Why Do Plants Convert Sitosterol to Stigmasterol?

Aboobucker, Siddique I.; Suza, Walter

doi:10.3389/fpls.2019.00354

Cited by 91 publications

(55 citation statements)

References 98 publications

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“…Edible oils contain higher amount of stigmasterol than vegetables. It is widely used as food additives in food and beverage industries for production of sausages, yogurt, cold cuts, margarines, bakery products, milk and spreads (Aboobucker et al, 2019;Jun-Hua et al, 2008;Siddiqui et al, 1990). Stigmasterol is also used as a precursor or intermediate for synthesis of various human steroid hormones like progesterone, androgen corticoids, estrogens etc (Sundararaman and Djerassi, 1977;Hogg, 1992).…”

Section: Structure and Molecular Formula Of Isolated Compoundmentioning

confidence: 99%

Isolation and Characterization of Stigmasterol from Fritillaria roylei

et al. 2020

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Fritillaria roylei (Kshirakakoli) is the threatened species of “Ashtwarga” group suffers lot of confusion for identification & authentification in Ayurvedic system of medicine. Due to lack of natural sources and insufficient availability of kshirakakoli, chances of adulteration and substitution increases which in turn leads to loss of faith of people in herbal drugs. Thus for identification and differentiation, quality standardization and quality assurance of kshirakakoli containing herbal formulations there is a need to isolate chemical marker compound using advanced analytical techniques. The methanol extract of root samples of plant was prepared and phytochemical screening was performed. Marker compound was isolated from the extract using column chromatography. Single compound having Rf value 0.31 was isolated with TLC by using mobile phase n-hexane: ethyl acetate: formic acid (8:2:0.1 v/v/v) and purified by re-crystallization with methanol. Isolated compound was further characterized by using melting point and spectral analysis. The methanol extract was dark brown in color and showed the presence of steroids, amino acids and flavonoids. The isolated compound was found to be white crystalline powder with melting point range of 167-169°C. Spectral analysis confirmed the presence of Stigmasterol. In present study stigmasterol was isolated for the first time and can be used as chemical marker for identification and differentiation of the plant from its substitutes.

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Section: Structure and Molecular Formula Of Isolated Compoundmentioning

confidence: 99%

Isolation and Characterization of Stigmasterol from Fritillaria roylei

et al. 2020

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“…Stigmasterol (C 29 H 48 O), a naturally occurring steroid derivative, is found in many plants, such as Cabbage, Gypsophila oldhamiana, Arabidopsis , Aralia cordata, Eucalyptus globules, Physcomitrella patens , etc 11,12. Chemical structure of stigmasterol is shown in Figure 1A.…”

Section: Introductionmentioning

confidence: 99%

<p>Stigmasterol Exerts Neuro-Protective Effect Against Ischemic/Reperfusion Injury Through Reduction Of Oxidative Stress And Inactivation Of Autophagy</p>

Sun¹,

Li²,

Liu³

et al. 2019

NDT

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PurposeStroke remains the primary cause of pain, suffering, and death in patients. One of the major thrusts in stroke therapy is to find an effective prevention strategy. Objectives of this study are to testify the neuro-protection effect of stigmasterol in ischemic/reperfusion injury model.MethodsThe dosage-dependent effects (20, 40, and 80 mg/kg) of stigmasterol on physiological behaviors and oxidative stress biomarkers were investigated. Expression and phosphorylation of beclin1, microtubule-associated protein 1 light chain 3 (LC3), adenosine monophosphate-activated protein kinase (AMPK), mTOR, and N-terminal kinase (JNK) were detected.ResultsThe results showed that stigmasterol was able to effectively reduce neurological deficits and infarct damage induced by the ischemic/reperfusion injury, improve histopathology changes, and restore the levels of the endogenous antioxidant defense system in a dose–response mode. Stigmasterol effectively depressed the expression level of beclin1, and the conversion of LC3 I to LC3 II, while promoted the phosphorylation of mTOR, and remarkably inhibited the phosphorylation of AMPK and JNK, as well as the expression of JNK induced by 24 hrs of reperfusion.ConclusionThese findings reveal that stigmasterol has neuro-protective effect against the ischemic/reperfusion injury, possibly associated with reduction of oxidative stress and inactivation of autophagy via AMPK/mTOR and JNK pathways.

