Phytochemistry最新文献

英文中文

Lobopaucinoids A-Q, bioactive terpenoids from the soft coral Lobophytum pauciflorum collected in the South China Sea

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry

Pub Date : 2025-01-28 DOI: 10.1016/j.phytochem.2025.114416

Xiao Han , Di Zhang , Xiaolei Li , Xiaobin Li , Xuli Tang , Guoqiang Li

Two undescribed rearranged diterpenoids, lobopaucinoids A and B (1 and 2), along with thirteen undescribed lobane-type diterpenoids lobopaucinoids C–O (3–15) including a C₁₈ (11) and two C₁₇ (12 and 13) undescribed norditerpenoids, were isolated from the soft coral Lobophytum pauciflorum Ehrenberg (Sarcophytidae family) collected from Xisha Islands of the South China Sea. Additionally, two undescribed prenyleudesmane-type diterpenoids, lobopaucinoids P and Q (16 and 17), as well as two known lobane diterpenoids (18 and 19), were also obtained. Their structures were elucidated based on comprehensive spectroscopic data, Mosher's method, Mo₂(OAc)₄ or Rh₂(OCOCF₃)₄-induced circular dichroism experiment, quantum chemical calculations, and single-crystal X-ray diffraction and literature comparison. Biological evaluation indicated that compounds 3, 4 and 15 exhibited weak anti-inflammatory activities with the rates from 24.34 % to 35.13 % at the concentration of 20 μM. In addition, compound 1 showed significant hepatoprotective activity in zebrafish model.

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引用次数: 0

HDAC inhibitor SAHA triggers the production of previously undescribed sesquiterpenes and undergoes biotransformation by the fungus Robillarda sessilis from Verbena officinalis L.

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry

Pub Date : 2025-01-22 DOI: 10.1016/j.phytochem.2025.114411

Liangxiu Liao , Junguo Huang , Tao Zhu , Shan Ran , Qingpei Liu , Wenjing Wang , Xiaolong Yang

Cultivation of the endophytic fungus Robillarda sessilis XL-308 with SAHA resulted in the discovery of two previously undescribed cyclonerane sesquiterpenes (1 and 2), one previously unreported norcadinane type sesquiterpene (3), and seven suberanilohydroxamic acid (SAHA) derivatives (4–10). The identification of previously undescribed compounds was confirmed through NMR spectroscopic analyses, quantum chemistry calculations, and single-crystal X-ray crystallography. Among them, compounds 1 and 2 were products of the silenced genome in XL-308 that activated by SAHA. Concurrently, SAHA underwent biotransformation because of its moderate toxicity towards this fungus. It was hypothesized that the hydroxamic acid group in SAHA triggering the self-defense mechanism of XL-308 and converting SAHA into a less toxic derivative 5.

通过用 SAHA 培养内生真菌 Robillarda sessilis XL-308，发现了两种以前未曾报道过的环戊烷类倍半萜（1 和 2）、一种以前未曾报道过的去甲丁烷类倍半萜（3）和七种亚伯兰羟肟酸（SAHA）衍生物（4-10）。通过核磁共振光谱分析、量子化学计算和单晶 X 射线晶体学研究，确认了以前未曾报道过的化合物。其中，化合物 1 和 2 是 XL-308 中被 SAHA 激活的沉默基因组的产物。同时，由于 SAHA 对该真菌具有中等毒性，因此会发生生物转化。据推测，SAHA 中的羟肟酸基团触发了 XL-308 的自我防御机制，并将 SAHA 转化为毒性较低的衍生物 5。

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引用次数: 0

Aculeanoids A–D, the second 17-nor fusicoccane diterpenoids with immunosuppressive activity from Aspergillus aculeatus

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry

Pub Date : 2025-01-21 DOI: 10.1016/j.phytochem.2025.114414

Fei Liu , Qin Li , Yongqi Li , Hong Liao , Weiguang Sun , Jianguo Li , Chunmei Chen , Yonghui Zhang , Hucheng Zhu

