- Synthesis of novel and diverse mollugin analogues and their antibacterial and antioxidant activities
-
Novel and diverse mollugin analogues (1-12) were synthesized using PhB(OH)2/AcOH-mediated electrocyclization reaction as a key step. The newly synthesized compounds were screened for antioxidant and antibacterial activities. Compounds 1, 2, 5, 6, 8, and 10-12 showed high antioxidant activities in DPPH inhibition (IC50 = 0.52-1.11 μM) compared with BHT (IC50 = 9.67 μM). Compounds 3 exhibited potent antibacterial activity against Staphylococcus aureus (KCTC-1916) bacterial strain at 100 μg/mL. Structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR data and high-resolution mass spectrometry.
- Idhayadhulla, Akber,Xia, Likai,Lee, Yong Rok,Kim, Sung Hong,Wee, Young-Jung,Lee, Chong-Soon
-
-
Read Online
- Pericyclic reactions of prenylated naphthoquinones: Biomimetic syntheses of mollugin and microphyllaquinone
-
(Chemical Equation Presented) A total synthesis of the bioactive naphthohydroquinone mollugin and the related naphthoquinone dimer microphyllaquinone is described. Both syntheses exploit the propensity of prenylated quinones to undergo tautomerization/oxa 6π-electrocyclizations.
- Lumb, Jean-Philip,Trauner, Dirk
-
-
Read Online
- CF3-substituted mollugin 2-(4-morpholinyl)-ethyl ester as a potential anti-inflammatory agent with improved aqueous solubility and metabolic stability
-
Although mollugin, the main ingredient of the oriental medicinal herb Rubia cordifolia, has considerable anti-inflammatory effects, it has poor aqueous solubility as well as poor metabolic and plasma stability. To overcome these shortfalls, various mollug
- Hong, Ki Bum,Kim, Darong,Kim, Bo-Kyung,Woo, Seo Yeon,Lee, Ji Hoon,Han, Seung-Hee,Bae, Gyu-Un,Kang, Soosung
-
-
- Mollugin derivatives, optical isomer thereof, or pharmaceutically acceptable salts thereof, and a pharmaceutical composition for preventing or treating inflammatory bowel disease comprising the same as an active ingredient
-
The present invention relates to mollugin derivatives, an optical isomer thereof, or pharmaceutically acceptable salts thereof, and a pharmaceutical composition for preventing or treating inflammatory bowel disease comprising the same as an active ingredient. The mollugin derivatives of the present invention become salts easily by introducing an amine group, so that a solubility improvement effect is remarkable compared to existing poorly-soluble substances, and in the case of treatment with the mollugin derivatives, the activity of inhibiting the adhesion of U937 cells, which are monocytic cells, in TNF-andalpha; or IL-6-inducible HT-29 cells was excellent, thereby being useful as pharmaceutical compositions for prevention or treatment of inflammatory bowel disease.(AA) Example 7 (10 andmu;M)(BB) Example 21 (10 andmu;M)COPYRIGHT KIPO 2017
- -
-
Paragraph 0062
(2017/12/15)
-
- Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin
-
Organocatalytic asymmetric epoxidation of chromenes mediated by iminium salt catalysts under non-aqueous conditions provided ees as high as 99%. Contrastingly, reaction under aqueous conditions can form the corresponding diol products with ees as high as 71%. The process has been used for the synthesis of the East African medicinal plant metabolite (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin.
- Bulman Page, Philip C.,Chan, Yohan,Noor Armylisas, Abu Hassan,Alahmdi, Mohammed
-
p. 8406 - 8416
(2016/12/06)
-
- New mollugin analogues and their antioxidant and antibacterial activities
-
The present invention relates to a new mollugin analogue and medical use thereof and, more specifically to newly synthesized mollugin analogues having both antibacterial and antioxidant activities, which can be effectively used as a medicine for oxidation-related diseases or as an antibacterial agent.
- -
-
Paragraph 0035; 0067-0074
(2021/05/31)
-
- Facile synthesis of mollugin by kinetic control and anti-HCV (Hepatitis C Virus) activity of its analogues
-
Mollugin has been reported to have various biological activities including antineoplastic, antitumor, antiviral against the hepatitis B virus, anti-aging and antimutagenic activities. An effective and concise synthesis of mollugin in two steps including kinetic control from the cheap starting material 1,4-naphthoquinone has been introduced, and mollugin derivatives thus prepared are screened for their inhibition ability against the hepatitis C virus (HCV) and the dihydrobenzochromene structure might be an additional anti-HCV agent as a new leading compound.
