| 1. |
- Abdissa, Negera, et al.
(författare)
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Naphthalene Derivatives from the Roots of Pentas parvifolia and Pentas bussei
- 2016
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Ingår i: Journal of natural products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 79:9, s. 2181-2187
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Tidskriftsartikel (refereegranskat)abstract
- The phytochemical investigation of the CH2Cl2/MeOH (1:1) extract of the roots of Pentas parvifolia led to the isolation of three new naphthalenes, parvinaphthols A (1), B (2), and C (3), two known anthraquinones, and five known naphthalene derivatives. Similar investigation of the roots of Pentas bussei afforded a new polycyclic naphthalene, busseihydroquinone E (4), a new 2,2′-binaphthralenyl-1,1′-dione, busseihydroquinone F (5), and five known naphthalenes. All purified metabolites were characterized by NMR and MS data analyses, whereas the absolute configurations of 3 and 4 were determined by single-crystal X-ray diffraction studies. The E-geometry of compound 5 was supported by DFT-based chemical shift calculations. Compounds 2-4 showed marginal cytotoxicity against the MDA-MB-231 human triple-negative breast cancer cell line with IC50 values ranging from 62.3 to 129.6 μM. © 2016 The American Chemical Society and American Society of Pharmacognosy.
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| 2. |
- Appendino, Giovanni, et al.
(författare)
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A meroterpenoid NF-kappa B inhibitor and drimane sesquiterpenoids from asafetida
- 2006
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 69:7, s. 1101-1104
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Tidskriftsartikel (refereegranskat)abstract
- Investigation of an acetone extract from asafetida afforded two drimane sesquiterpene dienones (fetidones A and B, 1a,b) and several known sesquiterpene coumarin ethers, one of which (8-acetoxy-5-hydroxyumbelliprenin, 2a) showed potent and specific NF-kappa B-inhibiting properties. This, coupled to a negligible cytotoxicity, qualifies 2a as a new anti-inflammatory chemotype, and its occurrence in asafetida might rationalize the use of this gum resin to alleviate and prevent colon inflammatory disturbances.
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| 3. |
- Appendino, G, et al.
(författare)
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A new P-glycoprotein inhibitor from the caper spurge (Euphorbia lathyris).
- 2003
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 66:1, s. 140-142
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Tidskriftsartikel (refereegranskat)abstract
- The macrocyclic lathyrane polyester Euphorbia factor L10 (1a) has been obtained from the seeds of the caper spurge (E. lathyris). The interaction of L10 (1a) and its acetyl derivative (1b) with P-glycoprotein, a multidrug transporter overexpressed in cancer cells and responsible for resistance to chemotherapy, was investigated. The results established lathyrane diterpenoids as a novel chemotype for P-glycoprotein inhibitors.
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| 4. |
- Appendino, G, et al.
(författare)
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Antibacterial galloylated alkylphloroglucinol glucosides from myrtle (Myrtus communis)
- 2006
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 69:2, s. 251-254
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Tidskriftsartikel (refereegranskat)abstract
- An investigation of the polar glycosidic fraction from the leaves of myrtle afforded four galloylated nonprenylated phloroglucinol glucosides (3a-d) related to the endoperoxide hormone G3 (4) in terms of structure and biogenesis. Despite their close similarity, significant antibacterial activity was shown only by one of these compounds (3b, gallomyrtucommulone B), while the G3 hormone (4) was inactive.
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| 5. |
- Appendino, Giovanni, et al.
(författare)
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Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-pyrone from Helichrysum italicum ssp microphyllum
- 2007
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 70:4, s. 608-612
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Tidskriftsartikel (refereegranskat)abstract
- An acetone extract of Helichrysum italicum ssp. microphyllum afforded the phloroglucinol alpha-pyrone arzanol (1a) as a potent NF-kappa B inhibitor. Arzanol is identical with homoarenol (2a), whose structure should be revised. The phloroglucinol-type structure of arzanol and the 1,2,4-trihydroxyphenyl-type structure of the base-induced fragmentation product of homoarenol could be reconciled in light of a retro-Fries-type fragmentation that triggers a change of the hydroxylation pattern of the aromatic moiety. On the basis of these findings, the structure of arenol, the major constituent of the clinically useful antibiotic arenarin, should be revised from 2b to 1b, solving a long-standing puzzle over its biogenetic derivation. An alpha-pyrone (micropyrone, 7), the monoterpene rac-E-omega-oleoyloxylinalol (10), four known tremetones (9a-d), and the dimeric pyrone helipyrone (8) were also obtained. Arzanol inhibited HIV-1 replication in T cells and the release of pro-inflammatory cytokines in LPS-stimulated primary monocytes, qualifying as a novel plant-derived anti-inflammatory and antiviral chemotype worth further investigation.
