The structure of velutinol A, an anti‐inflammatory compound with a novel pregnane skeleton

Yunes, Rosendo A.; Pizzolatti, Moacir Geraldo; Santana, Antônio Euzébio Goulart; Hawkes, Geoffrey E.; Calixto, João B.

doi:10.1002/pca.2800040205

Cited by 21 publications

(9 citation statements)

References 19 publications

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“…The phytochemical studies of this plant have allowed the isolation and identification of velutinol A (1), a unique compound con-sisting of a 15,16-seco-14β,17α-pregn-5-ene core with cagelike framing in the D, E, and F rings, from M. velutina rhizomes in 1993 by Calixto and co-workers ( Figure 1). [5] Further pharmacological studies showed that 1 has potent anti-inflammatory activity and behaves as a selective antagonist for the B1R subtype. [6] To the best of our knowledge, 1 is the first and only B1R antagonist among nonpeptide natural products to be published to date.…”

Section: Introductionmentioning

confidence: 99%

A Concise Total Synthesis of the Non‐peptide Bradykinin B1 Receptor Antagonist Velutinol A

et al. 2011

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A concise route to the bradykinin B1 receptor antagonist velutinol A, a natural product isolated from the rhizomatous of mandevilla velutina (Apocynaceae), has been developed. This synthesis features the highly regioselective construction of Δ 14 silyl enol ether 13 from diol 8a followed by stereoselective introduction of a sterically hindered β-hydroxy group at the C14 position by Rubottom oxidation. A prolonged reaction time and the presence of an excess amount of mCPBA

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Section: Introductionmentioning

confidence: 99%

A Concise Total Synthesis of the Non‐peptide Bradykinin B1 Receptor Antagonist Velutinol A

et al. 2011

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“…The compound of interest was extracted from lyophilized cells with 2 volumes of ethyl acetate at 4ºC/7 days. The extract was filtered, concentrated under reduced pressure (crude extract), followed by the isolation of velutinol A by column chromatography on silica gel, using methylene chloride with increasing amounts of ethyl acetate as eluent (23). The presence of the compound in the column effluent was monitored by TLC on silica gel (Kilselgel 60 F 254 , 0.25 mm, Merck, Darmstadt, Germany), using hexane:diisopropyl ether:acetone (4:4:3) as the solvent system.…”

Section: Chromatographic Analysis Of Velutinol Amentioning

confidence: 99%

Somaclonal variation: a morphogenetic and biochemical analysis of Mandevilla velutina cultured cells

Maraschin

Sugui

Wood

et al. 2002

Braz J Med Biol Res

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Cell cultures of Mandevilla velutina have proved to be an interesting production system for biomass and secondary metabolites able to inhibit the hypotensive activity of bradykinin, a nonapeptide generated in plasma during tissue trauma. The crude ethyl acetate extract of cultured cells contains about 31-to 79-fold more potent anti-bradykinin compounds (e.g., velutinol A) than that obtained with equivalent extracts of tubers. Somaclonal variation may be an explanation for the wide range of inhibitor activity found in the cell cultures. The heterogeneity concerning morphology, differentiation, carbon dissimilation, and velutinol A production in M. velutina cell cultures is reported. Cell cultures showed an asynchronous growth and cells in distinct developmental stages. Meristematic cells were found as the major type, with several morphological variations. Cell aggregates consisting only of meristematic cells, differentiated cells containing specialized cell structures such as functional chloroplasts (cytodifferentiation) and cells with embryogenetic characteristics were observed. The time course for sucrose metabolism indicated cell populations with significant differences in growth and metabolic rates, with the highest biomass-producing cell line showing a cell cycle 60% shorter and a metabolic rate 33.6% higher than the control (F 2 cell population). MALDI-TOF mass spectrometric analysis of velutinol A in selected cell lines demonstrated the existence of velutinol A producing and nonproducing somaclones. These results point to a high genetic heterogeneity in general and also in terms of secondary metabolite content.

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“…Illustrol and its derivatives isolated from Mandevilla illustris are instead 14,15-seco-21-nor-pregnane derivatives, characterized by the opening of ring D between C-14 and C-15 and by the occurrence of two ketal functions on C-14 and C-20 generating three five-membered rings but without a methyl group at C-20 [48][49][50]. 15,16-Secopregnanes isolated from Mandevilla velutina showed the opening of the ring D between C-15 and C-16 and the presence of one ketal function on C-16 and one hemiketalic function on C-15 generating one six-membered ring and two five-membered rings [45][46][47]. Another secopregnane-type skeleton more present in the family Asclepiadaceae and particularly in Cynanchum spp.…”

Section: Chemistrymentioning

confidence: 98%

“…[36][37][38][39][40][41][42][43] and Tylophora tanakae [44], and from Mandevilla spp. (Apocynaceae) [45][46][47][48][49][50][51]. From Cynanchum spp.…”

Section: Chemistrymentioning

confidence: 99%

Solenostemma argel: A Rich Source of Very Unusual Pregnane and 14,15- Secopregnane Glycosides with Antiproliferative Activity

Perrone¹,

Plaza²,

Hamed³

et al. 2008

COC

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Solenostemma argel Hayne (Asclepiadaceae) is an Egyptian plant whose leaves are commonly used in traditional medicine as a purgative, antipyretic and antispasmodic remedy. From the pericarps, hairy seeds and leaves fifteen new 14,15-secopregnane glycosides, namely argelosides A-J, and nine new 15-ketopregnane glycosides, namely stemmosides C-K, have been isolated. Argelosides A-J show very unusual structures characterized by the opening of ring D between C-14 and C-15, and the occurrence of two ketal functions on C-14 and C-20 generating three five-membered rings with oxygenated functions in positions 16 and 15, respectively. Stemmosides D-J are characterized by the occurrence of an uncommon 14 proton configuration while stemmosides E and F possess in addition a rare enolic function in C-16. Apparently these compounds are the first pregnanes isolated from plants known to have a 15 keto, cis CD ring junction. On the other hand, stemmosides C, D and G-K are the only natural compounds which display an unusual C-17 side chain and no substitution in C-12. On the basis of antitumor and cytotoxic activities reported for pregnane and their glycosides and considering the very unusual structural features of argelosides and stemmosides, the antiproliferative activity of these compounds against Kaposi's sarcoma cells was evaluated. Thus a dose dependence study was performed to test the effects of compounds on the VEGF-induced KS cell proliferation in a concentration range 0.1-20 μM. Results indicated that 15-keto-pregnane glycosides and 14,15-secopregnane glycosides reduced the VEGF-induced KS cell proliferation in a dose-dependent manner and the highest reduction occurred at concentration of 10 μM.

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The structure of velutinol A, an anti‐inflammatory compound with a novel pregnane skeleton

Abstract: The isolation and purification of velutinol A, a potent anti‐inflammatory agent from Mandevilla velutina is reported together with spectroscopic evidence which shows that the structure comprises a novel pregnane skeleton.

Cited by 21 publications

References 19 publications

A Concise Total Synthesis of the Non‐peptide Bradykinin B1 Receptor Antagonist Velutinol A

A Concise Total Synthesis of the Non‐peptide Bradykinin B1 Receptor Antagonist Velutinol A

Somaclonal variation: a morphogenetic and biochemical analysis of Mandevilla velutina cultured cells

Solenostemma argel: A Rich Source of Very Unusual Pregnane and 14,15- Secopregnane Glycosides with Antiproliferative Activity

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