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1. Compartmentalization at the interface of primary and alkaloid metabolism

Author:
Jacinta L. Watkins; Peter J. Facchini
Source:
Current opinion in plant biology 2022 v.66 pp. 102186
ISSN:
1369-5266
Subject:
monoterpenoids,   etc   ; alkaloids; biosynthesis; indoles; organelles; plant biology; synthetic biology;     Show all 7 Subjects
Abstract:
... Plants produce many compounds used by humans as medicines, including alkaloids of the benzylisoquinoline (BIA), monoterpene indole (MIA) and tropane classes. The biosynthetic pathways of these pharmaceutical alkaloids are complex and spatially segregated across several tissues, cell-types and organelles. This review discusses the origin of primary metabolic inputs required by these specialized bio ...
DOI:
10.1016/j.pbi.2022.102186

2. Exploration by molecular networking of Strychnos alkaloids reveals the unexpected occurrence of strychnine in seven Strychnos species

Author:
Olivier Bonnet; Mehdi A. Beniddir; Pierre Champy; Védaste Kagisha; Alain Nyirimigabo; Carla Hamann; Giorgi Jgerenaia; Allison Ledoux; Alembert Tiabou Tchinda; Luc Angenot; Michel Frédérich
Source:
Toxicon 2022 v.215 pp. 57-68
ISSN:
0041-0101
Subject:
monoterpenoids,   etc   ; asphyxia; chemotaxonomy; computer software; death; malaria; metabolites; probability; solvents; strychnine;     Show all 10 Subjects
Abstract:
... Plants of the Strychnos genus, which include about 200 species, are used for multiple traditional purposes as hunting poison, for example, and have shown interesting pharmacological properties, especially curarizing and tetanizing, but also against malaria. Many monoterpene indole alkaloids have already been isolated and identified. Among them, there is strychnine, a famous alkaloid that can cause ...
DOI:
10.1016/j.toxicon.2022.06.002

3. Chemical constituents from Dracocephalum moldavica L. and their chemotaxonomic significance

Author:
Jiaming Wang; Jinfeng Sun; Mengjie Wang; Huiqiong Cui; Wei Zhou; Gao Li
Source:
Biochemical systematics and ecology 2022 v.102 pp. 104422
ISSN:
0305-1978
Subject:
monoterpenoids,   etc   ; Dracocephalum moldavica; chemotaxonomy; ecology; glycosides; lignans; norisoprenoids; phytochemicals; spectral analysis; triterpenoids;     Show all 10 Subjects
Abstract:
... A phytochemical investigation of the aerial parts of Dracocephalum moldavica L. (Lamiaceae) led to the isolation and characterization of 30 compounds, including eight lignans (1–8), seven phenols (9–15), five triterpenoids (16–20), four monoterpenoids (21–24), four glycosides (25–28) and two megastigmanes (29 and 30). The structures of these compounds were determined by spectroscopic data analysis ...
DOI:
10.1016/j.bse.2022.104422

4. Regiospecific 7-hydroxylation of ten-carbon monoterpenes by detoxifying CYP5035S7 monooxygenase of the white-rot fungus Polyporus arcularius

Author:
Nico D. Fessner; Hansjörg Weber; Anton Glieder
Source:
Biochemical and biophysical research communications 2022 v.595 pp. 35-40
ISSN:
0006-291X
Subject:
monoterpenoids,   etc   ; Polyporus arcularius; biotransformation; enzymes; p-cymene; regioselectivity; research; white-rot fungi;     Show all 8 Subjects
Abstract:
... In a previous study, we identified CYP5035S7 of the white-rot fungus Polyporus arcularius with a broad activity towards monoterpenes such as p-cymene. Therefore, in this study we aimed at further exploring the substrate scope of detoxifying CYP5035S7 towards terpenes and semi-preparatively isolating some of the products via whole-cell biotransformation, in order to obtain information about the enz ...
DOI:
10.1016/j.bbrc.2022.01.072

