A diterpenoid sulphate and flavonoids from wedelia asperrima

Calanasan, Cleofe A.; MacLeod, John K.

doi:10.1016/s0031-9422(98)80079-4

Cited by 19 publications

(6 citation statements)

References 12 publications

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“…Farag et al (1997) identified the anthochlors coreopsin, stillopsin, and sulfurein from extracts of W. prostrata. A recent study of W. asperrima, a toxic herb native to northern Australia, resulted in the identification of a new flavanone, 7,4'-dihydroxy-8,3'-dimethoxyflavanone, the corresponding chalcone, and its 4'-0-glucoside (Calanasan and MacLeod, 1998). (The toxic components of the plant are kaurene aminoglycosides.)…”

Section: Chjo~mentioning

confidence: 99%

Flavonoids of the Sunflower Family (Asteraceae)

Bohm

Stuessy

2001

120

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This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machines or similar means, and storage in data banks. This book is dedicated to:Arthur Cronquist Outstanding plant systematist and major contributor to understanding taxonomic relationships within Asteraceae and Ralph E. Alston (1925Alston ( -1967) Visionary natural products chemist and geneticist who pioneered the use of chemical data in studies of plant systematics and evolution PrefaceCertainly many of the readers of this book will remember the early developments of chemosystematics in the late 1950s. We ourselves remember the excitement of these new data bearing on plant interrelationships. The hopes were high, the techniques were rapidly evolving, the quantities of data were large, and young workers were eagerly enthusiastic. Some even went so far as to predict that chemical data would soon replace morphological information as the basis for plant classification. These overly zealous predictions did not materialize, of course, as the history of plant systematics has amply shown during the past two centuries. If there is any distinct characteristic of systematics it is synthesis, as Lincoln Constance (1964) called it, the "unending synthesis." New tools generate new data and provide insights on additional dimensions of plant relationships. This will never change-we will continue to discover new tools and new data in the years ahead, and they will continue to be incorporated into the predictive general reference system of classification.The earlier efforts in chemosystematics focused on secondary plant products: alkaloids, betacyanins, carbohydrates, cyanogenic glycosides, glucosinolates, lipids, terpenoids, and especialiy flavonoids. The latter were particularly well suited for chemosystematic investigation for several reasons: ease of isolation and characterization, small amounts of plant material needed for analysis, stability of compounds especially through routine preparation of herbarium specimens, and low cost to obtain useful information. As a result of these considerable advantages, literally thousands of studies on use of flavonoids in plant systematics have been published. Although now with the present zest for macromolecular data from DNA restriction sites and sequences, there are fewer workers and laboratories dedicated to flavonoid chemosystematic studies; twenty years ago they were the new currency of exciting data in plant systematics.Because of many workers historically interested in the sunflower family, Asteraceae (or Compositae), in part due to its large size (approximately 23,000 species;Bremer, 1994), and because hundreds of flavonoid compounds were discovered in this family, many chemosystematic investigations have been completed on various taxa. Many studies came from the laboratories of R. A. Alston, B. L. Turner, and T. J. Mabry in the Department of Botany ...

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Section: Chjo~mentioning

confidence: 99%

Flavonoids of the Sunflower Family (Asteraceae)

Bohm

Stuessy

2001

120

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“…Since HÀC(5) was supposed to be b-oriented [6], HÀC(1) should be a-oriented from the coupling constant between HÀC(1) and HÀC(5) (J ¼ 15.3 Hz). The ROESY cross-peaks HÀC(1)/HÀC(9) and H trans ÀC(14) (trans to C(9))/Me (15) indicated that HÀC(9) was a-oriented, while Me(15) was boriented (Fig. 2).…”

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confidence: 99%

A Guaianolide Sesquiterpene, a Chromenone, and a Flavanone from Ligularia macrophylla

