药学学报

C No.	δ_H (J/Hz)	δ_C
2		165.4, C
3		112.1, C
4		182.8, C
4a		102.1, C
5		161.7, C
5a		106.5, C
6		159.5, C
7	6.47 (1H, d, J = 2.0)	100.2, CH
8		158.0, C
9	6.88 (1H, d, J = 2.0)	101.1, CH
9a		139.6, C
10	7.09 (1H, s)	100.3, CH
11	2.40 (3H, s)	18.6, CH₃
12	1.92 (3H, s)	8.6, CH₃
1′	5.01 (1H, d, J = 8.0)	99.5, CH
2′	3.27 (1H, dd, J = 8.0, 8.2)	73.3, CH
3′	3.44 (1H, overlap)	75.6, CH
4′	3.08 (1H, dd, J = 9.4, 9.4)	78.7, CH
4′-OMe	3.47 (3H, s)	59.6, CH₃
5′	3.44 (1H, overlap)	76.2, CH
6′	3.54 (1H, overlap) 3.66 (1H, dd, J = 11.3, 3.1)	60.0, CH₂

5-OH	15.90 (1H, br s)
8-OH	9.95 (1H, s)
2′-OH	5.45, (1H, br s)
3′-OH	5.30, (1H, br s)
6′-OH	4.73 (1H, br s)

C No.	δ_H (J/Hz)	δ_C
2		165.4, C
3		112.1, C
4		182.8, C
4a		102.1, C
5		161.7, C
5a		106.5, C
6		159.5, C
7	6.47 (1H, d, J = 2.0)	100.2, CH
8		158.0, C
9	6.88 (1H, d, J = 2.0)	101.1, CH
9a		139.6, C
10	7.09 (1H, s)	100.3, CH
11	2.40 (3H, s)	18.6, CH₃
12	1.92 (3H, s)	8.6, CH₃
1′	5.01 (1H, d, J = 8.0)	99.5, CH
2′	3.27 (1H, dd, J = 8.0, 8.2)	73.3, CH
3′	3.44 (1H, overlap)	75.6, CH
4′	3.08 (1H, dd, J = 9.4, 9.4)	78.7, CH
4′-OMe	3.47 (3H, s)	59.6, CH₃
5′	3.44 (1H, overlap)	76.2, CH
6′	3.54 (1H, overlap) 3.66 (1H, dd, J = 11.3, 3.1)	60.0, CH₂

5-OH	15.90 (1H, br s)
8-OH	9.95 (1H, s)
2′-OH	5.45, (1H, br s)
3′-OH	5.30, (1H, br s)
6′-OH	4.73 (1H, br s)

Compound	HepAD38
GLS4	14.99	98%	72.92	N/A
1	> 50 000	N/A	> 100	N/A
3	4 451	80%	92.26	N/A
4	> 50 000	N/A	> 1 000	N/A
7	> 50 000	N/A	52.28	N/A

Compound	HepAD38
GLS4	14.99	98%	72.92	N/A
1	> 50 000	N/A	> 100	N/A
3	4 451	80%	92.26	N/A
4	> 50 000	N/A	> 1 000	N/A
7	> 50 000	N/A	52.28	N/A

伊岭岩溶洞真菌Metarhizium anisopliae NHC-M3-2中一个新的萘并吡喃酮糖苷

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周丽曼 , 郝祎 , 蒙菊香 , 覃芳芳 , 覃清华 , 王聪 , 孔凡栋 ^*

药学学报 | 研究论文 2023,58(10): 3076-3081

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药学学报 |研究论文 2023 , 58 (10) : 3076 -3081

伊岭岩溶洞真菌Metarhizium anisopliae NHC-M3-2中一个新的萘并吡喃酮糖苷

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周丽曼, 郝祎, 蒙菊香, 覃芳芳, 覃清华, 王聪, 孔凡栋^*

作者信息

广西民族大学化学化工学院, 林产化学与工程国家民委重点实验室, 广西林产化学与工程重点实验室, 广西林产化学与工程协同创新中心, 广西高校少数民族医药古方挖掘与开发重点实验室, 广西南宁 530006

