On the Phloroglucinol Derivatives of Mallotus Philippiners

Lounasmaa, Mauri; Cj, Widén; Cm, Tuuf; Huhtikangas, Aarre

doi:10.1055/s-0028-1097825

Cited by 38 publications

(22 citation statements)

References 4 publications

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“…155.70 C(2''') 159.09 C (3) 102.80 C(3''') 99.93 C (4) 156.57 C(4''') 157.56 C (5) 109.17 C(5''') 99.09 C (6) 161.31 C(6''') 164.96 C (7) 193.57 C(7''') 203.41 C (8) 126.79 C(8''') 32.73 C (9) 143.78 C(9''') 69.84 C (10) 25.26 C(10''') 46.72 C (11) 42.12 C(11''') 79.37 C (12) 78.65 C(12''') 21.17 C (13) 27.36 C(13''') 28.33 C (14) 30.39 C(1'''') 105.94 C (15) 16.14 C(2'''') 154.62 C (1') 135.31 C(3'''') 98.14 C (2',6') 128.17 C(4'''') 159.51 C (3',5') 128.88…”

Section: C-nmr Data Of Kamalachalcone D (4)mentioning

confidence: 98%

Novel, Complex Flavonoids from Mallotus philippensis (Kamala Tree)

Furusawa

Ido

Tanaka

et al. 2005

Helvetica Chimica Acta

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One new flavanone, 4'-hydroxyisorottlerin (2), and two new chalcone derivatives, kamalachalcones C (3) and D (4), were isolated from Mallotus philippensis (kamala tree). The largest compound (4; M r 1098 g/mol) was shown to possess a unique, fused-ring system made of two hydroxy-chalcone units, giving rise to eight fused benzene/pyran units. From the same plant, the following six known compounds were also isolated: kamalachalcone A (5) and B (6), isoallorottlerin (7), isorottlerin (8), 5,7-dihydroxy-8-methyl-6-prenylflavanone (9); 6,6-dimethylpyrano(2'',3'': 7,6)-5-hydroxy-8-methylflavanone (10), and rottlerin (1). The structures of the new compounds were confirmed by in-depth spectral analyses, including 2D-NMR techniques, and the full 13 C-NMR assignments of the known flavanones 1 and 7 ± 10 are published for the first time.

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Section: C-nmr Data Of Kamalachalcone D (4)mentioning

confidence: 98%

Novel, Complex Flavonoids from Mallotus philippensis (Kamala Tree)

Furusawa

Ido

Tanaka

et al. 2005

Helvetica Chimica Acta

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“…Earlier investigations on Kamala dye have afforded various flavonoides. [2][3][4][5] Kamala powder is used as an anthelmintic and cathartic in traditional medicine. 6) Macrophages play an important role in non-specific host defense mechanisms.…”

Section: Mallotus Philippinensis Muell Arg (Euphorbiaceae) Ismentioning

confidence: 99%

Antiallergic Agents from Natural Sources 9. Inhibition of Nitric Oxide Production by Novel Chalcone Derivatives from Mallotus philippinensis (Euphorbiaceae)

2004

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Mallotus philippinensis MUELL. ARG. (Euphorbiaceae) iswidely distributed in the forestes of Kelara. The Granular hairs on the surface of fruits is called Kamala. It has been used as a drug and dye. Earlier investigations on Kamala dye have afforded various flavonoides.2-5) Kamala powder is used as an anthelmintic and cathartic in traditional medicine. 6) Macrophages play an important role in non-specific host defense mechanisms. 7) In macrophages, bacterial LPS alone or in combination with cytokines like interferon-g (IFN-g) is one of the best-characterized stimuli to induce the transcription of genes encoding pro-inflammatory proteins, resulting in cytokine release and synthesis of enzymes such as cyclooxygenase-2 (COX-2) 8) and inducible nitric oxide synthase (iNOS). 9) NO is a short-lived bioactive molecule that participate in the physiology and pathophysiology of many systems.10) NO is synthesized in vivo from L-arginine by NOS with NADPH and oxygen as cosubstrates.11) Large amounts of NO may lead to tissue damage. In inflammatory disease such as rheumatoid arthritis, excessive NO production by activated macrophages has been observed. Therefore, it would be valuable to develop potent and selective inhibitors of NO for potential therapeutic use.Previously, we reported that mallotophilippens A and B, phloroglucinol derivatives from M. philippinensis, suppressed the NO production and iNOS gene expression. 3)In this work, we isolated three novel chalcone derivatives, 1, 2 and 3 ( Fig. 1), from the hexane-soluble fraction and investigated the inhibitory effects of those compounds on NO generation from activated macrophages. Results and DiscussionCompound 1 (Table 1), indicated a 2,2-dimethylpyran system.The arrangement of the substituents and the placement of the pyran at the 4aЈ/8aЈ positions were established from the results of the heteronuclear multiple bond connectivity (HMBC) experiments (Fig. 2). The chelated hydroxyl group in ring B showed the expected Kumage-gun, Kagoshima 891-3604, Japan. Received June 6, 2004; accepted August 27, 2004 Three novel chalcone derivatives, mallotophilippens C (1), D (2) and E (3) were isolated from the fruits of Mallotus philippinensis MUELL. ARG. These compounds were identified, using chemical and spectral data, as 1-[6-(3,7-dimethyl-octa-2,6-dienyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-3-(4-hydroxy-phenyl)-propenone, 3- (3,4-dihydroxy-phenyl)-1-[6-(3,7-dimethyl-octa-2,6-dienyl)

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“…In 2005, a phytochemical investigation of an ethyl acetate extract of the leaves of the same species led to the isolation of a new phloroglucinol dimer, mallopallidusol (97) . Four phloroglucinol derivatives (kamalins) were isolated from M. philippinensis, including rottlerin (98) and isoallorottlerin (99) (Lounasmaa et al 1975). Isorottlerin (100) was also mentioned in M. philippinensis (Zaidi et al 2009).…”

Section: Phloroglucinol Derivatives (Table 14)mentioning

confidence: 99%

“…, 13 Shan et al (1985), 14 Cheng et al (1998), 15 Qi et al (2005, 16 Cheng and Chen (2000), 17 Xu et al (2008), 18 , 19 , 20 Xu et al (2006), 21 Zhao et al (2002), 22 Ono et al (1989), 23 Sasak and Chonjnacki (1973), 24 Nguyen et al (1997), 25 Groweiss et al (1994), 26 Hui and Li (1976) Saijo et al (1989b), 46 Nair and Rao (1993), 47 Roberts et al (1963), 48 Gupta et al (1953), 49 Lounasmaa et al (1975), 50 Gschwendt et al (1994) Jabbar et al (2006), 58 Akhtar and Ahmad (1992), 59 Hikino et al (1978), 60 Saijo et al (1989a), 61 Huang et al (1999), 62 Tomizawa et al (1976), 63 Sutthivaiyakit et al (2001), 64 Nakatsu et al (1981), 65 …”

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confidence: 96%