Cucumol A: a cytotoxic triterpenoid from <i>Cucumis melo</i> seeds

Ibrahim, Sabrin; Al Haidari, Rwaida; Mohamed, Gamal; Elkhayat, Ehab; Moustafa, Mohamed

doi:10.1016/j.bjp.2016.03.012

Acessibilidade / Reportar erro

Brasil

Revista Brasileira de Farmacognosia

Español English

Brasil

Español English

sumário « anterior atual seguinte »

Sumário

Original articles • Rev. bras. farmacogn. 26 (6) • Nov-Dec 2016 • https://doi.org/10.1016/j.bjp.2016.03.012 copy

Cucumol A: a cytotoxic triterpenoid from Cucumis melo seeds

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

Phytochemical investigation of the MeOH extract of Cucumis melo L. var. reticulates, Cucurbitaceae, seeds led to the isolation of a new triterpenoid: cucumol A (27-hydroxy taraxerol-3β-ol), along with three known compounds: α-spinasterol and D:B-friedoolean-5-ene-3-β-ol. Their structures were established by extensive 1D (¹H, ¹³C, and DEPT) and 2D (¹H–¹H COSY, HMQC, and HMBC) NMR, as well as IR and HRESIMS spectral analyses. Compound 3 displayed cytotoxic activity against L5178Y and Hela cancer cell lines with ED₅₀ of 1.30 and 5.40 µg/ml, respectively compared to paclitaxel (0.07 and 0.92 µg/ml, respectively).

Keywords:
Cucumis melo; Cucurbitaceae; Triterpenoid; Cucumol A; Cytotoxic activity

No.	δ_H [mult., J (Hz)]	δ_C (mult.)	HMBC
1	1.51 m 1.47 m	37.7 (CH₂)	–
2	2.05 m 1.83 m	28.0 (CH₂)	3
3	3.42 dd (9.2, 6.6)	78.1 (CH)	5, 24
4	–	39.2 (C)	–
5	0.81 dd (9.6, 1.3)	55.9 (CH)	1, 4, 6, 24
6	1.53 m 1.34 m	19.1 (CH₂)	–
7	1.92 m 1.89 m	41.6 (CH₂)	14
8	–	39.4 (C)	–
9	1.42 m	49.5 (CH)	–
10	–	38.7 (C)	–
11	1.64 m 1.41 m	17.8 (CH₂)	–
12	1.31 m 1.27 m	33.2 (CH₂)	–
13	–	41.1 (C)	–
14	–	158.6 (C)	–
15	5.62 dd (10.6, 4.3)	116.8 (CH)	8, 13, 17
16	2.68 dd (13.8, 10.6) 1.86 dd (13.8, 4.3)	31.7 (CH₂)	14, 15, 17, 18, 27, 15
17	–	41.1 (C)	–
18	0.70 dd (10.8, 4.8)	45.5 (CH)	14, 27
19	1.50 m 1.03 m	36.8 (CH₂)	–
20	–	38.7 (C)
21	–	28.4 (CH₂)	–
22	1.62 m 1.46 m	33.8 (CH₂)	–
23	1.21 s	28.6 (CH₃)	3, 4, 5, 24
24	1.05 s	16.4 (CH₃)	3, 4, 5, 23, 25
25	0.92 s	15.6 (CH₃)	1, 5, 9, 24
26	1.08 s	26.2 (CH₃)	7, 9, 14
27	3.59 d (11.8) 3.44 d (11.8)	64.5 (CH₂)	12, 14, 16, 18, 16
28	1.02 s	33.7 (CH₃)	18, 19, 21
29	0.98 s	30.1 (CH₃)	19, 21, 30
30	1.09 s	21.9 (CH₃)	21, 22, 29
OH	5.96 brs	–	–
OH	5.75 brs	–	–

Sociedade Brasileira de Farmacognosia Universidade Federal do Paraná, Laboratório de Farmacognosia, Rua Pref. Lothario Meissner, 632 - Jd. Botânico, 80210-170, Curitiba, PR, Brasil, Tel/FAX (41) 3360-4062 - Curitiba - PR - Brazil
E-mail: revista@sbfgnosia.org.br

Acompanhe os números deste periódico no seu leitor de RSS

[1] * Corresponding author. E-mail:sribrahim@taibahu.edu.sa (S. Ibrahim).