药学学报

Position	^aδ_C, type	^bδ_C, type	^aδ_H (J in Hz)	^bδ_H (J in Hz)
1	101.2, CH	101.0, CH	5.19, s	5.07, s
3	155.6, C	153.8, C
4	103.4, CH	104.3, CH	5.71, s	5.81, s
4a	149.1, C	149.4, C
5	118.3, CH	118.8, CH	5.89, s	5.66, s
6	200.1, C	201.3, C
7	77.7, C	76.8, C
8	72.5, CH	71.8, CH	4.25, s	3.88, d (6.0)
8-OH				5.35, d (6.0)
8a	68.8, C	68.2, C
8a-OH				4.88, s
9	119.1, CH	120.3, CH	5.95, d (15.5)	6.06, d (15.5)
10	140.6, CH	138.0, CH	7.01, d (15.5)	6.89, d (15.5)
11	132.3, C	132.2, C
12	146.5, CH	144.3, CH	5.60, d (10.0)	5.60, d (10.0)
13	35.1, CH	34.2, CH	2.45, m	2.44, m
14	30.3, CH₂	29.7, CH₂	1.41, m; 1.30, m	1.35, m; 1.24, m
15	12.6, CH₃	12.4, CH₃	0.86, t (7.0)	0.82, t (7.0)
16	20.5, CH₃	20.3, CH₃	0.98, d (7.0)	0.95, d (7.0)
17	12.1, CH₃	11.9, CH₃	1.79, s	1.77, s
18	22.4, CH₃	21.6, CH₃	1.47, s	1.25, s
19	57.2, OCH₃	56.4, OCH₃	3.51, s	3.37, s

Position	^aδ_C, type	^bδ_C, type	^aδ_H (J in Hz)	^bδ_H (J in Hz)
1	101.2, CH	101.0, CH	5.19, s	5.07, s
3	155.6, C	153.8, C
4	103.4, CH	104.3, CH	5.71, s	5.81, s
4a	149.1, C	149.4, C
5	118.3, CH	118.8, CH	5.89, s	5.66, s
6	200.1, C	201.3, C
7	77.7, C	76.8, C
8	72.5, CH	71.8, CH	4.25, s	3.88, d (6.0)
8-OH				5.35, d (6.0)
8a	68.8, C	68.2, C
8a-OH				4.88, s
9	119.1, CH	120.3, CH	5.95, d (15.5)	6.06, d (15.5)
10	140.6, CH	138.0, CH	7.01, d (15.5)	6.89, d (15.5)
11	132.3, C	132.2, C
12	146.5, CH	144.3, CH	5.60, d (10.0)	5.60, d (10.0)
13	35.1, CH	34.2, CH	2.45, m	2.44, m
14	30.3, CH₂	29.7, CH₂	1.41, m; 1.30, m	1.35, m; 1.24, m
15	12.6, CH₃	12.4, CH₃	0.86, t (7.0)	0.82, t (7.0)
16	20.5, CH₃	20.3, CH₃	0.98, d (7.0)	0.95, d (7.0)
17	12.1, CH₃	11.9, CH₃	1.79, s	1.77, s
18	22.4, CH₃	21.6, CH₃	1.47, s	1.25, s
19	57.2, OCH₃	56.4, OCH₃	3.51, s	3.37, s

一株红树林来源真菌Scedosporium aurantiacum GXIMD 02519次级代谢产物研究

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陆雅琪 , 林妙萍 , 齐鑫 , 彭帅 , 覃育宁 , 卢护木 , 刘永宏 , 罗小卫 ^*

药学学报 | 研究论文 2025,60(6): 1847-1854

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药学学报 |研究论文 2025 , 60 (6) : 1847 -1854

一株红树林来源真菌Scedosporium aurantiacum GXIMD 02519次级代谢产物研究

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陆雅琪, 林妙萍, 齐鑫, 彭帅, 覃育宁, 卢护木, 刘永宏, 罗小卫^*

作者信息

广西中医药大学, 海洋药物研究院, 广西海洋药物重点实验室/海洋中药资源高效利用广西高校工程研究中心, 广西南宁 530200

通讯作者:

罗小卫, Tel: 86-771-4733826, E-mail: luoxiaowei1991@126.com

作者简介:

作者贡献

罗小卫研究员全面负责实验设计和指导实施, 稿件的撰写及修改; 陆雅琪负责化合物的分离、鉴定和文章初稿撰写; 林妙萍和彭帅负责化合物活性测试; 齐鑫和覃育宁对化合物的提取分离和结构鉴定提供了建议; 卢护木负责数据整理工作; 刘永宏研究员对实验设计提供建议。

