Stereoisomers of Castasterone, 3-Epicastasterone and 2,3-Diepicastasterone, in Immature Seeds of Phaseolus vulgaris

Lee, Sang Cheul; Joo, Se‐Hwan; SeongKi, Kim

doi:10.1007/s12374-010-9131-x

Cited by 7 publications

(2 citation statements)

References 16 publications

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“…This result is in good agreement with the difference regarding the plant hormonal activity between BL and CS, which showed pED 50 values of 13.6 and 12.3, respectively. In case of 2,3-diepi-CS-type analogs, such tendencies could not be observed, as their BR-like activity was extremely low (30)(31)(32)(33). This is consistent with the results of Lee et al, who reported the isolation of 2,3-diepi-CS from Phaseolus vulgaris and described very low BR-like activity.…”

Section: Structure-activity Relationship For the Side Chain Structuresupporting

confidence: 87%

“…This is consistent with the results of Lee et al, who reported the isolation of 2,3-diepi-CS from Phaseolus vulgaris and described very low BR-like activity. 30) Based on these observations, a similar recognition mechanism for the steroidal core skeleton of BRs, containing acyl-type side chains, to that BRs with alkyl-type side chains was proposed. The plant hormonal activity of a BR with an amide-type side chain was by approximately two orders of magnitude lower compared to that of the corresponding BR with an acyl-type side chain (25 vs. 20).…”

Section: Structure-activity Relationship For the Side Chain Structurementioning

confidence: 94%

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Structure-activity relationship studies of insect and plant steroid hormones

Watanabe

2015

J. Pestic. Sci.

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Ecdysteroids and brassinosteroids are steroid hormones that regulate insect molting and plant growth, respectively. In this study, novel ecdysteroids and brassinosteroids were designed and synthesized, and their biological activity was evaluated. Structureactivity relationship details between the structure of the steroid skeleton of ecdysteroids and their molting hormone receptor binding activity, as well as between the side chain structure of brassinosteroids and their plant hormonal activity were investigated. The results of these investigations suggested that in order to exhibit hormonal activity in insects or plants, the structure of the side chain in these hormones should be more important than that of the steroidal core skeleton.

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Section: Structure-activity Relationship For the Side Chain Structuresupporting

confidence: 87%

Section: Structure-activity Relationship For the Side Chain Structurementioning

confidence: 94%

Structure-activity relationship studies of insect and plant steroid hormones

Watanabe

2015

J. Pestic. Sci.

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Plant Steroids: Occurrence, Biological Significance and their Analysis

Gunaherath

Gunatilaka

2014

Encyclopedia of Analytical Chemistry

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Plant steroids constitute a diverse group of natural products. Biosynthetically, they are derived from S ‐squalene‐2,3‐epoxide via acetate‐mevalonate pathway. Among the plant steroids, phytosterols are ubiquitous in the plant kingdom. It is significant that some phytosterols have been reported to possess hypocholesterolemic activity. Withanolides are a large group of steroidal lactones with various biological activities. Brassinosteroids are a small group of plant steroids exhibiting plant growth hormonal activity. Phytoecdysteroids are polyhydroxylated plant steroids, many of which are known to exhibit anabolic effects with no undesirable side effects. Steroidal alkaloids are nitrogen‐containing plant steroids with an array of biological activities. It is noteworthy that trace amounts of cholesterol and mammalian steroidal hormones including progesterone have been detected in some plants. Analyses of plant steroids mainly utilize chromatographic methods such as thin‐layer chromatography ( TLC ), high performance liquid chromatography ( HPLC ), ultra high performance liquid chromatography ( UHPLC ), and gas liquid chromatography ( GLC ), while photodiode array ( PDA ), evaporative light scattering ( ELS ), and fluorescence ( FL ) detectors and mass spectrometry ( MS ) are commonly used for their detection, quantification, and identification. Some less common techniques employed for the analyses of plant steroids are immunoassays and biological assays.

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Plant Steroids: Occurrence, Biological Significance, and Their Analysis

Gunaherath¹,

Gunatilaka²

2020

Encyclopedia of Analytical Chemistry

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Plant steroids constitute a diverse group of natural products. Biosynthetically, they are derived from S ‐squalene‐2,3‐epoxide via acetate‐mevalonate pathway. Among the plant steroids, phytosterols are ubiquitous in the plant kingdom and some of them are reported to possess hypocholesterolemic activity. Withanolides are a large group of steroidal lactones with various biological activities. Brassinosteroids are a small group of plant steroids classified as plant growth hormones. Phytoecdysteroids are polyhydroxylated plant steroids, many of which are known to exhibit anabolic effects with no undesirable side effects. Steroidal alkaloids are nitrogen‐containing plant steroids with an array of biological activities. It is noteworthy that trace amounts of cholesterol and mammalian steroidal hormones including progesterone have been detected in some plants. Analyses of plant steroids mainly utilize chromatographic methods such as thin‐layer chromatography ( TLC ), high‐performance liquid chromatography ( HPLC ), ultra‐high‐performance liquid chromatography ( UHPLC ), and gas‐liquid chromatography ( GLC ). In general, photodiode array ( PDA ), evaporative light scattering ( ELS ), and fluorescence ( FL ) detectors and mass spectrometry ( MS ) are commonly used for detection, quantification, and identification of plant steroids. UHPLC hyphenated with tandem mass spectrometry ( MS/MS ) has recently become the state‐of‐the‐art method of choice for the analysis of plant steroids, especially for the ones that are present in minor quantities such as brassinosteroids and phytoecdysteroids. Some less common techniques employed for the analyses of plant steroids are immunoassays and biological assays.

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Stereoisomers of Castasterone, 3-Epicastasterone and 2,3-Diepicastasterone, in Immature Seeds of Phaseolus vulgaris

Cited by 7 publications

References 16 publications

Structure-activity relationship studies of insect and plant steroid hormones

Structure-activity relationship studies of insect and plant steroid hormones

Plant Steroids: Occurrence, Biological Significance and their Analysis

Plant Steroids: Occurrence, Biological Significance, and Their Analysis

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