Immunosuppressive leucosceptrane-type sesterterpenoids with antipodal cyclopentenones isolated from Leucosceptrum canum

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Phytochemistry Pub Date : 2024-10-16 DOI:10.1016/j.phytochem.2024.114305

Kai Guo , Shi-Hong Luo , Yan-Chun Liu , Ting-Ting Zhou , Yan Liu , Sheng-Hong Li

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Abstract

Ten undescribed leucosceptrane-type sesterterpenoids with antipodal cyclopentenone moieties were isolated from the leaves of Leucosceptrum canum. Their structures including absolute configurations were elucidated by comprehensive spectroscopic analyses (including 1D and 2D NMR, and HRMS) and ECD calculations. In vitro immunosuppressive effects of these sesterterpenoids against the proliferation of T cells and the secretion of cytokine IFN-γ were evaluated. Among them, 11α-H-leucosceptroid C, 5,13-dehydro-11α-H-leucosceptroid C, 5,13-dehydro-11β-hydroxy-leucosceptroid C, and 5,13-dehydro-11α-hydroxy-leucosceptroid C significantly inhibited IFN-γ secretion with IC₅₀ values of 12.55–23.62 μM. More remarkable inhibitory effects against IFN-γ secretion were observed for 5,13-dehydro-11β-hydroxy-leucosceptroid D, leucosceptroid U, 14-epi-leucosceptroid U, leucosceptroid V, and 14-epi-leucosceptroid V, with IC₅₀ values of 4.32–9.47 μM.

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从 Leucosceptrum canum 中分离出的具有抗节环戊烯酮的免疫抑制性白花蛇舌草类酯萜类化合物。

从 Leucosceptrum canum 的叶子中分离出了十种未曾描述过的具有对偶环戊烯酮分子的 leucosceptrane-type sesterterpenoids。通过综合光谱分析（包括一维和二维核磁共振以及 HRMS）和 ECD 计算，阐明了它们的结构，包括绝对构型。评估了这些酯萜类化合物对 T 细胞增殖和细胞因子 IFN-γ 分泌的体外免疫抑制作用。其中 11α-H-leucosceptroid C、5,13-dehydro-11α-H-leucosceptroid C、5,13-dehydro-11β-hydroxy-leucosceptroid C 和 5,13-dehydro-11α-hydroxy-leucosceptroid C 能显著抑制 IFN-γ 的分泌，其 IC50 值为 12.55-23.62 μM。5,13-脱氢-11β-羟基-亮腺受体 D、亮腺受体 U、14-表-亮腺受体 U、亮腺受体 V 和 14-表-亮腺受体 V 对 IFN-γ 分泌的抑制作用更为明显，IC50 值为 4.32-9.47 μM。

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来源期刊

Phytochemistry 生物-植物科学

CiteScore

6.40

自引率

7.90%

发文量

443

审稿时长

39 days

期刊介绍： Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.

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