New Diterpenes from a Godavari Mangrove, Ceriops decandra

Abstract

Eleven new diterpenes, named decandrins A-K (1-11), including nine abietanes (1-9) and two podocarpanes (10-11), were isolated from the barks of an Indian mangrove, Ceriops decandra, collected in the mangrove swamp of Godavari estuary, Andhra Pradesh, together with four known abietanes. The structures of these compounds were established on the basis of spectroscopic data (new compounds) or comparison with data in the literature (known compounds). This is the first report of abietane and podocarpane diterpenoids from C. decandra.

Decandrinin, an unprecedented C9-spiro-fused 7,8-seco-ent-abietane from the Godavari mangrove Ceriops decandra

“…As described previously [7] the bark of Ceriops decandra were collected in September 2009 in the estuary of Godavari, Andhra Pradesh, India. The identification of the plant was performed by one of the authors (T.S.).…”

“…The extraction and isolation procedures were in part identical to those described recently [7]: The chloroform extract (65.2 g) from air-dried bark (7.4 kg) of C. decandra was subjected to silica-gel column chromatography (200−300 mesh, 3.0 kg) and eluted with petroleum ether/acetone (100:0 to 1:2) to yield 285 fractions. Fractions 173 to 204 were combined and further purified using RP C 18 column chromatography eluted with acetone/H 2 O (30:70 to 100:0) to give 57 subfractions.…”

“…Before our work, already 28 compounds had been isolated from C. decandra [6] (three pimaranes, four beyeranes, five kauranes, and 16 lupanes). Recently, some of us have reported on the isolation of eleven new diterpenes from this plant, named decandrins A–K [7], of which nine belong to the group of abietanes.…”

Triterpenes From Ceriops Decandra (Griff.) W. Theob.

“…Another study reported that the leaf extracts afforded α-amyrin, β-amyrin, lupeol, oleanolic acid, and ursolic acid [5]. The bark of C. decandra yielded decandrins A-K [6]; 2-(9-hydroxy-3a,5a,5b,8,8,11a-hexamethylicosahydro-1H-cyclopenta[a]chrysen-1-yl) propanoic acid (3β-hydroxylupan-29-oic acid) [7]; d-catechin, leucoanthocyanidins [4]; procyanidin [8]; decandrinin [9]; (-)-syringaresinol, (-)-pinoresinol, β-sitosterol, stigmasterol, palmitic acid, and 3,4-dihydroxybenzoic acid Et ester [10]; and 7,13-abietadien-3β-ol, 7-oxodehydro-abietinol, margocin, 3β-hydroxy-abieta-8,11,13-trien-7-one, 15,18-dihydroxyabieta-8,11,13-trien-7-one, 7β,18-dihydroxy dehydroabietanol, 4-epitriptobezene L, 7α, 18-dihydroxydehydroabietanol, sabiperone E, 13β,18-dihydroxy-abiet-8(14)-ene-7-one, ent-labd-8(17),13E-dien-15-ol, ent-8(14)-pimarene-15R,16-diol, and (5S*,8S*,9S*,10R*,13S*)-3-hydroxy-16-nor-2-oxodolar-3-ene-15-oic acid [11]. Furthermore, the wood extract of C. decandra yielded 3β,13β-dihydroxy-8-abietaen-7-one and 3β-hydroxy-8,13-abietadien-7-one [12].…”

Mangrove dolabrane‐type of diterpenes tagalsins suppresses tumor growth viaROS‐mediated apoptosis and ATM/ATR–Chk1/Chk2‐regulated cell cycle arrest

“…The mangrove genus Ceriops has recently attracted attention due to containing rich secondary metabolites with antibacterial and larvicidal activities 3, 4. The main constituents of the secondary metabolites of Ceriops are diterpenoids and triterpenoids 3, 5…”