Isolation and synthesis of a novel immunosuppressive 17α-substituted dammarane from the flour of the Palmyrah palm (Borassus flabellifer)

Révész, Láśzló; Hiestand, Peter; Vecchia, Luigi La; Naef, Reto; Naegeli, Hans‐Ulrich; Oberer, Lukas; Roth, Hans‐Jörg

doi:10.1016/s0960-894x(99)00220-6

Cited by 36 publications

(17 citation statements)

References 13 publications

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“…It also exhibited another olefinic proton at d 5.35 (H-12) br s, which showed a one bond correlation with d C 122.57 (C-12) .62 (C-3 0 ) in HMBC plot confirmed the attachment of isopranoyl moiety with the dammarane skeleton at C-3 position. All the spectral assignment for rings A, B, C and D completely agreed with those reported data for dammarane triterpene (Ikram et al 2013;Sharma and Tandon 1982;Révész et al 1999;Majumder et al 2003).…”

Section: Resultssupporting

confidence: 87%

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New dammarane and ursane-type triterpenoids from the flower ofIxora coccineaLinn.

Ikram

Versiani

Khatoon

et al. 2015

Natural Product Research

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Two new esters of dammarane triterpenoids ixorene isovalerate (1), ixorene 3',8'-dimethyloctanoate (2) and a new ursane-type triterpenoids Ixoroid acid (3) were isolated from the methanolic extract of flowers of Ixora coccinea Linn., along with the three known constituents. The structures of compounds 1 and 3 were elucidated on the basis of extensive 1D,2D NMR studies and mass spectrometry as 17β-dammara-12,20-diene-3β-isovelarate and 3β-hydroxy-18β-urs-12ene-29β-oic acid, respectively, whereas 2 was identified as 17β-dammara-12,20-diene-3β-3',8'-dimethyloctanoate through (1)H NMR and mass spectral data. Compounds 1, 2, 4 and 5 were evaluated for their in vitro cytotoxic activity, which exhibited weak activity against the 3T3, PC3 and HeLa cell lines with the IC50 value >30 μM. Antioxidant results of 1 - 5 revealed that only compound 5 showed antioxidant activity in DPPH radical scavenging inhibition with the IC50 1.31 × 10(- 6) ± 0.005 μm mL(- 1). Both activities are the first records of these isolated compounds from the flowers of Ixora coccinea Linn.

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Section: Resultssupporting

confidence: 87%

“…The 17b configuration of the side chain in compound 1 is based on downfield chemical shift of H-17 at d 2.35 (Annapurna et al 2003;Révész et al 1999;Yodsaoue et al 2012;Kubo & Fukhara. 1990;De Pascual Teresa et al 1985) and NOESY interaction, where a crucial NOE is observed between H-17 and H-30, which confirmed that H-17 has a-orientation.…”

Section: Resultsmentioning

confidence: 99%

New dammarane and ursane-type triterpenoids from the flower ofIxora coccineaLinn.

Ikram

Versiani

Khatoon

et al. 2015

Natural Product Research

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“…The signals of aromatic carbons and their corresponding protons were observed at  C 111.31-160.44 ppm and  H 6.76-7.54ppm. Generally, the spectral data for the rings B, C, and D and side chain of compounds 5-3 are in complete agreement with those reported for dammaranes [7,14,[25][26].…”

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confidence: 86%

Synthesis of new A-conjugated Quinolone and Spiroindole Dammaranes by the Ozonolysis of 2,3-Indolodipterocarpol

Смирнова

Khusnutdinova

Лобов

et al. 2018

Natural Product Communications

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An one-step and efficient access to the new dammarane A-quinolones by ozonolysis of 2,3-indolodipterocarpol at 0°C through the 1,3-dipolar cycloaddition of ozone to the С2-С3 double bond of the triterpenoid core is reported. In the case of oxidation in AcOH, two spiroindoles were identified as a result of 1,2cycloaddition of ozone to the С2-С3 double bond with following intramolecular rearrangements of 2,3-epoxy-intermediate. The structures of four new compounds were established by 1H, 13C NMR, COSY, NOSY, HMBC and HSQC analyses.