Chemical investigation on the secondary metabolites of Aspergillus aculeatus led to the identification of ten modified fusicoccane-type diterpenoids aculeanoids A–J (1–10). Their structures and absolute configurations were characterized by comprehensive spectroscopic analysis, DP4+ analysis, Mo₂(OAc)₄-induced ECD, single-crystal X-ray diffractions, and ECD calculations. Compounds 1–4 belong to a rare class of 17-nor fusicoccane diterpenoids, with only one previously reported example. Biologically, compounds 6, 7, and 10 exhibited significant immunosuppressive activities against con A-induced T cell proliferation with IC₅₀ values ranging from 2.44 to 5.26 μM and LPS-induced B cell proliferation with IC₅₀ values ranging from 4.18 to 5.78 μM, which provided more possibilities with the treatment of organ transplantation and various autoimmune diseases.

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引用次数: 0

Aspergixanthones L−T, nine undescribed prenylxanthone derivatives from Aspergillus stellatus

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry

Pub Date : 2025-01-20 DOI: 10.1016/j.phytochem.2025.114413

Yu Liang , Xuanni Chen , Qin Li , Ziming Zhao , Hao Wang , Qingyi Tong , Weiguang Sun , Hucheng Zhu , Yongji Lai , Chunmei Chen , Yonghui Zhang

Nine undescribed prenylxanthone derivatives, aspergixanthones L−T (1−9), were isolated from the fungus Aspergillus stellatus. Compound 4 represents the first propionylated prenylxanthone, while compounds 7−9 are the first examples of prenylxanthones adorned with a 2,3-butanediol group. Their structures with absolute configurations were elucidated based on comprehensive spectroscopic analyses, ECD calculation, single-crystal X-ray diﬀraction, Mo₂(OAc)₄ induced ECD experiment, and Mosherʼs method. Compound 9 showed cytotoxic effects against several human cancer cell lines with the IC₅₀ values ranging from 3.35 ± 0.58 to 8.62 ± 1.18 μM. Compounds 7 and 8 showed suppressive effects on NO production with IC₅₀ values of 7.30 ± 0.69 and 5.16 ± 0.17 μM, respectively.

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引用次数: 0

Discovery and configurations assignment of Ile/Leu-containing cyclic peptides with cytotoxic activity, Reniochpeptins A–D, from the marine sponge Reniochalina sp.

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry

Pub Date : 2025-01-20 DOI: 10.1016/j.phytochem.2025.114412

Shuai-Shuai Zhang , Zong-Mei Wu , Ying Wu , Ya-Jun Zeng , Yuan-Yuan Zhang , Xin-Li Lin , Si Zhang , Kai-Xuan Zhan , Hou-Wen Lin , Shu-Ping Wang

Four previously undescribed cyclic peptides, reniochpeptins A–D (1–4), were isolated from the marine sponge Reniochalina sp. Their structures were elucidated through comprehensive spectroscopic analyses and a modified advanced Marfey's method. This method utilized ultra-high-performance liquid chromatography coupled with tandem multiple reaction monitoring mass spectrometry, employing a CORTECS T₃ column to achieve simultaneous separation of derivatized _L-Leu, _L-Ile, _L-allo-Ile, _D-Leu, _D-Ile, and _D-allo-Ile within 25 min in a single analytical run. Reniochpeptin A displayed moderate inhibitory activity against NCI–H460 cells, with an IC₅₀ value of 4.7 μM, by inducing cell cycle arrest at the G2/M phase and promoting apoptosis.

