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Caralluma and Hoodia are genera of succulent plants belonging to the subfamily of Asclepiadoideae in the family of Apocynaceae. Caralluma is distributed in dry regions of tropical Asia and Africa, majority of species being indigenous to the Indian subcontinent and the Arabian Peninsula. The genus Hoodia is mainly found in the Kalahari desert regions in Southern Africa. We focus on Caralluma adscendens var. fimbriata and Hoodia gordonii due to their popularity and growing commercial interest during the past 20 years. Indeed, it was claimed that these succulent plants contain bioactive compounds, especially 14β-hydroxypregnane derivatives, which showed appetite-suppressant activity and weight loss properties. This chapter describes the isolation, biological properties, and synthesis of 14β-hydroxypregnane derivatives found in C. adscendens var. fimbriata and H. gordonii.