通讯作者:

*孔凡栋, Tel: 15621367387, E-mail: kongfandong0127@126.com

One new glycoside naphthopyranone from the Yiling cave-derived Metarhizium anisopliae NHC-M3-2

Li-man ZHOU, Yi HAO, Ju-xiang MENG, Fang-fang QIN, Qing-hua QIN, Cong WANG, Fan-dong KONG^*

Affiliations

Key Laboratory of Universities in Guangxi for Excavation and Development of Ancient Ethnomedicinal Recipes, Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Key Laboratory of Chemistry and Engineering of Forest Products, State Ethnic Affairs Commission, School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530006, China

出版时间: 2023-10-12 doi: 10.16438/j.0513-4870.2023-0346

文章导航

摘要

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利用硅胶和高效液相等柱色谱方法对溶洞真菌Metarhizium anisopliae NHC-M3-2发酵产物进行分离纯化, 得到了7个化合物。通过紫外、红外、核磁共振谱与质谱方法分别鉴定为2,3-dehydroindigotide G (1)、(-)-regiolone (2)、萘吡喃酮(3)、indigotide G (4)、indigotide B (5)、破伤风毒素A (6) 和破伤风毒素B (7), 其中化合物1为新萘并吡喃酮糖苷类化合物。对分离得到的化合物进行抗乙型肝炎病毒(hepatitis B virus, HBV) 活性测试, 结果显示化合物3的抗HBV作用EC₅₀为4.5 μmol·L^-1, CC₅₀为92.3 μmol·L^-1, 这是首次报道化合物3的抗病毒活性。

关键词

溶洞真菌Metarhizium anisopliae NHC-M3-2 / 次生代谢产物 / 糖苷类化合物 / 抗乙型肝炎活性

Abstract

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Seven compounds were isolated from fermentation extract of cave-derived Metarhizium anisopliae NHC-M3-2 by silica gel, semi-preparative HPLC and other chromatographic methods. Their structures were elucidated by UV, IR, MS and NMR methods as 2,3-dehydroindigotide G (1), (-)-regiolone (2), naphtho-γ-pyrone (3), indigotide G (4), indigotide B (5) destruxin A (6) and destruxin B (7). Compound 1 is a new glycoside naphthopyranone compound. The anti-hepatitis B virus (HBV) activity of these compounds was evaluated. The EC₅₀ and CC₅₀ of compound 3 against HBV were 4.5 μmol·L^-1 and 92.3 μmol·L^-1, respectively. This is the first report of the antiviral activity of compound 3.

Key words

cave-derived Metarhizium anisopliae NHC-M3-2 / secondary metabolite / glycoside compound / anti-hepatitis B activity

引用本文

周丽曼, 郝祎, 蒙菊香, 覃芳芳, 覃清华, 王聪, 孔凡栋. 伊岭岩溶洞真菌Metarhizium anisopliae NHC-M3-2中一个新的萘并吡喃酮糖苷. 药学学报, 2023 , 58 (10) : 3076 -3081 . DOI: 10.16438/j.0513-4870.2023-0346

Li-man ZHOU, Yi HAO, Ju-xiang MENG, Fang-fang QIN, Qing-hua QIN, Cong WANG, Fan-dong KONG. One new glycoside naphthopyranone from the Yiling cave-derived Metarhizium anisopliae NHC-M3-2[J]. Acta Pharmaceutica Sinica, 2023 , 58 (10) : 3076 -3081 . DOI: 10.16438/j.0513-4870.2023-0346

正文

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溶洞是典型的喀斯特地貌, 地理位置相对隔离, 长期阴暗且缺乏直接来自光合作用的有机质, 湿度接近饱和, 温度变化小, 被认为是极端环境。广西溶洞分布广泛, 溶洞微生物活性天然产物的研究鲜有报道。伊岭岩溶洞是一座典型的喀斯特岩溶洞, 被誉为大自然的艺术宝库, 是广西首府南宁的著名风景区, 素有“地下宫殿”之美誉, 具有独特的生态环境。独特的生态环境必然蕴含独特的真菌, 洞穴真菌在长期适应这一特殊生存环境的过程中, 必然进化出与陆生真菌截然不同的代谢途径和适应机制, 进而能够产生大量结构新颖、活性显著的次生代谢物, 是发现药物先导化合物的重要途径^{[1, 2]}。溶洞真菌的研究正在开拓中, 找到更多存在生物活性的新化合物, 对于开创溶洞真菌药物与发现药源分子具有重要意义^{[3, 4]}。