Study on secondary metabolites of a mangrove-derived fungus Scedosporium aurantiacum GXIMD 02519

Ya-qi LU, Miao-ping LIN, Xin QI, Shuai PENG, Yu-ning QIN, Hu-mu LU, Yong-hong LIU, Xiao-wei LUO^*

Affiliations

University Engineering Research Center of High-efficient Utilization of Marine Traditional Chinese Medicine Resources, Guangxi/Guangxi Key Laboratory of Marine Drugs, Institute of Marine Drugs, Guangxi University of Chinese Medicine, Nanning 530200, China

出版时间: 2025-06-12 doi: 10.16438/j.0513-4870.2025-0035

文章导航

摘要

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采用硅胶柱色谱和半制备高效液相色谱等技术对菌株Scedosporium aurantiacum GXIMD 02519的大米培养基发酵产物进行分离纯化, 运用HR-ESIMS、NMR等谱学方法对单体化合物的结构进行鉴定, 采用核因子κB (NF-κB) 荧光素酶报告基因技术和抗酒石酸酸性磷酸酶(TRAP) 染色法探讨化合物对NF-κB和破骨细胞分化抑制活性的影响。从菌株S. aurantiacum GXIMD 02519的次级代谢产物中分离鉴定了1个新的嗜氮酮类化合物以及9个已知化合物, 分别为isochromophilone M (1)、6-((1E, 3E)-3, 5-二甲基庚-1, 3-二烯-1-基)-2, 4-二羟基-3-甲基苯甲醛(2)、barbatinic acid (3)、botryorhodine B (4)、2, 6-二羟基-3, 4-二甲基苯甲酸甲酯(5)、2, 4-二羟基-3, 6-二甲基苯甲酸(6)、atranol (7)、2-(4-甲氧基苯基)乙酸(8)、对羟基苯甲醛(9)、scopararane C (10)。化合物3和10对脂多糖(LPS) 诱导的RAW264.7细胞中NF-κB活化具有抑制作用, 化合物10能进一步抑制NF-κB配体的受体激活剂(RANKL) 诱导的骨髓巨噬细胞分化为破骨细胞, 且无明显细胞毒性。本文首次报道了二萜类化合物10是一种潜在破骨细胞分化抑制剂。

关键词

红树林 / Scedosporium aurantiacum / 次级代谢产物 / 聚酮 / 破骨细胞分化

Abstract

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The rice fermentation products of the fungus Scedosporium aurantiacum GXIMD 02519 were isolated and purified by silica gel column chromatography and semi-preparative liquid chromatography, etc. Their structures were characterized by various spectroscopic methods, including HR-ESIMS and NMR, etc. The inhibitory activity of nuclear factor kappa-B (NF-κB) and osteoclast differentiation of these compounds were determined by approaches of NF-κB luciferase reporter gene and tartrate-resistant acidic phosphatase (TRAP) staining. A new azaphilone, isochromophilone M (1), along with nine known compounds, were isolated and identified from the fungus S. aurantiacum GXIMD 02519, which were identified as 6-((1E, 3E)-3, 5-dimethylhepta-1, 3-dien-1-yl)-2, 4-dihydroxy-3-methylbenzaldehyde (2), barbatinic acid (3), botryorhodine B (4), 2, 6-dihydroxy-3, 4-dimethylbenzoic acid methyl ester (5), 2, 4-dihydroxy-3, 6-dimethylbenzoic acid (6), atranol (7), 4-methoxyphenylacetic acid (8), 4-hydroxybenzaldehyde (9), and scopararane C (10). Compounds 3 and 10 showed inhibitions of lipopolysaccharide (LPS)-induced NF-κB activation in RAW264.7 cells. Moreover, compound 10 could further inhibit receptor activator of nuclear factor κB ligand (RANKL)-induced osteoclast differentiation in bone marrow macrophages without observed cytotoxicity. This is the first report of the diterpene compound (10) as a potential inhibitor of osteoclast differentiation.

