Unusual Naphthoquinone Derivatives from the Twigs of Avicennia marina

Abstract

In a continuing search for novel bioactive compounds from marine mangrove plants, seven new naphthoquinone derivatives were isolated from Avicennia marina, namely, avicennone A (1), avicennone B (2), avicennone C (3), avicennone D (4), avicenone E (5), avicennone F (6), and avicennone G (7), along with the known compounds avicequinone A (8), stenocarpoquinone B (9), avicequinone C (10), avicenol A (11), and avicenol C (12). The chemical structures of 1-7 were elucidated by spectroscopic methods. Compounds 8-10, and a mixture of 4 and 5, which all contain a 4,9-dione group, showed strong antiproliferative and moderate cytotoxic activities, as well as antibacterial effects.

The genusAvicennia, a pioneer group of dominant mangrove plant species with potential medicinal values: a review

“…As Table 4, a total of 14 flavonoids including flavones, 19 naphthalene derivatives, 5 terpenoids, 7 steroids, 23 tannins 6 fatty acids, 31 glucosides from wide variety of secondary metabolite classes have been listed to date in genus Avicennia (Majumdar et al 1981;Sharaf et al 2000;Jia et al 2004;Feng et al 2007). Phytochemical studies have revealed that most chemically investigated Avicennia species till now are rich in phytochemicals, namely terpenoids, glucosides and naphthalene derivatives (Konig & Rimpler 1985;Sutton et al 1985;Shaker et al 2001;Han et al 2007). These naturally occurring compounds are found to be concentrated in the plant's leaf, stem/bark and aerial roots.…”

“…These naturally occurring compounds are found to be concentrated in the plant's leaf, stem/bark and aerial roots. A number of pharmacologically important phyto-constituents belonging to different classes of phytochemicals which have been isolated include flavonoids (3) (Konig et al 1994;Gonzales et al 2000;Ramirez & Roa 2003;Han et al 2007Han et al , 2008Manilal et al 2009, Sumithra et al 2011bHossain et al 2012;Mahera et al 2013;Jain et al 2014;Ramanjaneyulu et al 2015). A detailed report on their occurrence, chemical structure and bioactivity has been presented in Table 5.…”

“…Few studies have been undertaken to characterize and identify the bioactive principle responsible of antimicrobial activity in Avicennia plants (Han et al 2007(Han et al , 2008Manilal et al 2009;Chinnappan et al 2013). The antimicrobial effect can be corroborated with the presence of naphthalene derivatives ( officinalis has also been reported to exhibit the antimicrobial activity.…”

“…The cytotoxicity activity can be attributed to the presence of flavonoids (3) having anticancer activity that can kill human promyelocytic leukaemia cells by apoptosis mechanism (Ramanjaneyulu 2015). In addition, the plant is also reported to possess anticancer compounds such (20), (22), (23), (31), (55) and (56) in its stem as well as (49) in its root (Han et al 2007;Sumithra et al 2011b;Hossain et al 2012). Sumithra et al (2011a), in another anticancer study, reported cytotoxicity activity of A. officinalis in Ehrlich ascitic carcinoma cell lines.…”

The Chemical Investigations of the Mangrove Plant Avicennia marina and its Endophytes!

“…From the leaves of A. marina collected in Beihai, Guangxi province, Jia et al [9] also isolated two naphthoquinone derivatives identified as avicequinone B (12) and avicequinone C (13). In 2007, Han et al [13] reported seven unusual naphthoquinone derivatives were isolated from the twigs of A. marina collected in Xiamen province, namely, avicennone A-G (14)(15)(16)(17)(18)(19)(20), along with the known compounds avicequinone A (21), stenocarproquinone B (22), avicequinone C (13), avicenol A (23), and avicenol C (24).…”