394. Rottlerin. Part I

Narang, K. S.; Rây, Jñanendra Nath; Roy, Bharpur Singh

doi:10.1039/jr9370001862

Cited by 5 publications

(4 citation statements)

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“…Natural occurrence of the kamalins. Due to the very easily occurring decomposition of rottlerin (Ia) [3,8,101 it is difficult to state which ones of the isolated or detected compounds are naturally occurring and which ones are artefacts. However, the very mild conditions used in the isolation procedure (cf.…”

Section: Isolation Of the Karnalinsmentioning

confidence: 99%

See 1 more Smart Citation

On the Phloroglucinol Derivatives of Mallotus Philippiners

Lounasmaa¹,

Cj²,

Cm³

et al. 1975

Planta Med

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Four phloroglucinol derivatives (kamalins) have been isolated from Mallotus philippinensis. These are rottlerin (la), isoallorottlerin (II), the ,,red compound" (III) and the ,,yellow compoundc' (IV). In addition. methylene-bis-rnethylphloroacetophenone (V) has been detected by TLC. The natural occurence of these substances is discussed. Rksumk Quatre de'rivks phloroglucinoliques (kamalines) ont e'tk isolks de Mallotus philippinensis. Ils sont la rottlkrine (la), Pisoallorottle'rine (II), la ,,substance rougeP (Ill), et la ,,substance jaune" (IV). De plus, le mkthylkne-bis-me'thylphloroacktophknone (V) a ktk dktectk par la CCM. L'existence naturelle des ces substances est discutke. Mallotus philippinensis (LAM.) M~~LL.-ARG. (Euphorbiaceae)' is a dioecious shrub or small tree indigenous to southeastern Asia and widely distributed throughout tropical Asia, Australia and the Philippines [I]. The drug, Kamala, a red powder consisting of glandular and stellate non-glandular hairs from the cHpsules of the plant, has long been used as an anthelminticum and as an orange dye for silk. Kamala has been included in several European pharmacopoeias. According to early chemical investigations [I], kamala contains phenolic compounds of which rottlerin (mallotoxin) is the main compound. It was first isolated in 1855 by ANDERSON [l]. AS a result of extensive studies by British [3-71, Indian [8-91, and German [10-111 investigators before World War I1 the structure (Ia) was accepted for rottlerin [ 6 ]. NARANG et al. [8-91 also isolated in 1937.a The genus Mallotus LOUR. consists of 140 species distributed in eastern and southeastern Asia, Indomalesia, New Caledonia, Fiji and northern and eastern Australia. Two taxa also occur in tropical Africa and Madagascar [2].

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Section: Isolation Of the Karnalinsmentioning

confidence: 99%

“…208-210" (ethyl acetate) (lit. m. p. 212' [3], 209' [8,9], 201-202' [lo], 206-207' [13], 199-201 [14] [3], 223-225' [14]). IR (KBr) v C = O and C = C 1630, 1590, and 1545 cm-1.…”

Section: Isolation Of Crude Kamalin and Rottlerin (Ia)mentioning

confidence: 99%

On the Phloroglucinol Derivatives of Mallotus Philippiners

Lounasmaa¹,

Cj²,

Cm³

et al. 1975

Planta Med

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“…Previous studies have isolated cardenolides [5][6][7] and kamalins [8][9][10] from this genus, and cytotoxic, [11][12][13] anti-tumor, 14) and human immunodeficiency virus (HIV) reverse transcriptase inhibitory activities 15) have also been described. Macrophages play major roles in host defense, immunity and inflammatory responses, where once activated they result in cytokine, oxygen and nitrogen species, and eicosanoid production.…”

mentioning

confidence: 99%

Anti-allergic Agents from Natural Sources. (4): Anti-allergic Activity of New Phloroglucinol Derivatives from Mallotus philippensis (Euphorbiaceae).

Daikonya

Katsuki

Wu³

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Rottlerin ( 1 ) is a dimeric phloroglucinol compound that comprises two substituted phloroglucinol units linked to each other via a methylene group. This kind of dimeric phloroglucinol compound can be obtained synthetically via coupling of two phloroglucinol partners in the presence of formaldehyde under acidic conditions. , It has been reported that 1 is unstable under alkaline and acidic conditions. − During our efforts on semisynthetic modifications of rottlerin, when this compound ( 1 ) was reacted with benzyl bromide in the presence of potassium carbonate, the formation of four major products was observed, as depicted in Figure . All these products were isolated and characterized.…”

mentioning

confidence: 97%

Semisynthesis of Mallotus B from Rottlerin: Evaluation of Cytotoxicity and Apoptosis-Inducing Activity

et al. 2013

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Mallotus B (2d) is a prenylated dimeric phloroglucinol compound isolated from Mallotus philippensis. There have been no reports on the synthesis or biological activity of this compound. In the present paper, a semisynthetic preparation of mallotus B is reported via base-mediated intramolecular rearrangement of rottlerin (1), which is one of the major constituents of M. philippensis. The homodimer "rottlerone" was also formed as one of the products of this base-mediated intramolecular reaction. Rottlerin (1), along with rottlerone (2c) and mallotus B (2d), was evaluated for cytotoxicity against a panel of cancer cell lines including HEPG2, Colo205, MIAPaCa-2, PC-3, and HL-60 cells. Mallotus B (2d) displayed cytotoxicity for MIAPaCa-2 and HL-60 cells with IC₅₀ values of 9 and 16 μM, respectively. Microscopic studies in HL-60 cells indicated that mallotus B (2d) induces cell cycle arrest at the G1 phase and causes defective cell division. It also induces apoptosis, as evidenced by distinct changes in cell morphology.

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394. Rottlerin. Part I

Cited by 5 publications

References 0 publications

On the Phloroglucinol Derivatives of Mallotus Philippiners

On the Phloroglucinol Derivatives of Mallotus Philippiners

Anti-allergic Agents from Natural Sources. (4): Anti-allergic Activity of New Phloroglucinol Derivatives from Mallotus philippensis (Euphorbiaceae).

Semisynthesis of Mallotus B from Rottlerin: Evaluation of Cytotoxicity and Apoptosis-Inducing Activity

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