Chemical Constituents and Biological Activity of Kaempferia Angustifolia, K. Rotunda,Spermacoce Articularis and S. Exilis

Kaempferia angustifolia, K rotunda (Zingiberaceae), Spennacoce articularis and S. exilis (Rubiaceae) were chosen since they have long been used traditionally in medicinal treatment. In this research, isolation and separation work had been carried out using various solvents and chromatographic methods. The structure of these compounds were determined by using spectroscopic methods such as ineared (IR), nuclear magnetic resonance ('H, 13C and 2D- NMR), mass spectrometry (MS) and by comparison with the data reported previously. The crude extracts and some of the isolated compounds were subjected to the biological activity test: antioxidant, antimicrobial tests, cytotoxic screening and larvicidal activity.Extracts fiom Kaempferia angush~oliah ave yielded a new compound angustifolienol (58), together with seven other compounds; crotepoxide (33), p-sitosterol (a), boesenboxide (M), 2'-hydroxy-4, 4', 6'-trimethoxychalcone (Xi), 6-methylzeylenol (59), and sucrose (60), and zeylenol(35). Frationation of extracts fiom K. rotunda has yielded five pure compounds; crotepoxide (33), tetracosanoic acid (61), benzoic acid (62), stigmasterol (45) and p-sitosterol (44). Both tetracosanoic acid (61) and benzoic acid (62) are new to species. Extracts fiom S. art'iculm's gave two pure compounds, identified as ursolic acid (63) and stigmasterol (45). While the extracts from S. exilis gave four compounds, benzo[g]isoquinoline-5,IOdione (64), stigmasterol (49, hexadecanoic acid (65) and ursolic acid (63). Phytochemical studies on later species had never been reported before. Acetylations of new compound, angustifolienol (58) gave two derivatives, triacetoxyangustifolienol (66) and diacetoxyangustifolienol (67). Both are new compounds, and have never been reported previously either as natural product or synthesized compounds. The major constituents of the essential oil of K. angustifolia was DL- camphor (20.57 %), while the major constituent of K. rotunda was benzyl benzoate (49.84 %). The major constituent of the essential oil of S. articularis was phytol(10.31 %), while the major constituent of S. exilis was oleic acid (20.9 %).Cytotoxic screening showed that all the crude extracts of K angustiijolia and K. rotunab were not cytotoxic against HL-60 cell line. However, pure compounds of K. angu~hyolia showed strong activity. All crude extracts of S. articularis and S. exilis (except hexane extract of S. exilis) and ursolic acid (63) were strongly cytotoxic towards HL-60 and MCF-7 cell lines. All extracts and most of the pure compounds were subjected to four strains of microbes (MRSA, Pseudomonas aeruginosa, Salmonella typhimurium and Bacillus subtilis) in the antimicrobial test. Pet. ether extracts fiom Kaempferia species, all extracts fiom S. exilis and boesenboxide (34) were active towards some microbes. In antioxidant assay, K rotunda was more active than Kaempferia angustiyolia while both Spennacoce species were moderately active. Besides that, some of the compounds from Kaempferia angustzyolia were subjected to the antioxidant assay and showed stronger antioxidant activity than a- tocopherol. In addition, all plants also showed moderate to low larvicidal activity

Antileukemic activity and chemical constituents of some Zingiberaceae species

Crude extracts of various solvents from six species (genus Alpinia, Zingiber, Kaempferia) of Zingiberaceae family have been chosen for the in vitro cytotoxic activity screening against the inhibition of HL-60 cell line (Human promyelocytic leukemia). Eight extracts (44 %) were found to have cytotoxic activity with IC50 values less than 30 μg/mL, with Alpinia galanga showing the most prominent antileukemic activity. Further isolation work on Kaempferia galanga has yielded ethyl p-methoxy-trans-cinnamate (1), p-methoxy-trans-cinnamic acid (2) besides b-sitosterol

