Chemical constituents of Pithecellobium albicans

Fitoterapia 79 (2008) 395 – 397
www.elsevier.com/locate/fitote
Phytochemical communication
Chemical constituents of Pithecellobium albicans
Gonzalo J. Mena-Rejón a,⁎, Pablo Sansores-Peraza a ,
Wendy F. Brito-Loeza a , Leovigildo Quijano b
a
Laboratorio de Química Orgánica de Investigación, Facultad de Química, Universidad Autónoma de Yucatán, Calle 41 No. 421,
Col. Industrial, C.P. 97150, Mérida, Yucatán, México
b
Instituto de Química, UNAM, Circuito Exterior, Ciudad Universitaria, Coyoacán, 04510, D.F., México
Received 2 June 2006; accepted 10 March 2008
Available online 27 May 2008
Abstract
A new ent-kaurane diterpene glycoside identified as (−)19-β-D-glucopyranosyl 6,7-dihydroxy kaurenoate, was isolated from
the seeds of Pithecellobium albicans. The structure of the new compound was established by spectral data.
© 2008 Elsevier B.V. All rights reserved.
Keywords: Pithecellobium albicans; ent-Kaurene; Diterpenoids
1. Plant
Pithecellobium albicans (Kunth) Benth (Fabaceae), seeds and leaves collected on the road Mérida–Motul (11 Km),
East of the State of Yucatán (México) in July 1997 was authenticated by Dr. José Salvador Flores Guido. A voucher
specimen (J. S. Flores 10281) has been deposited in the Herbarium “Alfredo Barrera Marin”, Universidad Autónoma
de Yucatán (UADY), Mérida, Yuc., México.
2. Uses in traditional medicine
The dry bark powder is used to heal wounds and the infusion of the bark is used against diarrhea and as an antiseptic
[1,2].
3. Previously isolated classes of constituents
None.
⁎ Corresponding author. Tel.: +52 999 9225711x114; fax: +52 999 9225716x112.
E-mail address: [email protected] (G.J. Mena-Rejón).
0367-326X/$ - see front matter © 2008 Elsevier B.V. All rights reserved.
doi:10.1016/j.fitote.2008.03.005
396
G.J. Mena-Rejón et al. / Fitoterapia 79 (2008) 395–397
Fig. 1. 19-β-D-Glucopyranosyl 6,7-dihydroxy kaurenoate (1).
4. New constituent
(−)19-β-D-Glucopyranosyl 6,7-dihydroxy kaurenoate (1, Fig. 1) (yield: 0.0005% from dried seeds), mp 150–
152 °C (MeOH); [α]D-2.9 (c 0.135, MeOH); UV max (MeOH): 221 nm (log ε 3.08); IR bands (KBr): 3383, 3065,1728,
1653 cm-1; EIMS m/z (rel. int.): 496 [M]+ (4), 480 (100), 464 (61), 450 (9), 389 (4), 297 (5), 288 (9), 267 (12), 253
(20), 241 (34), 218 (46), 189 (24), 147 (23), 121 (30), 95 (33), 81 (20); 1H and 13 C-NMR: see Table 1; acetate (2) mp
172–174 °C (MeOH); [α]D-65.9 (c 0.225, MeOH); UV max (MeOH): 212 nm (log ε 2.97); IR bands (KBr):
3050,1730, 1650 cm-1.
5. Known compounds
Gallic acid (0.007%), afzelin (0.0003%), kaempferol (0.0003%), quercetin (0.005%) and quercitrin (0.002%) from
the leaves, spinasterol β-D-glucopyranoside (0.013%) from the seeds.
Acknowledgments
The authors wish to thank the Consejo Nacional de Ciencia y Tecnología (CONACyT, México) for the financial
support (Grant 0276P-B), and Dr. Isabel López Bazzocchi, Universidad de La Laguna, Tenerife, Spain for EIMS.
