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Article: Appraising California Zinfandel Exposure to Wildfire Smoke Using Natural Product Phenolic Diglycoside Biomarkers

Crews, Phillip / Dorenbach, Paul / Amberchan, Gabriella

Journal of agricultural and food chemistry. 2022 Sept. 08, v. 70, no. 37

2022

Abstract: Zinfandel grapes are ubiquitous in California and its wine quality could be negatively impacted from wildfire smoke. Thus, the occurrence of fires prior to grape harvest presents a persistent problem to both viticulture and enology processes. This is the ...

Abstract	Zinfandel grapes are ubiquitous in California and its wine quality could be negatively impacted from wildfire smoke. Thus, the occurrence of fires prior to grape harvest presents a persistent problem to both viticulture and enology processes. This is the first broad study on Zinfandel to investigate wine quality defects produced by natural wildfires. The project, guided by UHPLC separations and MS² multiple reaction monitoring, involved measuring natural product phenolic diglycosides (PDs) bioaccumulated in grapes, and expands outcomes published in 2022 by our team (called the Santa Cruz Campaign, SCC). The plan was implemented by exploiting a panel of six marker PDs 1–6 and their deuterated analogues. Examined in the study were 24 different Zinfandel wines obtained from 2016 to 2021 vintages of nine different American Viticulture Areas (AVAs) that were also within five of the eight California Zinfandel viticulture zones. The goal was to extend understanding on PD variations using patterns that possibly change as a function of appellation and fire intensity. Preliminary data was obtained to examine the relative amounts of PDs localized in berry skin versus pulp. The baseline of <15 ppb was proposed by surveying 18 distinct unsmoked Zinfandel wines. It was proposed to estimate the smoke impact on other Zinfandel wines by using seven PD ppb concentrations categories. A pilot study was also launched to assess conclusions by comparing ppb-based ratings versus sensory evaluation quality estimates. General findings presented herein should provide an important foundation to build understanding of using PD patterns to forecast possible Zinfandel wine wildfire damage.
Keywords	biomarkers ; fire intensity ; food chemistry ; glycosides ; grapes ; pulp ; sensory evaluation ; smoke ; viticulture ; wildfires ; wine quality ; winemaking ; California
Language	English
Dates of publication	2022-0908
Size	p. 11738-11748.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	241619-0
ISSN	1520-5118 ; 0021-8561
ISSN (online)	1520-5118
ISSN	0021-8561
DOI	10.1021/acs.jafc.2c04807
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Appraising California Zinfandel Exposure to Wildfire Smoke Using Natural Product Phenolic Diglycoside Biomarkers.

Crews, Phillip / Dorenbach, Paul / Amberchan, Gabriella

Journal of agricultural and food chemistry

2022 Volume 70, Issue 37, Page(s) 11738–11748

Abstract	Zinfandel grapes are ubiquitous in California and its wine quality could be negatively impacted from wildfire smoke. Thus, the occurrence of fires prior to grape harvest presents a persistent problem to both viticulture and enology processes. This is the first broad study on Zinfandel to investigate wine quality defects produced by natural wildfires. The project, guided by UHPLC separations and MS
MeSH term(s)	Biological Products ; Biomarkers ; California ; Fruit/chemistry ; Phenols/analysis ; Pilot Projects ; Smoke ; Vitis ; Wildfires ; Wine/analysis
Chemical Substances	Biological Products ; Biomarkers ; Phenols ; Smoke
Language	English
Publishing date	2022-09-08
Publishing country	United States
Document type	Journal Article
ZDB-ID	241619-0
ISSN	1520-5118 ; 0021-8561
ISSN (online)	1520-5118
ISSN	0021-8561
DOI	10.1021/acs.jafc.2c04807
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Article ; Online: Unraveling Structures Containing Highly Conjugated Pyrrolo[4,3,2-

McCauley, Erin P / Smith, Gavin C / Crews, Phillip

Journal of natural products

2020 Volume 83, Issue 1, Page(s) 174–178

Abstract: This study began with the goal of identifying additional constituents ... ...

Abstract	This study began with the goal of identifying additional constituents from
MeSH term(s)	Animals ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Porifera/chemistry ; Protons ; Quinolines/chemistry
Chemical Substances	Protons ; Quinolines
Language	English
Publishing date	2020-01-06
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.9b01111
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Article ; Online: In Vivo Evaluation of (-)-Zampanolide Demonstrates Potent and Persistent Antitumor Efficacy When Targeted to the Tumor Site.

Takahashi-Ruiz, Leila / Morris, Joseph D / Crews, Phillip / Johnson, Tyler A / Risinger, April L

Molecules (Basel, Switzerland)

2022 Volume 27, Issue 13

Abstract: Microtubule-stabilizing agents (MSAs) are a class of compounds used in the treatment of triple-negative breast cancer (TNBC), a subtype of breast cancer where chemotherapy remains the standard-of-care for patients. Taxanes like paclitaxel and docetaxel ... ...

