Bioactive abietenolide diterpenes from Suregada procera

IF 2.6 3区医学 Q3 CHEMISTRY, MEDICINAL Fitoterapia Pub Date : 2024-12-01 Epub Date: 2024-09-18 DOI:10.1016/j.fitote.2024.106217

Jackson Obegi Matundura , Jackson T. Mollel , Masum Miah , Joanna Said , Leonidah K. Omosa , Thobias M. Kalenga , Yannik T. Woordes , Vaderament-Alexe Nchiozem-Ngnitedem , Andreas Orthaber , Jacob O. Midiwo , Wouter Herrebout , Edward Trybala , Tomas Bergström , Luis Apaza Ticona , Mate Erdelyi , Abiy Yenesew

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Abstract

The phytochemical investigation of the leaves and the roots of Suregada procera afforded the new ent-abietane diterpenoid sureproceriolide A (1) along with the known secondary metabolites 8,14β:11,12α-diepoxy-13(15)-abietane-16,12-olid (2), jolkinolide A (3), jolkinolide E (4), ent-pimara-8(14),15-dien-19-oic acid (5), sitosterol (6), oleana-9(11):12-dien-3β-ol (7), and oleic acid (8). Their structures were elucidated by NMR spectroscopic and mass spectrometric analyses, and the structure of jolkinolide A (3) was confirmed by single-crystal X-ray diffraction analysis. Sureproceriolide A (1) showed modest activity against the Gram-positive bacterium Staphylococcus lugdunensis (MIC = 31.44 μM), and sitosterol (6) against the Gram-negative bacterium Porphyromonas gingivalis (IC₅₀ = 45.37 μM). Jolkinolide A (3) and E (4) as well as sitosterol (6) inhibited the release of NOS (IMR-90 cells), TNF-α (HaCaT cells) and NF-κB (HaCaT cells), with IC₅₀ values of 0.43, 3.21, and 10.32 μM, respectively. Compound 6 showed antitumoral activity against SK-MEL-28 (IC₅₀ = 20.66 μM) and CCD-13Lu (IC₅₀ = 24.70 μM) cell lines, with no cytotoxic effect against the prostate cells PrEC (CC₅₀ > 300 μM).

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来自 Suregada procera 的具有生物活性的 Abietenolide 二萜。

对 Suregada procera 的叶和根进行的植物化学研究发现了新的内阿比坦二萜类物质 sureproceriolide A (1)，以及已知的次生代谢物 8,14β：11,12α-diepoxy-13(15)-abietane-16,12-olid (2)、jolkinolide A (3)、jolkinolide E (4)、ent-pimara-8(14),15-dien-19-oic acid (5)、sitosterol (6)、oleana-9(11):12-dien-3β-ol (7) 和 oleic acid (8)。核磁共振光谱和质谱分析阐明了它们的结构，单晶 X 射线衍射分析证实了金丝桃内酯 A（3）的结构。Sureproceriolide A（1）对革兰氏阳性菌卢格杜氏葡萄球菌（MIC = 31.44 μM）显示出适度的活性，而 sitosterol（6）对革兰氏阴性菌牙龈卟啉单胞菌（IC50 = 45.37 μM）显示出适度的活性。Jolkinolide A（3）和 E（4）以及西坦醇（6）可抑制 NOS（IMR-90 细胞）、TNF-α（HaCaT 细胞）和 NF-κB （HaCaT 细胞）的释放，其 IC50 值分别为 0.43、3.21 和 10.32 μM。化合物 6 对 SK-MEL-28 细胞株（IC50 = 20.66 μM）和 CCD-13Lu 细胞株（IC50 = 24.70 μM）具有抗肿瘤活性，而对前列腺细胞 PrEC（CC50 > 300 μM）没有细胞毒性作用。

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来源期刊

Fitoterapia 医学-药学

CiteScore

5.80

自引率

2.90%

发文量

198

审稿时长

1.5 months

期刊介绍： Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas: 1. Characterization of active ingredients of medicinal plants 2. Development of standardization method for bioactive plant extracts and natural products 3. Identification of bioactivity in plant extracts 4. Identification of targets and mechanism of activity of plant extracts 5. Production and genomic characterization of medicinal plants biomass 6. Chemistry and biochemistry of bioactive natural products of plant origin 7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.