6), 7.38(1H , d , J =8.1 Hz , H-7),
2.99(2H , t , J =6.7 Hz , H-10), 3.60(2H , m , H-
11), 1.92(3H , s , H-2′);13 C-NMR(CDC l3)δ122.0
(C-2),113.2(C-3),118.7(C-4), 119.6(C-5), 122.3
(C-6),111.3(C-7), 136.5(C-8),127.5(C-9), 25.3
(C-10),39.9(C-11), 170.0(C-1′),23.3(C-2′);其波
谱数据与 N-乙酰色胺的文献报道值[ 16] 一致 。
化合物 6:无色晶体;mp:90 ~ 92℃;1 H-NM R
(CDCl3)δ3.63(1H ,m , H-3), 5.56(1H , dd , J =5.2 ,
1.7 Hz , H-7), 5.38(1H , dd , J =5.5 , 2.7 Hz , H-
11), 0.63(3H , s , H-18), 0.94(3H , s , H-19), 1.03
(3H ,d , J =6.6 Hz , H-21), 5.20(2H ,m ,H-22/23),
0.84(3H ,d , J =7.2 Hz , H-26),0.82(3H , d , J =7.1
Hz ,H-27), 0.92(3H , d , J =6.8 Hz , H-28);13 C-
NMR(CDCl3)δ37.2(C-1), 32.1(C-2), 70.5(C-3),
39.2(C-4), 40.4(C-5), 38.4(C-6), 116.4(C-7),
139.8(C-8), 141.3(C-9), 37.1(C-10), 119.6(C-
11), 40.9(C-12), 42.9(C-13),54.6(C-14), 23.0(C-
15), 28.2(C-16), 55.9(C-17),12.1(C-18), 16.3(C-
19), 42.9(C-20),19.9(C-21), 132.1(C-22), 135.6
(C-23), 46.3(C-24),33.1(C-25),19.6(C-26),21.2
(C-27),17.6(C-28);其波谱数据与(22E , 24R)-麦角
甾-7 ,9 , 22-三烯-3β-醇的文献报道值[ 17] 一致 。
化合物 7:无色晶体;mp:181 ~ 182℃;1H-NM R
(CDCl3)δ3.92(1H , m , H-3), 6.47(1H , d , J =8.5
Hz ,H-6), 6.22(1H , d , J = 8.5 Hz , H-7), 0.79
(3H , s ,H-18), 0.86(3H , s , H-19),0.98(3H ,d , J =
6.5 Hz , H-21), 5.12(1H , dd , J =15.4 ,8.3 Hz , H-
22), 5.21(1H , dd , J =15.3 , 7.5 Hz , H-23), 0.80
(3H , d , J =6.8 Hz , H-26),0.81(3H , d , J =6.8 Hz ,
H-27),0.89(3H , d , J =6.8 Hz , H-28);13 C-NM R
(CDC l3)δ34.7(C-1), 30.0(C-2), 66.2(C-3), 39.3
(C-4),82.1(C-5), 135.1(C-6), 130.6(C-7), 79.4
(C-8),51.1(C-9), 36.9(C-10), 20.6(C-11), 36.8
(C-12), 44.5(C-13),51.6(C-14), 23.3(C-15), 28.5
(C-16), 56.2(C-17),12.8(C-18), 18.1(C-19), 39.6
(C-20), 20.8(C-21), 135.4(C-22), 132.2(C-23),
42.7(C-24), 33.0(C-25), 19.6(C-26),19.9(C-27),
17.5(C-28);其波谱数据与过氧化麦角甾醇的文献
报道值[ 18] 一致 。
化合物 8:无色晶体;mp:172 ~ 173℃;13 C-NMR
(acetone-d6)δ32.1(C-1), 31.1(C-2), 68.7(C-3),
40.4(C-4), 65.1(C-5), 63.4(C-6), 67.6(C-7),
134.4(C-8), 128.3(C-9), 38.8(C-10), 24.2(C-11),
36.9(C-12), 43.0(C-13), 50.9(C-14),24.2(C-15),
29.6(C-16), 54.8(C-17), 11.8(C-18),22.9(C-19),
41.3(C-20), 21.5(C-21), 136.9(C-22), 132.7(C-
23),43.8(C-24),34.0(C-25), 20.0(C-26), 20.4(C-
27),18.2(C-28);其波谱数据与(22E , 24R)-5α, 6α-
环氧麦角甾-8 , 22-二烯-3β , 7α-二醇的文献报道值[ 18]
一致。
化合 物 9:无色晶体;81 ~ 83℃;1 H-NMR
(CDC l3)δ4.05(1H , m , H-3), 3.17(1H , d , J =5.1
Hz ,H-6),5.40(1H , m , H-7), 0.59(3H , s , H-18),
1.00(3H , s , H-19),1.02(3H ,d , J =6.6 Hz , H-21),
5.17(1H ,dd , J =15.3 , 7.3 Hz , H-22), 5.21(1H ,
dd , J =15.3 , 8.0 Hz , H-23), 0.82(3H , d , J =7.1
Hz ,H-26), 0.83(3H , d , J =7.4 Hz , H-27), 0.91
(3H , d , J =6.8 Hz , H-28), 3.39(3H , s , 6-OCH 3);
13C-NMR(CDCl3)δ31.0(C-1),32.8(C-2), 67.9(C-
3),39.7(C-4), 76.4(C-5),82.5(C-6), 115.0(C-7),
143.7(C-8), 43.9(C-9), 37.3(C-10),22.9(C-11),
39.4(C-12), 44.0(C-13), 55.0(C-14),22.2(C-15),
27.9(C-16), 56.1(C-17), 12.3(C-18),18.3(C-19),
40.3(C-20), 21.2(C-21), 135.5(C-22), 132.2
(C-23), 42.9(C-24),33.1(C-25), 19.6(C-26), 19.9
(C-27), 17.6(C-28), 58.2(6-OCH3);其波谱数据与
(22E , 24R)-麦角甾-7 , 22-二烯-6β-甲氧基-3β , 5α-二
醇的文献报道值[ 19] 一致 。
化合物 10:无色晶体;mp:243 ~ 246℃;1 H-
NMR(DMSO-d6)δ4.08(1H , m , H-3), 3.63(1H , d ,
J =5.0 Hz , H-6), 5.66(1H , m , H-7), 0.60(3H , s ,
H-18), 1.09(3H , s ,H-19), 1.03(3H ,d , J =6.6 Hz ,
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H-21),5.17(1H ,dd , J =15.3 , 8.0 Hz ,H-22),5.23
(1H ,dd , J =15.3 , 7.4 Hz , H-23), 0.82(3H , d , J =
7.2 Hz , H-26), 0.84(3H , d , J =7.2 Hz , H-27),
0.92(3H ,d , J =6.8 Hz , H-28);13 C-NMR(DMSO)
δ30.9(C-1), 32.4(C-2), 65.9(C-3), 40.1(C-4),
