Arch Pharm Res. 2016 Jul;39(7):897-911. doi: 10.1007/s12272-016-0784-y. Epub 2016 Jun 27.
Khedr AI1,
Ibrahim SR2,3,
Mohamed GA4,5,
Ahmed HE6,7,
Ahmad AS8,
Ramadan MA8,
El-Baky AE9,
Yamada K10,
Ross SA11.
- 1Department of Pharmacognosy, Faculty of Pharmacy, Port Said University, Port Said, 42526, Egypt.
- 2Department
of Pharmacognosy and Pharmaceutical Chemistry, College of Pharmacy,
Taibah University, Al Madinah Al Munawarah, 30078, Saudi Arabia.
sabrinshaur@gmail.com.
- 3Department of Pharmacognosy, Faculty of Pharmacy, Assuit University, Assuit, 71526, Egypt. sabrinshaur@gmail.com.
- 4Department
of Natural Products and Alternative Medicine, Faculty of Pharmacy, King
Abdulaziz University, Jeddah, 21589, Saudi Arabia.
- 5Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assuit Branch, Assuit, 71524, Egypt.
- 6Department
of Pharmacognosy and Pharmaceutical Chemistry, College of Pharmacy,
Taibah University, Al Madinah Al Munawarah, 30078, Saudi Arabia.
- 7Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt.
- 8Department of Pharmacognosy, Faculty of Pharmacy, Assuit University, Assuit, 71526, Egypt.
- 9Department of Biochemistry, Faculty of Pharmacy, Port Said University, Port Said, 42526, Egypt.
- 10Garden for Medicinal Plants, Graduate School of Biomedical Sciences, Nagasaki University, Bunkyo-machi 1-14, Nagasaki, 852-8521, Japan.
- 11National
Center for Natural Products Research, and Department of Pharmacognosy,
School of Pharmacy, University of Mississippi, University, MS, 38677,
USA.
Abstract
Phytochemical
investigation of Ficus pandurata Hance (Moraceae) fruits has led to the
isolation of two new triterpenoids, ficupanduratin A
[1β-hydroxy-3β-acetoxy-11α-methoxy-urs-12-ene] (11) and ficupanduratin B
[21α-hydroxy-3β-acetoxy-11α-methoxy-urs-12-ene] (17), along with 20
known compounds: α-amyrin acetate (1), α-amyrin (2),
3β-acetoxy-20-taraxasten-22-one (3), 3β-acetoxy-11α-methoxy-olean-12-ene
(4), 3β-acetoxy-11α-methoxy-12-ursene (5), 11-oxo-α-amyrin acetate (6),
11-oxo-β-amyrin acetate (7), palmitic acid (8),
stigmast-4,22-diene-3,6-dione (9), stigmast-4-ene-3,6-dione (10),
stigmasterol (12), β-sitosterol (13), stigmast-22-ene-3,6-dione (14),
stigmastane-3,6-dione (15), 3β,21β-dihydroxy-11α-methoxy-olean-12-ene
(16), 3β-hydroxy-11α-methoxyurs-12-ene (18),
6-hydroxystigmast-4,22-diene-3-one (19), 6-hydroxystigmast-4-ene-3-one
(20), 11α,21α-dihydroxy-3β-acetoxy-urs-12-ene (21), and
β-sitosterol-3-O-β-D-glucopyranoside (22). Compound 21 is reported for
the first time from a natural source. The structures of the 20 compounds
were elucidated on the basis of IR, 1D ((1)H and (13)C), 2D ((1)H-(1)H
COSY, HSQC, HMBC and NOESY) NMR and MS spectroscopic data, in addition
to comparison with literature data. The isolated compounds were
evaluated for their anti-microbial, anti-malarial, anti-leishmanial, and
cytotoxic activities. In addition, their radioligand displacement
affinity on opioid
and cannabinoid receptors was assessed. Compounds 4, 11, and 15
exhibited good affinity towards the CB2 receptor, with displacement
values of 69.7, 62.5 and 86.5 %, respectively. Furthermore, the binding
mode of the active compounds in the active site of the CB2 cannabinoid
receptors was investigated through molecular modelling.
KEYWORDS:
Anti-leishmanial; Anti-malarial; Cannabinoid receptors; Ficus pandurata; Opioid receptors; Triterpenes