Abstract	Microtubule-stabilizing agents (MSAs) are a class of compounds used in the treatment of triple-negative breast cancer (TNBC), a subtype of breast cancer where chemotherapy remains the standard-of-care for patients. Taxanes like paclitaxel and docetaxel have demonstrated efficacy against TNBC in the clinic, however new classes of MSAs need to be identified due to the rise of taxane resistance in patients. (-)-Zampanolide is a covalent microtubule stabilizer that can circumvent taxane resistance in vitro but has not been evaluated for in vivo antitumor efficacy. Here, we determine that (-)-zampanolide has similar potency and efficacy to paclitaxel in TNBC cell lines, but is significantly more persistent due to its covalent binding. We also provide the first reported in vivo antitumor evaluation of (-)-zampanolide where we determine that it has potent and persistent antitumor efficacy when delivered intratumorally. Future work on zampanolide to further evaluate its pharmacophore and determine ways to improve its systemic therapeutic window would make this compound a potential candidate for clinical development through its ability to circumvent taxane-resistance mechanisms.
MeSH term(s)	Antineoplastic Agents/chemistry ; Cell Line, Tumor ; Humans ; Macrolides/chemistry ; Microtubules/metabolism ; Paclitaxel/chemistry ; Triple Negative Breast Neoplasms/drug therapy ; Triple Negative Breast Neoplasms/metabolism
Chemical Substances	Antineoplastic Agents ; Macrolides ; zampanolide ; Paclitaxel (P88XT4IS4D)
Language	English
Publishing date	2022-07-01
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules27134244
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Article ; Online: Enzymatic Benzofuranoindoline Formation in the Biosynthesis of the Strained Bridgehead Bicyclic Dipeptide (+)-Azonazine A.

Liu, Mengting / Ohashi, Masao / Zhou, Qingyang / Sanders, Jacob N / McCauley, Erin P / Crews, Phillip / Houk, K N / Tang, Yi

Angewandte Chemie (International ed. in English)

2023 Volume 62, Issue 40, Page(s) e202311266

Abstract: We uncovered and reconstituted a concise biosynthetic pathway of the strained dipeptide (+)-azonazine A from marine-derived Aspergillus insulicola. Formation of the hexacyclic benzofuranoindoline ring system from cyclo-(l-Trp-N-methyl-l-Tyr) is catalyzed ...

Abstract	We uncovered and reconstituted a concise biosynthetic pathway of the strained dipeptide (+)-azonazine A from marine-derived Aspergillus insulicola. Formation of the hexacyclic benzofuranoindoline ring system from cyclo-(l-Trp-N-methyl-l-Tyr) is catalyzed by a P450 enzyme through an oxidative cyclization. Supplementing the producing strain with various indole-substituted tryptophan derivatives resulted in the generation of a series of azonazine A analogs.
MeSH term(s)	Dipeptides/metabolism ; Oxidation-Reduction ; Cyclization ; Cytochrome P-450 Enzyme System/metabolism
Chemical Substances	azonazine ; Dipeptides ; Cytochrome P-450 Enzyme System (9035-51-2)
Language	English
Publishing date	2023-08-28
Publishing country	Germany
Document type	Journal Article ; Research Support, U.S. Gov't, Non-P.H.S. ; Research Support, N.I.H., Extramural
ZDB-ID	2011836-3
ISSN	1521-3773 ; 1433-7851
ISSN (online)	1521-3773
ISSN	1433-7851
DOI	10.1002/anie.202311266
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Article ; Online: Suppression of MAPK/NF‐kB and activation of Nrf2 signaling by Ajugarin‐I in EAE model of multiple sclerosis

Khan, Adnan / Shal, Bushra / Khan, Ashraf Ullah / Bibi, Tehmina / Zeeshan, Sara / Zahra, Syeda Saniya / Crews, Phillip / Haq, Ihsan ul / Din, Fakhar ud / Ali, Hussain / Khan, Salman

Phytotherapy Research. 2023 June, v. 37, no. 6 p.2326-2343

2023

Abstract: Multiple sclerosis (MS) is a debilitating neurodegenerative autoimmune disease of the central nervous system (CNS). The current study aimed to investigate the neuroprotective properties of Ajugarin‐I (Aju‐I) against the experimental autoimmune ... ...

