ent-Kauranoid Diterpenes from Artemisia sacrorum

Li, Xian; Zhang, Dezhi; Onda, Masayuki; Konda, Yaeko; Iguchi, Mieko; Harigaya, Yoshihiro

doi:10.1021/np50069a018

Cited by 25 publications

(11 citation statements)

References 6 publications

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“…From the aqueous extract of the aerial parts of this plant, two kaurane glycosides, 86 and 87, have been isolated [128], in addition to the kauranetriol 88.…”

Section: R' = R" = Hmentioning

confidence: 99%

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

2007

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This paper presents a review on kaurane diterpenes and their glycoside derivatives, covering aspects of their occurrence, biological activities and the synthesis of these natural products and their analogues. First, it shows and classifies diterpenes, in accordance with the already established structural criteria in the literature. Then, kaurane diterpenes are presented, focusing on their chemical structures, occurrence in the plant kingdom and their main, recently described, biological activities. Moreover, the most significant works, published between 1964 and November 2006, which describe the total synthesis or structural transformations of some kaurane diterpenes, including either semisynthetic and/or microbiological methodologies, are consisely reviewed. At this point, some general considerations on glycosides are introduced, and kaurane glycosides are presented and discussed on the basis of their toxic importance and occurrence in the plant kingdom, having focused on related aspects of their biological activities and the relationships between these activities and the structural factors of their molecules. Finally, the principal methods of glycosidation by enzymatic and chemical processes are both presented, and a few papers on the synthesis of kaurane glycosides are succinctly discussed. Molecules 2007, 12 456

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“…From the aqueous extract of the aerial parts of this plant, two kaurane glycosides, 86 and 87, have been isolated [128], in addition to the kauranetriol 88.…”

Section: R' = R" = Hmentioning

confidence: 99%

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

2007

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“…The relative configuration of the aglycone was assigned by a ROESY experiment. Specifically, the correlations ( Figure 3) between H-C(19)/H-C (20), H-C(20)/ H ax -C (11), H-C(20)/H-C (14), and H ax -C(11)/H-C (14) indicated that these H-atoms were cofacial. The absolute configuration was established by quantum chemical ECD calculation.…”

Section: Introductionmentioning

confidence: 99%

Hispanane‐Type Diterpenoid and Secoiridoid Glucosides from Viburnum cylindricum

Wang

Fang²,

Zhang

et al. 2018

Chemistry & Biodiversity

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Three hitherto unknown compounds, including one new hispanane-type diterpenoid glucoside, namely viburnumoside (1), two new secoiridoid glucosides, 7a-galloyloxysweroside (2), and 7b-galloyloxysweroside (3), together with ten known compounds (4 -13) were isolated from the ethanol extract of twigs and leaves of Viburnum cylindricum. Their structures were elucidated on the basis of extensive spectroscopic studies, and the absolute configuration of compound 1 was confirmed by the experimental and calculated electronic circular dichroism (ECD) data.

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“…The extract was then subjected to normal-phase silica gel column [2 kg, CHCl 3 -MeOH (100 : 0 → 0 : 100, v/v)] to produce eight fractions. Each fraction was subjected to further separation using repeated ODS silica gel, Sephadex LH-20 column chromatography, and HPLC to give smaditerpenic acid A (1, 60 mg), smaditerpenic acid B (2, 80 mg), smaditerpenic acid C (3, 70 mg), smaditerpenic acid D (4, 70 mg), ent-kaurane-3β,16β,17-triol (5, 20 mg), [6] ent-kaurane-16β,17-diol-19-oic acid (6, 100 mg), [7] ent-kaurane-16β,17,18-triol (7, 30 mg), [8] 1-pentacosanol (8, 80 mg), [9] and 1-octacosanol (9, 52 mg). [9] Smaditerpenic acid A (1) …”

Section: Extraction and Isolationmentioning

confidence: 99%

Structure elucidation and complete NMR spectral assignments of four new diterpenoids from Smallantus sonchifolius

Dou

Tian

Qiu

et al. 2008

Magnetic Reson in Chemistry

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Four new diterpenoids, named smaditerpenic acid A-D, together with five known compounds, were isolated from the H(2)O extract of the leaves of Smallantus sonchifolius (yacon) cultivated in Liaoning, China and their structures were elucidated on the basis of one- and two-dimensional NMR (including (1)H, (13)C-NMR, (1)H-(1)H COSY, HSQC, TOCSY, HMBC, and ROESY), electrospray ionization mass spectrometry (ESI-MS), and chemical methods.

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ent-Kauranoid Diterpenes from Artemisia sacrorum

Abstract: A new ent-kauranoid diterpene diglycoside has been isolated from Artemisia sacrorum along with two known ent-kauranoid diterpenes. Their structures are elucidated by means of nmr analysis (DEPT, 1H-1H COSY, 1H-13C COSY, and 1H-1H decoupling).

Cited by 25 publications

References 6 publications

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

Hispanane‐Type Diterpenoid and Secoiridoid Glucosides from Viburnum cylindricum

Structure elucidation and complete NMR spectral assignments of four new diterpenoids from Smallantus sonchifolius

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