病毒性肝炎是一类严重的传染性疾病, 而乙型肝炎病毒(hepatitis B virus, HBV) 和丙型肝炎病毒(hepatitis C virus, HCV) 则是其中危害极为严重的两种典型肝炎病毒^{[5, 6]}。感染后主要症状包括乏力、发热、肝脏肿大、肝功能异常等。此外, 肝炎病毒感染还可能导致肝硬化、肝癌等严重疾病^[7]。因此, 有必要从药物先导化合物获取的角度, 积极探索抗肝炎活性的有效途径。本文对来自广西依岭岩风景区的溶洞真菌Metarhizium anisopliae NHC-M3-2次级代谢产物进行研究, 从其发酵产物中分离鉴定了7个化合物, 分别鉴定为2,3-dehydroindigotide G (1)、(-)-regiolone (2)、萘吡喃酮(3)、indigotide G (4)、indigotide B (5)、破伤风毒素A (6) 和破伤风毒素B (7), 其中化合物1为一个新的萘并吡喃酮糖苷类化合物(图 1)。活性测试结果显示化合物3具有一定的抗HBV活性。

结果与讨论

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1 伊岭岩溶洞真菌NHC-M3-2的鉴定

菌株NHC-M3-2的PCR (polymerase chain reaction) 扩增序列的长度为533 bp, 与NCBI数据库中的菌株Metarhizium anisopliae (MH859069.1) 的ITS (internally transcribed spacer) 序列同源性为100%, 亲缘关系在系统发育树上处于同一分支。初步鉴定该溶洞真菌NHC-M3-2 (GenBank登录号: OQ398188) 为绿僵菌属Metarhizium sp. (图 2)。菌株生长一段时间后进一步观察其形态特征, 菌落呈深绿色、绒状, 与金龟子绿僵菌的形态特征一致, 故鉴定菌株NHC-M3-2为绿僵菌属Metarhizium anisopliae^[8]。

2 结构解析

化合物1 浅黄色膏状, 不饱和度为11, 比旋光度[α]$ {}_{\mathrm{D}}^{25} $ = 168 (c 0.1, CH₃OH); 正离子高分辨质谱HR-ESI-MS在m/z 449.148 3 (计算值499.146 2) 给出准分子离子峰[M+H]⁺, 提示分子式为C₂₂H₂₄O₁₀; 红外光谱(IR) 给出羟基和羰基(3 382和1 664 cm^-1) 等官能团的特征吸收峰; 紫外光谱(UV) 在227和274 nm给出特征吸收峰, 且与已知化合物萘并吡喃糖苷G (化合物5) 紫外吸收相似, 提示1也是萘并吡喃糖苷类化合物。化合物1的¹³C NMR和HSQC谱图给出13个sp²杂化的碳信号(表 1), 包括1个酮羰基(δ 182.8)、3个次甲基(δ_C/H 100.2/6.47, 101.1/6.88, 100.3/7.09), 以及9个季碳; 3个甲基信号, 包括一个氧甲基(δ_C/H 59.6/3.47); 5个含氧次甲基; 一个含氧亚甲基(δ_C/H 60.0/3.54, 3.66)。这些数据与indigotide G的核磁共振波谱数据非常相似^[9]。它们核磁数据的明显区别仅是indigotide G中CH-2和CH-3两个次甲基信号被1中两个sp²杂化的季碳取代, 以及H₃-11和H₃-12两个双重峰的氢信号被化合物1中两个单峰甲基信号取代。以上数据提示, indigotide G中的CH-2/CH-3在化合物1中被氧化为双键。化合物1的HMBC谱图中给出H₃-11和H₃-12到两个双键碳C-2和C-3的相关, 此外H₃-12还与C-4酮羰基相关, 这进一步证明了以上推断(图 3)。通过详尽HMBC和¹H-¹H COSY信号分析(图 3) 确定化合物1的其他部分结构与萘并吡喃糖苷G一致。故化合物1被鉴定为2,3-dehydroindigotide G。化合物1中的糖部分的核磁数据与此菌株分离的两个已知化合物4和5的数据相同^{[10, 11]}, 提示它们具有相同的4′-O-甲基-β-D-葡萄糖片段。此外, 化合物1糖部分的氢谱数据显示H-1/H-2、H-2/H-3、H-3/H-4及H-4/H-5之间的耦合常数分别是8.0、8.2、9.4和9.4 Hz, 这说明这些氢全部位于糖六元环的a键, 进一步证明化合物1的糖部分构型与已知化合物4和5相同。