5. Bioactive constituents from the leaves of Metapanax delavayi with anti-benign prostatic hyperplasia activities

Author:
Bangjian Dong; Chongzhi Sun; Mengyue Wang; Feng Liu; Xiaobo Li
Source:
Phytochemistry 2022 v.193 pp. 112979
ISSN:
0031-9422
Subject:
monoterpenoids,   etc   ; Araliaceae; biological assessment; circular dichroism spectroscopy; glycosides; hydrolysis; hyperplasia; plant biochemistry; sesquiterpenoids;     Show all 9 Subjects
Abstract:
... In the course of our continuing search for biologically active compounds from medicinal sources, we further investigated the aqueous extract of Metapanax delavayi (Franch.) J. Wen & Frodin (Araliaceae) leaves. Five undescribed terpene glycosides, liangwanosides B–F referring to two megastigmane glycosides, one monoterpene glycoside, and two sesquiterpene glycosides, together with seven known compo ...
DOI:
10.1016/j.phytochem.2021.112979

6. Bioactive terpenoids derived from plant endophytic fungi: An updated review (2011–2020)

Author:
Bahman Zamani Amirzakariya; Abolfazl Shakeri
Source:
Phytochemistry 2022 v.197 pp. 113130
ISSN:
0031-9422
Subject:
monoterpenoids,   etc   ; antioxidants; coumarins; cytotoxicity; diterpenoids; endophytes; meroterpenoids; plant biochemistry; polyketides; quinones; sesquiterpenoids; triterpenoids;     Show all 12 Subjects
Abstract:
... Plant endophytes have been considered as novel sources of naturally occurring compounds with various biological activities, including cytotoxic, antimicrobial, anti-inflammatory, anticancer, herbicides, antileishmanial and antioxidant. A variety of specialised products, comprising terpenoids, alkaloids, polyketides, phenolic compounds, coumarins, and quinone derivatives have been reported from var ...
DOI:
10.1016/j.phytochem.2022.113130

7. Evaluation of germination effect on volatile compounds of different faba bean cultivars using HS-SPME/GC-MS

Author:
Imene Rajhi; Bechir Baccouri; Fatma Rajhi; Jamila Hammami; Monia Souibgui; Moez Amri; Haythem Mhadhbi; Guido Flamini
Source:
Journal of food composition and analysis 2022 pp. 104692
ISSN:
0889-1575
Subject:
monoterpenoids,   etc   ; Vicia faba; cultivars; faba beans; flavor; food composition; furans; germination; odors; sesquiterpenoids;     Show all 10 Subjects
Abstract:
... The effect of germination on flavor attributes of six Vicia faba L. cultivars (Najeh, Saber, Chourouk, Local, Bachar and Badii) was assessed using HS-SPME/GC-MS technique. Of all aroma compounds identified, 37 were emitted by unsprouted (19) and sprouted (28) seeds. However, 32 active odors were characterized in the flours obtained from unsprouted (18) and sprouted (28) grains. The total identific ...
DOI:
10.1016/j.jfca.2022.104692

8. Male Accessory Glands of Blister Beetles and Cantharidin Release: A Comparative Ultrastructural Analysis

Author:
Maurizio Muzzi; Emiliano Mancini; Emiliano Fratini; Manuela Cervelli; Tecla Gasperi; Paolo Mariottini; Tiziana Persichini; Marco Alberto Bologna; Andrea Di Giulio
Source:
Insects 2022 v.13 no.2 pp. -
ISSN:
2075-4450
Subject:
monoterpenoids,   etc   ; Meloidae; cantharidin; hemolymph; males; microscopy; mitochondria; muscles; rough endoplasmic reticulum; spermatophores; toxicity;     Show all 11 Subjects
Abstract:
... Members of the family Meloidae are known to produce cantharidin, a highly toxic monoterpene found in their hemolymph and exuded as droplets capable of deterring many predators. As a nuptial gift, males transfer large amounts of cantharidin to females via a spermatophore, which is formed by specific accessory glands containing high concentrations of this terpene. Using light, electron and ion beam ...
DOI:
10.3390/insects13020132

9. Differential regulation of fluorescent alkaloid metabolism between idioblast and lacticifer cells during leaf development in Catharanthus roseus seedlings