- Choi, Da Hye,Lee, Na Ri,Kim, Cheol Gi,Kim, Jong Woo,Lee, Sang Wook,Jun, Jong-Gab
-
p. 3232 - 3238
(2015/04/22)
-
- Synthesis of the natural products 3-hydroxymollugin and 3-methoxymollugin
-
(Figure Presented) 3-Hydroxymollugin 2 and 3-methoxymollugin 3 are cytotoxic compounds isolated as minor compounds from Pentas longiflora and Rubia cordifolia. Syntheses of 3-hydroxymollugin 2 and 3-methoxymollugin 3 were developed starting from easily available 3-bromomollugin 6. Surprisingly, it was found that the reaction of 3-bromomollugin 6 with sodium methoxide in methanol resulted in the formation of 3-methoxymollugin 3 and the ring-contracted methyl isopropenylfuromollugin 7. A mechanism for this ring contraction is proposed on the basis of a pericyclic retro oxa-6π ring-opening reaction. A second synthesis of 3-hydroxymollugin 2 was based on epoxidation of methyl 3-(3-methylbut-2-enyl)-l,4-naphthoquinone-2-carboxylate 17 and subsequent reduction of the quinone moiety, ring transformation, and DDQ oxidation. The latter oxidation process results in 3-hydroxymollugin 2 along with the rearranged furomollugin 4, which is a ring-contracted analogue of the natural product mollugin 1.
- Sastry, Mudiganti Naga Venkata,Claessens, Sven,Habonimana, Pascal,De Kimpe, Norbert
-
scheme or table
p. 2274 - 2280
(2010/07/02)
-
- Efficient one-pot trans-dihydroxylation of 2H-pyrans using dimethyldioxirane (DMD): synthesis of trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin natural products
-
An efficient one-pot formation of trans-diols on 2H-pyranyl rings was achieved by dimethyldioxirane in wet acetone. This new methodology was applied to the synthesis of natural products containing trans-diol on the pyranyl rings such as trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin.
- Wang, Xue,Lee, Yong Rok
-
p. 6275 - 6280
(2008/02/10)
-
- A novel method for the synthesis of substituted benzochromenes by ethylenediamine diacetate-catalyzed cyclizations of naphthalenols to α,β-unsaturated aldehydes. Concise synthesis of the natural products lapachenole, dihydrolapachenole, and mollugin
-
A new synthetic route for biologically interesting benzochromenes was developed starting from naphthalenols and α,β-unsaturated aldehydes in the presence of ethylenediamine diacetate. This methodology was applied for the total synthesis of the biologicall
- Yong, Rok Lee,Yun, Mi Kim
-
p. 2401 - 2413
(2008/03/29)
-
- Efficient syntheses of mollugin
-
Two different strategies are presented to synthesize mollugin, based upon a close investigation of possible natural precursors. The best total synthesis of mollugin, a natural product isolated from rubiaceous herbs, is achieved in an overall yield of 61% starting from 1,4-dihydroxynaphthalene-2-carboxylic acid. The key reaction is the prenylation and spontaneous pyran ring formation. Subsequent oxidation of the intermediate 3,4-dihydromollugin with DDQ afforded mollugin. Georg Thieme Verlag Stuttgart.
- Habonimana, Pascal,Claessens, Sven,De Kimpe, Norbert
-
p. 2472 - 2475
(2008/02/11)
-
- Synthesis of mollugin
-
The total synthesis of mollugin, a major constituent of rubiaceous herbs, using a straightforward synthetic approach starting from 1,4-naphthoquinone via a sequence of reactions, including selective prenylation, epoxidation, reduction of the quinone moiety, acid-catalysed ring expansion, bromination, dehydration and methoxycarbonylation is presented.
- Claessens, Sven,Kesteleyn, Bart,Nguyen Van, Tuyen,De Kimpe, Norbert
-
p. 8419 - 8424
(2007/10/03)
-
- Synthesis of naturally occurring rubilactone, mollugin, and dihydromollugin of Rubia cordifolia
-
Rubilactone (1), dihydromollugin (2), and mollugin (3) are naturally occurring products found in Rubia cordifolia, which is a famous Chinese herb with antitumor, viral inhibition and other activities. Synthetic studies were carried out in these naphthoic acid esters starting from 1,4-dihydroxy-2-naphthoic acid. In this study, we finished the synthesis of rubilactone which has not been reported before and also synthesized dihydromollugin and mollugin with better yields with different approaches compared to those previously reported in the literature.
- Ho, Li-Kang,Yu, Hsi-Jung,Ho, Chen-Ta,Don, Ming-Jaw
-
-
- BIOSYNTHESIS OF ANTHRAQUINONES AND RELATED COMPOUNDS IN GALIUM MOLLUGO CELL SUSPENSION CULTURES
-
From Galium mollugo cell suspension cultures, 1,4-dihydroxy-3-prenyl-2-naphtholic acid methyl ester diglucoside was isolated along with anthraquinones and mollugin.Production of the diglucoside was much increased by administering 2-succinylbenzoate to the cultures.The incorporation of 2-succinylbenzoate into lucidin-3-primeveroside, mollugin and the diglucoside in the mode so far proposed for rubiaceous anthraquinones was verified by administration of 13C-labelled 2-succinylbenzoate to the cell cultures.Key Word Index - Galium mollugo; Rubiaceae; lucidin-3-primeveroside; 1,4-dihydroxy-3-prenyl-2-naphthoic acid methyl ester diglucoside; biosynthesis; cell suspension culture; 13C NMR; mass spectrometry.
- Inoue, Kenichiro,Shiobara, Yoshinori,Nayeshiro, Hidekazu,Inouye, Hiroyuki,Wilson, Graham,Zenk, Meinhart H.
-
p. 307 - 312
(2007/10/02)
-
