Myricetin and myricetin-3-O-l-rhamnoside from the leaves of Madhuca indica and Achras sapota

Subramanian, S.Sankara; Nair, A.G.R.

doi:10.1016/0031-9422(72)80119-5

Cited by 19 publications

(20 citation statements)

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“…Fruits are astringent and largely employed as a lotion in chronic ulcer, in acute and chronic tonsillitis and pharyngitis. The constituents reported from Madhuca indica include fatty acids [4 ± 6], sapogenins [7], carbohydrates [6] [8], triterpenoids [1] [8 ± 10], steroids [1] [8 ± 11], saponins [12] [13], flavonoids [9] [10] [14], and glycosides [8 ± 10] [14]. In view of the attributed medicinal properties, we investigated the fruit coats of M. indica, which resulted in the isolation and characterization of three new constituents: madhucic acid (1), a pentacyclic triterpenoid, madhushazone (2), an untypical isoflavone, and madhusalmone (3), a bis(isoflavone).…”

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confidence: 99%

Chemical Constituents from the Fruits of Madhuca latifolia

Siddiqui

Khan

Kardar

et al. 2004

Helvetica Chimica Acta

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From the fruit coats of the medicinal plant Madhuca latifolia were isolated three new compounds, the triterpenoid madhucic acid ( 3b-(octanoyloxy)-11-oxoolean-12-en-28-oic acid; 1), the untypical isoflavone madhushazone ( 9-methoxy-7-(2,3,6-trimethoxyphenyl)- [1,3]dioxolo [4,5-g][1]benzopyran-8(8H)-one; 2), and a bis(isoflavone) named madhusalmone ( 5,14-dimethoxy-3,12-bis(3,4,5-trimethoxyphenyl)-1,6,8,10,15,17-hexaoxanaphtho[2',3': 6,7]cyclodeca[1,2-b]naphthalene-4,13(4H,13H)-dione; 3), as well as eight known constituents, and their structures were elucidated by spectral analysis, including 2D-NMR techniques.Introduction. ± Madhuca latifolia Syn. M. indica (Sapotaceae) is an important economic plant growing throughout the subtropical region of the Indo-Pak subcontinent [1]. The medicinal properties attributed to this plant are stimulant, demulcent, emollient, heating, and astringent [2]. The bark is a good remedy for itch, swellings, fractures, and snake-bite poisoning, internally employed in diabetes mellitus with much benefit [3]. Mahua oil is used for the treatment of skin diseases, rheumatism, headache, and as a laxative. Fruits are astringent and largely employed as a lotion in chronic ulcer, in acute and chronic tonsillitis and pharyngitis. . In view of the attributed medicinal properties, we investigated the fruit coats of M. indica, which resulted in the isolation and characterization of three new constituents: madhucic acid (1), a pentacyclic triterpenoid, madhushazone (2), an untypical isoflavone, and madhusalmone (3), a bis(isoflavone). Moreover, eight known constituents were isolated and identified by comparison of their physical and spectral data with those reported in the literature. These included b-amyrin acetate, hitherto unreported b-amyrin caprylate, 3b-(capryloxy)ursolic acid, a hydrocarbon (C 29 H 60 ), a triglyceride of palmito-dioleins, and three monoglycerides of stearic, oleic, and arachidic acid, respectively. These glycerides have previously been found in solid seed fats of the same species [15].

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confidence: 99%

Chemical Constituents from the Fruits of Madhuca latifolia

Siddiqui

Khan

Kardar

et al. 2004

Helvetica Chimica Acta

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“…Myricetin, a flavonoid compound with hydroxyl substitutions at the 3, 5, 7, 3 0 , 4 0 , and 5 0 positions [20], has been reported to possess antioxidative, antiproliferative, and anticarcinogenic effects [21]. Myricetin isolated from Myrica rubra Sieb.…”