Author:
Mai Uzaki; Kotaro Yamamoto; Akio Murakami; Yushiro Fuji; Miwa Ohnishi; Kimitsune Ishizaki; Hidehiro Fukaki; Masami Yokota Hirai; Tetsuro Mimura
Source:
Journal of plant research 2022 v.135 no.3 pp. 473-483
ISSN:
0918-9440
Subject:
monoterpenoids,   etc   ; Catharanthus roseus; biosynthesis; fluorescence; leaf development; medicinal plants; metabolites; research; seedling growth; serpentine;     Show all 10 Subjects
Abstract:
... Bioactive specialized (secondary) metabolites are indispensable for plant development or adjustment to their surrounding environment. In many plants, these specialized metabolites are accumulated in specifically differentiated cells. Catharanthus roseus is a well-known medicinal plant known for producing many kinds of monoterpenoid indole alkaloids (MIAs). C. roseus has two types of specifically d ...
DOI:
10.1007/s10265-022-01380-1

10. Synthesis of a pyrrolidine derivative of a carvotacetone and monoterpenes for anti-methicillin-resistant Staphylococcus aureus and anti-cryptococcal properties

Author:
Veronica M. Masila; Albert J. Ndakala; Jacob O. Midiwo; Robert Byamukama; Rahab W. Kamau; Mallika Kumarihamy; Ilias Muhammad
Source:
Natural product research 2022 v.36 no.9 pp. 2321-2328
ISSN:
1478-6427
Subject:
monoterpenoids,   etc   ; Cryptococcus neoformans; acetates; carvacrol; methicillin-resistant Staphylococcus aureus; pharmaceutical industry; research; spectral analysis;     Show all 8 Subjects
Abstract:
... Monoterpene derivatives are of great biological relevance in the pharmaceutical industry. In the present study, pyrrolidine derivative of a carvotacetone, 3-O-benzylcarvotacetone (1), and selected monoterpenes (3-hydroxy-2-isopropyl-5-methyl-p-benzoquinone (3) and cis-piperitol (5)) were prepared to provide (R)-1-(4-(benzyloxy)-5-isopropyl-2-methylcyclohexa-1,3-dien-1-yl)-pyrrolidine (2), 2-isopro ...
DOI:
10.1080/14786419.2020.1833201

11. Iboga-type alkaloids with Indolizidino[8,7-b]Indole scaffold and bisindole alkaloids from Tabernaemontana bufalina Lour

Author:
Shun-Qing Chen; Jia Jia; Jing-Yao Hu; Jun Wu; Wen-Ting Sun; Mingxin Zheng; Xi Wang; Kong-Kai Zhu; Cheng-Shi Jiang; Sheng-Ping Yang; Juan Zhang; Shou-Bao Wang; You-Sheng Cai
Source:
Phytochemistry 2022 v.196 pp. 113089
ISSN:
0031-9422
Subject:
monoterpenoids,   etc   ; Bacillus subtilis; Helicobacter pylori; Mycobacterium smegmatis; Tabernaemontana; antimicrobial properties; cholinesterase; phytochemicals; quantum mechanics; spectroscopy;     Show all 10 Subjects
Abstract:
... Phytochemical investigation on the aerial parts of Tabernaemontana bufalina Lour. (Apocynaceae) led to the identification of four undescribed monoterpenoid indole alkaloids named taberbufamines A−D, an undescribed natural product, and fourteen known indole alkaloids. The structures of the undescribed alkaloids were established by spectroscopic and computational methods, and their absolute configur ...
DOI:
10.1016/j.phytochem.2022.113089

12. Identification of Bacillus strains producing glycosidases active on rutin and grape glycosidic aroma precursors

Author:
Maxime Haure; Thi Kim Chi Nguyen; Aurélie Cendrès; Sandrine Perino; Yves Waché; Hélène Licandro
Source:
Lebensmittel-Wissenschaft + Technologie 2022 v.154 pp. 112637
ISSN:
0023-6438
Subject:
monoterpenoids,   etc   ; Bacillus amyloliquefaciens; Bacillus licheniformis; glycosidases; glycosides; grape pomace; grapes; odors; phenylethyl alcohol; rutin; yeasts;     Show all 11 Subjects
Abstract:
... Most of the glycosidic aroma precursors in grape consist of diglycosides such as rutinoside. Yeast glycosidases have been extensively studied but their activity is limited to monoglucosidic precursors. Yet, there is no study about application of glycosidases active on rutinoside in grape. In this study, we screened Bacillus isolates for their glycosidase activities on rutin and grape aroma precurs ...
DOI:
10.1016/j.lwt.2021.112637