3 抗肝炎活性测试

使用人肝癌细胞HepAD38为宿主细胞, 以甲磺酸莫非赛定(GLS4, morphothiadin) 为阳性对照, 对化合物进行抗乙型肝炎病毒活性测试, 结果(表 2) 表明, 化合物3有一定的抗HBV活性, 其EC₅₀即体外实验中50%的病毒被抑制时的药物浓度为4.5 μmol·L^-1, 最高的病毒抑制率达到80%, CC₅₀即体外实验中50%的宿主细胞被破坏时的药物浓度为92.26 μmol·L^-1。而化合物3的OH-6被糖苷化的化合物1却无活性, 说明OH-6对该化合物抗乙肝病毒活性的重要性。综上, 化合物3的细胞毒性低而抗乙肝病毒活性较好, 具有开发抗病毒药物应用的潜能, 这也是首次发现该化合物的抗HBV活性。

实验部分

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YXQ-LS-75SII型高压灭菌锅(上海博迅实业有限公司医疗设备厂); HCB-1300V洁净工作台(青岛海尔特种电器有限公司); LRH-500A型生化培养箱(广东泰宏君科学仪器股份有限公司); CR-080R型春霖超声波清洗机(深圳市春霖清洗设备有限公司); K3 TOUCH酶标仪(上海飞世尔实验器材有限公司); TD4N离心机(长沙英泰仪器有限公司); Agilent 1260高效液相色谱仪和Agilent Cary60紫外可见光谱仪(美国安捷伦科技有限公司); 日立Primaide高效液相色谱仪(北京日立科学仪器有限公司); 中压液相制备色谱仪(天津博纳艾杰尔科技有限公司); 色谱级甲醇(苏州速研医药科技有限公司); AL104型分析天平(瑞士梅特勒托利多科技有限公司); Mariner API-TOF型质谱仪(美国应用生物系统公司); WZZ-2S自动旋光仪(上海申光仪器仪表有限公司); YMC*GEL ODS-A-HG反相硅胶(日本株式会社YMC公司); MAGNA-1R550傅里叶变换红外光谱仪(美国赛默飞世尔科技公司)、核磁共振波谱仪(德国布鲁克公司400 MHz); 200~300目正相硅胶(青岛海洋化工集团公司); SCI-VS混匀仪(美国塞洛捷克公司); 琼脂粉(广州赛国生物科技有限公司); 葡萄糖、甘露醇、酵母膏、麦芽糖(中国国药集团化学试剂有限公司); 味精(南宁味一香食品有限公司)、磷酸二氢钾(天津大茂化学试剂厂); 提取分离用醋酸乙酯、甲醇、二氯甲烷(成都市科隆化学品有限公司) 均为工业用化学纯产品。

溶洞真菌Metarhizium anisopliae NHC-M3-2分离于广西伊岭岩风景区来源的内河水(N23°0′39.07″, E108°2′97.21″)。真菌保存于广西民族大学药学系。

