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Sterols and Triterpenes from Dobera glabra Growing in Saudi Arabia and Their Cytotoxic Activity.

ABSTRACT: A new lupane caffeoyl ester, lup-20(29)-ene 3?-caffeate-30-al (7), and a new oleanane-type triterpene, 3?-hydroxyolean-13(18)-en-12-one (17), were isolated from the aerial parts of Dobera glabra (Forssk), along with ten known triterpenes, including seven lupane-type lupeol (1), 30-nor-lup-3?-ol-20-one (2), ?¹-lupenone (3), lup-20(29)-en-3?,30-diol (4), lupeol caffeate (5), 30-hydroxy lup-20(29)-ene 3?-caffeate (6), and betunaldehyde (8); three oleanane-type compounds were also identified, comprising ?-amyrone (15), ?-amyrin (16), and 11-oxo-?-amyrin (18); together with six sterols, comprising ?-sitosterol (9), stigmasterol (10), 7?-hydroxy-?-sitosterol (11), 7?-hydroxy-stigmasterol (12), 7-keto-?-sitosterol (13), and 7-keto-stigmasterol (14). Their structures were elucidated using a variety of spectroscopic techniques, including 1D (¹H, ¹³C, and DEPT-135 ¹³C) and 2D (¹H-¹H COSY, ¹H-¹³C HSQC, and ¹H-¹³C HMBC) nuclear magnetic resonance (NMR) and accurate mass spectroscopy. Subsequently, the different plant extracts and some of the isolated compounds (1-9, 11 and 13) were investigated for their possible cytotoxic activity in comparison to cisplatin against a wide array of aggressive cancer cell lines, such as colorectal cancer (HCT-116), hepatocellular carcinoma (HepG-2), and prostate cancer (PC-3) cell lines. Compound 11 displayed broad cytotoxicity against all of the tested cell lines (IC₅₀ ? 8 µg/mL in all cases), and a high safety margin against normal Vero cells (IC₅₀ = 70 µg/mL), suggesting that 11 may be a highly selective and effective anticancer agent candidate. Notably, the evidence indicated that the mode of action of compound 11 could possibly consist of the inhibition of phosphodiesterase I (80.2% enzyme inhibition observed at 2 µM compound concentration).

SUBMITTER: Abdel-Mageed WM

PROVIDER: S-EPMC7827382 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Sterols and Triterpenes from Dobera glabra Growing in Saudi Arabia and Their Cytotoxic Activity.

Abdel-Mageed Wael M WM El-Gamal Ali A AA Al-Massarani Shaza M SM Basudan Omer A OA Badria Farid A FA Abdel-Kader Maged S MS Al-Rehaily Adnan J AJ Aati Hanan Y HY

Plants (Basel, Switzerland) 20210108 1

A new lupane caffeoyl ester, lup-20(29)-ene 3β-caffeate-30-al (7), and a new oleanane-type triterpene, 3β-hydroxyolean-13(18)-en-12-one (17), were isolated from the aerial parts of Dobera glabra (Forssk), along with ten known triterpenes, including seven lupane-type lupeol (1), 30-nor-lup-3β-ol-20-one (2), ∆1-lupenone (3), lup-20(29)-en-3β,30-diol (4), lupeol caffeate (5), 30-hydroxy lup-20(29)-ene 3β- ...[more]

PMID: 33430053

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Project description:The use of wild plants is considered to be an eco-friendly and promising natural resource. In sandy desert habitats, Leptadenia pyrotechnica flourishes as a xerophytic shrub with high biomass production. As a dominant shrub in the arid sand dune habitats of Saudi Arabia, Leptadenia pyrotechnica (Forssk.) Decne (Asclepiadaceae) is one of the most common xerophytes; the many medicinal uses of this plant include treating allergies, productive coughs, abortions, diabetes, stomach disorders, fevers, kidney disorders, and stones. In such a distribution, morpho-anatomical characteristics, among other adaptive traits, play an important role. This study aims to characterize some morpho-anatomical adaptations of L. pyrotechnica in two stressful habitats: the hyper-arid inland sand dunes of the Empty Quarter (EQ) and the arid coastal sand dunes of Jazan. A morpho-anatomical analysis of plant stems and roots from both habitats was conducted using light microscopy (LM) and scanning electron microscopy (SEM). The outcomes indicated similar characteristics, a low surface-to-volume ratio (S/V), a thin boundary layer (δbl), an epidermis with many layers of hypodermis, bundles of sclerenchymatous cells around vascular tissue, and storage starch grains in ray parenchyma between xylem conduits. On the other hand, the L. pyrotechnica stem from the hyper-arid habitat of the Empty Quarter revealed more encrypted stomata, more elongated palisade cells, less calcium oxalate crystals with low Ca percentage, and a high vulnerability index of xylem vessels compared with the same traits of the stem from the Jazan coastal sand dunes habitat. Roots of L. pyrotechnica from both habitats revealed similar features of general anatomy. However, differences in specific anatomical traits were observed, especially in xylem vessel characters. The vulnerability index of root xylem vessels from the Empty Quarter habitat was more than that from the Jazan coastal sand dunes habitat. Furthermore, vestured bordered pits in root xylem walls were more abundant in the Empty Quarter habitat than in the Jazan coastal sand dunes habitat. As a result, these characteristics in the morpho-anatomy of L. pyrotechnica from both habitats provide practical adaptations to highly stressful conditions, along with specific anatomical traits relating to each habitat.

Dataset Information

Sterols and Triterpenes from Dobera glabra Growing in Saudi Arabia and Their Cytotoxic Activity.

Publications

Sterols and Triterpenes from <i>Dobera glabra</i> Growing in Saudi Arabia and Their Cytotoxic Activity.

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