- Email: [email protected]
Additional pregnane glycoside from Baseonema acuminatum
Fitoterapia 73 Ž2002. 442᎐444
Phytochemical communication
Additional pregnane glycoside from Baseonema acuminatum V.E. Rasamisona , J.Q. Cutrone b, A.L. Okunade c,U a
Centre National d’Application des Recherches Pharmaceutiques, B.P. 702, Antananari¨ o 101, Madagascar b Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, CT 06492, USA c Department of Biology, Washington Uni¨ ersity, St. Louis, MO 63130, USA Received 2 May 2002; accepted 16 May 2002
Abstract The isolation of baseonemoside C Ž1., a new pregnane glycoside from the aerial parts of Baseonema acuminatum is reported. 䊚 2002 Elsevier Science B.V. All rights reserved. Keywords: Baseonema acuminatum; Baseonemoside C; Pregnane glycoside
Plant. Baseonema acuminatum P. Choux ŽAsclepiadaceae., aerial parts were collected in June 1991 at Ambatondrazaka, Madagascar and identified at the Botany and Ethnobotany of the Centre National d’Application des Recherches Pharmaceutiques ŽCNARP., Madagascar, where a voucher specimen N⬚ 1041 is deposited. Uses in traditional medicine and other reported activities. A decoction of the aerial parts is used for the treatment of coughs w1x. An aqueous extract has been shown to have anti-coughing, anti-anaphylactic and anti-microbial properties w2᎐5x. Previously isolated classes of constituents. Pregnane glycosides, triterpenoids, steroids and sugars w6x. U
Corresponding author. E-mail address: [email protected] ŽA.L. Okunade..
0367-326Xr02r$ - see front matter 䊚 2002 Elsevier Science B.V. All rights reserved. PII: S 0 3 6 7 - 3 2 6 X Ž 0 2 . 0 0 1 2 9 - 6
V.E. Rasamison et al. r Fitoterapia 73 (2002) 442᎐444
443
New-isolated constituents. Pregn-5-en-3,16␣ ,20Ž S .-triol 3-O--D-cymaropyranosyl-Ž1 ª 4.--D-digitoxopyranoside 20-O--D-glucopyranosyl-Ž1 ª 2.--D-6-deoxyglucopyranoside Žbaseonemoside C. Ž1. Žyield: 0.0007% on dried wt..
Baseonemoside C Ž1.. Mp 232᎐234 ⬚C; 1 H-NMR Ž500 MHz, CD3 OD.: ␦ 0.75 Ž3H, s, H-18., 1.02 Ž3H, s, H-19., 1.23 Ž3H, d, J 6.6 Hz, H-6⬘., 1.24 Ž3H, d, J 6.5 Hz, H-6⬙ ., 1.28 Ž3H, d, J 7.7 Hz, H-6⬘⬙ ., 1.38 Ž3H, d, J 6 Hz, H-21., 1.42 Ž1H, m, H-17., 1.60᎐2.20 Ž2H, m, H-2⬙ ., 1.65᎐1.99 Ž2H, m, H-2⬘., 3.46 Ž3H, s, 3⬙-OMe ., 3.50 Ž1H, m, H-3., 3.64᎐3.83 Ž2H, m, H-6⬙⬙ ., 3.78 Ž1H, m, H-20., 4.32 Ž1H, m, H-16., 4.50 Ž1H, d, J 7.4 Hz, H-1⬘⬙ ., 4.80 Ž1H, d, J 7.7 Hz, H-1⬙⬙ ., 4.85 Ž1H, d, J 11 Hz, H-1⬙ ., 4.96 Ž1H, d, J 9 Hz, H-1⬘., 5.40 Ž1H, br s, H-6.; 13 C-NMR Ž125 MHz, CD3 OD.: 39.4 ŽC-1., 31.7 ŽC-2., 77.5 ŽC-3., 40.4 ŽC-4., 136.9 ŽC-5., 118.7 ŽC-6., 33.8 ŽC-7., 33.3 ŽC-8., 51.4 ŽC-9., 38.5 ŽC-10., 23.0 ŽC-11., 40.7 ŽC-12., 44.2 ŽC-13., 54.9 ŽC-14., 35.9 ŽC-15., 75.5 ŽC-16., 67.9 ŽC-17., 16.0 ŽC-18., 21.3 ŽC-19., 80.4 ŽC-20., 24.5 ŽC-20., 94.5 ŽC-1⬘., 38.9 ŽC-2⬘., 67.3 ŽC-3⬘., 81.8 ŽC-4⬘., 68.4 ŽC-5⬘., 20.1 ŽC-6⬘., 97.9 ŽC-1⬙ ., 36.2 ŽC-2⬙ ., 77.5 ŽC-3⬙ ., 71.9 ŽC-4⬙ ., 70.2 ŽC-5⬙ ., 20.3 ŽC-6⬙ ., 57.6 Ž3⬙-OMe ., 101.3 ŽC-1⬘⬙ ., 78.6 ŽC-2⬘⬙ ., 73.0 ŽC-3⬘⬙ ., 74.5 ŽC-4⬘⬙ ., 70.8 ŽC-5⬘⬙ ., 18.5 ŽC-6⬘⬙ ., 101.7 ŽC-1⬙⬙ ., 74.2 ŽC-2⬙⬙ ., 76.5 ŽC-3⬙⬙ ., 69.7 ŽC-4⬙⬙ ., 76.8 ŽC-5⬙⬙ ., 61.8 ŽC-6⬙⬙ .; ESIMSrMS Žpositive mode. mrz: 939 wM q Naxq, 795 wM q Na-Cymxq, 777 wM q NaGluxq, 665 wM q Na-Cym-Digxq, 631 wM q Na-Glu-DeoxyGluxq, 335 wAglycon q Hxq, 317 wAglycon q H-H 2 Oxq, 299 wAglycon q H-2H 2 Oxq, 281 wAglycon q H3H 2 Oxq. The 1 H-NMR and 13 C-NMR assignments were confirmed through 1 H᎐ 1 H COSY, HMQC, HMBC experiments and data reported for related compounds w6x.
References w1x Rabesa ZA. Pharmacopee ´ de l’Alaotra, Madagascar. Fanantenana, Antananarivo, 1986. w2x Andriantsiferana R, Rajaomaria M, Randriantsoa A. Arch CNARP 1983;2:133.
444
V.E. Rasamison et al. r Fitoterapia 73 (2002) 442᎐444
w3x Ratsimbason AM, Rasamison VE, Razafindrabeaza T, Rahelinirina L. Revue Med Pharm Afr 1997-1998;11᎐12:143. w4x Ratsimbason AM. Doctorat Thesis. University of Antananarivo, Madagascar, 1987. w5x Andriantsoa M, Andriantsiferana R. Arch CNARP 1983;2:179. w6x Rasamison VE, Okunade AL, Ratsimbason AM, Rafidinarivo E. Fitoterapia 2001;72:5.
Phytochemical communication
Additional pregnane glycoside from Baseonema acuminatum V.E. Rasamisona , J.Q. Cutrone b, A.L. Okunade c,U a
Centre National d’Application des Recherches Pharmaceutiques, B.P. 702, Antananari¨ o 101, Madagascar b Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, CT 06492, USA c Department of Biology, Washington Uni¨ ersity, St. Louis, MO 63130, USA Received 2 May 2002; accepted 16 May 2002
Abstract The isolation of baseonemoside C Ž1., a new pregnane glycoside from the aerial parts of Baseonema acuminatum is reported. 䊚 2002 Elsevier Science B.V. All rights reserved. Keywords: Baseonema acuminatum; Baseonemoside C; Pregnane glycoside
Plant. Baseonema acuminatum P. Choux ŽAsclepiadaceae., aerial parts were collected in June 1991 at Ambatondrazaka, Madagascar and identified at the Botany and Ethnobotany of the Centre National d’Application des Recherches Pharmaceutiques ŽCNARP., Madagascar, where a voucher specimen N⬚ 1041 is deposited. Uses in traditional medicine and other reported activities. A decoction of the aerial parts is used for the treatment of coughs w1x. An aqueous extract has been shown to have anti-coughing, anti-anaphylactic and anti-microbial properties w2᎐5x. Previously isolated classes of constituents. Pregnane glycosides, triterpenoids, steroids and sugars w6x. U
Corresponding author. E-mail address: [email protected] ŽA.L. Okunade..
0367-326Xr02r$ - see front matter 䊚 2002 Elsevier Science B.V. All rights reserved. PII: S 0 3 6 7 - 3 2 6 X Ž 0 2 . 0 0 1 2 9 - 6
V.E. Rasamison et al. r Fitoterapia 73 (2002) 442᎐444
443
New-isolated constituents. Pregn-5-en-3,16␣ ,20Ž S .-triol 3-O--D-cymaropyranosyl-Ž1 ª 4.--D-digitoxopyranoside 20-O--D-glucopyranosyl-Ž1 ª 2.--D-6-deoxyglucopyranoside Žbaseonemoside C. Ž1. Žyield: 0.0007% on dried wt..
