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Around 125 million years ago, plants developed flowers, which are the sexually reproducing organ of the plant. This allowed genes to intermingle and also provided edible food for humans (like apples).
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412 million years ago, plants appear with stems, the spine of today's plants.
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424 million years ago, plants (specifically trees) started having bark.
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418 million years ago, plants started having spores (which are the bean sprout like growths that appear on bread mold).
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Around 409 million years ago, plants developed roots to anchor themselves to the ground and to draw nutrients and moisture from the earth around them.
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Around 408 million years ago, plants started having leaves, which allowed them to expand their surface area for photosynthesis.
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369 million years ago, plants developed seeds as a means of reproducing themselves to a larger area.