引用次数: 0

Chromones from Saposhnikovia divaricata and their inhibition of IL-1β-induced proliferative activity in SW982 cells 三叶草色素及其对il -1β诱导的SW982细胞增殖活性的抑制作用。

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry

Pub Date : 2025-01-18 DOI: 10.1016/j.phytochem.2025.114408

Yan Liu , Junnan Li , Yan Sun , Juan Pan , Yumeng Luo , Wei Guan , Qingshan Chen , Lili Zhang , Anam Naseem , Haixue Kuang , Bingyou Yang

Nine previously undescribed chromones, named sadivamones O–W (1–9), and five known analogues (10–14), were isolated from the roots of Saposhnikovia divaricata (Turcz.) Schischk. The detailed structural analysis of each compound was finalized by a variety of methods including NMR (1D and 2D), mass spectrometry (HR-ESI-MS) spectroscopic data, and sugar hydrolysis. The absolute configurations of compounds (4–5) were determined by CD. Moreover, compounds 1–14 were evaluated for their inhibition of IL-1β-induced proliferative activity in SW982 cells. The results demonstrated that compounds 2–4 and 11–12 exhibited notable inhibitory effects on IL-1β-induced proliferation in a concentration-dependent manner, with the most pronounced inhibition observed at a concentration of 20 μM.

9个先前未被描述的色素，命名为sadivamones O-W（1-9）和5个已知的类似物（10-14），从Saposhnikovia divaricata （Turcz）的根中分离出来。Schischk。通过核磁共振（1D和2D）、质谱（HR-ESI-MS）光谱数据和糖水解等多种方法，对每种化合物进行了详细的结构分析。通过CD测定化合物（4 ~ 5）的绝对构型，并评价化合物1 ~ 14对il -1β诱导的SW982细胞增殖活性的抑制作用。结果表明，化合物2-4和11-12对il -1β诱导的细胞增殖具有明显的抑制作用，且呈浓度依赖性，在浓度为20 μM时抑制效果最明显。

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引用次数: 0

Flavonoid glycosides in Lepidium sativum seeds and their bioactivities 枸杞种子中黄酮类苷类及其生物活性研究。

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry

Pub Date : 2025-01-18 DOI: 10.1016/j.phytochem.2025.114410

Yergazy Shybyray , Liu Liu , Haiqing Zhao , Jun Li , Haji Akber Aisa

Twelve flavonoid glycosides including five undescribed ones, lepisativutimines Q−U, were isolated and identified from Lepidium sativum seeds. Acid hydrolysis followed by acetic derivatization and GC analysis were conducted to determine the absolute configurations for sugars. Lepisativutimine U and beitingxinhuangtong A were uncommon kaempferol 8-S-glycosides, and complete NMR data of beitingxinhuangtong A were provided for the first time. Mass fragmentation pathways of isolated compounds were deduced based on their MS/MS data, and characteristic mass fragmentation patterns were summarized. Lepisativutimine U and kaempferol-7-O-α-l-rhamnopyranoside exhibited weak anti-diabetic activity against PTP1B with IC₅₀ values of 60.58 ± 3.53 and 33.90 ± 2.89 μM, respectively, quercetin-7-O-α-l-rhamnopyranoside displayed significant anti-diabetic activity against α-glucosidase with an IC₅₀ value of 25.96 ± 0.30 μM, and kaempferol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-galactopyranoside-7-O-α-l-rhamnopyranoside and kaempferol-7-O-α-l-rhamnopyranoside showed weak inhibitory activity against NO release in LPS-induced RAW264.7 cells with IC₅₀ values of 92.28 ± 4.19 and 40.77 ± 1.50 μM, respectively.