References
[1] Arellano JA, Flores JS, Tun Garrido J, Cruz Bojórquez M. Nomenclatura, forma de vida, uso, manejo y distribución de las especies vegetales de
la Península de Yucatán. Etnoflora yucatanense Fascículo 20. Mérida. México: Universidad Autónoma de Yucatán; 2003.
[2] Banco de Datos Etnobotánicos de la Península de Yucatán. Universidad Autónoma de Yucatán; 2004.
G.J. Mena-Rejón et al. / Fitoterapia 79 (2008) 395–397
397
Table 1
H NMR and 13C NMR data for 1 and 2 (400 and 100 MHz, CDCl3, J in Herz and δ in ppm)
1
C
1
δC
2
δH
1
2
3
4
5
40.9
19.3
40.1
44.4
51.9
6
7
70.4 (1H, 4.30, m)
70.1 (1H, 3.17 m)
8
9
10
11
12
13
14
15
44.4
48.4
48.2
18.4
38.0
43.6
33.8
46.3
16
17
18
19
20
1’
2’
3’
4’
5’
6’
155.6
103.8
32.0
177.0
16.9
94.9
73.0
78.1
81.4
77.5
61.1
2’-OH
3’-OH
4’-OH
5’-OH
6’-OH
6-OH
a
(2H, 0.77 m, 1.70 m)
(2H, 1.30 m, 1.70 m)
(2H, 1.02 m, 2.01 m)
–
(1H, 1.69, d, J 11)
HMBC
C-4
C-1, C-4, C-6, C-7, C-18,
C-19, C-20
C-10
–
(1H.34 m)
(2H, 0.87 m, 1.45 m)
(2H, 1.15 m, 1.82 m)
(1H, 2.57 m)
(2H, 1.34 m, 1.51 m)
(2H, 2.14 m)
–
(2H, 4.72 m, 4.77 m)
(3H,m)
–
(3H,m)
(1H, 5.27, d, J 7.5)
(1H, 3.24, m)
(1H, 3.17, m)
(1H, 3.24, m)
(1H, 3.24, m)
(1Ha, 3.46,dd,J 11.4, 4.9)
(1Hb 3.63, dd,J11.4, 4.9)
(1H, 5.11,m) a
(1H, 4.98,m)
(1H,5.11,m) a
(1H, 5.11, m) a
(1H, 4.69,m)
(1H, 3.52, m)
Assignments may be interchanged.
C-9
C-13
C-4, C-5 C-19
C-1, C-5 C-19
C-19
C-2’, C-1’
C-3’
C-6’
C-6
δC
40.3
18.9
39.2
44.1
50.3
δH
(2H,0.90 m, 1.87 m)
(2H,1.45 m, 1.68 m)
(2H,1.15 m, 2.18 m)
–
(1H,1.95 m)
72.0 (1H5,5.61, dd, J 12.0, 2.0)
79.2 (1H,5.10 m)
47.1
49.2
41.2
18.0
38.0
43.3
33.3
45.0
153.2
104.2
32.2
175.2
16.9
91.2
70.3
73.1
68.1
72.6
61.8
–
1.42 m
–
(2H, 1.56 m)
(2H, 1.44 m, 1.92 m)
(1H,2.71 m)
(2H,1.45 m, 1.55 m)
(2.10, m)
–
(2H,4.74 m, 4.81 m)
(3H,m)
–
(3H,m)
(1H, 5.83, d, J 8.2)
(1H,5.23, m)
(1H, 5.23, m)
(1H, 5.10, m
(1H, 3.79, m)
(1Ha,4.01,dd,J12.3, 2.3)
(1 Hb,4.30 dd, J 12.3, 5.0)
HMBC
ROESY
H-5
C-4, C-6, C-7, C-10,
C-18, C-20
C-5, C-7, 6-CO2Me H-7, H-20
C-5, C-6, C-8,
H-15, H-14
C-9, 7-CO2Me
C-7, C-9, C-13
C-7, C-8, C-9,
C-16, C-17
C-13, C-15, C-16
C-3, C-4, C-5, C-19
C-1, C-5, C-9, C-10
C-19