Key words

mangrove / Scedosporium aurantiacum / secondary metabolite / polyketide / osteoclast differentiation

引用本文

陆雅琪, 林妙萍, 齐鑫, 彭帅, 覃育宁, 卢护木, 刘永宏, 罗小卫. 一株红树林来源真菌Scedosporium aurantiacum GXIMD 02519次级代谢产物研究. 药学学报, 2025 , 60 (6) : 1847 -1854 . DOI: 10.16438/j.0513-4870.2025-0035

Ya-qi LU, Miao-ping LIN, Xin QI, Shuai PENG, Yu-ning QIN, Hu-mu LU, Yong-hong LIU, Xiao-wei LUO. Study on secondary metabolites of a mangrove-derived fungus Scedosporium aurantiacum GXIMD 02519[J]. Acta Pharmaceutica Sinica, 2025 , 60 (6) : 1847 -1854 . DOI: 10.16438/j.0513-4870.2025-0035

正文

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随着全球老龄化的加剧, 骨质疏松症被视为全球主要的公共卫生问题之一, 其特征是骨骼微结构发生变化, 即骨稳态平衡被打破, 严重威胁人们健康, 尤其是中老年人和绝经期妇女^[1]。骨稳态是指骨骼系统中破骨细胞和成骨细胞相互作用的过程, 它们共同维持骨骼的动态平衡^[2]。破骨细胞是体内唯一具有骨吸收活性的细胞, 破骨细胞的分化和激活受炎症介质如肿瘤坏死因子(TNF)-α和白细胞介素1β (IL-1β)、IL-6、IL-17影响^[3]。破骨细胞的形成和成熟主要受两种因子调控, 即RANKL和巨噬细胞集落刺激因子(M-CSF) 的影响。靶向抑制破骨细胞分化成为防治骨质疏松等溶骨性疾病的重要方法, 但是当前临床上主要使用的基于破骨细胞分化抑制的药物如双膦酸盐酸类(bisphosphonate) 和地诺单抗(denosumab), 却具有严重的不良反应^[4], 故迫切需要研制具有抗骨质疏松药用价值的新型破骨细胞分化抑制剂。

海洋天然产物具有复杂多样的化学结构, 是抗破骨细胞分化活性分子的重要来源^[5]。北部湾位于中国南海的西北部, 蕴育着丰富的海洋(微) 生物资源, 在海洋活性物质开发利用方面具有独特优势^[6]。据统计, 北部湾海洋天然产物主要来源海洋宏生物(48%) 和海洋微生物(52%), 结构类型以聚酮类和萜类为主, 具有良好的细胞毒性、抗炎和抗菌活性^[7]。本团队长期致力于北部湾海洋微生物活性代谢产物研究, 近年来从中筛选发现系列新型破骨细胞分化抑制剂, 包括氯代聚酮^[8]、pyrazinemethanol^[9]、orsaldechlorins^[10]和tanzawaic acids^[11]等化合物。

桔黄赛多孢霉(Scedosporium aurantiacum) 是一种机会性致病性真菌, 在环境中广泛分布, 包括土壤、污泥和沉积物样品^[12], 临床上通常在肺、鼻窦、眼睛、骨骼、中枢神经系统和内脏器官中引起多种疾病^[13]。近期团队从北海红树林保护区海榄雌[Avicennia marina (Forsk.) Vierh.] 底泥中分离获得一株赛多孢霉属真菌Scedosporium aurantiacum GXIMD 02519, 该菌株代谢产物研究较少, 本研究从其大米培养基发酵产物中分离鉴定了1个新的嗜氮酮类化合物以及9个已知化合物(图1), 分别为isochromophilone M (1)、6-((1E, 3E)-3, 5-二甲基庚-1, 3-二烯-1-基)-2, 4-二羟基-3-甲基苯甲醛(2)、barbatinic acid (3)、botryorhodine B (4)、2, 6-二羟基-3, 4-二甲基苯甲酸甲酯(5)、2, 4-二羟基-3, 6-二甲基苯甲酸(6)、atranol (7)、2-(4-甲氧基苯基)乙酸(8)、对羟基苯甲醛(9)、scopararane C (10)。对分离所得的化合物进行抑制破骨细胞分化活性测试, 化合物3和10对LPS诱导的RAW264.7细胞中NF-κB活化具有抑制作用, 化合物10能进一步抑制RANKL诱导的骨髓巨噬细胞分化为破骨细胞, 且无明显骨髓巨噬细胞毒性。