从Lepidium satium种子中分离鉴定了12种黄酮类苷，其中5种为未描述的lepisativatimine Q-U。通过酸水解、乙酸衍生化和气相色谱分析确定糖的绝对构型。麻草碱U和北京新黄通A是少见的山奈酚8- s苷类化合物，首次获得了北京新黄通A的完整NMR数据。根据分离化合物的质谱/质谱数据，推导了分离化合物的质谱裂解途径，总结了分离化合物的质谱裂解模式。槲皮素-7- o -α-l-鼠李糖苷对α-葡萄糖苷酶的IC50值为25.96±0.30 μM，槲皮素-7- o -α-l-鼠李糖苷对PTP1B的IC50值为60.58±3.53 μM，山奈酚-7- o -α-l-鼠李糖苷对α-葡萄糖苷酶的IC50值为33.90±2.89 μM。山奈酚3-O-β-d-葡萄糖吡喃糖基-(1→2)-β-d-半乳糖吡喃苷-7- o -α-l-鼠李糖苷和山奈酚7- o -α-l-鼠李糖苷对lps诱导的RAW264.7细胞NO释放的抑制作用较弱，IC50值分别为92.28±4.19 μM和40.77±1.50 μM。

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引用次数: 0

Triterpenoid saponins from Rubus setchuenensis roots and their anti-inflammatory activities in vitro 荆芥根中三萜皂甙及其体外抗炎活性研究。

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry

Pub Date : 2025-01-18 DOI: 10.1016/j.phytochem.2025.114403

Yueyue Lei , Dawei Xu , Yuexuan Wang , Shiwen Guo , Lujun Li , Mengyin Luo , Xu Li , Xinyi Liu , Chunyang Shi

Previously undescribed triterpenoid saponins (1–8), along with eight previously reported analogues (9–16), were isolated from an EtOAc extract obtained from the roots of Rubus setchuenensis. Structures were established based on HRESIMS, 1D and 2D NMR, as well as by literature comparisons. All compounds were isolated for the first time from the genus Rubus. Compounds 3–4, 6–8, and 12–15 displayed inhibitory activities against NO production in a RAW264.7 cell inflammation model induced by LPS. Moreover, 4, 6–8, and 12–13 exhibited inhibitory effects in a LPS-induced BV-2 cell neuroinflammation model.

先前未被描述的三萜皂苷（1-8），以及8个先前报道的类似物（9-16），从从山茱萸根中获得的乙酸乙酯提取物中分离出来。通过hremsims、1D和2D NMR以及文献比较，建立了结构。所有化合物均为首次从该属植物中分离得到。在LPS诱导的RAW264.7细胞炎症模型中，化合物3-4、6-8和12-15显示出抑制NO生成的活性。此外，4、6-8和12-13在lps诱导的BV-2细胞神经炎症模型中表现出抑制作用。

引用次数: 0

Artemyriantholidimers A-G, undescribed guaiane-type sesquiterpenoid dimers from Artemisia myriantha and their antihepatoma activities 青蒿素二聚体A-G，描述了从豆花蒿中提取的瓜蓝烷型倍半萜二聚体及其抗肝癌活性。

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry

Pub Date : 2025-01-16 DOI: 10.1016/j.phytochem.2025.114409

Meng-Fei Wang , Tian-Ze Li , Yun-Bao Ma , Yong-Cui Wang , Qi-Hao Li , Feng-Jiao Li , Ji-Jun Chen

Artemyriantholidimers A-G (1–7), seven undescribed guaiane-type sesquiterpenoid dimers (GSDs), and 27 known compounds (8–34) were isolated from Artemisia myriantha (Asteraceae). Their structures and relative configurations were elucidated based on the comprehensive analyses of UV, IR, MS, NMR data, quantum chemical NMR calculations with DP4+ probability analyses, and the absolute configurations were elucidated by ECD calculations. The undescribed GSDs (1–7) were presumably formed via Diels-Alder reactions, and compounds 5–7 were rare GSDs with α-configuration of H-6'. Compounds 4–7 showed significant inhibition on HepG2, Huh7, and SK-Hep-1 cells with IC₅₀ values ranging from 6.9 to 13.0 μM by antihepatoma assay. The best active compound 5 was deduced to be targeted on the protein AURKA of the p53 signaling pathway by network pharmacological analysis with a high bind affinity of AURKA (total score: −8.98) by molecular docking, and had a K_D value of 62.4 μM by surface plasmon resonance assay.

