Introduction

Andrographis paniculata (Burm. f) Nees (Acanthaceae) is a well-known bitter medicinal herb found in the Far East (specifically in India, Southeast Asia, the northern parts of the Malayan peninsula, Java, and southern parts of China). It is also cultivated commercially. It is an erect, stiff herb, growing up to 1 m tall, with quadrangular stems that are thickened above the nodes. The leaves are opposite, lanceolate (3-12 cm by 1-3 cm) while flowers are narrow, white, tube-like, and appear as laxly branched terminal or axillary inflorescences

The herb is known by several other names—Justiciapaniculata Burm. f.; Hempedu bumi, Sambiloto, Sambiroto (Javanese/Malay), Chuan xin lian (Chinese).

Figure 1 Andrographispaniculata (Burm. f) Nees (Acanthaceae). (Courtesy of Dr. Andrew Wee Kien Han.)

II. CHEMICAL CONSTITUENTS OF A. PANICULATA

The chemical constituents of A. paniculata are mainly diterpenoids (which all contain hydroxyl, a, h-unsaturated-g lactone, and exomethylene groups in their chemical structures) and flavonoids. The diterpenoids include andrographolide (1), 14-deoxyandrographolide (DA), 14-deoxy-11,12-dide-hydroandrographolide (DDA), 14-deoxy-11-oxoandrographolide (2), neo-andrographolide (3), andrographiside (di-deoxyandrographolide), deoxy-andrographoside (andropanoside), andrograpanin, deoxyandrographolide 19-D-glucoside, and 14-deoxy-12-methoxy-andrographolide (4-7).

Figure 2 Chemical structures of DA (1), DDA (2), andrographolide (S) andrographiside (4), and neoandrographolide (5).

Matsuda et al. (8) reported the isolation of six new diterpenoids of the ent-labdane type, viz. 14-epi-andrographolide, isoandrographolide, 14-de-oxy-12-hydroxyandrographolide, and 14-deoxy-11-hydroxyandrographolide and the diterpene glucosides 14-deoxy-11, 12-didehydrographiside, and 6'acetyl-eoandrographolide. Four new diterpene dimers, bis-andrographo-lides, A, B, C, and D, from the aerial parts (including seeds, stem, and leaves) of A. paniculata were also isolated and their structure determined by chemical and spectral analysis (8).

From the root of the plant, a new flavonone glucoside, andrographidine (A), and five new flavone glucosides, andrographidine B, C, D, E, and F, were isolated along with 5-hydroxy-7, 8, 2'-, 3'-tetramethoxyflavone, and 7, 8-dimethoxy-5-hydroxyflavone. They have uncommon O-substitution pattern including 5,7-8-,2'-,3'- and 4'O-substituents (9). Tang and Eisenbrand (10) reported that the main constituent of A. paniculata was andrographolide.

DA (Fig. 2,1), C20H30O4, is a colorless plate crystal (from methanol) with hydroxyl, a,h-unsaturated-g-lactone, and exo-methylene groups in its chemical structure. It was reported to possess antipyretic and anti-inflammatory effects (10,11).

DDA (Fig. 2,2), C20H28O4, is a colorless needle crystal (from methanol) with hydroxyl, a,h-unsaturated-g-lactone, and exo-methylene groups present in its chemical structure (2). This is very similar to that of 14-deoxyandrographolide, with the exception of a double bond at C-11 and 12. So far, there has been no literature report on the biological activities of DDA.

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