Chemical Constituents of the Roots of Clerodendrum paniculatum

Abstract

The genus Clerodendrum belongs to the family Verbenaceae and consists of about 30 species. It is mainly distributed in Thailand, India, and China. From the plants of this genus were isolated abietane diterpenoids, iridoids, phenylethanoid glycosides, triterpenes, and saponins. Some of them have been reported to possess many biological activities, including antimalarial, antitumor, anti-HIV [1], and antiasthmatic activities [2].Clerodendrum paniculatum L. is commonly known as glorybower, bagflower, and bleeding-heart. It is a shrub, liana, or small tree. There are no reports on phytochemical investigations of this plant. In continuation of our search for anticancer compounds of Thai medicinal plants, we have examined the CH 2 Cl 2 extract of this plant for cytotoxic constituents [3]. The roots of this plant were collected from Khon Kaen Province in September 2011 and identified by Dr. Suttira Khumkratok, a botanist at the Walairukhavej Botanical Research Institute, Mahasarakham University, and a specimen was retained as a reference .The dried roots of C. paniculatum (5.13 kg) were extracted with CH 2 Cl 2 at room temperature. The solvent was evaporated in vacuo to give the CH 2 Cl 2 extract (23.37g). This extract was chromatographed on a silica gel column eluted with gradient systems of hexane, CH 2 Cl 2 , EtOAc, and MeOH. Then the compounds were separated and purified using various chromatrographic methods such as open-column chromatography, preparative thin-layer chromatography, chromatotron, and Sephadex LH-20 chromatography to afforded compounds 1-6. The six compounds were found to be identical with E-sitosterol (1) [4], lupeol (2) [5], oleanolic aldehyde acetate (3) [6], stigmasta-4,25-dien-3-one (4) [7], (22E)-stigmasta-4,22,25-trien-3-one (5) [7], and (3E-stigmasta-4,22,25-trien-3-ol (6) [7]. The isolated compounds were identified by a combination of spectroscopic methods ( 1 H NMR, 13 C NMR, and MS) as well as by comparison with the literature and authentic samples. Compounds 1-6 were isolated from this plant for the first time.All isolated compounds were tested for their cytotoxicity against KB and HeLa cell lines. Oleanolic aldehyde acetate (3) showed significant cytotoxic activity against the KB cell line with an IC 50 value of 9.58 Pg/mL. On the other hand, (3E)-stigmasta-4,22,25-trien-3-ol (6) also exhibited moderate cytotoxic activity against the KB cell line with an IC 50 value of 13.14 Pg/mL. The standard agent (adriamycin) showed an IC 50 value of 0.018 Pg/mL against both cell lines. E-Sitosterol (1), colorless needles. ESI-MS m/z 415 [M + H] + . This compound is identical to an authentic sample. Lupeol (2), colorless needles, mp 215qC [5]. Oleanolic aldehyde acetate (3), white crystals. 1 H NMR (400 MHz, CDCl 3 , G, ppm, J/Hz): 0.74 (3H, s, H-26), 0.87 (3H, s, H-24), 0.90 (3H, s, H-23), 0.93 (3H, s, H-30), 0.94 (3H, s, H-25), 0.94 (3H, s, H-29), 1.16 (3H, s, H-27), 1.46 (1H, dd, J = 16.0, 8.0, H-9), 1.89 (1H, d, J = 8.0, H-2), 1.89 (1H, d, J = 8.0, H-22), 1.98 (1H, dt, J = 16.0, 4.0, H-11), 2.07 ...

Optimization of Pagoda (Clerodendrum Paniculatum L.) Extraction Based by Analytical Factorial Design Approach, Its Phytochemical Compound, and Cytotoxicity Activity

“…Several types of compounds have been successfully isolated. These include terpenes, flavonoids, tannins, alkaloids, phenolic acid, sterols, and glycosides [8,9], quercetin [10], 24S-methyl cholesta-5,22,25-triene-3β-ol, α-amyrin, β-sitosterol [11], oleanolic aldehyde acetate, β-sitosterol, lupeol, stigmasta-4,25-dien-3-one-22E-stigmasta-4,22,25trien-3-one, 3β-stigmasta-4,22,25-trien-3-ol [12]. Leaves contain tannins, phenols, sterols, routine, and quercetin [10].…”

Ethnobotanical uses, phytochemistry and biological activities of Clerodendrum paniculatum L. (Lamiaceae): A comprehensive review

“…The plant is reported to have traditional medicinal values and is shown to exhibit a range of biological activities. 8,[13][14][15][16] In the present review, we present an updated information on the ethnomedicinal uses, phytochemistry and biological activities of C. paniculatum by an intensive literature survey carried out by referring standard flora, journals and online search engines viz. PubMed, ScienceDirect and Google Scholar.…”