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“…The same trends were observed in 22a-and 22b-N-spirostanol oligoglycosides, solamarine (28) and solamargine (29). 41) On the basis of above-mentioned evidence, the stereostructures of brssosides D-F were determined to be as shown (4)(5)(6).…”

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confidence: 99%

Medicinal Flowers. XII.1) New Spirostane-Type Steroid Saponins with Antidiabetogenic Activity from Borassus flabellifer

et al. 2007

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The Palmae plant, Borassus flabellifer L. (palmyra palm in English), is widely distributed and cultivated in tropical Asian countries such as Thailand, Bangladesh, India, Myanmar, Sri Lanka, Malaysia, etc. The fruit pulp of B. flabellifer has been used in traditional dishes and the sap, which was trapped from the flower part, has been used as a sweetener for diabetic patients. In the previous studies, several steroidal saponins, 2-4) a polysaccharide, 5) and a triterpene 6) constituents were isolated from the fruit pulp, seeds, and young shoot of B. flabellifer. However, the chemical and pharmacologic studies for the flower parts of this medicinal food were left uncharacterized. In the course of our characterization studies on Thai medicinal foods, [7][8][9][10][11][12][13][14][15][16][17][18][19][20] we found that the methanolic extract from the male flowers of B. flabellifer was found to inhibit the increase of serum glucose levels in sucrose-loaded rats. From the methanolic extract, six new spirostane-type steroid saponins, borassosides A-F (1-6), were isolated together with 20 known steroidal glycosides (7-25 and b-sitosterol 3-O-b-D-glucopyranoside) and three known steroids (26, 27, and b-sitosterol). This paper deals with the structure elucidation of borassosides A-F (1-6) from the male flowers of B. flabellifer as well as the inhibitory effects of the methanolic extract and a principal constituent, dioscin (13), on the increase of serum glucose levels in sucrose-loaded rats.Extraction and Isolation The male and female flowers of B. flabellifer (collected in Thailand) were extracted with methanol to give methanolic extracts (12.2% from the male flowers; 11.3% from the female flowers). As shown in Table 1, the methanolic extract from the male flowers of B. flabellifer was found to inhibit the increase of serum glucose levels in sucrose-loaded rats at a dose of 250 mg/kg, p.o. However, Yamashina-ku, Kyoto 607-8412, Japan: and b Pharmaceutical Research and Technology Institute, Kinki University; 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. Received October 18, 2006; accepted November 27, 2006; published online November 30, 2006 The methanolic extract from the male flowers of Borassus flabellifer was found to inhibit the increase of serum glucose levels in sucrose-loaded rats at a dose of 250 mg/kg, p.o. From the methanolic extract, six new spirostane-type steroid saponins, borassosides A-F (1-6), were isolated together with 23 known constituents. The structures of borassosides (1-6) were elucidated on the basis of chemical and physicochemical evidences. In addition, the principal steroid saponin, dioscin (13), inhibited the increase of serum glucose levels in sucroseloaded rats at a dose of 50 mg/kg, p.o.

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Isolation and synthesis of a novel immunosuppressive 17α-substituted dammarane from the flour of the Palmyrah palm (Borassus flabellifer)

Cited by 36 publications

References 13 publications

New dammarane and ursane-type triterpenoids from the flower ofIxora coccineaLinn.

New dammarane and ursane-type triterpenoids from the flower ofIxora coccineaLinn.

Synthesis of new A-conjugated Quinolone and Spiroindole Dammaranes by the Ozonolysis of 2,3-Indolodipterocarpol

Medicinal Flowers. XII.1) New Spirostane-Type Steroid Saponins with Antidiabetogenic Activity from Borassus flabellifer

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