Tortuoside, A New Natural Coumarin Glucoside from Seselitortuosum

Ceccherelli, Paolo; Curini, Massimo; Marcotullio, Maria Carla; Madruzza, Gian Federico; Menghini, Alessandro

doi:10.1021/np50064a042

Cited by 12 publications

(6 citation statements)

References 4 publications

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“…(1), ( -)-(/?,£)-murrangatin [9] (5,6), and imperatorin [12} (7) were identified by direct comparison with samples isolated previously in our laboratories. Five others, (E)-dehydroosthol [5] (5), (Z)-dehydroosthol [6] (5), (J)-meranzin hydrate [8} (5,8), ( -)-(£,R)-murrangatin-2'-acetate [10} (1,5,6), and luvangetin [18} (9) gave spectral data in accord with those published in the literature. Three further coumarins isolated from the petroleum ether extract appear to be novel.…”

supporting

confidence: 74%

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Coumarins from Phebalium tuberculosum ssp. megaphyllum and Phebalium filifolium

Rashid¹,

Gray²,

Waterman³

et al. 1992

J. Nat. Prod.

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A total of 14 coumarins have been isolated from the aerial parts of Phebalium tuberculosum ssp. megaphyllum and 9 from Phebalium filifolium (Rutaceae). Three of the coumarins obtained from P. tuberculosum ssp. megaphyllum are novel and have been characterized, on the basis of spectroscopic analysis, as (E)-7-(6-hydroperoxy-3,7-dimethylocta-2,7- dienyloxy)coumarin [3], (E)-8-(6-hydroperoxy-3,7-dimethylocta-2,7-dienyloxy)psoralen [16] and (E,E)-8-(7-hydroxy-3,7-dimethylocta-2,5-dienyloxy)psoralen [15] In addition, both species yielded the simple acetophenone xanthoxylin, and P. tuberculosum ssp. megaphyllum gave (E)-betulin-3-p-coumarate [20] and (Z)-betulin-3-p-coumarate [21], both of which appear to be novel. The chemotaxonomic implications of coumarin distribution in the two species are discussed.

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supporting

confidence: 74%

“…Meranztn hydrate [8].-Gum: mlz 278.1172 (caled for C15H1805 278.1154); [ce]D-25°(r= 0.3, CHC13). Uv, ir, 'H nmr, eims, and optical rotation in agreement with literature (5,8).…”

Section: Extraction and Isolationmentioning

confidence: 99%

Coumarins from Phebalium tuberculosum ssp. megaphyllum and Phebalium filifolium

Rashid¹,

Gray²,

Waterman³

et al. 1992

J. Nat. Prod.

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“…The HR-ESI-MS of 6 showed a quasimolecular ion at m/z 505.1692, which, in conjunction with the 13 27.06 (c 0.5, CH 3 OH)) with (−)-meranzin hydrate. 32,33 Thus, 6 was identified as (12R)-13-O-β-Dglucosylmeranzin hydrate and named as meranzin hydrate III.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The HMBC correlations of H-6′ (δ H 4.21 (1H, dd, J = 11.6, 2.2 Hz, 6′-Ha)/4.00 (1H, dd, J = 11.6, 8.1 Hz, 6′-Hb)) with CH 3 C O– (δ C 170.1), and H-1′ (δ H 4.43 (1H, d, J = 7.8 Hz)) with C-13 (δ C 80.1) located the acetyl unit at C-6′ of the glucosyl moiety and the sugar unit at C-13 of the aglycone, respectively. The R configuration of C-12 was determined by acid hydrolysis and comparison of the aglycone optical rotation value ([α] D 29 27.06 ( c 0.5, CH 3 OH)) with (−)-meranzin hydrate. , Thus, 6 was identified as (12 R )-13- O -β- d -glucosylmeranzin hydrate and named as meranzin hydrate III.…”

Section: Resultsmentioning

confidence: 99%

Coumarin Analogues from the Citrus grandis (L.) Osbeck and Their Hepatoprotective Activity

Tian

Wang

Duan

et al. 2019

J. Agric. Food Chem.

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Seven new coumarin analogues (1, 2, and 4−8), together with ten known analogues (3, 9−17), were isolated from the air-dried pericarp of Citrus grandis. The structures of these compounds were determined by HR-ESI-MS, UV/vis, and 1D-and 2D-NMR spectra. Meanwhile, the hepatoprotective activities of all these coumarins were evaluated by MTT assays using the D-galactosamine-induced LO2 cell injury model. The results show that compounds 3 and 4 exhibited the strongest hepatoprotective activities. Moreover, compounds 3 and 4 suppressed increases in the levels of alanine transaminase (ALT) and aspartate transaminase (AST) in D-galactosamine-treated LO2 cells, further confirming the hepatoprotective effects of these compounds. Mechanistically, compounds 3 and 4 increased the activities of antioxidant enzymes such as superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) and decreased the level of malondialdehyde (MDA) in injured LO2 cells induced by D-galactosamine. These findings shed light on a better understanding of the hepatoprotective effect of Citrus grandis, providing novel insights into the development of coumarin-based hepatoprotective drugs in the future.

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“…90 The absolute stereochemistry of tortuoside (85), from Seseli tortuosum, was determined as 2'R by comparing the optical rotation of the methyl ether of its hydrolysis product with that of natural meranzin hydrate (86). 91 Three structurally related 7-prenyloxycoumarins have been isolated from leaves of Cfausena anisata, anisocoumarin E (87), F (88), and G (89),31 and two others, ( 90) and ( 91), from Eriostemon spicatus aerial parts.92 It is possible that 3"dehydroxy-3-chlorotriphasiol (92) is an artifact since chloroform was used for its extraction from Triphasia t r i f ~l i a . ~~ Similarly, a leaf constituent (93) of Murraya exotica may also be an artifact.94 Yuehgesin-A (94), -B (99, and -C (96) have been isolated from fresh flowers of M .…”

Section: C-substituted 7-oxygenated Coumarinsmentioning

confidence: 99%