Larvicidal activity of some Curcuma and Kaempferia rhizome extracts against dengue fever mosquito Aedes aegypti Linnaeus (Diptera: Culicidae)

Investigations were carried out to test the larvicidal activity of extracts of some Zingiberaceae plants species against the larvae of dengue fever mosquito Aedes aegypti. Fifteen crude extracts from three Curcuma species and two Kaempferia species were used for the test. Most of these plants were toxic to the mosquito larvae and indicated promising activity with LC50 values of less than 90 μg/mL. Among the five plants, hexane extract of Curcuma xanthorrhiza was the most toxic against Aedes aegypti with LC50 value of 26.4 mg/mL. - See more at: http://www.asianjournalofchemistry.co.in/user/journal/viewarticle.aspx?ArticleID=22_10_61#sthash.a5GblrYS.dpu

Chemical constituents from two weed species of Spermacoce (Rubiaceae)

Spermacoce articularis and Spermacoce exilisare weeds commonly growing in wastel ands but widely used as traditional medicines. The separation works on the two plant species had been carried out using various solvents and chromatographic methods. The structures of the isolated compounds were determined by using spectroscopic methods such as IR, MS, 1H NMR, 13C NMR, 2D-NMR and by comparison with the data reported previously. Extracts from Spermacoce articularis gave two compounds, identified as ursolic acid (1)and stigmasterol, while extracts from Spermacoce exilis yielded four compounds, ursolic acid(1), benzo[g]isoquinoline-5, 10-dione(2), stigmasterol and hexadecanoic acid(3). There was no previous phytochemical investigation on Spermacoce exilis

Chemical constituents and bioactivities of Kaempferia rotunda L.

Phytochemical study on the rhizomes of Kaempferia rotunda originated from Yogyakarta, Indonesia has led to the isolation of crotepoxide, benzoic acid, tetracosanoic acid, b-sitosterol and stigmasterol. Tetracosanoic acid and benzoic acid have never been reported for this species previously. Bioactivity studies on the extracts and isolated compound (crotepoxide) were carried out. Extracts and crotepoxide from K. rotunda were not active against HL-60 (human promyelocytic leukemic) cell line in cytotoxic testing. However, the non-polar extract demonstrated moderate inhibition in antimicrobial assay whereas in FTC antioxidant testing, all extracts exhibited strong activity as compared to vitamin E

Antileukemic properties of spermacoce species

Antileukemic activity of th extracts and isolated compound from Spermacoce articularis, Spermacoce exilis and Spermacoce latifolia were carried out. All extracts of Spermacoce articularis as well as dichloromethane and ethyl acetate extracts of Spermacoce exilis showed strong activity against HL-60 cancer cell with IC50 value ranging from 0.4 to 7.2 μg/mL, whereas hexane extract of Spermacoce latifolia gave moderate activity with IC50 value of 13 ± 0.19 μg/mL. Ursolic acid as the major isolated constituent of these plants was found to have strong activity with IC50 of 1.3 ± 0.03 μg/mL against the same cancer cell

Chemical constituents variations of essential oils from rhizomes of four Zingiberaceae species

The essential oils were extracted using the hydrodistillation method from four ZingibeZingiber amaricans, Kaempferia galanga, and Boesenbergia pandurata were identified as E-citral (20.98%), zerumbone (40.70%), ethyl p-methoxycinnamate (58.47%) and camphor (57.97%), respectively. Kaempferia galanga and Zingiber amaricans were rich in sesquiterpenes whereas Boesenbergia pandurata and Zingiber officinale var. rubrum contained mostly monoterpenes

Natural Organochlorines as precursors of 3-monochloropropanediol esters in vegetable oils