13. A New Monoterpenoid Glycoside from Syzygium fluviatile

Author:
Ding-Li Zhang; Yi-Kao Hu; Ji-Hua Wang; Yan Zhao; Yu-Ping Huang; Gui-Jun Zeng; Yong Zhao
Source:
Chemistry of natural compounds 2021 v.57 no.1 pp. 69-71
ISSN:
0009-3130
Subject:
monoterpenoids,   etc   ; Syzygium; chemistry; glycosides;     Show all 4 Subjects
Abstract:
... A new monoterpenoid glycoside, together with seven known aliphatic acid derivatives, was isolated from the twigs and leaves of Syzygium fluviatile. Their structures were elucidated by means of NMR and HR-ESI-MS data and comparison with the reported values. This is the first example of a monoterpenoid glycoside from Syzygium plants. ...
DOI:
10.1007/s10600-021-03285-2

14. Bioinspired Early Divergent Oxidative Cyclizations toward Pleiocarpamine, Talbotine, and Strictamine

Author:
Maxime Jarret; Hussein Abou-Hamdan; Cyrille Kouklovsky; Erwan Poupon; Laurent Evanno; Guillaume Vincent
Source:
Organic letters 2021 v.23 no.4 pp. 1355-1360
ISSN:
1523-7052
Subject:
monoterpenoids,   etc   ; biosynthesis; models; Germany;     Show all 4 Subjects
Abstract:
... Toward the mavacurane and akuammilane monoterpene indole alkaloids, we developed divergent oxidative couplings between the indole nucleus (at N1 or C7) and the C16-malonate of a common tricyclic model related to strictosidine according to a biosynthetic hypothesis postulated by Hesse and Schmid. These oxidative cyclizations led selectively to the formation of the N1–C16 bond of pleiocarpamine or t ...
DOI:
10.1021/acs.orglett.1c00018

15. Floral Aromatics of Ptelea: Chemical Identification and Human Response

Author:
Anna J. Talcott Stewart; Terri Boylston; Lester Wilson; William R. Graves
Source:
Journal of the American Society for Horticultural Science 2022 v.147 no.1 pp. 25-34
ISSN:
2327-9788
Subject:
monoterpenoids,   etc   ; Citrus; Ptelea trifoliata; butyrates; gas chromatography; horticulture; humans; mass spectrometry; methyl chavicol; odors; sesquiterpenoids; surveys;     Show all 12 Subjects
Abstract:
... Many members of the citrus family (Rutaceae) are valued for the aromatic compounds emitted by their flowers. Ptelea species are unusually cold-hardy members of the Rutaceae, but conflicting descriptions of the fragrance of their unisexual flowers may discourage the use of these trees. We analyzed floral volatiles and human response to these chemicals to test the hypothesis that the fragrance of st ...
DOI:
10.21273/JASHS05119-21

16. Life-history strategies and virulence in the pinewood nematode

Author:
Carla S. Pimentel; Matthew P. Ayres
Source:
Physiological and molecular plant pathology 2022 v.117 pp. 101756
ISSN:
0885-5765
Subject:
monoterpenoids,   etc   ; Bursaphelenchus xylophilus; forest pathogens; forests; fungi; life history; plant pathology; population growth; virulence; North America;     Show all 10 Subjects
Abstract:
... We assessed variation and covariation in life history traits of the forest pathogen Bursaphelenchus xylophilus from a native population in North America. We tested for relationships between life history traits and virulence. There was more than two-fold variation among isolates from the same forest in their population growth rates when feeding on commonly co-occurring fungus. Slow-growing isolates ...
DOI:
10.1016/j.pmpp.2021.101756