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| 6. |
- Appendino, G, et al.
(författare)
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Oligomeric acylphloroglucinols from myrtle (Myrtus communis)
- 2002
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 65:3, s. 334-338
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Tidskriftsartikel (refereegranskat)abstract
- The dimeric nonprenylated acylphloroglucinol semimyrtucommulone (6) was obtained from the leaves of. myrtle (Myrtus communis) as a 2:1 mixture of two rotamers. The known trimeric phloroglucinol myrtucommulone A (1) was also isolated and characterized spectroscopically as a silylated cyclized derivative (5). Myrtucommulone A showed significant antibacterial activity against multidrug-resistant (MDR) clinically relevant bacteria, while semimyrtucommulone was less active.
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| 7. |
- Appendino, G, et al.
(författare)
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SERCA-inhibiting activity of C-19 terpenolides from Thapsia garganica and their possible biogenesis
- 2005
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 68:8, s. 1213-1217
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Tidskriftsartikel (refereegranskat)abstract
- An investigation of Thapsia garganica afforded a series of tetracyclic C-19 dilactones, whose production was dependent on the time and location of the collection. These unusual tetrahomosesquiterpenoids are presumably biosynthesized via a carbon dioxide-triggered electrophilic polyolefin cyclization. Despite the structural differences with thapsigargin, these compounds showed SERCA-inhibiting properties.
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| 8. |
- Appendino, G, et al.
(författare)
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Structure-activity relationships of ring C-secotaxoids. 1. Acylative modifications
- 2004
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 67:2, s. 184-188
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Tidskriftsartikel (refereegranskat)abstract
- The acylative modification of IDN 5390 (3a), a 7,8-secotaxoid under preclinical development, was investigated. A modest decrease of potency was observed upon acylation of the primary and the enolic hydroxyls, suggesting that, just like in paclitaxel, the hydroxyl groups in the upper right-hand sector are not critical for cytotoxicity. The activity of these analogues, and especially of the chemically robust carbonates 3c and 3d, makes it unlikely that the activity of IDN 5390 is due to in vivo oxidation to a fledgling 7-aldehyde and re-aldolization to the corresponding taxane derivative.
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| 9. |
- Appendino, G, et al.
(författare)
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Structure-activity relationships of the estrogenic sesquiterpene ester ferutinin. Modification of the terpenoid core
- 2004
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 67:9, s. 1557-1564
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Tidskriftsartikel (refereegranskat)abstract
- Esterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the a-face of the molecule proved detrimental. Taken together, these observations identified the substitution at C-8/C-9 as critical for activity.
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| 10. |
- Atilaw, Yoseph, et al.
(författare)
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Prenylated Flavonoids from the Roots of Tephrosia rhodesica
- 2020
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 83:8, s. 2390-2398
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Tidskriftsartikel (refereegranskat)abstract
- Five new compounds-rhodimer (1), rhodiflavan A (2), rhodiflavan B (3), rhodiflavan C (4), and rhodacarpin (5)-along with 16 known secondary metabolites, were isolated from the CH2Cl2-CH3OH (1:1) extract of the roots of Tephrosia rhodesica. They were identified by NMR spectroscopic, mass spectrometric, X-ray crystallographic, and ECD spectroscopic analyses. The crude extract and the isolated compounds 2-5, 9, 15, and 21 showed activity (100% at 10 mu g and IC50 = 5-15 mu M) against the chloroquine-sensitive (3D7) strain of Plasmodium falciparum.
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