结果与讨论

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1　结构鉴定

化合物1为淡黄色油状, 易溶于甲醇和二氯甲烷。高分辨质谱图HR-ESIMS中准分子离子峰m/z 387.177 9 [M+Na]⁺ (计算值为C₂₀H₂₈NaO₆, 387.178 4) 说明化合物分子式为C₂₀H₂₈O₆。¹H NMR和¹³C NMR数据(表1), 并结合HSQC谱图给出1个甲氧基信号δ_H/C 3.51 (3H, s, H₃-19)/57.2, 4个甲基信号δ_H/C 1.79 (3H, s, H₃-17)/12.1、1.47 (3H, s, H₃-18)/22.4、0.98 (3H, d, J = 7.0 Hz, H₃-16)/20.5、0.86 (3H, t, J = 7.0 Hz, H₃-15)/12.6, 1个亚甲基信号δ_H/C 1.41, 1.30 (2H, m, H₂-14)/30.3, 3个次甲基信号δ_H/C 5.19 (1H, s, H-1)/101.2、4.25 (1H, s, H-8)/72.5、2.45 (1H, m, H-13)/35.1和5个双键次甲基信号δ_H/C 7.01 (1H, d, J = 15.5 Hz, H-10)/140.6、5.95 (1H, d, J = 15.5 Hz, H-9)/119.1、5.89 (1H, s, H-5)/118.3、5.71 (1H, s, H-4)/103.4、5.60 (1H, d, J = 10.0 Hz, H-12)/146.5, 以及6个季碳信号, 包括1个羰基(δ_C 200.1), 2个连氧季碳(δ_C 77.7、68.8) 和3个双键季碳(δ_C 155.6、149.2、132.3), 以上核磁数据与化合物maximazaphilone IV^[14]的核磁数据非常相似, 主要区别是化合物1中1-OMe (δ_H/C 3.51/57.2) 和8a-OH分别取代了化合物maximazaphilone IV中1位和8a位上的质子。此推断主要通过HMBC谱图(图2) 中H₃-19/C-1和H-1/C-3, C-4a, C-8a相关信号以及季碳C-8a (δ_C 68.8) 向低场偏移的化学位移所证实。化合物1的平面结构也进一步通过二维核磁相关信号(图2) 确认, 命名为isochromophilone M。

化合物1的相对构型主要通过NOESY谱图相关信号和质子偶合常数确定。NOESY谱图(图2) 中H-9/H₃-17和H-10/H-12相关信号, 以及H-9和H-10之间较大的偶合常数(15.5 Hz), 说明∆⁹和∆¹¹双键构型均为E式。此外, NOESY谱图中H₃-18/8a-OH、H₃-1/H-8和1-OMe/8-OH相关信号, 说明其两两分别位于同侧。根据本团队多年来对于嗜氮酮类化合物的研究积累, 并且基于核磁数据比对和生物合成途径考虑^{[15, 16]}, 化合物1中的C-13位手性确定为S构型。综上, 化合物1还存在4种异构体, 采用含时密度泛函理论(TDDFT) 方法计算了化合物1中可能存在的4种异构体的ECD谱图, 结果表明(1R, 7R, 8R, 8aS, 13S)-1构型的计算ECD谱图与实测ECD趋势基本一致(图3), 故确定化合物1的构型为1R, 7R, 8R, 8aS, 13S。经在Scifinder数据库中结构检索确认为新化合物, 命名为isochromophilone M。

2　破骨细胞分化抑制活性

首先利用NF-κB荧光素酶报告基因技术测试所有化合物(20 μmol·L^-1) 对LPS诱导的RAW264.7细胞中NF-κB活化的抑制活性, 结果发现化合物3和10在20 μmol·L^-1时显示出抑制作用(图4)。进一步采用TRAP染色法探讨了化合物10对破骨分化的影响, 研究发现化合物10能够抑制骨髓巨噬细胞分化为破骨细胞(图5), 且在有效浓度20 μmol·L^-1下无明显细胞毒性(图6), 是一个潜在破骨细胞分化抑制剂, 具有抗骨质疏松的药用价值。

3　讨论

本研究从北部湾红树林底泥共附生真菌S. aurantiacum GXIMD 02519的大米培养基发酵产物中, 分离鉴定了10个单体化合物, 包括1个新的嗜氮酮类化合物(1)、8个已知的聚酮类化合物(2~9) 和1个已知的二萜类化合物(10)。其中化合物3和10对LPS诱导的RAW264.7细胞中NF-κB活化具有抑制活性。此外文献报道显示, 化合物10对人乳腺癌细胞MCF-7具细胞毒活性, IC₅₀值为35.9 μmol·L^{-1 [17]}。化合物4对宫颈癌细胞HeLa具细胞毒活性, CC₅₀值为36.41 μmol·L^-1, 还对土曲霉具一定抑制作用, MIC值为49.70 μmol·L^{-1 [18]}。Scedosporium属真菌代谢产物研究较少, 本研究丰富了Scedosporium属真菌代谢产物化学多样性, 首次发现二萜类化合物10具有抑制破骨细胞分化活性, 具有潜在防治骨质疏松等破骨细胞相关溶骨性疾病的药用价值。

