Suppr超能文献

从丹参中分离得到的贝壳杉烷和伊卡烷二萜的结构、绝对构型和抗增殖活性。

Structure, Absolute Configuration, and Antiproliferative Activity of Abietane and Icetexane Diterpenoids from Salvia ballotiflora.

机构信息

Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Circuito Exterior, Ciudad Universitaria, Mexico City 04510, Mexico.

Facultad de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Mexico City 04510, Mexico.

出版信息

Molecules. 2017 Oct 18;22(10):1690. doi: 10.3390/molecules22101690.

Abstract

From the aerial parts of , eleven diterpenoids were isolated; among them, four icetexanes and one abietane (-) are reported for the first time. Their structures were established by spectroscopic means, mainly ¹H- and C-NMR, including 1D and 2D homo- and hetero-nuclear experiments. Most of the isolated diterpenoids were tested for their antiproliferative, anti-inflammatory, and radical scavenging activities using the sulforhodamine B assay on six cancer cell lines, the TPA-induced ear edema test in mice, and the reduction of the DPPH assay, respectively. Some diterpenoids showed anti-proliferative activity, these being icetexanes and , which were the most active with IC (μM) = 0.27 ± 0.08 and 1.40 ± 0.03, respectively, for U251 (human glioblastoma) and IC (μM) = 0.0.46 ± 0.05 and 0.82 ± 0.06 for SKLU-1 (human lung adenocarcinoma), when compared with adriamycin (IC (μM) = 0.08 ± 0.003 and 0.05 ± 0.003, as the positive control), respectively. Compounds and showed significant reduction of the induced ear edema of 37.4 ± 2.8 and 25.4 ± 3.0% (at 1.0 μmol/ear), respectively. Compound was the sole active diterpenoid in the antioxidant assay (IC = 98. 4 ± 3.3), using α-tocopherol as the positive control (IC (μM) = 31.7 ± 1.04). The diterpenoid profile found is of chemotaxonomic relevance and reinforces the evolutionary link of with other members of the section Tomentellae.

摘要

从 的地上部分分离得到 11 个二萜类化合物;其中,4 个异冷杉烷和 1 个枞烷(-)为首次报道。通过光谱学手段,主要是 ¹H-NMR 和 C-NMR,包括 1D 和 2D 同核和异核实验,确定了它们的结构。大多数分离得到的二萜类化合物都进行了抗增殖、抗炎和自由基清除活性测试,采用六株癌细胞系的磺酰罗丹明 B 测定法、小鼠 TPA 诱导的耳肿胀试验和 DPPH 还原法分别进行。一些二萜类化合物表现出抗增殖活性,其中异冷杉烷 和 最为活跃,对 U251(人胶质母细胞瘤)的 IC(μM)分别为 0.27 ± 0.08 和 1.40 ± 0.03,对 SKLU-1(人肺腺癌)的 IC(μM)分别为 0.0.46 ± 0.05 和 0.82 ± 0.06,与阿霉素(IC(μM)= 0.08 ± 0.003 和 0.05 ± 0.003,作为阳性对照)相比。化合物 和 对诱导的耳肿胀的抑制作用分别为 37.4 ± 2.8% 和 25.4 ± 3.0%(在 1.0 μmol/耳)。化合物 是唯一具有抗氧化活性的二萜类化合物(IC = 98.4 ± 3.3),以 α-生育酚作为阳性对照(IC(μM)= 31.7 ± 1.04)。所发现的二萜类化合物图谱具有化学生态学相关性,并加强了 与其他 Tomentellae 成员之间的进化联系。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2be/6151488/700c88204d1e/molecules-22-01690-g001.jpg