Abstract	Multiple sclerosis (MS) is a debilitating neurodegenerative autoimmune disease of the central nervous system (CNS). The current study aimed to investigate the neuroprotective properties of Ajugarin‐I (Aju‐I) against the experimental autoimmune encephalomyelitis (EAE) model of MS and explored the underlying mechanism involved. The protective potential of Aju‐I was first confirmed against glutamate‐induced HT22 cells and hydrogen peroxide (H₂O₂)‐induced BV2 cells. Next, an EAE model has been established to investigate the mechanisms of MS and identify potential candidates for MS treatment. The behavioral results demonstrated that Aju‐I post‐immunization treatment markedly reduced the EAE‐associated clinical score, motor impairment, and neuropathic pain. Evans blue and fluorescein isothiocyanate extravasation in the brain were markedly reduced by Aju‐I. It effectively restored the EAE‐associated histopathological changes in the brain and spinal cord. It markedly attenuated EAE‐induced inflammation in the CNS by reducing the expression levels of p‐38/JNK/NF‐κB but increased the expression of IkB‐α. It suppressed oxidative stress by increasing the expression of Nrf2 but decreasing the expression of keap‐1. It suppressed EAE‐induced apoptosis in the CNS by regulating Bax/Bcl‐2 and Caspase‐3 expression. Taken together, this study suggests that Aju‐I treatment exhibits neuroprotective properties in the EAE model of MS via regulation of MAPK/NF‐κB, Nrf2/Keap‐1, and Bcl2/Bax signaling.
Keywords	apoptosis ; autoimmune diseases ; brain ; caspase-3 ; encephalitis ; fluorescein ; histopathology ; hydrogen peroxide ; inflammation ; isothiocyanates ; models ; oxidative stress ; pain ; phytotherapy ; research ; sclerosis ; spinal cord
Language	English
Dates of publication	2023-06
Size	p. 2326-2343.
Publishing place	John Wiley & Sons, Ltd.
Document type	Article ; Online
Note	JOURNAL ARTICLE
ZDB-ID	639136-9
ISSN	1099-1573 ; 0951-418X
ISSN (online)	1099-1573
ISSN	0951-418X
DOI	10.1002/ptr.7751
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Article: Unraveling Structures Containing Highly Conjugated Pyrrolo[4,3,2-de]quinoline Cores That Are Deficient in Diagnostic Proton NMR Signals

McCauley, Erin P / Smith, Gavin C / Crews, Phillip

Journal of natural products. 2020 Jan. 06, v. 83, no. 1

2020

Abstract: This study began with the goal of identifying additional constituents from Zyzzya fuliginosa extracts obtained from an Indo-Pacific sponge (coll. no. 06132). The previous work identified several red and green pyrroloiminiquinones (aka pyrrolo[4,3,2-de] ... ...

Abstract	This study began with the goal of identifying additional constituents from Zyzzya fuliginosa extracts obtained from an Indo-Pacific sponge (coll. no. 06132). The previous work identified several red and green pyrroloiminiquinones (aka pyrrolo[4,3,2-de]quinolines), and this reinvestigation provided two additional analogues, a blue compound named zyzzamine A (1) and a green compound named zyzzamine B (2). The relatively low ratio of H/[sum(CNO)] = 0.71 or 0.76 of this pair greatly complicated the final steps of compound characterization and required the use of five 2D NMR strategies and MS2 data sets.
Keywords	data collection ; nuclear magnetic resonance spectroscopy ; quinoline ; quinones
Language	English
Dates of publication	2020-0106
Size	p. 174-178.
Publishing place	American Chemical Society and American Society of Pharmacognosy
Document type	Article
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.9b01111
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Article ; Online: Reevaluation of a Bicyclic Pyrazoline as a Selective 15-Lipoxygenase V-Type Activator Possessing Fatty Acid Specificity.

van Hoorebeke, Christopher / Yang, Kevin / Mussetter, Samuel J / Koch, Grant / Rutz, Natalie / Lokey, R Scott / Crews, Phillip / Holman, Theodore R

ACS omega

2022 Volume 7, Issue 47, Page(s) 43169–43179

Abstract: Regulation of lipoxygenase (LOX) activity is of great interest due to the involvement of the various LOX isoforms in the inflammatory process and hence many diseases. The bulk of investigations have centered around the discovery and design of inhibitors. ...

Abstract	Regulation of lipoxygenase (LOX) activity is of great interest due to the involvement of the various LOX isoforms in the inflammatory process and hence many diseases. The bulk of investigations have centered around the discovery and design of inhibitors. However, the emerging understanding of the role of h15-LOX-1 in the resolution of inflammation provides a rationale for the development of activators as well. Bicyclic pyrazolines are known bioactive molecules that have been shown to display antibiotic and anti-inflammatory activities. In the current work, we reevaluated a previously discovered bicyclic pyrazoline h15-LOX-1 activator, PKUMDL_MH_1001 (written as
Language	English
Publishing date	2022-11-17
Publishing country	United States
Document type	Journal Article
ISSN	2470-1343
ISSN (online)	2470-1343
DOI	10.1021/acsomega.2c05877
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Article ; Online: Tandem high resolution mass spectrometry based phytochemical composition of Sauromatum guttatum tubers and its enzyme inhibitory potential with molecular docking.

