Pinoresinol and syringaresinol: two lignans from Avicennia germinans (Avicenniaceae)

Sharp, Hazel; Thomas, David M.; Currie, Felicity; Bright, Colin; Latif, Zahid; Sarker, Satyajit D.; Nash, Robert J.

doi:10.1016/s0305-1978(00)00050-8

Cited by 15 publications

(10 citation statements)

References 15 publications

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“…The 1 H-1 H COSY spectrum of 1 showed co-relation of H-7 with H-2, H-6 and H-8. The 1 H and 13 C NMR values were compared with lignans (Cowan et al, 2001;Goulart et al, 1995;Joshi et al, 1998;Li et al, 2005;Perez et al, 1995;Shahat et al, 2004;Sharp et al, 2001). On the basis of the foregoing account, the structure of 1 has been established as (7,8,2 0 )-3,4,5-trimethoxy-7,3 0 ,1 0 ,9 0 -diepoxylignan.…”

Section: Resultsmentioning

confidence: 99%

“…The 13 C NMR spectrum of 3 exhibited aromatic carbon signals between 108.76 and 158.5, oxygenated methylene at 106.89 (OCH 2 -O), oxygenated methylene signals at 68.98 (C-9) and 69.25 (C-9 0 ), carbinol signals at 85.61 (C-7) and 84.69 (C-7 0 ) and methoxy signals at 61.83 and 60.75. The 13 C NMR values of 3 were compared with that of demethylpiperitol (Perez et al, 1995) and other lignans (Cowan et al, 2001;Goulart et al, 1995;Joshi et al, 1998;Li et al, 2005;Perez et al, 1995;Shahat et al, 2004;Sharp et al, 2001). On the basis of these evidences the structure of 3 has been elucidated as (7,7 0 ,8,8 0 )-3,4-dioxymethylene-3 0 ,4 0 -dimethoxy-7,9 0 ,7 0 ,9-diepoxylignan-5 0 -ol.…”

Section: Resultsmentioning

confidence: 99%

“…The 13 C NMR spectrum of 9 showed signals for lactone carbon at 171.34 (C-9), aromatic carbons between 159.17 and 107.17, oxygenated methine carbons at 84.35 (C-7) and 84.89 (C-7 0 ), oxygenated methylene carbons at 69.79 (C-9 0 ) and methine carbons at 57.61 (C-8) and 57.08 (C-8 0 ). The 1 H and 13 C NMR values were compared with the lignan molecules (Bhatia & Bajaj, 1975;Cowan et al, 2001;Li et al, 2005;Sengupta & Das, 1965;Sharp et al, 2001). On the basis of above discussion Natural Product Research 425 the structure of 9 is (7,7 0 ,8,8 0 )-9-oxo-7,9 0 ,7 0 ,9-diepoxylignan-3,4,3 0 ,4 0 ,5 0 -pentaol or 3,3 0 -didemethyl-9-oxo-pinoresinol.…”

Section: Resultsmentioning

confidence: 99%

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Lignan derivatives from the stem bark ofSyzygium cumini(L.) Skeels

Mir

Ali²,

Alam

2009

Natural Product Research

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Phytochemical investigation of the stem bark of Syzygium cumini (L.) Skeels (Myrtaceae) yielded four new lignan derivatives characterised as (7alpha,8alpha,2'alpha)-3,4,5-trimethoxy-7,3',1',9'-diepoxylignan (cuminiresinol), (7alpha,7'alpha,8alpha,8'alpha)-3,4-dioxymethylene-3',4'-dimethoxy-7,9',7',9-diepoxylignan-5'-ol (5'-hydroxy-methyl-piperitol), (7alpha,7'alpha,8alpha,8'alpha)-3'-methoxy-9-oxo-7,9',7',9-diepoxylignan-3,4,4'-triol or 3-demethyl-9-oxo-pinoresinol (syzygiresinol A), (7alpha,7'alpha,8alpha,8'alpha)-9-oxo-7,9',7',9-diepoxylignan-3,4,3',4',5'-pentaol or 3,3'-didemethyl-9-oxo-pinoresinol (syzygiresinol B) along with the known lignans di-demethyl-5-hydroxypinoresinol, dimethylpinoresinol, didemethoxypinoresinol, pinoresinol and 4'-methyl-5'-hydroxypinoresinol. The structures of these lignans were elucidated on the basis of structural data analysis and chemical reactions.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Lignan derivatives from the stem bark ofSyzygium cumini(L.) Skeels

Mir

Ali²,

Alam

2009

Natural Product Research

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“…Their anti‐inflammation effect was further evaluated on same model, and the results indicated that two subfractions were responsible anti‐inflammation effect mainly. After then, 25 compounds, orthosiphol M ( 1 ), (Awale et al., 2001) orthosiphonone A ( 2 ), (Shibuya et al, 1999a) orthosiphol N ( 3 ), (Awale et al., 2001), orthosiphol A ( 4 ), (Masuda et al, 1992a) orthosiphol B ( 5 ), (Masuda et al, 1992b) neoorthosiphol A ( 6 ), (Shibuya et al, 1999a) orthosiphol D ( 7 ), (Takeda et al., 1993) orthosiphonone D ( 8 ), (Nguyen et al., 2004) spicatusene B ( 9 ), (Luo et al., 2018) spicatusene C ( 10 ), (Luo et al., 2018) orthosiphol K ( 11 ), (Awale et al., 2001) orthosiphol L ( 12 ), (Awale et al., 2001) norstaminol B ( 13 ), (Stampoulis et al., 1999) 2‐ o ‐deacetylorthosiphol J ( 14 ), (Awale,et al., 2003) orthosiphol E ( 15 ), (Takeda et al., 1993) neoorthosiphol B ( 16 ), (Shibuya et al, 1999b) fragransin B1 ( 17 ), (Miyachi et al., 1987) syringaresinol ( 18 ), (Sharp et al., 2001) asperglaucidev ( 19 ), (Ishiguro et al., 1991) salvigenin ( 20 ), (Miana et al., 1985) sinensetin ( 21 ), (Akowuah et al., 2004) 5,6,7,4′‐tetramethoxyflavone ( 22 ), (Lee et al., 2008) eupatorin ( 23 ), (Ramaraj et al., 2018) 5,6,7,3′,4′‐pentamethoxyflavanone ( 24 ), (Iwase et al., 2001) and caffeic acid methyl ester ( 25 ) (Starkov et al., 1975) were isolated from the two bioactive subfractions. Further pharmacological investigation on pure compounds indicated that most of the isolates remarkably inhibited productions of inflammatory mediators (IL‐8, IL‐1 β , and TNF‐ α ) in LPS‐induced HK ‐2 cells, and compounds 1 , 2 , 5 – 7 , 17 , 21, and 22 showed significantly anti‐inflammatory on xylene‐induced acute inflammatory mice model.…”