实验部分

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旋转蒸发仪(Eyelan-1100V-W型, 日本东京理化株式会社); 超净工作台(ZYJ-S型, 苏州净化设备公司); Bruker AVANCE-500 MHz超导核磁共振仪(TMS为内标, 德国布鲁克公司); 高压灭菌锅(MLS-3781L-PC, 普和希健康医疗器械上海有限公司); 纯水仪(UPH-Ⅱ-20TN, 成都优普仪器设备有限公司); 中压制备色谱仪(Specore, 瑞士BUCHI公司); 高效液相色谱仪(Prominnence LC-2030C3D和SCL-10AVP, 日本岛津公司); 高分辨质谱仪(Xevo G2 QTof型, 美国Waters公司); 圆二色谱仪(J-1500型, 日本JASCO公司); 薄层色谱及柱色谱用硅胶(青岛海洋化工厂); YMC-Pack ODS-A色谱柱(10 mm × 250 mm, 5 μm, 日本YMC公司); COSMOSIL πNAP萘基柱(10 mm × 250 mm, 5 μm, 日本COSMOSIL公司); 分析纯甲醇、乙酸乙酯等化学试剂(上海泰坦科技股份有限公司); 色谱纯甲醇和乙腈试剂(上海星可高纯溶剂有限公司)。

1　菌株来源及鉴定

菌株GXIMD 02519从北海金海湾红树林海榄雌底泥中分离。鉴于真菌基因组中编码核糖体基因的保守性和异种同源性特点, 内转录间隔区(internal transcribed spacer, ITS) 为生物学鉴定重要的参考依据。菌株GXIMD 02519的ITS序列委托北京擎科生物科技股份有限公司负责扩增测序, 通过利用NCBI (National Center of Biotechnology Information) 数据库检索发现其序列与菌株Scedosporium aurantiacum (GeneBank accession no. OW985204.1) 的相似度达100%, 故鉴定为Scedosporium aurantiacum GXIMD 02519 (GeneBank accession no. PQ881879)。该菌株已保存于广西中医药大学海洋药物研究院北部湾海洋微生物资源库中。

2　菌株的培养与发酵

将菌株GXIMD 02519接至MB平板上复苏活化后, 挑取单一菌落接至MB液体培养基中, 将其放于摇床中室温动态培养(180 r·min^-1) 3天, 然后将种子液接种至已经灭菌的1 L三角瓶大米固体培养基(150.0 g大米, 2%海盐, 0.2%玉米浆, 0.1%蛋氨酸, 180 mL水) 中, 共发酵9.6 kg, 室温下发酵30天。

3　提取与分离

收获发酵产物, 加入适量乙酸乙酯, 多次提取直到乙酸乙酯层颜色变淡。合并提取物减压蒸发浓缩得到总浸膏130 g。对总浸膏进行中压硅胶柱色谱分离, 采用石油醚-二氯甲烷-甲醇体系进行梯度洗脱, 经过TLC分析合并后得到8个流分Fr.1~8。流分Fr.3 (7.1 g) 经过中压反相硅胶柱色谱分离, 采用甲醇-水(10%~100%) 梯度洗脱的方式共得到13个子流分Fr.3-1~3-13。流分Fr.3-4 (50 mg) 经半制备HPLC (ODS柱, 48%乙腈-水, 2 mL·min^-1) 纯化得到了化合物5 (t_R = 34.5 min, 5.8 mg)。流分Fr.3-6 (80 mg) 经半制备HPLC (ODS柱, 88%乙腈-水, 2 mL·min^-1) 纯化得到了化合物10 (t_R = 24 min, 7.5 mg)。流分Fr.3-7 (58 mg) 经半制备HPLC (ODS柱, 90%乙腈-水, 2 mL·min^-1) 纯化得到了化合物3 (t_R = 21.5 min, 1.0 mg) 和2 (t_R = 26.5 min, 5.2 mg)。流分Fr.4 (2.8 g) 经过中压反相硅胶柱色谱分离, 采用甲醇-水(10%~100%) 梯度洗脱的方式共得到13个子流分Fr.4-1~4-13。流分Fr.4-4 (16.2 mg) 经半制备HPLC (ODS柱, 40%乙腈-水, 2 mL·min^-1) 纯化得到了化合物7 (t_R = 23 min, 10 mg)。流分Fr.4-11 (47.6 mg) 经半制备HPLC (ODS柱, 80%乙腈-水, 2 mL·min^-1) 纯化得到了化合物4 (t_R = 24 min, 7.7 mg)。流分Fr.5 (400 mg) 经半制备HPLC (ODS柱, 28%乙腈-水, 2 mL·min^-1) 纯化得到了化合物9 (t_R = 16 min, 12 mg) 和化合物8 (t_R = 27 min, 7.3 mg)。Fr.6 (12.1 g) 经过中压反相硅胶柱色谱分离, 采用甲醇-水(10%~100%) 梯度洗脱的方式共得到15个子流分Fr.6-1~6-15。流分Fr.6-9 (750 mg) 经半制备HPLC (ODS柱, 53%乙腈-水, 2 mL·min^-1) 纯化得到了化合物6 (t_R = 24 min, 9.2 mg)。流分Fr.6-11 (448 mg) 经半制备HPLC (萘基柱, 50%乙腈-水, 2 mL·min^-1) 纯化得到了化合物1 (t_R = 24 min, 15.3 mg)。

