Chemical constituents from pine needles of Cedrus deodara

Abstract

The plant Cedrus deodara (Roxb.) Loud. belonging to the Pinus (Pinaceae) is an evergreen tree growing extensively on the slopes of the Himalayas. The wood of Cedrus deodara has been used since ancient days in Indian medical practice for the treatment of inflammations and rheumatoid arthritis. It is recorded in the dictionary of Chinese Crude Drugs as an effective herbal drug for expelling wind, removing dampness, destroying parasites, and relieving itching. Its indications are wind-colddampness arthralgia, traumatic injury, sleeplessness, edema, eczema, and acariasis. In recent years, pine needles are used for rheumatism, cardiovascular diseases, diabetes, obesity, liver and stomach diseases, gonorrhea, chronic bronchitis, cancer, etc.[1]. No phytochemical work on the needles of this genus has so far been reported. The medicinal importance of Cedrus deodara prompted us to carry out phytochemical investigations on this genus.In the present work, we isolated and elucidated the structure of one new phenylpropanoid 1 along with nine known compounds 2-10, all of which were obtained from this plant for the first time.The pine needles of Cedrus deodara were collected from Lanzhou City of Gansu province of China in June 2008.The plant sample was identified by Prof. Fu Jiang He at Gansu Academy of Medical Science. The air-dried pine needles of Cedrus deodara (3.5 kg) were extracted with 95% ethanol (10 times volume) three times to afford an ethanol extract (390 g) that was suspended in water, and extracted with petroleum ether, ethyl acetate, and n-butanol, separately. The petroleum ether residue (51 g) was chromatographed on a silica gel column gradiently eluted with petroleum ether-ethyl acetate (9:1, 8:2, 7:3, 6:4, 5:5, 4:6, 3:7, 2:8, 1:9 v/v) to yield compounds 2 (65 mg), 4 (26 mg), 5 (31 mg), 6 (23 mg), and 7 (27 mg). The n-butanol extract (130 g) was chromatographed over Diaion HP-20 with H 2 O containing increasing amounts of MeOH. The 20% MeOH eluate (3.4 g) was chromatographed on Toyopearl HW-40 (coarse grade) developing with 20% MeOH-50% MeOH. The 30% MeOH eluate (1.8 g) was rechromatographed on silica gel and Sephadex LH-20 to yield compound 1 (35 mg), 3 (35 mg), 8 (21 mg), 9 (26 mg), and 10 (37.7 mg).The structures of these compounds were confirmed by 1 H NMR, 13 C NMR, and MS. Besides compound 1, the data of other compounds were in good agreement with the respective literature data.The ESI-MS of compound 1 gave an [M -H] -ion at m/z 325, which indicated that the molecular formula of compound 1 was C 15 H 18 O 8 . The characteristic signals for 1,4-disubstituted benzene protons at G 7.556 (2H, d, J = 7.6 Hz) and 7.124 (2H, d, J = 7.6 Hz) and the pair of trans-olefinic proton signals at G 7.642 (1H, d, J = 16.0 Hz) and 6.381 (1H, d, J = 16.0 Hz), which were conjugated with a carbonyl group, clearly indicated that there is a trans-coumaroyl moiety in the structure. The anomeric proton signal at G 4.996 (1H, d, J = 4.4 Hz) of the sugar unit demonstrated D-D-configuration. Therefore, compound 1 was identified as 1...

First separation of four aromatic acids and two analogues with similar structures and polarities from Clematis akebioides by high‐speed counter‐current chromatography

“…1 H NMR data of peak 2 in Fig 3: 1 H NMR (400 MHz, DMSO‐d 6 ): δ 12.53 (1H, s, –COOH), 9.99 (2H, s, –OH), 7.33 (1H, d, J = 2.0 Hz, 2‐H), 7.28 (1H, dd, J = 2.0, 8.0 Hz, 6‐H), 6.78 (1H, d, J = 8.0 Hz, 5‐H); 13 C NMR (101 MHz, DMSO‐d 6 ): δ 167.35 (C‐7), 150.01 (C‐4), 144.90(C‐3), 121.91 (C‐6), 121.71 (C‐1), 116.58 (C‐2), 115.17 (C‐5). Compared with the data given in , peak 2 corresponded to protocatechuic acid.…”

“…1 H NMR data of peak 2 in -5). Compared with the data given in [19], peak 2 corresponded to protocatechuic acid. .…”

Screening of Panamanian Plants for Cosmetic Properties, and HPLC-Based Identification of Constituents with Antioxidant and UV-B Protecting Activities

“…Isoquercitrin ( 10 ) almost completely blocked cell death. Three minor peaks ( 7 , 11 , and 12 ) in the active time window were enriched in fraction PA2, and were identified as protocatechuic acid ( 7 ) [ 28 ], guaijaverin ( 11 ) [ 29 ], and quercetin ( 12 ) [ 30 ]. Compound 7 could only be obtained at 90% purity, with traces of phenolic glycosides as contaminants.…”

Screening of Panamanian Plant Extracts for Pesticidal Properties, and HPLC-Based Identification of Active Compounds

“…The extract was filtered over polyamide, and five tannin-depleted fractions were obtained ( Fig 4S , Supporting Information). Compounds in the active time windows were purified by HPLC, and identified as neochlorogenic acid ( 24 ) [ 37 , 38 ], protocatechuic acid ( 25 ) [ 39 ], quercetin-3,7- O -α-dirhamnopyranoside ( 26 ) [ 40 ], 5- O -β-glucopyranosylombuin-3- O -β-rutinoside ( 27 ) [ 41 ], and rutin ( 28 ) [ 42 ]. However, none of the flavonoids showed activity in the herbicidal assay when tested as pure compounds.…”