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“…Stigmasterol-enriched membranes are less permeable and, therefore, show a decreased leakage (9,10). Therefore, the level of β-stigmasterol in the PM is expected to be tightly regulated during plant development and stress responses (11)(12)(13).…”

Section: Introductionmentioning

confidence: 99%

“…Stigmasterol is the end product of the 24-ethyl branch of the sterol biosynthetic pathway and is synthesized from β-sitosterol by the action of the enzyme sterol C22 desaturase (C22DES) ( Fig. 1) (11,14). C22DES, also known as CYP710, belongs to the cytochrome P450 (CYP) protein family, which includes enzymes involved in numerous biosynthetic and xenobiotic pathways in all living organisms.…”

Section: Introductionmentioning

confidence: 99%

“…Other important aspects related with the characterization of C22DES are the identi cation of structural and functional motifs involved in the intracellular targeting of the enzyme as well as in its membrane topology and catalytic function. Some of these issues have been addressed in the present work using tomato C22DES, which was chosen for this study not only because this plant is one of the most important crops worldwide but also because, in contrast to other plant species, tomato contains a single gene coding for this enzyme (11,17).…”

Section: Introductionmentioning

confidence: 99%

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Structural and Functional Analysis of Tomato Sterol C22 Desaturase

Gutiérrez-García

Arró

Altabella

et al. 2020

Preprint

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Background: Sterols are essential components of eukaryotic cells that modulate membrane biophysical properties and function. Plants produce a complex mixture of sterols, among which β-sitosterol, stigmasterol, campesterol, and cholesterol in some Solanaceae, are the most abundant species. Many reports have shown that the stigmasterol to β-sitosterol ratio changes during plant development and in response to stresses, suggesting that it may play a role in the regulation of these processes. In tomato (Solanum lycopersicum), changes in the stigmasterol to β-sitosterol ratio correlate with the induction of the only gene encoding sterol C22-desaturase (C22DES), the enzyme specifically involved in the conversion of β-sitosterol to stigmasterol. However, despite the biological interest of this enzyme, there is still a lack of knowledge about several relevant aspects related to its structure and function.Results: In this study we report the subcellular localization of tomato C22DES in the endoplasmic reticulum (ER) based on confocal fluorescence microscopy and cell fractionation analyses. Modeling studies have also revealed that C22DES consists of two well-differentiated domains: a single N-terminal transmembrane-helix domain (TMH) anchored in the ER-membrane and a globular (or catalytic) domain that is oriented towards the cytosol. Although TMH is sufficient for the targeting and retention of the enzyme in the ER, the globular domain may also interact and be retained in the ER in the absence of the N-terminal transmembrane domain. The observation that a truncated version of C22DES lacking the TMH is enzymatically inactive revealed that the N-terminal membrane domain is essential for enzyme activity. The in silico analysis of the TMH region of plant C22DES revealed several structural features that could be involved in substrate recognition and binding.Conclusions: Overall, this study contributes to expand the current knowledge on the structure and function of plant C22DES and to unveil novel aspects related with plant sterol metabolism.

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Why Do Plants Convert Sitosterol to Stigmasterol?

Cited by 91 publications

References 98 publications

Isolation and Characterization of Stigmasterol from Fritillaria roylei

Isolation and Characterization of Stigmasterol from Fritillaria roylei

<p>Stigmasterol Exerts Neuro-Protective Effect Against Ischemic/Reperfusion Injury Through Reduction Of Oxidative Stress And Inactivation Of Autophagy</p>

Structural and Functional Analysis of Tomato Sterol C22 Desaturase

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