4　化合物结构鉴定

化合物1: 淡黄色油状, 易溶于甲醇和二氯甲烷。

$ {\left[\alpha \right]}_{\mathrm{D}}^{25} $

+26 (c 0.2, CH₃OH); UV (MeOH) λ_max (log ε) 365 (3.91), 262 (3.53), 200 (3.90) nm; ECD (0.2 mg·mL^-1, CH₃OH) λ_max (Δε) 319 (+4.06), 260 (‒4.60), 208 (+1.18) nm; ¹H NMR和¹³C NMR数据见表1; 高分辨质谱HR-ESIMS m/z 387.177 9 [M+Na]⁺ (计算值为C₂₀H₂₈NaO₆, 387.178 4), 365.196 4 [M+H]⁺ (计算值为C₂₀H₂₉O₆, 365.196 4)。

化合物2: 黄色油状, ¹H NMR (500 MHz, CDCl₃) δ_H: 10.14 (1H, s, H-7′), 6.80 (1H, d, J = 16.0 Hz, H-1), 6.62 (1H, d, J = 16.0 Hz, H-2), 6.46 (1H, s, H-6′), 5.46 (1H, d, J = 9.3 Hz, H-4), 2.46 (1H, m, H-5), 2.11 (3H, s, H₃-8′), 1.87 (1H, s, H₃-9), 1.36 (1H, m, H-6β), 1.28 (1H, m, H-6α), 1.00 (3H, d, J = 6.6 Hz, H₃-8), 0.87 (3H, t, J = 7.4 Hz, H₃-7); ¹³C NMR (125 MHz, CDCl₃) δ_C: 119.4 (CH, C-1), 140.7 (CH, C-2), 132.4 (C, C-3), 143.5 (CH, C-4), 34.8 (CH, C-5), 30.4 (CH₂, C-6), 12.1 (CH₃, C-7), 20.7 (CH₃, C-8), 12.9 (CH₃, C-9), 142.9 (C, C-1′), 112.3 (C, C-2′), 161.1 (C, C-3′), 109.9 (C, C-4′), 163.8 (C, C-5′), 106.0 (CH, C-6′), 193.4 (CHO, C-7′), 7.2 (CH₃, C-8′)。以上数据与文献^[16]报道基本一致, 故鉴定化合物2为6-((1E, 3E)-3, 5-dimethylhepta-1, 3-dien-1-yl)-2, 4-dihydroxy-3-methylbenzaldehyde。

化合物3: 白色固体, ¹H NMR (500 MHz, CDCl₃) δ_H: 6.51 (1H, s, H-5′), 6.31 (1H, s, H-5), 3.98 (3H, s, 4-OMe), 2.61 (3H, s, H₃-8′), 2.53 (3H, s, H₃-8), 2.13 (3H, s, H₃-9′), 2.08 (3H, s, H₃-9); ¹³ C NMR (CDCl₃, 125 MHz) δ_C: 111.3 (C, C-1), 163.0 (C, C-2), 104.3 (C, C-3), 159.1 (C, C-4), 109.1 (CH, C-5), 140.8 (C, C-6), 164.3 (C, C-7), 24.2 (CH₃, C-8), 7.8 (CH₃, C-9), 110.4 (C, C-1′), 163.0 (C, C-2′), 117.3 (C, C-3′), 152.6 (C, C-4′), 116.5 (CH, C-5′), 139.8 (C, C-6′), 172.3 (C, C-7′), 24.7 (CH₃, C-8′), 9.5 (CH₃, C-9′), 52.4 (CH₃, 4-OMe)。以上数据与文献^[19]报道基本一致, 故鉴定化合物3为barbatinic acid。