Wang

Chen

2007

Helvetica Chimica Acta

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Three new compounds, (5b,9b)-guaia-6,10(14)-dien-9-ol (¼ rel-(1R,3aS,5R,8aR)-1,2,3,3a,4,5,6,8a-octahydro-1-methyl-4-methylene-7-(1-methylethyl)azulen-5-ol; 1), 6-acetyl-8-methoxy-2,3-dimethylchromen-4-one (¼ 6-acetyl-8-methoxy-2,3-dimethyl-4H-1-benzopyran-4-one; 2), and (2S)-3'-hydroxy-5',7-dimethoxyflavanone (¼ (2S)-2,3-dihydro-2-(3-hydroxy-5-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one; 3) were isolated from the roots and rhizomes of Ligularia macrophylla, together with seven known compounds. Their structures and configurations were elucidated by spectroscopic methods, including 2D-NMR techniques.Introduction. -Much attention has been focused on the Ligularia (Asteraceae) plants for the long history of use as folk remedies and the abundant sesquiterpenes distributed in this genus. The roots and rhizomes of Ligularia macrophylla (Ledeb.) DC. are used as a Chinese folk medicine for the treatment of tracheitis, phthisis, hemoptysis, cough, and asthma [1]. In the previous reports, fatty acids, polyenes, pyrrolizidine alkaloids, and eremophilane sesquiterpenes have been isolated [2 -4]. Our preliminary study showed that the AcOEt-soluble fraction from an EtOH extract of the roots and rhizomes of L. macrophylla, a plant growing in the Tianshan mountains of China, exhibited cytotoxic activity against human breast adenocarcinoma cells (MCF-7) in vitro. This prompted us to investigate its chemical constituents. The phytochemical study led to the isolation and characterization of three new compounds 1 -3, together with seven known ones; however, no isolate showed cytotoxicity (EC 50 > 20 mg/ml). This paper deals with the isolation and structural elucidation of the three new compounds 1 -3.

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“…C o m p a r i s o n s w i t h l i t e r a t u r e i d e n t i f i e d 1 a s isoliquiritigenin (Ma et al 2005), 3 as 7,3′,4′trihydroxyflavone (Vieira Júnior et al 2008), 5 as (−)butin (Vieira Júnior et al 2008), and 6 as homobutein (Ji et al 2016;Calanasan and MacLeod 1998). The NMR data of each compound can be found in experimental part; 1 H and 13 C NMR spectra are presented in support information.…”

Section: Resultsmentioning

confidence: 99%

Flavonoids, Cytotoxic, and Antimalarial Activities of Dipteryx lacunifera

Alexandre

Oliveira

Dittz

et al. 2020

Rev. Bras. Farmacogn.

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Dipteryx lacunifera Ducke, Fabaceae, popularly known as "fava-de-morcego" and "garampara," comprises pleasant tasting kernels and is commonly consumed by inhabitants northeast of Brazil. In the present study, among six flavonoids, two are reported for the first time as natural products, 6,3′,4′-trihydroxyflavone (2) and 4-O-metilsulfuretin (4); two reported for the first time in the species isoliquiritigenin (1) and homobutein (6); and two already known flavonoids, 7,3′,4′-trihydroxyflavone (3) and (−)-butin (5), were isolated from fruits and kernels of D. lacunifera. The compounds were isolated by chromatographic techniques and elucidated by spectrometric data (1D and 2D NMR and mass). Compounds 1-3 and 5 showed interesting cytotoxicity against tumor cell lines with inhibitory concentration (IC 50) values ranging from 21.13 to 2.47 μg/ml. In addition, compounds 1 and 2 showed antimalarial activity against P. falciparum with 81.25 and 88.98% of parasitemia reduction, respectively.

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A diterpenoid sulphate and flavonoids from wedelia asperrima

Cited by 19 publications

References 12 publications

Flavonoids of the Sunflower Family (Asteraceae)

Flavonoids of the Sunflower Family (Asteraceae)

A Guaianolide Sesquiterpene, a Chromenone, and a Flavanone from Ligularia macrophylla

Flavonoids, Cytotoxic, and Antimalarial Activities of Dipteryx lacunifera

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