An alkyl-cysteine sulfoxide lyase in Tulbaghia violacea and its relation to other alliinase-like enzymes

Jacobsen, John V.; Yamaguchi, Yuko; Mann, Louis K.; Howard, Frank D.; Bernhard, Richard A.

doi:10.1016/s0031-9422(00)88255-2

Cited by 22 publications

(8 citation statements)

References 25 publications

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“…Although these compounds are corrosive, the ability of the thiosulfinate to ultimately inhibit the activity of the enzyme that initiates the cascade of reactions that result in their formation (i.e., alliinase) ensures reduced collateral damage. Our observations also may shed light on the heretofore unexplained finding in studies of Alliums and other plants such as onion ( Allium cepa ), − garlic ( Allium sativum ), , Tulbaghia violacea , and Albizzia lophantha ) that alliinases appear to be inactivated before all of the available cysteine sulfoxide substrate has been exhausted. Similar to what we observed in P. alliacea , the alliinases in these plants may be shut down shortly after their activation, by the thiosulfinates that are formed when there is a tissue breach, and this would result in much of the cysteine sulfoxide substrate remaining unreacted.…”

Section: Discussionsupporting

confidence: 51%

“…Although these compounds are corrosive, the ability of the thiosulfinate to ultimately inhibit the activity of the enzyme that initiates the cascade of reactions that result in their formation (i.e., alliinase) ensures reduced collateral damage. Our observations also may shed light on the heretofore unexplained finding in studies of Alliums and other plants such as onion (Allium cepa), 52−55 garlic (Allium sativum), 56,57 Tulbaghia violacea, 56 Scheme 2. Outline of the Feedback Inhibition Loop Involving P. alliacea Alliinase a a Within seconds of wounding, the exposure of petiveriin to an alliinase/LFS complex results in rapid production of the highly irritating lachrymatory sulfine PMTSO, which causes long-lasting and severe irritation to the eyes, nose, and lungs.…”

Section: ■ Discussionmentioning

confidence: 54%

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Application of Direct Analysis in Real Time–High Resolution Mass Spectrometry to Investigations of Induced Plant Chemical Defense Mechanisms—Revelation of Negative Feedback Inhibition of an Alliinase

Chambers

Musah

2018

Anal. Chem.

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Several plants of agricultural and medicinal importance utilize defense chemistry that involves deployment of highly labile, reactive, and lachrymatory organosulfur molecules. However, this chemistry is difficult to investigate because the compounds are often short-lived and prone to degradation under the conditions required for analysis by common analytical techniques. This issue has complicated efforts to study the defense chemistry of plants that exploit the use of sulfur in their defense arsenals. This work illustrates how direct analysis in real time-high resolution mass spectrometry (DART-HRMS) can be used to track organosulfur defense compound chemistry under mild conditions. Petiveria alliacea was used as a model plant that exploits the enzyme alliinase to generate induced organosulfur compounds in response to herbivory. Tracking of the organosulfur compounds it produces and quantifying them by DART-HRMS using isotopically labeled analogues revealed a feedback inhibition loop through which the activities of the alliinase are stymied shortly after their activation. The results show that the downstream thiosulfinate products petivericin (100 μM) and pyruvate (8.4 mM) inhibit alliinase activity by 60% and 29%, respectively, after 1 h, and a mixture of the two inhibited alliinase activity by 65%. By 2 h, alliinase activity in the presence of these alliinase-derived products had ceased completely. Because thiosulfinate, pyruvate, and lachrymatory sulfine compounds are produced via the same alliinase-derived sulfenic acid intermediate, the inhibition of alliinase activity by increasing concentrations of downstream products shows how production of these defense compounds is modulated in real time in response to a tissue breach. These findings provide a framework within which heretofore unexplained phenomena observed in the defense chemistry of P. alliacea, onion, garlic, and other plants can be explained, as well as an approach by which to track labile compounds and enzymatic activity by DART-HRMS.

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Section: Discussionsupporting

confidence: 51%

“…Although these compounds are corrosive, the ability of the thiosulfinate to ultimately inhibit the activity of the enzyme that initiates the cascade of reactions that result in their formation (i.e., alliinase) ensures reduced collateral damage. Our observations also may shed light on the heretofore unexplained finding in studies of Alliums and other plants such as onion (Allium cepa), 52−55 garlic (Allium sativum), 56,57 Tulbaghia violacea, 56 Scheme 2. Outline of the Feedback Inhibition Loop Involving P. alliacea Alliinase a a Within seconds of wounding, the exposure of petiveriin to an alliinase/LFS complex results in rapid production of the highly irritating lachrymatory sulfine PMTSO, which causes long-lasting and severe irritation to the eyes, nose, and lungs.…”

Section: ■ Discussionmentioning

confidence: 54%

Application of Direct Analysis in Real Time–High Resolution Mass Spectrometry to Investigations of Induced Plant Chemical Defense Mechanisms—Revelation of Negative Feedback Inhibition of an Alliinase

Chambers

Musah

2018

Anal. Chem.