During high-temperature refining of vegetable oils, 3-monochloropropanediol (3-MCPD) esters, possible carcinogens, are formed from acylglycerol in the presence of a chlorine source. To investigate organochlorine compounds in vegetable oils as possible precursors for 3-MCPD esters, we tested crude palm, soybean, rapeseed, sunflower, corn, coconut, and olive oils for the presence of organochlorine compounds. Having found them in all vegetable oils tested, we focused subsequent study on oil palm products. Analysis of the chlorine isotope mass pattern exhibited in high-resolution mass spectrometry enabled organochlorine compound identification in crude palm oils as constituents of wax esters, fatty acid, diacylglycerols, and sphingolipids, which are produced endogenously in oil palm mesocarp throughout ripening. Analysis of thermal decomposition and changes during refining suggested that these naturally present organochlorine compounds in palm oils and perhaps in other vegetable oils are precursors of 3-MCPD esters. Enrichment and dose-response showed a linear relationship to 3-MCPD ester formation and indicated that the sphingolipid-based organochlorine compounds are the most active precursors of 3-MCPD esters

Cyclic Tetrapyrrolic Photosensitisers from the leaves of Phaeanthus ophthalmicus

<p>Abstract</p> <p>Background</p> <p>Twenty-seven extracts from 26 plants were identified as photo-cytotoxic in the course of our bioassay guided screening program for photosensitisers from 128 extracts prepared from 64 terrestrial plants in two different collection sites in Malaysia - Royal Belum Forest Reserve in the State of Perak and Gunung Nuang in the State of Selangor. One of the photo-cytotoxic extracts from the leaves of <it>Phaeanthus ophtalmicus </it>was further investigated.</p> <p>Results</p> <p>The ethanolic extract of the leaves from <it>Phaeanthus ophtalmicus </it>was able to reduce the <it>in vitro </it>viability of leukaemic HL60 cells to < 50% when exposed to 9.6 J/cm²of a broad spectrum light at a concentration of 20 μg/mL. Dereplication of the photo-cytotoxic fractions from <it>P. ophthalmicus </it>extracts based on TLC R_fvalues and HPLC co-injection of reference tetrapyrrolic compounds enabled quick identification of known photosensitisers, pheophorbide-<it>a</it>, pheophorbide-<it>a </it>methyl ester, 13²-hydroxypheophorbide-<it>a </it>methyl ester, pheophytin-<it>a </it>and 15¹-hydroxypurpurin 7-lactone dimethyl ester. In addition, compound <b>1 </b>which was not previously isolated as a natural product was also identified as 7-formyl-15¹-hydroxypurpurin-7-lactone methyl ester using standard spectroscopic techniques.</p> <p>Conclusions</p> <p>Our results suggest that the main photosensitisers in plants are based on the cyclic tetrapyrrole structure and photosensitisers with other structures, if present, are present in very minor amounts or are not as active as those with the cyclic tetrapyrrole structure.</p

Phytochemicals from Kaempferia angustifolia Rosc. and Their Cytotoxic and Antimicrobial Activities

Phytochemical investigation on rhizomes of Kaempferia angustifolia has afforded a new abietene diterpene, kaempfolienol (1) along with crotepoxide (2), boesenboxide (3), 2′-hydroxy-4,4′,6′-trimethoxychalcone (4), zeylenol (5), 6-methylzeylenol (6), (24S)-24-methyl-5α-lanosta-9(11), 25-dien-3β-ol (7), sucrose, β-sitosterol, and its glycoside (8). The structures of the compounds were elucidated on the basis of spectroscopic methods (IR, MS, and NMR). Isolation of 6-methylzeylenol (6), (24S)-24-methyl-5α-lanosta-9(11), 25-dien-3β-ol (7), and β-sitosterol-3-O-β-D-glucopyranoside (8) from this plant species has never been reported previously. The spectroscopic data of (7) is firstly described in this paper. Cytotoxic screening indicated that most of the pure compounds tested showed significant activity with (4) showing the most potent activity against HL-60 (human promyelocytic leukemia) and MCF-7 (human breast cancer) cell lines. However, all extracts and most of the pure compounds tested were found to be inactive against HT-29 (human colon cancer) and HeLa (human cervical cancer) cell lines. Similarly, none of the extracts or compounds showed activity in the antimicrobial testing