相似文献

4
Cytotoxic abietane diterpenoids from Salvia leriifolia Benth.
Phytochemistry. 2022 Oct;202:113310. doi: 10.1016/j.phytochem.2022.113310. Epub 2022 Jul 19.
5
Antiproliferative abietane quinone diterpenoids from the roots of Salvia deserta.
Bioorg Chem. 2020 Nov;104:104261. doi: 10.1016/j.bioorg.2020.104261. Epub 2020 Sep 3.
6
Structurally Diverse Diterpenoids from the Roots of Based on Nine Different Skeletal Types.
J Nat Prod. 2021 May 28;84(5):1442-1452. doi: 10.1021/acs.jnatprod.0c01180. Epub 2021 May 12.
7
Two New Abietane Diterpenoids from Selaginella moellendorffii Hieron.
Chem Biodivers. 2020 Jun;17(6):e2000111. doi: 10.1002/cbdv.202000111. Epub 2020 May 7.
8
Isolation and bioactivity of diterpenoids from the roots of Salvia grandifolia.
Phytochemistry. 2015 Aug;116:337-348. doi: 10.1016/j.phytochem.2015.03.014. Epub 2015 Apr 22.
10
Cytotoxic abietane-type diterpenoids from roots of and their pharmacophore modeling.
Nat Prod Res. 2022 Jun;36(12):3183-3188. doi: 10.1080/14786419.2021.1952202. Epub 2021 Jul 22.

引用本文的文献

1
Promising leads against lung cancer from the plants in Lamiaceae family.
Bioimpacts. 2024 Jun 8;15:30074. doi: 10.34172/bi.30074. eCollection 2025.
4
Recent Developments with Icetexane Natural Products.
Chem Biodivers. 2022 Nov;19(11):e202200793. doi: 10.1002/cbdv.202200793. Epub 2022 Nov 8.
6
New Diterpenes with Potential Antitumoral Activity Isolated from Plants in the Years 2017-2022.
Plants (Basel). 2022 Aug 29;11(17):2240. doi: 10.3390/plants11172240.
8
A Review on the Ethnopharmacology and Phytochemistry of the Neotropical Sages ( Subgenus ; Lamiaceae) Emphasizing Mexican Species.
Front Pharmacol. 2022 Apr 19;13:867892. doi: 10.3389/fphar.2022.867892. eCollection 2022.

本文引用的文献

1
Absolute configuration of the diterpenoids icetexone and conacytone from Salvia ballotaeflora.
Chirality. 2018 Feb;30(2):177-188. doi: 10.1002/chir.22781. Epub 2017 Nov 7.
2
Collective Syntheses of Icetexane Natural Products Based on Biogenetic Hypotheses.
Chemistry. 2017 Jan 1;23(1):120-127. doi: 10.1002/chem.201603932. Epub 2016 Nov 29.
4
Composition of the Essential Oil of Salvia ballotiflora (Lamiaceae) and Its Insecticidal Activity.
Molecules. 2015 May 5;20(5):8048-59. doi: 10.3390/molecules20058048.
5
Aromatic abietane diterpenoids: their biological activity and synthesis.
Nat Prod Rep. 2015 May;32(5):684-704. doi: 10.1039/c4np00110a.
6
Vibrational circular dichroism absolute configuration determination of natural products.
Prog Chem Org Nat Prod. 2015;100:311-452. doi: 10.1007/978-3-319-05275-5_4.
7
Antioxidant activity and mechanism of the abietane-type diterpene ferruginol.
Nat Prod Res. 2015;29(18):1739-43. doi: 10.1080/14786419.2014.997233. Epub 2015 Jan 14.
8
Multiple pro-apoptotic targets of abietane diterpenoids from Salvia species.
Fitoterapia. 2015 Jan;100:118-32. doi: 10.1016/j.fitote.2014.11.008. Epub 2014 Nov 15.
9
Synthesis and κ-opioid receptor activity of furan-substituted salvinorin A analogues.
J Med Chem. 2014 Dec 26;57(24):10464-75. doi: 10.1021/jm501521d. Epub 2014 Dec 9.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验