Five Hundred Lords of Ayyavolu in the context of "Chola Dynasty"

In 1025 AD, the Chola Emperor Rajendra I launched naval invasions on Srivijaya in maritime Southeast Asia, leading to the fall of the Sailendra Dynasty of Srivijaya.

Rajendra's overseas expedition against Srivijaya was a unique event in India's history and its otherwise peaceful relations with the states of Southeast Asia. Several places in present-day Indonesia and Malay Peninsula were invaded by Rajendra I of the Chola dynasty. The invasion furthered the expansion of Tamil merchant associations such as the Manigramam, Ayyavole and Ainnurruvar into Southeast Asia.

Manigiramam, or manigramam, typically refers to a medieval merchant guild organized by itinerant ethnic Indian traders, primarily active in southern India. Along with the ainurruvar (the Ayyavole Five Hundred) and the anjuvannam (the anjuman), the manigiramam played a significant role in the commercial activities of the region. Unlike the anjuvannam, which was confined to the port-towns of southern India, the manigramam operated in both port towns and hinter-land trade centers.

A body of merchants known as "the Vaniggrama" or "Vaniyagrama" is attested in northern India as early as the first century BCE. They are mentioned in a Karle inscription (first century BCE), a charter of king Vishnusena from Kathiawad (6th century CE), and in a Sanjeli charter of king Toramana (6th century CE).

Ainnurruvar is a medieval merchant guild originating in the Karnataka region of India between the 8th and 13th centuries. In this period, organised merchant guilds exerted considerable power and influence. Ainnurruvar was one of the most prominent of these guilds. During the Chola Empire they were regarded as the elite amongst the South Indian merchant organizations.

The Five Hundred Lords of Ayyavole were a merchant guild from Aihole that provided trade links between trading communities in Tamil Nadu, Karnataka and Andhra Pradesh. They have been mentioned in inscriptions from the 9th century CE. Aihole was formerly a major city of the Chalukyas of Badami and a place with many temples and brahmins, some of whom seem to have become involved in the trading activities of the Five Hundred. But most of the Ayyavolu Lords were merchants, especially those engaged in long-distance trade. Their inscriptions between the 9th and 14th centuries record their endowments made to temples and throw light on their trading activities or commodities.