从紫花蒿（Asteraceae）中分离到青蒿素二聚体A-G（1-7）、7个未被描述的瓜蓝烷型倍半萜二聚体（gsd）和27个已知化合物（8-34）。通过紫外、红外、质谱、核磁共振数据的综合分析，利用DP4+概率分析进行量子化学核磁共振计算，确定了它们的结构和相对构型，并用ECD计算确定了它们的绝对构型。所描述的GSDs（1-7）可能是通过Diels-Alder反应形成的，化合物5-7是罕见的具有H-6' α-构型的GSDs。化合物4 ~ 7对HepG2、Huh7和SK-Hep-1细胞有明显的抑制作用，IC50值在6.9 ~ 13.0 μM之间。通过网络药理学分析推断出最佳活性化合物5为p53信号通路蛋白AURKA，通过分子对接发现AURKA具有较高的结合亲和力（总分为-8.98），表面等离子体共振测定KD值为62.4 μM。

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引用次数: 0

Five undescribed chromone-phenylpyridone hybrids from Cineraria repanda-derived Penicillium oxalicum with cytotoxic and antibacterial activity 五种未描述的具有细胞毒性和抗菌活性的绿灰青霉-苯吡啶酮杂合体。

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry

Pub Date : 2025-01-16 DOI: 10.1016/j.phytochem.2025.114407

Yu Wei Huang , Jing Guan , Yin Tang , Ren Xiang Tan , Li Ping Lin

Five previously undescribed phenylpyridones, designated as citridones H–L (1–5), along with seven known compounds, were characterized from the rice medium culture of the Cineraria repanda-derived endophytic fungus Penicillium oxalicum. Their structures were elucidated through detailed interpretation of UV, NMR, and HR-ESI-MS data. The absolute configurations of C-2 and C-3 in compounds 1–4 were determined by spectroscopic analysis and ECD calculations, while the C-5′ configurations were established through computational ¹³C NMR and DP4+ analyses. These compounds represent a novel scaffold of chromone-phenylpyridone hybrids, making only the second report of such compounds from the Penicillium genus and the first to feature a unique (E)-5-methylhepta-1,3-diene group at the C-2 position. Additionally, a biosynthetic pathway for these novel chromone-phenylpyridones is proposed for the first time. Notably, compounds 3 and 4 exhibited cytotoxicity against HCT116 and H1299 cell lines when used in combination, with IC₅₀ values of 4.15 ± 0.34 and 9.07 ± 1.64 μM, respectively. Furthermore, compounds 3, 4 and 5 demonstrated significant inhibitory effects against Staphylococcus aureus, with MIC values of 64, 64 and 8 μg/mL, respectively.

5个先前未被描述的苯吡啶酮，被命名为柠檬酸酮H-L(1-5)，以及7个已知化合物，从金针菇来源的内生真菌青霉草的水稻培养基中鉴定出来。通过对UV、NMR和HR-ESI-MS数据的详细解释，阐明了它们的结构。化合物1-4中C-2和C-3的绝对构型通过光谱分析和ECD计算确定，C-5的构型通过计算13C NMR和DP4+分析确定。这些化合物代表了一种新的铬-苯基吡啶酮杂交体支架，这是青霉菌属中第二次报道这类化合物，也是第一次在C-2位置上具有独特的(E)-5-甲基庚-1,3-二烯基团。此外，本文还首次提出了这些新型铬-苯吡啶酮的生物合成途径。值得注意的是，化合物3和4在与HCT116和H1299细胞株联合使用时表现出细胞毒性，IC50值分别为4.15±0.34和9.07±1.64 μM。此外，化合物3、4和5对金黄色葡萄球菌具有显著的抑制作用，其MIC值分别为64、64和8 μg/mL。

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