Bashir, Kashif / Naz, Sadia / Rasheed, Hafiz Majid / Farooq, Umar / Shah, Abdul Jabbar / McCauley, Erin P / Crews, Phillip / Khan, Taous

Journal of chromatography. A

2022 Volume 1672, Page(s) 463055

Abstract: Sauromatum guttatum has been traditionally used in the treatment of snakebite and tumors in India, Pakistan, and China. However, it lacks detailed phytochemical composition like other members of the family Araceae. Therefore, the aim of the present study ...

Abstract	Sauromatum guttatum has been traditionally used in the treatment of snakebite and tumors in India, Pakistan, and China. However, it lacks detailed phytochemical composition like other members of the family Araceae. Therefore, the aim of the present study was to investigate the phytochemical composition of crude methanolic extract and subsequent fractions from S. guttatum tubers and to determine their enzyme inhibitory potentials. The phytochemical profile was studied through tandem high-resolution mass-based phytochemical analysis and Global Natural Product Social (GNPS) molecular networking. Similarly, crude extract and fractions were also investigated for enzyme inhibitory activity against urease and α-glucosidase. Twenty-six compounds were dereplicated belonging to flavone C-glycosides, flavone O-glycosides, phenolic acids, phenolic acid glycosides, and iridoid glycosides. The n-butanol fraction was particularly found rich in flavone di-C-glycosides including schaftoside, isoschaftoside, neoschaftoside, and vicenin-2. The n-butanol fraction exhibited the highest in vitro inhibition against urease and α-glucosidase with IC
MeSH term(s)	1-Butanol ; Araceae ; Flavones/chemistry ; Glycosides/chemistry ; Molecular Docking Simulation ; Phytochemicals/pharmacology ; Plant Extracts/chemistry ; Plant Extracts/pharmacology ; Tandem Mass Spectrometry ; Urease ; alpha-Glucosidases
Chemical Substances	Flavones ; Glycosides ; Phytochemicals ; Plant Extracts ; 1-Butanol (8PJ61P6TS3) ; alpha-Glucosidases (EC 3.2.1.20) ; Urease (EC 3.5.1.5)
Language	English
Publishing date	2022-04-12
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1171488-8
ISSN	1873-3778 ; 0021-9673
ISSN (online)	1873-3778
ISSN	0021-9673
DOI	10.1016/j.chroma.2022.463055
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Article: Natural Product Phenolic Diglycosides Created from Wildfires, Defining Their Impact on California and Oregon Grapes and Wines

Crews, Phillip / Dorenbach, Paul / Amberchan, Gabriella / Keiffer, Ryan F. / Lizama-Chamu, Itzel / Ruthenburg, Travis C. / McCauley, Erin P. / McGourty, Glenn

Journal of natural products. 2022 Mar. 03, v. 85, no. 3

2022

Abstract: Forest fires produce malodorous phenols, bioaccumulated in grapes as odorless phenol glycosides (mono- to tri-), and produce unpleasant smoke tainted wines when these complexes are transformed by glycosidases in saliva. Metabolomic analyses were used to ... ...

Abstract	Forest fires produce malodorous phenols, bioaccumulated in grapes as odorless phenol glycosides (mono- to tri-), and produce unpleasant smoke tainted wines when these complexes are transformed by glycosidases in saliva. Metabolomic analyses were used to further understand smoke taint by quantitating marker phenolic diglycosides via UHPLC separations and MS/MS multiple reaction monitoring. A collection of grapes and wines provided data to forecast wine quality of grapes subjected to wildfire smoke infestations; the analytics used a panel of reference compounds (1–6). Overall, eight different Vitis vinifera varietals were examined from 2017–2021 vintages involving >218 distinct samples (wines and/or grapes) from 21 different American Viticulture Areas. Results acquired allowed correlation of phenolic diglycoside levels as a function of grape cultivar, varietal clones, and intensity of wildfire smoke. Baseline data were tabulated for nonsmoked samples (especially, Cabernet Sauvignon having a sum 1–6 of <6 μg/L) and then compared to those exposed to six other levels of smoke. Outcomes established that (1) analyzing paired samples (bottled wines versus smoke-exposed grapes) can provide diagnostic metabolomic data, (2) phenolic diglycosides are stable in wines aged for >2.5 years, and (3) major gaps exist in our current understanding of this pool of metabolites.
Keywords	Oregon ; Vitis vinifera ; cultivars ; forests ; glycosidases ; glycosides ; grapes ; metabolites ; metabolomics ; phenol ; saliva ; smoke ; taint ; viticulture ; wine quality ; California
Language	English
Dates of publication	2022-0303
Size	p. 547-561.
Publishing place	American Chemical Society and American Society of Pharmacognosy
Document type	Article
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.2c00028
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