Section: Introductionmentioning

confidence: 99%

Bioassay‐guided isolation of anti‐inflammatory diterpenoids with highly oxygenated substituents from kidney tea ( Clerodendranthus spicatus )

et al. 2020

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The whole plant of Clerodendranthus spicatus (Thunb.) is one of popular functional food in south of China, named as "kidney tea" and used to ameliorate renal inflammation. In order to verify this potential function and explore the accurate compounds responsible for inflammation, the ethanol extract, fractions, and subfractions of this plant were prepared to evaluate anti-inflammation effect on xylene-induced acute inflammatory mice model, and the results indicated that two subfractions from EtOAc fraction show potential activities. Subsequent bioassay-guided isolation of the bioactive subfractions led to isolation of 25 compounds. Among them, compounds 2, 4, 5, 9-11, 13, 16, 17, and 20-22 inhibited the productions of pro-inflammation factors TNF-α, IL-1β, and IL-8 in lipopolysaccharide (LPS)-induced renal epithelia (HK-2) cells, respectively. Further anti-inflammation evaluation in vivo indicated that the major bioactive compounds 1, 2, 5-7, 17, 21, and 22 from C. spicatus were even better than aspirin. Practical applications C. spicatus as a healthy tea has been available in the Chinese market and as a medicine for various disorders such as nephritis, rheumatism, inflammation, gout, and diabetes. Previous pharmacological investigation of the plant revealed the potential antiinflammatory activities, but the material basis of anti-inflammatory activity remains to be elucidated. In our study, the anti-inflammatory fractions and compounds were obtained by the bioassay-guide isolation and the results showed that the highly oxygenated diterpenoids were major anti-inflammatory compounds, in which 1, 2, 5-7, 17, 21, and 22 were even better than aspirin. This information supported kidney tea as a functional food for treatment of renal inflammation reasonably and may add a new dimension to biological activity of this plant in the field of agriculture as a functional food were cultivated.

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“…Members of this family have adapted to the high salt levels in the mangrove habitat by secreting salt from specialized glands in their leaves (Sobrado & Greaves 2000). Previous phytochemical and chemotaxonomic investigations within the genus have resulted in the isolation of iridoid glucoside (Ko¨nig et al 1987), lignan (Sharp et al 2001), phenylpropanoid (Fauvel et al 1993), and triterpenoid (Subramanian & Vedantham 1974) constituents. Itoigawa et al (2001) reported antitumour promoter activity for naphthoquinones and their analogues obtained from Avicennia alba and Avicennia rumphiana, and Sharaf et al (2000) described the isolation and identification of moderately cytotoxic flavonoids from the aerial parts of Avicennia marina.…”

Section: Introductionmentioning

confidence: 99%

Antitumour activity of 3-chlorodeoxylapachol, a naphthoquinone from Avicennia germinans collected from an experimental plot in southern Florida

Jones

Lobo-Echeverri

et al. 2005

Journal of Pharmacy and Pharmacology

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As part of an ongoing collaborative effort to discover new anticancer agents from plants, an extract obtained from the leaves and twigs of Avicennia germinans, collected in a coastal area of southern Florida, was identified as possessing cytotoxic activity in a panel of human cancer cell lines. Fractionation of the petroleum ether partition, using cytotoxicity to guide the fractionation, led to the isolation of 3-chlorodeoxylapachol. The antitumour potential of 3-chlorodeoxylapachol was demonstrated with the in-vivo hollow fibre assay, a model of antitumour activity using human cancer cell-filled fibres implanted into mice. The possibility that this compound is an artefact of the isolation procedure was ruled out by liquid chromatography-mass spectrometry analysis of extracts prepared without the use of chlorinated solvent. In conclusion, 3-chlordeoxylapachol, a secondary metabolite obtained from the chloroform-soluble extract of a mangrove tree, was cytotoxic in a panel of human cancer cells, and active against KB human cancer cells in the murine hollow fibre antitumour model, with selectivity in KB cells for the intravenous site at lower doses, indicating possible metabolic activation.

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Pinoresinol and syringaresinol: two lignans from Avicennia germinans (Avicenniaceae)

Cited by 15 publications

References 15 publications

Lignan derivatives from the stem bark ofSyzygium cumini(L.) Skeels

Lignan derivatives from the stem bark ofSyzygium cumini(L.) Skeels

Bioassay‐guided isolation of anti‐inflammatory diterpenoids with highly oxygenated substituents from kidney tea ( Clerodendranthus spicatus )

Antitumour activity of 3-chlorodeoxylapachol, a naphthoquinone from Avicennia germinans collected from an experimental plot in southern Florida

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