化合物4: 淡褐色固体, ¹H NMR (500 MHz, DMSO-d₆) δ_H: 10.58 (1H, s, H-8), 6.79 (1H, s, H-5), 6.50 (1H, s, H-1′), 2.42 (3H, s, H₃-9), 2.22 (3H, s, H₃-7′), 2.07 (3H, s, H₃-8′); ¹³C NMR (125 MHz, DMSO-d₆) δ_C: 112.3 (C, C-1), 161.9 (C, C-2), 111.6 (C, C-3), 164.2 (C, C-4), 117.0 (CH, C-5), 153.1 (C, C-6), 164.7 (C, C-7), 192.1 (C, C-8), 21.6 (CH₃, C-9), 113.0 (CH, C-1′), 152.2 (C, C-2′), 114.2 (C, C-3′), 142.9 (C, C-4′), 141.7 (C, C-5′), 127.0 (C, C-6′), 16.5 (CH₃, C-7′), 9.3 (CH₃, C-8′)。以上数据与文献^[18]报道基本一致, 故鉴定化合物4为botryorhodine B。

化合物5: 白色固体, ¹H NMR (500 MHz, CDCl₃) δ_H: 12.03 (1H, s, 1-OH), 6.21 (1H, s, H-6), 5.24 (1H, s, 3-OH), 3.92 (3H, s, H₃-8), 2.46 (3H, s, H₃-10), 2.10 (3H, s, H₃-9); ¹³C NMR (125 MHz, CDCl₃) δ_C: 163.3 (C, C-1), 108.7 (C, C-2), 158.2 (C, C-3), 105.4 (C, C-4), 140.3 (C, C-5), 110.7 (CH, C-6), 172.8 (C, C-7), 52.0 (CH₃, C-8), 7.8 (CH₃, C-9), 24.2 (CH₃, C-10)。以上数据与文献^[20]报道基本一致, 故鉴定化合物5为2, 6-dihydroxy-3, 4-dimethylbenzoic acid methyl ester。

化合物6: 白色粉末, ¹H NMR (500 MHz, CD₃OD) δ_H: 6.33 (1H, s, H-5), 2.58 (3H, s, H₃-8), 2.03 (3H, s, H₃-9); ¹³C NMR (125 MHz, CD₃OD) δ_C: 112.2 (C, C-1), 165.1 (C, C-2), 103.9 (C, C-3), 162.6 (C, C-4), 110.3 (CH, C-5), 141.4 (C, C-6), 171.5 (C, C-7), 24.7 (CH₃, C-8), 8.0 (CH₃, C-9)。以上数据与文献^[21]报道基本一致, 故鉴定化合物6为2, 4-dihydroxy-3, 6-dimethylbenzoic acid。

化合物7: 白色固体, ¹H NMR (500 MHz, DMSO-d₆) δ_H: 10.15 (1H, s, H-7), 6.20 (2H, s, H-2, 6), 2.20 (3H, s, H₃-8); ¹³C NMR (125 MHz, DMSO-d₆) δ_C: 150.6 (C, C-1), 107.3 (CH, C-2, 6), 161.9 (C, C-3, 5), 108.1 (C, C-4), 193.5 (C, C-7), 22.1 (CH₃, C-8)。以上数据与文献^[22]报道基本一致, 故鉴定化合物7为atranol。

化合物8: 无色油状, ¹H NMR (500 MHz, CDCl₃) δ_H: 7.12 (2H, d, J = 8.4 Hz, H-2, 6), 6.75 (2H, d, J = 8.4 Hz, H-3, 5), 3.70 (3H, s, 4-OMe), 3.56 (2H, s, H₂-7); ¹³C NMR (125 MHz, CDCl₃) δ_C: 130.6 (C, C-1), 125.9 (CH, C-2, 6), 115.6 (CH, C-3, 5), 155.0 (C, C-4), 40.4 (CH₂, C-7), 173.1 (C, C-8), 52.3 (CH₃, 4-OMe)。以上数据与文献^[23]报道基本一致, 故鉴定化合物8为4-methoxyphenylacetic acid。