1 菌株分子鉴定

溶洞真菌基因组DNA的提取、扩增以及测序纯化三部分是由上海生工生物工程股份有限公司测试。

2 菌株的发酵

将菌株Metarhizium anisopliae NHC-M3-2接种于PDA平板培养基中, 在28 ℃培养3天, 将此菌株接种于真菌2号培养基(葡萄糖1%、甘露醇2%、酵母膏0.3%、麦芽糖2%、味精1%、磷酸二氢钾0.05%) 的锥形瓶(1 000 mL) 中, 室温静置培养30天, 发酵规模为50瓶。

3 发酵产物的提取分离

3.1 菌株提取物制备

采用醋酸乙酯对菌株Metarhizium anisopliae NHC-M3-2发酵物萃取3次, 菌丝体和发酵液经过滤和减压浓缩后分别得到5.55、2.02 g粗提物。

3.2 产物的分离

化合物的分离: 对发酵液萃取物(2.02 g) 进行减压硅胶柱层析, 采用甲醇-水(30∶70→60∶40→90∶10→100∶1, v/v) 梯度洗脱, 共4个梯度(Fr.1~Fr.4), 每个梯度分3次收集。以Fr.1为例, 编号依次为Fr.1.1~Fr.1.3。Fr.1.3 (40.9 mg) 通过HPLC制备(C18半制备柱, 甲醇-水体积比为45∶55, 流量4 mL·min^-1), 得到化合物2 (t_R = 13.4 min, 1.5 mg)。Fr.2.2 (107.7 mg) 通过HPLC制备(C18半制备柱, 甲醇-水体积比为65∶35, 流量4 mL·min^-1), 得到化合物5 (t_R = 14 min, 9.8 mg)。Fr.2.3 (164.5 mg) 通过HPLC制备(C18半制备柱, 甲醇-水体积比为65∶35, 流量4 mL·min^-1), 得到化合物6 (t_R = 16 min, 6.7 mg)。Fr.3.3 (163.9 mg) 通过HPLC制备(C18半制备柱, 甲醇-水体积比为60∶40, 流量4 mL·min^-1), 得到化合物7 (t_R = 12.2 min, 7.1 mg)。

对菌丝体萃取物(5.55 g) 进行中压硅胶柱层析(C18硅胶柱, 流量30 mL·min^-1), 采用甲醇-水(58∶42→69∶31→73∶27→79∶21→85∶15→90∶10→100∶1, v/v) 梯度洗脱, 共7个梯度(分别为Jr.1~Jr.7), 每个梯度分多次收集。以Jr.1为例, 编号依次为Jr.1.1~Jr.1.n。Jr.2合并得到化合物4 (113.2 mg), Jr.4合并得到化合物1(1.16 g)。Jr.5.3 (101.1 mg) 通过HPLC制备(C18半制备柱, 甲醇-水体积比为80∶20, 流量4 mL·min^-1), 得到化合物3 (t_R = 12.3 min, 5.7 mg)。

4 结构鉴定

化合物1 浅黄色膏状; 比旋光度[α]$ {}_{\mathrm{D}}^{25} $ = 168 (c 0.1, CH₃OH); 正离子高分辨质谱HR-ESI-MS给出准分子离子峰m/z: 449.148 3 [M+H]⁺ (计算值499.146 2), 提示分子式为C₂₂H₂₄O₁₀; UV (CH₃OH) λ_max: (log ε) 227.0 (1.09)、274.0 (1.67) nm; IR (KBr) ν_max: 3 382, 1 664 cm^-1; HR-ESI-MS m/z 449.148 3 [M+H]⁺ (C₂₂H₂₄O₁₀, 计算值), ¹H NMR (DMSO-d₆, 400 MHz) 和¹³C NMR (DMSO-d₆, 100 MHz) 数据见表 1。

