Four new diterpene esters, shirakindicans A-D (<b>1</b>-<b>4</b>), along with eight related known diterpene esters (<b>5</b>-<b>12</b>), were isolated from the fruits of the Bangladeshi medicinal plant <i>Shirakiopsis indica</i>. The structures of <b>1</b>-<b>4</b> were elucidated by spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Shirakindican A (<b>1</b>) was assigned as a tigliane-type diterpene ester possessing an unusual 6β-hydroxy-1,7-dien-3-one structure, while shirakindican B (<b>2</b>) exhibits a tiglia-1,5-dien-3,7-dione structure. The anti-HIV activities of the isolated diterpene esters were evaluated and showed significant activities for sapintoxins A (<b>5</b>) and D (<b>11</b>), with EC<sub>50</sub> values of 0.0074 and 0.044 μM, respectively, and TI values of 1 100 and 5 290. Sapatoxin A (<b>12</b>) also exhibited anti-HIV activity with an EC<sub>50</sub> value of 0.13 μM and a TI value of 161.