A phenylstyrene from Hintonia latiflora

Mata, Rachel; Camacho, Maria del Rayo; Mendoza, Sandra; Cruz, María del Carmen

doi:10.1016/0031-9422(92)83474-d

Cited by 22 publications

(26 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…299 Another compound with an (hydroxyphenyl)vinyl group linked to the phloroglucinol moiety, 408, has been reported from the stem bark of Hintonia latiflora. 188 For the structures of compounds 393-408, see Fig. 12.…”

Section: Miscellaneous Monomeric Phloroglucinolsmentioning

confidence: 99%

Phloroglucinol compounds of natural origin

2006

View full text Add to dashboard Cite

Section: Miscellaneous Monomeric Phloroglucinolsmentioning

confidence: 99%

Phloroglucinol compounds of natural origin

2006

View full text Add to dashboard Cite

“…The residue was subjected to column chromatography (silica, EtOAc-Et 2 O-CH 2 Cl 2 , 1:1:1) to obtain the crude product, which was recrystallized from CH 2 Cl 2 -hexane to afford 1 (0.6 g, 76%) as a pale yellow solid; mp 214-216°C (lit. 23…”

Section: 7-dihydroxy-4-(34-dihydroxyphenyl)-chromen-2-one (1)mentioning

confidence: 99%

An Efficient Synthesis of Neoflavonoid Antioxidants Based on Montmorillonite K-10 Catalysis

Lee¹,

Tseng²,

Lee³

2001

Synthesis

View full text Add to dashboard Cite

A new approach to synthesis of neoflavonoids, based on a high yielding Montmorillonite K-10 catalyzed lactone ring forming cyclization process, is described. The utility of this methodology is exemplified by its employment in the preparation of the substituted 4-phenylneoflavonoids 1-8. The free radical scavenging properties of these substances were evaluated. The neoflavonoids 1 and 5, which mimic esculetin-type antioxidants, were observed to quench hydrazyl free radicals.As part of a recent search 1 to prepare new biologically active substances, we were attracted to the coumarin family whose members are widely distributed in biologically important natural products and pharmaceutical agents. 2 Coumarins exist in free or glycoside-conjugated forms in a wide variety of plants. 3 Indirect analgesic effects (abolition of oedema and inflammation) of coumarin in rabbit have been observed. 4 Coumarin and 7-hydroxycoumarin also inhibit the biosynthesis of prostaglandins and leucotrienes to about the same degree as acetylsalicylic acid. 5 Moreover, this substance has anti-oedematous, lymphokinetic and haemorheological properties. 6 Naturally occurring neoflavonoid glycosides are known to serve as inhibitors of energy transfer in spinach chloroplasts. 7 Inspite of these effects, Zobel and Brown 8 have concluded that the biologcal roles of coumarins are not well understood.In our previous studies, we have demonstrated that esculetin (6,7-dihydroxycoumarin) possesses potent antioxidant and antitumor promotion properties. 9 The data indicate that this compound induces apoptosis in human leukemia cells by increasing cytosolic translocation of cytochrome c and activating the cysteine protease 32 kDa proenzyme (CPP32). 4-Phenylcoumarins are also of synthetic interest owing to the fact that this ring system is present in a number of naturally occurring compounds, such as serratin, 10a dalbergin, 10b-10d calophyllolide, 10e calomelanols B and C 11 and vismiaguianones D and E. 3dAs a consequence of the biological and structural interest in these substances, we initiated a study aimed at developing a general and high yielding method to prepare coumarins. The commercial availability of cinnamic acids and phloroglucinol prompted us to probe a route to the neoflavonoids, which is based on an esterification-cyclization sequence. It is known that regioselective esterification of the a,b-unsaturated carboxylic acids with polyphenols often is problematic due to competition between cyclization by Friedel-Crafts acylation and Fries rearrangement of the initially formed ester intermediate. 12 Although the synthesis of some coumarins has been successfully approached by using this strategy, 13 harsh condition and high substrate concentrations are commonly required. In addition, Shamsuddin has reported a one-pot procedure for the synthesis of 4-phenylcoumarins. 14 However, the scope of this process appears to be limited. For instance, by following Shamsuddin's procedure, we were unable to efficiently prepare 5,7-dihydroxy-4-phenylcoumarin f...

show abstract

“…H. standleyana, known in Mexico with the vernacular names of ªcopalchiº and ªquina amarillaº, among others, is also used to treat malaria and fevers [19]. To the best of our knowledge this species has not been investigated, however, several phytochemical studies carried out on the related species H. latiflora, E. caribeaum and E. mexicanum Gray resulted in the isolation and identification of several cucurbitacins, 4-phenylcoumarins, flavonoids and a novel phenylstyrene [15], [16], [17], [20], [21], [22]. In addition, Reher and Kraus reported the isolation of three 4-phenylcoumarins from H. latiflora [18].…”

Section: Introductionmentioning

confidence: 99%

Antihyperglycemic Effect of Constituents fromHintonia standleyanain Streptozotocin-Induced Diabetic Rats

et al. 2005

Self Cite

View full text Add to dashboard Cite

An extract (100 mg/kg) of the stem bark of Hintonia standleyana caused a significant decrease in blood glucose levels in both normal and streptozotocin (STZ)-diabetic rats when compared with vehicle-treated groups (p < 0.05). From the active extract, 3- O- beta- D-glucopyranosyl-23,24-dihydrocucurbitacin F ( 1), 5- O-beta- D-glucopyranosyl-7-methoxy-3',4'-dihydroxy-4-phenylcoumarin ( 2) and 5- O-[ beta- D-apiofuranosyl-(1-->6)- beta- D-glucopyranosyl]-7-methoxy-3',4'-dihydroxy-4-phenylcoumarin ( 3) were isolated. Coumarin 3 is a new natural product and was identified by spectroscopic methods. Compounds 1 and 3 did not decrease blood glucose levels in normal rats. However, in two different long-term subacute experiments, using animals with a developing diabetes condition and with STZ-induced diabetes, both compounds at daily doses of 10 mg/kg (developing diabetes condition) or 30 mg/kg (STZ-induced diabetes condition) provoked a significant antihyperglycemic activity (p < 0.05). Furthermore, compound 3 restored normal blood glucose levels in STZ-induced diabetic rats. In all cases, the groups treated with the active principles and the extract showed less body weight lost than the glibenclamide-treated and diabetic control groups (p < 0.05). These results showed that the antihyperglycemic active principles of H. standleyana are both 4-phenylcoumarins and cucurbitacin glycosides.

show abstract

A phenylstyrene from Hintonia latiflora

Cited by 22 publications

References 4 publications

Phloroglucinol compounds of natural origin

Phloroglucinol compounds of natural origin

An Efficient Synthesis of Neoflavonoid Antioxidants Based on Montmorillonite K-10 Catalysis

Antihyperglycemic Effect of Constituents fromHintonia standleyanain Streptozotocin-Induced Diabetic Rats

Contact Info

Product

Resources

About