化合物2 浅黄色粉末, ESI-MS m/z 201.0 [M+Na]⁺, 分子式C₁₀H₁₀O₃; ¹H NMR (400 MHz, DMSO-d₆, J / Hz): δ_H 12.42 (1H, s, 8-OH), 7.50 (1H, t, J = 7.9, H-6), 7.02 (1H, d, J = 7.9, H-5), 6.93 (1H, d, J = 7.9, H-7), 4.92 (1H, q, J = 3.9, H-4), 3.01 (1H, m, H-2), 2.65 (1H, m, H-2), 2.35 (1H, m, H-3), 2.20 (1H, m, H-3); ¹³C NMR (100 MHz, DMSO-d₆): δ_C 204.3 (C, C-1), 162.6 (C, C-8), 145.8 (C, C-4a), 137.0 (CH, C-6), 117.7 (CH, C-7), 117.4 (CH, C-5), 115.2 (CH, C-8a), 67.6 (CH, C-4), 34.5 (CH₂, C-2), 31.2 (CH₂, C-3)。该化合物的数据与文献^[12]报道的一致, 故化合物2鉴定为(-)-regiolone。

化合物3 黄色固体, ESI-MS m/z 273.0 [M+H]⁺, 分子式C₁₅H₁₂O₅; ¹H NMR (400 MHz, DMSO-d₆, J / Hz): δ_H 16.10 (1H, s, 5-OH), 10.21 (1H, s, 6-OH), 9.88 (1H, s, 8-OH), 6.94 (1H, s, H-10), 6.55 (1H, s, H-9), 6.30 (1H, s, H-7), 2.38 (1H, s, H-11), 1.92 (1H, s, H-12); ¹³C NMR (100 MHz, DMSO-d₆): δ_C 182.6 (C, C-4), 165.2 (C, C-2), 162.1 (C, C-5), 160.6 (C, C-8), 158.4 (CH, C-6), 151.4 (C, C-10a), 140.3 (C, C-9a), 111.9 (C, C-3), 105.3 (C, C-5a), 101.3 (C, C-4a), 100.6 (CH, C-9), 100.4 (CH, C-7), 99.2 (CH, C-10), 18.6 (CH₃, C-11), 8.7 (CH₃, C-12)。该化合物的数据与文献^[13]报道的一致, 故化合物3鉴定为萘并吡喃酮。

化合物4 浅黄色油状; ESI-MS m/z 473.1 [M+Na]⁺, 分子式C₂₂H₂₆O₁₀; ¹H NMR (400 MHz, CD₃OD, J / Hz): δ_H 6.70 (1H, s, H-9), 6.53 (1H, s, H-10), 6.41 (1H, s, H-7), 4.92 (H, d, J = 5.4, H-1′), 4.59 (H, m, H-2), 3.92 (H, dd, J = 2.3, 12.1, H-6′), 3.76 (H, dd, J = 4.9, 12.1, H-6′), 3.61 (3H, s, 4′-OMe), 3.50 (3H, m, H-2′, H-3′, H-5′), 3.23 (H, overlap, H-4′), 2.67 (H, m, H-3), 1.24 (3H, d, J = 6.7, H-11), 0.96 (3H, d, J = 6.4, H-12); ¹³C NMR (100 MHz, CDCl₃): δ_C 202.1 (C, C-4), 165.4 (C, C-5), 161.8 (C, C-8), 160.5 (C, C-6), 157.0 (C, C-10a), 144.4 (C, C-9a), 107.6 (C, C-5a), 104.7 (CH, C-9), 103.9 (C, C-4a), 103.8 (C, C-1′), 101.8 (CH, C-7), 101.4 (CH, C-10), 80.5 (CH, C-4′), 79.3 (CH, C-5′), 77.5 (CH, C-3′), 77.4 (CH, C-2), 75.2 (CH, C-2′), 62.1 (CH₂, C-6′), 60.9 (CH₃, 4′-OMe), 47.8 (CH, C-3), 15.7 (CH₃, C-11), 10.5 (CH₃, C-12)。该化合物的数据与文献^[10]报道的一致, 故化合物4鉴定为indigotide G。

