Illustrol, a seco-norpregnane derivative from Mandevilla illustris

Yunes, Rosendo A.; Brum, Rosenei L.; Calixto, João B.; Rimplert, Horst

doi:10.1016/0031-9422(93)85360-4

Cited by 12 publications

(13 citation statements)

References 11 publications

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“…A signal at d 5.50 (d, J = 2.4 Hz) corresponds to the proton H-16 of the aglycone. The other two signals at d 5.38 (d, J = 4.8 Hz) and d 4.6 (t, J = 2.4 Hz) are attributed to the proton H-6 and H-20 of the aglycone, respectively, in accordance with the values described for illustrol and acetylillustrol [9], [13].…”

supporting

confidence: 66%

“…13 C-NMR (100.6 MHz) chemical shifts assignments for compounds 1 and 2 Shifts are in ppm related to high frequency of TMS § in CDCl 3 ; # in (CD) 3 CO.…”

mentioning

confidence: 99%

“…The 1 H-NMR and 13 C-NMR spectra of compounds 1 and 2 are summarized on Tables 1 and 2. Altogether, the spectral data allowed the complete structural elucidation of compound 1, as a new nor-pregnane 2¢,6¢-dideoxy-3¢-O-methyl-pyranosylillustrol, an illustrol derivative, already described as an M. illustris constituent [13]. The absolute configuration of 1 was established by comparison with the literature [14].…”

mentioning

confidence: 99%

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A New Anti-Oedematogenic Nor-pregnane Derivative Isolated fromMandevilla illustris

Niero

Alves²,

Filho³

et al. 2002

Planta med

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supporting

confidence: 66%

“…13 C-NMR (100.6 MHz) chemical shifts assignments for compounds 1 and 2 Shifts are in ppm related to high frequency of TMS § in CDCl 3 ; # in (CD) 3 CO.…”

mentioning

confidence: 99%

mentioning

confidence: 99%

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A New Anti-Oedematogenic Nor-pregnane Derivative Isolated fromMandevilla illustris

Niero

Alves²,

Filho³

et al. 2002

Planta med

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“…14,15-secopregnane and 14,15-seco-18-nor-pregnane derivatives, characterized by the opening of ring D between C-14 and C-15 and the occurrence of a keto function on C-14 and a furan ring at C-17, have been isolated [36,[38][39][40]43], along with 8,14-secopregnane, showing the opening of ring C between C-8 and C-14 [42]. 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].…”

Section: Chemistrymentioning

confidence: 99%

“…[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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Synthesis of the Aglycone of the Argelosides: Antiproliferative 14,15‐seco‐Pregnane Glycosides

Tamiya¹,

Isaka²,

Kitazawa³

et al. 2014

Asian J Org Chem

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The synthesis of the argeloside aglycon, the highly‐oxygenated seco‐pregnane with cage‐like D, E, and F rings, is accomplished in 13 steps starting from a readily accessible vinyl cyclopentanone derivative. The key steps involve Sharpless asymmetric dihydroxylation to set the C16 stereocenter, Baeyer–Villiger oxidation to construct the seco‐structure, and Wacker oxidation to introduce the C17 oxo groups.

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Illustrol, a seco-norpregnane derivative from Mandevilla illustris

Cited by 12 publications

References 11 publications

A New Anti-Oedematogenic Nor-pregnane Derivative Isolated fromMandevilla illustris

A New Anti-Oedematogenic Nor-pregnane Derivative Isolated fromMandevilla illustris

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

Synthesis of the Aglycone of the Argelosides: Antiproliferative 14,15‐seco‐Pregnane Glycosides

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