Section: Discussionmentioning

confidence: 99%

Antinociceptive and anti-inflammatory effects of myricetin 3-O-β-galactoside isolated from Davilla elliptica: involvement of the nitrergic system

et al. 2015

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We aimed to study the antinociceptive effects of myricetin 3-O-β-galactoside (Mi), a substance isolated from the hydroalcoholic extract of Davilla elliptica. This study examined male Swiss mice, inducible nitric oxide synthase C57B16/J knockout mice (iNOS(-/-)), and their corresponding wild type (WT). Formalin and tail-flick tests were used to evaluate the nociceptive threshold, and the carrageenan-induced paw edema test was used as a model for inflammation. The following drugs were administered to investigate the involvement of the nitrergic and opioidergic systems: L-NAME, a nonspecific nitric oxide synthase (NOS) inhibitor; L-arginine (L-Arg), a precursor for the synthesis of nitric oxide (NO); D-arginine (D-Arg), an inactive isomer for the synthesis of NO; aminoguanidine (Am), an inducible nitric oxide synthase (iNOS) inhibitor; and naloxone, a nonselective antagonist of opioid receptors. The results showed that oral pretreatment with Mi caused a dose-dependent inhibition of the inflammatory phase of the formalin test and did not alter motor performance. Intraperitoneal injection of L-NAME caused a reduction in the licking time during the second phase of the formalin test. The administration of L-Arg (but not D-Arg) reversed the antinociceptive effect of L-NAME. Furthermore, pre-administration of aminoguanidine potentiated the antinociceptive effect. Mi did not cause an antinociceptive effect in iNOS knockouts and led to a reduction in the nitrite concentration in the paws of mice. Carrageenan-induced paw edema was reduced in Swiss mice and WT mice when compared to iNOS(-/-) mice. Pre-administration of naloxone (NLX) did not reverse the antinociceptive effect of Mi, excluding the opioidergic system as a mediator of the antinociceptive effect. Thus, the results suggest that the antinociceptive and anti-inflammatory effects of myricetin 3-O-β-galactoside are related to peripheral inhibition of nitric oxide synthesis, mainly iNOS.

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“…Myricetin (Fig. 1), a flavonoid compound with hydroxyl substitutions at the 3,5,7,3',4' and 5' positions (Subramanian and Nair, 1972), has been reported to possess antioxidative, antiproliferative and anticarcinogenic effects as major biological features (Gordon and Roedig-Penman, 1998). Myricetin also possesses neuroprotective effect on the Parkinson models both in vivo and in vitro through its antioxidation and anti-apoptosis activity (Yang et al, 2001).…”

Section: Introductionmentioning

confidence: 97%

Analgesic activity of myricetin isolated from Myrica rubra Sieb. et Zucc. leaves

et al. 2009

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Myrica rubra Sieb. et Zucc. leaves are commonly used as an astringent, antidiarrheic, and analgesics in folk medicine in China. In the present study, the analgesic activity of myricetin, a major compound in Myrica rubra Sieb. et Zucc. leaves was evaluated in vivo. The analgesic effect of myricetin was tested by a serial of models, such as acetic acid-induced writhing response, formalin-induced paw licking and hot plate test. The sedative activity was evaluated by pentobarbital-induced sleep time. Platelet aggregation induced by collagen and arachidonic acid was also performed in vitro. Myricetin showed a significant inhibition on chemical nociceptive models such as the acetic acid-induced writhing response and the licking time on the late phase in the formalin test in a dose-dependent manner, but did not manifest a signicant effect in hot plate test. Myricetin was also not able to increase the sleeping time induced by pentobarbital, which further indicated that the analgesic effect of myricetin was unrelated to sedation. In addition, myricetin inhibited the content of PGE2 in the peritoneal fluid and platelet aggregation induced by collagen and arachidonic acid in vitro. These results collectively demonstrated that myricetin possessed potent analgesic activity, which was related with peripheral analgesia, but, not with the opioid system. Myricetin may be a potent COX-1 inhibitor with anti-platelet activity.

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Myricetin and myricetin-3-O-l-rhamnoside from the leaves of Madhuca indica and Achras sapota

Cited by 19 publications

References 4 publications

Chemical Constituents from the Fruits of Madhuca latifolia

Chemical Constituents from the Fruits of Madhuca latifolia

Antinociceptive and anti-inflammatory effects of myricetin 3-O-β-galactoside isolated from Davilla elliptica: involvement of the nitrergic system

Analgesic activity of myricetin isolated from Myrica rubra Sieb. et Zucc. leaves

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