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“…However, only few publications have reported on the biological activities of T. violacea (Jacobsen et al, 1968;Sparg et al, Ramesar et al, 2008;van den Heever et al, 2008;Kirby & Meyers, 2010;Ebrahim & Pool, 2010). Ramesar et al (2008) reported that crude leaf extracts of T. violacea inhibited angiotensin I converting enzyme (ACE) and also blocked the rise in mean arterial pressure (MAP) associated with infusion of exogenous angiotensin I in normotensive male Wistar rats;…”

Section: Famous African Medicinal Plants Includementioning

confidence: 99%

Effect of Tulbaghia violacea on the blood pressure and heart rate in male spontaneously hypertensive Wistar rats

Raji

Mugabo

Obikeze

2012

Journal of Ethnopharmacology

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Effect of Tulbaghia violacea on the blood pressure and heart rate in male spontaneously hypertensive Wistar rats I. A. RAJITulbaghia violacea Harv. (Alliaceae) is a small bulbous herb which belongs to the family, Alliaceae, most commonly associated with onions and garlic. In South Africa (SA), this herb has been traditionally used in the treatment of various ailments, including fever, colds, asthma, paralysis, hypertension (HTN) and stomach problems. The aim of this study was to evaluate the effect of methanol leaf extracts (MLE) of T. violacea on the blood pressure (BP) and heart rate (HR) in anaesthetized male spontaneously hypertensive rats; and to find out the mechanism(s) by which it acts.The MLE of T. violacea (5 -150 mg/kg), angiotensin I (ang I, 3.1 -100 µg/kg), captopril (10 mg/kg), angiotensin II (ang II, 3.1 -50 µg/kg), losartan (30 mg/kg), phenylephrine T. violacea (60 mg/kg) and captopril (10 mg/kg) were injected intraperitoneally into iii some SHR for 21 days to investigate the chronic effect of these agents on plasma levels of aldosterone. The mean change, the mean of the individual percentage changes and the percentage difference (in mean) observed with each intervention was calculated and statistically analyzed using the Student's t test for significant difference (p < 0.05). The Microsoft Excel software was used for statistical analysis.T. violacea significantly (p < 0.05) reduced the systolic, diastolic, and mean arterial BP;and HR dose-dependently. In a dose-dependent manner, ang I, ang II, phenylephrine significantly (p < 0.05) increased the BP, while propranolol, muscarine and atropine reduced the BP. The increases in BP due to dobutamine were not dose-dependent. In a dose dependent manner, phenylephrine and propranolol reduced the HR, while dobutamine increased the HR. The effect of ang I, ang II, muscarine and atropine on HR were not dose-dependent; with both increases as well as decreases observed with ang I, and II and atropine, while decreases were seen with muscarine. Captopril produced significant (p < 0.05) reduction in BP which were not associated with any change in HR.The co-infusion of ang I with the MLE produced significant (p < 0.05) reduction in BP, which were not associated with significant changes in HR. The co-infusion of ang II with the MLE did not produce any significant changes in BP or HR when compared to the infusion of the standard drug alone. The co-infusion of phenylephrine with the MLE did

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“…violacea is still not on the same level. Only a few scientific reports on the isolated components from T. violacea are available in the literature, including work by Jacobsen et al (1968), Bate-Smith (1968), Gmelin et al (1976), Burton (1990), Burton and Kaye (1992), Watson and Dallwitz (2000), van Staden (2002a, b, 2006), Kubec et al (2002) and Maoela (2005). Most recently, three closely related anticancer fractions were isolated from T. violacea aqueous extracts, only Tv-7 has its chemical structure been solved as methyl--D-glucopyranoside (Lyantagaye, 2011).…”

Section: Introductionmentioning

confidence: 99%

Two new pro-apoptotic glucopyranosides from Tulbaghia violacea

Lyantagaye¹

2013

J. Med. Plants Res.

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Tulbaghia violacea is a widely known anticancer herb used as traditional medicine in the Southern African region. However, the identities of the chemical compounds responsible for the medicinal properties are still at large. Isolation of the pro-apoptotic compounds from T. violacea was carried out using apoptosis induction-guided fractionation. The chemical structures of the pro-apoptotic molecules were elucidated on the basis of extensive spectroscopic analysis, including 1D and 2D nuclear magnetic resonance (NMR), infrared (IR) and elemental analysis. Pro-apoptotic glucopyranosides Dfructofuranose-(26)-methyl--D-glucoyranoside and -D-fructofuranosyl-(26)--D-glucopyranoside were uncovered from aqueous whole plant extracts of T. violacea using bioactivity-guided purification. Glucopyranosides D-fructofuranose-(26)-methyl--D-glucoyranoside and -D-fructofuranosyl-(26)--D-glucopyranoside have structural similarity with the earlier reported methyl -D-glucopyranoside from the same herb, which selectively kills cancer cells through apoptosis mechanisms. The discovery of these molecules could contribute towards the development of new anticancer drugs.

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An alkyl-cysteine sulfoxide lyase in Tulbaghia violacea and its relation to other alliinase-like enzymes

Cited by 22 publications

References 25 publications

Application of Direct Analysis in Real Time–High Resolution Mass Spectrometry to Investigations of Induced Plant Chemical Defense Mechanisms—Revelation of Negative Feedback Inhibition of an Alliinase

Application of Direct Analysis in Real Time–High Resolution Mass Spectrometry to Investigations of Induced Plant Chemical Defense Mechanisms—Revelation of Negative Feedback Inhibition of an Alliinase

Effect of Tulbaghia violacea on the blood pressure and heart rate in male spontaneously hypertensive Wistar rats

Two new pro-apoptotic glucopyranosides from Tulbaghia violacea

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