化合物5 浅黄色油状; ESI-MS m/z 473.1 [M+Na]⁺, 分子式C₂₂H₂₆O₁₀; ¹H NMR (400 MHz, CD₃OD, J / Hz): δ_H 7.25 (1H, m, H-7), 7.10 (1H, m, H-9), 6.67 (1H, s, H-10), 6.32 (1H, d, J = 8.9, H-1″), 4.50 (H, m, H-2″), 4.12 (H, m, H-3″), 3.95 (2H, overlap, H-2 and H-6″), 3.75 (2H, dd, overlap, H-6″ and H-4″), 3.63 (3H, s, 4″-OMe-H), 3.50 (H, m, H-5″), 2.72 (H, m, H-3), 1.46 (3H, d, J = 6.0, H-11), 1.21 (3H, d, J = 6.4, H-12); ¹³C NMR (100 MHz, CDCl₃): δ_C 202.0 (C, C-4), 165.2 (C, C-5), 161.6 (C, C-8), 160.4 (C, C-6), 156.9 (C, C-10a), 144.2 (C, C-9a), 107.5 (C, C-5a), 104.7 (CH, C-9), 103.9 (C, C-4a), 103.8 (C, C-1″), 103.1 (CH, C-7), 101.7 (CH, C-10), 80.5 (CH, C-4″), 79.2 (CH, C-2), 77.5 (CH, C-3″), 77.4 (CH, C-5″), 75.2 (CH, C-2″), 62.1 (CH₂, C-6″), 60.9 (CH₃, 4″-OMe-C), 47.7 (CH, C-3), 20.0 (CH₃, C-11), 10.5 (CH₃, C-12)。该化合物的数据与文献^[11]报道的一致, 故化合物5鉴定为indigotide B。

化合物6 浅棕色固体; ESI-MS m/z 600.3 [M+Na]⁺, 分子式C₂₉H₄₇N₅O₇; ¹H NMR (400 MHz, DMSO-d₆, J / Hz): δ_H 8.07 (1H, d, J = 10.0, 17-NH), 6.96 (1H, d, J = 9.6, 1-NH), 5.80 (1H, m, H-22), 5.15 (1H, overlap, H-23), 5.00 (2H, overlap, H-8 and H-14), 4.79 (1H, dd, J = 6.4, 9.2, H-1), 4.35 (1H, t, J = 7.6, H-28), 3.82 (3H, m, H-13), 1.17 (3H, d, J = 6.6, H-15), 0.87 (3H, d, J = 6.5, H-10), 0.84 (3H, d, J = 6.7, H-11), 0.77 (6H, overlap, H-3 and H-5); ¹³C NMR (100 MHz, DMSO-d₆): δ_C 173.2 (C, C-6), 172.9 (C, C-19), 170.5 (C, C-29和C-12), 169.0 (C, C-24), 168.2 (C, C-16), 132.2 (CH, C-22), 118.8 (CH₂, C-23), 72.1 (CH, C-2), 60.0 (CH, C-28), 57.1 (CH, C-8), 54.7 (CH₂, C-14), 52.6 (CH₂, C-1), 46.3 (CH₂, C-25), 36.7 (CH, C-2), 34.2 (CH₂, C-21), 34.0 (CH₃, C-18), 32.9 (CH₂, C-17), 30.5 (CH₂, C-27), 27.7 (CH₃, C-13), 27.1 (CH₃, C-7), 26.7 (CH, C-9), 23.7 (CH₂, C-4), 23.5 (CH₂, C-26), 19.1 (CH₃, C-10和C-11), 15.3 (CH₃, C-3), 15.1 (CH₃, C-15), 11.2 (CH₃, C-5)。该化合物的数据与文献^[14]报道的一致, 故化合物6鉴定为破伤风毒素A。