17. Minor terpenoids from the stems and twigs of Rhododendron ovatum

Author:
Min Ma; Ya-Nan Wang; Hai-Qiang Wang; Shuang-Gang Ma; Yong Li; Jing Qu; Shi-Shan Yu
Source:
Journal of Asian natural products research 2022 v.24 no.5 pp. 445-456
ISSN:
1477-2213
Subject:
monoterpenoids,   etc   ; Rhododendron; circular dichroism spectroscopy; colorectal neoplasms; cytotoxicity; humans; neoplasm cells; neuroglia; nitric oxide; research; triterpenoids;     Show all 11 Subjects
Abstract:
... Four minor undescribed terpenoids, including a monoterpenoid (1) and three triterpenoids (3, 6 and 7), together with 26 known terpenoids were isolated from the stems and twigs of Rhododendron Ovatum. Their structures were identified by extensive spectroscopic analyses and electronic circular dichroism (ECD) techniques. Compound 10 showed excellent cytotoxicity against human colon cancer cell (HCT- ...
DOI:
10.1080/10286020.2022.2027916

18. Who Cares More about Chemical Defenses — the Macroalgal Producer or Its Main Grazer?

Author:
Sabrina Heiser; Charles D. Amsler; Cecilia J. Brothers; Margaret O. Amsler; Andrew J. Shilling; Lauren Bozarth; Carmen B. Davis; James B. McClintock; Bill J. Baker
Source:
Journal of chemical ecology 2022 v.48 no.4 pp. 416-430
ISSN:
0098-0331
Subject:
monoterpenoids,   etc   ; Amphipoda; Plocamium; chemical ecology; community structure; diet; macroalgae; predation; reproductive performance; secondary metabolites; Antarctic region;     Show all 11 Subjects
Abstract:
... The consequences of defensive secondary metabolite concentrations and interspecific metabolite diversity on grazers have been extensively investigated. Grazers which prefer certain food sources are often found in high abundance on their host and as a result, understanding the interaction between the two is important to understand community structure. The effects of intraspecific diversity, however ...
DOI:
10.1007/s10886-022-01358-2

19. Three undescribed monoterpene rhamnosides from the aerial parts of Vangueria agrestis

Author:
Ahmed G. Osman; Omer Fantoukh; Zulfiqar Ali; Vijayasankar Raman; Mohamed A. Ibrahim; Ikhlas A. Khan
Source:
Natural product research 2021 v.35 no.21 pp. 3714-3722
ISSN:
1478-6427
Subject:
monoterpenoids,   etc   ; Vangueria; research; rutin; saponins;     Show all 5 Subjects
Abstract:
... Phytochemical investigation of the methanolic extract of Vangueria agrestis aerial parts led to the isolation and characterization of four monoterpene rhamnosides, two ursane saponins, and six flavonoid glycosides. Of these constituents, are three undescribed monoterpene glycosides, vangagrestosides A-C. The reported constituents comprise the monoterpene glycoside [(2E,6Z)−2,6-dimethyl-8-[O-α-L-rh ...
DOI:
10.1080/14786419.2020.1731744

20. Arboduridine, a hexacyclic caged monoterpenoid indole incorporating cyclohexane, piperidine, and bridged-fused pyrrolidine-tetrahydrofuran moieties

Author:
Soon-Kit Wong; Yi-Sheng Tan; Siew-Huah Lim; Yun-Yee Low; Toh-Seok Kam
Source:
Tetrahedron letters 2022 v.98 pp. 153836
ISSN:
0040-4039
Subject:
monoterpenoids,   etc   ; cyclohexanes; indole alkaloids; piperidines;     Show all 4 Subjects
Abstract:
... A new monoterpenoid indole alkaloid, arboduridine (1), characterized by a hexacyclic cage skeleton, incorporating cyclohexane, piperidine, and bridged-fused pyrrolidine-tetrahydrofuran moieties, was isolated from a Malayan Kopsia species. The structure of the alkaloid was determined based on analysis of the NMR and MS data, while the absolute configuration was established by ECD measurements in co ...
DOI:
10.1016/j.tetlet.2022.153836