化合物9: 白色固体, ¹H NMR (500 MHz, CD₃OD) δ_H: 9.76 (1H, s, H-7), 7.77 (2H, d, J = 8.7 Hz, H-2, 6), 6.91 (2H, d, J = 8.7 Hz, H-3, 5); ¹³C NMR (125 MHz, CD₃OD) δ_C: 130.2 (C, C-1), 133.4 (CH, C-2, 6), 116.9 (C, C-3, 5), 165.2 (C, C-4), 192.8 (C, C-7)。以上NMR数据与文献^[24]报道一致, 故鉴定化合物9为对羟基苯甲醛。

化合物10: 白色固体, ECD (0.2 mg·mL^-1, CH₃OH) λ_max (Δε) 347 (-54.7), 309 (+17.6), 245 (+10.1), 219 (-14.9), 201 (+29.5) nm; ¹H NMR (500 MHz, CDCl₃) δ_H: 7.04 (1H, d, J = 1.7 Hz, H-14), 6.72 (1H, s, 6-OH), 5.87 (1H, dd, J =17.5, 10.6 Hz, H-15), 5.09 (1H, d, J = 17.5 Hz, H-16), 5.05 (1H, d, J = 10.6 Hz, H-16), 1.98 (1H, m, H-1β), 1.93 (1H, m, H-11β), 1.87 (1H, m, H-12α), 1.81 (1H, m, H-11α), 1.63 (2H, m, H₂-2), 1.63 (1H, m, H-12β), 1.55 (1H, m, H-3α), 1.53 (1H, m, H-1α), 1.45 (1H, m, H-3β), 1.41 (3H, s, H₃-18), 1.29 (3H, s, H₃-19), 1.20 (3H, s, H₃-20), 1.12 (3H, s, H₃-17); ¹³C NMR (125 MHz, CDCl₃) δ_C: 30.8 (CH₂, C-1), 17.9 (CH₂, C-2), 41.6 (CH₂, C-3, ), 35.5 (C, C-4), 143.0 (C, C-5), 144.5 (C, C-6), 181.7 (C, C-7), 133.9 (C, C-8), 74.3 (C, C-9), 45.2 (C, C-10), 25.3 (CH₂, C-11), 29.7 (CH₂, C-12), 38.9 (C, C-13), 148.1 (CH, C-14), 145.6 (CH, C-15), 112.7 (CH₂, C-16), 23.5 (CH₃, C-17), 30.2 (CH₃, C-18), 27.1 (CH₃, C-19), 29.7 (CH₃, C-20)。以上数据与文献^[17]报道基本一致, 故鉴定化合物10为scopararane C。

5　化合物1的ECD计算

化合物1的ECD计算主要采用本团队已报道的方法^{[11, 16]}。首先采用Spartan'14软件基于分子默克力场(molecular Merck force field) 对化合物1进行构象搜索, 然后选择Boltzmann分布大于1%的优势构象, 进一步利用Gaussian 16软件在B3LYP/6-311+G(d, p)//B3LYP/6-31+G(d) 水平进行ECD计算, 谱图采用SpecDis 1.71软件处理(半谱宽为0.3 eV), 并经紫外(-30 nm) 校准后绘制。

6　NF-κB和破骨细胞分化抑制活性测试

通过NF-κB荧光素酶报告基因技术测定化合物对LPS诱导的RAW264.7细胞中NF-κB活化的抑制活性^[8-11]。准备NF-κB荧光素酶报告基因稳定转染的RAW264.7细胞, 利用化合物(20 μmol·L^-1) 和BAY11-7082 (NF-κB抑制剂, 阳性对照, 5 μmol·L^-1) 在96孔板中预处理30 min, 然后用5 μg·mL^-1 LPS刺激8 h。对于破骨细胞生成测定, 将浓度为10、15和20 μmol·L^-1的化合物10添加到含M-CSF (50 ng·mL^-1) 和RANKL (100 ng·mL^-1) 刺激的小鼠骨髓巨噬细胞(BMMs) 中, 持续3天。然后固定细胞并染色以获得TRAP活性, 并通过倒置显微镜拍摄图像。

7　统计学分析

采用GraphPad Prism 8统计学软件对实验结果进行统计学分析。实验重复3次, 实验数据以

$ \overline{x} $

± s表示, 各组间的统计差异采用单因素方差分析(ANOVA), 并进行Bonferroni方法检验。P < 0.01为具有统计学意义。

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2025年第60卷第6期

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doi: 10.16438/j.0513-4870.2025-0035

接收时间：2025-01-12
首发时间：2026-09-20
出版时间：2025-06-12

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收稿日期：2025-01-12
修回日期：2025-02-27

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广西中医药大学, 海洋药物研究院, 广西海洋药物重点实验室/海洋中药资源高效利用广西高校工程研究中心, 广西南宁 530200

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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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