Spirobrassinin, a Novel Sulfur-containing Phytoalexin from the Daikon <i>Rhaphanus sativus</i> L. var. <i>hortensis</i> (Cruciferae)

Takasugi, Mitsuo; Monde, Kenji; Katsui, Nobukatsu; Shirata, Akira

doi:10.1246/cl.1987.1631

Cited by 99 publications

(49 citation statements)

References 2 publications

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“…The molecular formula of 1 was determined to be C 12 C-NMR and EI-MS data strongly suggested the feature of spirobrassinin derivative. 17) According to the molecular formula and the structure of 1,2,4-trisubstituted benzene indicated in 1 H-NMR spectrum, a methoxyl was suggested located at C-5 or C-6. In the heteronuclear multiple bond connectivity (HMBC) spectrum ( was racemic while the specific rotation suggested that levorotary enantiomer was a little bit more than dextrorotary enantiomer.…”

Section: Resultsmentioning

confidence: 99%

Two New Alkaloids from Capparis himalayensis

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Two new alkaloids, Capparin A (1) and B (2), along with seven known compounds 6-methoxyindoline-2,3-dione (3), wogonin (4), oroxylin A (5), kaempferol (6), apigenin (7), quercetin (8) and luteolin (9), were isolated from the whole plant of Capparis himalayensis. Their structures have been established on the basis of spectral methods and the structure of 1 was confirmed by X-ray crystallographic analysis.

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Section: Resultsmentioning

confidence: 99%

Two New Alkaloids from Capparis himalayensis

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The Brassica rapa and B. napus produce a group of sulfur-containing phytoalexins following infection with pathogens (Morrissey and Osbourn, 1999 (Pedras et al, 2006). Other known phytoalexins in this specie are isalexin , S-(−)-spirobrassinin (Takasugi et al, 1987;Kutschy et al, 2001), 1-methoxybrassitin (Takasugi et al, 1988) and brassicanal C (Monde et al, 1991).…”

Section: Nitrogen-and Sulphur-containing Compounds Phytoalexinsmentioning

confidence: 99%

Induced plant secondary metabolites for phytopatogenic fungi control: a review

Ribera

Zúñiga

2012

J. Soil Sci. Plant Nutr.

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Pathogenic fungi constitute one of the main infectious agents in plants, causing alterations during developmental stages including post-harvest. Phytopathogenic fungi are controlled by synthetic fungicides; however, the use of these is progressively restricted due to both, the harmful effects of pesticides on the environment and human health and the appearance of highly resistant fungal strains. Therefore, there is a great demand for novel natural fungicides. Higher plants are rich source of bioactive secondary metabolites of wide variety such as tannins, terpenoids, saponins, alkaloids, flavonoids, and other compounds, reported to have in vitro antifungal properties. Thus, secondary metabolites with antifungal activity represent an alternative for achieving a sustainable control of phytopathogenic fungi and to reduce the heavy reliance of synthetic pesticides used to control them. Plant antifungal metabolites may be preformed inhibitors that are present constitutively in healthy plants (phytoanticipins), or they may be synthesized de novo in response to pathogen attack or another stress conditions (phytoalexins). These molecules may be used directly or considered as a precursor for developing better fungicidal molecules. This review presents a selection of antifungal agents induced in plants during fungal attack that can be potentially used for phytopathogenic fungi control in crops.

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“…11 Indole phytoalexins have been previously shown to exert antibacterial, antifungal [5][6][7]13,14 and anticancer properties 11,[15][16][17][18] and can serve as lead compounds for anticancer drug design. Brassinin (5b) and spirobrassinin [(±)-1] are effective in inhibiting the formation of 7,12-dimethylbenz[a]anthracene (DMBA)-induced preneoplastic lesions in a mouse mammary gland.…”

Section: (±)-3a and Cis-(±)-3b With Cro3 12 Or A Mixture Of Diastereomentioning

confidence: 99%

“…4 The 44 cruciferous phytoalexins have been divided into six groups according to simple structural features. 4 A unique group of these natural products are spiroindoline structures containing a spirocyclic ring in the C-3 position [(S)-()-spirobrassinin [()-1], 5 …”

Section: Introductionmentioning

confidence: 99%

Spirocyclization reactions and antiproliferative activity of indole phytoalexins 1-methoxybrassinin and its 1-substituted derivatives

Budovsk¹,

Piltov²,

Tischlerov³

et al. 2017

Arkivoc

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The effect of the reaction temperature and the solvent on the diastereoselectivity of the spirocyclization of 1-methoxybrassinin leading to 1-methoxyspirobrassinol methyl ether was studied. 1-Acyl derivatives of 1-methoxyspirobrassinol and 1-methoxyspirobrassinol methyl ether were prepared by the bromine-mediated spirocyclization reactions of derivatives of brassinin bearing an acyl group on the indole nitrogen with water or methanol as nucleophilic agents. The cyclization of 1-acyl derivatives of brassinin afforded the trans-diastereoisomer as the major product, whereas using 1-methoxybrassinin afforded the cis-and trans-isomers in a ratio near to 1:1. Bromospirocyclization of brassinin and 1-methylbrassinin in the presence of methanol resulted in the formation of spirobrassinin and 1-methylspirobrassinin. The newly synthesized analogues of indole phytoalexins exhibited more significant antiproliferative activity against human leukemia cell lines than the natural phytoalexins.

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Spirobrassinin, a Novel Sulfur-containing Phytoalexin from the Daikon Rhaphanus sativus L. var. hortensis (Cruciferae)

Abstract: The isolation and structure elucidation of spirobrassinin, the first phytoalexin of oxindole structure from the daikon Raphanus sativus L. var. hortensis, is described.

Cited by 99 publications

References 2 publications

Two New Alkaloids from Capparis himalayensis

Two New Alkaloids from Capparis himalayensis

Induced plant secondary metabolites for phytopatogenic fungi control: a review

Spirocyclization reactions and antiproliferative activity of indole phytoalexins 1-methoxybrassinin and its 1-substituted derivatives

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