Baseonemoside C Ž1.. Mp 232᎐234 ⬚C; 1 H-NMR Ž500 MHz, CD3 OD.: ␦ 0.75 Ž3H, s, H-18., 1.02 Ž3H, s, H-19., 1.23 Ž3H, d, J 6.6 Hz, H-6⬘., 1.24 Ž3H, d, J 6.5 Hz, H-6⬙ ., 1.28 Ž3H, d, J 7.7 Hz, H-6⬘⬙ ., 1.38 Ž3H, d, J 6 Hz, H-21., 1.42 Ž1H, m, H-17., 1.60᎐2.20 Ž2H, m, H-2⬙ ., 1.65᎐1.99 Ž2H, m, H-2⬘., 3.46 Ž3H, s, 3⬙-OMe ., 3.50 Ž1H, m, H-3., 3.64᎐3.83 Ž2H, m, H-6⬙⬙ ., 3.78 Ž1H, m, H-20., 4.32 Ž1H, m, H-16., 4.50 Ž1H, d, J 7.4 Hz, H-1⬘⬙ ., 4.80 Ž1H, d, J 7.7 Hz, H-1⬙⬙ ., 4.85 Ž1H, d, J 11 Hz, H-1⬙ ., 4.96 Ž1H, d, J 9 Hz, H-1⬘., 5.40 Ž1H, br s, H-6.; 13 C-NMR Ž125 MHz, CD3 OD.: 39.4 ŽC-1., 31.7 ŽC-2., 77.5 ŽC-3., 40.4 ŽC-4., 136.9 ŽC-5., 118.7 ŽC-6., 33.8 ŽC-7., 33.3 ŽC-8., 51.4 ŽC-9., 38.5 ŽC-10., 23.0 ŽC-11., 40.7 ŽC-12., 44.2 ŽC-13., 54.9 ŽC-14., 35.9 ŽC-15., 75.5 ŽC-16., 67.9 ŽC-17., 16.0 ŽC-18., 21.3 ŽC-19., 80.4 ŽC-20., 24.5 ŽC-20., 94.5 ŽC-1⬘., 38.9 ŽC-2⬘., 67.3 ŽC-3⬘., 81.8 ŽC-4⬘., 68.4 ŽC-5⬘., 20.1 ŽC-6⬘., 97.9 ŽC-1⬙ ., 36.2 ŽC-2⬙ ., 77.5 ŽC-3⬙ ., 71.9 ŽC-4⬙ ., 70.2 ŽC-5⬙ ., 20.3 ŽC-6⬙ ., 57.6 Ž3⬙-OMe ., 101.3 ŽC-1⬘⬙ ., 78.6 ŽC-2⬘⬙ ., 73.0 ŽC-3⬘⬙ ., 74.5 ŽC-4⬘⬙ ., 70.8 ŽC-5⬘⬙ ., 18.5 ŽC-6⬘⬙ ., 101.7 ŽC-1⬙⬙ ., 74.2 ŽC-2⬙⬙ ., 76.5 ŽC-3⬙⬙ ., 69.7 ŽC-4⬙⬙ ., 76.8 ŽC-5⬙⬙ ., 61.8 ŽC-6⬙⬙ .; ESIMSrMS Žpositive mode. mrz: 939 wM q Naxq, 795 wM q Na-Cymxq, 777 wM q NaGluxq, 665 wM q Na-Cym-Digxq, 631 wM q Na-Glu-DeoxyGluxq, 335 wAglycon q Hxq, 317 wAglycon q H-H 2 Oxq, 299 wAglycon q H-2H 2 Oxq, 281 wAglycon q H3H 2 Oxq. The 1 H-NMR and 13 C-NMR assignments were confirmed through 1 H᎐ 1 H COSY, HMQC, HMBC experiments and data reported for related compounds w6x.
References w1x Rabesa ZA. Pharmacopee ´ de l’Alaotra, Madagascar. Fanantenana, Antananarivo, 1986. w2x Andriantsiferana R, Rajaomaria M, Randriantsoa A. Arch CNARP 1983;2:133.
444
V.E. Rasamison et al. r Fitoterapia 73 (2002) 442᎐444
w3x Ratsimbason AM, Rasamison VE, Razafindrabeaza T, Rahelinirina L. Revue Med Pharm Afr 1997-1998;11᎐12:143. w4x Ratsimbason AM. Doctorat Thesis. University of Antananarivo, Madagascar, 1987. w5x Andriantsoa M, Andriantsiferana R. Arch CNARP 1983;2:179. w6x Rasamison VE, Okunade AL, Ratsimbason AM, Rafidinarivo E. Fitoterapia 2001;72:5.