化合物7 浅棕色油状; ESI-MS m/z 630.3 [M+Na]⁺, 分子式C₃₁H₅₃N₅O₇; ¹H NMR (400 MHz, DMSO-d₆, J / Hz): δ_H 8.07 (1H, d, J = 9.5, 17-NH), 6.98 (1H, d, J = 9.4, 1-NH), 5.17 (1H, m, H-14), 4.93 (1H, d, J = 3.1, H-8), 4.78 (1H, dd, J = 6.7, 9.2, H-1), 4.72 (1H, dd, J = 5.8, H-20), 2.54 (3H, s, H-13), 1.17 (3H, d, J = 6.7, H-15), 0.92 (3H, d, H-11), 0.87 (3H, d, H-10), 0.84 (3H, d, H-3), 0.77 (3H, m, H-5); ¹³C NMR (100 MHz, DMSO-d₆): δ_C 173.3 (C, C-6), 172.9 (C, C-19), 170.5 (C, C-12), 169.0 (C, C-30), 168.9 (C, C-25), 159.5 (C, C-16), 71.6 (CH, C-20), 59.6 (CH, C-29), 57.2 (CH, C-8), 54.7 (CH, C-14), 52.6 (CH, C-1), 46.1 (CH₂, C-26), 38.3 (CH₂, C-21), 36.7 (CH, C-2), 34.0 (CH₂, C-18), 32.9 (CH₂, C-17), 30.5 (CH₃, C-7), 28.9 (CH₂, C-28), 27.7 (CH₃, C-13), 26.7 (CH, C-9), 24.0 (CH₂, C-4), 23.8 (CH, C-22), 23.6 (CH₂, C-27), 23.2 (CH₃, C-23), 21.4 (CH₃, C-24和C-10), 19.1 (CH₃, C-11), 15.4 (CH₃, C-3), 15.1 (CH₃, C-15), 11.1 (CH₃, C-5)。该化合物的数据与文献^[15]报道的一致, 故化合物7鉴定为破伤风毒素B。

5 抗肝炎活性测试

本文使用PCR-荧光探针法^[16]检测化合物对肝炎的抑制活性。

致谢: 上海生工生物工程股份有限公司做了菌株测试工作。

作者贡献: 周丽曼是本文第一作者, 负责实验设计、结构解析与论文的写作; 郝祎是本文共同第一作者, 负责谱图整理及文章初稿的撰写; 蒙菊香和覃芳芳负责化合物分离纯化; 覃清华负责样本的采集和前处理; 王聪负责实验指导及结构解析的指导; 孔凡栋是本文的通讯作者, 负责实验设计及把关, 提供本文思路, 参与稿件修改等工作。

利益冲突: 所有作者均声明不存在利益冲突。

基金

收起

国家自然科学基金青年项目(82104034)
广西自然科学基金项目(2021GXNSFBA075036)
广西自然科学基金项目(2021GXNSFBA220040)
广西民族大学校级引进人才科研启动项目(2020KJQD09)
广西民族大学校级引进人才科研启动项目(2021KJQD09)
广西民族大学相思湖青年创新团队(2021RSCXSHQN01)
广西民族大学校级科研项目(2021 MDKJ003)

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2023年第58卷第10期

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doi: 10.16438/j.0513-4870.2023-0346

接收时间：2023-03-21
首发时间：2025-11-21
出版时间：2023-10-12

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收稿日期：2023-03-21
修回日期：2023-04-22

基金

国家自然科学基金青年项目(82104034)

广西自然科学基金项目(2021GXNSFBA075036)

广西自然科学基金项目(2021GXNSFBA220040)

广西民族大学校级引进人才科研启动项目(2020KJQD09)

广西民族大学校级引进人才科研启动项目(2021KJQD09)

广西民族大学相思湖青年创新团队(2021RSCXSHQN01)

广西民族大学校级科研项目(2021 MDKJ003)

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*孔凡栋, Tel: 15621367387, E-mail: kongfandong0127@126.com

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2种不同金属材料的力学参数

科 Family	属数 Number of genus	种数 Number of species	占总种数比例 Percentage of total species (%)	属 Genus	种数 Number of species	占总种数比例 Percentage of total species (%)
鹅膏菌科Amanitaceae	2	11	5.26	鹅膏菌属 Amanita	10	4.78
小菇科 Mycenaceae	2	12	5.74	丝盖伞属 Inocybe	5	2.39
多孔菌科 Polyporaceae	8	14	6.70	蜡蘑属 Laccaria	5	2.39
红菇科 Russulaceae	3	23	11.00	小皮伞属 Marasmius	6	2.87
				小菇属 Mycena	11	5.26
				光柄菇属 Pluteus	5	2.39
				红菇属 Russula	17	8.13
				栓菌属 Trametes	5	2.39

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