Isolation and Structural Elucidation of Two Plant Ecdysteroids, Gerardiasterone and 22-Epi-20-hydroxyecdysone

Báthori, Mária; Máthé, Imre; Girault, J. P.; Kalász, Huba; Lafont, René

doi:10.1021/np970124y

Cited by 12 publications

(5 citation statements)

References 7 publications

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“…One of the most common and abundant ecdysteroids, 20-hydroxyecdysone (20-HE), is found in many plants including widely cultivated species like Spinacia oleracea (spinach) (Bathori, Mathe, Girault, Kalasz, & Lafont, 1998). Ecdysteroids have also been reported to have effects in mammals, including lowering cholesterol levels and blood glucose (Dinan, Harmatha, Volodin, & Lafront, 2009;Mironova, Kholodova, Skachkova, Bondar, & Datsenko, 1982;Yoshida, Otaka, Uchiyama, & Ogawa, 1971).…”

Section: Introductionmentioning

confidence: 99%

20-Hydroxyecdysone attenuates TGF-β1-induced renal cellular fibrosis in proximal tubule cells

Hung

Chen

Liu

et al. 2012

Journal of Diabetes and its Complications

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Section: Introductionmentioning

confidence: 99%

20-Hydroxyecdysone attenuates TGF-β1-induced renal cellular fibrosis in proximal tubule cells

Hung

Chen

Liu

et al. 2012

Journal of Diabetes and its Complications

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“…20) On the basis of these results, it is feasible to conclude that the stereochemistry of the hydroxy group at C-22 is of pivotal importance for the molting hormonal activity. Even though 21) Hedtmann et al reported that their synthetic 22-epi-20E showed neither ES receptor binding nor molting hormonal activity.…”

Section: Cs/poa Hybrid Compoundsmentioning

confidence: 98%

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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“…Based on the spectral analysis ( [8,9]. However, this is the first time this structure or compound was established in Vitex doniana sweet.…”

Section: Test For Terpenoidsmentioning

confidence: 99%

Isolation and Structural Elucidation of 20 Hydroxyecdystone from Vitex doniana Sweet Stem bark (Black plum) Mustapha

Tijjani¹,

Ya²,

Fi³

et al. 2017

Med chem (Los Angeles)

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Vitex doniana Sweet, a plant commonly known black plum, in English, Prunier noir in French, dinya in Hausa, ucha koro in Igbo, oori-nla in yoruba and ngarmi in Kanuri is a medium-sized deciduous tree, 8-18 m high, with a heavy rounded crown and a clear bole up to 5 m. V. doniana is from Verbenaceae family and abundantly occurring in savannah regions. It can be found throughout tropical Africa. The ethanolic extract of Vitex doniana stem bark (11.9 g) was subjected to a silica gel accelerated column chromatography and eluents fractions (150 ml aliquots) obtained were collected and monitored with thin layer chromatography (TLC). Fractions with similar R f values from same solvents system were poled together. Phytochemical test of all the fractions were perform. Complete elution yielded 48 fractions (150 ml/fraction) which were pooled to 24 fractions and finally to eight (8) eight fractions and coded. Fraction Vd 8-a (56 mg) has gave a single spot a white crystal compound coded V 1 on checking with TLC and observed under Ultraviolet lamp. The R f values was calculated to be 0.433 and melting point was found to be 241-243°C uncorrected. The infrared spectrum of compound V 1 shows prominent peaks that corresponds to OHstr (3365 cm -1 ) and C=0 (1652 cm -1 ). The 1 H NMR (400 MHZ) spectrum of compound V 1 in DMSO-d6 displayed five singlet signals. It further showed a broad singlet at δ 5.58 integrated for 1 H is due to an olefinic H-atom adjacent to the carbonyl carbon atom. Three signals at δ 3.10` (d, J = 9.0 Hz, H-22), 3.59 (m, 1H, 2H-a) and 3.72 (m, 1H, 3H-e) each integrating for one proton is due to an oxymethine protons indicating that three oxymethine H-atoms were present in the compound. The 13 C-NMR spectrum showed the presence of 27 Carbon atoms, suggesting that may be steroid skeleton and the DEPT-135 spectra showed the presence of five CH 3 , eight CH 2 , and seven CH groups, and seven quaternary C-atoms. The Molecular formula was established as C 27 H 44 O 7 by HRES-MS positive ion mode m/z 481.3179. Based on the spectral analysis, the compound V 1 is thus concluded to have ecdysteriod skeleton and conclusively conforms with 2β, 3β 14α, 20R, 22R, 25-hexahydroxy-5 β cholest-7-ene-6-one, commonly known as 20-hydroxyecdysone. This is the first time this compound was isolated from Vitex doniana sweet.

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Isolation and Structural Elucidation of Two Plant Ecdysteroids, Gerardiasterone and 22-Epi-20-hydroxyecdysone

Cited by 12 publications

References 7 publications

20-Hydroxyecdysone attenuates TGF-β1-induced renal cellular fibrosis in proximal tubule cells

20-Hydroxyecdysone attenuates TGF-β1-induced renal cellular fibrosis in proximal tubule cells

Structure-activity relationship studies of insect and plant steroid hormones

Isolation and Structural Elucidation of 20 Hydroxyecdystone from Vitex doniana Sweet Stem bark (Black plum) Mustapha

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