74.4(C-5), 72.1(C-6), 119.3(C-7), 139.6(C-8),
42.2(C-9), 36.6(C-10), 21.4(C-11), 39.3(C-12),
42.9(C-13),54.1(C-14), 22.5(C-15), 27.9(C-16),
55.3(C-17),12.0(C-18), 17.6(C-19), 39.8(C-20),
20.8(C-21), 135.3(C-22), 131.3(C-23), 41.9(C-
24), 32.4(C-25), 19.6(C-26),19.3(C-27), 17.2(C-
28);其波谱数据与啤酒甾醇的文献报道值[ 20]一致。
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研究论文· ARTICLE
Marine Sciences/ Vo l.32 , No.11/ 2008
Chemical constituents of Hypocreales sp., an endophytic fun-
gus derived from the red alga Symphyocladia latiuscula
LI Dong-li1 , 2 , LI Xiao-ming1 , CUI Chuan-ming1 , WANG Bin-gui1
(1.Key Laboratory of Experimental M arine Biolog y , Insti tute of Oceanolog y , Chinese Academy o f
S ciences , Qingdao 266071 , China;2.G raduate University of the Chinese Academy of Sciences , Bei jing
100049 , China)
Received:Feb., 20 , 2008
Key words:Symphyocladia latiuscula;endophy tic fungus;Hy pocreales sp.;chemical constituents
Abstract:From the fermentat ion bro th of Hypocreales sp., an endophy tic fungus derived f rom the red alga
Symphyoclad ia lat iuscula , ten compounds w ere isolated by the no rmal phase silica gel , Sephadex LH-20
column chromato graphy separation , and by the preparative thin layer chromato graphy (PTLC)as w ell as by
re-cry stallization.Structures of purified compounds w ere elucidated by analysis o f spect roscopic data inclu-
ding M S , 1D and 2D NMR as bisphenol A (1), salicylic acid(2), 3-indolefo rmic acid (3), 3-indo leacet ic
acid(4), N-acety lt ryptamine (5), 22E , 24R-ergo sta-7 , 9 , 22-t rien-3β-ol (6), ergo sterol pe roxide (7), and
22E , 24R-5α, 6α-epoxyerg osta-8 , 22-dien-3β , 7α-diol (8), erg osta-7 , 22-dien-6β-methoxy-3β , 5α-diol (9),
cerevisterol(10).All the compounds w ere obtained from this fungus fo r the first time and compound(1)
was reported as a new natural product.
(本文编辑:张培新)
(上接第 8页)
Abstract:Mass selection and pedig ree select ive breeding w ere perfo rmed using periodic and family selection
methods in 14 dif ferent populations f rom three different origins.206 pedig rees w ere set up in Li topenaeus
vannamei , 120 pedig rees , which w ere g row slow ly and wi th less anti-st ress ability , were eliminated through
select ion according to different biological crite ria.The g row th and rate of mo rpholog ical abnormality of 80
pedig rees , which w ere cultured to commercial stage , we re stat ist icated.The results demonst rated that there
are significant differences in g row th rate mor tality and abno rmal rate betw een dif ferent pedigrees although
they w ere cultured in the same o r similar environment.The w eights o f 150 day sshrimp in all the pedig rees
were in no rmal dist ribution.40 pedigrees , which have a be tter biolo gical pheno type , were selected for the
nex t gene rat ion production.
Combined wi th the theo ry and product ion in selective breeding at home and abroad , population selec-
tion and individual selection in Litopenaeus vannamei were performed by creationary , stati stic and compari-
son analy sis on g row ing condition in 80 select ived populations we re dealt , the rate of mo rphological abnor-
mali ty w as taken as one of selection guide lines first time , populat ion selection sy stem in Li topenaeus van-
namei was set preliminarily , a bet ter technical stage fo r product ion and theory study w as set.A nd i t maybe
pro vide bet ter thoroughbred in aquacul ture breeding of praw n in the future.
(本文编辑:刘珊珊)
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